review article an update on oligosaccharides and their
TRANSCRIPT
Review ArticleAn Update on Oligosaccharides and Their Esters fromTraditional Chinese Medicines Chemical Structures andBiological Activities
Xiang-Yang Chen Ru-Feng Wang and Bin Liu
School of Chinese Medicine Beijing University of Chinese Medicine Beijing 100102 China
Correspondence should be addressed to Bin Liu liubinyn67163com
Received 18 July 2014 Revised 25 November 2014 Accepted 2 January 2015
Academic Editor Yong Jiang
Copyright copy 2015 Xiang-Yang Chen et al This is an open access article distributed under the Creative Commons AttributionLicense which permits unrestricted use distribution and reproduction in any medium provided the original work is properlycited
A great number of naturally occurring oligosaccharides and oligosaccharide esters have been isolated from traditional Chinesemedicinal plants which are used widely in Asia and show prominent curative effects in the prevention and treatment of kindsof diseases Numerous in vitro and in vivo experiments have revealed that oligosaccharides and their esters exhibited variousactivities including antioxidant antidepressant cytotoxic antineoplastic anti-inflammatory neuroprotective cerebral protectiveantidiabetic plant growth-regulatory and immunopotentiating activities This review summarizes the investigations on thedistribution chemical structures and bioactivities of natural oligosaccharides and their esters from traditional Chinese medicinesbetween 2003 and 2013
1 Introduction
Oligosaccharides and their esters a significant group ofphytochemical compounds are widely distributed in theroots rhizomes stems barks leaves aerial and whole partsof medicinal plantsThey not only serve as the energy storagecomponents but also play a vital role in the treatment of dis-eases Before 2003 there have been a number of reviews andreports in respect to the isolation and structure elucidationof oligosaccharides and their esters from Chinese medicinalplants [1ndash3] but few biological activities such as cancerchemopreventive and protein kinase C inhibitory activitieshad been reported [4ndash6] With the development of isolationand identification techniques [7ndash11] a larger number ofoligosaccharides and their esters have been endlessly identi-fied from traditional Chinese medicines in the past decadesThese compounds have a wide variety of structure typesbecause of the assembly of different monosaccharide unitsthe combination of various linking styles and the existence ofkinds of substituents And more promising biological activ-ities associated with some of the oligosaccharides and theiresters have been discovered In vitro and in vivo investigations
have demonstrated that they displayed antioxidant antide-pressant anti-inflammatory neuroprotective cerebral pro-tective antidiabetic cytotoxic antineoplastic plant growth-regulatory and immunopotentiating activities and so forthThis review aims to provide a systemic summary of thestudies on the distribution chemical structures and biologicalactivities of naturally occurring oligosaccharides and theiresters from traditional Chinesemedicines in the past decadesAmong these compounds the number of oligosaccharideesters is much greater than that of oligosaccharides andthe disaccharide esters are a very valuable source of activecompounds This information may help readers understandthe structure characteristics and therapeutic indications ofoligosaccharides and their esters from traditional Chinesemedicines and offer clues to the development of new drugs
2 Chemical Structures
Phytochemical investigations of traditional Chinesemedicines have shown that many botanical familiesincluding Polygalaceae Liliaceae Asteraceae PolygonaceaeSmilacaceae Scrophulariaceae Asclepiadaceae Arecaceae
Hindawi Publishing CorporationEvidence-Based Complementary and Alternative MedicineVolume 2015 Article ID 512675 23 pageshttpdxdoiorg1011552015512675
2 Evidence-Based Complementary and Alternative Medicine
Orobanchaceae Acanthaceae Rosaceae Musaceae Spargan-iaceae Leguminosae Equisetaceae Boraginaceae IridaceaeAlismataceae Lamiaceae Araliaceae Rubiaceae OleaceaeApocynaceae Caryophyllaceae Aspleniaceae and Trilliaceaeare rich in oligosaccharides and their esters Oligosaccharidesshow diversified structures because of the type and thenumber of monosaccharides as well as the positionof glycosidic bonds And oligosaccharide esters alsodisplay distinctive structural diversity largely owing to thenumber type and position of O-substituent units includingphenylpropanoid groups (eg coumaroyl feruloyl caffeoylsinapoyl 345-trimethoxycinnamoyl and cinnamoyl)benzoyl p-methoxybenzoyl and p-hydroxybenzoyl groups(Figure 2) Moreover the double bonds of phenylpropanoidgroups possess trans and cis isomeric forms of which thetrans forms widely exist in nature Hence according tothe number of monosaccharides and the characteristics ofchemical structures these oligosaccharide esters could becategorized into 7 large groups
21 Oligosaccharides All compounds of this group (Table 1and Figure 1) merely consist of various monosaccharideswithout O-substituents In addition to the well-knownsucrose 120573-D-glucopyranosyl(1rarr 2)-120573-D-glucopyranoside(1) was isolated from Camptosorus sibiricus [12] Theoligosaccharides of raffinose (3) stachyose (19) andverbascose (21) all of which belong to the Raffinose familypossess one two or three galactopyranosyl units linked tosucrose and have been found in the rhizomes and rootsof Alisma orientalis [13] Lycopus lucidus [14] Rehmanniaglutinosa [15 16] Salvia miltiorrhiza [17] and Scrophularianingpoensis [18] Manninotriose (4) and verbascotetraose (5)consisting of galactopyranosyl units and a glucopyranosylunit have been isolated from Alisma orientalis [13]
Five oligosaccharides comprising 1-kestose (6) nystose(7) 1-120573-fructofuranosylnystose (8) hexasaccharide (9) andheptasaccharide (10) consisting of fructofuranose and glu-copyranose have been isolated from the aerial parts and rootsof Gynura divaricata subsp formosana [19] Morinda offici-nalis [20ndash22] Saussurea lappa [23] and Aralia cordata [24]Two water-soluble oligosaccharides (11 12) composed of twoor three types of monosaccharides including glucopyranosefructopyranose and fructofuranose have been obtained fromthe whole plants of Blumea riparia [25 26]
Besides malto-oligosaccharides (17 119899 = 0sim8) consist-ing of 120572-D-glucopyranosyl residues assembled by (1rarr 4)-linkages and inulo-oligosaccharides (18 119899= 1sim3) consisting ofonly fructosyl residues formed by (2rarr 1)-linkages have beenfound in the roots of Panax ginseng [27 28] and Morindaofficinalis [20] respectively Three noteworthy oligosaccha-rides (2 13 14) formed by 120572-D-glucopyranosyl units with(1rarr 6)-linkages and a (1rarr 4)-linkage have been found in theroots of Panax ginseng [28] And two linear oligosaccharidestermed heptasaccharide (15) and octasaccharide (16) consist-ing of glucose and mannose monomers were identified fromthe rhizomes of Paris polyphylla var yunnanensis [29 30]A pentasaccharide stellariose (20) consisting of a raffinosebackbone with two galactosyl residues bound to the fructosyl
and glucosyl moieties was identified from the stems ofStellaria media [31]
Oligosaccharides (Table 1) are composed of seven kindsof deoxyhexoses including cymaropyranose canaropyra-nose digitoxopyranose oleandropyranose digitalopyranosecymaropyranurolactone and oleandronic acid-120575-lactoneOleandronic acid-120575-lactone exhibits the boat and chair con-formations The hydroxyl methyl and acetyl groups arelocated at the equatorial (e) and axial (a) bonds in the chairconformation of deoxyhexoses These oligosaccharides wereisolated from the traditional Chinesemedicines including theroots of Periploca forrestii the root barks of P sepium thestems of P calophylla and the barks of Parabarium huaitingii
22 Oligosaccharide Esters
221 Phenylpropanoid-Derived Disaccharide Esters Phenyl-propanoid-derived disaccharide esters (Table 2 and Figure 3)account for a considerable proportion of oligosaccharideesters and mainly possess a core of sucrose carryinga varying number of O-substituents including phenyl-propanoid groups acetyl benzoyl p-methoxybenzoyl andp-hydroxybenzoyl groups Phenylpropanoid substituents arejust present at 11015840 31015840 41015840 61015840 positions of 120573-D-fructofuranosylunit in compounds 35ndash97 whereas they appear at 2 3 46 positions of 120572-D-glucopyranosyl moiety in compounds98ndash101 Moreover compounds 76ndash97 are mainly esterifiedwith acetyl groups along with a phenylpropanoid sub-stituent coumaroyl feruloyl or 345-trimethoxycinnamoylgroup Interestingly the phenylpropanoid substituents areonly attached to the 31015840 position of sucrose The twosugar rings of compounds 102ndash128 both possess phenyl-propanoid substituents These oligosaccharide esters havebeen found in the roots and rhizomes of Polygala tricornisP tenuifolia Fagopyrum tataricum Scrophularia ningpoensisCynanchum amplexicaule Smilax riparia Paris polyphyllavar yunnanensis Smilacis glabrae Fagopyrum dibotrys andSparganium stoloniferum the underground parts of Tril-lium kamtschaticum the stems of Polygonum sachalinensisP cuspidatum P hydropiper Smilax china and Calamusquiquesetinervius the aerial parts of Polygala sibirica Smilaxbracteata Heterosmilax erythrantha and Musella lasiocarpathe leaves of Persicaria hydropiper and Polygonum hydropiperthe whole plants of Bidens parviflora and Polygala hongkon-gensis and the flower buds of Prunus mume
Cistanoside F (129) has been found in the stems ofCistanche tubulosa [80] and C sinensis [81] the barks of Pau-lownia tomentosa var tomentosa [82] and the aerial partsof Acanthus ilicifolius [83] Cistanoside I (130) has alsobeen isolated from the stems of the Cistanche plants [84]Both of them are composed of glucosyl and rhamnosylgroups connected by a 1rarr 3 glycosidic bond In addi-tion 661015840-sucrose ester of (1120572212057231205734120573)-34-bis(4-hydroxy-phenyl)-12-cyclobutanedicarboxylic acid (131) with a bis(4-hydroxyphenyl) cyclobutanedicarboxyl group as the acyl unitin the molecule structure was isolated from the whole plantsof Bidens parviflora [61]
Evidence-Based Complementary and Alternative Medicine 3
Table1Oligosaccharides
No
Nam
eR 1
R 2R 3
R 4R 5
R 6Source
Parts
Reference
22PerifosaccharideA
OH(e)
OCH
3(e)
HOH(e)
OH
APerip
loca
forrestii
Roots
[32]
23PerifosaccharideB
OH(e)
OCH
3(a)
HOH(e)
OH
APerip
loca
forrestii
Roots
[32]
24PerifosaccharideC
OH(e)
OCH
3(e)
HOH(e)
OCH
3A
Perip
loca
forrestii
Roots
[32]
25PerifosaccharideD
OAc
(e)
OCH
3(e)
HOH(e)
OH
APerip
loca
forrestii
Roots
[32]
26Peris
accharideA
OH(a)
OCH
3(e)
OAc
OH(e)
OCH
3A
Perip
loca
sepium
Root
barks
[33]
27Peris
accharideB
OAc
(e)
OCH
3(a)
HOH(e)
OH
APerip
loca
sepium
Perip
loca
calophylla
Root
barks
[3334]
28Peris
accharideC
OH(a)
OCH
3(e)
OAc
OCH
3(a)
OH
APerip
loca
sepium
Root
barks
[33]
29Peris
accharideD
OAc
(e)
OCH
3(a)
HOH(e)
OCH
3A
Perip
loca
calophylla
Stem
s[34]
30Peris
esaccharideB
OH(a)
OCH
3(e)
OAc
OH(e)
OCH
3C
Perip
loca
sepium
Root
barks
[35]
31Peris
esaccharideC
OH(a)
OCH
3(e)
OH
OCH
3(a)
OCH
3C
Perip
loca
sepium
Root
barks
[35]
32Peris
esaccharideD
OH(a)
OCH
3(e)
OH
OCH
3(a)
OH
CPerip
loca
sepium
Root
barks
[35]
33Peris
esaccharideE
OH(a)
OCH
3(e)
OAc
OH(e)
OH
CPerip
loca
sepium
Root
barks
[35]
34
Cymarop
yranurolactone
4-O-120573-D
-digita
lopyrano
syl-
(1rarr4)-O
-120573-D
-cymarop
yranosyl-(1rarr4)-O
-120573-
D-oleandrop
yranosyl-(1rarr4)-
O-120573-D
-cym
arop
yranoside
OH(a)
OCH
3(e)
OH
OCH
3(e)
OCH
3B
Parabariu
mhu
aitin
gii
Barks
[36]
SeeS
chem
e1
4 Evidence-Based Complementary and Alternative Medicine
R1
R2 R3
R4
R5
R6
O OO
OO
O
O
OO
O O OO
O
O
O
OCH3
H3COH3CO
H3CO
A oleandronic acid-120575-lactone B cymaropyranurolactone C oleandronic acid-120575-lactone
Scheme 1
222 Fatty Acid-Derived Disaccharide Esters Eight mono-substituted disaccharide esters (Table 3) with a sucrose moi-ety possess six different types of fatty acid residues whichattach to the 6 or 61015840 position of sucrose These fatty acidsinclude linoleic acid palmitic acid linolenic acid myris-tic acid hexadeca-71013-trienoic acid and hexadeca-710-dienoic acid The above sucrose fatty acid esters have beenfound in the rhizomes of Astragalus membranaceus and theroots of Equisetum hiemale
223 Lignan-DerivedDisaccharide Esters Six lignan-deriveddisaccharide esters (Figure 4) contain a sucrose core esterifiedwith different lignan residues covalently linked to the 31015840and 61015840 positions of 120573-D-fructofuranosyl unit and have beenisolated from the whole parts of Trigonotis peduncularis [85]and the aerial parts of Eritrichium rupestre [86]
224 Phenylpropanoid-Derived Trisaccharide Esters Inthis group all oligosaccharide esters consist of threemonosaccharides including glucopyranose fructofuranoseand rhamnopyranose with O-substituents which compriseferuloyl sinapoyl and 345-trimethoxycinnamoyl groupsOligosaccharide esters (146ndash149) listed in Table 4 as well askankanose (150) cistantubulose A
1A2(151) cistansinensose
A1A2(152) and compound 153 shown in Figure 5 have
been found in the roots of Polygala tricornis [37] the stemsof Cistanche tubulosa [81 87] and C sinensis [80] the wholeparts of Boschniakia rossica [88] and the rhizomes of Irisbrevicaulis [89]
225 Phenylpropanoid-Derived Tetrasaccharide Esters Phe-nylpropanoid-derived tetrasaccharide esters (154ndash159)(Table 5) consisting of three glucopyranosyl units and afructofuranosyl unit have been identified from the rootsof Polygala tricornis The nonsugar moieties of theseoligosaccharides include coumaroyl feruloyl sinapoyl and345-trimethoxycinnamoyl groups
226 Phenylpropanoid-Derived Pentasaccharide Esters Asshown in Table 6 oligosaccharide esters (160-179) possess-ing a skeleton of five sugar residues have been isolatedfrom the roots of Polygala tenuifolia The sugar residues
are composed of two types of monosaccharides includ-ing fructofuranose and glucopyranose which are esterifiedwith acetyl benzoyl rhamnose-substitutednonsubstitutedcoumaroyl and rhamnose-substitutednonsubstituted feru-loyl groups Other than that a structure-complex oligosac-charide polyester shown in Figure 5 polygalajaponicose I(180) consisting of a pentasaccharide backbone esterifiedwith feruloyl coumaroyl rhamnosyl-coumaroyl acetyl andbenzoyl groups has been obtained from the roots of Pjaponica [90]
227 Others Polygalatenosides AndashC (181ndash183) (Figure 6)containing a galactosyl unit and a polygolitosyl unit esterifiedwith benzoyl groups at 3 4 and 6 positions have been foundin the roots of Polygala tenuifolia [91] Three sucrose estersincluding polygalatenoside D (190) telephiose F (191) and6-O-benzoylsucrose (192) possess one benzoyl group twobenzoyl groups and a p-methoxybenzoyl group respectivelyThey were isolated from the roots of P tenuifolia [91] thewhole plants of P telephioides [92] and the roots of P tricornis[37] Six trisaccharide esters named telephioses AndashE and G(184ndash189) with substituents of acetyl and benzoyl groupswere isolated from the whole plants of P telephioides [92 93]Moreover a trisaccharide ester (193) pubescenside A fromthe flowers of Syringa pubescens possesses a fatty acid residue[94]
3 Biological Activities ofOligosaccharides and Their Esters
The oligosaccharides and oligosaccharide esters from Chi-nese medicinal plants are important products with diver-sified structures which have triggered an increasing num-ber of studies carried out on the isolated compoundsAnd thus diverse pharmacological activities have beenproved Among the isolated compounds oligosaccharidesphenylpropanoid-derived disaccharide esters and trisaccha-ride esters fatty acid-derived disaccharide esters and othersfrom the families Polygonaceae Asclepiadaceae RubiaceaePolygalaceae Liliaceae Smilacaceae Arecaceae Oroban-chaceae Scrophulariaceae Acanthaceae Rosaceae Sparga-niaceae Leguminosae and Equisetaceae have shown sig-nificant pharmacological activities including antioxidant
Evidence-Based Complementary and Alternative Medicine 5
1 2 3 4
5 6 7 8
9 10 11 12
13 14 15
16 17
OHOH
OH
OHOH
OHOH
OH
OHOH
OH
OO
O
OOO
HOHO
HO
HOHO CH2OH
CH2OH
CH2
2
2
3
4 5
5
66
6n
OH
OH
OH
OH
OHO O
O
OO
HO
HO
HO HO
HO
HO
OH
OHO OHO
HO OHO OHO
HO OHO
HOHO
OH
OH
OH
OH
OHOH
OHO OHO
HO OHO OHO
HO OHO
O
OO
OO
HO
HOHO
HOHO
HOHO
OHCH2OH
CH2
OH
OH
OH
OHO
OO
OO
HOHO HO
HOHO
HOHO
2
CH2OH
CH2
OH
OH
OH
OHO
OO
OO
HO
HOHO
HOHO
CH2OH
CH2
OH
OH
OH
OHO
OO
OO
HO
HOHO HO
HOHO
CH2OH
CH2
OH
OH
OH
OHO
OO
OO
HO
HO
HO HO
HOHO
CH2OH
CH2
OH
OH
OH
OHO
OO
OO
HO
HOHO HO
HOHO
CH2
OH
OH
OH OH
OHO
OO
OO
HO
HOHO HO
HOHO
OH
OH
OHOH
OH
OH
O
OO
O
OHO
HO
HOHO
HO
OH
OH
OH OHOH
OH
O
OO
O
OHO
HO
HOHO
HO
OH
OH OH
OH
OH
OH
OO
O O
O
HOHO HO
HO
HO
OH
OH OH
OH
OH
OO
O O
O
HOHO HO
HO
HOHO OH
OH
OH OHOH
OH
O
OO
O
O
HOHO
HO
HO
HO
Figure 1 Continued
6 Evidence-Based Complementary and Alternative Medicine
18 19
20 21
2
n
OH
OH
H
OH
OH
OH
OH
OO
O
O
O
HO
HOHO
HO
HO
CH2OH
OH
OHO OHO
HO OHO OHO
HO OH
OH
O
OO
HO
HOHO
HO
CH2OH
OH
OHO OHO
HO OHO OHO
HO OH
OH
O
OO
HO
HOHO
OH
OH
OHOHO
HO
OH
OH
OH
OH
OH
OHO
O
O
O
O
O
O
HO
HO
HO
OH
OH
OH
OH O
Figure 1
D benzoyl E p-methoxybenzoyl F p-hydroxybenzoyl G coumaroyl
I feruloyl J caffeoyl K sinapoyl
L 345-trimethoxycinnamoyl M cinnamoyl
O
O
O
O O O
OO
O
OCH3
OCH3
OCH3
OCH3
OCH3
OCH3
OCH3
OH
OHOH
OHOHOH
Figure 2
Evidence-Based Complementary and Alternative Medicine 7
Table2Ph
enylprop
anoid-deriv
eddisaccharid
eeste
rs
Num
ber
Nam
eR 1
R 2R 3
R 4R 5
R 6R 7
R 8Source
Parts
Reference
35Sibiric
oseA
6H
HH
HK
HH
HPolyg
alatricornis
Polyg
alatenu
ifolia
Roots
Root
barks
[37ndash40
]
3631015840-O
-FeruloylsucroseSibiricose
A5
HH
HH
IH
HH
Polyg
alatenu
ifolia
Trillium
kamtsc
haticum
Roots
Und
ergrou
ndparts
[38ndash42]
37GlomeratoseA
HH
HH
LH
HH
Polyg
alatricornis
Roots
[37]
38LapathosideD
HH
HH
GG
HH
Polyg
onum
sachalinense
Stem
s[43]
39Helo
niosideA
HH
HH
II
HH
Trillium
kamtsc
haticum
Smila
xbracteata
Paris
polyphylla
varyunn
anensis
Und
ergrou
ndparts
Aeria
lparts
Roots
[4144
45]
40Helo
niosideB
AcH
HH
II
HH
Smila
xbracteata
Smila
xchina
Smila
xrip
aria
Heterosmila
xerythrantha
Aeria
lparts
Stem
sRo
otsa
ndrhizom
es
[4446
ndash48]
41Paris
polysid
eFH
HH
HG
IH
HPa
risPolyphylla
varyunn
anensis
Rhizom
es[4950]
42Hydropiperosid
eH
HH
HG
GH
GPolyg
onum
sachalinense
Polyg
onum
cuspidatum
Persica
riahydropiper
Stem
sLeaves
[435152]
43Tricorno
seB
DAc
HH
LH
HH
Polyg
alatricornis
Roots
[37]
44Tenu
ifolisideA
FH
HH
LH
HH
Polyg
alatenu
ifolia
Polygalahongkongensis
Polyg
alasib
irica
Roots
Who
leplants
Aeria
lparts
[3840
4253ndash
56]
45Tataris
ideA
AcH
HAc
GG
HAc
Fagopyrum
tataric
umRo
ots
[57]
46Tataris
ideE
HH
HAc
GG
HAc
Fagopyrum
tataric
umRo
ots
[57]
47Tataris
ideG
HH
HH
IG
HG
Fagopyrum
tataric
umRo
ots
[57]
48Sm
iglasid
eAAc
AcH
AcI
IH
ISm
ilaxrip
aria
Rootsa
ndrhizom
es[47]
49Sm
iglasid
eBAc
HH
AcI
IH
ISm
ilaxrip
aria
Rootsa
ndrhizom
es[47]
50Sm
iglasid
eEAc
HH
AcI
IH
GSm
ilaxchina
Stem
s[46]
51Sm
ilasid
eAAc
AcH
HI
IH
HSm
ilaxchina
Stem
s[46]
52Sm
ilasid
eBH
HH
AcI
IH
HSm
ilaxchina
Stem
s[46]
53Sm
ilasid
eCH
HH
HI
IH
GSm
ilaxchina
Stem
s[46]
54Sm
ilasid
eDH
HH
HI
IAc
GSm
ilaxchina
Stem
s[46]
8 Evidence-Based Complementary and Alternative Medicine
Table2Con
tinued
Num
ber
Nam
eR 1
R 2R 3
R 4R 5
R 6R 7
R 8Source
Parts
Reference
55Sm
ilasid
eEAc
HH
HI
IH
GSm
ilaxbracteata
Smila
xchina
Aeria
lparts
Stem
s[4446
]
56Sm
ilasid
eFAc
HH
AcG
IH
GSm
ilaxchina
Stem
s[46]
57Sm
ilasid
eGH
HH
HG
IH
GSm
ilaxbracteata
Smilacis
glabrae
Aeria
lparts
Rhizom
es[4458]
58Sm
ilasid
eHH
HH
AcG
IH
GSm
ilaxbracteata
Aeria
lparts
[44]
59Sm
ilasid
eIAc
HH
HG
IH
GSm
ilaxbracteata
Aeria
lparts
[44]
60Sm
ilasid
eJH
HH
HG
IH
ISm
ilaxbracteata
Smilacis
glabrae
Aeria
lparts
Rhizom
es[4458]
61Sm
ilasid
eKH
HH
AcI
IH
GSm
ilaxbracteata
Aeria
lparts
[44]
62Sm
ilasid
eLH
HH
HI
IH
ISm
ilaxbracteata
Smilacis
glabrae
Aeria
lparts
Rhizom
es[4458]
63Sm
ilasid
eMAc
HH
AcCis-feruloyl
IH
HSm
ilaxrip
aria
Rootsa
ndrhizom
es[59]
64Sm
ilasid
eNAc
HH
AcI
Cis-
feruloyl
HH
Smila
xrip
aria
Rootsa
ndrhizom
es[59]
65Sm
ilasid
ePH
HH
AcI
IH
ISm
ilaxrip
aria
Rootsa
ndrhizom
es[47]
66310158404101584061015840-O
-Tri-
feruloylsucrose
HH
HH
II
IH
Smila
xrip
aria
Rhizom
esand
roots
[60]
6761015840-O
-Cou
maroylsu
crose
HH
HH
HG
HH
Bidens
parviflora
Who
leplants
[61]
6811015840 -O-C
oumaroyl-61015840-O
-feruloylsucrose
HH
HH
HI
HG
Smila
xbracteata
Aeria
lparts
[44]
694-O-Benzoyl-31015840-345-
trim
etho
xycinn
amoylsu
crose
HD
HH
LH
HH
Polyg
alatricornis
Roots
[37]
706-O-Benzoyl-31015840-O
-345-
trim
etho
xycinn
amoylsu
crose
DH
HH
LH
HH
Polyg
alatricornis
Roots
[37]
716-O-Benzoyl-31015840-O
-sin
apoylsu
crose
DH
HH
KH
HH
Polyg
alatricornis
Roots
[37]
726-O-p-M
etho
xybenzoyl-31015840-O
-345-
trim
etho
xycinn
amoylsu
crose
EH
HH
LH
HH
Polyg
alatenu
ifolia
Roots
[56]
7326-Di-a
cetyl-3101584061015840-di-
feruloylsucrose
AcH
HAc
II
HH
Smila
xchina
Smila
xrip
aria
Heterosmila
xerythrantha
Stem
sRo
otsa
ndrhizom
esAe
rialp
arts
[46ndash
4859]
7426-Di-a
cetyl-31015840-O
-cis-feruloy-
61015840-tr
ans-feruloylsucrose
AcH
HAc
Cis-feruloy
IH
HSm
ilaxrip
aria
Rootsa
ndrhizom
es[59]
Evidence-Based Complementary and Alternative Medicine 9
Table2Con
tinued
Num
ber
Nam
eR 1
R 2R 3
R 4R 5
R 6R 7
R 8Source
Parts
Reference
7526-Di-a
cetyl-31015840-O
-tran
s-feruloy-
61015840-cis-feruloylsucrose
AcH
HAc
ICis-
feruloyl
HH
Smila
xrip
aria
Rootsa
ndrhizom
es[59]
76Re
galosid
eAAc
HH
HI
HH
HTrillium
kamtsc
haticum
Und
ergrou
ndparts
[41]
77Tricorno
seA
AcH
HH
LH
HH
Polyg
alatricornis
Roots
[37]
78Mum
eose
AH
HH
AcG
HH
HPrun
usmum
eFlow
erbu
ds[6263]
79Mum
eose
BAc
HAc
HG
HH
HPrun
usmum
eFlow
erbu
ds[6263]
80Mum
eose
CAc
HAc
AcG
HH
HPrun
usmum
eFlow
erbu
ds[6263]
81Mum
eose
DAc
AcAc
AcG
HH
AcPrun
usmum
eFlow
erbu
ds[6263]
82Mum
eose
EAc
AcAc
AcCis-
coum
aroyl
HH
AcPrun
usmum
eFlow
erbu
ds[6263]
83Mum
eose
FAc
AcAc
HG
HH
HPrun
usmum
eFlow
erbu
ds[63]
84Mum
eose
GAc
HAc
HG
HAc
HPrun
usmum
eFlow
erbu
ds[63]
85Mum
eose
HH
HAc
AcG
HAc
HPrun
usmum
eFlow
erbu
ds[63]
86Mum
eose
IAc
AcAc
HG
AcH
HPrun
usmum
eFlow
erbu
ds[63]
87Mum
eose
JAc
AcAc
AcG
HAc
AcPrun
usmum
eFlow
erbu
ds[63 ]
88Mum
eose
KH
HAc
AcG
HH
HPrun
usmum
eFlow
erbu
ds[64]
89Mum
eose
LAc
HAc
AcG
HAc
HPrun
usmum
eFlow
erbu
ds[64]
90Mum
eose
MAc
AcAc
HG
HAc
AcPrun
usmum
eFlow
erbu
ds[64]
91Mum
eose
NAc
AcAc
HG
AcAc
HPrun
usmum
eFlow
erbu
ds[64]
92Mum
eose
OAc
HAc
AcG
HAc
AcPrun
usmum
eFlow
erbu
ds[64]
9311015840 2346-O-Penta-acetyl-31015840-O
-tra
ns-cou
maroylsu
crose
AcAc
AcAc
GH
HAc
Musellalasio
carpa
Aeria
lparts
[65]
9411015840 2346-O-Penta-acetyl-31015840-O
-cis-cou
maroylsu
crose
AcAc
AcAc
Cis-
coum
aroyl
HH
AcMusellalasio
carpa
Aeria
lparts
[65]
9511015840 236-O-Tetra-acetyl-31015840-O
-cis-
feruloylsucrose
AcH
AcAc
Cis-feruloyl
HH
AcSparganium
stolonifer
umRh
izom
es[66]
9611015840 246-O-Tetra-acetyl-31015840-O
-tra
ns-fe
ruloylsucrose
AcAc
HAc
IH
HAc
Sparganium
stolonifer
umRh
izom
es[66]
9711015840 236-O-Tetra-acetyl-31015840-O
-tra
ns-fe
ruloylsucrose
AcH
AcAc
IH
HAc
Sparganium
stolonifer
umRh
izom
es[67]
98Sibirio
sideA
MH
HH
HH
HH
Scrophularianingpoensis
Roots
[68]
99SibricoseA
1K
HH
HH
HH
HCy
nanchu
mam
plexica
ule
Roots
[69]
100
6-O-C
affeoylsucrose
JH
HH
HH
HH
Scrophularianingpoensis
Roots
[68]
101
Acretosid
eI
HH
HH
HH
HScrophularianingpoensis
Roots
[68]
10 Evidence-Based Complementary and Alternative Medicine
Table2Con
tinued
Num
ber
Nam
eR 1
R 2R 3
R 4R 5
R 6R 7
R 8Source
Parts
Reference
102
Tenu
ifolisideB
FH
HH
KH
HH
Polyg
alatenu
ifolia
Roots
[4256]
103
Tenu
ifolisideC
KH
HH
LH
HH
Polyg
alatricornis
Polyg
alatenu
ifolia
Roots
[374256]
104
Heterosmilasid
eH
HI
HH
IH
HHeterosmila
xerythrantha
Aeria
lparts
[48]
105
Quiqu
esetinerviusideA
HI
HH
II
HH
Calamus
quiquesetin
ervius
Stem
s[70]
106
Quiqu
esetinerviusideB
AcI
HH
II
HH
Calamus
quiquesetin
ervius
Stem
s[70]
107
Quiqu
esetinerviusideC
HI
HAc
II
HH
Calamus
quiquesetin
ervius
Stem
s[70]
108
Quiqu
esetinerviusideD
AcG
HH
II
HH
Calamus
quiquesetin
ervius
Stem
s[70]
109
Quiqu
esetinerviusideE
HG
HAc
II
HH
Calamus
quiquesetin
ervius
Stem
s[70]
110
Vanicosid
eAI
HH
AcG
GH
G
Polyg
onum
sachalinensis
Polyg
onum
cuspidatum
Polyg
onum
hydropiper
Stem
sLeaves
Rhizom
es[51527172]
111
Vanicosid
eBI
HH
HG
GH
G
Polyg
onum
sachalinensis
Polyg
onum
cuspidatum
Persica
riahydropiper
Stem
sLeaves
Rhizom
es[4351527172]
112
Vanicosid
eDG
HH
HG
GH
GPersica
riahydropiper
Leaves
[51]
113
Vanicosid
eEI
AcH
AcG
GH
GPolyg
onum
hydropiper
Stem
sand
leaves
[72]
114
LapathosideA
IH
HH
GG
HI
Polyg
onum
sachalinensis
Polyg
onum
cuspidatum
Fagopyrum
dibotrys
Stem
sRh
izom
es[5173]
115
LapathosideC
IH
HH
GG
HH
Polyg
onum
sachalinensis
Polyg
onum
cuspidatum
Stem
s[4352]
116
DibosideA
GH
HH
GI
HG
Fagopyrum
tataric
umFagopyrum
dibotrys
Roots
Rhizom
es[57]
117
Hidropiperosid
eAI
HH
HH
GH
GPolyg
onum
hydropiper
Stem
sand
leaves
[72]
118
Hidropiperosid
eBI
HH
AcG
GH
IPolyg
onum
hydropiper
Stem
sand
leaves
[72]
119
Tataris
ideB
IH
HAc
GG
HAc
Fagopyrum
tataric
umRo
ots
[57]
Evidence-Based Complementary and Alternative Medicine 11
Table2Con
tinued
Num
ber
Nam
eR 1
R 2R 3
R 4R 5
R 6R 7
R 8Source
Parts
Reference
120
Tataris
ideC
IAc
HAc
GG
HAc
Fagopyrum
tataric
umRo
ots
[57]
121
Tataris
ideD
GH
HAc
GI
HH
Fagopyrum
tataric
umRo
ots
[57]
122
Tataris
ideF
GH
HH
II
HG
Fagopyrum
tataric
umRo
ots
[57]
123
310158406-O
-Di-sinapoylsu
crose
KH
HH
KH
HH
Polyg
alatricornis
Polygalahongkongensis
Polyg
alasib
irica
Polyg
alatenu
ifolia
Cynanchu
mam
plexica
ule
Roots
Root
barks
Who
leplants
Aeria
lparts
[37ndash394153ndash
566974]
124
661015840-O
-Di-c
oumaroylsu
crose
GH
HH
HG
HH
Bidens
parviflora
Who
leplants
[61]
125
11015840 3101584061015840-O
-Tri-
coum
aroyl-6
-feruloylsucrose
IH
HH
GG
HG
Fagopyrum
tataric
umRo
ots
[7576]
126
3101584061015840-O
-Di-c
oumaroyl-110158406-O
-di-
feruloylsucrose
IH
HH
GG
HI
Fagopyrum
tataric
umRo
ots
[7576]
127
31015840-O
-Cou
maroyl-11015840610158406-O
-tri-
feruloylsucrose
IH
HH
IG
HI
Fagopyrum
tataric
umRo
ots
[7576]
128
11015840 31015840610158406-O
-Tetra-fe
ruloylsucrose
IH
HH
II
HI
Fagopyrum
tataric
umRo
ots
[7576]
SeeS
chem
e2
12 Evidence-Based Complementary and Alternative Medicine
131130129
CH2OHOH
OH
OO
OH
C
C
HH
HHO
OO
O
HO
HOHO
HO
HOOH
OHOHOH
OHOH
HOO
O
O
O
HO
HO
OH
OHOHOH
OHOH
HOO
O
O
O
HO
Figure 3
12
3
4
5
6
1998400
2998400
3998400
4998400
5998400
6998400
HO
O
O
R1O
R2O
R8O
R7OOR3
OR4 OR5OR6
Scheme 2
antidepressant cytotoxic antineoplastic anti-inflammatoryantidiabetic plant growth-regulatory neuroprotective andcerebral protective activities Lignan-derived disaccharideesters phenylpropanoid-derived tetrasaccharide esters andpentasaccharide esterswith biological activities have not beenreported Aside from the isolated constituents oligosaccha-ride mixtures from Rehmannia glutinosa Panax ginseng andScrophularia ningpoensiswere also reported to display diversepharmacological activities such as antidiabetic immunopo-tentiating enhanced memory and antineoplastic activitiesThese active compounds and mixtures could serve as thevaluable candidates to be developed as possible drugs for thetreatment and prevention of diseases
31 Antioxidant Activity The adverse effects of oxidativestress proposed to play significant roles in the pathogenesis ofcardiovascular diseases atherosclerosis hypertension can-cer diabetes mellitus neurodegenerative diseases rheuma-toid arthritis ischemiareperfusion injury and ageing havebecome an inevitable and serious issue [95 96] Scientistshave thus made great efforts to explore antioxidants frommedicinal plants by using different kinds of assay methodswhich include DPPH radical scavenging assay hydroxylradical scavenging assay superoxide anion scavenging assayand ABTS radical scavenging method [96]
Lapathosides C and D hydropiperoside vanicoside Bhidropiperosides A and B lapathoside A and diboside Awere isolated from the Polygonum Persicaria and Fagopyrumgenera belonging to the Polygonaceae family The DPPH testrevealed that free radical-scavenging activity of the isolatedcompounds termed lapathoside C (115) hydropiperoside(42) vanicoside B (111) and lapathoside D (38) increasedin turn and lapathoside D exhibited strongest scavengingability with an IC
50of 0088 120583M [43] Hidropiperosides A
and B (117 118) were reported to show obvious antioxidantresponse to DPPH radicals with the SC
50values of 234
and 267 120583gmL respectively while vanicoside E moderatelyexhibited the same activity with a SC
50value of 490 120583gmL
[72] Lapathoside A (114) and diboside A (116) just showedlower antioxidant activities with the SC
50values of 19948 and
16552 120583M respectively [73]Smiglasides A and B smilaside P 26-di-acetyl-3101584061015840-
di-feruloylsucrose helonioside B smilasides GndashL and het-erosmilaside were isolated from the Heterosmilax and Smi-lax genera Compared with ascorbic acid (IC
5014352 120583M)
used as positive control smiglasides A and B and smi-laside P (48 49 65) (IC
5033958 33066 and 31449 120583M
resp) showed higher antioxidant activities than 26-di-acetyl-3101584061015840-di-feruloylsucrose (73) and helonioside B (40) (IC
50
63166 and 51827120583M resp) [47] Additionally Nhiem et alreported that helonioside B heterosmilaside (104) and 26-di-acetyl-3101584061015840-di-feruloylsucrose exhibited important DPPHradical scavenging activities with the SC
50values of 91 127
and 87 120583gmL respectively [48] Compared with smilasidesG-I (57ndash59) (ED
50685ndash794120583M) smilasides JndashL (60ndash62)
showed higher radical scavenging activities with an ED50
value of 267ndash327120583M [44]Five quiquesetinerviusides AndashE (105ndash109) isolated from
the Calamus genus showed weak DPPH scavenging activ-ities (IC
50604ndash1018120583M) but exhibited better hydroxyl
radical scavenging activities (IC50
36ndash84 120583M) Moreoverquiquesetinerviuside C showed superoxide anion scaveng-ing activity with an IC
50value of about 1843 120583M [70]
Liu et al investigated the antioxidant capacity of 310158406-O-di-sinapoylsucrose (DISS) (123) by using the acceleratedsenescence-prone short-lived mice (SAMP) in vivo Theanalyses indicated that the activities of antioxidant enzymesof SOD and glutathione peroxidase ascended obviously inSAMP mice when amended with DISS 50mgkg MoreoverDISS could downregulate and even restore the level ofmalondialdehyde in SAMP model group [97]
From the above studies it can be concluded that oligosac-charide esters with antioxidant activities have been identifiedin the Polygonaceae Liliaceae Smilacaceae and Arecaceaefamilies The results of the antioxidant assays show that theincreased number of phenolic hydroxyl groups and acetylgroups could produce higher antioxidant activity Fan etal indicated that the increased number of phenylpropanoidgroups was not beneficial to free radical scavenging activity[43] Zhang et al pointed out that oligosaccharide esters withferuloyl groups exhibited better antioxidant activities thanthose with coumaroyl groups [44]
Evidence-Based Complementary and Alternative Medicine 13
Table 3 Fatty acid-derived disaccharide esters
Number Name R1 R2 Source Parts Reference132 61015840-O-Linoleylsucrose H O Astragalus membranaceus Roots [77]133 61015840-O-Palmitoylsucrose H P Astragalus membranaceus Roots [77]134 6-O-Palmitoylsucrose P H Astragalus membranaceus Roots [77]
135 61015840-O-Linolenoylsucrose H N Astragalus membranaceusEquisetum hiemale
RootsAerial parts [77 78]
136 6-O-Linoleylsucrose O H Astragalus membranaceus Roots [77]137 6-O-Myristoylsucrose Q H Astragalus membranaceus Roots [77]
138 6-O-[(7Z10Z13Z)-Hexadeca-71013-trienoyl]sucrose H R Equisetum hiemale Aerial parts [78]
139 6-O-[(7Z10Z)-Hexadeca-710-dienoyl]sucrose H S Equisetum hiemale Aerial parts [78]
See Scheme 3
12
3
4
5
6
1998400
2998400
3998400
4998400
5998400
6998400
HO
O
O
R1O
R2O
R8O
R7OOR3
OR4 OR5OR6
O
O
O
18
18
1616
16
14
N linolenoyl
O linoleyl
P palmitoyl
Q myristoyl
O
O
O
R hexadeca-71013-trienoyl
S hexadeca-710-dienoyl
Scheme 3
32 Antidepressant Activity The oligosaccharides obtainedfrom the Morinda genus not only show specific antidepres-sant and antistress activities but also have no suppression orexcitatory effects on central nervous system as well Whatis more they can be taken orally with little toxicity [21]The inulin-type hexasaccharide (IHS) (9) from Morindaofficinalis obviously exhibited cytoprotective activity whichcontributed to the antidepressant effect not only by providingthe PC12 with protection against Cort-induced lesion withIHS 0625 and 125 120583Mbut also by reducing theCort-induced[Ca2+]
119894overloading with IHS 25 and 10 120583M IHS 5 and
10 120583Mupregulated the nerve growth factormRNAexpressionin Cort-induced PC12 cells [22] Polygalatenosides A (181)and B (182) were isolated from the Polygala genus Theysignificantly inhibited the isotope-labeled RTI-55 binding to
norepinephrine transporter protein with the IC50
values of300 and 604 120583M respectively [91]
DISS and tenuifoliside A were isolated from the PolygalaandCynanchum genera Liu et al investigated the antidepres-sant effect of YZ ethanol extract based on the tail suspensiontest (TST) and forced swimming test (FST) which arethe ease-of-use and widely-accepted models for estimatingantidepressant activities in mice The results indicated thatYZ-50 fraction at a dose of 200mgkgwas able to significantlydecrease the immobility time in TST Furthermore YZ-50possessed ability to inhibit corticosterone-induced injury ofhuman neuroblastoma SH-SY5Y cells What is more DISS(123) and tenuifoliside A (44) two major compounds of YZ-50 fraction showed effective protective response to the lesionin SY5Y cells [53] The antidepressant-like effect of DISS at
14 Evidence-Based Complementary and Alternative Medicine
H3CO
HO
HOHO
HO
HO
HO
HOHO
O O
OO O
OO
O
O
O
OO
O
O
OH
OH
OH
OH
OCH3
OCH3
CH2OH
CH2OH
CH2OAc
CH2OAc
H3CO
HOHO
HO
O
O
O
OO
O
O
OH
OH
OH
OCH3
CH2OH
CH2OH
H3CO
H3CO H3CO
HOHO
HO
O
O
O
OO
O
O
OH
OH
OH
OCH3
CH2OH
CH2OAc
CH3O
H
HOHO
HO
HO
HOO O
OO O
OO
OH
OCH3
CH2OHCH2OH
H3CO H3CO
H
CH2CH2 HO
HO
HO
HO
HOO O
OO O
OO
OH
OCH3
CH2OHCH2OAc
H3CO
H
CH2
140 141 142
143 144 145
Figure 4
Table 4 Phenylpropanoid-derived trisaccharide esters
Number Name R1 R2 R3 R4 R5 R6 R7 Source Parts Reference146 Tricornose C K H H H H L H Polygala tricornis Roots [37]147 Tricornose D K H H H H K H Polygala tricornis Roots [37]148 Tricornose E K H H H K L H Polygala tricornis Roots [37]149 Tricornose F K H H H I L H Polygala tricornis Roots [37]See Scheme 4
O
OOO
O
R2O
R4O
R3O
R6O
OH
OH
OH
OH
OR1
OR5CH2OR7
Scheme 4
the doses of 5 10 and 20mgkg was also tested in chronicallymild stressed rats DISS was able to exhibit antidepressantactivity by upregulating the expression of noradrenergic-regulated plasticity genes including cell adhesion moleculeL1 brain-derived neurotrophic factor laminin and cAMP
response element binding protein factor in hippocampus[98] DISS improved the reward reaction by increasingsucrose intake and obviously decreased the levels of serumcortisol adrenocorticotrophic hormone and corticotropin-releasing factor Further DISS played an enhanced role inthe expression of mineralocorticoid receptor together withglucocorticoid receptor mRNA [99]
33 Cytotoxic and Antineoplastic Activities Smilasides AndashFand P smiglasides A and B smilaside P and helonioside Awere isolated from the Smilax Trillium and Paris generaKuo et al obtained smilasides AndashF (51ndash56) and evaluatedtheir cytotoxicity against human tumor cell lines comprisinghuman oral epithelium carcinoma (KB) human cervicalcarcinoma (Hela) human colon tumor (DLD-1) humanbreast adenocarcinoma (MCF-7) human lung carcinoma (A-549) and humanmedulloblastoma (Med) cells byMTTassayExperimental data indicated that all but smilaside C showedcytotoxicity against three to six human tumor cell lines(ED50
= 51ndash130 120583gmL) and smilasides DndashF (ED50
= 27ndash50 120583gmL) displayed strong cytotoxic activities against DLD-1 cells [46]Wang et al reported the antitumor constituents of
Evidence-Based Complementary and Alternative Medicine 15
OH
OH
OH
OH
OH
OHOH
OHOH
OHOH
OH
OHOHOH
OH
OH
OH
OHOH
OH
OH
OHOH
H
H H
HO
O
O
O
O
O
O
O
OO
OO
O
OO
O
HO
HO
HO
OO
O
O
OO
OO
O
OO
O
OO
O
OO
O
O
O
OO
O
O
OO
O
OO
OOOO
HO
HO
HO
HO
HO
HO
HO
HO
HO
HO
HOHO
HO
HO
HO
HO
HO
150 151 152
153 180
AcO
AcO
AcOAcO
OAc
OAc
CH2OH
OHOH
OH OHOH
OHOH
OH
OHOH
CH3O
Figure 5
Table 5 Phenylpropanoid-derived tetrasaccharide esters
Number Name R1 R2 R3 Source Parts Reference154 Tricornose G K H K Polygala tricornis Roots [37]155 Tricornose H K K K Polygala tricornis Roots [37]156 Tricornose I K K L Polygala tricornis Roots [37]157 Tricornose J K I L Polygala tricornis Roots [37]158 Tricornose K K I K Polygala tricornis Roots [37]159 Tricornose L K G K Polygala tricornis Roots [37]See Scheme 5
Smilax riparia including smiglasides A (48) and B (49) 26-di-acetyl-3101584061015840-di-feruloylsucrose (73) helonioside B (40)and smilaside P (65) Only smiglasidesA andB and smilasideP exhibited cytotoxicity against human tumor cell lines withdifferent inhibitory concentrations comparing with cisplatinand paclitaxel as positive controls [47] Helonioside A (39)exhibited higher cytotoxicity with the increase of concentra-tion (01ndash100120583gmL) [45] Tatarisides AndashG (45 119ndash121 46122 47) and diboside A (116) from the Fagopyrum genusexerted cytotoxic activities against different human cell linesand the cytotoxicity of tatariside C was the most remarkablewith the IC
50values ranging from 644 to 749 120583gmL [57]
11015840236-O-Tetra-acetyl-31015840-O-cis-feruloylsucrose (95) fromthe Sparganium plants exhibited extremely weak cyto-toxicity against the growth of mice Lung Adenocarcinoma
795 cell lines with an IC50
value of 116 120583gmL [66] SnS-2oligosaccharides mixture including raffinose (3) stachyose(19) and verbascose (21) from the roots of Scrophularianingpoensis had antitumor activity against the growth ofLewis pulmonary carcinoma cells transplanted into mice[18]
Disaccharide esters and oligosaccharides mixture fromthe Liliaceae Polygonaceae Sparganiaceae and Scrpophular-iaceae families showed effective cytotoxic and antineoplasticactivities The study results indicated that feruloyl and acetylgroups play an important role in mediating cytotoxicitywhich seems to be related to the substitution position offeruloyl groups The feruloyl groups at C-6 or C-11015840 are vitalfor cytotoxicity In addition the increased number of acetylgroups could induce higher tumoricidal activity
16 Evidence-Based Complementary and Alternative Medicine
Table 6 Phenylpropanoid-derived pentasaccharide esters
Number Name R1 R2 R3 R4 R5 R6 Source Parts Reference160 Tenuifoliose A G D I Ac Ac Ac Polygala tenuifolia Roots [38 42]161 Tenuifoliose B G D I H Ac Ac Polygala tenuifolia Roots [42]162 Tenuifoliose C G D I H H H Polygala tenuifolia Roots [42]163 Tenuifoliose F G D U Ac Ac Ac Polygala tenuifolia Roots [42]164 Tenuifoliose G G D U Ac H Ac Polygala tenuifolia Roots [42]165 Tenuifoliose H G D G Ac Ac Ac Polygala tenuifolia Roots [38 42 79]166 Tenuifoliose I G D G Ac H Ac Polygala tenuifolia Roots [42 79]167 Tenuifoliose J G D G H Ac Ac Polygala tenuifolia Roots [42]168 Tenuifoliose K G D G H H Ac Polygala tenuifolia Roots [42]169 Tenuifoliose L G D T Ac Ac Ac Polygala tenuifolia Roots [42 79]170 Tenuifoliose M G D T Ac H Ac Polygala tenuifolia Roots [42]171 Tenuifoliose N I D I Ac Ac Ac Polygala tenuifolia Roots [42]172 Tenuifoliose O I D I H Ac Ac Polygala tenuifolia Roots [42]173 Tenuifoliose P I D I H H Ac Polygala tenuifolia Roots [42]174 Tenuifoliose Q G D T H Ac Ac Polygala tenuifolia Roots [79]175 Tenuifoliose S G D G H H H Polygala tenuifolia Roots [42]176 Tenuifoliose T G D I H H H Polygala tenuifolia Roots [42]177 Tenuifoliose V H D I Ac Ac Ac Polygala tenuifolia Roots [42]178 Tenuifoliose W I D U Ac H Ac Polygala tenuifolia Roots [42]179 Tenuifoliose X I D I H H H Polygala tenuifolia Roots [42]See Scheme 6
O
OO
O
O
O
O
OR1
OH
OH
OH
OHOH
OH
HOHO
HO
HO
OR2
R3O
CH2OH
Scheme 5
34 Anti-Inflammatory Activity Inflammation an importantbasic pathological process is a defense response of biopsywith vascular system to damage stimuli such as pathogensimpaired cells and tissues and physical and chemical factorsHowever if the process of inflammatory response cannot endnormally when cell debris and pathogens were cleared thebiological defence response will become causative factor andbring about many diseases such as diabetes cardiovasculardiseases metabolic syndrome and cancer [100 101]
Tenuifoliside A (44) from the Polygala genus exhibitedstrong anti-inflammatory effect not only by suppressing the
production of NO but also by reducing the production ofiNOS prostaglandin E2 cyclooxygenase-2 and proinflam-matory cytokines through the inhibition of the mitogen-activated protein kinases pathway and NF-120581B pathway [102]The anti-inflammatory activities of quiquesetinerviusides D(108) and E (109) from the Calamus genus were evaluated inRAW 2647 cells Both of them showed significant inhibitoryeffects against the production of LPS-stimulated NOwith theIC50values of 90ndash295120583M [70]Six disaccharide fatty acid esters (132ndash137) were iso-
lated from the Astragalus and Equisetum genera The anti-inflammatory effects of these isolated compounds have alsobeen documented The activation of NF-120581B could upregulatethe expression of proinflammatory cytokines inducible nitricoxide synthase (iNOS) and tumornecrosis factor alpha (TNF-120572) The NF-120581B inhibitory activities of compounds 132ndash137were tested in HepG2 cells stimulated with TNF-120572 All ofthese compounds could significantly restrainTNF-120572-inducedNF-120581B transcriptional activities with the IC
50values of 44ndash
247 120583M Li et al pointed out that olefinic bonds and thelength of the fatty acid moieties contributed to the NF-120581B inhibitory activity Furthermore the inhibition increasedsignificantly with the increase of the number of olefinic bondson the aliphatic moiety [77] These results may provide ascientific basis for the development of new anti-inflammatoryagents
35 Neuroprotective and Cerebral Protective Activities Aswe all know glutamate works as a major excitatory aminoacid neurotransmitter in the mammalian central nervous
Evidence-Based Complementary and Alternative Medicine 17
R6O
R2O
OR3
OR5
OR4
CH2OR1
OCH3
Rham
OO
O
OO O
O
O
O
OO
RhamO
O
OH
OH
OHOH
OH
OHOH
OHHO
HO
HO
T O-rhamnosyl-coumaroyl U O-rhamnosyl-feruloyl
Scheme 6
system and plays a crucial role in several physiological pro-cesses [103] However the accumulation of glutamate inducesdiverse acute and chronic neurodegenerative diseases suchas epilepsy ischemic stroke and Parkinsonrsquos disease aswell as Alzheimerrsquos disease [104] DISS (123) isolated fromthe Polygala genus exhibited neuroprotective effect againstglutamate-induced SH-SY5Y neuronal cell damage The invitro test demonstrated that DISS (06 6 and 60 120583molL)played a critical role in increasing cell viability controllinglactate dehydrogenase and attenuated apoptosis ranging from195 to 258 [105]
Tenuifoliside B (102) from the Polygala genus was ableto significantly shorten the coma time of KCN-inducedanoxia mice at the doses of 3 and 10mgkg and it playedan important role in ameliorating the scopolamine-inducedimpairment of performance in passive avoidance task inrats and enhancing the tremors induced by oxotremorine inmiceThese results together demonstrated that tenuifoliside Bpossessed cognitive improving and cerebral protective effects[56]
36 Antidiabetic Activity Diabetes mellitus a chronic debil-itating metabolic disease is characterized by high bloodglucose content and comprises three types termed type Itype II and gestational diabetes [106] Stachyose (19) extract(a part) from Rehmannia glutinosa obviously exhibited theactivity of downregulating fasting plasma glucose level andpartially keeping from hyperglycemia induced by adrenalineand glucose without obvious dose-dependent effect Otherthan that in vivo tests in rats induced by alloxan revealed
that stachyose extract at the dose of 200mgkg significantlydecreased blood-sugar level [15]
Diboside A lapathosides C and D vanicosides A andB and hydropiperoside were isolated from the FagopyrumPolygonum and Persicaria genera belonging to the Polygo-naceae family Diboside A (116) could potentially inhibit 120572-amylase activity with an IC
50of 269 120583M and thus retard the
starch digestion rate which is helpful for diabetic individualsin controlling blood sugar level [107] Lapathoside D (38)exerted stronger activity of 120572-glucosidase inhibition with anIC50
value of 0113mM than acarbose which was chosen asa positive drug for the treatment of type II diabetes [43]Vanicoside B (111) was reported to have higher 120573-glucosidaseinhibitory activity with an IC
50of 505 120583M than vanicoside A
(110) with an IC50of 599 120583M because of the acetyl moiety of
the latter possibly decreasing inhibitory activity of vanicosideA [71]
Fujimoto et al investigated the inhibitory effects ofmumeoses FndashO (83ndash92) from the Prunus genus on aldosereductase and discovered that caffeoyl groups are crucialfor the inhibitory effect on aldose reductase And thusmumeoses F G H J K L M and N (IC
50= 22ndash77120583M) with
a coumaroyl group and acetyl groups inhibited moderatelyaldose reductase from reducing glucose to sorbitol whichis associated with the chronic complications of diabetes [6364]
37 Elicitors and Regulators Oligosaccharides are quitepropitious for encoding biological information because ofdiverse monosaccharide units and complex molecular struc-tures and they are therefore first described as biological
18 Evidence-Based Complementary and Alternative Medicine
181 H
H
H
H
H
H
H
H
H H
H
H
H
H
H
H
H H
HH
Benzyl
Benzyl
Benzyl
182
183
184 Ac
Ac
Ac
Ac
Ac
Ac
Ac
Ac
Ac
Ac
185
186
187
188
189
R1 R2 R3
R1 R2 R3 R4
OCH3
R3OH2C OR2
OR1
OR1
O
O
O
O O
OOO
O
OO
O
OH
OH
OH OH
OH
O O
O
O
OH
HO
OH
OH OHOH
OH
OH
OHHO
HO
OH
OH
HO
CH2OH
CH2OH
CH2OH
CH2OH
C
R2O
R3O
CH2OR4
CH2CH2 CH2CH2CH2CH2CH3
CH3
CH3
191190 192
193
O
C C
O
OO
OO
OO
OO
O O
O
O
O
O
O
O
OH
OH
OHHO
HO
HOOH
OH
OH
OH
HO
OH
OH
OH
OH
HO
HO
C C
R998400O
R998400
Figure 6
signals in plants [108] Oligosaccharides from the cell wallfragments of plants and fungi are powerful signal moleculessuch as the elicitors of plant defence response and theregulators of plant growth and they are capable of exertingbiological activities at exceedingly low concentrations [109]Heptasaccharide (HS) (15) and octasaccharide (OS) (16) iso-lated from the Paris genus possessed plant growth-regulatory
activities [29 30]The two oligosaccharides significantly pro-moted the proliferation of Paris polyphylla var yunnanensisroots at the doses of 25ndash20mgL The octasaccharide hadthe most obvious effect on the growth of Panax japonicusvar major hairy roots at a dose of 30mgL while the otherhad the most positive effect on saponin accumulation ofPanax japonicus var major hairy roots at a dose of 10mgL
Evidence-Based Complementary and Alternative Medicine 19
[29] Similarly Zhou et al evaluated the stimulating effectsof HS and OS on the root growth and saponin productionof Panax ginseng hairy roots which were induced from theplant roots infected withAgrobacterium rhizogenes strain A4The results showed that there was a maximum effect on thehairy roots growth and saponin accumulation on day 10Compared with control group the root biomass dry weightwas increased by more than 17-fold while the total saponincontent of roots increased by more than 1-fold when thesetwo oligosaccharides were added to the hairy root at a dose of30mgL [30] The above data illustrate that HS and OS couldserve as the plant growth-regulators not only in their originalspecies but also in others
38 Immunopotentiating Activity Macrophages are impor-tant targets of investigations on cytophagy cellular immunityand molecular immunology Therefore they are deemedto play a vital role in host defense comprising phagocy-tosis proteolytic processing pathogenic agent apoptosiscytokines production and foreign antigens presentation[110] The water-extracted oligosaccharides from Panax gin-seng (WGOS) exhibited better immunopotentiating activ-ity by increasing phagocytic function of macrophages andpromoting NO TNF-120572 and reactive oxygen species pro-duction [110] In addition Wan et al have obtained malto-oligosaccharides (17 119899 = 3sim8) and three oligosaccharides (213 14) from the Panax ginseng roots The in vitro bioassaypointed out thatWGOS could serve as efficacious stimulatorsof B and T lymphocytes [28] These studies provided enlight-enment that the mixture of oligosaccharides from Chineseherbalmedicine exhibits significant effect on immune system
39 Others Acetylcholinesterase (AChE) inhibitors showgood therapeutic effects onmyasthenia gravis glaucoma andAlzheimerrsquos disease through reversible enzyme inhibitionso as to increase the accumulation of acetylcholine in thesynapse and then promote and prolong the function ofacetylcholine Vanicoside B (111) showed AChE inhibitoryactivity with an IC
50of 0062mM while hydropiperoside
(42) and lapathosides C (115) and D (38) just exhibited weakenzyme inhibitory activity [43]
Wang et al has explored low molecular mass carbohy-drate polymer from Panax ginseng roots and obtained 30ethanol elution (PGO)which included peptides and oligosac-charides (17 119899 = 0sim5) identified as maltose maltotriosemaltotetraose maltopentaose maltohexaose and maltohep-taose Pharmacological experiments revealed that PGO couldsignificantly enhance the memory in scopolamine-inducedmemory deficit rats [27]
Cistanoside F (129) and kankanose (150) were isolatedfrom the Cistanche Paulownia and Acanthus genera Phar-macological experiments showed that cistanoside F andkankanose significantly exhibited vasorelaxant effects on thenoradrenaline-induced contraction of thoracic aorta fromrats [80]
4 Conclusion
Traditional Chinese medicine from natural kingdom playsan indelible role in the treatment of human diseases andit has aroused the attention of those who have engagedin medicinal pharmaceutical chemistry Therefore scientistshave made great contributions day after day to investigate thevalid chemicals from traditional Chinese medicines In thepast decades about 193 oligosaccharides and their esters havebeen identified from traditional Chinese medicinal plantsOn the one hand only a few oligosaccharides and theirmixtures were investigated and just exhibited antidepres-sant antineoplastic antidiabetic plant growth-regulatoryimmunopotentiating and enhancedmemory activitiesMoreexploratory work is still needed to excavate biological andpharmacological activities of oligosaccharides On the otherhand oligosaccharide esters exhibited multi-advantageousactivities Bioassays have revealed that antioxidant cytotoxicantineoplastic and anti-inflammatory activities are the mostnotable bioactivities Of course to search for the naturalproducts with these activities is a hotpot in the contemporarydrug research Oligosaccharide esters provide a vast treasuretrove for medical researchers After considering the currentstudies it should be taken as future directions to makemore mechanism of action studies and clinical trials tofurther evaluate its potential as new drugs Moreover thestructure-activity relationships discussed in this review willprovide reference information for further exploring theirrelationships and continually discovering the new bioactiveoligosaccharide esters
Conflict of Interests
The authors declare that there is no conflict of interestsregarding the publication of this paper
References
[1] X D Yang L J Zhang B Liang L Z Xu and S L YangldquoOligosaccharide esters isolated from plants of PolygalaceaerdquoChinese Traditional and Herbal Drugs vol 33 no 10 pp 954ndash958 2002
[2] N Ogwuru and M Adamczeski ldquoBioactive natural productsderived from Polygonum species of plants their structures andmechanisms of actionrdquo Studies in Natural Products Chemistryvol 22 pp 607ndash642 2000
[3] S Kobayashi T Miyase and H Noguchi ldquoPolyphenolic glyco-sides and oligosaccharide multiesters from the roots of Polygaladalmaisianardquo Journal of Natural Products vol 65 no 3 pp 319ndash328 2002
[4] M Takasaki S Kuroki M Kozuka and T Konoshima ldquoNewphenylpropanoid esters of sucrose from Polygonum lapathi-foliumrdquo Journal of Natural Products vol 64 no 10 pp 1305ndash1308 2001
[5] M L Zimmermann and A T Sneden ldquoVanicosides A and Bprotein kinase C inhibitors from Polygonum pensylvanicumrdquoJournal of Natural Products vol 57 no 2 pp 236ndash242 1994
[6] M Takasaki T Konoshima S Kuroki H Tokuda and HNishino ldquoCancer chemopreventive activity of phenylpropanoid
20 Evidence-Based Complementary and Alternative Medicine
esters of sucrose vanicoside B and lapathoside A from Poly-gonum lapathifoliumrdquo Cancer Letters vol 173 no 2 pp 133ndash138 2001
[7] Q Fu T Liang Z Y Li et al ldquoSeparation of carbohydrates usinghydrophilic interaction liquid chromatographyrdquo CarbohydrateResearch vol 379 pp 13ndash17 2013
[8] M F Mrozek D Zhang and D Ben-Amotz ldquoOligosaccharideidentification and mixture quantification using Raman spec-troscopy and chemometric analysisrdquo Carbohydrate Researchvol 339 no 1 pp 141ndash145 2004
[9] G S Armstrong and B Bendiak ldquoHigh-resolution four-dimen-sional carbon-correlated 1H-1H ROESY experiments employ-ing isotags and the filter diagonalization method for effectiveassignment of glycosidic linkages in oligosaccharidesrdquo Journalof Magnetic Resonance vol 181 no 1 pp 79ndash88 2006
[10] G S Armstrong V A Mandelshtam A J Shaka and BBendiak ldquoRapid high-resolution four-dimensional NMR spec-troscopy using the filter diagonalization method and its advan-tages for detailed structural elucidation of oligosaccharidesrdquoJournal of Magnetic Resonance vol 173 no 1 pp 160ndash168 2005
[11] H-M Tseng S Gattolin J Pritchard H J Newbury and DA Barrett ldquoAnalysis of mono- di- and oligosaccharides by CEusing a two-stage derivatization method and LIF detectionrdquoElectrophoresis vol 30 no 8 pp 1399ndash1405 2009
[12] N Li X Li B L Hou and D L Meng ldquoNew disaccharosidefrom Camptosorus sibiricus Ruprrdquo Natural Product Researchvol 22 no 15 pp 1379ndash1383 2008
[13] Z Zhang D Wang Y Zhao H Gao Y-H Hu and J-FHu ldquoFructose-derived carbohydrates from Alisma orientalisrdquoNatural Product Research vol 23 no 11 pp 1013ndash1020 2009
[14] X Yang Y Zhao N He and K D Croft ldquoIsolation char-acterization and immunological effects of 120572-galacto-oligo-saccharides from a new source the herb Lycopus lucidus TurczrdquoJournal of Agricultural and Food Chemistry vol 58 no 14 pp8253ndash8258 2010
[15] R X Zhang Z P Jia L Y Kong et al ldquoStachyose extractfrom Rehmannia glutinosa Libosch to lower plasma glucose innormal and diabetic rats by oral administrationrdquo Pharmazievol 59 no 7 pp 552ndash556 2004
[16] R Zhang Y Zhao Y Sun X Lu and X Yang ldquoIsolationcharacterization and hepatoprotective effects of the raffinosefamily oligosaccharides from Rehmannia glutinosa liboschrdquoJournal of Agricultural and Food Chemistry vol 61 no 32 pp7786ndash7793 2013
[17] H Li F Song Z Zheng Z Liu and S Liu ldquoCharacterization ofsaccharides and phenolic acids in the Chinese herb Tanshen byESI-FT-ICR-MS and HPLCrdquo Journal of Mass Spectrometry vol43 no 11 pp 1545ndash1552 2008
[18] J E Deng J Zhang XM ChenW Ke and G Y Tian ldquoStudieson the physicochemical properties structure and antitumoractivity of an oligosaccharide homologue SnS-2 from the root ofScrophularia ningpoensis Hemslrdquo Chinese Journal of Chemistryvol 22 no 5 pp 492ndash497 2004
[19] S C Chou LM Chuang and S S Lee ldquoHypoglycemic constit-uents of gynura divaricata subsp formosanardquo Natural ProductCommunications vol 7 no 2 pp 221ndash222 2012
[20] F Feng L-L Wang X-P Lai Y-B Li Z-M Cao and Y-J Zhou ldquoStudy on oligosaccharides from Morinda officinalisrdquoJournal of Chinese Medicinal Materials vol 35 no 8 pp 1259ndash1262 2012
[21] Y F Li Z H Gong M Yang Y M Zhao and Z P Luo ldquoInhibi-tion of the oligosaccharides extracted fromMorinda officinalis
a Chinese traditional herbal medicine on the corticosteroneinduced apoptosis in PC12 cellsrdquo Life Sciences vol 72 no 8 pp933ndash942 2003
[22] Y-F Li Y-Q Liu M Yang et al ldquoThe cytoprotective effect ofinulin-type hexasaccharide extracted from Morinda officinalison PC12 cells against the lesion induced by corticosteronerdquo LifeSciences vol 75 no 13 pp 1531ndash1538 2004
[23] D N Olennikov L M Tankhaeva and A V Rokhin ldquoGlu-cofructans from Saussurea lappa rootsrdquo Chemistry of NaturalCompounds vol 47 no 3 pp 339ndash342 2011
[24] S K Hyun H A Jung B S Min J H Jung and J S ChoildquoIsolation of phenolics nucleosides saccharides and an alkaloidfrom the root of Aralia cordatardquo Natural Product Sciences vol16 no 1 pp 20ndash25 2010
[25] Z J Xu C W Lin and M F Liao ldquoStructure analysis of a newoligosaccharides BROS from Blumea ripariardquo Chinese Journalof Organic Chemistry vol 31 no 11 pp 1811ndash1819 2011
[26] Z J Xu C W Lin and Y Shi ldquoIsolation and structuredetermination of a new oligosaccharide from Blume ripariardquoJournal of Medicinal Plants Research vol 5 no 14 pp 2956ndash2962 2011
[27] Y Wang R Z Jiang G R Li et al ldquoStructural and enhancedmemory activity studies of extracts from Panax ginseng rootrdquoFood Chemistry vol 119 no 3 pp 969ndash973 2010
[28] DWan L Jiao H Yang and S Liu ldquoStructural characterizationand immunological activities of the water-soluble oligosaccha-rides isolated from thePanax ginseng rootsrdquoPlanta vol 235 no6 pp 1289ndash1297 2012
[29] L G Zhou C Z Yang J Q Li S L Wang and J Y WuldquoHeptasaccharide and octasaccharide isolated from Paris pol-yphylla var yunnanensis and their plant growth-regulatoryactivityrdquo Plant Science vol 165 no 3 pp 571ndash575 2003
[30] L G Zhou X D Cao R F Zhang Y L Peng S J Zhao andJ Y Wu ldquoStimulation of saponin production in Panax ginsenghairy roots by two oligosaccharides from Paris polyphylla varyunnanensisrdquo Biotechnology Letters vol 29 no 4 pp 631ndash6342007
[31] M Vanhaecke W van den Ende E Lescrinier and N Dyu-bankova ldquoIsolation and characterization of a pentasaccharidefrom Stellaria mediardquo Journal of Natural Products vol 71 no 11pp 1833ndash1836 2008
[32] J Feng and W Zhao ldquoComplete 1Hand 13C NMR assignmentsof four new oligosaccharides and two new glycosides fromPeriploca forrestiirdquoMagnetic Resonance in Chemistry vol 47 no8 pp 701ndash705 2009
[33] J Q Feng R J Zhang Y Zhou et al ldquoImmunosuppressive preg-nane glycosides from Periploca sepium and Periploca forrestiirdquoPhytochemistry vol 69 no 15 pp 2716ndash2723 2008
[34] X H Long R Xu Y H Zhang X H Tan andQ Y Sun ldquoA newoligosaccharide from Periploca calophyllardquo Zhongguo ZhongyaoZazhi vol 37 no 2 pp 226ndash229 2012
[35] L Wang Z-Q Yin Y Wang X-Q Zhang Y-L Li and W-CYe ldquoPerisesaccharides A-E new oligosaccharides from the rootbarks ofPeriploca sepiumrdquoPlantaMedica vol 76 no 9 pp 909ndash915 2010
[36] T Lei L Zhang H-Y Jiang Y Hu A-H Hong and Y-Z CenldquoA new pregnane glycoside and oligosaccharide from Parabar-ium huaitingiirdquo Journal of Asian Natural Products Research vol13 no 11 pp 1030ndash1035 2011
[37] J Li Y Jiang and P F Tu ldquoTricornoses A-L oligosaccharidemulti-esters from the roots of Polygala tricornisrdquo Journal ofNatural Products vol 68 no 5 pp 739ndash744 2005
Evidence-Based Complementary and Alternative Medicine 21
[38] H H Tu P Liu L Mu et al ldquoStudy on antidepressant com-ponents of sucrose ester from Polygala tenuifoliardquo ZhongguoZhongyao Zazhi vol 33 no 11 pp 1278ndash1280 2008
[39] G M She Y Y Ba Y Liu H Lv W Wang and R B ShildquoAbsorbable phenylpropenoyl sucroses from Polygala tenuifo-liardquoMolecules vol 16 no 7 pp 5507ndash5513 2011
[40] J Yong and P F Tu ldquoStudies on the chemical constituents inroot bark of Polygala tenuifolia (II)rdquo China Journal of ChineseMateria Medica vol 29 no 8 pp 751ndash753 2004
[41] M Ono C Takamura F Sugita et al ldquoTwo new steroidglycosides and a new sesquiterpenoid glycoside from theunderground parts of Trillium kamtschaticumrdquo Chemical andPharmaceutical Bulletin vol 55 no 4 pp 551ndash556 2007
[42] Y Ling Z Li M Chen Z Sun M Fan and C HuangldquoAnalysis and detection of the chemical constituents of RadixPolygalae and their metabolites in rats after oral administrationby ultra high-performance liquid chromatography coupledwith electrospray ionization quadrupole time-of-flight tandemmass spectrometryrdquo Journal of Pharmaceutical and BiomedicalAnalysis vol 85 pp 1ndash13 2013
[43] P Fan L Terrier A-E Hay A Marston and K HostettmannldquoAntioxidant and enzyme inhibition activities and chemicalprofiles ofPolygonum sachalinensis FSchmidt exMaxim (Polyg-onaceae)rdquo Fitoterapia vol 81 no 2 pp 124ndash131 2010
[44] L J Zhang C C Liao H C Huang Y C Shen L M Yangand Y H Kuo ldquoAntioxidant phenylpropanoid glycosides fromSmilax bracteatardquo Phytochemistry vol 69 no 6 pp 1398ndash14042008
[45] L L Yan W Y Gao Y J Zhang and Y Wang ldquoA new phenyl-propanoid glycosides from Paris polyphylla var yunnanensisrdquoFitoterapia vol 79 no 4 pp 306ndash307 2008
[46] Y H Kuo Y W Hsu C C Liaw J K Lee H C Huang andL M Y Kuo ldquoCytotoxic phenylpropanoid glycosides from thestems of Smilax chinardquo Journal of Natural Products vol 68 no10 pp 1475ndash1478 2005
[47] W-X Wang T-X Li H Ma J-F Zhang and A-Q JialdquoTumoral cytotoxic and antioxidative phenylpropanoid glyco-sides in Smilax riparia A DCrdquo Journal of Ethnopharmacologyvol 149 no 2 pp 527ndash532 2013
[48] N X Nhiem P vanKiem C vanMinh et al ldquoPhenylpropanoidglycosides fromHeterosmilax erythrantha and their antioxidantactivityrdquo Archives of Pharmacal Research vol 32 no 10 pp1373ndash1377 2009
[49] Y Wang W Y Gao T J Zhang and Y Q Guo ldquoA novelphenylpropanoid glycosides and a new derivation of phenolicglycoside from Paris Polyphylla var yunnanensisrdquo ChineseChemical Letters vol 18 no 5 pp 548ndash550 2007
[50] J-Y Zhang Y-Z Wang Y-L Zhao et al ldquoPhytochemicals andbioactivities of Paris speciesrdquo Journal of Asian Natural ProductsResearch vol 13 no 7 pp 670ndash681 2011
[51] N H N Hashim F Abas K Shaari and N H Lajis ldquoLC-DAD-ESIMSMS characterization of antioxidant and anti-cholinesterase constituents present in the active fraction fromPersicaria hydropiperrdquo LWT Food Science and Technology vol46 no 2 pp 468ndash476 2012
[52] PH FanA EHayAMarstonHX Lou andKHostettmannldquoChemical variability of the invasive neophytes Polygonumcuspidatum Sieb and Zucc and Polygonum sachalinensis FSchmidt ex Maximrdquo Biochemical Systematics and Ecology vol37 no 1 pp 24ndash34 2009
[53] P Liu Y Hu D H Guo et al ldquoPotential antidepressantproperties of Radix Polygalae (Yuan Zhi)rdquo Phytomedicine vol17 no 10 pp 794ndash799 2010
[54] J F Wu S B Chen S L Chen and P F Tu ldquoThe chemical con-stituents of Polygala hongkongensisHemslrdquoActa PharmaceuticaSinica vol 42 no 7 pp 757ndash761 2007
[55] Y Song Y Jiang D Bi X Tian L Liang and P Tu ldquoChemicalconstituents from n-butanol extract of aerial part of Polygalasibiricardquo Zhongguo Zhongyao Zazhi vol 37 no 4 pp 471ndash4742012
[56] Y Ikeya S Takeda M Tunakawa et al ldquoCognitive improvingand cerebral protective effects of acylated oligosaccharides inPolygala tenuifoliardquo Biological and Pharmaceutical Bulletin vol27 no 7 pp 1081ndash1085 2004
[57] C J Zheng C L Hu X Q Ma C Peng H Zhang and L PQin ldquoCytotoxic phenylpropanoid glycosides from Fagopyrumtataricum (L) Gaertnrdquo Food Chemistry vol 132 no 1 pp 433ndash438 2012
[58] X Li Y F Zhang L Yang et al ldquoChemical profiling ofconstituents of Smilacis glabrae using ultra-high pressure liquidchromatography coupled with LTQ orbitrap mass spectrome-tryrdquo Natural Product Communications vol 7 no 2 pp 181ndash1842012
[59] T-T Sun D-W Zhang Y Han F-Y Dong andWWang ldquoSmi-lasides M and N two new phenylpropanoid glycosides fromSmilax ripariardquo Journal of Asian Natural Products Research vol14 no 2 pp 165ndash170 2012
[60] J Li X Bi G Zheng Y Hitoshi T Ikeda and T NoharaldquoSteroidal glycosides and aromatic compounds from Smilaxripariardquo Chemical amp Pharmaceutical Bulletin vol 54 no 10 pp1451ndash1454 2006
[61] N Wang X Yao R Ishii and S Kitanaka ldquoBioactive sucroseesters from Bidens parviflorardquo Phytochemistry vol 62 no 5 pp741ndash746 2003
[62] S Nakamura K Fujimoto T Matsumoto et al ldquoAcylatedsucroses and acylated quinic acids analogs from the flower budsof Prunus mume and their inhibitory effect on melanogenesisrdquoPhytochemistry vol 92 pp 128ndash136 2013
[63] K Fujimoto SNakamura TMatsumoto et al ldquoMedicinal flow-ers XXXVIII Structures of acylated sucroses and inhibitoryeffects of constituents on aldose reducatase from the flower budsofPrunusmumerdquoChemical and Pharmaceutical Bulletin vol 61no 4 pp 445ndash451 2013
[64] S Nakamura K Fujimoto T Matsumoto et al ldquoStructuresof acylated sucroses and an acylated flavonol glycoside andinhibitory effects of constituents on aldose reductase from theflower buds of Prunus mumerdquo Journal of Natural Medicines vol67 no 4 pp 799ndash806 2013
[65] L-B Dong J He X-Y Li et al ldquoChemical constituents fromthe aerial parts of Musella lasiocarpardquo Natural Products andBioprospecting vol 1 no 1 pp 41ndash47 2011
[66] Y Xiong K Z Deng Y Q Guo W Y Gao and T J ZhangldquoNew chemical constituents from the rhizomes of Sparganiumstoloniferumrdquo Archives of Pharmacal Research vol 32 no 5 pp717ndash720 2009
[67] Y Xiong K-Z Deng Y-Q Guo W-Y Gao and T-J ZhangldquoTwo new sucrose esters from Sparganium stoloniferumrdquo Jour-nal of Asian Natural Products Research vol 10 no 5 pp 425ndash428 2008
[68] B Chen N L Wang J H Huang and X S Yao ldquoIridoidand phenylpropanoid glycosides from Scrophularia ningpoensis
22 Evidence-Based Complementary and Alternative Medicine
Hemslrdquo Asian Journal of Traditional Medicines vol 2 no 3 pp119ndash123 2007
[69] H Chen Y Z Zhou L Qiao et al ldquoTwo new compounds fromCynanchum amplexicaulerdquo Journal of Asian Natural ProductsResearch vol 10 no 3 pp 248ndash251 2008
[70] C-L Chang L-J Zhang R Y Chen et al ldquoAntioxidant andanti-inflammatory phenylpropanoid derivatives from Calamusquiquesetinerviusrdquo Journal of Natural Products vol 73 no 9 pp1482ndash1488 2010
[71] Y Kawai H Kumagai H Kurihara K Yamazaki R Sawanoand N Inoue ldquo120573-Glucosidase inhibitory activities of phenyl-propanoid glycosides vanicoside A and B from Polygonumsachalinense rhizomerdquo Fitoterapia vol 77 no 6 pp 456ndash4592006
[72] P V Kiem N X Nhiem N X Cuong et al ldquoNew phenyl-propanoid esters of sucrose from Polygonum hydropiper andtheir antioxidant activityrdquo Archives of Pharmacal Research vol31 no 11 pp 1477ndash1482 2008
[73] K J Wang Y J Zhang and C R Yang ldquoAntioxidant phenolicconstituents from Fagopyrum dibotrysrdquo Journal of Ethnophar-macology vol 99 no 2 pp 259ndash264 2005
[74] N Cho J Huh H Yang et al ldquoChemical constituentsof Polygala tenuifolia roots and their inhibitory activity onlipopolysaccharide-induced nitric oxide production in BV2microgliardquo Journal of Enzyme Inhibition and Medicinal Chem-istry vol 27 no 1 pp 1ndash4 2012
[75] Q Ren C S Wu and J L Zhang ldquoUse of on-line stop-flowheart-cutting two-dimensional high performance liquid chro-matography for simultaneous determination of 12 major con-stituents in tartary buckwheat (Fagopyrum tataricum Gaertn)rdquoJournal of Chromatography A vol 1304 pp 257ndash262 2013
[76] Q Ren C S Wu Y Ren and J L Zhang ldquoCharacterizationand identification of the chemical constituents from tartarybuckwheat (Fagopyrum tataricumGaertn) by high performanceliquid chromatographyphotodiode array detectorlinear iontrap FTICR hybrid mass spectrometryrdquo Food Chemistry vol136 no 3-4 pp 1377ndash1389 2013
[77] W Li Y N Sun X T Yan et al ldquoNF-120581B inhibitory activityof sucrose fatty acid esters and related constituents fromAstragalus membranaceusrdquo Journal of Agricultural and FoodChemistry vol 61 no 29 pp 7081ndash7088 2013
[78] J T Cheng J He Y Li et al ldquoThree new sucrose fatty acid estersfrom Equisetum hiemale LrdquoHelvetica Chimica Acta vol 95 no7 pp 1158ndash1163 2012
[79] Y Jiang and P-F Tu ldquoTenuifoliose Q a new oligosaccharideester from the root of Polygala tenuifoliaWilldrdquo Journal of AsianNatural Products Research vol 5 no 4 pp 279ndash283 2003
[80] M Yoshikawa H Matsuda T Morikawa H H Xie S Naka-mura and O Muraoka ldquoPhenylethanoid oligoglycosides andacylated oligosugars with vasorelaxant activity from Cistanchetubulosardquo Bioorganic ampMedicinal Chemistry vol 14 no 22 pp7468ndash7475 2006
[81] P-F Tu H-M Shi Z-H Song Y Jiang and Y-Y ZhaoldquoChemical constituents of Cistanche sinensisrdquo Journal of AsianNatural Products Research vol 9 no 1 pp 79ndash84 2007
[82] C-L Si Y-Y Lu P-P Qin R-C Sun and Y-H Ni ldquoPhenolicextractives with chemotaxonomic significance from the bark ofPaulownia tomentosa var tomentosardquo BioResources vol 6 no4 pp 5086ndash5098 2011
[83] J Wu S Zhang Q Xiao et al ldquoPhenylethanoid and aliphaticalcohol glycosides from Acanthus ilicifoliusrdquo Phytochemistryvol 63 no 4 pp 491ndash495 2003
[84] Y Jiang and P-F Tu ldquoAnalysis of chemical constituents inCistanche speciesrdquo Journal of Chromatography A vol 1216 no11 pp 1970ndash1979 2009
[85] H Otsuka H Kuwabara and H Hoshiyama ldquoIdentification ofsucrose diesters of aryldihydronaphthalene-type lignans fromTrigonotis peduncularisand the nature of their fluorescencerdquoJournal of Natural Products vol 71 no 7 pp 1178ndash1181 2008
[86] M-R Suo J-S Yang and Q-H Liu ldquoLignan oligosaccharideesters from Eritrichium rupestrerdquo Journal of Natural Productsvol 69 no 4 pp 682ndash684 2006
[87] P-F Tu Z-H Song H-M Shi Y Jiang and Y-Y ZhaoldquoArylethyl (=phenylethanoid) glycosides and oligosaccharidefrom the stem of Cistanche tubulosardquo Helvetica Chimica Actavol 89 no 5 pp 927ndash935 2006
[88] M-H Shyr T-H Tsai and L-C Lin ldquoRossicasins A Band rosicaside F three new phenylpropanoid glycosides fromBoschniakia rossicardquoChemical and Pharmaceutical Bulletin vol54 no 2 pp 252ndash254 2006
[89] R FangNCVeitchGCKiteM J RHowes EA Porter andM S J Simmonds ldquoGlycosylated constituents of Iris fulvaandIris brevicaulisrdquoChemical amp Pharmaceutical Bulletin vol 59 no1 pp 124ndash128 2011
[90] J Fu L Zuo J Yang R Chen and D Zhang ldquoOligosaccharidepolyester and triterpenoid saponins from the roots of Polygalajaponicardquo Phytochemistry vol 69 no 7 pp 1617ndash1624 2008
[91] M-C Cheng C-Y Li H-C Ko F-N Ko Y-L Lin andT-S Wu ldquoAntidepressant principles of the roots of polygalatenuifoliardquo Journal of Natural Products vol 69 no 9 pp 1305ndash1309 2006
[92] H T Chang and P F Tu ldquoNew oligosaccharide esters andxanthone C-glucosides from Polygala telephioidesrdquo HelveticaChimica Acta vol 90 no 5 pp 944ndash950 2007
[93] J Li L Feng J Dai R Wang and T Nohara ldquoChemical con-stituents from Polygala telephioidesrdquo China Journal of ChineseMateria Medica vol 34 no 4 pp 402ndash405 2009
[94] W-P Yin T-Z Zhao and H-Y Zhang ldquoA novel oligosaccha-ride ester from Syringa pubescensrdquo Journal of Asian NaturalProducts Research vol 10 no 1 pp 95ndash100 2008
[95] M Valko D Leibfritz J Moncol M T D Cronin M Mazurand J Telser ldquoFree radicals and antioxidants in normal physio-logical functions and human diseaserdquoThe International Journalof Biochemistry amp Cell Biology vol 39 no 1 pp 44ndash84 2007
[96] D Krishnaiah R Sarbatly and R Nithyanandam ldquoA review ofthe antioxidant potential of medicinal plant speciesrdquo Food andBioproducts Processing vol 89 no 3 pp 217ndash233 2011
[97] P Liu Y Hu D-H Guo et al ldquoAntioxidant activity ofoligosaccharide ester extracted from Polygala tenuifolia roots insenescence-accelerated micerdquo Pharmaceutical Biology vol 48no 7 pp 828ndash833 2010
[98] Y Hu H-B Liao G Dai-Hong P Liu Y-Y Wang and KRahman ldquoAntidepressant-like effects of 361015840-disinapoyl sucroseon hippocampal neuronal plasticity and neurotrophic signalpathway in chronically mild stressed ratsrdquo NeurochemistryInternational vol 56 no 3 pp 461ndash465 2010
[99] Y Hu H B O Liao P Liu D-H Guo and K RahmanldquoA bioactive compound from Polygala tenuifolia regulatesefficiency of chronic stress on hypothalamic-pituitary-adrenalaxisrdquo Pharmazie vol 64 no 9 pp 605ndash608 2009
[100] A Jungbauer and SMedjakovic ldquoAnti-inflammatory propertiesof culinary herbs and spices that ameliorate the effects ofmetabolic syndromerdquoMaturitas vol 71 no 3 pp 227ndash239 2012
Evidence-Based Complementary and Alternative Medicine 23
[101] Q Xu Y Wang S Guo Z Shen and L Yang ldquoAnti-inflammatory and analgesic activity of aqueous extract of Flospopulirdquo Journal of Ethnopharmacology vol 152 no 3 pp 540ndash545 2014
[102] K S Kim D S Lee G S Bae et al ldquoThe inhibition of JNKMAPK and NF-120581B signaling by tenuifoliside A isolated fromPolygala tenuifolia in lipopolysaccharide-induced macrophagesis associated with its anti-inflammatory effectrdquo European Jour-nal of Pharmacology vol 721 no 1ndash3 pp 267ndash276 2013
[103] J-G Lee J-M Yon C Lin A Y Jung K Y Jung and S-YNamldquoCombined treatment with capsaicin and resveratrol enhancesneuroprotection against glutamate-induced toxicity in mousecerebral cortical neuronsrdquo Food and Chemical Toxicology vol50 no 11 pp 3877ndash3885 2012
[104] M L Jin S Y Park Y H Kim J-I Oh S J Lee andG Park ldquoThe neuroprotective effects of cordycepin inhibitglutamate-induced oxidative andER stress-associated apoptosisin hippocampal HT22 cellsrdquo NeuroToxicology vol 41 pp 102ndash111 2014
[105] P Liu Y Hu J Li et al ldquoProtection of SH-SY5Y neuronal cellsfrom glutamate-induced apoptosis by 36rsquo-disinapoyl sucrosea bioactive compound isolated from radix polygalardquo Journal ofBiomedicine and Biotechnology vol 2012 Article ID 728342 5pages 2012
[106] P-B Li W-L Lin Y-G Wang W Peng X-Y Cai and W-WSu ldquoAntidiabetic activities of oligosaccharides of Ophiopogonisjaponicus in experimental type 2 diabetic ratsrdquo InternationalJournal of Biological Macromolecules vol 51 no 5 pp 749ndash7552012
[107] T Liu Y M Yip L Song et al ldquoInhibiting enzymatic starchdigestion by the phenolic compound diboside A a mechanisticand in silico studyrdquo Food Research International vol 54 no 1pp 595ndash600 2013
[108] F Cote andMGHahn ldquoOligosaccharins structures and signaltransductionrdquo Plant Molecular Biology vol 26 no 5 pp 1379ndash1411 1994
[109] RACreelman and J EMullet ldquoOligosaccharins brassinolidesand jasmonates nontraditional regulators of plant growthdevelopment and gene expressionrdquo Plant Cell vol 9 no 7 pp1211ndash1223 1997
[110] L Jiao D Wan X Zhang B Li H Zhao and S LiuldquoCharacterization and immunostimulating effects on murineperitoneal macrophages of oligosaccharide isolated from Panaxginseng CAMeyerrdquo Journal of Ethnopharmacology vol 144 no3 pp 490ndash496 2012
Submit your manuscripts athttpwwwhindawicom
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Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
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Disease Markers
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
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OncologyJournal of
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Oxidative Medicine and Cellular Longevity
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PPAR Research
The Scientific World JournalHindawi Publishing Corporation httpwwwhindawicom Volume 2014
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Computational and Mathematical Methods in Medicine
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Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Parkinsonrsquos Disease
Evidence-Based Complementary and Alternative Medicine
Volume 2014Hindawi Publishing Corporationhttpwwwhindawicom
2 Evidence-Based Complementary and Alternative Medicine
Orobanchaceae Acanthaceae Rosaceae Musaceae Spargan-iaceae Leguminosae Equisetaceae Boraginaceae IridaceaeAlismataceae Lamiaceae Araliaceae Rubiaceae OleaceaeApocynaceae Caryophyllaceae Aspleniaceae and Trilliaceaeare rich in oligosaccharides and their esters Oligosaccharidesshow diversified structures because of the type and thenumber of monosaccharides as well as the positionof glycosidic bonds And oligosaccharide esters alsodisplay distinctive structural diversity largely owing to thenumber type and position of O-substituent units includingphenylpropanoid groups (eg coumaroyl feruloyl caffeoylsinapoyl 345-trimethoxycinnamoyl and cinnamoyl)benzoyl p-methoxybenzoyl and p-hydroxybenzoyl groups(Figure 2) Moreover the double bonds of phenylpropanoidgroups possess trans and cis isomeric forms of which thetrans forms widely exist in nature Hence according tothe number of monosaccharides and the characteristics ofchemical structures these oligosaccharide esters could becategorized into 7 large groups
21 Oligosaccharides All compounds of this group (Table 1and Figure 1) merely consist of various monosaccharideswithout O-substituents In addition to the well-knownsucrose 120573-D-glucopyranosyl(1rarr 2)-120573-D-glucopyranoside(1) was isolated from Camptosorus sibiricus [12] Theoligosaccharides of raffinose (3) stachyose (19) andverbascose (21) all of which belong to the Raffinose familypossess one two or three galactopyranosyl units linked tosucrose and have been found in the rhizomes and rootsof Alisma orientalis [13] Lycopus lucidus [14] Rehmanniaglutinosa [15 16] Salvia miltiorrhiza [17] and Scrophularianingpoensis [18] Manninotriose (4) and verbascotetraose (5)consisting of galactopyranosyl units and a glucopyranosylunit have been isolated from Alisma orientalis [13]
Five oligosaccharides comprising 1-kestose (6) nystose(7) 1-120573-fructofuranosylnystose (8) hexasaccharide (9) andheptasaccharide (10) consisting of fructofuranose and glu-copyranose have been isolated from the aerial parts and rootsof Gynura divaricata subsp formosana [19] Morinda offici-nalis [20ndash22] Saussurea lappa [23] and Aralia cordata [24]Two water-soluble oligosaccharides (11 12) composed of twoor three types of monosaccharides including glucopyranosefructopyranose and fructofuranose have been obtained fromthe whole plants of Blumea riparia [25 26]
Besides malto-oligosaccharides (17 119899 = 0sim8) consist-ing of 120572-D-glucopyranosyl residues assembled by (1rarr 4)-linkages and inulo-oligosaccharides (18 119899= 1sim3) consisting ofonly fructosyl residues formed by (2rarr 1)-linkages have beenfound in the roots of Panax ginseng [27 28] and Morindaofficinalis [20] respectively Three noteworthy oligosaccha-rides (2 13 14) formed by 120572-D-glucopyranosyl units with(1rarr 6)-linkages and a (1rarr 4)-linkage have been found in theroots of Panax ginseng [28] And two linear oligosaccharidestermed heptasaccharide (15) and octasaccharide (16) consist-ing of glucose and mannose monomers were identified fromthe rhizomes of Paris polyphylla var yunnanensis [29 30]A pentasaccharide stellariose (20) consisting of a raffinosebackbone with two galactosyl residues bound to the fructosyl
and glucosyl moieties was identified from the stems ofStellaria media [31]
Oligosaccharides (Table 1) are composed of seven kindsof deoxyhexoses including cymaropyranose canaropyra-nose digitoxopyranose oleandropyranose digitalopyranosecymaropyranurolactone and oleandronic acid-120575-lactoneOleandronic acid-120575-lactone exhibits the boat and chair con-formations The hydroxyl methyl and acetyl groups arelocated at the equatorial (e) and axial (a) bonds in the chairconformation of deoxyhexoses These oligosaccharides wereisolated from the traditional Chinesemedicines including theroots of Periploca forrestii the root barks of P sepium thestems of P calophylla and the barks of Parabarium huaitingii
22 Oligosaccharide Esters
221 Phenylpropanoid-Derived Disaccharide Esters Phenyl-propanoid-derived disaccharide esters (Table 2 and Figure 3)account for a considerable proportion of oligosaccharideesters and mainly possess a core of sucrose carryinga varying number of O-substituents including phenyl-propanoid groups acetyl benzoyl p-methoxybenzoyl andp-hydroxybenzoyl groups Phenylpropanoid substituents arejust present at 11015840 31015840 41015840 61015840 positions of 120573-D-fructofuranosylunit in compounds 35ndash97 whereas they appear at 2 3 46 positions of 120572-D-glucopyranosyl moiety in compounds98ndash101 Moreover compounds 76ndash97 are mainly esterifiedwith acetyl groups along with a phenylpropanoid sub-stituent coumaroyl feruloyl or 345-trimethoxycinnamoylgroup Interestingly the phenylpropanoid substituents areonly attached to the 31015840 position of sucrose The twosugar rings of compounds 102ndash128 both possess phenyl-propanoid substituents These oligosaccharide esters havebeen found in the roots and rhizomes of Polygala tricornisP tenuifolia Fagopyrum tataricum Scrophularia ningpoensisCynanchum amplexicaule Smilax riparia Paris polyphyllavar yunnanensis Smilacis glabrae Fagopyrum dibotrys andSparganium stoloniferum the underground parts of Tril-lium kamtschaticum the stems of Polygonum sachalinensisP cuspidatum P hydropiper Smilax china and Calamusquiquesetinervius the aerial parts of Polygala sibirica Smilaxbracteata Heterosmilax erythrantha and Musella lasiocarpathe leaves of Persicaria hydropiper and Polygonum hydropiperthe whole plants of Bidens parviflora and Polygala hongkon-gensis and the flower buds of Prunus mume
Cistanoside F (129) has been found in the stems ofCistanche tubulosa [80] and C sinensis [81] the barks of Pau-lownia tomentosa var tomentosa [82] and the aerial partsof Acanthus ilicifolius [83] Cistanoside I (130) has alsobeen isolated from the stems of the Cistanche plants [84]Both of them are composed of glucosyl and rhamnosylgroups connected by a 1rarr 3 glycosidic bond In addi-tion 661015840-sucrose ester of (1120572212057231205734120573)-34-bis(4-hydroxy-phenyl)-12-cyclobutanedicarboxylic acid (131) with a bis(4-hydroxyphenyl) cyclobutanedicarboxyl group as the acyl unitin the molecule structure was isolated from the whole plantsof Bidens parviflora [61]
Evidence-Based Complementary and Alternative Medicine 3
Table1Oligosaccharides
No
Nam
eR 1
R 2R 3
R 4R 5
R 6Source
Parts
Reference
22PerifosaccharideA
OH(e)
OCH
3(e)
HOH(e)
OH
APerip
loca
forrestii
Roots
[32]
23PerifosaccharideB
OH(e)
OCH
3(a)
HOH(e)
OH
APerip
loca
forrestii
Roots
[32]
24PerifosaccharideC
OH(e)
OCH
3(e)
HOH(e)
OCH
3A
Perip
loca
forrestii
Roots
[32]
25PerifosaccharideD
OAc
(e)
OCH
3(e)
HOH(e)
OH
APerip
loca
forrestii
Roots
[32]
26Peris
accharideA
OH(a)
OCH
3(e)
OAc
OH(e)
OCH
3A
Perip
loca
sepium
Root
barks
[33]
27Peris
accharideB
OAc
(e)
OCH
3(a)
HOH(e)
OH
APerip
loca
sepium
Perip
loca
calophylla
Root
barks
[3334]
28Peris
accharideC
OH(a)
OCH
3(e)
OAc
OCH
3(a)
OH
APerip
loca
sepium
Root
barks
[33]
29Peris
accharideD
OAc
(e)
OCH
3(a)
HOH(e)
OCH
3A
Perip
loca
calophylla
Stem
s[34]
30Peris
esaccharideB
OH(a)
OCH
3(e)
OAc
OH(e)
OCH
3C
Perip
loca
sepium
Root
barks
[35]
31Peris
esaccharideC
OH(a)
OCH
3(e)
OH
OCH
3(a)
OCH
3C
Perip
loca
sepium
Root
barks
[35]
32Peris
esaccharideD
OH(a)
OCH
3(e)
OH
OCH
3(a)
OH
CPerip
loca
sepium
Root
barks
[35]
33Peris
esaccharideE
OH(a)
OCH
3(e)
OAc
OH(e)
OH
CPerip
loca
sepium
Root
barks
[35]
34
Cymarop
yranurolactone
4-O-120573-D
-digita
lopyrano
syl-
(1rarr4)-O
-120573-D
-cymarop
yranosyl-(1rarr4)-O
-120573-
D-oleandrop
yranosyl-(1rarr4)-
O-120573-D
-cym
arop
yranoside
OH(a)
OCH
3(e)
OH
OCH
3(e)
OCH
3B
Parabariu
mhu
aitin
gii
Barks
[36]
SeeS
chem
e1
4 Evidence-Based Complementary and Alternative Medicine
R1
R2 R3
R4
R5
R6
O OO
OO
O
O
OO
O O OO
O
O
O
OCH3
H3COH3CO
H3CO
A oleandronic acid-120575-lactone B cymaropyranurolactone C oleandronic acid-120575-lactone
Scheme 1
222 Fatty Acid-Derived Disaccharide Esters Eight mono-substituted disaccharide esters (Table 3) with a sucrose moi-ety possess six different types of fatty acid residues whichattach to the 6 or 61015840 position of sucrose These fatty acidsinclude linoleic acid palmitic acid linolenic acid myris-tic acid hexadeca-71013-trienoic acid and hexadeca-710-dienoic acid The above sucrose fatty acid esters have beenfound in the rhizomes of Astragalus membranaceus and theroots of Equisetum hiemale
223 Lignan-DerivedDisaccharide Esters Six lignan-deriveddisaccharide esters (Figure 4) contain a sucrose core esterifiedwith different lignan residues covalently linked to the 31015840and 61015840 positions of 120573-D-fructofuranosyl unit and have beenisolated from the whole parts of Trigonotis peduncularis [85]and the aerial parts of Eritrichium rupestre [86]
224 Phenylpropanoid-Derived Trisaccharide Esters Inthis group all oligosaccharide esters consist of threemonosaccharides including glucopyranose fructofuranoseand rhamnopyranose with O-substituents which compriseferuloyl sinapoyl and 345-trimethoxycinnamoyl groupsOligosaccharide esters (146ndash149) listed in Table 4 as well askankanose (150) cistantubulose A
1A2(151) cistansinensose
A1A2(152) and compound 153 shown in Figure 5 have
been found in the roots of Polygala tricornis [37] the stemsof Cistanche tubulosa [81 87] and C sinensis [80] the wholeparts of Boschniakia rossica [88] and the rhizomes of Irisbrevicaulis [89]
225 Phenylpropanoid-Derived Tetrasaccharide Esters Phe-nylpropanoid-derived tetrasaccharide esters (154ndash159)(Table 5) consisting of three glucopyranosyl units and afructofuranosyl unit have been identified from the rootsof Polygala tricornis The nonsugar moieties of theseoligosaccharides include coumaroyl feruloyl sinapoyl and345-trimethoxycinnamoyl groups
226 Phenylpropanoid-Derived Pentasaccharide Esters Asshown in Table 6 oligosaccharide esters (160-179) possess-ing a skeleton of five sugar residues have been isolatedfrom the roots of Polygala tenuifolia The sugar residues
are composed of two types of monosaccharides includ-ing fructofuranose and glucopyranose which are esterifiedwith acetyl benzoyl rhamnose-substitutednonsubstitutedcoumaroyl and rhamnose-substitutednonsubstituted feru-loyl groups Other than that a structure-complex oligosac-charide polyester shown in Figure 5 polygalajaponicose I(180) consisting of a pentasaccharide backbone esterifiedwith feruloyl coumaroyl rhamnosyl-coumaroyl acetyl andbenzoyl groups has been obtained from the roots of Pjaponica [90]
227 Others Polygalatenosides AndashC (181ndash183) (Figure 6)containing a galactosyl unit and a polygolitosyl unit esterifiedwith benzoyl groups at 3 4 and 6 positions have been foundin the roots of Polygala tenuifolia [91] Three sucrose estersincluding polygalatenoside D (190) telephiose F (191) and6-O-benzoylsucrose (192) possess one benzoyl group twobenzoyl groups and a p-methoxybenzoyl group respectivelyThey were isolated from the roots of P tenuifolia [91] thewhole plants of P telephioides [92] and the roots of P tricornis[37] Six trisaccharide esters named telephioses AndashE and G(184ndash189) with substituents of acetyl and benzoyl groupswere isolated from the whole plants of P telephioides [92 93]Moreover a trisaccharide ester (193) pubescenside A fromthe flowers of Syringa pubescens possesses a fatty acid residue[94]
3 Biological Activities ofOligosaccharides and Their Esters
The oligosaccharides and oligosaccharide esters from Chi-nese medicinal plants are important products with diver-sified structures which have triggered an increasing num-ber of studies carried out on the isolated compoundsAnd thus diverse pharmacological activities have beenproved Among the isolated compounds oligosaccharidesphenylpropanoid-derived disaccharide esters and trisaccha-ride esters fatty acid-derived disaccharide esters and othersfrom the families Polygonaceae Asclepiadaceae RubiaceaePolygalaceae Liliaceae Smilacaceae Arecaceae Oroban-chaceae Scrophulariaceae Acanthaceae Rosaceae Sparga-niaceae Leguminosae and Equisetaceae have shown sig-nificant pharmacological activities including antioxidant
Evidence-Based Complementary and Alternative Medicine 5
1 2 3 4
5 6 7 8
9 10 11 12
13 14 15
16 17
OHOH
OH
OHOH
OHOH
OH
OHOH
OH
OO
O
OOO
HOHO
HO
HOHO CH2OH
CH2OH
CH2
2
2
3
4 5
5
66
6n
OH
OH
OH
OH
OHO O
O
OO
HO
HO
HO HO
HO
HO
OH
OHO OHO
HO OHO OHO
HO OHO
HOHO
OH
OH
OH
OH
OHOH
OHO OHO
HO OHO OHO
HO OHO
O
OO
OO
HO
HOHO
HOHO
HOHO
OHCH2OH
CH2
OH
OH
OH
OHO
OO
OO
HOHO HO
HOHO
HOHO
2
CH2OH
CH2
OH
OH
OH
OHO
OO
OO
HO
HOHO
HOHO
CH2OH
CH2
OH
OH
OH
OHO
OO
OO
HO
HOHO HO
HOHO
CH2OH
CH2
OH
OH
OH
OHO
OO
OO
HO
HO
HO HO
HOHO
CH2OH
CH2
OH
OH
OH
OHO
OO
OO
HO
HOHO HO
HOHO
CH2
OH
OH
OH OH
OHO
OO
OO
HO
HOHO HO
HOHO
OH
OH
OHOH
OH
OH
O
OO
O
OHO
HO
HOHO
HO
OH
OH
OH OHOH
OH
O
OO
O
OHO
HO
HOHO
HO
OH
OH OH
OH
OH
OH
OO
O O
O
HOHO HO
HO
HO
OH
OH OH
OH
OH
OO
O O
O
HOHO HO
HO
HOHO OH
OH
OH OHOH
OH
O
OO
O
O
HOHO
HO
HO
HO
Figure 1 Continued
6 Evidence-Based Complementary and Alternative Medicine
18 19
20 21
2
n
OH
OH
H
OH
OH
OH
OH
OO
O
O
O
HO
HOHO
HO
HO
CH2OH
OH
OHO OHO
HO OHO OHO
HO OH
OH
O
OO
HO
HOHO
HO
CH2OH
OH
OHO OHO
HO OHO OHO
HO OH
OH
O
OO
HO
HOHO
OH
OH
OHOHO
HO
OH
OH
OH
OH
OH
OHO
O
O
O
O
O
O
HO
HO
HO
OH
OH
OH
OH O
Figure 1
D benzoyl E p-methoxybenzoyl F p-hydroxybenzoyl G coumaroyl
I feruloyl J caffeoyl K sinapoyl
L 345-trimethoxycinnamoyl M cinnamoyl
O
O
O
O O O
OO
O
OCH3
OCH3
OCH3
OCH3
OCH3
OCH3
OCH3
OH
OHOH
OHOHOH
Figure 2
Evidence-Based Complementary and Alternative Medicine 7
Table2Ph
enylprop
anoid-deriv
eddisaccharid
eeste
rs
Num
ber
Nam
eR 1
R 2R 3
R 4R 5
R 6R 7
R 8Source
Parts
Reference
35Sibiric
oseA
6H
HH
HK
HH
HPolyg
alatricornis
Polyg
alatenu
ifolia
Roots
Root
barks
[37ndash40
]
3631015840-O
-FeruloylsucroseSibiricose
A5
HH
HH
IH
HH
Polyg
alatenu
ifolia
Trillium
kamtsc
haticum
Roots
Und
ergrou
ndparts
[38ndash42]
37GlomeratoseA
HH
HH
LH
HH
Polyg
alatricornis
Roots
[37]
38LapathosideD
HH
HH
GG
HH
Polyg
onum
sachalinense
Stem
s[43]
39Helo
niosideA
HH
HH
II
HH
Trillium
kamtsc
haticum
Smila
xbracteata
Paris
polyphylla
varyunn
anensis
Und
ergrou
ndparts
Aeria
lparts
Roots
[4144
45]
40Helo
niosideB
AcH
HH
II
HH
Smila
xbracteata
Smila
xchina
Smila
xrip
aria
Heterosmila
xerythrantha
Aeria
lparts
Stem
sRo
otsa
ndrhizom
es
[4446
ndash48]
41Paris
polysid
eFH
HH
HG
IH
HPa
risPolyphylla
varyunn
anensis
Rhizom
es[4950]
42Hydropiperosid
eH
HH
HG
GH
GPolyg
onum
sachalinense
Polyg
onum
cuspidatum
Persica
riahydropiper
Stem
sLeaves
[435152]
43Tricorno
seB
DAc
HH
LH
HH
Polyg
alatricornis
Roots
[37]
44Tenu
ifolisideA
FH
HH
LH
HH
Polyg
alatenu
ifolia
Polygalahongkongensis
Polyg
alasib
irica
Roots
Who
leplants
Aeria
lparts
[3840
4253ndash
56]
45Tataris
ideA
AcH
HAc
GG
HAc
Fagopyrum
tataric
umRo
ots
[57]
46Tataris
ideE
HH
HAc
GG
HAc
Fagopyrum
tataric
umRo
ots
[57]
47Tataris
ideG
HH
HH
IG
HG
Fagopyrum
tataric
umRo
ots
[57]
48Sm
iglasid
eAAc
AcH
AcI
IH
ISm
ilaxrip
aria
Rootsa
ndrhizom
es[47]
49Sm
iglasid
eBAc
HH
AcI
IH
ISm
ilaxrip
aria
Rootsa
ndrhizom
es[47]
50Sm
iglasid
eEAc
HH
AcI
IH
GSm
ilaxchina
Stem
s[46]
51Sm
ilasid
eAAc
AcH
HI
IH
HSm
ilaxchina
Stem
s[46]
52Sm
ilasid
eBH
HH
AcI
IH
HSm
ilaxchina
Stem
s[46]
53Sm
ilasid
eCH
HH
HI
IH
GSm
ilaxchina
Stem
s[46]
54Sm
ilasid
eDH
HH
HI
IAc
GSm
ilaxchina
Stem
s[46]
8 Evidence-Based Complementary and Alternative Medicine
Table2Con
tinued
Num
ber
Nam
eR 1
R 2R 3
R 4R 5
R 6R 7
R 8Source
Parts
Reference
55Sm
ilasid
eEAc
HH
HI
IH
GSm
ilaxbracteata
Smila
xchina
Aeria
lparts
Stem
s[4446
]
56Sm
ilasid
eFAc
HH
AcG
IH
GSm
ilaxchina
Stem
s[46]
57Sm
ilasid
eGH
HH
HG
IH
GSm
ilaxbracteata
Smilacis
glabrae
Aeria
lparts
Rhizom
es[4458]
58Sm
ilasid
eHH
HH
AcG
IH
GSm
ilaxbracteata
Aeria
lparts
[44]
59Sm
ilasid
eIAc
HH
HG
IH
GSm
ilaxbracteata
Aeria
lparts
[44]
60Sm
ilasid
eJH
HH
HG
IH
ISm
ilaxbracteata
Smilacis
glabrae
Aeria
lparts
Rhizom
es[4458]
61Sm
ilasid
eKH
HH
AcI
IH
GSm
ilaxbracteata
Aeria
lparts
[44]
62Sm
ilasid
eLH
HH
HI
IH
ISm
ilaxbracteata
Smilacis
glabrae
Aeria
lparts
Rhizom
es[4458]
63Sm
ilasid
eMAc
HH
AcCis-feruloyl
IH
HSm
ilaxrip
aria
Rootsa
ndrhizom
es[59]
64Sm
ilasid
eNAc
HH
AcI
Cis-
feruloyl
HH
Smila
xrip
aria
Rootsa
ndrhizom
es[59]
65Sm
ilasid
ePH
HH
AcI
IH
ISm
ilaxrip
aria
Rootsa
ndrhizom
es[47]
66310158404101584061015840-O
-Tri-
feruloylsucrose
HH
HH
II
IH
Smila
xrip
aria
Rhizom
esand
roots
[60]
6761015840-O
-Cou
maroylsu
crose
HH
HH
HG
HH
Bidens
parviflora
Who
leplants
[61]
6811015840 -O-C
oumaroyl-61015840-O
-feruloylsucrose
HH
HH
HI
HG
Smila
xbracteata
Aeria
lparts
[44]
694-O-Benzoyl-31015840-345-
trim
etho
xycinn
amoylsu
crose
HD
HH
LH
HH
Polyg
alatricornis
Roots
[37]
706-O-Benzoyl-31015840-O
-345-
trim
etho
xycinn
amoylsu
crose
DH
HH
LH
HH
Polyg
alatricornis
Roots
[37]
716-O-Benzoyl-31015840-O
-sin
apoylsu
crose
DH
HH
KH
HH
Polyg
alatricornis
Roots
[37]
726-O-p-M
etho
xybenzoyl-31015840-O
-345-
trim
etho
xycinn
amoylsu
crose
EH
HH
LH
HH
Polyg
alatenu
ifolia
Roots
[56]
7326-Di-a
cetyl-3101584061015840-di-
feruloylsucrose
AcH
HAc
II
HH
Smila
xchina
Smila
xrip
aria
Heterosmila
xerythrantha
Stem
sRo
otsa
ndrhizom
esAe
rialp
arts
[46ndash
4859]
7426-Di-a
cetyl-31015840-O
-cis-feruloy-
61015840-tr
ans-feruloylsucrose
AcH
HAc
Cis-feruloy
IH
HSm
ilaxrip
aria
Rootsa
ndrhizom
es[59]
Evidence-Based Complementary and Alternative Medicine 9
Table2Con
tinued
Num
ber
Nam
eR 1
R 2R 3
R 4R 5
R 6R 7
R 8Source
Parts
Reference
7526-Di-a
cetyl-31015840-O
-tran
s-feruloy-
61015840-cis-feruloylsucrose
AcH
HAc
ICis-
feruloyl
HH
Smila
xrip
aria
Rootsa
ndrhizom
es[59]
76Re
galosid
eAAc
HH
HI
HH
HTrillium
kamtsc
haticum
Und
ergrou
ndparts
[41]
77Tricorno
seA
AcH
HH
LH
HH
Polyg
alatricornis
Roots
[37]
78Mum
eose
AH
HH
AcG
HH
HPrun
usmum
eFlow
erbu
ds[6263]
79Mum
eose
BAc
HAc
HG
HH
HPrun
usmum
eFlow
erbu
ds[6263]
80Mum
eose
CAc
HAc
AcG
HH
HPrun
usmum
eFlow
erbu
ds[6263]
81Mum
eose
DAc
AcAc
AcG
HH
AcPrun
usmum
eFlow
erbu
ds[6263]
82Mum
eose
EAc
AcAc
AcCis-
coum
aroyl
HH
AcPrun
usmum
eFlow
erbu
ds[6263]
83Mum
eose
FAc
AcAc
HG
HH
HPrun
usmum
eFlow
erbu
ds[63]
84Mum
eose
GAc
HAc
HG
HAc
HPrun
usmum
eFlow
erbu
ds[63]
85Mum
eose
HH
HAc
AcG
HAc
HPrun
usmum
eFlow
erbu
ds[63]
86Mum
eose
IAc
AcAc
HG
AcH
HPrun
usmum
eFlow
erbu
ds[63]
87Mum
eose
JAc
AcAc
AcG
HAc
AcPrun
usmum
eFlow
erbu
ds[63 ]
88Mum
eose
KH
HAc
AcG
HH
HPrun
usmum
eFlow
erbu
ds[64]
89Mum
eose
LAc
HAc
AcG
HAc
HPrun
usmum
eFlow
erbu
ds[64]
90Mum
eose
MAc
AcAc
HG
HAc
AcPrun
usmum
eFlow
erbu
ds[64]
91Mum
eose
NAc
AcAc
HG
AcAc
HPrun
usmum
eFlow
erbu
ds[64]
92Mum
eose
OAc
HAc
AcG
HAc
AcPrun
usmum
eFlow
erbu
ds[64]
9311015840 2346-O-Penta-acetyl-31015840-O
-tra
ns-cou
maroylsu
crose
AcAc
AcAc
GH
HAc
Musellalasio
carpa
Aeria
lparts
[65]
9411015840 2346-O-Penta-acetyl-31015840-O
-cis-cou
maroylsu
crose
AcAc
AcAc
Cis-
coum
aroyl
HH
AcMusellalasio
carpa
Aeria
lparts
[65]
9511015840 236-O-Tetra-acetyl-31015840-O
-cis-
feruloylsucrose
AcH
AcAc
Cis-feruloyl
HH
AcSparganium
stolonifer
umRh
izom
es[66]
9611015840 246-O-Tetra-acetyl-31015840-O
-tra
ns-fe
ruloylsucrose
AcAc
HAc
IH
HAc
Sparganium
stolonifer
umRh
izom
es[66]
9711015840 236-O-Tetra-acetyl-31015840-O
-tra
ns-fe
ruloylsucrose
AcH
AcAc
IH
HAc
Sparganium
stolonifer
umRh
izom
es[67]
98Sibirio
sideA
MH
HH
HH
HH
Scrophularianingpoensis
Roots
[68]
99SibricoseA
1K
HH
HH
HH
HCy
nanchu
mam
plexica
ule
Roots
[69]
100
6-O-C
affeoylsucrose
JH
HH
HH
HH
Scrophularianingpoensis
Roots
[68]
101
Acretosid
eI
HH
HH
HH
HScrophularianingpoensis
Roots
[68]
10 Evidence-Based Complementary and Alternative Medicine
Table2Con
tinued
Num
ber
Nam
eR 1
R 2R 3
R 4R 5
R 6R 7
R 8Source
Parts
Reference
102
Tenu
ifolisideB
FH
HH
KH
HH
Polyg
alatenu
ifolia
Roots
[4256]
103
Tenu
ifolisideC
KH
HH
LH
HH
Polyg
alatricornis
Polyg
alatenu
ifolia
Roots
[374256]
104
Heterosmilasid
eH
HI
HH
IH
HHeterosmila
xerythrantha
Aeria
lparts
[48]
105
Quiqu
esetinerviusideA
HI
HH
II
HH
Calamus
quiquesetin
ervius
Stem
s[70]
106
Quiqu
esetinerviusideB
AcI
HH
II
HH
Calamus
quiquesetin
ervius
Stem
s[70]
107
Quiqu
esetinerviusideC
HI
HAc
II
HH
Calamus
quiquesetin
ervius
Stem
s[70]
108
Quiqu
esetinerviusideD
AcG
HH
II
HH
Calamus
quiquesetin
ervius
Stem
s[70]
109
Quiqu
esetinerviusideE
HG
HAc
II
HH
Calamus
quiquesetin
ervius
Stem
s[70]
110
Vanicosid
eAI
HH
AcG
GH
G
Polyg
onum
sachalinensis
Polyg
onum
cuspidatum
Polyg
onum
hydropiper
Stem
sLeaves
Rhizom
es[51527172]
111
Vanicosid
eBI
HH
HG
GH
G
Polyg
onum
sachalinensis
Polyg
onum
cuspidatum
Persica
riahydropiper
Stem
sLeaves
Rhizom
es[4351527172]
112
Vanicosid
eDG
HH
HG
GH
GPersica
riahydropiper
Leaves
[51]
113
Vanicosid
eEI
AcH
AcG
GH
GPolyg
onum
hydropiper
Stem
sand
leaves
[72]
114
LapathosideA
IH
HH
GG
HI
Polyg
onum
sachalinensis
Polyg
onum
cuspidatum
Fagopyrum
dibotrys
Stem
sRh
izom
es[5173]
115
LapathosideC
IH
HH
GG
HH
Polyg
onum
sachalinensis
Polyg
onum
cuspidatum
Stem
s[4352]
116
DibosideA
GH
HH
GI
HG
Fagopyrum
tataric
umFagopyrum
dibotrys
Roots
Rhizom
es[57]
117
Hidropiperosid
eAI
HH
HH
GH
GPolyg
onum
hydropiper
Stem
sand
leaves
[72]
118
Hidropiperosid
eBI
HH
AcG
GH
IPolyg
onum
hydropiper
Stem
sand
leaves
[72]
119
Tataris
ideB
IH
HAc
GG
HAc
Fagopyrum
tataric
umRo
ots
[57]
Evidence-Based Complementary and Alternative Medicine 11
Table2Con
tinued
Num
ber
Nam
eR 1
R 2R 3
R 4R 5
R 6R 7
R 8Source
Parts
Reference
120
Tataris
ideC
IAc
HAc
GG
HAc
Fagopyrum
tataric
umRo
ots
[57]
121
Tataris
ideD
GH
HAc
GI
HH
Fagopyrum
tataric
umRo
ots
[57]
122
Tataris
ideF
GH
HH
II
HG
Fagopyrum
tataric
umRo
ots
[57]
123
310158406-O
-Di-sinapoylsu
crose
KH
HH
KH
HH
Polyg
alatricornis
Polygalahongkongensis
Polyg
alasib
irica
Polyg
alatenu
ifolia
Cynanchu
mam
plexica
ule
Roots
Root
barks
Who
leplants
Aeria
lparts
[37ndash394153ndash
566974]
124
661015840-O
-Di-c
oumaroylsu
crose
GH
HH
HG
HH
Bidens
parviflora
Who
leplants
[61]
125
11015840 3101584061015840-O
-Tri-
coum
aroyl-6
-feruloylsucrose
IH
HH
GG
HG
Fagopyrum
tataric
umRo
ots
[7576]
126
3101584061015840-O
-Di-c
oumaroyl-110158406-O
-di-
feruloylsucrose
IH
HH
GG
HI
Fagopyrum
tataric
umRo
ots
[7576]
127
31015840-O
-Cou
maroyl-11015840610158406-O
-tri-
feruloylsucrose
IH
HH
IG
HI
Fagopyrum
tataric
umRo
ots
[7576]
128
11015840 31015840610158406-O
-Tetra-fe
ruloylsucrose
IH
HH
II
HI
Fagopyrum
tataric
umRo
ots
[7576]
SeeS
chem
e2
12 Evidence-Based Complementary and Alternative Medicine
131130129
CH2OHOH
OH
OO
OH
C
C
HH
HHO
OO
O
HO
HOHO
HO
HOOH
OHOHOH
OHOH
HOO
O
O
O
HO
HO
OH
OHOHOH
OHOH
HOO
O
O
O
HO
Figure 3
12
3
4
5
6
1998400
2998400
3998400
4998400
5998400
6998400
HO
O
O
R1O
R2O
R8O
R7OOR3
OR4 OR5OR6
Scheme 2
antidepressant cytotoxic antineoplastic anti-inflammatoryantidiabetic plant growth-regulatory neuroprotective andcerebral protective activities Lignan-derived disaccharideesters phenylpropanoid-derived tetrasaccharide esters andpentasaccharide esterswith biological activities have not beenreported Aside from the isolated constituents oligosaccha-ride mixtures from Rehmannia glutinosa Panax ginseng andScrophularia ningpoensiswere also reported to display diversepharmacological activities such as antidiabetic immunopo-tentiating enhanced memory and antineoplastic activitiesThese active compounds and mixtures could serve as thevaluable candidates to be developed as possible drugs for thetreatment and prevention of diseases
31 Antioxidant Activity The adverse effects of oxidativestress proposed to play significant roles in the pathogenesis ofcardiovascular diseases atherosclerosis hypertension can-cer diabetes mellitus neurodegenerative diseases rheuma-toid arthritis ischemiareperfusion injury and ageing havebecome an inevitable and serious issue [95 96] Scientistshave thus made great efforts to explore antioxidants frommedicinal plants by using different kinds of assay methodswhich include DPPH radical scavenging assay hydroxylradical scavenging assay superoxide anion scavenging assayand ABTS radical scavenging method [96]
Lapathosides C and D hydropiperoside vanicoside Bhidropiperosides A and B lapathoside A and diboside Awere isolated from the Polygonum Persicaria and Fagopyrumgenera belonging to the Polygonaceae family The DPPH testrevealed that free radical-scavenging activity of the isolatedcompounds termed lapathoside C (115) hydropiperoside(42) vanicoside B (111) and lapathoside D (38) increasedin turn and lapathoside D exhibited strongest scavengingability with an IC
50of 0088 120583M [43] Hidropiperosides A
and B (117 118) were reported to show obvious antioxidantresponse to DPPH radicals with the SC
50values of 234
and 267 120583gmL respectively while vanicoside E moderatelyexhibited the same activity with a SC
50value of 490 120583gmL
[72] Lapathoside A (114) and diboside A (116) just showedlower antioxidant activities with the SC
50values of 19948 and
16552 120583M respectively [73]Smiglasides A and B smilaside P 26-di-acetyl-3101584061015840-
di-feruloylsucrose helonioside B smilasides GndashL and het-erosmilaside were isolated from the Heterosmilax and Smi-lax genera Compared with ascorbic acid (IC
5014352 120583M)
used as positive control smiglasides A and B and smi-laside P (48 49 65) (IC
5033958 33066 and 31449 120583M
resp) showed higher antioxidant activities than 26-di-acetyl-3101584061015840-di-feruloylsucrose (73) and helonioside B (40) (IC
50
63166 and 51827120583M resp) [47] Additionally Nhiem et alreported that helonioside B heterosmilaside (104) and 26-di-acetyl-3101584061015840-di-feruloylsucrose exhibited important DPPHradical scavenging activities with the SC
50values of 91 127
and 87 120583gmL respectively [48] Compared with smilasidesG-I (57ndash59) (ED
50685ndash794120583M) smilasides JndashL (60ndash62)
showed higher radical scavenging activities with an ED50
value of 267ndash327120583M [44]Five quiquesetinerviusides AndashE (105ndash109) isolated from
the Calamus genus showed weak DPPH scavenging activ-ities (IC
50604ndash1018120583M) but exhibited better hydroxyl
radical scavenging activities (IC50
36ndash84 120583M) Moreoverquiquesetinerviuside C showed superoxide anion scaveng-ing activity with an IC
50value of about 1843 120583M [70]
Liu et al investigated the antioxidant capacity of 310158406-O-di-sinapoylsucrose (DISS) (123) by using the acceleratedsenescence-prone short-lived mice (SAMP) in vivo Theanalyses indicated that the activities of antioxidant enzymesof SOD and glutathione peroxidase ascended obviously inSAMP mice when amended with DISS 50mgkg MoreoverDISS could downregulate and even restore the level ofmalondialdehyde in SAMP model group [97]
From the above studies it can be concluded that oligosac-charide esters with antioxidant activities have been identifiedin the Polygonaceae Liliaceae Smilacaceae and Arecaceaefamilies The results of the antioxidant assays show that theincreased number of phenolic hydroxyl groups and acetylgroups could produce higher antioxidant activity Fan etal indicated that the increased number of phenylpropanoidgroups was not beneficial to free radical scavenging activity[43] Zhang et al pointed out that oligosaccharide esters withferuloyl groups exhibited better antioxidant activities thanthose with coumaroyl groups [44]
Evidence-Based Complementary and Alternative Medicine 13
Table 3 Fatty acid-derived disaccharide esters
Number Name R1 R2 Source Parts Reference132 61015840-O-Linoleylsucrose H O Astragalus membranaceus Roots [77]133 61015840-O-Palmitoylsucrose H P Astragalus membranaceus Roots [77]134 6-O-Palmitoylsucrose P H Astragalus membranaceus Roots [77]
135 61015840-O-Linolenoylsucrose H N Astragalus membranaceusEquisetum hiemale
RootsAerial parts [77 78]
136 6-O-Linoleylsucrose O H Astragalus membranaceus Roots [77]137 6-O-Myristoylsucrose Q H Astragalus membranaceus Roots [77]
138 6-O-[(7Z10Z13Z)-Hexadeca-71013-trienoyl]sucrose H R Equisetum hiemale Aerial parts [78]
139 6-O-[(7Z10Z)-Hexadeca-710-dienoyl]sucrose H S Equisetum hiemale Aerial parts [78]
See Scheme 3
12
3
4
5
6
1998400
2998400
3998400
4998400
5998400
6998400
HO
O
O
R1O
R2O
R8O
R7OOR3
OR4 OR5OR6
O
O
O
18
18
1616
16
14
N linolenoyl
O linoleyl
P palmitoyl
Q myristoyl
O
O
O
R hexadeca-71013-trienoyl
S hexadeca-710-dienoyl
Scheme 3
32 Antidepressant Activity The oligosaccharides obtainedfrom the Morinda genus not only show specific antidepres-sant and antistress activities but also have no suppression orexcitatory effects on central nervous system as well Whatis more they can be taken orally with little toxicity [21]The inulin-type hexasaccharide (IHS) (9) from Morindaofficinalis obviously exhibited cytoprotective activity whichcontributed to the antidepressant effect not only by providingthe PC12 with protection against Cort-induced lesion withIHS 0625 and 125 120583Mbut also by reducing theCort-induced[Ca2+]
119894overloading with IHS 25 and 10 120583M IHS 5 and
10 120583Mupregulated the nerve growth factormRNAexpressionin Cort-induced PC12 cells [22] Polygalatenosides A (181)and B (182) were isolated from the Polygala genus Theysignificantly inhibited the isotope-labeled RTI-55 binding to
norepinephrine transporter protein with the IC50
values of300 and 604 120583M respectively [91]
DISS and tenuifoliside A were isolated from the PolygalaandCynanchum genera Liu et al investigated the antidepres-sant effect of YZ ethanol extract based on the tail suspensiontest (TST) and forced swimming test (FST) which arethe ease-of-use and widely-accepted models for estimatingantidepressant activities in mice The results indicated thatYZ-50 fraction at a dose of 200mgkgwas able to significantlydecrease the immobility time in TST Furthermore YZ-50possessed ability to inhibit corticosterone-induced injury ofhuman neuroblastoma SH-SY5Y cells What is more DISS(123) and tenuifoliside A (44) two major compounds of YZ-50 fraction showed effective protective response to the lesionin SY5Y cells [53] The antidepressant-like effect of DISS at
14 Evidence-Based Complementary and Alternative Medicine
H3CO
HO
HOHO
HO
HO
HO
HOHO
O O
OO O
OO
O
O
O
OO
O
O
OH
OH
OH
OH
OCH3
OCH3
CH2OH
CH2OH
CH2OAc
CH2OAc
H3CO
HOHO
HO
O
O
O
OO
O
O
OH
OH
OH
OCH3
CH2OH
CH2OH
H3CO
H3CO H3CO
HOHO
HO
O
O
O
OO
O
O
OH
OH
OH
OCH3
CH2OH
CH2OAc
CH3O
H
HOHO
HO
HO
HOO O
OO O
OO
OH
OCH3
CH2OHCH2OH
H3CO H3CO
H
CH2CH2 HO
HO
HO
HO
HOO O
OO O
OO
OH
OCH3
CH2OHCH2OAc
H3CO
H
CH2
140 141 142
143 144 145
Figure 4
Table 4 Phenylpropanoid-derived trisaccharide esters
Number Name R1 R2 R3 R4 R5 R6 R7 Source Parts Reference146 Tricornose C K H H H H L H Polygala tricornis Roots [37]147 Tricornose D K H H H H K H Polygala tricornis Roots [37]148 Tricornose E K H H H K L H Polygala tricornis Roots [37]149 Tricornose F K H H H I L H Polygala tricornis Roots [37]See Scheme 4
O
OOO
O
R2O
R4O
R3O
R6O
OH
OH
OH
OH
OR1
OR5CH2OR7
Scheme 4
the doses of 5 10 and 20mgkg was also tested in chronicallymild stressed rats DISS was able to exhibit antidepressantactivity by upregulating the expression of noradrenergic-regulated plasticity genes including cell adhesion moleculeL1 brain-derived neurotrophic factor laminin and cAMP
response element binding protein factor in hippocampus[98] DISS improved the reward reaction by increasingsucrose intake and obviously decreased the levels of serumcortisol adrenocorticotrophic hormone and corticotropin-releasing factor Further DISS played an enhanced role inthe expression of mineralocorticoid receptor together withglucocorticoid receptor mRNA [99]
33 Cytotoxic and Antineoplastic Activities Smilasides AndashFand P smiglasides A and B smilaside P and helonioside Awere isolated from the Smilax Trillium and Paris generaKuo et al obtained smilasides AndashF (51ndash56) and evaluatedtheir cytotoxicity against human tumor cell lines comprisinghuman oral epithelium carcinoma (KB) human cervicalcarcinoma (Hela) human colon tumor (DLD-1) humanbreast adenocarcinoma (MCF-7) human lung carcinoma (A-549) and humanmedulloblastoma (Med) cells byMTTassayExperimental data indicated that all but smilaside C showedcytotoxicity against three to six human tumor cell lines(ED50
= 51ndash130 120583gmL) and smilasides DndashF (ED50
= 27ndash50 120583gmL) displayed strong cytotoxic activities against DLD-1 cells [46]Wang et al reported the antitumor constituents of
Evidence-Based Complementary and Alternative Medicine 15
OH
OH
OH
OH
OH
OHOH
OHOH
OHOH
OH
OHOHOH
OH
OH
OH
OHOH
OH
OH
OHOH
H
H H
HO
O
O
O
O
O
O
O
OO
OO
O
OO
O
HO
HO
HO
OO
O
O
OO
OO
O
OO
O
OO
O
OO
O
O
O
OO
O
O
OO
O
OO
OOOO
HO
HO
HO
HO
HO
HO
HO
HO
HO
HO
HOHO
HO
HO
HO
HO
HO
150 151 152
153 180
AcO
AcO
AcOAcO
OAc
OAc
CH2OH
OHOH
OH OHOH
OHOH
OH
OHOH
CH3O
Figure 5
Table 5 Phenylpropanoid-derived tetrasaccharide esters
Number Name R1 R2 R3 Source Parts Reference154 Tricornose G K H K Polygala tricornis Roots [37]155 Tricornose H K K K Polygala tricornis Roots [37]156 Tricornose I K K L Polygala tricornis Roots [37]157 Tricornose J K I L Polygala tricornis Roots [37]158 Tricornose K K I K Polygala tricornis Roots [37]159 Tricornose L K G K Polygala tricornis Roots [37]See Scheme 5
Smilax riparia including smiglasides A (48) and B (49) 26-di-acetyl-3101584061015840-di-feruloylsucrose (73) helonioside B (40)and smilaside P (65) Only smiglasidesA andB and smilasideP exhibited cytotoxicity against human tumor cell lines withdifferent inhibitory concentrations comparing with cisplatinand paclitaxel as positive controls [47] Helonioside A (39)exhibited higher cytotoxicity with the increase of concentra-tion (01ndash100120583gmL) [45] Tatarisides AndashG (45 119ndash121 46122 47) and diboside A (116) from the Fagopyrum genusexerted cytotoxic activities against different human cell linesand the cytotoxicity of tatariside C was the most remarkablewith the IC
50values ranging from 644 to 749 120583gmL [57]
11015840236-O-Tetra-acetyl-31015840-O-cis-feruloylsucrose (95) fromthe Sparganium plants exhibited extremely weak cyto-toxicity against the growth of mice Lung Adenocarcinoma
795 cell lines with an IC50
value of 116 120583gmL [66] SnS-2oligosaccharides mixture including raffinose (3) stachyose(19) and verbascose (21) from the roots of Scrophularianingpoensis had antitumor activity against the growth ofLewis pulmonary carcinoma cells transplanted into mice[18]
Disaccharide esters and oligosaccharides mixture fromthe Liliaceae Polygonaceae Sparganiaceae and Scrpophular-iaceae families showed effective cytotoxic and antineoplasticactivities The study results indicated that feruloyl and acetylgroups play an important role in mediating cytotoxicitywhich seems to be related to the substitution position offeruloyl groups The feruloyl groups at C-6 or C-11015840 are vitalfor cytotoxicity In addition the increased number of acetylgroups could induce higher tumoricidal activity
16 Evidence-Based Complementary and Alternative Medicine
Table 6 Phenylpropanoid-derived pentasaccharide esters
Number Name R1 R2 R3 R4 R5 R6 Source Parts Reference160 Tenuifoliose A G D I Ac Ac Ac Polygala tenuifolia Roots [38 42]161 Tenuifoliose B G D I H Ac Ac Polygala tenuifolia Roots [42]162 Tenuifoliose C G D I H H H Polygala tenuifolia Roots [42]163 Tenuifoliose F G D U Ac Ac Ac Polygala tenuifolia Roots [42]164 Tenuifoliose G G D U Ac H Ac Polygala tenuifolia Roots [42]165 Tenuifoliose H G D G Ac Ac Ac Polygala tenuifolia Roots [38 42 79]166 Tenuifoliose I G D G Ac H Ac Polygala tenuifolia Roots [42 79]167 Tenuifoliose J G D G H Ac Ac Polygala tenuifolia Roots [42]168 Tenuifoliose K G D G H H Ac Polygala tenuifolia Roots [42]169 Tenuifoliose L G D T Ac Ac Ac Polygala tenuifolia Roots [42 79]170 Tenuifoliose M G D T Ac H Ac Polygala tenuifolia Roots [42]171 Tenuifoliose N I D I Ac Ac Ac Polygala tenuifolia Roots [42]172 Tenuifoliose O I D I H Ac Ac Polygala tenuifolia Roots [42]173 Tenuifoliose P I D I H H Ac Polygala tenuifolia Roots [42]174 Tenuifoliose Q G D T H Ac Ac Polygala tenuifolia Roots [79]175 Tenuifoliose S G D G H H H Polygala tenuifolia Roots [42]176 Tenuifoliose T G D I H H H Polygala tenuifolia Roots [42]177 Tenuifoliose V H D I Ac Ac Ac Polygala tenuifolia Roots [42]178 Tenuifoliose W I D U Ac H Ac Polygala tenuifolia Roots [42]179 Tenuifoliose X I D I H H H Polygala tenuifolia Roots [42]See Scheme 6
O
OO
O
O
O
O
OR1
OH
OH
OH
OHOH
OH
HOHO
HO
HO
OR2
R3O
CH2OH
Scheme 5
34 Anti-Inflammatory Activity Inflammation an importantbasic pathological process is a defense response of biopsywith vascular system to damage stimuli such as pathogensimpaired cells and tissues and physical and chemical factorsHowever if the process of inflammatory response cannot endnormally when cell debris and pathogens were cleared thebiological defence response will become causative factor andbring about many diseases such as diabetes cardiovasculardiseases metabolic syndrome and cancer [100 101]
Tenuifoliside A (44) from the Polygala genus exhibitedstrong anti-inflammatory effect not only by suppressing the
production of NO but also by reducing the production ofiNOS prostaglandin E2 cyclooxygenase-2 and proinflam-matory cytokines through the inhibition of the mitogen-activated protein kinases pathway and NF-120581B pathway [102]The anti-inflammatory activities of quiquesetinerviusides D(108) and E (109) from the Calamus genus were evaluated inRAW 2647 cells Both of them showed significant inhibitoryeffects against the production of LPS-stimulated NOwith theIC50values of 90ndash295120583M [70]Six disaccharide fatty acid esters (132ndash137) were iso-
lated from the Astragalus and Equisetum genera The anti-inflammatory effects of these isolated compounds have alsobeen documented The activation of NF-120581B could upregulatethe expression of proinflammatory cytokines inducible nitricoxide synthase (iNOS) and tumornecrosis factor alpha (TNF-120572) The NF-120581B inhibitory activities of compounds 132ndash137were tested in HepG2 cells stimulated with TNF-120572 All ofthese compounds could significantly restrainTNF-120572-inducedNF-120581B transcriptional activities with the IC
50values of 44ndash
247 120583M Li et al pointed out that olefinic bonds and thelength of the fatty acid moieties contributed to the NF-120581B inhibitory activity Furthermore the inhibition increasedsignificantly with the increase of the number of olefinic bondson the aliphatic moiety [77] These results may provide ascientific basis for the development of new anti-inflammatoryagents
35 Neuroprotective and Cerebral Protective Activities Aswe all know glutamate works as a major excitatory aminoacid neurotransmitter in the mammalian central nervous
Evidence-Based Complementary and Alternative Medicine 17
R6O
R2O
OR3
OR5
OR4
CH2OR1
OCH3
Rham
OO
O
OO O
O
O
O
OO
RhamO
O
OH
OH
OHOH
OH
OHOH
OHHO
HO
HO
T O-rhamnosyl-coumaroyl U O-rhamnosyl-feruloyl
Scheme 6
system and plays a crucial role in several physiological pro-cesses [103] However the accumulation of glutamate inducesdiverse acute and chronic neurodegenerative diseases suchas epilepsy ischemic stroke and Parkinsonrsquos disease aswell as Alzheimerrsquos disease [104] DISS (123) isolated fromthe Polygala genus exhibited neuroprotective effect againstglutamate-induced SH-SY5Y neuronal cell damage The invitro test demonstrated that DISS (06 6 and 60 120583molL)played a critical role in increasing cell viability controllinglactate dehydrogenase and attenuated apoptosis ranging from195 to 258 [105]
Tenuifoliside B (102) from the Polygala genus was ableto significantly shorten the coma time of KCN-inducedanoxia mice at the doses of 3 and 10mgkg and it playedan important role in ameliorating the scopolamine-inducedimpairment of performance in passive avoidance task inrats and enhancing the tremors induced by oxotremorine inmiceThese results together demonstrated that tenuifoliside Bpossessed cognitive improving and cerebral protective effects[56]
36 Antidiabetic Activity Diabetes mellitus a chronic debil-itating metabolic disease is characterized by high bloodglucose content and comprises three types termed type Itype II and gestational diabetes [106] Stachyose (19) extract(a part) from Rehmannia glutinosa obviously exhibited theactivity of downregulating fasting plasma glucose level andpartially keeping from hyperglycemia induced by adrenalineand glucose without obvious dose-dependent effect Otherthan that in vivo tests in rats induced by alloxan revealed
that stachyose extract at the dose of 200mgkg significantlydecreased blood-sugar level [15]
Diboside A lapathosides C and D vanicosides A andB and hydropiperoside were isolated from the FagopyrumPolygonum and Persicaria genera belonging to the Polygo-naceae family Diboside A (116) could potentially inhibit 120572-amylase activity with an IC
50of 269 120583M and thus retard the
starch digestion rate which is helpful for diabetic individualsin controlling blood sugar level [107] Lapathoside D (38)exerted stronger activity of 120572-glucosidase inhibition with anIC50
value of 0113mM than acarbose which was chosen asa positive drug for the treatment of type II diabetes [43]Vanicoside B (111) was reported to have higher 120573-glucosidaseinhibitory activity with an IC
50of 505 120583M than vanicoside A
(110) with an IC50of 599 120583M because of the acetyl moiety of
the latter possibly decreasing inhibitory activity of vanicosideA [71]
Fujimoto et al investigated the inhibitory effects ofmumeoses FndashO (83ndash92) from the Prunus genus on aldosereductase and discovered that caffeoyl groups are crucialfor the inhibitory effect on aldose reductase And thusmumeoses F G H J K L M and N (IC
50= 22ndash77120583M) with
a coumaroyl group and acetyl groups inhibited moderatelyaldose reductase from reducing glucose to sorbitol whichis associated with the chronic complications of diabetes [6364]
37 Elicitors and Regulators Oligosaccharides are quitepropitious for encoding biological information because ofdiverse monosaccharide units and complex molecular struc-tures and they are therefore first described as biological
18 Evidence-Based Complementary and Alternative Medicine
181 H
H
H
H
H
H
H
H
H H
H
H
H
H
H
H
H H
HH
Benzyl
Benzyl
Benzyl
182
183
184 Ac
Ac
Ac
Ac
Ac
Ac
Ac
Ac
Ac
Ac
185
186
187
188
189
R1 R2 R3
R1 R2 R3 R4
OCH3
R3OH2C OR2
OR1
OR1
O
O
O
O O
OOO
O
OO
O
OH
OH
OH OH
OH
O O
O
O
OH
HO
OH
OH OHOH
OH
OH
OHHO
HO
OH
OH
HO
CH2OH
CH2OH
CH2OH
CH2OH
C
R2O
R3O
CH2OR4
CH2CH2 CH2CH2CH2CH2CH3
CH3
CH3
191190 192
193
O
C C
O
OO
OO
OO
OO
O O
O
O
O
O
O
O
OH
OH
OHHO
HO
HOOH
OH
OH
OH
HO
OH
OH
OH
OH
HO
HO
C C
R998400O
R998400
Figure 6
signals in plants [108] Oligosaccharides from the cell wallfragments of plants and fungi are powerful signal moleculessuch as the elicitors of plant defence response and theregulators of plant growth and they are capable of exertingbiological activities at exceedingly low concentrations [109]Heptasaccharide (HS) (15) and octasaccharide (OS) (16) iso-lated from the Paris genus possessed plant growth-regulatory
activities [29 30]The two oligosaccharides significantly pro-moted the proliferation of Paris polyphylla var yunnanensisroots at the doses of 25ndash20mgL The octasaccharide hadthe most obvious effect on the growth of Panax japonicusvar major hairy roots at a dose of 30mgL while the otherhad the most positive effect on saponin accumulation ofPanax japonicus var major hairy roots at a dose of 10mgL
Evidence-Based Complementary and Alternative Medicine 19
[29] Similarly Zhou et al evaluated the stimulating effectsof HS and OS on the root growth and saponin productionof Panax ginseng hairy roots which were induced from theplant roots infected withAgrobacterium rhizogenes strain A4The results showed that there was a maximum effect on thehairy roots growth and saponin accumulation on day 10Compared with control group the root biomass dry weightwas increased by more than 17-fold while the total saponincontent of roots increased by more than 1-fold when thesetwo oligosaccharides were added to the hairy root at a dose of30mgL [30] The above data illustrate that HS and OS couldserve as the plant growth-regulators not only in their originalspecies but also in others
38 Immunopotentiating Activity Macrophages are impor-tant targets of investigations on cytophagy cellular immunityand molecular immunology Therefore they are deemedto play a vital role in host defense comprising phagocy-tosis proteolytic processing pathogenic agent apoptosiscytokines production and foreign antigens presentation[110] The water-extracted oligosaccharides from Panax gin-seng (WGOS) exhibited better immunopotentiating activ-ity by increasing phagocytic function of macrophages andpromoting NO TNF-120572 and reactive oxygen species pro-duction [110] In addition Wan et al have obtained malto-oligosaccharides (17 119899 = 3sim8) and three oligosaccharides (213 14) from the Panax ginseng roots The in vitro bioassaypointed out thatWGOS could serve as efficacious stimulatorsof B and T lymphocytes [28] These studies provided enlight-enment that the mixture of oligosaccharides from Chineseherbalmedicine exhibits significant effect on immune system
39 Others Acetylcholinesterase (AChE) inhibitors showgood therapeutic effects onmyasthenia gravis glaucoma andAlzheimerrsquos disease through reversible enzyme inhibitionso as to increase the accumulation of acetylcholine in thesynapse and then promote and prolong the function ofacetylcholine Vanicoside B (111) showed AChE inhibitoryactivity with an IC
50of 0062mM while hydropiperoside
(42) and lapathosides C (115) and D (38) just exhibited weakenzyme inhibitory activity [43]
Wang et al has explored low molecular mass carbohy-drate polymer from Panax ginseng roots and obtained 30ethanol elution (PGO)which included peptides and oligosac-charides (17 119899 = 0sim5) identified as maltose maltotriosemaltotetraose maltopentaose maltohexaose and maltohep-taose Pharmacological experiments revealed that PGO couldsignificantly enhance the memory in scopolamine-inducedmemory deficit rats [27]
Cistanoside F (129) and kankanose (150) were isolatedfrom the Cistanche Paulownia and Acanthus genera Phar-macological experiments showed that cistanoside F andkankanose significantly exhibited vasorelaxant effects on thenoradrenaline-induced contraction of thoracic aorta fromrats [80]
4 Conclusion
Traditional Chinese medicine from natural kingdom playsan indelible role in the treatment of human diseases andit has aroused the attention of those who have engagedin medicinal pharmaceutical chemistry Therefore scientistshave made great contributions day after day to investigate thevalid chemicals from traditional Chinese medicines In thepast decades about 193 oligosaccharides and their esters havebeen identified from traditional Chinese medicinal plantsOn the one hand only a few oligosaccharides and theirmixtures were investigated and just exhibited antidepres-sant antineoplastic antidiabetic plant growth-regulatoryimmunopotentiating and enhancedmemory activitiesMoreexploratory work is still needed to excavate biological andpharmacological activities of oligosaccharides On the otherhand oligosaccharide esters exhibited multi-advantageousactivities Bioassays have revealed that antioxidant cytotoxicantineoplastic and anti-inflammatory activities are the mostnotable bioactivities Of course to search for the naturalproducts with these activities is a hotpot in the contemporarydrug research Oligosaccharide esters provide a vast treasuretrove for medical researchers After considering the currentstudies it should be taken as future directions to makemore mechanism of action studies and clinical trials tofurther evaluate its potential as new drugs Moreover thestructure-activity relationships discussed in this review willprovide reference information for further exploring theirrelationships and continually discovering the new bioactiveoligosaccharide esters
Conflict of Interests
The authors declare that there is no conflict of interestsregarding the publication of this paper
References
[1] X D Yang L J Zhang B Liang L Z Xu and S L YangldquoOligosaccharide esters isolated from plants of PolygalaceaerdquoChinese Traditional and Herbal Drugs vol 33 no 10 pp 954ndash958 2002
[2] N Ogwuru and M Adamczeski ldquoBioactive natural productsderived from Polygonum species of plants their structures andmechanisms of actionrdquo Studies in Natural Products Chemistryvol 22 pp 607ndash642 2000
[3] S Kobayashi T Miyase and H Noguchi ldquoPolyphenolic glyco-sides and oligosaccharide multiesters from the roots of Polygaladalmaisianardquo Journal of Natural Products vol 65 no 3 pp 319ndash328 2002
[4] M Takasaki S Kuroki M Kozuka and T Konoshima ldquoNewphenylpropanoid esters of sucrose from Polygonum lapathi-foliumrdquo Journal of Natural Products vol 64 no 10 pp 1305ndash1308 2001
[5] M L Zimmermann and A T Sneden ldquoVanicosides A and Bprotein kinase C inhibitors from Polygonum pensylvanicumrdquoJournal of Natural Products vol 57 no 2 pp 236ndash242 1994
[6] M Takasaki T Konoshima S Kuroki H Tokuda and HNishino ldquoCancer chemopreventive activity of phenylpropanoid
20 Evidence-Based Complementary and Alternative Medicine
esters of sucrose vanicoside B and lapathoside A from Poly-gonum lapathifoliumrdquo Cancer Letters vol 173 no 2 pp 133ndash138 2001
[7] Q Fu T Liang Z Y Li et al ldquoSeparation of carbohydrates usinghydrophilic interaction liquid chromatographyrdquo CarbohydrateResearch vol 379 pp 13ndash17 2013
[8] M F Mrozek D Zhang and D Ben-Amotz ldquoOligosaccharideidentification and mixture quantification using Raman spec-troscopy and chemometric analysisrdquo Carbohydrate Researchvol 339 no 1 pp 141ndash145 2004
[9] G S Armstrong and B Bendiak ldquoHigh-resolution four-dimen-sional carbon-correlated 1H-1H ROESY experiments employ-ing isotags and the filter diagonalization method for effectiveassignment of glycosidic linkages in oligosaccharidesrdquo Journalof Magnetic Resonance vol 181 no 1 pp 79ndash88 2006
[10] G S Armstrong V A Mandelshtam A J Shaka and BBendiak ldquoRapid high-resolution four-dimensional NMR spec-troscopy using the filter diagonalization method and its advan-tages for detailed structural elucidation of oligosaccharidesrdquoJournal of Magnetic Resonance vol 173 no 1 pp 160ndash168 2005
[11] H-M Tseng S Gattolin J Pritchard H J Newbury and DA Barrett ldquoAnalysis of mono- di- and oligosaccharides by CEusing a two-stage derivatization method and LIF detectionrdquoElectrophoresis vol 30 no 8 pp 1399ndash1405 2009
[12] N Li X Li B L Hou and D L Meng ldquoNew disaccharosidefrom Camptosorus sibiricus Ruprrdquo Natural Product Researchvol 22 no 15 pp 1379ndash1383 2008
[13] Z Zhang D Wang Y Zhao H Gao Y-H Hu and J-FHu ldquoFructose-derived carbohydrates from Alisma orientalisrdquoNatural Product Research vol 23 no 11 pp 1013ndash1020 2009
[14] X Yang Y Zhao N He and K D Croft ldquoIsolation char-acterization and immunological effects of 120572-galacto-oligo-saccharides from a new source the herb Lycopus lucidus TurczrdquoJournal of Agricultural and Food Chemistry vol 58 no 14 pp8253ndash8258 2010
[15] R X Zhang Z P Jia L Y Kong et al ldquoStachyose extractfrom Rehmannia glutinosa Libosch to lower plasma glucose innormal and diabetic rats by oral administrationrdquo Pharmazievol 59 no 7 pp 552ndash556 2004
[16] R Zhang Y Zhao Y Sun X Lu and X Yang ldquoIsolationcharacterization and hepatoprotective effects of the raffinosefamily oligosaccharides from Rehmannia glutinosa liboschrdquoJournal of Agricultural and Food Chemistry vol 61 no 32 pp7786ndash7793 2013
[17] H Li F Song Z Zheng Z Liu and S Liu ldquoCharacterization ofsaccharides and phenolic acids in the Chinese herb Tanshen byESI-FT-ICR-MS and HPLCrdquo Journal of Mass Spectrometry vol43 no 11 pp 1545ndash1552 2008
[18] J E Deng J Zhang XM ChenW Ke and G Y Tian ldquoStudieson the physicochemical properties structure and antitumoractivity of an oligosaccharide homologue SnS-2 from the root ofScrophularia ningpoensis Hemslrdquo Chinese Journal of Chemistryvol 22 no 5 pp 492ndash497 2004
[19] S C Chou LM Chuang and S S Lee ldquoHypoglycemic constit-uents of gynura divaricata subsp formosanardquo Natural ProductCommunications vol 7 no 2 pp 221ndash222 2012
[20] F Feng L-L Wang X-P Lai Y-B Li Z-M Cao and Y-J Zhou ldquoStudy on oligosaccharides from Morinda officinalisrdquoJournal of Chinese Medicinal Materials vol 35 no 8 pp 1259ndash1262 2012
[21] Y F Li Z H Gong M Yang Y M Zhao and Z P Luo ldquoInhibi-tion of the oligosaccharides extracted fromMorinda officinalis
a Chinese traditional herbal medicine on the corticosteroneinduced apoptosis in PC12 cellsrdquo Life Sciences vol 72 no 8 pp933ndash942 2003
[22] Y-F Li Y-Q Liu M Yang et al ldquoThe cytoprotective effect ofinulin-type hexasaccharide extracted from Morinda officinalison PC12 cells against the lesion induced by corticosteronerdquo LifeSciences vol 75 no 13 pp 1531ndash1538 2004
[23] D N Olennikov L M Tankhaeva and A V Rokhin ldquoGlu-cofructans from Saussurea lappa rootsrdquo Chemistry of NaturalCompounds vol 47 no 3 pp 339ndash342 2011
[24] S K Hyun H A Jung B S Min J H Jung and J S ChoildquoIsolation of phenolics nucleosides saccharides and an alkaloidfrom the root of Aralia cordatardquo Natural Product Sciences vol16 no 1 pp 20ndash25 2010
[25] Z J Xu C W Lin and M F Liao ldquoStructure analysis of a newoligosaccharides BROS from Blumea ripariardquo Chinese Journalof Organic Chemistry vol 31 no 11 pp 1811ndash1819 2011
[26] Z J Xu C W Lin and Y Shi ldquoIsolation and structuredetermination of a new oligosaccharide from Blume ripariardquoJournal of Medicinal Plants Research vol 5 no 14 pp 2956ndash2962 2011
[27] Y Wang R Z Jiang G R Li et al ldquoStructural and enhancedmemory activity studies of extracts from Panax ginseng rootrdquoFood Chemistry vol 119 no 3 pp 969ndash973 2010
[28] DWan L Jiao H Yang and S Liu ldquoStructural characterizationand immunological activities of the water-soluble oligosaccha-rides isolated from thePanax ginseng rootsrdquoPlanta vol 235 no6 pp 1289ndash1297 2012
[29] L G Zhou C Z Yang J Q Li S L Wang and J Y WuldquoHeptasaccharide and octasaccharide isolated from Paris pol-yphylla var yunnanensis and their plant growth-regulatoryactivityrdquo Plant Science vol 165 no 3 pp 571ndash575 2003
[30] L G Zhou X D Cao R F Zhang Y L Peng S J Zhao andJ Y Wu ldquoStimulation of saponin production in Panax ginsenghairy roots by two oligosaccharides from Paris polyphylla varyunnanensisrdquo Biotechnology Letters vol 29 no 4 pp 631ndash6342007
[31] M Vanhaecke W van den Ende E Lescrinier and N Dyu-bankova ldquoIsolation and characterization of a pentasaccharidefrom Stellaria mediardquo Journal of Natural Products vol 71 no 11pp 1833ndash1836 2008
[32] J Feng and W Zhao ldquoComplete 1Hand 13C NMR assignmentsof four new oligosaccharides and two new glycosides fromPeriploca forrestiirdquoMagnetic Resonance in Chemistry vol 47 no8 pp 701ndash705 2009
[33] J Q Feng R J Zhang Y Zhou et al ldquoImmunosuppressive preg-nane glycosides from Periploca sepium and Periploca forrestiirdquoPhytochemistry vol 69 no 15 pp 2716ndash2723 2008
[34] X H Long R Xu Y H Zhang X H Tan andQ Y Sun ldquoA newoligosaccharide from Periploca calophyllardquo Zhongguo ZhongyaoZazhi vol 37 no 2 pp 226ndash229 2012
[35] L Wang Z-Q Yin Y Wang X-Q Zhang Y-L Li and W-CYe ldquoPerisesaccharides A-E new oligosaccharides from the rootbarks ofPeriploca sepiumrdquoPlantaMedica vol 76 no 9 pp 909ndash915 2010
[36] T Lei L Zhang H-Y Jiang Y Hu A-H Hong and Y-Z CenldquoA new pregnane glycoside and oligosaccharide from Parabar-ium huaitingiirdquo Journal of Asian Natural Products Research vol13 no 11 pp 1030ndash1035 2011
[37] J Li Y Jiang and P F Tu ldquoTricornoses A-L oligosaccharidemulti-esters from the roots of Polygala tricornisrdquo Journal ofNatural Products vol 68 no 5 pp 739ndash744 2005
Evidence-Based Complementary and Alternative Medicine 21
[38] H H Tu P Liu L Mu et al ldquoStudy on antidepressant com-ponents of sucrose ester from Polygala tenuifoliardquo ZhongguoZhongyao Zazhi vol 33 no 11 pp 1278ndash1280 2008
[39] G M She Y Y Ba Y Liu H Lv W Wang and R B ShildquoAbsorbable phenylpropenoyl sucroses from Polygala tenuifo-liardquoMolecules vol 16 no 7 pp 5507ndash5513 2011
[40] J Yong and P F Tu ldquoStudies on the chemical constituents inroot bark of Polygala tenuifolia (II)rdquo China Journal of ChineseMateria Medica vol 29 no 8 pp 751ndash753 2004
[41] M Ono C Takamura F Sugita et al ldquoTwo new steroidglycosides and a new sesquiterpenoid glycoside from theunderground parts of Trillium kamtschaticumrdquo Chemical andPharmaceutical Bulletin vol 55 no 4 pp 551ndash556 2007
[42] Y Ling Z Li M Chen Z Sun M Fan and C HuangldquoAnalysis and detection of the chemical constituents of RadixPolygalae and their metabolites in rats after oral administrationby ultra high-performance liquid chromatography coupledwith electrospray ionization quadrupole time-of-flight tandemmass spectrometryrdquo Journal of Pharmaceutical and BiomedicalAnalysis vol 85 pp 1ndash13 2013
[43] P Fan L Terrier A-E Hay A Marston and K HostettmannldquoAntioxidant and enzyme inhibition activities and chemicalprofiles ofPolygonum sachalinensis FSchmidt exMaxim (Polyg-onaceae)rdquo Fitoterapia vol 81 no 2 pp 124ndash131 2010
[44] L J Zhang C C Liao H C Huang Y C Shen L M Yangand Y H Kuo ldquoAntioxidant phenylpropanoid glycosides fromSmilax bracteatardquo Phytochemistry vol 69 no 6 pp 1398ndash14042008
[45] L L Yan W Y Gao Y J Zhang and Y Wang ldquoA new phenyl-propanoid glycosides from Paris polyphylla var yunnanensisrdquoFitoterapia vol 79 no 4 pp 306ndash307 2008
[46] Y H Kuo Y W Hsu C C Liaw J K Lee H C Huang andL M Y Kuo ldquoCytotoxic phenylpropanoid glycosides from thestems of Smilax chinardquo Journal of Natural Products vol 68 no10 pp 1475ndash1478 2005
[47] W-X Wang T-X Li H Ma J-F Zhang and A-Q JialdquoTumoral cytotoxic and antioxidative phenylpropanoid glyco-sides in Smilax riparia A DCrdquo Journal of Ethnopharmacologyvol 149 no 2 pp 527ndash532 2013
[48] N X Nhiem P vanKiem C vanMinh et al ldquoPhenylpropanoidglycosides fromHeterosmilax erythrantha and their antioxidantactivityrdquo Archives of Pharmacal Research vol 32 no 10 pp1373ndash1377 2009
[49] Y Wang W Y Gao T J Zhang and Y Q Guo ldquoA novelphenylpropanoid glycosides and a new derivation of phenolicglycoside from Paris Polyphylla var yunnanensisrdquo ChineseChemical Letters vol 18 no 5 pp 548ndash550 2007
[50] J-Y Zhang Y-Z Wang Y-L Zhao et al ldquoPhytochemicals andbioactivities of Paris speciesrdquo Journal of Asian Natural ProductsResearch vol 13 no 7 pp 670ndash681 2011
[51] N H N Hashim F Abas K Shaari and N H Lajis ldquoLC-DAD-ESIMSMS characterization of antioxidant and anti-cholinesterase constituents present in the active fraction fromPersicaria hydropiperrdquo LWT Food Science and Technology vol46 no 2 pp 468ndash476 2012
[52] PH FanA EHayAMarstonHX Lou andKHostettmannldquoChemical variability of the invasive neophytes Polygonumcuspidatum Sieb and Zucc and Polygonum sachalinensis FSchmidt ex Maximrdquo Biochemical Systematics and Ecology vol37 no 1 pp 24ndash34 2009
[53] P Liu Y Hu D H Guo et al ldquoPotential antidepressantproperties of Radix Polygalae (Yuan Zhi)rdquo Phytomedicine vol17 no 10 pp 794ndash799 2010
[54] J F Wu S B Chen S L Chen and P F Tu ldquoThe chemical con-stituents of Polygala hongkongensisHemslrdquoActa PharmaceuticaSinica vol 42 no 7 pp 757ndash761 2007
[55] Y Song Y Jiang D Bi X Tian L Liang and P Tu ldquoChemicalconstituents from n-butanol extract of aerial part of Polygalasibiricardquo Zhongguo Zhongyao Zazhi vol 37 no 4 pp 471ndash4742012
[56] Y Ikeya S Takeda M Tunakawa et al ldquoCognitive improvingand cerebral protective effects of acylated oligosaccharides inPolygala tenuifoliardquo Biological and Pharmaceutical Bulletin vol27 no 7 pp 1081ndash1085 2004
[57] C J Zheng C L Hu X Q Ma C Peng H Zhang and L PQin ldquoCytotoxic phenylpropanoid glycosides from Fagopyrumtataricum (L) Gaertnrdquo Food Chemistry vol 132 no 1 pp 433ndash438 2012
[58] X Li Y F Zhang L Yang et al ldquoChemical profiling ofconstituents of Smilacis glabrae using ultra-high pressure liquidchromatography coupled with LTQ orbitrap mass spectrome-tryrdquo Natural Product Communications vol 7 no 2 pp 181ndash1842012
[59] T-T Sun D-W Zhang Y Han F-Y Dong andWWang ldquoSmi-lasides M and N two new phenylpropanoid glycosides fromSmilax ripariardquo Journal of Asian Natural Products Research vol14 no 2 pp 165ndash170 2012
[60] J Li X Bi G Zheng Y Hitoshi T Ikeda and T NoharaldquoSteroidal glycosides and aromatic compounds from Smilaxripariardquo Chemical amp Pharmaceutical Bulletin vol 54 no 10 pp1451ndash1454 2006
[61] N Wang X Yao R Ishii and S Kitanaka ldquoBioactive sucroseesters from Bidens parviflorardquo Phytochemistry vol 62 no 5 pp741ndash746 2003
[62] S Nakamura K Fujimoto T Matsumoto et al ldquoAcylatedsucroses and acylated quinic acids analogs from the flower budsof Prunus mume and their inhibitory effect on melanogenesisrdquoPhytochemistry vol 92 pp 128ndash136 2013
[63] K Fujimoto SNakamura TMatsumoto et al ldquoMedicinal flow-ers XXXVIII Structures of acylated sucroses and inhibitoryeffects of constituents on aldose reducatase from the flower budsofPrunusmumerdquoChemical and Pharmaceutical Bulletin vol 61no 4 pp 445ndash451 2013
[64] S Nakamura K Fujimoto T Matsumoto et al ldquoStructuresof acylated sucroses and an acylated flavonol glycoside andinhibitory effects of constituents on aldose reductase from theflower buds of Prunus mumerdquo Journal of Natural Medicines vol67 no 4 pp 799ndash806 2013
[65] L-B Dong J He X-Y Li et al ldquoChemical constituents fromthe aerial parts of Musella lasiocarpardquo Natural Products andBioprospecting vol 1 no 1 pp 41ndash47 2011
[66] Y Xiong K Z Deng Y Q Guo W Y Gao and T J ZhangldquoNew chemical constituents from the rhizomes of Sparganiumstoloniferumrdquo Archives of Pharmacal Research vol 32 no 5 pp717ndash720 2009
[67] Y Xiong K-Z Deng Y-Q Guo W-Y Gao and T-J ZhangldquoTwo new sucrose esters from Sparganium stoloniferumrdquo Jour-nal of Asian Natural Products Research vol 10 no 5 pp 425ndash428 2008
[68] B Chen N L Wang J H Huang and X S Yao ldquoIridoidand phenylpropanoid glycosides from Scrophularia ningpoensis
22 Evidence-Based Complementary and Alternative Medicine
Hemslrdquo Asian Journal of Traditional Medicines vol 2 no 3 pp119ndash123 2007
[69] H Chen Y Z Zhou L Qiao et al ldquoTwo new compounds fromCynanchum amplexicaulerdquo Journal of Asian Natural ProductsResearch vol 10 no 3 pp 248ndash251 2008
[70] C-L Chang L-J Zhang R Y Chen et al ldquoAntioxidant andanti-inflammatory phenylpropanoid derivatives from Calamusquiquesetinerviusrdquo Journal of Natural Products vol 73 no 9 pp1482ndash1488 2010
[71] Y Kawai H Kumagai H Kurihara K Yamazaki R Sawanoand N Inoue ldquo120573-Glucosidase inhibitory activities of phenyl-propanoid glycosides vanicoside A and B from Polygonumsachalinense rhizomerdquo Fitoterapia vol 77 no 6 pp 456ndash4592006
[72] P V Kiem N X Nhiem N X Cuong et al ldquoNew phenyl-propanoid esters of sucrose from Polygonum hydropiper andtheir antioxidant activityrdquo Archives of Pharmacal Research vol31 no 11 pp 1477ndash1482 2008
[73] K J Wang Y J Zhang and C R Yang ldquoAntioxidant phenolicconstituents from Fagopyrum dibotrysrdquo Journal of Ethnophar-macology vol 99 no 2 pp 259ndash264 2005
[74] N Cho J Huh H Yang et al ldquoChemical constituentsof Polygala tenuifolia roots and their inhibitory activity onlipopolysaccharide-induced nitric oxide production in BV2microgliardquo Journal of Enzyme Inhibition and Medicinal Chem-istry vol 27 no 1 pp 1ndash4 2012
[75] Q Ren C S Wu and J L Zhang ldquoUse of on-line stop-flowheart-cutting two-dimensional high performance liquid chro-matography for simultaneous determination of 12 major con-stituents in tartary buckwheat (Fagopyrum tataricum Gaertn)rdquoJournal of Chromatography A vol 1304 pp 257ndash262 2013
[76] Q Ren C S Wu Y Ren and J L Zhang ldquoCharacterizationand identification of the chemical constituents from tartarybuckwheat (Fagopyrum tataricumGaertn) by high performanceliquid chromatographyphotodiode array detectorlinear iontrap FTICR hybrid mass spectrometryrdquo Food Chemistry vol136 no 3-4 pp 1377ndash1389 2013
[77] W Li Y N Sun X T Yan et al ldquoNF-120581B inhibitory activityof sucrose fatty acid esters and related constituents fromAstragalus membranaceusrdquo Journal of Agricultural and FoodChemistry vol 61 no 29 pp 7081ndash7088 2013
[78] J T Cheng J He Y Li et al ldquoThree new sucrose fatty acid estersfrom Equisetum hiemale LrdquoHelvetica Chimica Acta vol 95 no7 pp 1158ndash1163 2012
[79] Y Jiang and P-F Tu ldquoTenuifoliose Q a new oligosaccharideester from the root of Polygala tenuifoliaWilldrdquo Journal of AsianNatural Products Research vol 5 no 4 pp 279ndash283 2003
[80] M Yoshikawa H Matsuda T Morikawa H H Xie S Naka-mura and O Muraoka ldquoPhenylethanoid oligoglycosides andacylated oligosugars with vasorelaxant activity from Cistanchetubulosardquo Bioorganic ampMedicinal Chemistry vol 14 no 22 pp7468ndash7475 2006
[81] P-F Tu H-M Shi Z-H Song Y Jiang and Y-Y ZhaoldquoChemical constituents of Cistanche sinensisrdquo Journal of AsianNatural Products Research vol 9 no 1 pp 79ndash84 2007
[82] C-L Si Y-Y Lu P-P Qin R-C Sun and Y-H Ni ldquoPhenolicextractives with chemotaxonomic significance from the bark ofPaulownia tomentosa var tomentosardquo BioResources vol 6 no4 pp 5086ndash5098 2011
[83] J Wu S Zhang Q Xiao et al ldquoPhenylethanoid and aliphaticalcohol glycosides from Acanthus ilicifoliusrdquo Phytochemistryvol 63 no 4 pp 491ndash495 2003
[84] Y Jiang and P-F Tu ldquoAnalysis of chemical constituents inCistanche speciesrdquo Journal of Chromatography A vol 1216 no11 pp 1970ndash1979 2009
[85] H Otsuka H Kuwabara and H Hoshiyama ldquoIdentification ofsucrose diesters of aryldihydronaphthalene-type lignans fromTrigonotis peduncularisand the nature of their fluorescencerdquoJournal of Natural Products vol 71 no 7 pp 1178ndash1181 2008
[86] M-R Suo J-S Yang and Q-H Liu ldquoLignan oligosaccharideesters from Eritrichium rupestrerdquo Journal of Natural Productsvol 69 no 4 pp 682ndash684 2006
[87] P-F Tu Z-H Song H-M Shi Y Jiang and Y-Y ZhaoldquoArylethyl (=phenylethanoid) glycosides and oligosaccharidefrom the stem of Cistanche tubulosardquo Helvetica Chimica Actavol 89 no 5 pp 927ndash935 2006
[88] M-H Shyr T-H Tsai and L-C Lin ldquoRossicasins A Band rosicaside F three new phenylpropanoid glycosides fromBoschniakia rossicardquoChemical and Pharmaceutical Bulletin vol54 no 2 pp 252ndash254 2006
[89] R FangNCVeitchGCKiteM J RHowes EA Porter andM S J Simmonds ldquoGlycosylated constituents of Iris fulvaandIris brevicaulisrdquoChemical amp Pharmaceutical Bulletin vol 59 no1 pp 124ndash128 2011
[90] J Fu L Zuo J Yang R Chen and D Zhang ldquoOligosaccharidepolyester and triterpenoid saponins from the roots of Polygalajaponicardquo Phytochemistry vol 69 no 7 pp 1617ndash1624 2008
[91] M-C Cheng C-Y Li H-C Ko F-N Ko Y-L Lin andT-S Wu ldquoAntidepressant principles of the roots of polygalatenuifoliardquo Journal of Natural Products vol 69 no 9 pp 1305ndash1309 2006
[92] H T Chang and P F Tu ldquoNew oligosaccharide esters andxanthone C-glucosides from Polygala telephioidesrdquo HelveticaChimica Acta vol 90 no 5 pp 944ndash950 2007
[93] J Li L Feng J Dai R Wang and T Nohara ldquoChemical con-stituents from Polygala telephioidesrdquo China Journal of ChineseMateria Medica vol 34 no 4 pp 402ndash405 2009
[94] W-P Yin T-Z Zhao and H-Y Zhang ldquoA novel oligosaccha-ride ester from Syringa pubescensrdquo Journal of Asian NaturalProducts Research vol 10 no 1 pp 95ndash100 2008
[95] M Valko D Leibfritz J Moncol M T D Cronin M Mazurand J Telser ldquoFree radicals and antioxidants in normal physio-logical functions and human diseaserdquoThe International Journalof Biochemistry amp Cell Biology vol 39 no 1 pp 44ndash84 2007
[96] D Krishnaiah R Sarbatly and R Nithyanandam ldquoA review ofthe antioxidant potential of medicinal plant speciesrdquo Food andBioproducts Processing vol 89 no 3 pp 217ndash233 2011
[97] P Liu Y Hu D-H Guo et al ldquoAntioxidant activity ofoligosaccharide ester extracted from Polygala tenuifolia roots insenescence-accelerated micerdquo Pharmaceutical Biology vol 48no 7 pp 828ndash833 2010
[98] Y Hu H-B Liao G Dai-Hong P Liu Y-Y Wang and KRahman ldquoAntidepressant-like effects of 361015840-disinapoyl sucroseon hippocampal neuronal plasticity and neurotrophic signalpathway in chronically mild stressed ratsrdquo NeurochemistryInternational vol 56 no 3 pp 461ndash465 2010
[99] Y Hu H B O Liao P Liu D-H Guo and K RahmanldquoA bioactive compound from Polygala tenuifolia regulatesefficiency of chronic stress on hypothalamic-pituitary-adrenalaxisrdquo Pharmazie vol 64 no 9 pp 605ndash608 2009
[100] A Jungbauer and SMedjakovic ldquoAnti-inflammatory propertiesof culinary herbs and spices that ameliorate the effects ofmetabolic syndromerdquoMaturitas vol 71 no 3 pp 227ndash239 2012
Evidence-Based Complementary and Alternative Medicine 23
[101] Q Xu Y Wang S Guo Z Shen and L Yang ldquoAnti-inflammatory and analgesic activity of aqueous extract of Flospopulirdquo Journal of Ethnopharmacology vol 152 no 3 pp 540ndash545 2014
[102] K S Kim D S Lee G S Bae et al ldquoThe inhibition of JNKMAPK and NF-120581B signaling by tenuifoliside A isolated fromPolygala tenuifolia in lipopolysaccharide-induced macrophagesis associated with its anti-inflammatory effectrdquo European Jour-nal of Pharmacology vol 721 no 1ndash3 pp 267ndash276 2013
[103] J-G Lee J-M Yon C Lin A Y Jung K Y Jung and S-YNamldquoCombined treatment with capsaicin and resveratrol enhancesneuroprotection against glutamate-induced toxicity in mousecerebral cortical neuronsrdquo Food and Chemical Toxicology vol50 no 11 pp 3877ndash3885 2012
[104] M L Jin S Y Park Y H Kim J-I Oh S J Lee andG Park ldquoThe neuroprotective effects of cordycepin inhibitglutamate-induced oxidative andER stress-associated apoptosisin hippocampal HT22 cellsrdquo NeuroToxicology vol 41 pp 102ndash111 2014
[105] P Liu Y Hu J Li et al ldquoProtection of SH-SY5Y neuronal cellsfrom glutamate-induced apoptosis by 36rsquo-disinapoyl sucrosea bioactive compound isolated from radix polygalardquo Journal ofBiomedicine and Biotechnology vol 2012 Article ID 728342 5pages 2012
[106] P-B Li W-L Lin Y-G Wang W Peng X-Y Cai and W-WSu ldquoAntidiabetic activities of oligosaccharides of Ophiopogonisjaponicus in experimental type 2 diabetic ratsrdquo InternationalJournal of Biological Macromolecules vol 51 no 5 pp 749ndash7552012
[107] T Liu Y M Yip L Song et al ldquoInhibiting enzymatic starchdigestion by the phenolic compound diboside A a mechanisticand in silico studyrdquo Food Research International vol 54 no 1pp 595ndash600 2013
[108] F Cote andMGHahn ldquoOligosaccharins structures and signaltransductionrdquo Plant Molecular Biology vol 26 no 5 pp 1379ndash1411 1994
[109] RACreelman and J EMullet ldquoOligosaccharins brassinolidesand jasmonates nontraditional regulators of plant growthdevelopment and gene expressionrdquo Plant Cell vol 9 no 7 pp1211ndash1223 1997
[110] L Jiao D Wan X Zhang B Li H Zhao and S LiuldquoCharacterization and immunostimulating effects on murineperitoneal macrophages of oligosaccharide isolated from Panaxginseng CAMeyerrdquo Journal of Ethnopharmacology vol 144 no3 pp 490ndash496 2012
Submit your manuscripts athttpwwwhindawicom
Stem CellsInternational
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
MEDIATORSINFLAMMATION
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Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
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Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Disease Markers
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
BioMed Research International
OncologyJournal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
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Oxidative Medicine and Cellular Longevity
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
PPAR Research
The Scientific World JournalHindawi Publishing Corporation httpwwwhindawicom Volume 2014
Immunology ResearchHindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Journal of
ObesityJournal of
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Computational and Mathematical Methods in Medicine
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Research and TreatmentAIDS
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Gastroenterology Research and Practice
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Parkinsonrsquos Disease
Evidence-Based Complementary and Alternative Medicine
Volume 2014Hindawi Publishing Corporationhttpwwwhindawicom
Evidence-Based Complementary and Alternative Medicine 3
Table1Oligosaccharides
No
Nam
eR 1
R 2R 3
R 4R 5
R 6Source
Parts
Reference
22PerifosaccharideA
OH(e)
OCH
3(e)
HOH(e)
OH
APerip
loca
forrestii
Roots
[32]
23PerifosaccharideB
OH(e)
OCH
3(a)
HOH(e)
OH
APerip
loca
forrestii
Roots
[32]
24PerifosaccharideC
OH(e)
OCH
3(e)
HOH(e)
OCH
3A
Perip
loca
forrestii
Roots
[32]
25PerifosaccharideD
OAc
(e)
OCH
3(e)
HOH(e)
OH
APerip
loca
forrestii
Roots
[32]
26Peris
accharideA
OH(a)
OCH
3(e)
OAc
OH(e)
OCH
3A
Perip
loca
sepium
Root
barks
[33]
27Peris
accharideB
OAc
(e)
OCH
3(a)
HOH(e)
OH
APerip
loca
sepium
Perip
loca
calophylla
Root
barks
[3334]
28Peris
accharideC
OH(a)
OCH
3(e)
OAc
OCH
3(a)
OH
APerip
loca
sepium
Root
barks
[33]
29Peris
accharideD
OAc
(e)
OCH
3(a)
HOH(e)
OCH
3A
Perip
loca
calophylla
Stem
s[34]
30Peris
esaccharideB
OH(a)
OCH
3(e)
OAc
OH(e)
OCH
3C
Perip
loca
sepium
Root
barks
[35]
31Peris
esaccharideC
OH(a)
OCH
3(e)
OH
OCH
3(a)
OCH
3C
Perip
loca
sepium
Root
barks
[35]
32Peris
esaccharideD
OH(a)
OCH
3(e)
OH
OCH
3(a)
OH
CPerip
loca
sepium
Root
barks
[35]
33Peris
esaccharideE
OH(a)
OCH
3(e)
OAc
OH(e)
OH
CPerip
loca
sepium
Root
barks
[35]
34
Cymarop
yranurolactone
4-O-120573-D
-digita
lopyrano
syl-
(1rarr4)-O
-120573-D
-cymarop
yranosyl-(1rarr4)-O
-120573-
D-oleandrop
yranosyl-(1rarr4)-
O-120573-D
-cym
arop
yranoside
OH(a)
OCH
3(e)
OH
OCH
3(e)
OCH
3B
Parabariu
mhu
aitin
gii
Barks
[36]
SeeS
chem
e1
4 Evidence-Based Complementary and Alternative Medicine
R1
R2 R3
R4
R5
R6
O OO
OO
O
O
OO
O O OO
O
O
O
OCH3
H3COH3CO
H3CO
A oleandronic acid-120575-lactone B cymaropyranurolactone C oleandronic acid-120575-lactone
Scheme 1
222 Fatty Acid-Derived Disaccharide Esters Eight mono-substituted disaccharide esters (Table 3) with a sucrose moi-ety possess six different types of fatty acid residues whichattach to the 6 or 61015840 position of sucrose These fatty acidsinclude linoleic acid palmitic acid linolenic acid myris-tic acid hexadeca-71013-trienoic acid and hexadeca-710-dienoic acid The above sucrose fatty acid esters have beenfound in the rhizomes of Astragalus membranaceus and theroots of Equisetum hiemale
223 Lignan-DerivedDisaccharide Esters Six lignan-deriveddisaccharide esters (Figure 4) contain a sucrose core esterifiedwith different lignan residues covalently linked to the 31015840and 61015840 positions of 120573-D-fructofuranosyl unit and have beenisolated from the whole parts of Trigonotis peduncularis [85]and the aerial parts of Eritrichium rupestre [86]
224 Phenylpropanoid-Derived Trisaccharide Esters Inthis group all oligosaccharide esters consist of threemonosaccharides including glucopyranose fructofuranoseand rhamnopyranose with O-substituents which compriseferuloyl sinapoyl and 345-trimethoxycinnamoyl groupsOligosaccharide esters (146ndash149) listed in Table 4 as well askankanose (150) cistantubulose A
1A2(151) cistansinensose
A1A2(152) and compound 153 shown in Figure 5 have
been found in the roots of Polygala tricornis [37] the stemsof Cistanche tubulosa [81 87] and C sinensis [80] the wholeparts of Boschniakia rossica [88] and the rhizomes of Irisbrevicaulis [89]
225 Phenylpropanoid-Derived Tetrasaccharide Esters Phe-nylpropanoid-derived tetrasaccharide esters (154ndash159)(Table 5) consisting of three glucopyranosyl units and afructofuranosyl unit have been identified from the rootsof Polygala tricornis The nonsugar moieties of theseoligosaccharides include coumaroyl feruloyl sinapoyl and345-trimethoxycinnamoyl groups
226 Phenylpropanoid-Derived Pentasaccharide Esters Asshown in Table 6 oligosaccharide esters (160-179) possess-ing a skeleton of five sugar residues have been isolatedfrom the roots of Polygala tenuifolia The sugar residues
are composed of two types of monosaccharides includ-ing fructofuranose and glucopyranose which are esterifiedwith acetyl benzoyl rhamnose-substitutednonsubstitutedcoumaroyl and rhamnose-substitutednonsubstituted feru-loyl groups Other than that a structure-complex oligosac-charide polyester shown in Figure 5 polygalajaponicose I(180) consisting of a pentasaccharide backbone esterifiedwith feruloyl coumaroyl rhamnosyl-coumaroyl acetyl andbenzoyl groups has been obtained from the roots of Pjaponica [90]
227 Others Polygalatenosides AndashC (181ndash183) (Figure 6)containing a galactosyl unit and a polygolitosyl unit esterifiedwith benzoyl groups at 3 4 and 6 positions have been foundin the roots of Polygala tenuifolia [91] Three sucrose estersincluding polygalatenoside D (190) telephiose F (191) and6-O-benzoylsucrose (192) possess one benzoyl group twobenzoyl groups and a p-methoxybenzoyl group respectivelyThey were isolated from the roots of P tenuifolia [91] thewhole plants of P telephioides [92] and the roots of P tricornis[37] Six trisaccharide esters named telephioses AndashE and G(184ndash189) with substituents of acetyl and benzoyl groupswere isolated from the whole plants of P telephioides [92 93]Moreover a trisaccharide ester (193) pubescenside A fromthe flowers of Syringa pubescens possesses a fatty acid residue[94]
3 Biological Activities ofOligosaccharides and Their Esters
The oligosaccharides and oligosaccharide esters from Chi-nese medicinal plants are important products with diver-sified structures which have triggered an increasing num-ber of studies carried out on the isolated compoundsAnd thus diverse pharmacological activities have beenproved Among the isolated compounds oligosaccharidesphenylpropanoid-derived disaccharide esters and trisaccha-ride esters fatty acid-derived disaccharide esters and othersfrom the families Polygonaceae Asclepiadaceae RubiaceaePolygalaceae Liliaceae Smilacaceae Arecaceae Oroban-chaceae Scrophulariaceae Acanthaceae Rosaceae Sparga-niaceae Leguminosae and Equisetaceae have shown sig-nificant pharmacological activities including antioxidant
Evidence-Based Complementary and Alternative Medicine 5
1 2 3 4
5 6 7 8
9 10 11 12
13 14 15
16 17
OHOH
OH
OHOH
OHOH
OH
OHOH
OH
OO
O
OOO
HOHO
HO
HOHO CH2OH
CH2OH
CH2
2
2
3
4 5
5
66
6n
OH
OH
OH
OH
OHO O
O
OO
HO
HO
HO HO
HO
HO
OH
OHO OHO
HO OHO OHO
HO OHO
HOHO
OH
OH
OH
OH
OHOH
OHO OHO
HO OHO OHO
HO OHO
O
OO
OO
HO
HOHO
HOHO
HOHO
OHCH2OH
CH2
OH
OH
OH
OHO
OO
OO
HOHO HO
HOHO
HOHO
2
CH2OH
CH2
OH
OH
OH
OHO
OO
OO
HO
HOHO
HOHO
CH2OH
CH2
OH
OH
OH
OHO
OO
OO
HO
HOHO HO
HOHO
CH2OH
CH2
OH
OH
OH
OHO
OO
OO
HO
HO
HO HO
HOHO
CH2OH
CH2
OH
OH
OH
OHO
OO
OO
HO
HOHO HO
HOHO
CH2
OH
OH
OH OH
OHO
OO
OO
HO
HOHO HO
HOHO
OH
OH
OHOH
OH
OH
O
OO
O
OHO
HO
HOHO
HO
OH
OH
OH OHOH
OH
O
OO
O
OHO
HO
HOHO
HO
OH
OH OH
OH
OH
OH
OO
O O
O
HOHO HO
HO
HO
OH
OH OH
OH
OH
OO
O O
O
HOHO HO
HO
HOHO OH
OH
OH OHOH
OH
O
OO
O
O
HOHO
HO
HO
HO
Figure 1 Continued
6 Evidence-Based Complementary and Alternative Medicine
18 19
20 21
2
n
OH
OH
H
OH
OH
OH
OH
OO
O
O
O
HO
HOHO
HO
HO
CH2OH
OH
OHO OHO
HO OHO OHO
HO OH
OH
O
OO
HO
HOHO
HO
CH2OH
OH
OHO OHO
HO OHO OHO
HO OH
OH
O
OO
HO
HOHO
OH
OH
OHOHO
HO
OH
OH
OH
OH
OH
OHO
O
O
O
O
O
O
HO
HO
HO
OH
OH
OH
OH O
Figure 1
D benzoyl E p-methoxybenzoyl F p-hydroxybenzoyl G coumaroyl
I feruloyl J caffeoyl K sinapoyl
L 345-trimethoxycinnamoyl M cinnamoyl
O
O
O
O O O
OO
O
OCH3
OCH3
OCH3
OCH3
OCH3
OCH3
OCH3
OH
OHOH
OHOHOH
Figure 2
Evidence-Based Complementary and Alternative Medicine 7
Table2Ph
enylprop
anoid-deriv
eddisaccharid
eeste
rs
Num
ber
Nam
eR 1
R 2R 3
R 4R 5
R 6R 7
R 8Source
Parts
Reference
35Sibiric
oseA
6H
HH
HK
HH
HPolyg
alatricornis
Polyg
alatenu
ifolia
Roots
Root
barks
[37ndash40
]
3631015840-O
-FeruloylsucroseSibiricose
A5
HH
HH
IH
HH
Polyg
alatenu
ifolia
Trillium
kamtsc
haticum
Roots
Und
ergrou
ndparts
[38ndash42]
37GlomeratoseA
HH
HH
LH
HH
Polyg
alatricornis
Roots
[37]
38LapathosideD
HH
HH
GG
HH
Polyg
onum
sachalinense
Stem
s[43]
39Helo
niosideA
HH
HH
II
HH
Trillium
kamtsc
haticum
Smila
xbracteata
Paris
polyphylla
varyunn
anensis
Und
ergrou
ndparts
Aeria
lparts
Roots
[4144
45]
40Helo
niosideB
AcH
HH
II
HH
Smila
xbracteata
Smila
xchina
Smila
xrip
aria
Heterosmila
xerythrantha
Aeria
lparts
Stem
sRo
otsa
ndrhizom
es
[4446
ndash48]
41Paris
polysid
eFH
HH
HG
IH
HPa
risPolyphylla
varyunn
anensis
Rhizom
es[4950]
42Hydropiperosid
eH
HH
HG
GH
GPolyg
onum
sachalinense
Polyg
onum
cuspidatum
Persica
riahydropiper
Stem
sLeaves
[435152]
43Tricorno
seB
DAc
HH
LH
HH
Polyg
alatricornis
Roots
[37]
44Tenu
ifolisideA
FH
HH
LH
HH
Polyg
alatenu
ifolia
Polygalahongkongensis
Polyg
alasib
irica
Roots
Who
leplants
Aeria
lparts
[3840
4253ndash
56]
45Tataris
ideA
AcH
HAc
GG
HAc
Fagopyrum
tataric
umRo
ots
[57]
46Tataris
ideE
HH
HAc
GG
HAc
Fagopyrum
tataric
umRo
ots
[57]
47Tataris
ideG
HH
HH
IG
HG
Fagopyrum
tataric
umRo
ots
[57]
48Sm
iglasid
eAAc
AcH
AcI
IH
ISm
ilaxrip
aria
Rootsa
ndrhizom
es[47]
49Sm
iglasid
eBAc
HH
AcI
IH
ISm
ilaxrip
aria
Rootsa
ndrhizom
es[47]
50Sm
iglasid
eEAc
HH
AcI
IH
GSm
ilaxchina
Stem
s[46]
51Sm
ilasid
eAAc
AcH
HI
IH
HSm
ilaxchina
Stem
s[46]
52Sm
ilasid
eBH
HH
AcI
IH
HSm
ilaxchina
Stem
s[46]
53Sm
ilasid
eCH
HH
HI
IH
GSm
ilaxchina
Stem
s[46]
54Sm
ilasid
eDH
HH
HI
IAc
GSm
ilaxchina
Stem
s[46]
8 Evidence-Based Complementary and Alternative Medicine
Table2Con
tinued
Num
ber
Nam
eR 1
R 2R 3
R 4R 5
R 6R 7
R 8Source
Parts
Reference
55Sm
ilasid
eEAc
HH
HI
IH
GSm
ilaxbracteata
Smila
xchina
Aeria
lparts
Stem
s[4446
]
56Sm
ilasid
eFAc
HH
AcG
IH
GSm
ilaxchina
Stem
s[46]
57Sm
ilasid
eGH
HH
HG
IH
GSm
ilaxbracteata
Smilacis
glabrae
Aeria
lparts
Rhizom
es[4458]
58Sm
ilasid
eHH
HH
AcG
IH
GSm
ilaxbracteata
Aeria
lparts
[44]
59Sm
ilasid
eIAc
HH
HG
IH
GSm
ilaxbracteata
Aeria
lparts
[44]
60Sm
ilasid
eJH
HH
HG
IH
ISm
ilaxbracteata
Smilacis
glabrae
Aeria
lparts
Rhizom
es[4458]
61Sm
ilasid
eKH
HH
AcI
IH
GSm
ilaxbracteata
Aeria
lparts
[44]
62Sm
ilasid
eLH
HH
HI
IH
ISm
ilaxbracteata
Smilacis
glabrae
Aeria
lparts
Rhizom
es[4458]
63Sm
ilasid
eMAc
HH
AcCis-feruloyl
IH
HSm
ilaxrip
aria
Rootsa
ndrhizom
es[59]
64Sm
ilasid
eNAc
HH
AcI
Cis-
feruloyl
HH
Smila
xrip
aria
Rootsa
ndrhizom
es[59]
65Sm
ilasid
ePH
HH
AcI
IH
ISm
ilaxrip
aria
Rootsa
ndrhizom
es[47]
66310158404101584061015840-O
-Tri-
feruloylsucrose
HH
HH
II
IH
Smila
xrip
aria
Rhizom
esand
roots
[60]
6761015840-O
-Cou
maroylsu
crose
HH
HH
HG
HH
Bidens
parviflora
Who
leplants
[61]
6811015840 -O-C
oumaroyl-61015840-O
-feruloylsucrose
HH
HH
HI
HG
Smila
xbracteata
Aeria
lparts
[44]
694-O-Benzoyl-31015840-345-
trim
etho
xycinn
amoylsu
crose
HD
HH
LH
HH
Polyg
alatricornis
Roots
[37]
706-O-Benzoyl-31015840-O
-345-
trim
etho
xycinn
amoylsu
crose
DH
HH
LH
HH
Polyg
alatricornis
Roots
[37]
716-O-Benzoyl-31015840-O
-sin
apoylsu
crose
DH
HH
KH
HH
Polyg
alatricornis
Roots
[37]
726-O-p-M
etho
xybenzoyl-31015840-O
-345-
trim
etho
xycinn
amoylsu
crose
EH
HH
LH
HH
Polyg
alatenu
ifolia
Roots
[56]
7326-Di-a
cetyl-3101584061015840-di-
feruloylsucrose
AcH
HAc
II
HH
Smila
xchina
Smila
xrip
aria
Heterosmila
xerythrantha
Stem
sRo
otsa
ndrhizom
esAe
rialp
arts
[46ndash
4859]
7426-Di-a
cetyl-31015840-O
-cis-feruloy-
61015840-tr
ans-feruloylsucrose
AcH
HAc
Cis-feruloy
IH
HSm
ilaxrip
aria
Rootsa
ndrhizom
es[59]
Evidence-Based Complementary and Alternative Medicine 9
Table2Con
tinued
Num
ber
Nam
eR 1
R 2R 3
R 4R 5
R 6R 7
R 8Source
Parts
Reference
7526-Di-a
cetyl-31015840-O
-tran
s-feruloy-
61015840-cis-feruloylsucrose
AcH
HAc
ICis-
feruloyl
HH
Smila
xrip
aria
Rootsa
ndrhizom
es[59]
76Re
galosid
eAAc
HH
HI
HH
HTrillium
kamtsc
haticum
Und
ergrou
ndparts
[41]
77Tricorno
seA
AcH
HH
LH
HH
Polyg
alatricornis
Roots
[37]
78Mum
eose
AH
HH
AcG
HH
HPrun
usmum
eFlow
erbu
ds[6263]
79Mum
eose
BAc
HAc
HG
HH
HPrun
usmum
eFlow
erbu
ds[6263]
80Mum
eose
CAc
HAc
AcG
HH
HPrun
usmum
eFlow
erbu
ds[6263]
81Mum
eose
DAc
AcAc
AcG
HH
AcPrun
usmum
eFlow
erbu
ds[6263]
82Mum
eose
EAc
AcAc
AcCis-
coum
aroyl
HH
AcPrun
usmum
eFlow
erbu
ds[6263]
83Mum
eose
FAc
AcAc
HG
HH
HPrun
usmum
eFlow
erbu
ds[63]
84Mum
eose
GAc
HAc
HG
HAc
HPrun
usmum
eFlow
erbu
ds[63]
85Mum
eose
HH
HAc
AcG
HAc
HPrun
usmum
eFlow
erbu
ds[63]
86Mum
eose
IAc
AcAc
HG
AcH
HPrun
usmum
eFlow
erbu
ds[63]
87Mum
eose
JAc
AcAc
AcG
HAc
AcPrun
usmum
eFlow
erbu
ds[63 ]
88Mum
eose
KH
HAc
AcG
HH
HPrun
usmum
eFlow
erbu
ds[64]
89Mum
eose
LAc
HAc
AcG
HAc
HPrun
usmum
eFlow
erbu
ds[64]
90Mum
eose
MAc
AcAc
HG
HAc
AcPrun
usmum
eFlow
erbu
ds[64]
91Mum
eose
NAc
AcAc
HG
AcAc
HPrun
usmum
eFlow
erbu
ds[64]
92Mum
eose
OAc
HAc
AcG
HAc
AcPrun
usmum
eFlow
erbu
ds[64]
9311015840 2346-O-Penta-acetyl-31015840-O
-tra
ns-cou
maroylsu
crose
AcAc
AcAc
GH
HAc
Musellalasio
carpa
Aeria
lparts
[65]
9411015840 2346-O-Penta-acetyl-31015840-O
-cis-cou
maroylsu
crose
AcAc
AcAc
Cis-
coum
aroyl
HH
AcMusellalasio
carpa
Aeria
lparts
[65]
9511015840 236-O-Tetra-acetyl-31015840-O
-cis-
feruloylsucrose
AcH
AcAc
Cis-feruloyl
HH
AcSparganium
stolonifer
umRh
izom
es[66]
9611015840 246-O-Tetra-acetyl-31015840-O
-tra
ns-fe
ruloylsucrose
AcAc
HAc
IH
HAc
Sparganium
stolonifer
umRh
izom
es[66]
9711015840 236-O-Tetra-acetyl-31015840-O
-tra
ns-fe
ruloylsucrose
AcH
AcAc
IH
HAc
Sparganium
stolonifer
umRh
izom
es[67]
98Sibirio
sideA
MH
HH
HH
HH
Scrophularianingpoensis
Roots
[68]
99SibricoseA
1K
HH
HH
HH
HCy
nanchu
mam
plexica
ule
Roots
[69]
100
6-O-C
affeoylsucrose
JH
HH
HH
HH
Scrophularianingpoensis
Roots
[68]
101
Acretosid
eI
HH
HH
HH
HScrophularianingpoensis
Roots
[68]
10 Evidence-Based Complementary and Alternative Medicine
Table2Con
tinued
Num
ber
Nam
eR 1
R 2R 3
R 4R 5
R 6R 7
R 8Source
Parts
Reference
102
Tenu
ifolisideB
FH
HH
KH
HH
Polyg
alatenu
ifolia
Roots
[4256]
103
Tenu
ifolisideC
KH
HH
LH
HH
Polyg
alatricornis
Polyg
alatenu
ifolia
Roots
[374256]
104
Heterosmilasid
eH
HI
HH
IH
HHeterosmila
xerythrantha
Aeria
lparts
[48]
105
Quiqu
esetinerviusideA
HI
HH
II
HH
Calamus
quiquesetin
ervius
Stem
s[70]
106
Quiqu
esetinerviusideB
AcI
HH
II
HH
Calamus
quiquesetin
ervius
Stem
s[70]
107
Quiqu
esetinerviusideC
HI
HAc
II
HH
Calamus
quiquesetin
ervius
Stem
s[70]
108
Quiqu
esetinerviusideD
AcG
HH
II
HH
Calamus
quiquesetin
ervius
Stem
s[70]
109
Quiqu
esetinerviusideE
HG
HAc
II
HH
Calamus
quiquesetin
ervius
Stem
s[70]
110
Vanicosid
eAI
HH
AcG
GH
G
Polyg
onum
sachalinensis
Polyg
onum
cuspidatum
Polyg
onum
hydropiper
Stem
sLeaves
Rhizom
es[51527172]
111
Vanicosid
eBI
HH
HG
GH
G
Polyg
onum
sachalinensis
Polyg
onum
cuspidatum
Persica
riahydropiper
Stem
sLeaves
Rhizom
es[4351527172]
112
Vanicosid
eDG
HH
HG
GH
GPersica
riahydropiper
Leaves
[51]
113
Vanicosid
eEI
AcH
AcG
GH
GPolyg
onum
hydropiper
Stem
sand
leaves
[72]
114
LapathosideA
IH
HH
GG
HI
Polyg
onum
sachalinensis
Polyg
onum
cuspidatum
Fagopyrum
dibotrys
Stem
sRh
izom
es[5173]
115
LapathosideC
IH
HH
GG
HH
Polyg
onum
sachalinensis
Polyg
onum
cuspidatum
Stem
s[4352]
116
DibosideA
GH
HH
GI
HG
Fagopyrum
tataric
umFagopyrum
dibotrys
Roots
Rhizom
es[57]
117
Hidropiperosid
eAI
HH
HH
GH
GPolyg
onum
hydropiper
Stem
sand
leaves
[72]
118
Hidropiperosid
eBI
HH
AcG
GH
IPolyg
onum
hydropiper
Stem
sand
leaves
[72]
119
Tataris
ideB
IH
HAc
GG
HAc
Fagopyrum
tataric
umRo
ots
[57]
Evidence-Based Complementary and Alternative Medicine 11
Table2Con
tinued
Num
ber
Nam
eR 1
R 2R 3
R 4R 5
R 6R 7
R 8Source
Parts
Reference
120
Tataris
ideC
IAc
HAc
GG
HAc
Fagopyrum
tataric
umRo
ots
[57]
121
Tataris
ideD
GH
HAc
GI
HH
Fagopyrum
tataric
umRo
ots
[57]
122
Tataris
ideF
GH
HH
II
HG
Fagopyrum
tataric
umRo
ots
[57]
123
310158406-O
-Di-sinapoylsu
crose
KH
HH
KH
HH
Polyg
alatricornis
Polygalahongkongensis
Polyg
alasib
irica
Polyg
alatenu
ifolia
Cynanchu
mam
plexica
ule
Roots
Root
barks
Who
leplants
Aeria
lparts
[37ndash394153ndash
566974]
124
661015840-O
-Di-c
oumaroylsu
crose
GH
HH
HG
HH
Bidens
parviflora
Who
leplants
[61]
125
11015840 3101584061015840-O
-Tri-
coum
aroyl-6
-feruloylsucrose
IH
HH
GG
HG
Fagopyrum
tataric
umRo
ots
[7576]
126
3101584061015840-O
-Di-c
oumaroyl-110158406-O
-di-
feruloylsucrose
IH
HH
GG
HI
Fagopyrum
tataric
umRo
ots
[7576]
127
31015840-O
-Cou
maroyl-11015840610158406-O
-tri-
feruloylsucrose
IH
HH
IG
HI
Fagopyrum
tataric
umRo
ots
[7576]
128
11015840 31015840610158406-O
-Tetra-fe
ruloylsucrose
IH
HH
II
HI
Fagopyrum
tataric
umRo
ots
[7576]
SeeS
chem
e2
12 Evidence-Based Complementary and Alternative Medicine
131130129
CH2OHOH
OH
OO
OH
C
C
HH
HHO
OO
O
HO
HOHO
HO
HOOH
OHOHOH
OHOH
HOO
O
O
O
HO
HO
OH
OHOHOH
OHOH
HOO
O
O
O
HO
Figure 3
12
3
4
5
6
1998400
2998400
3998400
4998400
5998400
6998400
HO
O
O
R1O
R2O
R8O
R7OOR3
OR4 OR5OR6
Scheme 2
antidepressant cytotoxic antineoplastic anti-inflammatoryantidiabetic plant growth-regulatory neuroprotective andcerebral protective activities Lignan-derived disaccharideesters phenylpropanoid-derived tetrasaccharide esters andpentasaccharide esterswith biological activities have not beenreported Aside from the isolated constituents oligosaccha-ride mixtures from Rehmannia glutinosa Panax ginseng andScrophularia ningpoensiswere also reported to display diversepharmacological activities such as antidiabetic immunopo-tentiating enhanced memory and antineoplastic activitiesThese active compounds and mixtures could serve as thevaluable candidates to be developed as possible drugs for thetreatment and prevention of diseases
31 Antioxidant Activity The adverse effects of oxidativestress proposed to play significant roles in the pathogenesis ofcardiovascular diseases atherosclerosis hypertension can-cer diabetes mellitus neurodegenerative diseases rheuma-toid arthritis ischemiareperfusion injury and ageing havebecome an inevitable and serious issue [95 96] Scientistshave thus made great efforts to explore antioxidants frommedicinal plants by using different kinds of assay methodswhich include DPPH radical scavenging assay hydroxylradical scavenging assay superoxide anion scavenging assayand ABTS radical scavenging method [96]
Lapathosides C and D hydropiperoside vanicoside Bhidropiperosides A and B lapathoside A and diboside Awere isolated from the Polygonum Persicaria and Fagopyrumgenera belonging to the Polygonaceae family The DPPH testrevealed that free radical-scavenging activity of the isolatedcompounds termed lapathoside C (115) hydropiperoside(42) vanicoside B (111) and lapathoside D (38) increasedin turn and lapathoside D exhibited strongest scavengingability with an IC
50of 0088 120583M [43] Hidropiperosides A
and B (117 118) were reported to show obvious antioxidantresponse to DPPH radicals with the SC
50values of 234
and 267 120583gmL respectively while vanicoside E moderatelyexhibited the same activity with a SC
50value of 490 120583gmL
[72] Lapathoside A (114) and diboside A (116) just showedlower antioxidant activities with the SC
50values of 19948 and
16552 120583M respectively [73]Smiglasides A and B smilaside P 26-di-acetyl-3101584061015840-
di-feruloylsucrose helonioside B smilasides GndashL and het-erosmilaside were isolated from the Heterosmilax and Smi-lax genera Compared with ascorbic acid (IC
5014352 120583M)
used as positive control smiglasides A and B and smi-laside P (48 49 65) (IC
5033958 33066 and 31449 120583M
resp) showed higher antioxidant activities than 26-di-acetyl-3101584061015840-di-feruloylsucrose (73) and helonioside B (40) (IC
50
63166 and 51827120583M resp) [47] Additionally Nhiem et alreported that helonioside B heterosmilaside (104) and 26-di-acetyl-3101584061015840-di-feruloylsucrose exhibited important DPPHradical scavenging activities with the SC
50values of 91 127
and 87 120583gmL respectively [48] Compared with smilasidesG-I (57ndash59) (ED
50685ndash794120583M) smilasides JndashL (60ndash62)
showed higher radical scavenging activities with an ED50
value of 267ndash327120583M [44]Five quiquesetinerviusides AndashE (105ndash109) isolated from
the Calamus genus showed weak DPPH scavenging activ-ities (IC
50604ndash1018120583M) but exhibited better hydroxyl
radical scavenging activities (IC50
36ndash84 120583M) Moreoverquiquesetinerviuside C showed superoxide anion scaveng-ing activity with an IC
50value of about 1843 120583M [70]
Liu et al investigated the antioxidant capacity of 310158406-O-di-sinapoylsucrose (DISS) (123) by using the acceleratedsenescence-prone short-lived mice (SAMP) in vivo Theanalyses indicated that the activities of antioxidant enzymesof SOD and glutathione peroxidase ascended obviously inSAMP mice when amended with DISS 50mgkg MoreoverDISS could downregulate and even restore the level ofmalondialdehyde in SAMP model group [97]
From the above studies it can be concluded that oligosac-charide esters with antioxidant activities have been identifiedin the Polygonaceae Liliaceae Smilacaceae and Arecaceaefamilies The results of the antioxidant assays show that theincreased number of phenolic hydroxyl groups and acetylgroups could produce higher antioxidant activity Fan etal indicated that the increased number of phenylpropanoidgroups was not beneficial to free radical scavenging activity[43] Zhang et al pointed out that oligosaccharide esters withferuloyl groups exhibited better antioxidant activities thanthose with coumaroyl groups [44]
Evidence-Based Complementary and Alternative Medicine 13
Table 3 Fatty acid-derived disaccharide esters
Number Name R1 R2 Source Parts Reference132 61015840-O-Linoleylsucrose H O Astragalus membranaceus Roots [77]133 61015840-O-Palmitoylsucrose H P Astragalus membranaceus Roots [77]134 6-O-Palmitoylsucrose P H Astragalus membranaceus Roots [77]
135 61015840-O-Linolenoylsucrose H N Astragalus membranaceusEquisetum hiemale
RootsAerial parts [77 78]
136 6-O-Linoleylsucrose O H Astragalus membranaceus Roots [77]137 6-O-Myristoylsucrose Q H Astragalus membranaceus Roots [77]
138 6-O-[(7Z10Z13Z)-Hexadeca-71013-trienoyl]sucrose H R Equisetum hiemale Aerial parts [78]
139 6-O-[(7Z10Z)-Hexadeca-710-dienoyl]sucrose H S Equisetum hiemale Aerial parts [78]
See Scheme 3
12
3
4
5
6
1998400
2998400
3998400
4998400
5998400
6998400
HO
O
O
R1O
R2O
R8O
R7OOR3
OR4 OR5OR6
O
O
O
18
18
1616
16
14
N linolenoyl
O linoleyl
P palmitoyl
Q myristoyl
O
O
O
R hexadeca-71013-trienoyl
S hexadeca-710-dienoyl
Scheme 3
32 Antidepressant Activity The oligosaccharides obtainedfrom the Morinda genus not only show specific antidepres-sant and antistress activities but also have no suppression orexcitatory effects on central nervous system as well Whatis more they can be taken orally with little toxicity [21]The inulin-type hexasaccharide (IHS) (9) from Morindaofficinalis obviously exhibited cytoprotective activity whichcontributed to the antidepressant effect not only by providingthe PC12 with protection against Cort-induced lesion withIHS 0625 and 125 120583Mbut also by reducing theCort-induced[Ca2+]
119894overloading with IHS 25 and 10 120583M IHS 5 and
10 120583Mupregulated the nerve growth factormRNAexpressionin Cort-induced PC12 cells [22] Polygalatenosides A (181)and B (182) were isolated from the Polygala genus Theysignificantly inhibited the isotope-labeled RTI-55 binding to
norepinephrine transporter protein with the IC50
values of300 and 604 120583M respectively [91]
DISS and tenuifoliside A were isolated from the PolygalaandCynanchum genera Liu et al investigated the antidepres-sant effect of YZ ethanol extract based on the tail suspensiontest (TST) and forced swimming test (FST) which arethe ease-of-use and widely-accepted models for estimatingantidepressant activities in mice The results indicated thatYZ-50 fraction at a dose of 200mgkgwas able to significantlydecrease the immobility time in TST Furthermore YZ-50possessed ability to inhibit corticosterone-induced injury ofhuman neuroblastoma SH-SY5Y cells What is more DISS(123) and tenuifoliside A (44) two major compounds of YZ-50 fraction showed effective protective response to the lesionin SY5Y cells [53] The antidepressant-like effect of DISS at
14 Evidence-Based Complementary and Alternative Medicine
H3CO
HO
HOHO
HO
HO
HO
HOHO
O O
OO O
OO
O
O
O
OO
O
O
OH
OH
OH
OH
OCH3
OCH3
CH2OH
CH2OH
CH2OAc
CH2OAc
H3CO
HOHO
HO
O
O
O
OO
O
O
OH
OH
OH
OCH3
CH2OH
CH2OH
H3CO
H3CO H3CO
HOHO
HO
O
O
O
OO
O
O
OH
OH
OH
OCH3
CH2OH
CH2OAc
CH3O
H
HOHO
HO
HO
HOO O
OO O
OO
OH
OCH3
CH2OHCH2OH
H3CO H3CO
H
CH2CH2 HO
HO
HO
HO
HOO O
OO O
OO
OH
OCH3
CH2OHCH2OAc
H3CO
H
CH2
140 141 142
143 144 145
Figure 4
Table 4 Phenylpropanoid-derived trisaccharide esters
Number Name R1 R2 R3 R4 R5 R6 R7 Source Parts Reference146 Tricornose C K H H H H L H Polygala tricornis Roots [37]147 Tricornose D K H H H H K H Polygala tricornis Roots [37]148 Tricornose E K H H H K L H Polygala tricornis Roots [37]149 Tricornose F K H H H I L H Polygala tricornis Roots [37]See Scheme 4
O
OOO
O
R2O
R4O
R3O
R6O
OH
OH
OH
OH
OR1
OR5CH2OR7
Scheme 4
the doses of 5 10 and 20mgkg was also tested in chronicallymild stressed rats DISS was able to exhibit antidepressantactivity by upregulating the expression of noradrenergic-regulated plasticity genes including cell adhesion moleculeL1 brain-derived neurotrophic factor laminin and cAMP
response element binding protein factor in hippocampus[98] DISS improved the reward reaction by increasingsucrose intake and obviously decreased the levels of serumcortisol adrenocorticotrophic hormone and corticotropin-releasing factor Further DISS played an enhanced role inthe expression of mineralocorticoid receptor together withglucocorticoid receptor mRNA [99]
33 Cytotoxic and Antineoplastic Activities Smilasides AndashFand P smiglasides A and B smilaside P and helonioside Awere isolated from the Smilax Trillium and Paris generaKuo et al obtained smilasides AndashF (51ndash56) and evaluatedtheir cytotoxicity against human tumor cell lines comprisinghuman oral epithelium carcinoma (KB) human cervicalcarcinoma (Hela) human colon tumor (DLD-1) humanbreast adenocarcinoma (MCF-7) human lung carcinoma (A-549) and humanmedulloblastoma (Med) cells byMTTassayExperimental data indicated that all but smilaside C showedcytotoxicity against three to six human tumor cell lines(ED50
= 51ndash130 120583gmL) and smilasides DndashF (ED50
= 27ndash50 120583gmL) displayed strong cytotoxic activities against DLD-1 cells [46]Wang et al reported the antitumor constituents of
Evidence-Based Complementary and Alternative Medicine 15
OH
OH
OH
OH
OH
OHOH
OHOH
OHOH
OH
OHOHOH
OH
OH
OH
OHOH
OH
OH
OHOH
H
H H
HO
O
O
O
O
O
O
O
OO
OO
O
OO
O
HO
HO
HO
OO
O
O
OO
OO
O
OO
O
OO
O
OO
O
O
O
OO
O
O
OO
O
OO
OOOO
HO
HO
HO
HO
HO
HO
HO
HO
HO
HO
HOHO
HO
HO
HO
HO
HO
150 151 152
153 180
AcO
AcO
AcOAcO
OAc
OAc
CH2OH
OHOH
OH OHOH
OHOH
OH
OHOH
CH3O
Figure 5
Table 5 Phenylpropanoid-derived tetrasaccharide esters
Number Name R1 R2 R3 Source Parts Reference154 Tricornose G K H K Polygala tricornis Roots [37]155 Tricornose H K K K Polygala tricornis Roots [37]156 Tricornose I K K L Polygala tricornis Roots [37]157 Tricornose J K I L Polygala tricornis Roots [37]158 Tricornose K K I K Polygala tricornis Roots [37]159 Tricornose L K G K Polygala tricornis Roots [37]See Scheme 5
Smilax riparia including smiglasides A (48) and B (49) 26-di-acetyl-3101584061015840-di-feruloylsucrose (73) helonioside B (40)and smilaside P (65) Only smiglasidesA andB and smilasideP exhibited cytotoxicity against human tumor cell lines withdifferent inhibitory concentrations comparing with cisplatinand paclitaxel as positive controls [47] Helonioside A (39)exhibited higher cytotoxicity with the increase of concentra-tion (01ndash100120583gmL) [45] Tatarisides AndashG (45 119ndash121 46122 47) and diboside A (116) from the Fagopyrum genusexerted cytotoxic activities against different human cell linesand the cytotoxicity of tatariside C was the most remarkablewith the IC
50values ranging from 644 to 749 120583gmL [57]
11015840236-O-Tetra-acetyl-31015840-O-cis-feruloylsucrose (95) fromthe Sparganium plants exhibited extremely weak cyto-toxicity against the growth of mice Lung Adenocarcinoma
795 cell lines with an IC50
value of 116 120583gmL [66] SnS-2oligosaccharides mixture including raffinose (3) stachyose(19) and verbascose (21) from the roots of Scrophularianingpoensis had antitumor activity against the growth ofLewis pulmonary carcinoma cells transplanted into mice[18]
Disaccharide esters and oligosaccharides mixture fromthe Liliaceae Polygonaceae Sparganiaceae and Scrpophular-iaceae families showed effective cytotoxic and antineoplasticactivities The study results indicated that feruloyl and acetylgroups play an important role in mediating cytotoxicitywhich seems to be related to the substitution position offeruloyl groups The feruloyl groups at C-6 or C-11015840 are vitalfor cytotoxicity In addition the increased number of acetylgroups could induce higher tumoricidal activity
16 Evidence-Based Complementary and Alternative Medicine
Table 6 Phenylpropanoid-derived pentasaccharide esters
Number Name R1 R2 R3 R4 R5 R6 Source Parts Reference160 Tenuifoliose A G D I Ac Ac Ac Polygala tenuifolia Roots [38 42]161 Tenuifoliose B G D I H Ac Ac Polygala tenuifolia Roots [42]162 Tenuifoliose C G D I H H H Polygala tenuifolia Roots [42]163 Tenuifoliose F G D U Ac Ac Ac Polygala tenuifolia Roots [42]164 Tenuifoliose G G D U Ac H Ac Polygala tenuifolia Roots [42]165 Tenuifoliose H G D G Ac Ac Ac Polygala tenuifolia Roots [38 42 79]166 Tenuifoliose I G D G Ac H Ac Polygala tenuifolia Roots [42 79]167 Tenuifoliose J G D G H Ac Ac Polygala tenuifolia Roots [42]168 Tenuifoliose K G D G H H Ac Polygala tenuifolia Roots [42]169 Tenuifoliose L G D T Ac Ac Ac Polygala tenuifolia Roots [42 79]170 Tenuifoliose M G D T Ac H Ac Polygala tenuifolia Roots [42]171 Tenuifoliose N I D I Ac Ac Ac Polygala tenuifolia Roots [42]172 Tenuifoliose O I D I H Ac Ac Polygala tenuifolia Roots [42]173 Tenuifoliose P I D I H H Ac Polygala tenuifolia Roots [42]174 Tenuifoliose Q G D T H Ac Ac Polygala tenuifolia Roots [79]175 Tenuifoliose S G D G H H H Polygala tenuifolia Roots [42]176 Tenuifoliose T G D I H H H Polygala tenuifolia Roots [42]177 Tenuifoliose V H D I Ac Ac Ac Polygala tenuifolia Roots [42]178 Tenuifoliose W I D U Ac H Ac Polygala tenuifolia Roots [42]179 Tenuifoliose X I D I H H H Polygala tenuifolia Roots [42]See Scheme 6
O
OO
O
O
O
O
OR1
OH
OH
OH
OHOH
OH
HOHO
HO
HO
OR2
R3O
CH2OH
Scheme 5
34 Anti-Inflammatory Activity Inflammation an importantbasic pathological process is a defense response of biopsywith vascular system to damage stimuli such as pathogensimpaired cells and tissues and physical and chemical factorsHowever if the process of inflammatory response cannot endnormally when cell debris and pathogens were cleared thebiological defence response will become causative factor andbring about many diseases such as diabetes cardiovasculardiseases metabolic syndrome and cancer [100 101]
Tenuifoliside A (44) from the Polygala genus exhibitedstrong anti-inflammatory effect not only by suppressing the
production of NO but also by reducing the production ofiNOS prostaglandin E2 cyclooxygenase-2 and proinflam-matory cytokines through the inhibition of the mitogen-activated protein kinases pathway and NF-120581B pathway [102]The anti-inflammatory activities of quiquesetinerviusides D(108) and E (109) from the Calamus genus were evaluated inRAW 2647 cells Both of them showed significant inhibitoryeffects against the production of LPS-stimulated NOwith theIC50values of 90ndash295120583M [70]Six disaccharide fatty acid esters (132ndash137) were iso-
lated from the Astragalus and Equisetum genera The anti-inflammatory effects of these isolated compounds have alsobeen documented The activation of NF-120581B could upregulatethe expression of proinflammatory cytokines inducible nitricoxide synthase (iNOS) and tumornecrosis factor alpha (TNF-120572) The NF-120581B inhibitory activities of compounds 132ndash137were tested in HepG2 cells stimulated with TNF-120572 All ofthese compounds could significantly restrainTNF-120572-inducedNF-120581B transcriptional activities with the IC
50values of 44ndash
247 120583M Li et al pointed out that olefinic bonds and thelength of the fatty acid moieties contributed to the NF-120581B inhibitory activity Furthermore the inhibition increasedsignificantly with the increase of the number of olefinic bondson the aliphatic moiety [77] These results may provide ascientific basis for the development of new anti-inflammatoryagents
35 Neuroprotective and Cerebral Protective Activities Aswe all know glutamate works as a major excitatory aminoacid neurotransmitter in the mammalian central nervous
Evidence-Based Complementary and Alternative Medicine 17
R6O
R2O
OR3
OR5
OR4
CH2OR1
OCH3
Rham
OO
O
OO O
O
O
O
OO
RhamO
O
OH
OH
OHOH
OH
OHOH
OHHO
HO
HO
T O-rhamnosyl-coumaroyl U O-rhamnosyl-feruloyl
Scheme 6
system and plays a crucial role in several physiological pro-cesses [103] However the accumulation of glutamate inducesdiverse acute and chronic neurodegenerative diseases suchas epilepsy ischemic stroke and Parkinsonrsquos disease aswell as Alzheimerrsquos disease [104] DISS (123) isolated fromthe Polygala genus exhibited neuroprotective effect againstglutamate-induced SH-SY5Y neuronal cell damage The invitro test demonstrated that DISS (06 6 and 60 120583molL)played a critical role in increasing cell viability controllinglactate dehydrogenase and attenuated apoptosis ranging from195 to 258 [105]
Tenuifoliside B (102) from the Polygala genus was ableto significantly shorten the coma time of KCN-inducedanoxia mice at the doses of 3 and 10mgkg and it playedan important role in ameliorating the scopolamine-inducedimpairment of performance in passive avoidance task inrats and enhancing the tremors induced by oxotremorine inmiceThese results together demonstrated that tenuifoliside Bpossessed cognitive improving and cerebral protective effects[56]
36 Antidiabetic Activity Diabetes mellitus a chronic debil-itating metabolic disease is characterized by high bloodglucose content and comprises three types termed type Itype II and gestational diabetes [106] Stachyose (19) extract(a part) from Rehmannia glutinosa obviously exhibited theactivity of downregulating fasting plasma glucose level andpartially keeping from hyperglycemia induced by adrenalineand glucose without obvious dose-dependent effect Otherthan that in vivo tests in rats induced by alloxan revealed
that stachyose extract at the dose of 200mgkg significantlydecreased blood-sugar level [15]
Diboside A lapathosides C and D vanicosides A andB and hydropiperoside were isolated from the FagopyrumPolygonum and Persicaria genera belonging to the Polygo-naceae family Diboside A (116) could potentially inhibit 120572-amylase activity with an IC
50of 269 120583M and thus retard the
starch digestion rate which is helpful for diabetic individualsin controlling blood sugar level [107] Lapathoside D (38)exerted stronger activity of 120572-glucosidase inhibition with anIC50
value of 0113mM than acarbose which was chosen asa positive drug for the treatment of type II diabetes [43]Vanicoside B (111) was reported to have higher 120573-glucosidaseinhibitory activity with an IC
50of 505 120583M than vanicoside A
(110) with an IC50of 599 120583M because of the acetyl moiety of
the latter possibly decreasing inhibitory activity of vanicosideA [71]
Fujimoto et al investigated the inhibitory effects ofmumeoses FndashO (83ndash92) from the Prunus genus on aldosereductase and discovered that caffeoyl groups are crucialfor the inhibitory effect on aldose reductase And thusmumeoses F G H J K L M and N (IC
50= 22ndash77120583M) with
a coumaroyl group and acetyl groups inhibited moderatelyaldose reductase from reducing glucose to sorbitol whichis associated with the chronic complications of diabetes [6364]
37 Elicitors and Regulators Oligosaccharides are quitepropitious for encoding biological information because ofdiverse monosaccharide units and complex molecular struc-tures and they are therefore first described as biological
18 Evidence-Based Complementary and Alternative Medicine
181 H
H
H
H
H
H
H
H
H H
H
H
H
H
H
H
H H
HH
Benzyl
Benzyl
Benzyl
182
183
184 Ac
Ac
Ac
Ac
Ac
Ac
Ac
Ac
Ac
Ac
185
186
187
188
189
R1 R2 R3
R1 R2 R3 R4
OCH3
R3OH2C OR2
OR1
OR1
O
O
O
O O
OOO
O
OO
O
OH
OH
OH OH
OH
O O
O
O
OH
HO
OH
OH OHOH
OH
OH
OHHO
HO
OH
OH
HO
CH2OH
CH2OH
CH2OH
CH2OH
C
R2O
R3O
CH2OR4
CH2CH2 CH2CH2CH2CH2CH3
CH3
CH3
191190 192
193
O
C C
O
OO
OO
OO
OO
O O
O
O
O
O
O
O
OH
OH
OHHO
HO
HOOH
OH
OH
OH
HO
OH
OH
OH
OH
HO
HO
C C
R998400O
R998400
Figure 6
signals in plants [108] Oligosaccharides from the cell wallfragments of plants and fungi are powerful signal moleculessuch as the elicitors of plant defence response and theregulators of plant growth and they are capable of exertingbiological activities at exceedingly low concentrations [109]Heptasaccharide (HS) (15) and octasaccharide (OS) (16) iso-lated from the Paris genus possessed plant growth-regulatory
activities [29 30]The two oligosaccharides significantly pro-moted the proliferation of Paris polyphylla var yunnanensisroots at the doses of 25ndash20mgL The octasaccharide hadthe most obvious effect on the growth of Panax japonicusvar major hairy roots at a dose of 30mgL while the otherhad the most positive effect on saponin accumulation ofPanax japonicus var major hairy roots at a dose of 10mgL
Evidence-Based Complementary and Alternative Medicine 19
[29] Similarly Zhou et al evaluated the stimulating effectsof HS and OS on the root growth and saponin productionof Panax ginseng hairy roots which were induced from theplant roots infected withAgrobacterium rhizogenes strain A4The results showed that there was a maximum effect on thehairy roots growth and saponin accumulation on day 10Compared with control group the root biomass dry weightwas increased by more than 17-fold while the total saponincontent of roots increased by more than 1-fold when thesetwo oligosaccharides were added to the hairy root at a dose of30mgL [30] The above data illustrate that HS and OS couldserve as the plant growth-regulators not only in their originalspecies but also in others
38 Immunopotentiating Activity Macrophages are impor-tant targets of investigations on cytophagy cellular immunityand molecular immunology Therefore they are deemedto play a vital role in host defense comprising phagocy-tosis proteolytic processing pathogenic agent apoptosiscytokines production and foreign antigens presentation[110] The water-extracted oligosaccharides from Panax gin-seng (WGOS) exhibited better immunopotentiating activ-ity by increasing phagocytic function of macrophages andpromoting NO TNF-120572 and reactive oxygen species pro-duction [110] In addition Wan et al have obtained malto-oligosaccharides (17 119899 = 3sim8) and three oligosaccharides (213 14) from the Panax ginseng roots The in vitro bioassaypointed out thatWGOS could serve as efficacious stimulatorsof B and T lymphocytes [28] These studies provided enlight-enment that the mixture of oligosaccharides from Chineseherbalmedicine exhibits significant effect on immune system
39 Others Acetylcholinesterase (AChE) inhibitors showgood therapeutic effects onmyasthenia gravis glaucoma andAlzheimerrsquos disease through reversible enzyme inhibitionso as to increase the accumulation of acetylcholine in thesynapse and then promote and prolong the function ofacetylcholine Vanicoside B (111) showed AChE inhibitoryactivity with an IC
50of 0062mM while hydropiperoside
(42) and lapathosides C (115) and D (38) just exhibited weakenzyme inhibitory activity [43]
Wang et al has explored low molecular mass carbohy-drate polymer from Panax ginseng roots and obtained 30ethanol elution (PGO)which included peptides and oligosac-charides (17 119899 = 0sim5) identified as maltose maltotriosemaltotetraose maltopentaose maltohexaose and maltohep-taose Pharmacological experiments revealed that PGO couldsignificantly enhance the memory in scopolamine-inducedmemory deficit rats [27]
Cistanoside F (129) and kankanose (150) were isolatedfrom the Cistanche Paulownia and Acanthus genera Phar-macological experiments showed that cistanoside F andkankanose significantly exhibited vasorelaxant effects on thenoradrenaline-induced contraction of thoracic aorta fromrats [80]
4 Conclusion
Traditional Chinese medicine from natural kingdom playsan indelible role in the treatment of human diseases andit has aroused the attention of those who have engagedin medicinal pharmaceutical chemistry Therefore scientistshave made great contributions day after day to investigate thevalid chemicals from traditional Chinese medicines In thepast decades about 193 oligosaccharides and their esters havebeen identified from traditional Chinese medicinal plantsOn the one hand only a few oligosaccharides and theirmixtures were investigated and just exhibited antidepres-sant antineoplastic antidiabetic plant growth-regulatoryimmunopotentiating and enhancedmemory activitiesMoreexploratory work is still needed to excavate biological andpharmacological activities of oligosaccharides On the otherhand oligosaccharide esters exhibited multi-advantageousactivities Bioassays have revealed that antioxidant cytotoxicantineoplastic and anti-inflammatory activities are the mostnotable bioactivities Of course to search for the naturalproducts with these activities is a hotpot in the contemporarydrug research Oligosaccharide esters provide a vast treasuretrove for medical researchers After considering the currentstudies it should be taken as future directions to makemore mechanism of action studies and clinical trials tofurther evaluate its potential as new drugs Moreover thestructure-activity relationships discussed in this review willprovide reference information for further exploring theirrelationships and continually discovering the new bioactiveoligosaccharide esters
Conflict of Interests
The authors declare that there is no conflict of interestsregarding the publication of this paper
References
[1] X D Yang L J Zhang B Liang L Z Xu and S L YangldquoOligosaccharide esters isolated from plants of PolygalaceaerdquoChinese Traditional and Herbal Drugs vol 33 no 10 pp 954ndash958 2002
[2] N Ogwuru and M Adamczeski ldquoBioactive natural productsderived from Polygonum species of plants their structures andmechanisms of actionrdquo Studies in Natural Products Chemistryvol 22 pp 607ndash642 2000
[3] S Kobayashi T Miyase and H Noguchi ldquoPolyphenolic glyco-sides and oligosaccharide multiesters from the roots of Polygaladalmaisianardquo Journal of Natural Products vol 65 no 3 pp 319ndash328 2002
[4] M Takasaki S Kuroki M Kozuka and T Konoshima ldquoNewphenylpropanoid esters of sucrose from Polygonum lapathi-foliumrdquo Journal of Natural Products vol 64 no 10 pp 1305ndash1308 2001
[5] M L Zimmermann and A T Sneden ldquoVanicosides A and Bprotein kinase C inhibitors from Polygonum pensylvanicumrdquoJournal of Natural Products vol 57 no 2 pp 236ndash242 1994
[6] M Takasaki T Konoshima S Kuroki H Tokuda and HNishino ldquoCancer chemopreventive activity of phenylpropanoid
20 Evidence-Based Complementary and Alternative Medicine
esters of sucrose vanicoside B and lapathoside A from Poly-gonum lapathifoliumrdquo Cancer Letters vol 173 no 2 pp 133ndash138 2001
[7] Q Fu T Liang Z Y Li et al ldquoSeparation of carbohydrates usinghydrophilic interaction liquid chromatographyrdquo CarbohydrateResearch vol 379 pp 13ndash17 2013
[8] M F Mrozek D Zhang and D Ben-Amotz ldquoOligosaccharideidentification and mixture quantification using Raman spec-troscopy and chemometric analysisrdquo Carbohydrate Researchvol 339 no 1 pp 141ndash145 2004
[9] G S Armstrong and B Bendiak ldquoHigh-resolution four-dimen-sional carbon-correlated 1H-1H ROESY experiments employ-ing isotags and the filter diagonalization method for effectiveassignment of glycosidic linkages in oligosaccharidesrdquo Journalof Magnetic Resonance vol 181 no 1 pp 79ndash88 2006
[10] G S Armstrong V A Mandelshtam A J Shaka and BBendiak ldquoRapid high-resolution four-dimensional NMR spec-troscopy using the filter diagonalization method and its advan-tages for detailed structural elucidation of oligosaccharidesrdquoJournal of Magnetic Resonance vol 173 no 1 pp 160ndash168 2005
[11] H-M Tseng S Gattolin J Pritchard H J Newbury and DA Barrett ldquoAnalysis of mono- di- and oligosaccharides by CEusing a two-stage derivatization method and LIF detectionrdquoElectrophoresis vol 30 no 8 pp 1399ndash1405 2009
[12] N Li X Li B L Hou and D L Meng ldquoNew disaccharosidefrom Camptosorus sibiricus Ruprrdquo Natural Product Researchvol 22 no 15 pp 1379ndash1383 2008
[13] Z Zhang D Wang Y Zhao H Gao Y-H Hu and J-FHu ldquoFructose-derived carbohydrates from Alisma orientalisrdquoNatural Product Research vol 23 no 11 pp 1013ndash1020 2009
[14] X Yang Y Zhao N He and K D Croft ldquoIsolation char-acterization and immunological effects of 120572-galacto-oligo-saccharides from a new source the herb Lycopus lucidus TurczrdquoJournal of Agricultural and Food Chemistry vol 58 no 14 pp8253ndash8258 2010
[15] R X Zhang Z P Jia L Y Kong et al ldquoStachyose extractfrom Rehmannia glutinosa Libosch to lower plasma glucose innormal and diabetic rats by oral administrationrdquo Pharmazievol 59 no 7 pp 552ndash556 2004
[16] R Zhang Y Zhao Y Sun X Lu and X Yang ldquoIsolationcharacterization and hepatoprotective effects of the raffinosefamily oligosaccharides from Rehmannia glutinosa liboschrdquoJournal of Agricultural and Food Chemistry vol 61 no 32 pp7786ndash7793 2013
[17] H Li F Song Z Zheng Z Liu and S Liu ldquoCharacterization ofsaccharides and phenolic acids in the Chinese herb Tanshen byESI-FT-ICR-MS and HPLCrdquo Journal of Mass Spectrometry vol43 no 11 pp 1545ndash1552 2008
[18] J E Deng J Zhang XM ChenW Ke and G Y Tian ldquoStudieson the physicochemical properties structure and antitumoractivity of an oligosaccharide homologue SnS-2 from the root ofScrophularia ningpoensis Hemslrdquo Chinese Journal of Chemistryvol 22 no 5 pp 492ndash497 2004
[19] S C Chou LM Chuang and S S Lee ldquoHypoglycemic constit-uents of gynura divaricata subsp formosanardquo Natural ProductCommunications vol 7 no 2 pp 221ndash222 2012
[20] F Feng L-L Wang X-P Lai Y-B Li Z-M Cao and Y-J Zhou ldquoStudy on oligosaccharides from Morinda officinalisrdquoJournal of Chinese Medicinal Materials vol 35 no 8 pp 1259ndash1262 2012
[21] Y F Li Z H Gong M Yang Y M Zhao and Z P Luo ldquoInhibi-tion of the oligosaccharides extracted fromMorinda officinalis
a Chinese traditional herbal medicine on the corticosteroneinduced apoptosis in PC12 cellsrdquo Life Sciences vol 72 no 8 pp933ndash942 2003
[22] Y-F Li Y-Q Liu M Yang et al ldquoThe cytoprotective effect ofinulin-type hexasaccharide extracted from Morinda officinalison PC12 cells against the lesion induced by corticosteronerdquo LifeSciences vol 75 no 13 pp 1531ndash1538 2004
[23] D N Olennikov L M Tankhaeva and A V Rokhin ldquoGlu-cofructans from Saussurea lappa rootsrdquo Chemistry of NaturalCompounds vol 47 no 3 pp 339ndash342 2011
[24] S K Hyun H A Jung B S Min J H Jung and J S ChoildquoIsolation of phenolics nucleosides saccharides and an alkaloidfrom the root of Aralia cordatardquo Natural Product Sciences vol16 no 1 pp 20ndash25 2010
[25] Z J Xu C W Lin and M F Liao ldquoStructure analysis of a newoligosaccharides BROS from Blumea ripariardquo Chinese Journalof Organic Chemistry vol 31 no 11 pp 1811ndash1819 2011
[26] Z J Xu C W Lin and Y Shi ldquoIsolation and structuredetermination of a new oligosaccharide from Blume ripariardquoJournal of Medicinal Plants Research vol 5 no 14 pp 2956ndash2962 2011
[27] Y Wang R Z Jiang G R Li et al ldquoStructural and enhancedmemory activity studies of extracts from Panax ginseng rootrdquoFood Chemistry vol 119 no 3 pp 969ndash973 2010
[28] DWan L Jiao H Yang and S Liu ldquoStructural characterizationand immunological activities of the water-soluble oligosaccha-rides isolated from thePanax ginseng rootsrdquoPlanta vol 235 no6 pp 1289ndash1297 2012
[29] L G Zhou C Z Yang J Q Li S L Wang and J Y WuldquoHeptasaccharide and octasaccharide isolated from Paris pol-yphylla var yunnanensis and their plant growth-regulatoryactivityrdquo Plant Science vol 165 no 3 pp 571ndash575 2003
[30] L G Zhou X D Cao R F Zhang Y L Peng S J Zhao andJ Y Wu ldquoStimulation of saponin production in Panax ginsenghairy roots by two oligosaccharides from Paris polyphylla varyunnanensisrdquo Biotechnology Letters vol 29 no 4 pp 631ndash6342007
[31] M Vanhaecke W van den Ende E Lescrinier and N Dyu-bankova ldquoIsolation and characterization of a pentasaccharidefrom Stellaria mediardquo Journal of Natural Products vol 71 no 11pp 1833ndash1836 2008
[32] J Feng and W Zhao ldquoComplete 1Hand 13C NMR assignmentsof four new oligosaccharides and two new glycosides fromPeriploca forrestiirdquoMagnetic Resonance in Chemistry vol 47 no8 pp 701ndash705 2009
[33] J Q Feng R J Zhang Y Zhou et al ldquoImmunosuppressive preg-nane glycosides from Periploca sepium and Periploca forrestiirdquoPhytochemistry vol 69 no 15 pp 2716ndash2723 2008
[34] X H Long R Xu Y H Zhang X H Tan andQ Y Sun ldquoA newoligosaccharide from Periploca calophyllardquo Zhongguo ZhongyaoZazhi vol 37 no 2 pp 226ndash229 2012
[35] L Wang Z-Q Yin Y Wang X-Q Zhang Y-L Li and W-CYe ldquoPerisesaccharides A-E new oligosaccharides from the rootbarks ofPeriploca sepiumrdquoPlantaMedica vol 76 no 9 pp 909ndash915 2010
[36] T Lei L Zhang H-Y Jiang Y Hu A-H Hong and Y-Z CenldquoA new pregnane glycoside and oligosaccharide from Parabar-ium huaitingiirdquo Journal of Asian Natural Products Research vol13 no 11 pp 1030ndash1035 2011
[37] J Li Y Jiang and P F Tu ldquoTricornoses A-L oligosaccharidemulti-esters from the roots of Polygala tricornisrdquo Journal ofNatural Products vol 68 no 5 pp 739ndash744 2005
Evidence-Based Complementary and Alternative Medicine 21
[38] H H Tu P Liu L Mu et al ldquoStudy on antidepressant com-ponents of sucrose ester from Polygala tenuifoliardquo ZhongguoZhongyao Zazhi vol 33 no 11 pp 1278ndash1280 2008
[39] G M She Y Y Ba Y Liu H Lv W Wang and R B ShildquoAbsorbable phenylpropenoyl sucroses from Polygala tenuifo-liardquoMolecules vol 16 no 7 pp 5507ndash5513 2011
[40] J Yong and P F Tu ldquoStudies on the chemical constituents inroot bark of Polygala tenuifolia (II)rdquo China Journal of ChineseMateria Medica vol 29 no 8 pp 751ndash753 2004
[41] M Ono C Takamura F Sugita et al ldquoTwo new steroidglycosides and a new sesquiterpenoid glycoside from theunderground parts of Trillium kamtschaticumrdquo Chemical andPharmaceutical Bulletin vol 55 no 4 pp 551ndash556 2007
[42] Y Ling Z Li M Chen Z Sun M Fan and C HuangldquoAnalysis and detection of the chemical constituents of RadixPolygalae and their metabolites in rats after oral administrationby ultra high-performance liquid chromatography coupledwith electrospray ionization quadrupole time-of-flight tandemmass spectrometryrdquo Journal of Pharmaceutical and BiomedicalAnalysis vol 85 pp 1ndash13 2013
[43] P Fan L Terrier A-E Hay A Marston and K HostettmannldquoAntioxidant and enzyme inhibition activities and chemicalprofiles ofPolygonum sachalinensis FSchmidt exMaxim (Polyg-onaceae)rdquo Fitoterapia vol 81 no 2 pp 124ndash131 2010
[44] L J Zhang C C Liao H C Huang Y C Shen L M Yangand Y H Kuo ldquoAntioxidant phenylpropanoid glycosides fromSmilax bracteatardquo Phytochemistry vol 69 no 6 pp 1398ndash14042008
[45] L L Yan W Y Gao Y J Zhang and Y Wang ldquoA new phenyl-propanoid glycosides from Paris polyphylla var yunnanensisrdquoFitoterapia vol 79 no 4 pp 306ndash307 2008
[46] Y H Kuo Y W Hsu C C Liaw J K Lee H C Huang andL M Y Kuo ldquoCytotoxic phenylpropanoid glycosides from thestems of Smilax chinardquo Journal of Natural Products vol 68 no10 pp 1475ndash1478 2005
[47] W-X Wang T-X Li H Ma J-F Zhang and A-Q JialdquoTumoral cytotoxic and antioxidative phenylpropanoid glyco-sides in Smilax riparia A DCrdquo Journal of Ethnopharmacologyvol 149 no 2 pp 527ndash532 2013
[48] N X Nhiem P vanKiem C vanMinh et al ldquoPhenylpropanoidglycosides fromHeterosmilax erythrantha and their antioxidantactivityrdquo Archives of Pharmacal Research vol 32 no 10 pp1373ndash1377 2009
[49] Y Wang W Y Gao T J Zhang and Y Q Guo ldquoA novelphenylpropanoid glycosides and a new derivation of phenolicglycoside from Paris Polyphylla var yunnanensisrdquo ChineseChemical Letters vol 18 no 5 pp 548ndash550 2007
[50] J-Y Zhang Y-Z Wang Y-L Zhao et al ldquoPhytochemicals andbioactivities of Paris speciesrdquo Journal of Asian Natural ProductsResearch vol 13 no 7 pp 670ndash681 2011
[51] N H N Hashim F Abas K Shaari and N H Lajis ldquoLC-DAD-ESIMSMS characterization of antioxidant and anti-cholinesterase constituents present in the active fraction fromPersicaria hydropiperrdquo LWT Food Science and Technology vol46 no 2 pp 468ndash476 2012
[52] PH FanA EHayAMarstonHX Lou andKHostettmannldquoChemical variability of the invasive neophytes Polygonumcuspidatum Sieb and Zucc and Polygonum sachalinensis FSchmidt ex Maximrdquo Biochemical Systematics and Ecology vol37 no 1 pp 24ndash34 2009
[53] P Liu Y Hu D H Guo et al ldquoPotential antidepressantproperties of Radix Polygalae (Yuan Zhi)rdquo Phytomedicine vol17 no 10 pp 794ndash799 2010
[54] J F Wu S B Chen S L Chen and P F Tu ldquoThe chemical con-stituents of Polygala hongkongensisHemslrdquoActa PharmaceuticaSinica vol 42 no 7 pp 757ndash761 2007
[55] Y Song Y Jiang D Bi X Tian L Liang and P Tu ldquoChemicalconstituents from n-butanol extract of aerial part of Polygalasibiricardquo Zhongguo Zhongyao Zazhi vol 37 no 4 pp 471ndash4742012
[56] Y Ikeya S Takeda M Tunakawa et al ldquoCognitive improvingand cerebral protective effects of acylated oligosaccharides inPolygala tenuifoliardquo Biological and Pharmaceutical Bulletin vol27 no 7 pp 1081ndash1085 2004
[57] C J Zheng C L Hu X Q Ma C Peng H Zhang and L PQin ldquoCytotoxic phenylpropanoid glycosides from Fagopyrumtataricum (L) Gaertnrdquo Food Chemistry vol 132 no 1 pp 433ndash438 2012
[58] X Li Y F Zhang L Yang et al ldquoChemical profiling ofconstituents of Smilacis glabrae using ultra-high pressure liquidchromatography coupled with LTQ orbitrap mass spectrome-tryrdquo Natural Product Communications vol 7 no 2 pp 181ndash1842012
[59] T-T Sun D-W Zhang Y Han F-Y Dong andWWang ldquoSmi-lasides M and N two new phenylpropanoid glycosides fromSmilax ripariardquo Journal of Asian Natural Products Research vol14 no 2 pp 165ndash170 2012
[60] J Li X Bi G Zheng Y Hitoshi T Ikeda and T NoharaldquoSteroidal glycosides and aromatic compounds from Smilaxripariardquo Chemical amp Pharmaceutical Bulletin vol 54 no 10 pp1451ndash1454 2006
[61] N Wang X Yao R Ishii and S Kitanaka ldquoBioactive sucroseesters from Bidens parviflorardquo Phytochemistry vol 62 no 5 pp741ndash746 2003
[62] S Nakamura K Fujimoto T Matsumoto et al ldquoAcylatedsucroses and acylated quinic acids analogs from the flower budsof Prunus mume and their inhibitory effect on melanogenesisrdquoPhytochemistry vol 92 pp 128ndash136 2013
[63] K Fujimoto SNakamura TMatsumoto et al ldquoMedicinal flow-ers XXXVIII Structures of acylated sucroses and inhibitoryeffects of constituents on aldose reducatase from the flower budsofPrunusmumerdquoChemical and Pharmaceutical Bulletin vol 61no 4 pp 445ndash451 2013
[64] S Nakamura K Fujimoto T Matsumoto et al ldquoStructuresof acylated sucroses and an acylated flavonol glycoside andinhibitory effects of constituents on aldose reductase from theflower buds of Prunus mumerdquo Journal of Natural Medicines vol67 no 4 pp 799ndash806 2013
[65] L-B Dong J He X-Y Li et al ldquoChemical constituents fromthe aerial parts of Musella lasiocarpardquo Natural Products andBioprospecting vol 1 no 1 pp 41ndash47 2011
[66] Y Xiong K Z Deng Y Q Guo W Y Gao and T J ZhangldquoNew chemical constituents from the rhizomes of Sparganiumstoloniferumrdquo Archives of Pharmacal Research vol 32 no 5 pp717ndash720 2009
[67] Y Xiong K-Z Deng Y-Q Guo W-Y Gao and T-J ZhangldquoTwo new sucrose esters from Sparganium stoloniferumrdquo Jour-nal of Asian Natural Products Research vol 10 no 5 pp 425ndash428 2008
[68] B Chen N L Wang J H Huang and X S Yao ldquoIridoidand phenylpropanoid glycosides from Scrophularia ningpoensis
22 Evidence-Based Complementary and Alternative Medicine
Hemslrdquo Asian Journal of Traditional Medicines vol 2 no 3 pp119ndash123 2007
[69] H Chen Y Z Zhou L Qiao et al ldquoTwo new compounds fromCynanchum amplexicaulerdquo Journal of Asian Natural ProductsResearch vol 10 no 3 pp 248ndash251 2008
[70] C-L Chang L-J Zhang R Y Chen et al ldquoAntioxidant andanti-inflammatory phenylpropanoid derivatives from Calamusquiquesetinerviusrdquo Journal of Natural Products vol 73 no 9 pp1482ndash1488 2010
[71] Y Kawai H Kumagai H Kurihara K Yamazaki R Sawanoand N Inoue ldquo120573-Glucosidase inhibitory activities of phenyl-propanoid glycosides vanicoside A and B from Polygonumsachalinense rhizomerdquo Fitoterapia vol 77 no 6 pp 456ndash4592006
[72] P V Kiem N X Nhiem N X Cuong et al ldquoNew phenyl-propanoid esters of sucrose from Polygonum hydropiper andtheir antioxidant activityrdquo Archives of Pharmacal Research vol31 no 11 pp 1477ndash1482 2008
[73] K J Wang Y J Zhang and C R Yang ldquoAntioxidant phenolicconstituents from Fagopyrum dibotrysrdquo Journal of Ethnophar-macology vol 99 no 2 pp 259ndash264 2005
[74] N Cho J Huh H Yang et al ldquoChemical constituentsof Polygala tenuifolia roots and their inhibitory activity onlipopolysaccharide-induced nitric oxide production in BV2microgliardquo Journal of Enzyme Inhibition and Medicinal Chem-istry vol 27 no 1 pp 1ndash4 2012
[75] Q Ren C S Wu and J L Zhang ldquoUse of on-line stop-flowheart-cutting two-dimensional high performance liquid chro-matography for simultaneous determination of 12 major con-stituents in tartary buckwheat (Fagopyrum tataricum Gaertn)rdquoJournal of Chromatography A vol 1304 pp 257ndash262 2013
[76] Q Ren C S Wu Y Ren and J L Zhang ldquoCharacterizationand identification of the chemical constituents from tartarybuckwheat (Fagopyrum tataricumGaertn) by high performanceliquid chromatographyphotodiode array detectorlinear iontrap FTICR hybrid mass spectrometryrdquo Food Chemistry vol136 no 3-4 pp 1377ndash1389 2013
[77] W Li Y N Sun X T Yan et al ldquoNF-120581B inhibitory activityof sucrose fatty acid esters and related constituents fromAstragalus membranaceusrdquo Journal of Agricultural and FoodChemistry vol 61 no 29 pp 7081ndash7088 2013
[78] J T Cheng J He Y Li et al ldquoThree new sucrose fatty acid estersfrom Equisetum hiemale LrdquoHelvetica Chimica Acta vol 95 no7 pp 1158ndash1163 2012
[79] Y Jiang and P-F Tu ldquoTenuifoliose Q a new oligosaccharideester from the root of Polygala tenuifoliaWilldrdquo Journal of AsianNatural Products Research vol 5 no 4 pp 279ndash283 2003
[80] M Yoshikawa H Matsuda T Morikawa H H Xie S Naka-mura and O Muraoka ldquoPhenylethanoid oligoglycosides andacylated oligosugars with vasorelaxant activity from Cistanchetubulosardquo Bioorganic ampMedicinal Chemistry vol 14 no 22 pp7468ndash7475 2006
[81] P-F Tu H-M Shi Z-H Song Y Jiang and Y-Y ZhaoldquoChemical constituents of Cistanche sinensisrdquo Journal of AsianNatural Products Research vol 9 no 1 pp 79ndash84 2007
[82] C-L Si Y-Y Lu P-P Qin R-C Sun and Y-H Ni ldquoPhenolicextractives with chemotaxonomic significance from the bark ofPaulownia tomentosa var tomentosardquo BioResources vol 6 no4 pp 5086ndash5098 2011
[83] J Wu S Zhang Q Xiao et al ldquoPhenylethanoid and aliphaticalcohol glycosides from Acanthus ilicifoliusrdquo Phytochemistryvol 63 no 4 pp 491ndash495 2003
[84] Y Jiang and P-F Tu ldquoAnalysis of chemical constituents inCistanche speciesrdquo Journal of Chromatography A vol 1216 no11 pp 1970ndash1979 2009
[85] H Otsuka H Kuwabara and H Hoshiyama ldquoIdentification ofsucrose diesters of aryldihydronaphthalene-type lignans fromTrigonotis peduncularisand the nature of their fluorescencerdquoJournal of Natural Products vol 71 no 7 pp 1178ndash1181 2008
[86] M-R Suo J-S Yang and Q-H Liu ldquoLignan oligosaccharideesters from Eritrichium rupestrerdquo Journal of Natural Productsvol 69 no 4 pp 682ndash684 2006
[87] P-F Tu Z-H Song H-M Shi Y Jiang and Y-Y ZhaoldquoArylethyl (=phenylethanoid) glycosides and oligosaccharidefrom the stem of Cistanche tubulosardquo Helvetica Chimica Actavol 89 no 5 pp 927ndash935 2006
[88] M-H Shyr T-H Tsai and L-C Lin ldquoRossicasins A Band rosicaside F three new phenylpropanoid glycosides fromBoschniakia rossicardquoChemical and Pharmaceutical Bulletin vol54 no 2 pp 252ndash254 2006
[89] R FangNCVeitchGCKiteM J RHowes EA Porter andM S J Simmonds ldquoGlycosylated constituents of Iris fulvaandIris brevicaulisrdquoChemical amp Pharmaceutical Bulletin vol 59 no1 pp 124ndash128 2011
[90] J Fu L Zuo J Yang R Chen and D Zhang ldquoOligosaccharidepolyester and triterpenoid saponins from the roots of Polygalajaponicardquo Phytochemistry vol 69 no 7 pp 1617ndash1624 2008
[91] M-C Cheng C-Y Li H-C Ko F-N Ko Y-L Lin andT-S Wu ldquoAntidepressant principles of the roots of polygalatenuifoliardquo Journal of Natural Products vol 69 no 9 pp 1305ndash1309 2006
[92] H T Chang and P F Tu ldquoNew oligosaccharide esters andxanthone C-glucosides from Polygala telephioidesrdquo HelveticaChimica Acta vol 90 no 5 pp 944ndash950 2007
[93] J Li L Feng J Dai R Wang and T Nohara ldquoChemical con-stituents from Polygala telephioidesrdquo China Journal of ChineseMateria Medica vol 34 no 4 pp 402ndash405 2009
[94] W-P Yin T-Z Zhao and H-Y Zhang ldquoA novel oligosaccha-ride ester from Syringa pubescensrdquo Journal of Asian NaturalProducts Research vol 10 no 1 pp 95ndash100 2008
[95] M Valko D Leibfritz J Moncol M T D Cronin M Mazurand J Telser ldquoFree radicals and antioxidants in normal physio-logical functions and human diseaserdquoThe International Journalof Biochemistry amp Cell Biology vol 39 no 1 pp 44ndash84 2007
[96] D Krishnaiah R Sarbatly and R Nithyanandam ldquoA review ofthe antioxidant potential of medicinal plant speciesrdquo Food andBioproducts Processing vol 89 no 3 pp 217ndash233 2011
[97] P Liu Y Hu D-H Guo et al ldquoAntioxidant activity ofoligosaccharide ester extracted from Polygala tenuifolia roots insenescence-accelerated micerdquo Pharmaceutical Biology vol 48no 7 pp 828ndash833 2010
[98] Y Hu H-B Liao G Dai-Hong P Liu Y-Y Wang and KRahman ldquoAntidepressant-like effects of 361015840-disinapoyl sucroseon hippocampal neuronal plasticity and neurotrophic signalpathway in chronically mild stressed ratsrdquo NeurochemistryInternational vol 56 no 3 pp 461ndash465 2010
[99] Y Hu H B O Liao P Liu D-H Guo and K RahmanldquoA bioactive compound from Polygala tenuifolia regulatesefficiency of chronic stress on hypothalamic-pituitary-adrenalaxisrdquo Pharmazie vol 64 no 9 pp 605ndash608 2009
[100] A Jungbauer and SMedjakovic ldquoAnti-inflammatory propertiesof culinary herbs and spices that ameliorate the effects ofmetabolic syndromerdquoMaturitas vol 71 no 3 pp 227ndash239 2012
Evidence-Based Complementary and Alternative Medicine 23
[101] Q Xu Y Wang S Guo Z Shen and L Yang ldquoAnti-inflammatory and analgesic activity of aqueous extract of Flospopulirdquo Journal of Ethnopharmacology vol 152 no 3 pp 540ndash545 2014
[102] K S Kim D S Lee G S Bae et al ldquoThe inhibition of JNKMAPK and NF-120581B signaling by tenuifoliside A isolated fromPolygala tenuifolia in lipopolysaccharide-induced macrophagesis associated with its anti-inflammatory effectrdquo European Jour-nal of Pharmacology vol 721 no 1ndash3 pp 267ndash276 2013
[103] J-G Lee J-M Yon C Lin A Y Jung K Y Jung and S-YNamldquoCombined treatment with capsaicin and resveratrol enhancesneuroprotection against glutamate-induced toxicity in mousecerebral cortical neuronsrdquo Food and Chemical Toxicology vol50 no 11 pp 3877ndash3885 2012
[104] M L Jin S Y Park Y H Kim J-I Oh S J Lee andG Park ldquoThe neuroprotective effects of cordycepin inhibitglutamate-induced oxidative andER stress-associated apoptosisin hippocampal HT22 cellsrdquo NeuroToxicology vol 41 pp 102ndash111 2014
[105] P Liu Y Hu J Li et al ldquoProtection of SH-SY5Y neuronal cellsfrom glutamate-induced apoptosis by 36rsquo-disinapoyl sucrosea bioactive compound isolated from radix polygalardquo Journal ofBiomedicine and Biotechnology vol 2012 Article ID 728342 5pages 2012
[106] P-B Li W-L Lin Y-G Wang W Peng X-Y Cai and W-WSu ldquoAntidiabetic activities of oligosaccharides of Ophiopogonisjaponicus in experimental type 2 diabetic ratsrdquo InternationalJournal of Biological Macromolecules vol 51 no 5 pp 749ndash7552012
[107] T Liu Y M Yip L Song et al ldquoInhibiting enzymatic starchdigestion by the phenolic compound diboside A a mechanisticand in silico studyrdquo Food Research International vol 54 no 1pp 595ndash600 2013
[108] F Cote andMGHahn ldquoOligosaccharins structures and signaltransductionrdquo Plant Molecular Biology vol 26 no 5 pp 1379ndash1411 1994
[109] RACreelman and J EMullet ldquoOligosaccharins brassinolidesand jasmonates nontraditional regulators of plant growthdevelopment and gene expressionrdquo Plant Cell vol 9 no 7 pp1211ndash1223 1997
[110] L Jiao D Wan X Zhang B Li H Zhao and S LiuldquoCharacterization and immunostimulating effects on murineperitoneal macrophages of oligosaccharide isolated from Panaxginseng CAMeyerrdquo Journal of Ethnopharmacology vol 144 no3 pp 490ndash496 2012
Submit your manuscripts athttpwwwhindawicom
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Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
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Disease Markers
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
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OncologyJournal of
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Oxidative Medicine and Cellular Longevity
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PPAR Research
The Scientific World JournalHindawi Publishing Corporation httpwwwhindawicom Volume 2014
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Journal of
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Computational and Mathematical Methods in Medicine
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Research and TreatmentAIDS
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Gastroenterology Research and Practice
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Parkinsonrsquos Disease
Evidence-Based Complementary and Alternative Medicine
Volume 2014Hindawi Publishing Corporationhttpwwwhindawicom
4 Evidence-Based Complementary and Alternative Medicine
R1
R2 R3
R4
R5
R6
O OO
OO
O
O
OO
O O OO
O
O
O
OCH3
H3COH3CO
H3CO
A oleandronic acid-120575-lactone B cymaropyranurolactone C oleandronic acid-120575-lactone
Scheme 1
222 Fatty Acid-Derived Disaccharide Esters Eight mono-substituted disaccharide esters (Table 3) with a sucrose moi-ety possess six different types of fatty acid residues whichattach to the 6 or 61015840 position of sucrose These fatty acidsinclude linoleic acid palmitic acid linolenic acid myris-tic acid hexadeca-71013-trienoic acid and hexadeca-710-dienoic acid The above sucrose fatty acid esters have beenfound in the rhizomes of Astragalus membranaceus and theroots of Equisetum hiemale
223 Lignan-DerivedDisaccharide Esters Six lignan-deriveddisaccharide esters (Figure 4) contain a sucrose core esterifiedwith different lignan residues covalently linked to the 31015840and 61015840 positions of 120573-D-fructofuranosyl unit and have beenisolated from the whole parts of Trigonotis peduncularis [85]and the aerial parts of Eritrichium rupestre [86]
224 Phenylpropanoid-Derived Trisaccharide Esters Inthis group all oligosaccharide esters consist of threemonosaccharides including glucopyranose fructofuranoseand rhamnopyranose with O-substituents which compriseferuloyl sinapoyl and 345-trimethoxycinnamoyl groupsOligosaccharide esters (146ndash149) listed in Table 4 as well askankanose (150) cistantubulose A
1A2(151) cistansinensose
A1A2(152) and compound 153 shown in Figure 5 have
been found in the roots of Polygala tricornis [37] the stemsof Cistanche tubulosa [81 87] and C sinensis [80] the wholeparts of Boschniakia rossica [88] and the rhizomes of Irisbrevicaulis [89]
225 Phenylpropanoid-Derived Tetrasaccharide Esters Phe-nylpropanoid-derived tetrasaccharide esters (154ndash159)(Table 5) consisting of three glucopyranosyl units and afructofuranosyl unit have been identified from the rootsof Polygala tricornis The nonsugar moieties of theseoligosaccharides include coumaroyl feruloyl sinapoyl and345-trimethoxycinnamoyl groups
226 Phenylpropanoid-Derived Pentasaccharide Esters Asshown in Table 6 oligosaccharide esters (160-179) possess-ing a skeleton of five sugar residues have been isolatedfrom the roots of Polygala tenuifolia The sugar residues
are composed of two types of monosaccharides includ-ing fructofuranose and glucopyranose which are esterifiedwith acetyl benzoyl rhamnose-substitutednonsubstitutedcoumaroyl and rhamnose-substitutednonsubstituted feru-loyl groups Other than that a structure-complex oligosac-charide polyester shown in Figure 5 polygalajaponicose I(180) consisting of a pentasaccharide backbone esterifiedwith feruloyl coumaroyl rhamnosyl-coumaroyl acetyl andbenzoyl groups has been obtained from the roots of Pjaponica [90]
227 Others Polygalatenosides AndashC (181ndash183) (Figure 6)containing a galactosyl unit and a polygolitosyl unit esterifiedwith benzoyl groups at 3 4 and 6 positions have been foundin the roots of Polygala tenuifolia [91] Three sucrose estersincluding polygalatenoside D (190) telephiose F (191) and6-O-benzoylsucrose (192) possess one benzoyl group twobenzoyl groups and a p-methoxybenzoyl group respectivelyThey were isolated from the roots of P tenuifolia [91] thewhole plants of P telephioides [92] and the roots of P tricornis[37] Six trisaccharide esters named telephioses AndashE and G(184ndash189) with substituents of acetyl and benzoyl groupswere isolated from the whole plants of P telephioides [92 93]Moreover a trisaccharide ester (193) pubescenside A fromthe flowers of Syringa pubescens possesses a fatty acid residue[94]
3 Biological Activities ofOligosaccharides and Their Esters
The oligosaccharides and oligosaccharide esters from Chi-nese medicinal plants are important products with diver-sified structures which have triggered an increasing num-ber of studies carried out on the isolated compoundsAnd thus diverse pharmacological activities have beenproved Among the isolated compounds oligosaccharidesphenylpropanoid-derived disaccharide esters and trisaccha-ride esters fatty acid-derived disaccharide esters and othersfrom the families Polygonaceae Asclepiadaceae RubiaceaePolygalaceae Liliaceae Smilacaceae Arecaceae Oroban-chaceae Scrophulariaceae Acanthaceae Rosaceae Sparga-niaceae Leguminosae and Equisetaceae have shown sig-nificant pharmacological activities including antioxidant
Evidence-Based Complementary and Alternative Medicine 5
1 2 3 4
5 6 7 8
9 10 11 12
13 14 15
16 17
OHOH
OH
OHOH
OHOH
OH
OHOH
OH
OO
O
OOO
HOHO
HO
HOHO CH2OH
CH2OH
CH2
2
2
3
4 5
5
66
6n
OH
OH
OH
OH
OHO O
O
OO
HO
HO
HO HO
HO
HO
OH
OHO OHO
HO OHO OHO
HO OHO
HOHO
OH
OH
OH
OH
OHOH
OHO OHO
HO OHO OHO
HO OHO
O
OO
OO
HO
HOHO
HOHO
HOHO
OHCH2OH
CH2
OH
OH
OH
OHO
OO
OO
HOHO HO
HOHO
HOHO
2
CH2OH
CH2
OH
OH
OH
OHO
OO
OO
HO
HOHO
HOHO
CH2OH
CH2
OH
OH
OH
OHO
OO
OO
HO
HOHO HO
HOHO
CH2OH
CH2
OH
OH
OH
OHO
OO
OO
HO
HO
HO HO
HOHO
CH2OH
CH2
OH
OH
OH
OHO
OO
OO
HO
HOHO HO
HOHO
CH2
OH
OH
OH OH
OHO
OO
OO
HO
HOHO HO
HOHO
OH
OH
OHOH
OH
OH
O
OO
O
OHO
HO
HOHO
HO
OH
OH
OH OHOH
OH
O
OO
O
OHO
HO
HOHO
HO
OH
OH OH
OH
OH
OH
OO
O O
O
HOHO HO
HO
HO
OH
OH OH
OH
OH
OO
O O
O
HOHO HO
HO
HOHO OH
OH
OH OHOH
OH
O
OO
O
O
HOHO
HO
HO
HO
Figure 1 Continued
6 Evidence-Based Complementary and Alternative Medicine
18 19
20 21
2
n
OH
OH
H
OH
OH
OH
OH
OO
O
O
O
HO
HOHO
HO
HO
CH2OH
OH
OHO OHO
HO OHO OHO
HO OH
OH
O
OO
HO
HOHO
HO
CH2OH
OH
OHO OHO
HO OHO OHO
HO OH
OH
O
OO
HO
HOHO
OH
OH
OHOHO
HO
OH
OH
OH
OH
OH
OHO
O
O
O
O
O
O
HO
HO
HO
OH
OH
OH
OH O
Figure 1
D benzoyl E p-methoxybenzoyl F p-hydroxybenzoyl G coumaroyl
I feruloyl J caffeoyl K sinapoyl
L 345-trimethoxycinnamoyl M cinnamoyl
O
O
O
O O O
OO
O
OCH3
OCH3
OCH3
OCH3
OCH3
OCH3
OCH3
OH
OHOH
OHOHOH
Figure 2
Evidence-Based Complementary and Alternative Medicine 7
Table2Ph
enylprop
anoid-deriv
eddisaccharid
eeste
rs
Num
ber
Nam
eR 1
R 2R 3
R 4R 5
R 6R 7
R 8Source
Parts
Reference
35Sibiric
oseA
6H
HH
HK
HH
HPolyg
alatricornis
Polyg
alatenu
ifolia
Roots
Root
barks
[37ndash40
]
3631015840-O
-FeruloylsucroseSibiricose
A5
HH
HH
IH
HH
Polyg
alatenu
ifolia
Trillium
kamtsc
haticum
Roots
Und
ergrou
ndparts
[38ndash42]
37GlomeratoseA
HH
HH
LH
HH
Polyg
alatricornis
Roots
[37]
38LapathosideD
HH
HH
GG
HH
Polyg
onum
sachalinense
Stem
s[43]
39Helo
niosideA
HH
HH
II
HH
Trillium
kamtsc
haticum
Smila
xbracteata
Paris
polyphylla
varyunn
anensis
Und
ergrou
ndparts
Aeria
lparts
Roots
[4144
45]
40Helo
niosideB
AcH
HH
II
HH
Smila
xbracteata
Smila
xchina
Smila
xrip
aria
Heterosmila
xerythrantha
Aeria
lparts
Stem
sRo
otsa
ndrhizom
es
[4446
ndash48]
41Paris
polysid
eFH
HH
HG
IH
HPa
risPolyphylla
varyunn
anensis
Rhizom
es[4950]
42Hydropiperosid
eH
HH
HG
GH
GPolyg
onum
sachalinense
Polyg
onum
cuspidatum
Persica
riahydropiper
Stem
sLeaves
[435152]
43Tricorno
seB
DAc
HH
LH
HH
Polyg
alatricornis
Roots
[37]
44Tenu
ifolisideA
FH
HH
LH
HH
Polyg
alatenu
ifolia
Polygalahongkongensis
Polyg
alasib
irica
Roots
Who
leplants
Aeria
lparts
[3840
4253ndash
56]
45Tataris
ideA
AcH
HAc
GG
HAc
Fagopyrum
tataric
umRo
ots
[57]
46Tataris
ideE
HH
HAc
GG
HAc
Fagopyrum
tataric
umRo
ots
[57]
47Tataris
ideG
HH
HH
IG
HG
Fagopyrum
tataric
umRo
ots
[57]
48Sm
iglasid
eAAc
AcH
AcI
IH
ISm
ilaxrip
aria
Rootsa
ndrhizom
es[47]
49Sm
iglasid
eBAc
HH
AcI
IH
ISm
ilaxrip
aria
Rootsa
ndrhizom
es[47]
50Sm
iglasid
eEAc
HH
AcI
IH
GSm
ilaxchina
Stem
s[46]
51Sm
ilasid
eAAc
AcH
HI
IH
HSm
ilaxchina
Stem
s[46]
52Sm
ilasid
eBH
HH
AcI
IH
HSm
ilaxchina
Stem
s[46]
53Sm
ilasid
eCH
HH
HI
IH
GSm
ilaxchina
Stem
s[46]
54Sm
ilasid
eDH
HH
HI
IAc
GSm
ilaxchina
Stem
s[46]
8 Evidence-Based Complementary and Alternative Medicine
Table2Con
tinued
Num
ber
Nam
eR 1
R 2R 3
R 4R 5
R 6R 7
R 8Source
Parts
Reference
55Sm
ilasid
eEAc
HH
HI
IH
GSm
ilaxbracteata
Smila
xchina
Aeria
lparts
Stem
s[4446
]
56Sm
ilasid
eFAc
HH
AcG
IH
GSm
ilaxchina
Stem
s[46]
57Sm
ilasid
eGH
HH
HG
IH
GSm
ilaxbracteata
Smilacis
glabrae
Aeria
lparts
Rhizom
es[4458]
58Sm
ilasid
eHH
HH
AcG
IH
GSm
ilaxbracteata
Aeria
lparts
[44]
59Sm
ilasid
eIAc
HH
HG
IH
GSm
ilaxbracteata
Aeria
lparts
[44]
60Sm
ilasid
eJH
HH
HG
IH
ISm
ilaxbracteata
Smilacis
glabrae
Aeria
lparts
Rhizom
es[4458]
61Sm
ilasid
eKH
HH
AcI
IH
GSm
ilaxbracteata
Aeria
lparts
[44]
62Sm
ilasid
eLH
HH
HI
IH
ISm
ilaxbracteata
Smilacis
glabrae
Aeria
lparts
Rhizom
es[4458]
63Sm
ilasid
eMAc
HH
AcCis-feruloyl
IH
HSm
ilaxrip
aria
Rootsa
ndrhizom
es[59]
64Sm
ilasid
eNAc
HH
AcI
Cis-
feruloyl
HH
Smila
xrip
aria
Rootsa
ndrhizom
es[59]
65Sm
ilasid
ePH
HH
AcI
IH
ISm
ilaxrip
aria
Rootsa
ndrhizom
es[47]
66310158404101584061015840-O
-Tri-
feruloylsucrose
HH
HH
II
IH
Smila
xrip
aria
Rhizom
esand
roots
[60]
6761015840-O
-Cou
maroylsu
crose
HH
HH
HG
HH
Bidens
parviflora
Who
leplants
[61]
6811015840 -O-C
oumaroyl-61015840-O
-feruloylsucrose
HH
HH
HI
HG
Smila
xbracteata
Aeria
lparts
[44]
694-O-Benzoyl-31015840-345-
trim
etho
xycinn
amoylsu
crose
HD
HH
LH
HH
Polyg
alatricornis
Roots
[37]
706-O-Benzoyl-31015840-O
-345-
trim
etho
xycinn
amoylsu
crose
DH
HH
LH
HH
Polyg
alatricornis
Roots
[37]
716-O-Benzoyl-31015840-O
-sin
apoylsu
crose
DH
HH
KH
HH
Polyg
alatricornis
Roots
[37]
726-O-p-M
etho
xybenzoyl-31015840-O
-345-
trim
etho
xycinn
amoylsu
crose
EH
HH
LH
HH
Polyg
alatenu
ifolia
Roots
[56]
7326-Di-a
cetyl-3101584061015840-di-
feruloylsucrose
AcH
HAc
II
HH
Smila
xchina
Smila
xrip
aria
Heterosmila
xerythrantha
Stem
sRo
otsa
ndrhizom
esAe
rialp
arts
[46ndash
4859]
7426-Di-a
cetyl-31015840-O
-cis-feruloy-
61015840-tr
ans-feruloylsucrose
AcH
HAc
Cis-feruloy
IH
HSm
ilaxrip
aria
Rootsa
ndrhizom
es[59]
Evidence-Based Complementary and Alternative Medicine 9
Table2Con
tinued
Num
ber
Nam
eR 1
R 2R 3
R 4R 5
R 6R 7
R 8Source
Parts
Reference
7526-Di-a
cetyl-31015840-O
-tran
s-feruloy-
61015840-cis-feruloylsucrose
AcH
HAc
ICis-
feruloyl
HH
Smila
xrip
aria
Rootsa
ndrhizom
es[59]
76Re
galosid
eAAc
HH
HI
HH
HTrillium
kamtsc
haticum
Und
ergrou
ndparts
[41]
77Tricorno
seA
AcH
HH
LH
HH
Polyg
alatricornis
Roots
[37]
78Mum
eose
AH
HH
AcG
HH
HPrun
usmum
eFlow
erbu
ds[6263]
79Mum
eose
BAc
HAc
HG
HH
HPrun
usmum
eFlow
erbu
ds[6263]
80Mum
eose
CAc
HAc
AcG
HH
HPrun
usmum
eFlow
erbu
ds[6263]
81Mum
eose
DAc
AcAc
AcG
HH
AcPrun
usmum
eFlow
erbu
ds[6263]
82Mum
eose
EAc
AcAc
AcCis-
coum
aroyl
HH
AcPrun
usmum
eFlow
erbu
ds[6263]
83Mum
eose
FAc
AcAc
HG
HH
HPrun
usmum
eFlow
erbu
ds[63]
84Mum
eose
GAc
HAc
HG
HAc
HPrun
usmum
eFlow
erbu
ds[63]
85Mum
eose
HH
HAc
AcG
HAc
HPrun
usmum
eFlow
erbu
ds[63]
86Mum
eose
IAc
AcAc
HG
AcH
HPrun
usmum
eFlow
erbu
ds[63]
87Mum
eose
JAc
AcAc
AcG
HAc
AcPrun
usmum
eFlow
erbu
ds[63 ]
88Mum
eose
KH
HAc
AcG
HH
HPrun
usmum
eFlow
erbu
ds[64]
89Mum
eose
LAc
HAc
AcG
HAc
HPrun
usmum
eFlow
erbu
ds[64]
90Mum
eose
MAc
AcAc
HG
HAc
AcPrun
usmum
eFlow
erbu
ds[64]
91Mum
eose
NAc
AcAc
HG
AcAc
HPrun
usmum
eFlow
erbu
ds[64]
92Mum
eose
OAc
HAc
AcG
HAc
AcPrun
usmum
eFlow
erbu
ds[64]
9311015840 2346-O-Penta-acetyl-31015840-O
-tra
ns-cou
maroylsu
crose
AcAc
AcAc
GH
HAc
Musellalasio
carpa
Aeria
lparts
[65]
9411015840 2346-O-Penta-acetyl-31015840-O
-cis-cou
maroylsu
crose
AcAc
AcAc
Cis-
coum
aroyl
HH
AcMusellalasio
carpa
Aeria
lparts
[65]
9511015840 236-O-Tetra-acetyl-31015840-O
-cis-
feruloylsucrose
AcH
AcAc
Cis-feruloyl
HH
AcSparganium
stolonifer
umRh
izom
es[66]
9611015840 246-O-Tetra-acetyl-31015840-O
-tra
ns-fe
ruloylsucrose
AcAc
HAc
IH
HAc
Sparganium
stolonifer
umRh
izom
es[66]
9711015840 236-O-Tetra-acetyl-31015840-O
-tra
ns-fe
ruloylsucrose
AcH
AcAc
IH
HAc
Sparganium
stolonifer
umRh
izom
es[67]
98Sibirio
sideA
MH
HH
HH
HH
Scrophularianingpoensis
Roots
[68]
99SibricoseA
1K
HH
HH
HH
HCy
nanchu
mam
plexica
ule
Roots
[69]
100
6-O-C
affeoylsucrose
JH
HH
HH
HH
Scrophularianingpoensis
Roots
[68]
101
Acretosid
eI
HH
HH
HH
HScrophularianingpoensis
Roots
[68]
10 Evidence-Based Complementary and Alternative Medicine
Table2Con
tinued
Num
ber
Nam
eR 1
R 2R 3
R 4R 5
R 6R 7
R 8Source
Parts
Reference
102
Tenu
ifolisideB
FH
HH
KH
HH
Polyg
alatenu
ifolia
Roots
[4256]
103
Tenu
ifolisideC
KH
HH
LH
HH
Polyg
alatricornis
Polyg
alatenu
ifolia
Roots
[374256]
104
Heterosmilasid
eH
HI
HH
IH
HHeterosmila
xerythrantha
Aeria
lparts
[48]
105
Quiqu
esetinerviusideA
HI
HH
II
HH
Calamus
quiquesetin
ervius
Stem
s[70]
106
Quiqu
esetinerviusideB
AcI
HH
II
HH
Calamus
quiquesetin
ervius
Stem
s[70]
107
Quiqu
esetinerviusideC
HI
HAc
II
HH
Calamus
quiquesetin
ervius
Stem
s[70]
108
Quiqu
esetinerviusideD
AcG
HH
II
HH
Calamus
quiquesetin
ervius
Stem
s[70]
109
Quiqu
esetinerviusideE
HG
HAc
II
HH
Calamus
quiquesetin
ervius
Stem
s[70]
110
Vanicosid
eAI
HH
AcG
GH
G
Polyg
onum
sachalinensis
Polyg
onum
cuspidatum
Polyg
onum
hydropiper
Stem
sLeaves
Rhizom
es[51527172]
111
Vanicosid
eBI
HH
HG
GH
G
Polyg
onum
sachalinensis
Polyg
onum
cuspidatum
Persica
riahydropiper
Stem
sLeaves
Rhizom
es[4351527172]
112
Vanicosid
eDG
HH
HG
GH
GPersica
riahydropiper
Leaves
[51]
113
Vanicosid
eEI
AcH
AcG
GH
GPolyg
onum
hydropiper
Stem
sand
leaves
[72]
114
LapathosideA
IH
HH
GG
HI
Polyg
onum
sachalinensis
Polyg
onum
cuspidatum
Fagopyrum
dibotrys
Stem
sRh
izom
es[5173]
115
LapathosideC
IH
HH
GG
HH
Polyg
onum
sachalinensis
Polyg
onum
cuspidatum
Stem
s[4352]
116
DibosideA
GH
HH
GI
HG
Fagopyrum
tataric
umFagopyrum
dibotrys
Roots
Rhizom
es[57]
117
Hidropiperosid
eAI
HH
HH
GH
GPolyg
onum
hydropiper
Stem
sand
leaves
[72]
118
Hidropiperosid
eBI
HH
AcG
GH
IPolyg
onum
hydropiper
Stem
sand
leaves
[72]
119
Tataris
ideB
IH
HAc
GG
HAc
Fagopyrum
tataric
umRo
ots
[57]
Evidence-Based Complementary and Alternative Medicine 11
Table2Con
tinued
Num
ber
Nam
eR 1
R 2R 3
R 4R 5
R 6R 7
R 8Source
Parts
Reference
120
Tataris
ideC
IAc
HAc
GG
HAc
Fagopyrum
tataric
umRo
ots
[57]
121
Tataris
ideD
GH
HAc
GI
HH
Fagopyrum
tataric
umRo
ots
[57]
122
Tataris
ideF
GH
HH
II
HG
Fagopyrum
tataric
umRo
ots
[57]
123
310158406-O
-Di-sinapoylsu
crose
KH
HH
KH
HH
Polyg
alatricornis
Polygalahongkongensis
Polyg
alasib
irica
Polyg
alatenu
ifolia
Cynanchu
mam
plexica
ule
Roots
Root
barks
Who
leplants
Aeria
lparts
[37ndash394153ndash
566974]
124
661015840-O
-Di-c
oumaroylsu
crose
GH
HH
HG
HH
Bidens
parviflora
Who
leplants
[61]
125
11015840 3101584061015840-O
-Tri-
coum
aroyl-6
-feruloylsucrose
IH
HH
GG
HG
Fagopyrum
tataric
umRo
ots
[7576]
126
3101584061015840-O
-Di-c
oumaroyl-110158406-O
-di-
feruloylsucrose
IH
HH
GG
HI
Fagopyrum
tataric
umRo
ots
[7576]
127
31015840-O
-Cou
maroyl-11015840610158406-O
-tri-
feruloylsucrose
IH
HH
IG
HI
Fagopyrum
tataric
umRo
ots
[7576]
128
11015840 31015840610158406-O
-Tetra-fe
ruloylsucrose
IH
HH
II
HI
Fagopyrum
tataric
umRo
ots
[7576]
SeeS
chem
e2
12 Evidence-Based Complementary and Alternative Medicine
131130129
CH2OHOH
OH
OO
OH
C
C
HH
HHO
OO
O
HO
HOHO
HO
HOOH
OHOHOH
OHOH
HOO
O
O
O
HO
HO
OH
OHOHOH
OHOH
HOO
O
O
O
HO
Figure 3
12
3
4
5
6
1998400
2998400
3998400
4998400
5998400
6998400
HO
O
O
R1O
R2O
R8O
R7OOR3
OR4 OR5OR6
Scheme 2
antidepressant cytotoxic antineoplastic anti-inflammatoryantidiabetic plant growth-regulatory neuroprotective andcerebral protective activities Lignan-derived disaccharideesters phenylpropanoid-derived tetrasaccharide esters andpentasaccharide esterswith biological activities have not beenreported Aside from the isolated constituents oligosaccha-ride mixtures from Rehmannia glutinosa Panax ginseng andScrophularia ningpoensiswere also reported to display diversepharmacological activities such as antidiabetic immunopo-tentiating enhanced memory and antineoplastic activitiesThese active compounds and mixtures could serve as thevaluable candidates to be developed as possible drugs for thetreatment and prevention of diseases
31 Antioxidant Activity The adverse effects of oxidativestress proposed to play significant roles in the pathogenesis ofcardiovascular diseases atherosclerosis hypertension can-cer diabetes mellitus neurodegenerative diseases rheuma-toid arthritis ischemiareperfusion injury and ageing havebecome an inevitable and serious issue [95 96] Scientistshave thus made great efforts to explore antioxidants frommedicinal plants by using different kinds of assay methodswhich include DPPH radical scavenging assay hydroxylradical scavenging assay superoxide anion scavenging assayand ABTS radical scavenging method [96]
Lapathosides C and D hydropiperoside vanicoside Bhidropiperosides A and B lapathoside A and diboside Awere isolated from the Polygonum Persicaria and Fagopyrumgenera belonging to the Polygonaceae family The DPPH testrevealed that free radical-scavenging activity of the isolatedcompounds termed lapathoside C (115) hydropiperoside(42) vanicoside B (111) and lapathoside D (38) increasedin turn and lapathoside D exhibited strongest scavengingability with an IC
50of 0088 120583M [43] Hidropiperosides A
and B (117 118) were reported to show obvious antioxidantresponse to DPPH radicals with the SC
50values of 234
and 267 120583gmL respectively while vanicoside E moderatelyexhibited the same activity with a SC
50value of 490 120583gmL
[72] Lapathoside A (114) and diboside A (116) just showedlower antioxidant activities with the SC
50values of 19948 and
16552 120583M respectively [73]Smiglasides A and B smilaside P 26-di-acetyl-3101584061015840-
di-feruloylsucrose helonioside B smilasides GndashL and het-erosmilaside were isolated from the Heterosmilax and Smi-lax genera Compared with ascorbic acid (IC
5014352 120583M)
used as positive control smiglasides A and B and smi-laside P (48 49 65) (IC
5033958 33066 and 31449 120583M
resp) showed higher antioxidant activities than 26-di-acetyl-3101584061015840-di-feruloylsucrose (73) and helonioside B (40) (IC
50
63166 and 51827120583M resp) [47] Additionally Nhiem et alreported that helonioside B heterosmilaside (104) and 26-di-acetyl-3101584061015840-di-feruloylsucrose exhibited important DPPHradical scavenging activities with the SC
50values of 91 127
and 87 120583gmL respectively [48] Compared with smilasidesG-I (57ndash59) (ED
50685ndash794120583M) smilasides JndashL (60ndash62)
showed higher radical scavenging activities with an ED50
value of 267ndash327120583M [44]Five quiquesetinerviusides AndashE (105ndash109) isolated from
the Calamus genus showed weak DPPH scavenging activ-ities (IC
50604ndash1018120583M) but exhibited better hydroxyl
radical scavenging activities (IC50
36ndash84 120583M) Moreoverquiquesetinerviuside C showed superoxide anion scaveng-ing activity with an IC
50value of about 1843 120583M [70]
Liu et al investigated the antioxidant capacity of 310158406-O-di-sinapoylsucrose (DISS) (123) by using the acceleratedsenescence-prone short-lived mice (SAMP) in vivo Theanalyses indicated that the activities of antioxidant enzymesof SOD and glutathione peroxidase ascended obviously inSAMP mice when amended with DISS 50mgkg MoreoverDISS could downregulate and even restore the level ofmalondialdehyde in SAMP model group [97]
From the above studies it can be concluded that oligosac-charide esters with antioxidant activities have been identifiedin the Polygonaceae Liliaceae Smilacaceae and Arecaceaefamilies The results of the antioxidant assays show that theincreased number of phenolic hydroxyl groups and acetylgroups could produce higher antioxidant activity Fan etal indicated that the increased number of phenylpropanoidgroups was not beneficial to free radical scavenging activity[43] Zhang et al pointed out that oligosaccharide esters withferuloyl groups exhibited better antioxidant activities thanthose with coumaroyl groups [44]
Evidence-Based Complementary and Alternative Medicine 13
Table 3 Fatty acid-derived disaccharide esters
Number Name R1 R2 Source Parts Reference132 61015840-O-Linoleylsucrose H O Astragalus membranaceus Roots [77]133 61015840-O-Palmitoylsucrose H P Astragalus membranaceus Roots [77]134 6-O-Palmitoylsucrose P H Astragalus membranaceus Roots [77]
135 61015840-O-Linolenoylsucrose H N Astragalus membranaceusEquisetum hiemale
RootsAerial parts [77 78]
136 6-O-Linoleylsucrose O H Astragalus membranaceus Roots [77]137 6-O-Myristoylsucrose Q H Astragalus membranaceus Roots [77]
138 6-O-[(7Z10Z13Z)-Hexadeca-71013-trienoyl]sucrose H R Equisetum hiemale Aerial parts [78]
139 6-O-[(7Z10Z)-Hexadeca-710-dienoyl]sucrose H S Equisetum hiemale Aerial parts [78]
See Scheme 3
12
3
4
5
6
1998400
2998400
3998400
4998400
5998400
6998400
HO
O
O
R1O
R2O
R8O
R7OOR3
OR4 OR5OR6
O
O
O
18
18
1616
16
14
N linolenoyl
O linoleyl
P palmitoyl
Q myristoyl
O
O
O
R hexadeca-71013-trienoyl
S hexadeca-710-dienoyl
Scheme 3
32 Antidepressant Activity The oligosaccharides obtainedfrom the Morinda genus not only show specific antidepres-sant and antistress activities but also have no suppression orexcitatory effects on central nervous system as well Whatis more they can be taken orally with little toxicity [21]The inulin-type hexasaccharide (IHS) (9) from Morindaofficinalis obviously exhibited cytoprotective activity whichcontributed to the antidepressant effect not only by providingthe PC12 with protection against Cort-induced lesion withIHS 0625 and 125 120583Mbut also by reducing theCort-induced[Ca2+]
119894overloading with IHS 25 and 10 120583M IHS 5 and
10 120583Mupregulated the nerve growth factormRNAexpressionin Cort-induced PC12 cells [22] Polygalatenosides A (181)and B (182) were isolated from the Polygala genus Theysignificantly inhibited the isotope-labeled RTI-55 binding to
norepinephrine transporter protein with the IC50
values of300 and 604 120583M respectively [91]
DISS and tenuifoliside A were isolated from the PolygalaandCynanchum genera Liu et al investigated the antidepres-sant effect of YZ ethanol extract based on the tail suspensiontest (TST) and forced swimming test (FST) which arethe ease-of-use and widely-accepted models for estimatingantidepressant activities in mice The results indicated thatYZ-50 fraction at a dose of 200mgkgwas able to significantlydecrease the immobility time in TST Furthermore YZ-50possessed ability to inhibit corticosterone-induced injury ofhuman neuroblastoma SH-SY5Y cells What is more DISS(123) and tenuifoliside A (44) two major compounds of YZ-50 fraction showed effective protective response to the lesionin SY5Y cells [53] The antidepressant-like effect of DISS at
14 Evidence-Based Complementary and Alternative Medicine
H3CO
HO
HOHO
HO
HO
HO
HOHO
O O
OO O
OO
O
O
O
OO
O
O
OH
OH
OH
OH
OCH3
OCH3
CH2OH
CH2OH
CH2OAc
CH2OAc
H3CO
HOHO
HO
O
O
O
OO
O
O
OH
OH
OH
OCH3
CH2OH
CH2OH
H3CO
H3CO H3CO
HOHO
HO
O
O
O
OO
O
O
OH
OH
OH
OCH3
CH2OH
CH2OAc
CH3O
H
HOHO
HO
HO
HOO O
OO O
OO
OH
OCH3
CH2OHCH2OH
H3CO H3CO
H
CH2CH2 HO
HO
HO
HO
HOO O
OO O
OO
OH
OCH3
CH2OHCH2OAc
H3CO
H
CH2
140 141 142
143 144 145
Figure 4
Table 4 Phenylpropanoid-derived trisaccharide esters
Number Name R1 R2 R3 R4 R5 R6 R7 Source Parts Reference146 Tricornose C K H H H H L H Polygala tricornis Roots [37]147 Tricornose D K H H H H K H Polygala tricornis Roots [37]148 Tricornose E K H H H K L H Polygala tricornis Roots [37]149 Tricornose F K H H H I L H Polygala tricornis Roots [37]See Scheme 4
O
OOO
O
R2O
R4O
R3O
R6O
OH
OH
OH
OH
OR1
OR5CH2OR7
Scheme 4
the doses of 5 10 and 20mgkg was also tested in chronicallymild stressed rats DISS was able to exhibit antidepressantactivity by upregulating the expression of noradrenergic-regulated plasticity genes including cell adhesion moleculeL1 brain-derived neurotrophic factor laminin and cAMP
response element binding protein factor in hippocampus[98] DISS improved the reward reaction by increasingsucrose intake and obviously decreased the levels of serumcortisol adrenocorticotrophic hormone and corticotropin-releasing factor Further DISS played an enhanced role inthe expression of mineralocorticoid receptor together withglucocorticoid receptor mRNA [99]
33 Cytotoxic and Antineoplastic Activities Smilasides AndashFand P smiglasides A and B smilaside P and helonioside Awere isolated from the Smilax Trillium and Paris generaKuo et al obtained smilasides AndashF (51ndash56) and evaluatedtheir cytotoxicity against human tumor cell lines comprisinghuman oral epithelium carcinoma (KB) human cervicalcarcinoma (Hela) human colon tumor (DLD-1) humanbreast adenocarcinoma (MCF-7) human lung carcinoma (A-549) and humanmedulloblastoma (Med) cells byMTTassayExperimental data indicated that all but smilaside C showedcytotoxicity against three to six human tumor cell lines(ED50
= 51ndash130 120583gmL) and smilasides DndashF (ED50
= 27ndash50 120583gmL) displayed strong cytotoxic activities against DLD-1 cells [46]Wang et al reported the antitumor constituents of
Evidence-Based Complementary and Alternative Medicine 15
OH
OH
OH
OH
OH
OHOH
OHOH
OHOH
OH
OHOHOH
OH
OH
OH
OHOH
OH
OH
OHOH
H
H H
HO
O
O
O
O
O
O
O
OO
OO
O
OO
O
HO
HO
HO
OO
O
O
OO
OO
O
OO
O
OO
O
OO
O
O
O
OO
O
O
OO
O
OO
OOOO
HO
HO
HO
HO
HO
HO
HO
HO
HO
HO
HOHO
HO
HO
HO
HO
HO
150 151 152
153 180
AcO
AcO
AcOAcO
OAc
OAc
CH2OH
OHOH
OH OHOH
OHOH
OH
OHOH
CH3O
Figure 5
Table 5 Phenylpropanoid-derived tetrasaccharide esters
Number Name R1 R2 R3 Source Parts Reference154 Tricornose G K H K Polygala tricornis Roots [37]155 Tricornose H K K K Polygala tricornis Roots [37]156 Tricornose I K K L Polygala tricornis Roots [37]157 Tricornose J K I L Polygala tricornis Roots [37]158 Tricornose K K I K Polygala tricornis Roots [37]159 Tricornose L K G K Polygala tricornis Roots [37]See Scheme 5
Smilax riparia including smiglasides A (48) and B (49) 26-di-acetyl-3101584061015840-di-feruloylsucrose (73) helonioside B (40)and smilaside P (65) Only smiglasidesA andB and smilasideP exhibited cytotoxicity against human tumor cell lines withdifferent inhibitory concentrations comparing with cisplatinand paclitaxel as positive controls [47] Helonioside A (39)exhibited higher cytotoxicity with the increase of concentra-tion (01ndash100120583gmL) [45] Tatarisides AndashG (45 119ndash121 46122 47) and diboside A (116) from the Fagopyrum genusexerted cytotoxic activities against different human cell linesand the cytotoxicity of tatariside C was the most remarkablewith the IC
50values ranging from 644 to 749 120583gmL [57]
11015840236-O-Tetra-acetyl-31015840-O-cis-feruloylsucrose (95) fromthe Sparganium plants exhibited extremely weak cyto-toxicity against the growth of mice Lung Adenocarcinoma
795 cell lines with an IC50
value of 116 120583gmL [66] SnS-2oligosaccharides mixture including raffinose (3) stachyose(19) and verbascose (21) from the roots of Scrophularianingpoensis had antitumor activity against the growth ofLewis pulmonary carcinoma cells transplanted into mice[18]
Disaccharide esters and oligosaccharides mixture fromthe Liliaceae Polygonaceae Sparganiaceae and Scrpophular-iaceae families showed effective cytotoxic and antineoplasticactivities The study results indicated that feruloyl and acetylgroups play an important role in mediating cytotoxicitywhich seems to be related to the substitution position offeruloyl groups The feruloyl groups at C-6 or C-11015840 are vitalfor cytotoxicity In addition the increased number of acetylgroups could induce higher tumoricidal activity
16 Evidence-Based Complementary and Alternative Medicine
Table 6 Phenylpropanoid-derived pentasaccharide esters
Number Name R1 R2 R3 R4 R5 R6 Source Parts Reference160 Tenuifoliose A G D I Ac Ac Ac Polygala tenuifolia Roots [38 42]161 Tenuifoliose B G D I H Ac Ac Polygala tenuifolia Roots [42]162 Tenuifoliose C G D I H H H Polygala tenuifolia Roots [42]163 Tenuifoliose F G D U Ac Ac Ac Polygala tenuifolia Roots [42]164 Tenuifoliose G G D U Ac H Ac Polygala tenuifolia Roots [42]165 Tenuifoliose H G D G Ac Ac Ac Polygala tenuifolia Roots [38 42 79]166 Tenuifoliose I G D G Ac H Ac Polygala tenuifolia Roots [42 79]167 Tenuifoliose J G D G H Ac Ac Polygala tenuifolia Roots [42]168 Tenuifoliose K G D G H H Ac Polygala tenuifolia Roots [42]169 Tenuifoliose L G D T Ac Ac Ac Polygala tenuifolia Roots [42 79]170 Tenuifoliose M G D T Ac H Ac Polygala tenuifolia Roots [42]171 Tenuifoliose N I D I Ac Ac Ac Polygala tenuifolia Roots [42]172 Tenuifoliose O I D I H Ac Ac Polygala tenuifolia Roots [42]173 Tenuifoliose P I D I H H Ac Polygala tenuifolia Roots [42]174 Tenuifoliose Q G D T H Ac Ac Polygala tenuifolia Roots [79]175 Tenuifoliose S G D G H H H Polygala tenuifolia Roots [42]176 Tenuifoliose T G D I H H H Polygala tenuifolia Roots [42]177 Tenuifoliose V H D I Ac Ac Ac Polygala tenuifolia Roots [42]178 Tenuifoliose W I D U Ac H Ac Polygala tenuifolia Roots [42]179 Tenuifoliose X I D I H H H Polygala tenuifolia Roots [42]See Scheme 6
O
OO
O
O
O
O
OR1
OH
OH
OH
OHOH
OH
HOHO
HO
HO
OR2
R3O
CH2OH
Scheme 5
34 Anti-Inflammatory Activity Inflammation an importantbasic pathological process is a defense response of biopsywith vascular system to damage stimuli such as pathogensimpaired cells and tissues and physical and chemical factorsHowever if the process of inflammatory response cannot endnormally when cell debris and pathogens were cleared thebiological defence response will become causative factor andbring about many diseases such as diabetes cardiovasculardiseases metabolic syndrome and cancer [100 101]
Tenuifoliside A (44) from the Polygala genus exhibitedstrong anti-inflammatory effect not only by suppressing the
production of NO but also by reducing the production ofiNOS prostaglandin E2 cyclooxygenase-2 and proinflam-matory cytokines through the inhibition of the mitogen-activated protein kinases pathway and NF-120581B pathway [102]The anti-inflammatory activities of quiquesetinerviusides D(108) and E (109) from the Calamus genus were evaluated inRAW 2647 cells Both of them showed significant inhibitoryeffects against the production of LPS-stimulated NOwith theIC50values of 90ndash295120583M [70]Six disaccharide fatty acid esters (132ndash137) were iso-
lated from the Astragalus and Equisetum genera The anti-inflammatory effects of these isolated compounds have alsobeen documented The activation of NF-120581B could upregulatethe expression of proinflammatory cytokines inducible nitricoxide synthase (iNOS) and tumornecrosis factor alpha (TNF-120572) The NF-120581B inhibitory activities of compounds 132ndash137were tested in HepG2 cells stimulated with TNF-120572 All ofthese compounds could significantly restrainTNF-120572-inducedNF-120581B transcriptional activities with the IC
50values of 44ndash
247 120583M Li et al pointed out that olefinic bonds and thelength of the fatty acid moieties contributed to the NF-120581B inhibitory activity Furthermore the inhibition increasedsignificantly with the increase of the number of olefinic bondson the aliphatic moiety [77] These results may provide ascientific basis for the development of new anti-inflammatoryagents
35 Neuroprotective and Cerebral Protective Activities Aswe all know glutamate works as a major excitatory aminoacid neurotransmitter in the mammalian central nervous
Evidence-Based Complementary and Alternative Medicine 17
R6O
R2O
OR3
OR5
OR4
CH2OR1
OCH3
Rham
OO
O
OO O
O
O
O
OO
RhamO
O
OH
OH
OHOH
OH
OHOH
OHHO
HO
HO
T O-rhamnosyl-coumaroyl U O-rhamnosyl-feruloyl
Scheme 6
system and plays a crucial role in several physiological pro-cesses [103] However the accumulation of glutamate inducesdiverse acute and chronic neurodegenerative diseases suchas epilepsy ischemic stroke and Parkinsonrsquos disease aswell as Alzheimerrsquos disease [104] DISS (123) isolated fromthe Polygala genus exhibited neuroprotective effect againstglutamate-induced SH-SY5Y neuronal cell damage The invitro test demonstrated that DISS (06 6 and 60 120583molL)played a critical role in increasing cell viability controllinglactate dehydrogenase and attenuated apoptosis ranging from195 to 258 [105]
Tenuifoliside B (102) from the Polygala genus was ableto significantly shorten the coma time of KCN-inducedanoxia mice at the doses of 3 and 10mgkg and it playedan important role in ameliorating the scopolamine-inducedimpairment of performance in passive avoidance task inrats and enhancing the tremors induced by oxotremorine inmiceThese results together demonstrated that tenuifoliside Bpossessed cognitive improving and cerebral protective effects[56]
36 Antidiabetic Activity Diabetes mellitus a chronic debil-itating metabolic disease is characterized by high bloodglucose content and comprises three types termed type Itype II and gestational diabetes [106] Stachyose (19) extract(a part) from Rehmannia glutinosa obviously exhibited theactivity of downregulating fasting plasma glucose level andpartially keeping from hyperglycemia induced by adrenalineand glucose without obvious dose-dependent effect Otherthan that in vivo tests in rats induced by alloxan revealed
that stachyose extract at the dose of 200mgkg significantlydecreased blood-sugar level [15]
Diboside A lapathosides C and D vanicosides A andB and hydropiperoside were isolated from the FagopyrumPolygonum and Persicaria genera belonging to the Polygo-naceae family Diboside A (116) could potentially inhibit 120572-amylase activity with an IC
50of 269 120583M and thus retard the
starch digestion rate which is helpful for diabetic individualsin controlling blood sugar level [107] Lapathoside D (38)exerted stronger activity of 120572-glucosidase inhibition with anIC50
value of 0113mM than acarbose which was chosen asa positive drug for the treatment of type II diabetes [43]Vanicoside B (111) was reported to have higher 120573-glucosidaseinhibitory activity with an IC
50of 505 120583M than vanicoside A
(110) with an IC50of 599 120583M because of the acetyl moiety of
the latter possibly decreasing inhibitory activity of vanicosideA [71]
Fujimoto et al investigated the inhibitory effects ofmumeoses FndashO (83ndash92) from the Prunus genus on aldosereductase and discovered that caffeoyl groups are crucialfor the inhibitory effect on aldose reductase And thusmumeoses F G H J K L M and N (IC
50= 22ndash77120583M) with
a coumaroyl group and acetyl groups inhibited moderatelyaldose reductase from reducing glucose to sorbitol whichis associated with the chronic complications of diabetes [6364]
37 Elicitors and Regulators Oligosaccharides are quitepropitious for encoding biological information because ofdiverse monosaccharide units and complex molecular struc-tures and they are therefore first described as biological
18 Evidence-Based Complementary and Alternative Medicine
181 H
H
H
H
H
H
H
H
H H
H
H
H
H
H
H
H H
HH
Benzyl
Benzyl
Benzyl
182
183
184 Ac
Ac
Ac
Ac
Ac
Ac
Ac
Ac
Ac
Ac
185
186
187
188
189
R1 R2 R3
R1 R2 R3 R4
OCH3
R3OH2C OR2
OR1
OR1
O
O
O
O O
OOO
O
OO
O
OH
OH
OH OH
OH
O O
O
O
OH
HO
OH
OH OHOH
OH
OH
OHHO
HO
OH
OH
HO
CH2OH
CH2OH
CH2OH
CH2OH
C
R2O
R3O
CH2OR4
CH2CH2 CH2CH2CH2CH2CH3
CH3
CH3
191190 192
193
O
C C
O
OO
OO
OO
OO
O O
O
O
O
O
O
O
OH
OH
OHHO
HO
HOOH
OH
OH
OH
HO
OH
OH
OH
OH
HO
HO
C C
R998400O
R998400
Figure 6
signals in plants [108] Oligosaccharides from the cell wallfragments of plants and fungi are powerful signal moleculessuch as the elicitors of plant defence response and theregulators of plant growth and they are capable of exertingbiological activities at exceedingly low concentrations [109]Heptasaccharide (HS) (15) and octasaccharide (OS) (16) iso-lated from the Paris genus possessed plant growth-regulatory
activities [29 30]The two oligosaccharides significantly pro-moted the proliferation of Paris polyphylla var yunnanensisroots at the doses of 25ndash20mgL The octasaccharide hadthe most obvious effect on the growth of Panax japonicusvar major hairy roots at a dose of 30mgL while the otherhad the most positive effect on saponin accumulation ofPanax japonicus var major hairy roots at a dose of 10mgL
Evidence-Based Complementary and Alternative Medicine 19
[29] Similarly Zhou et al evaluated the stimulating effectsof HS and OS on the root growth and saponin productionof Panax ginseng hairy roots which were induced from theplant roots infected withAgrobacterium rhizogenes strain A4The results showed that there was a maximum effect on thehairy roots growth and saponin accumulation on day 10Compared with control group the root biomass dry weightwas increased by more than 17-fold while the total saponincontent of roots increased by more than 1-fold when thesetwo oligosaccharides were added to the hairy root at a dose of30mgL [30] The above data illustrate that HS and OS couldserve as the plant growth-regulators not only in their originalspecies but also in others
38 Immunopotentiating Activity Macrophages are impor-tant targets of investigations on cytophagy cellular immunityand molecular immunology Therefore they are deemedto play a vital role in host defense comprising phagocy-tosis proteolytic processing pathogenic agent apoptosiscytokines production and foreign antigens presentation[110] The water-extracted oligosaccharides from Panax gin-seng (WGOS) exhibited better immunopotentiating activ-ity by increasing phagocytic function of macrophages andpromoting NO TNF-120572 and reactive oxygen species pro-duction [110] In addition Wan et al have obtained malto-oligosaccharides (17 119899 = 3sim8) and three oligosaccharides (213 14) from the Panax ginseng roots The in vitro bioassaypointed out thatWGOS could serve as efficacious stimulatorsof B and T lymphocytes [28] These studies provided enlight-enment that the mixture of oligosaccharides from Chineseherbalmedicine exhibits significant effect on immune system
39 Others Acetylcholinesterase (AChE) inhibitors showgood therapeutic effects onmyasthenia gravis glaucoma andAlzheimerrsquos disease through reversible enzyme inhibitionso as to increase the accumulation of acetylcholine in thesynapse and then promote and prolong the function ofacetylcholine Vanicoside B (111) showed AChE inhibitoryactivity with an IC
50of 0062mM while hydropiperoside
(42) and lapathosides C (115) and D (38) just exhibited weakenzyme inhibitory activity [43]
Wang et al has explored low molecular mass carbohy-drate polymer from Panax ginseng roots and obtained 30ethanol elution (PGO)which included peptides and oligosac-charides (17 119899 = 0sim5) identified as maltose maltotriosemaltotetraose maltopentaose maltohexaose and maltohep-taose Pharmacological experiments revealed that PGO couldsignificantly enhance the memory in scopolamine-inducedmemory deficit rats [27]
Cistanoside F (129) and kankanose (150) were isolatedfrom the Cistanche Paulownia and Acanthus genera Phar-macological experiments showed that cistanoside F andkankanose significantly exhibited vasorelaxant effects on thenoradrenaline-induced contraction of thoracic aorta fromrats [80]
4 Conclusion
Traditional Chinese medicine from natural kingdom playsan indelible role in the treatment of human diseases andit has aroused the attention of those who have engagedin medicinal pharmaceutical chemistry Therefore scientistshave made great contributions day after day to investigate thevalid chemicals from traditional Chinese medicines In thepast decades about 193 oligosaccharides and their esters havebeen identified from traditional Chinese medicinal plantsOn the one hand only a few oligosaccharides and theirmixtures were investigated and just exhibited antidepres-sant antineoplastic antidiabetic plant growth-regulatoryimmunopotentiating and enhancedmemory activitiesMoreexploratory work is still needed to excavate biological andpharmacological activities of oligosaccharides On the otherhand oligosaccharide esters exhibited multi-advantageousactivities Bioassays have revealed that antioxidant cytotoxicantineoplastic and anti-inflammatory activities are the mostnotable bioactivities Of course to search for the naturalproducts with these activities is a hotpot in the contemporarydrug research Oligosaccharide esters provide a vast treasuretrove for medical researchers After considering the currentstudies it should be taken as future directions to makemore mechanism of action studies and clinical trials tofurther evaluate its potential as new drugs Moreover thestructure-activity relationships discussed in this review willprovide reference information for further exploring theirrelationships and continually discovering the new bioactiveoligosaccharide esters
Conflict of Interests
The authors declare that there is no conflict of interestsregarding the publication of this paper
References
[1] X D Yang L J Zhang B Liang L Z Xu and S L YangldquoOligosaccharide esters isolated from plants of PolygalaceaerdquoChinese Traditional and Herbal Drugs vol 33 no 10 pp 954ndash958 2002
[2] N Ogwuru and M Adamczeski ldquoBioactive natural productsderived from Polygonum species of plants their structures andmechanisms of actionrdquo Studies in Natural Products Chemistryvol 22 pp 607ndash642 2000
[3] S Kobayashi T Miyase and H Noguchi ldquoPolyphenolic glyco-sides and oligosaccharide multiesters from the roots of Polygaladalmaisianardquo Journal of Natural Products vol 65 no 3 pp 319ndash328 2002
[4] M Takasaki S Kuroki M Kozuka and T Konoshima ldquoNewphenylpropanoid esters of sucrose from Polygonum lapathi-foliumrdquo Journal of Natural Products vol 64 no 10 pp 1305ndash1308 2001
[5] M L Zimmermann and A T Sneden ldquoVanicosides A and Bprotein kinase C inhibitors from Polygonum pensylvanicumrdquoJournal of Natural Products vol 57 no 2 pp 236ndash242 1994
[6] M Takasaki T Konoshima S Kuroki H Tokuda and HNishino ldquoCancer chemopreventive activity of phenylpropanoid
20 Evidence-Based Complementary and Alternative Medicine
esters of sucrose vanicoside B and lapathoside A from Poly-gonum lapathifoliumrdquo Cancer Letters vol 173 no 2 pp 133ndash138 2001
[7] Q Fu T Liang Z Y Li et al ldquoSeparation of carbohydrates usinghydrophilic interaction liquid chromatographyrdquo CarbohydrateResearch vol 379 pp 13ndash17 2013
[8] M F Mrozek D Zhang and D Ben-Amotz ldquoOligosaccharideidentification and mixture quantification using Raman spec-troscopy and chemometric analysisrdquo Carbohydrate Researchvol 339 no 1 pp 141ndash145 2004
[9] G S Armstrong and B Bendiak ldquoHigh-resolution four-dimen-sional carbon-correlated 1H-1H ROESY experiments employ-ing isotags and the filter diagonalization method for effectiveassignment of glycosidic linkages in oligosaccharidesrdquo Journalof Magnetic Resonance vol 181 no 1 pp 79ndash88 2006
[10] G S Armstrong V A Mandelshtam A J Shaka and BBendiak ldquoRapid high-resolution four-dimensional NMR spec-troscopy using the filter diagonalization method and its advan-tages for detailed structural elucidation of oligosaccharidesrdquoJournal of Magnetic Resonance vol 173 no 1 pp 160ndash168 2005
[11] H-M Tseng S Gattolin J Pritchard H J Newbury and DA Barrett ldquoAnalysis of mono- di- and oligosaccharides by CEusing a two-stage derivatization method and LIF detectionrdquoElectrophoresis vol 30 no 8 pp 1399ndash1405 2009
[12] N Li X Li B L Hou and D L Meng ldquoNew disaccharosidefrom Camptosorus sibiricus Ruprrdquo Natural Product Researchvol 22 no 15 pp 1379ndash1383 2008
[13] Z Zhang D Wang Y Zhao H Gao Y-H Hu and J-FHu ldquoFructose-derived carbohydrates from Alisma orientalisrdquoNatural Product Research vol 23 no 11 pp 1013ndash1020 2009
[14] X Yang Y Zhao N He and K D Croft ldquoIsolation char-acterization and immunological effects of 120572-galacto-oligo-saccharides from a new source the herb Lycopus lucidus TurczrdquoJournal of Agricultural and Food Chemistry vol 58 no 14 pp8253ndash8258 2010
[15] R X Zhang Z P Jia L Y Kong et al ldquoStachyose extractfrom Rehmannia glutinosa Libosch to lower plasma glucose innormal and diabetic rats by oral administrationrdquo Pharmazievol 59 no 7 pp 552ndash556 2004
[16] R Zhang Y Zhao Y Sun X Lu and X Yang ldquoIsolationcharacterization and hepatoprotective effects of the raffinosefamily oligosaccharides from Rehmannia glutinosa liboschrdquoJournal of Agricultural and Food Chemistry vol 61 no 32 pp7786ndash7793 2013
[17] H Li F Song Z Zheng Z Liu and S Liu ldquoCharacterization ofsaccharides and phenolic acids in the Chinese herb Tanshen byESI-FT-ICR-MS and HPLCrdquo Journal of Mass Spectrometry vol43 no 11 pp 1545ndash1552 2008
[18] J E Deng J Zhang XM ChenW Ke and G Y Tian ldquoStudieson the physicochemical properties structure and antitumoractivity of an oligosaccharide homologue SnS-2 from the root ofScrophularia ningpoensis Hemslrdquo Chinese Journal of Chemistryvol 22 no 5 pp 492ndash497 2004
[19] S C Chou LM Chuang and S S Lee ldquoHypoglycemic constit-uents of gynura divaricata subsp formosanardquo Natural ProductCommunications vol 7 no 2 pp 221ndash222 2012
[20] F Feng L-L Wang X-P Lai Y-B Li Z-M Cao and Y-J Zhou ldquoStudy on oligosaccharides from Morinda officinalisrdquoJournal of Chinese Medicinal Materials vol 35 no 8 pp 1259ndash1262 2012
[21] Y F Li Z H Gong M Yang Y M Zhao and Z P Luo ldquoInhibi-tion of the oligosaccharides extracted fromMorinda officinalis
a Chinese traditional herbal medicine on the corticosteroneinduced apoptosis in PC12 cellsrdquo Life Sciences vol 72 no 8 pp933ndash942 2003
[22] Y-F Li Y-Q Liu M Yang et al ldquoThe cytoprotective effect ofinulin-type hexasaccharide extracted from Morinda officinalison PC12 cells against the lesion induced by corticosteronerdquo LifeSciences vol 75 no 13 pp 1531ndash1538 2004
[23] D N Olennikov L M Tankhaeva and A V Rokhin ldquoGlu-cofructans from Saussurea lappa rootsrdquo Chemistry of NaturalCompounds vol 47 no 3 pp 339ndash342 2011
[24] S K Hyun H A Jung B S Min J H Jung and J S ChoildquoIsolation of phenolics nucleosides saccharides and an alkaloidfrom the root of Aralia cordatardquo Natural Product Sciences vol16 no 1 pp 20ndash25 2010
[25] Z J Xu C W Lin and M F Liao ldquoStructure analysis of a newoligosaccharides BROS from Blumea ripariardquo Chinese Journalof Organic Chemistry vol 31 no 11 pp 1811ndash1819 2011
[26] Z J Xu C W Lin and Y Shi ldquoIsolation and structuredetermination of a new oligosaccharide from Blume ripariardquoJournal of Medicinal Plants Research vol 5 no 14 pp 2956ndash2962 2011
[27] Y Wang R Z Jiang G R Li et al ldquoStructural and enhancedmemory activity studies of extracts from Panax ginseng rootrdquoFood Chemistry vol 119 no 3 pp 969ndash973 2010
[28] DWan L Jiao H Yang and S Liu ldquoStructural characterizationand immunological activities of the water-soluble oligosaccha-rides isolated from thePanax ginseng rootsrdquoPlanta vol 235 no6 pp 1289ndash1297 2012
[29] L G Zhou C Z Yang J Q Li S L Wang and J Y WuldquoHeptasaccharide and octasaccharide isolated from Paris pol-yphylla var yunnanensis and their plant growth-regulatoryactivityrdquo Plant Science vol 165 no 3 pp 571ndash575 2003
[30] L G Zhou X D Cao R F Zhang Y L Peng S J Zhao andJ Y Wu ldquoStimulation of saponin production in Panax ginsenghairy roots by two oligosaccharides from Paris polyphylla varyunnanensisrdquo Biotechnology Letters vol 29 no 4 pp 631ndash6342007
[31] M Vanhaecke W van den Ende E Lescrinier and N Dyu-bankova ldquoIsolation and characterization of a pentasaccharidefrom Stellaria mediardquo Journal of Natural Products vol 71 no 11pp 1833ndash1836 2008
[32] J Feng and W Zhao ldquoComplete 1Hand 13C NMR assignmentsof four new oligosaccharides and two new glycosides fromPeriploca forrestiirdquoMagnetic Resonance in Chemistry vol 47 no8 pp 701ndash705 2009
[33] J Q Feng R J Zhang Y Zhou et al ldquoImmunosuppressive preg-nane glycosides from Periploca sepium and Periploca forrestiirdquoPhytochemistry vol 69 no 15 pp 2716ndash2723 2008
[34] X H Long R Xu Y H Zhang X H Tan andQ Y Sun ldquoA newoligosaccharide from Periploca calophyllardquo Zhongguo ZhongyaoZazhi vol 37 no 2 pp 226ndash229 2012
[35] L Wang Z-Q Yin Y Wang X-Q Zhang Y-L Li and W-CYe ldquoPerisesaccharides A-E new oligosaccharides from the rootbarks ofPeriploca sepiumrdquoPlantaMedica vol 76 no 9 pp 909ndash915 2010
[36] T Lei L Zhang H-Y Jiang Y Hu A-H Hong and Y-Z CenldquoA new pregnane glycoside and oligosaccharide from Parabar-ium huaitingiirdquo Journal of Asian Natural Products Research vol13 no 11 pp 1030ndash1035 2011
[37] J Li Y Jiang and P F Tu ldquoTricornoses A-L oligosaccharidemulti-esters from the roots of Polygala tricornisrdquo Journal ofNatural Products vol 68 no 5 pp 739ndash744 2005
Evidence-Based Complementary and Alternative Medicine 21
[38] H H Tu P Liu L Mu et al ldquoStudy on antidepressant com-ponents of sucrose ester from Polygala tenuifoliardquo ZhongguoZhongyao Zazhi vol 33 no 11 pp 1278ndash1280 2008
[39] G M She Y Y Ba Y Liu H Lv W Wang and R B ShildquoAbsorbable phenylpropenoyl sucroses from Polygala tenuifo-liardquoMolecules vol 16 no 7 pp 5507ndash5513 2011
[40] J Yong and P F Tu ldquoStudies on the chemical constituents inroot bark of Polygala tenuifolia (II)rdquo China Journal of ChineseMateria Medica vol 29 no 8 pp 751ndash753 2004
[41] M Ono C Takamura F Sugita et al ldquoTwo new steroidglycosides and a new sesquiterpenoid glycoside from theunderground parts of Trillium kamtschaticumrdquo Chemical andPharmaceutical Bulletin vol 55 no 4 pp 551ndash556 2007
[42] Y Ling Z Li M Chen Z Sun M Fan and C HuangldquoAnalysis and detection of the chemical constituents of RadixPolygalae and their metabolites in rats after oral administrationby ultra high-performance liquid chromatography coupledwith electrospray ionization quadrupole time-of-flight tandemmass spectrometryrdquo Journal of Pharmaceutical and BiomedicalAnalysis vol 85 pp 1ndash13 2013
[43] P Fan L Terrier A-E Hay A Marston and K HostettmannldquoAntioxidant and enzyme inhibition activities and chemicalprofiles ofPolygonum sachalinensis FSchmidt exMaxim (Polyg-onaceae)rdquo Fitoterapia vol 81 no 2 pp 124ndash131 2010
[44] L J Zhang C C Liao H C Huang Y C Shen L M Yangand Y H Kuo ldquoAntioxidant phenylpropanoid glycosides fromSmilax bracteatardquo Phytochemistry vol 69 no 6 pp 1398ndash14042008
[45] L L Yan W Y Gao Y J Zhang and Y Wang ldquoA new phenyl-propanoid glycosides from Paris polyphylla var yunnanensisrdquoFitoterapia vol 79 no 4 pp 306ndash307 2008
[46] Y H Kuo Y W Hsu C C Liaw J K Lee H C Huang andL M Y Kuo ldquoCytotoxic phenylpropanoid glycosides from thestems of Smilax chinardquo Journal of Natural Products vol 68 no10 pp 1475ndash1478 2005
[47] W-X Wang T-X Li H Ma J-F Zhang and A-Q JialdquoTumoral cytotoxic and antioxidative phenylpropanoid glyco-sides in Smilax riparia A DCrdquo Journal of Ethnopharmacologyvol 149 no 2 pp 527ndash532 2013
[48] N X Nhiem P vanKiem C vanMinh et al ldquoPhenylpropanoidglycosides fromHeterosmilax erythrantha and their antioxidantactivityrdquo Archives of Pharmacal Research vol 32 no 10 pp1373ndash1377 2009
[49] Y Wang W Y Gao T J Zhang and Y Q Guo ldquoA novelphenylpropanoid glycosides and a new derivation of phenolicglycoside from Paris Polyphylla var yunnanensisrdquo ChineseChemical Letters vol 18 no 5 pp 548ndash550 2007
[50] J-Y Zhang Y-Z Wang Y-L Zhao et al ldquoPhytochemicals andbioactivities of Paris speciesrdquo Journal of Asian Natural ProductsResearch vol 13 no 7 pp 670ndash681 2011
[51] N H N Hashim F Abas K Shaari and N H Lajis ldquoLC-DAD-ESIMSMS characterization of antioxidant and anti-cholinesterase constituents present in the active fraction fromPersicaria hydropiperrdquo LWT Food Science and Technology vol46 no 2 pp 468ndash476 2012
[52] PH FanA EHayAMarstonHX Lou andKHostettmannldquoChemical variability of the invasive neophytes Polygonumcuspidatum Sieb and Zucc and Polygonum sachalinensis FSchmidt ex Maximrdquo Biochemical Systematics and Ecology vol37 no 1 pp 24ndash34 2009
[53] P Liu Y Hu D H Guo et al ldquoPotential antidepressantproperties of Radix Polygalae (Yuan Zhi)rdquo Phytomedicine vol17 no 10 pp 794ndash799 2010
[54] J F Wu S B Chen S L Chen and P F Tu ldquoThe chemical con-stituents of Polygala hongkongensisHemslrdquoActa PharmaceuticaSinica vol 42 no 7 pp 757ndash761 2007
[55] Y Song Y Jiang D Bi X Tian L Liang and P Tu ldquoChemicalconstituents from n-butanol extract of aerial part of Polygalasibiricardquo Zhongguo Zhongyao Zazhi vol 37 no 4 pp 471ndash4742012
[56] Y Ikeya S Takeda M Tunakawa et al ldquoCognitive improvingand cerebral protective effects of acylated oligosaccharides inPolygala tenuifoliardquo Biological and Pharmaceutical Bulletin vol27 no 7 pp 1081ndash1085 2004
[57] C J Zheng C L Hu X Q Ma C Peng H Zhang and L PQin ldquoCytotoxic phenylpropanoid glycosides from Fagopyrumtataricum (L) Gaertnrdquo Food Chemistry vol 132 no 1 pp 433ndash438 2012
[58] X Li Y F Zhang L Yang et al ldquoChemical profiling ofconstituents of Smilacis glabrae using ultra-high pressure liquidchromatography coupled with LTQ orbitrap mass spectrome-tryrdquo Natural Product Communications vol 7 no 2 pp 181ndash1842012
[59] T-T Sun D-W Zhang Y Han F-Y Dong andWWang ldquoSmi-lasides M and N two new phenylpropanoid glycosides fromSmilax ripariardquo Journal of Asian Natural Products Research vol14 no 2 pp 165ndash170 2012
[60] J Li X Bi G Zheng Y Hitoshi T Ikeda and T NoharaldquoSteroidal glycosides and aromatic compounds from Smilaxripariardquo Chemical amp Pharmaceutical Bulletin vol 54 no 10 pp1451ndash1454 2006
[61] N Wang X Yao R Ishii and S Kitanaka ldquoBioactive sucroseesters from Bidens parviflorardquo Phytochemistry vol 62 no 5 pp741ndash746 2003
[62] S Nakamura K Fujimoto T Matsumoto et al ldquoAcylatedsucroses and acylated quinic acids analogs from the flower budsof Prunus mume and their inhibitory effect on melanogenesisrdquoPhytochemistry vol 92 pp 128ndash136 2013
[63] K Fujimoto SNakamura TMatsumoto et al ldquoMedicinal flow-ers XXXVIII Structures of acylated sucroses and inhibitoryeffects of constituents on aldose reducatase from the flower budsofPrunusmumerdquoChemical and Pharmaceutical Bulletin vol 61no 4 pp 445ndash451 2013
[64] S Nakamura K Fujimoto T Matsumoto et al ldquoStructuresof acylated sucroses and an acylated flavonol glycoside andinhibitory effects of constituents on aldose reductase from theflower buds of Prunus mumerdquo Journal of Natural Medicines vol67 no 4 pp 799ndash806 2013
[65] L-B Dong J He X-Y Li et al ldquoChemical constituents fromthe aerial parts of Musella lasiocarpardquo Natural Products andBioprospecting vol 1 no 1 pp 41ndash47 2011
[66] Y Xiong K Z Deng Y Q Guo W Y Gao and T J ZhangldquoNew chemical constituents from the rhizomes of Sparganiumstoloniferumrdquo Archives of Pharmacal Research vol 32 no 5 pp717ndash720 2009
[67] Y Xiong K-Z Deng Y-Q Guo W-Y Gao and T-J ZhangldquoTwo new sucrose esters from Sparganium stoloniferumrdquo Jour-nal of Asian Natural Products Research vol 10 no 5 pp 425ndash428 2008
[68] B Chen N L Wang J H Huang and X S Yao ldquoIridoidand phenylpropanoid glycosides from Scrophularia ningpoensis
22 Evidence-Based Complementary and Alternative Medicine
Hemslrdquo Asian Journal of Traditional Medicines vol 2 no 3 pp119ndash123 2007
[69] H Chen Y Z Zhou L Qiao et al ldquoTwo new compounds fromCynanchum amplexicaulerdquo Journal of Asian Natural ProductsResearch vol 10 no 3 pp 248ndash251 2008
[70] C-L Chang L-J Zhang R Y Chen et al ldquoAntioxidant andanti-inflammatory phenylpropanoid derivatives from Calamusquiquesetinerviusrdquo Journal of Natural Products vol 73 no 9 pp1482ndash1488 2010
[71] Y Kawai H Kumagai H Kurihara K Yamazaki R Sawanoand N Inoue ldquo120573-Glucosidase inhibitory activities of phenyl-propanoid glycosides vanicoside A and B from Polygonumsachalinense rhizomerdquo Fitoterapia vol 77 no 6 pp 456ndash4592006
[72] P V Kiem N X Nhiem N X Cuong et al ldquoNew phenyl-propanoid esters of sucrose from Polygonum hydropiper andtheir antioxidant activityrdquo Archives of Pharmacal Research vol31 no 11 pp 1477ndash1482 2008
[73] K J Wang Y J Zhang and C R Yang ldquoAntioxidant phenolicconstituents from Fagopyrum dibotrysrdquo Journal of Ethnophar-macology vol 99 no 2 pp 259ndash264 2005
[74] N Cho J Huh H Yang et al ldquoChemical constituentsof Polygala tenuifolia roots and their inhibitory activity onlipopolysaccharide-induced nitric oxide production in BV2microgliardquo Journal of Enzyme Inhibition and Medicinal Chem-istry vol 27 no 1 pp 1ndash4 2012
[75] Q Ren C S Wu and J L Zhang ldquoUse of on-line stop-flowheart-cutting two-dimensional high performance liquid chro-matography for simultaneous determination of 12 major con-stituents in tartary buckwheat (Fagopyrum tataricum Gaertn)rdquoJournal of Chromatography A vol 1304 pp 257ndash262 2013
[76] Q Ren C S Wu Y Ren and J L Zhang ldquoCharacterizationand identification of the chemical constituents from tartarybuckwheat (Fagopyrum tataricumGaertn) by high performanceliquid chromatographyphotodiode array detectorlinear iontrap FTICR hybrid mass spectrometryrdquo Food Chemistry vol136 no 3-4 pp 1377ndash1389 2013
[77] W Li Y N Sun X T Yan et al ldquoNF-120581B inhibitory activityof sucrose fatty acid esters and related constituents fromAstragalus membranaceusrdquo Journal of Agricultural and FoodChemistry vol 61 no 29 pp 7081ndash7088 2013
[78] J T Cheng J He Y Li et al ldquoThree new sucrose fatty acid estersfrom Equisetum hiemale LrdquoHelvetica Chimica Acta vol 95 no7 pp 1158ndash1163 2012
[79] Y Jiang and P-F Tu ldquoTenuifoliose Q a new oligosaccharideester from the root of Polygala tenuifoliaWilldrdquo Journal of AsianNatural Products Research vol 5 no 4 pp 279ndash283 2003
[80] M Yoshikawa H Matsuda T Morikawa H H Xie S Naka-mura and O Muraoka ldquoPhenylethanoid oligoglycosides andacylated oligosugars with vasorelaxant activity from Cistanchetubulosardquo Bioorganic ampMedicinal Chemistry vol 14 no 22 pp7468ndash7475 2006
[81] P-F Tu H-M Shi Z-H Song Y Jiang and Y-Y ZhaoldquoChemical constituents of Cistanche sinensisrdquo Journal of AsianNatural Products Research vol 9 no 1 pp 79ndash84 2007
[82] C-L Si Y-Y Lu P-P Qin R-C Sun and Y-H Ni ldquoPhenolicextractives with chemotaxonomic significance from the bark ofPaulownia tomentosa var tomentosardquo BioResources vol 6 no4 pp 5086ndash5098 2011
[83] J Wu S Zhang Q Xiao et al ldquoPhenylethanoid and aliphaticalcohol glycosides from Acanthus ilicifoliusrdquo Phytochemistryvol 63 no 4 pp 491ndash495 2003
[84] Y Jiang and P-F Tu ldquoAnalysis of chemical constituents inCistanche speciesrdquo Journal of Chromatography A vol 1216 no11 pp 1970ndash1979 2009
[85] H Otsuka H Kuwabara and H Hoshiyama ldquoIdentification ofsucrose diesters of aryldihydronaphthalene-type lignans fromTrigonotis peduncularisand the nature of their fluorescencerdquoJournal of Natural Products vol 71 no 7 pp 1178ndash1181 2008
[86] M-R Suo J-S Yang and Q-H Liu ldquoLignan oligosaccharideesters from Eritrichium rupestrerdquo Journal of Natural Productsvol 69 no 4 pp 682ndash684 2006
[87] P-F Tu Z-H Song H-M Shi Y Jiang and Y-Y ZhaoldquoArylethyl (=phenylethanoid) glycosides and oligosaccharidefrom the stem of Cistanche tubulosardquo Helvetica Chimica Actavol 89 no 5 pp 927ndash935 2006
[88] M-H Shyr T-H Tsai and L-C Lin ldquoRossicasins A Band rosicaside F three new phenylpropanoid glycosides fromBoschniakia rossicardquoChemical and Pharmaceutical Bulletin vol54 no 2 pp 252ndash254 2006
[89] R FangNCVeitchGCKiteM J RHowes EA Porter andM S J Simmonds ldquoGlycosylated constituents of Iris fulvaandIris brevicaulisrdquoChemical amp Pharmaceutical Bulletin vol 59 no1 pp 124ndash128 2011
[90] J Fu L Zuo J Yang R Chen and D Zhang ldquoOligosaccharidepolyester and triterpenoid saponins from the roots of Polygalajaponicardquo Phytochemistry vol 69 no 7 pp 1617ndash1624 2008
[91] M-C Cheng C-Y Li H-C Ko F-N Ko Y-L Lin andT-S Wu ldquoAntidepressant principles of the roots of polygalatenuifoliardquo Journal of Natural Products vol 69 no 9 pp 1305ndash1309 2006
[92] H T Chang and P F Tu ldquoNew oligosaccharide esters andxanthone C-glucosides from Polygala telephioidesrdquo HelveticaChimica Acta vol 90 no 5 pp 944ndash950 2007
[93] J Li L Feng J Dai R Wang and T Nohara ldquoChemical con-stituents from Polygala telephioidesrdquo China Journal of ChineseMateria Medica vol 34 no 4 pp 402ndash405 2009
[94] W-P Yin T-Z Zhao and H-Y Zhang ldquoA novel oligosaccha-ride ester from Syringa pubescensrdquo Journal of Asian NaturalProducts Research vol 10 no 1 pp 95ndash100 2008
[95] M Valko D Leibfritz J Moncol M T D Cronin M Mazurand J Telser ldquoFree radicals and antioxidants in normal physio-logical functions and human diseaserdquoThe International Journalof Biochemistry amp Cell Biology vol 39 no 1 pp 44ndash84 2007
[96] D Krishnaiah R Sarbatly and R Nithyanandam ldquoA review ofthe antioxidant potential of medicinal plant speciesrdquo Food andBioproducts Processing vol 89 no 3 pp 217ndash233 2011
[97] P Liu Y Hu D-H Guo et al ldquoAntioxidant activity ofoligosaccharide ester extracted from Polygala tenuifolia roots insenescence-accelerated micerdquo Pharmaceutical Biology vol 48no 7 pp 828ndash833 2010
[98] Y Hu H-B Liao G Dai-Hong P Liu Y-Y Wang and KRahman ldquoAntidepressant-like effects of 361015840-disinapoyl sucroseon hippocampal neuronal plasticity and neurotrophic signalpathway in chronically mild stressed ratsrdquo NeurochemistryInternational vol 56 no 3 pp 461ndash465 2010
[99] Y Hu H B O Liao P Liu D-H Guo and K RahmanldquoA bioactive compound from Polygala tenuifolia regulatesefficiency of chronic stress on hypothalamic-pituitary-adrenalaxisrdquo Pharmazie vol 64 no 9 pp 605ndash608 2009
[100] A Jungbauer and SMedjakovic ldquoAnti-inflammatory propertiesof culinary herbs and spices that ameliorate the effects ofmetabolic syndromerdquoMaturitas vol 71 no 3 pp 227ndash239 2012
Evidence-Based Complementary and Alternative Medicine 23
[101] Q Xu Y Wang S Guo Z Shen and L Yang ldquoAnti-inflammatory and analgesic activity of aqueous extract of Flospopulirdquo Journal of Ethnopharmacology vol 152 no 3 pp 540ndash545 2014
[102] K S Kim D S Lee G S Bae et al ldquoThe inhibition of JNKMAPK and NF-120581B signaling by tenuifoliside A isolated fromPolygala tenuifolia in lipopolysaccharide-induced macrophagesis associated with its anti-inflammatory effectrdquo European Jour-nal of Pharmacology vol 721 no 1ndash3 pp 267ndash276 2013
[103] J-G Lee J-M Yon C Lin A Y Jung K Y Jung and S-YNamldquoCombined treatment with capsaicin and resveratrol enhancesneuroprotection against glutamate-induced toxicity in mousecerebral cortical neuronsrdquo Food and Chemical Toxicology vol50 no 11 pp 3877ndash3885 2012
[104] M L Jin S Y Park Y H Kim J-I Oh S J Lee andG Park ldquoThe neuroprotective effects of cordycepin inhibitglutamate-induced oxidative andER stress-associated apoptosisin hippocampal HT22 cellsrdquo NeuroToxicology vol 41 pp 102ndash111 2014
[105] P Liu Y Hu J Li et al ldquoProtection of SH-SY5Y neuronal cellsfrom glutamate-induced apoptosis by 36rsquo-disinapoyl sucrosea bioactive compound isolated from radix polygalardquo Journal ofBiomedicine and Biotechnology vol 2012 Article ID 728342 5pages 2012
[106] P-B Li W-L Lin Y-G Wang W Peng X-Y Cai and W-WSu ldquoAntidiabetic activities of oligosaccharides of Ophiopogonisjaponicus in experimental type 2 diabetic ratsrdquo InternationalJournal of Biological Macromolecules vol 51 no 5 pp 749ndash7552012
[107] T Liu Y M Yip L Song et al ldquoInhibiting enzymatic starchdigestion by the phenolic compound diboside A a mechanisticand in silico studyrdquo Food Research International vol 54 no 1pp 595ndash600 2013
[108] F Cote andMGHahn ldquoOligosaccharins structures and signaltransductionrdquo Plant Molecular Biology vol 26 no 5 pp 1379ndash1411 1994
[109] RACreelman and J EMullet ldquoOligosaccharins brassinolidesand jasmonates nontraditional regulators of plant growthdevelopment and gene expressionrdquo Plant Cell vol 9 no 7 pp1211ndash1223 1997
[110] L Jiao D Wan X Zhang B Li H Zhao and S LiuldquoCharacterization and immunostimulating effects on murineperitoneal macrophages of oligosaccharide isolated from Panaxginseng CAMeyerrdquo Journal of Ethnopharmacology vol 144 no3 pp 490ndash496 2012
Submit your manuscripts athttpwwwhindawicom
Stem CellsInternational
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
MEDIATORSINFLAMMATION
of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Behavioural Neurology
EndocrinologyInternational Journal of
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Disease Markers
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
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OncologyJournal of
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Oxidative Medicine and Cellular Longevity
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
PPAR Research
The Scientific World JournalHindawi Publishing Corporation httpwwwhindawicom Volume 2014
Immunology ResearchHindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Journal of
ObesityJournal of
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Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Computational and Mathematical Methods in Medicine
OphthalmologyJournal of
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Diabetes ResearchJournal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Research and TreatmentAIDS
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Gastroenterology Research and Practice
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Parkinsonrsquos Disease
Evidence-Based Complementary and Alternative Medicine
Volume 2014Hindawi Publishing Corporationhttpwwwhindawicom
Evidence-Based Complementary and Alternative Medicine 5
1 2 3 4
5 6 7 8
9 10 11 12
13 14 15
16 17
OHOH
OH
OHOH
OHOH
OH
OHOH
OH
OO
O
OOO
HOHO
HO
HOHO CH2OH
CH2OH
CH2
2
2
3
4 5
5
66
6n
OH
OH
OH
OH
OHO O
O
OO
HO
HO
HO HO
HO
HO
OH
OHO OHO
HO OHO OHO
HO OHO
HOHO
OH
OH
OH
OH
OHOH
OHO OHO
HO OHO OHO
HO OHO
O
OO
OO
HO
HOHO
HOHO
HOHO
OHCH2OH
CH2
OH
OH
OH
OHO
OO
OO
HOHO HO
HOHO
HOHO
2
CH2OH
CH2
OH
OH
OH
OHO
OO
OO
HO
HOHO
HOHO
CH2OH
CH2
OH
OH
OH
OHO
OO
OO
HO
HOHO HO
HOHO
CH2OH
CH2
OH
OH
OH
OHO
OO
OO
HO
HO
HO HO
HOHO
CH2OH
CH2
OH
OH
OH
OHO
OO
OO
HO
HOHO HO
HOHO
CH2
OH
OH
OH OH
OHO
OO
OO
HO
HOHO HO
HOHO
OH
OH
OHOH
OH
OH
O
OO
O
OHO
HO
HOHO
HO
OH
OH
OH OHOH
OH
O
OO
O
OHO
HO
HOHO
HO
OH
OH OH
OH
OH
OH
OO
O O
O
HOHO HO
HO
HO
OH
OH OH
OH
OH
OO
O O
O
HOHO HO
HO
HOHO OH
OH
OH OHOH
OH
O
OO
O
O
HOHO
HO
HO
HO
Figure 1 Continued
6 Evidence-Based Complementary and Alternative Medicine
18 19
20 21
2
n
OH
OH
H
OH
OH
OH
OH
OO
O
O
O
HO
HOHO
HO
HO
CH2OH
OH
OHO OHO
HO OHO OHO
HO OH
OH
O
OO
HO
HOHO
HO
CH2OH
OH
OHO OHO
HO OHO OHO
HO OH
OH
O
OO
HO
HOHO
OH
OH
OHOHO
HO
OH
OH
OH
OH
OH
OHO
O
O
O
O
O
O
HO
HO
HO
OH
OH
OH
OH O
Figure 1
D benzoyl E p-methoxybenzoyl F p-hydroxybenzoyl G coumaroyl
I feruloyl J caffeoyl K sinapoyl
L 345-trimethoxycinnamoyl M cinnamoyl
O
O
O
O O O
OO
O
OCH3
OCH3
OCH3
OCH3
OCH3
OCH3
OCH3
OH
OHOH
OHOHOH
Figure 2
Evidence-Based Complementary and Alternative Medicine 7
Table2Ph
enylprop
anoid-deriv
eddisaccharid
eeste
rs
Num
ber
Nam
eR 1
R 2R 3
R 4R 5
R 6R 7
R 8Source
Parts
Reference
35Sibiric
oseA
6H
HH
HK
HH
HPolyg
alatricornis
Polyg
alatenu
ifolia
Roots
Root
barks
[37ndash40
]
3631015840-O
-FeruloylsucroseSibiricose
A5
HH
HH
IH
HH
Polyg
alatenu
ifolia
Trillium
kamtsc
haticum
Roots
Und
ergrou
ndparts
[38ndash42]
37GlomeratoseA
HH
HH
LH
HH
Polyg
alatricornis
Roots
[37]
38LapathosideD
HH
HH
GG
HH
Polyg
onum
sachalinense
Stem
s[43]
39Helo
niosideA
HH
HH
II
HH
Trillium
kamtsc
haticum
Smila
xbracteata
Paris
polyphylla
varyunn
anensis
Und
ergrou
ndparts
Aeria
lparts
Roots
[4144
45]
40Helo
niosideB
AcH
HH
II
HH
Smila
xbracteata
Smila
xchina
Smila
xrip
aria
Heterosmila
xerythrantha
Aeria
lparts
Stem
sRo
otsa
ndrhizom
es
[4446
ndash48]
41Paris
polysid
eFH
HH
HG
IH
HPa
risPolyphylla
varyunn
anensis
Rhizom
es[4950]
42Hydropiperosid
eH
HH
HG
GH
GPolyg
onum
sachalinense
Polyg
onum
cuspidatum
Persica
riahydropiper
Stem
sLeaves
[435152]
43Tricorno
seB
DAc
HH
LH
HH
Polyg
alatricornis
Roots
[37]
44Tenu
ifolisideA
FH
HH
LH
HH
Polyg
alatenu
ifolia
Polygalahongkongensis
Polyg
alasib
irica
Roots
Who
leplants
Aeria
lparts
[3840
4253ndash
56]
45Tataris
ideA
AcH
HAc
GG
HAc
Fagopyrum
tataric
umRo
ots
[57]
46Tataris
ideE
HH
HAc
GG
HAc
Fagopyrum
tataric
umRo
ots
[57]
47Tataris
ideG
HH
HH
IG
HG
Fagopyrum
tataric
umRo
ots
[57]
48Sm
iglasid
eAAc
AcH
AcI
IH
ISm
ilaxrip
aria
Rootsa
ndrhizom
es[47]
49Sm
iglasid
eBAc
HH
AcI
IH
ISm
ilaxrip
aria
Rootsa
ndrhizom
es[47]
50Sm
iglasid
eEAc
HH
AcI
IH
GSm
ilaxchina
Stem
s[46]
51Sm
ilasid
eAAc
AcH
HI
IH
HSm
ilaxchina
Stem
s[46]
52Sm
ilasid
eBH
HH
AcI
IH
HSm
ilaxchina
Stem
s[46]
53Sm
ilasid
eCH
HH
HI
IH
GSm
ilaxchina
Stem
s[46]
54Sm
ilasid
eDH
HH
HI
IAc
GSm
ilaxchina
Stem
s[46]
8 Evidence-Based Complementary and Alternative Medicine
Table2Con
tinued
Num
ber
Nam
eR 1
R 2R 3
R 4R 5
R 6R 7
R 8Source
Parts
Reference
55Sm
ilasid
eEAc
HH
HI
IH
GSm
ilaxbracteata
Smila
xchina
Aeria
lparts
Stem
s[4446
]
56Sm
ilasid
eFAc
HH
AcG
IH
GSm
ilaxchina
Stem
s[46]
57Sm
ilasid
eGH
HH
HG
IH
GSm
ilaxbracteata
Smilacis
glabrae
Aeria
lparts
Rhizom
es[4458]
58Sm
ilasid
eHH
HH
AcG
IH
GSm
ilaxbracteata
Aeria
lparts
[44]
59Sm
ilasid
eIAc
HH
HG
IH
GSm
ilaxbracteata
Aeria
lparts
[44]
60Sm
ilasid
eJH
HH
HG
IH
ISm
ilaxbracteata
Smilacis
glabrae
Aeria
lparts
Rhizom
es[4458]
61Sm
ilasid
eKH
HH
AcI
IH
GSm
ilaxbracteata
Aeria
lparts
[44]
62Sm
ilasid
eLH
HH
HI
IH
ISm
ilaxbracteata
Smilacis
glabrae
Aeria
lparts
Rhizom
es[4458]
63Sm
ilasid
eMAc
HH
AcCis-feruloyl
IH
HSm
ilaxrip
aria
Rootsa
ndrhizom
es[59]
64Sm
ilasid
eNAc
HH
AcI
Cis-
feruloyl
HH
Smila
xrip
aria
Rootsa
ndrhizom
es[59]
65Sm
ilasid
ePH
HH
AcI
IH
ISm
ilaxrip
aria
Rootsa
ndrhizom
es[47]
66310158404101584061015840-O
-Tri-
feruloylsucrose
HH
HH
II
IH
Smila
xrip
aria
Rhizom
esand
roots
[60]
6761015840-O
-Cou
maroylsu
crose
HH
HH
HG
HH
Bidens
parviflora
Who
leplants
[61]
6811015840 -O-C
oumaroyl-61015840-O
-feruloylsucrose
HH
HH
HI
HG
Smila
xbracteata
Aeria
lparts
[44]
694-O-Benzoyl-31015840-345-
trim
etho
xycinn
amoylsu
crose
HD
HH
LH
HH
Polyg
alatricornis
Roots
[37]
706-O-Benzoyl-31015840-O
-345-
trim
etho
xycinn
amoylsu
crose
DH
HH
LH
HH
Polyg
alatricornis
Roots
[37]
716-O-Benzoyl-31015840-O
-sin
apoylsu
crose
DH
HH
KH
HH
Polyg
alatricornis
Roots
[37]
726-O-p-M
etho
xybenzoyl-31015840-O
-345-
trim
etho
xycinn
amoylsu
crose
EH
HH
LH
HH
Polyg
alatenu
ifolia
Roots
[56]
7326-Di-a
cetyl-3101584061015840-di-
feruloylsucrose
AcH
HAc
II
HH
Smila
xchina
Smila
xrip
aria
Heterosmila
xerythrantha
Stem
sRo
otsa
ndrhizom
esAe
rialp
arts
[46ndash
4859]
7426-Di-a
cetyl-31015840-O
-cis-feruloy-
61015840-tr
ans-feruloylsucrose
AcH
HAc
Cis-feruloy
IH
HSm
ilaxrip
aria
Rootsa
ndrhizom
es[59]
Evidence-Based Complementary and Alternative Medicine 9
Table2Con
tinued
Num
ber
Nam
eR 1
R 2R 3
R 4R 5
R 6R 7
R 8Source
Parts
Reference
7526-Di-a
cetyl-31015840-O
-tran
s-feruloy-
61015840-cis-feruloylsucrose
AcH
HAc
ICis-
feruloyl
HH
Smila
xrip
aria
Rootsa
ndrhizom
es[59]
76Re
galosid
eAAc
HH
HI
HH
HTrillium
kamtsc
haticum
Und
ergrou
ndparts
[41]
77Tricorno
seA
AcH
HH
LH
HH
Polyg
alatricornis
Roots
[37]
78Mum
eose
AH
HH
AcG
HH
HPrun
usmum
eFlow
erbu
ds[6263]
79Mum
eose
BAc
HAc
HG
HH
HPrun
usmum
eFlow
erbu
ds[6263]
80Mum
eose
CAc
HAc
AcG
HH
HPrun
usmum
eFlow
erbu
ds[6263]
81Mum
eose
DAc
AcAc
AcG
HH
AcPrun
usmum
eFlow
erbu
ds[6263]
82Mum
eose
EAc
AcAc
AcCis-
coum
aroyl
HH
AcPrun
usmum
eFlow
erbu
ds[6263]
83Mum
eose
FAc
AcAc
HG
HH
HPrun
usmum
eFlow
erbu
ds[63]
84Mum
eose
GAc
HAc
HG
HAc
HPrun
usmum
eFlow
erbu
ds[63]
85Mum
eose
HH
HAc
AcG
HAc
HPrun
usmum
eFlow
erbu
ds[63]
86Mum
eose
IAc
AcAc
HG
AcH
HPrun
usmum
eFlow
erbu
ds[63]
87Mum
eose
JAc
AcAc
AcG
HAc
AcPrun
usmum
eFlow
erbu
ds[63 ]
88Mum
eose
KH
HAc
AcG
HH
HPrun
usmum
eFlow
erbu
ds[64]
89Mum
eose
LAc
HAc
AcG
HAc
HPrun
usmum
eFlow
erbu
ds[64]
90Mum
eose
MAc
AcAc
HG
HAc
AcPrun
usmum
eFlow
erbu
ds[64]
91Mum
eose
NAc
AcAc
HG
AcAc
HPrun
usmum
eFlow
erbu
ds[64]
92Mum
eose
OAc
HAc
AcG
HAc
AcPrun
usmum
eFlow
erbu
ds[64]
9311015840 2346-O-Penta-acetyl-31015840-O
-tra
ns-cou
maroylsu
crose
AcAc
AcAc
GH
HAc
Musellalasio
carpa
Aeria
lparts
[65]
9411015840 2346-O-Penta-acetyl-31015840-O
-cis-cou
maroylsu
crose
AcAc
AcAc
Cis-
coum
aroyl
HH
AcMusellalasio
carpa
Aeria
lparts
[65]
9511015840 236-O-Tetra-acetyl-31015840-O
-cis-
feruloylsucrose
AcH
AcAc
Cis-feruloyl
HH
AcSparganium
stolonifer
umRh
izom
es[66]
9611015840 246-O-Tetra-acetyl-31015840-O
-tra
ns-fe
ruloylsucrose
AcAc
HAc
IH
HAc
Sparganium
stolonifer
umRh
izom
es[66]
9711015840 236-O-Tetra-acetyl-31015840-O
-tra
ns-fe
ruloylsucrose
AcH
AcAc
IH
HAc
Sparganium
stolonifer
umRh
izom
es[67]
98Sibirio
sideA
MH
HH
HH
HH
Scrophularianingpoensis
Roots
[68]
99SibricoseA
1K
HH
HH
HH
HCy
nanchu
mam
plexica
ule
Roots
[69]
100
6-O-C
affeoylsucrose
JH
HH
HH
HH
Scrophularianingpoensis
Roots
[68]
101
Acretosid
eI
HH
HH
HH
HScrophularianingpoensis
Roots
[68]
10 Evidence-Based Complementary and Alternative Medicine
Table2Con
tinued
Num
ber
Nam
eR 1
R 2R 3
R 4R 5
R 6R 7
R 8Source
Parts
Reference
102
Tenu
ifolisideB
FH
HH
KH
HH
Polyg
alatenu
ifolia
Roots
[4256]
103
Tenu
ifolisideC
KH
HH
LH
HH
Polyg
alatricornis
Polyg
alatenu
ifolia
Roots
[374256]
104
Heterosmilasid
eH
HI
HH
IH
HHeterosmila
xerythrantha
Aeria
lparts
[48]
105
Quiqu
esetinerviusideA
HI
HH
II
HH
Calamus
quiquesetin
ervius
Stem
s[70]
106
Quiqu
esetinerviusideB
AcI
HH
II
HH
Calamus
quiquesetin
ervius
Stem
s[70]
107
Quiqu
esetinerviusideC
HI
HAc
II
HH
Calamus
quiquesetin
ervius
Stem
s[70]
108
Quiqu
esetinerviusideD
AcG
HH
II
HH
Calamus
quiquesetin
ervius
Stem
s[70]
109
Quiqu
esetinerviusideE
HG
HAc
II
HH
Calamus
quiquesetin
ervius
Stem
s[70]
110
Vanicosid
eAI
HH
AcG
GH
G
Polyg
onum
sachalinensis
Polyg
onum
cuspidatum
Polyg
onum
hydropiper
Stem
sLeaves
Rhizom
es[51527172]
111
Vanicosid
eBI
HH
HG
GH
G
Polyg
onum
sachalinensis
Polyg
onum
cuspidatum
Persica
riahydropiper
Stem
sLeaves
Rhizom
es[4351527172]
112
Vanicosid
eDG
HH
HG
GH
GPersica
riahydropiper
Leaves
[51]
113
Vanicosid
eEI
AcH
AcG
GH
GPolyg
onum
hydropiper
Stem
sand
leaves
[72]
114
LapathosideA
IH
HH
GG
HI
Polyg
onum
sachalinensis
Polyg
onum
cuspidatum
Fagopyrum
dibotrys
Stem
sRh
izom
es[5173]
115
LapathosideC
IH
HH
GG
HH
Polyg
onum
sachalinensis
Polyg
onum
cuspidatum
Stem
s[4352]
116
DibosideA
GH
HH
GI
HG
Fagopyrum
tataric
umFagopyrum
dibotrys
Roots
Rhizom
es[57]
117
Hidropiperosid
eAI
HH
HH
GH
GPolyg
onum
hydropiper
Stem
sand
leaves
[72]
118
Hidropiperosid
eBI
HH
AcG
GH
IPolyg
onum
hydropiper
Stem
sand
leaves
[72]
119
Tataris
ideB
IH
HAc
GG
HAc
Fagopyrum
tataric
umRo
ots
[57]
Evidence-Based Complementary and Alternative Medicine 11
Table2Con
tinued
Num
ber
Nam
eR 1
R 2R 3
R 4R 5
R 6R 7
R 8Source
Parts
Reference
120
Tataris
ideC
IAc
HAc
GG
HAc
Fagopyrum
tataric
umRo
ots
[57]
121
Tataris
ideD
GH
HAc
GI
HH
Fagopyrum
tataric
umRo
ots
[57]
122
Tataris
ideF
GH
HH
II
HG
Fagopyrum
tataric
umRo
ots
[57]
123
310158406-O
-Di-sinapoylsu
crose
KH
HH
KH
HH
Polyg
alatricornis
Polygalahongkongensis
Polyg
alasib
irica
Polyg
alatenu
ifolia
Cynanchu
mam
plexica
ule
Roots
Root
barks
Who
leplants
Aeria
lparts
[37ndash394153ndash
566974]
124
661015840-O
-Di-c
oumaroylsu
crose
GH
HH
HG
HH
Bidens
parviflora
Who
leplants
[61]
125
11015840 3101584061015840-O
-Tri-
coum
aroyl-6
-feruloylsucrose
IH
HH
GG
HG
Fagopyrum
tataric
umRo
ots
[7576]
126
3101584061015840-O
-Di-c
oumaroyl-110158406-O
-di-
feruloylsucrose
IH
HH
GG
HI
Fagopyrum
tataric
umRo
ots
[7576]
127
31015840-O
-Cou
maroyl-11015840610158406-O
-tri-
feruloylsucrose
IH
HH
IG
HI
Fagopyrum
tataric
umRo
ots
[7576]
128
11015840 31015840610158406-O
-Tetra-fe
ruloylsucrose
IH
HH
II
HI
Fagopyrum
tataric
umRo
ots
[7576]
SeeS
chem
e2
12 Evidence-Based Complementary and Alternative Medicine
131130129
CH2OHOH
OH
OO
OH
C
C
HH
HHO
OO
O
HO
HOHO
HO
HOOH
OHOHOH
OHOH
HOO
O
O
O
HO
HO
OH
OHOHOH
OHOH
HOO
O
O
O
HO
Figure 3
12
3
4
5
6
1998400
2998400
3998400
4998400
5998400
6998400
HO
O
O
R1O
R2O
R8O
R7OOR3
OR4 OR5OR6
Scheme 2
antidepressant cytotoxic antineoplastic anti-inflammatoryantidiabetic plant growth-regulatory neuroprotective andcerebral protective activities Lignan-derived disaccharideesters phenylpropanoid-derived tetrasaccharide esters andpentasaccharide esterswith biological activities have not beenreported Aside from the isolated constituents oligosaccha-ride mixtures from Rehmannia glutinosa Panax ginseng andScrophularia ningpoensiswere also reported to display diversepharmacological activities such as antidiabetic immunopo-tentiating enhanced memory and antineoplastic activitiesThese active compounds and mixtures could serve as thevaluable candidates to be developed as possible drugs for thetreatment and prevention of diseases
31 Antioxidant Activity The adverse effects of oxidativestress proposed to play significant roles in the pathogenesis ofcardiovascular diseases atherosclerosis hypertension can-cer diabetes mellitus neurodegenerative diseases rheuma-toid arthritis ischemiareperfusion injury and ageing havebecome an inevitable and serious issue [95 96] Scientistshave thus made great efforts to explore antioxidants frommedicinal plants by using different kinds of assay methodswhich include DPPH radical scavenging assay hydroxylradical scavenging assay superoxide anion scavenging assayand ABTS radical scavenging method [96]
Lapathosides C and D hydropiperoside vanicoside Bhidropiperosides A and B lapathoside A and diboside Awere isolated from the Polygonum Persicaria and Fagopyrumgenera belonging to the Polygonaceae family The DPPH testrevealed that free radical-scavenging activity of the isolatedcompounds termed lapathoside C (115) hydropiperoside(42) vanicoside B (111) and lapathoside D (38) increasedin turn and lapathoside D exhibited strongest scavengingability with an IC
50of 0088 120583M [43] Hidropiperosides A
and B (117 118) were reported to show obvious antioxidantresponse to DPPH radicals with the SC
50values of 234
and 267 120583gmL respectively while vanicoside E moderatelyexhibited the same activity with a SC
50value of 490 120583gmL
[72] Lapathoside A (114) and diboside A (116) just showedlower antioxidant activities with the SC
50values of 19948 and
16552 120583M respectively [73]Smiglasides A and B smilaside P 26-di-acetyl-3101584061015840-
di-feruloylsucrose helonioside B smilasides GndashL and het-erosmilaside were isolated from the Heterosmilax and Smi-lax genera Compared with ascorbic acid (IC
5014352 120583M)
used as positive control smiglasides A and B and smi-laside P (48 49 65) (IC
5033958 33066 and 31449 120583M
resp) showed higher antioxidant activities than 26-di-acetyl-3101584061015840-di-feruloylsucrose (73) and helonioside B (40) (IC
50
63166 and 51827120583M resp) [47] Additionally Nhiem et alreported that helonioside B heterosmilaside (104) and 26-di-acetyl-3101584061015840-di-feruloylsucrose exhibited important DPPHradical scavenging activities with the SC
50values of 91 127
and 87 120583gmL respectively [48] Compared with smilasidesG-I (57ndash59) (ED
50685ndash794120583M) smilasides JndashL (60ndash62)
showed higher radical scavenging activities with an ED50
value of 267ndash327120583M [44]Five quiquesetinerviusides AndashE (105ndash109) isolated from
the Calamus genus showed weak DPPH scavenging activ-ities (IC
50604ndash1018120583M) but exhibited better hydroxyl
radical scavenging activities (IC50
36ndash84 120583M) Moreoverquiquesetinerviuside C showed superoxide anion scaveng-ing activity with an IC
50value of about 1843 120583M [70]
Liu et al investigated the antioxidant capacity of 310158406-O-di-sinapoylsucrose (DISS) (123) by using the acceleratedsenescence-prone short-lived mice (SAMP) in vivo Theanalyses indicated that the activities of antioxidant enzymesof SOD and glutathione peroxidase ascended obviously inSAMP mice when amended with DISS 50mgkg MoreoverDISS could downregulate and even restore the level ofmalondialdehyde in SAMP model group [97]
From the above studies it can be concluded that oligosac-charide esters with antioxidant activities have been identifiedin the Polygonaceae Liliaceae Smilacaceae and Arecaceaefamilies The results of the antioxidant assays show that theincreased number of phenolic hydroxyl groups and acetylgroups could produce higher antioxidant activity Fan etal indicated that the increased number of phenylpropanoidgroups was not beneficial to free radical scavenging activity[43] Zhang et al pointed out that oligosaccharide esters withferuloyl groups exhibited better antioxidant activities thanthose with coumaroyl groups [44]
Evidence-Based Complementary and Alternative Medicine 13
Table 3 Fatty acid-derived disaccharide esters
Number Name R1 R2 Source Parts Reference132 61015840-O-Linoleylsucrose H O Astragalus membranaceus Roots [77]133 61015840-O-Palmitoylsucrose H P Astragalus membranaceus Roots [77]134 6-O-Palmitoylsucrose P H Astragalus membranaceus Roots [77]
135 61015840-O-Linolenoylsucrose H N Astragalus membranaceusEquisetum hiemale
RootsAerial parts [77 78]
136 6-O-Linoleylsucrose O H Astragalus membranaceus Roots [77]137 6-O-Myristoylsucrose Q H Astragalus membranaceus Roots [77]
138 6-O-[(7Z10Z13Z)-Hexadeca-71013-trienoyl]sucrose H R Equisetum hiemale Aerial parts [78]
139 6-O-[(7Z10Z)-Hexadeca-710-dienoyl]sucrose H S Equisetum hiemale Aerial parts [78]
See Scheme 3
12
3
4
5
6
1998400
2998400
3998400
4998400
5998400
6998400
HO
O
O
R1O
R2O
R8O
R7OOR3
OR4 OR5OR6
O
O
O
18
18
1616
16
14
N linolenoyl
O linoleyl
P palmitoyl
Q myristoyl
O
O
O
R hexadeca-71013-trienoyl
S hexadeca-710-dienoyl
Scheme 3
32 Antidepressant Activity The oligosaccharides obtainedfrom the Morinda genus not only show specific antidepres-sant and antistress activities but also have no suppression orexcitatory effects on central nervous system as well Whatis more they can be taken orally with little toxicity [21]The inulin-type hexasaccharide (IHS) (9) from Morindaofficinalis obviously exhibited cytoprotective activity whichcontributed to the antidepressant effect not only by providingthe PC12 with protection against Cort-induced lesion withIHS 0625 and 125 120583Mbut also by reducing theCort-induced[Ca2+]
119894overloading with IHS 25 and 10 120583M IHS 5 and
10 120583Mupregulated the nerve growth factormRNAexpressionin Cort-induced PC12 cells [22] Polygalatenosides A (181)and B (182) were isolated from the Polygala genus Theysignificantly inhibited the isotope-labeled RTI-55 binding to
norepinephrine transporter protein with the IC50
values of300 and 604 120583M respectively [91]
DISS and tenuifoliside A were isolated from the PolygalaandCynanchum genera Liu et al investigated the antidepres-sant effect of YZ ethanol extract based on the tail suspensiontest (TST) and forced swimming test (FST) which arethe ease-of-use and widely-accepted models for estimatingantidepressant activities in mice The results indicated thatYZ-50 fraction at a dose of 200mgkgwas able to significantlydecrease the immobility time in TST Furthermore YZ-50possessed ability to inhibit corticosterone-induced injury ofhuman neuroblastoma SH-SY5Y cells What is more DISS(123) and tenuifoliside A (44) two major compounds of YZ-50 fraction showed effective protective response to the lesionin SY5Y cells [53] The antidepressant-like effect of DISS at
14 Evidence-Based Complementary and Alternative Medicine
H3CO
HO
HOHO
HO
HO
HO
HOHO
O O
OO O
OO
O
O
O
OO
O
O
OH
OH
OH
OH
OCH3
OCH3
CH2OH
CH2OH
CH2OAc
CH2OAc
H3CO
HOHO
HO
O
O
O
OO
O
O
OH
OH
OH
OCH3
CH2OH
CH2OH
H3CO
H3CO H3CO
HOHO
HO
O
O
O
OO
O
O
OH
OH
OH
OCH3
CH2OH
CH2OAc
CH3O
H
HOHO
HO
HO
HOO O
OO O
OO
OH
OCH3
CH2OHCH2OH
H3CO H3CO
H
CH2CH2 HO
HO
HO
HO
HOO O
OO O
OO
OH
OCH3
CH2OHCH2OAc
H3CO
H
CH2
140 141 142
143 144 145
Figure 4
Table 4 Phenylpropanoid-derived trisaccharide esters
Number Name R1 R2 R3 R4 R5 R6 R7 Source Parts Reference146 Tricornose C K H H H H L H Polygala tricornis Roots [37]147 Tricornose D K H H H H K H Polygala tricornis Roots [37]148 Tricornose E K H H H K L H Polygala tricornis Roots [37]149 Tricornose F K H H H I L H Polygala tricornis Roots [37]See Scheme 4
O
OOO
O
R2O
R4O
R3O
R6O
OH
OH
OH
OH
OR1
OR5CH2OR7
Scheme 4
the doses of 5 10 and 20mgkg was also tested in chronicallymild stressed rats DISS was able to exhibit antidepressantactivity by upregulating the expression of noradrenergic-regulated plasticity genes including cell adhesion moleculeL1 brain-derived neurotrophic factor laminin and cAMP
response element binding protein factor in hippocampus[98] DISS improved the reward reaction by increasingsucrose intake and obviously decreased the levels of serumcortisol adrenocorticotrophic hormone and corticotropin-releasing factor Further DISS played an enhanced role inthe expression of mineralocorticoid receptor together withglucocorticoid receptor mRNA [99]
33 Cytotoxic and Antineoplastic Activities Smilasides AndashFand P smiglasides A and B smilaside P and helonioside Awere isolated from the Smilax Trillium and Paris generaKuo et al obtained smilasides AndashF (51ndash56) and evaluatedtheir cytotoxicity against human tumor cell lines comprisinghuman oral epithelium carcinoma (KB) human cervicalcarcinoma (Hela) human colon tumor (DLD-1) humanbreast adenocarcinoma (MCF-7) human lung carcinoma (A-549) and humanmedulloblastoma (Med) cells byMTTassayExperimental data indicated that all but smilaside C showedcytotoxicity against three to six human tumor cell lines(ED50
= 51ndash130 120583gmL) and smilasides DndashF (ED50
= 27ndash50 120583gmL) displayed strong cytotoxic activities against DLD-1 cells [46]Wang et al reported the antitumor constituents of
Evidence-Based Complementary and Alternative Medicine 15
OH
OH
OH
OH
OH
OHOH
OHOH
OHOH
OH
OHOHOH
OH
OH
OH
OHOH
OH
OH
OHOH
H
H H
HO
O
O
O
O
O
O
O
OO
OO
O
OO
O
HO
HO
HO
OO
O
O
OO
OO
O
OO
O
OO
O
OO
O
O
O
OO
O
O
OO
O
OO
OOOO
HO
HO
HO
HO
HO
HO
HO
HO
HO
HO
HOHO
HO
HO
HO
HO
HO
150 151 152
153 180
AcO
AcO
AcOAcO
OAc
OAc
CH2OH
OHOH
OH OHOH
OHOH
OH
OHOH
CH3O
Figure 5
Table 5 Phenylpropanoid-derived tetrasaccharide esters
Number Name R1 R2 R3 Source Parts Reference154 Tricornose G K H K Polygala tricornis Roots [37]155 Tricornose H K K K Polygala tricornis Roots [37]156 Tricornose I K K L Polygala tricornis Roots [37]157 Tricornose J K I L Polygala tricornis Roots [37]158 Tricornose K K I K Polygala tricornis Roots [37]159 Tricornose L K G K Polygala tricornis Roots [37]See Scheme 5
Smilax riparia including smiglasides A (48) and B (49) 26-di-acetyl-3101584061015840-di-feruloylsucrose (73) helonioside B (40)and smilaside P (65) Only smiglasidesA andB and smilasideP exhibited cytotoxicity against human tumor cell lines withdifferent inhibitory concentrations comparing with cisplatinand paclitaxel as positive controls [47] Helonioside A (39)exhibited higher cytotoxicity with the increase of concentra-tion (01ndash100120583gmL) [45] Tatarisides AndashG (45 119ndash121 46122 47) and diboside A (116) from the Fagopyrum genusexerted cytotoxic activities against different human cell linesand the cytotoxicity of tatariside C was the most remarkablewith the IC
50values ranging from 644 to 749 120583gmL [57]
11015840236-O-Tetra-acetyl-31015840-O-cis-feruloylsucrose (95) fromthe Sparganium plants exhibited extremely weak cyto-toxicity against the growth of mice Lung Adenocarcinoma
795 cell lines with an IC50
value of 116 120583gmL [66] SnS-2oligosaccharides mixture including raffinose (3) stachyose(19) and verbascose (21) from the roots of Scrophularianingpoensis had antitumor activity against the growth ofLewis pulmonary carcinoma cells transplanted into mice[18]
Disaccharide esters and oligosaccharides mixture fromthe Liliaceae Polygonaceae Sparganiaceae and Scrpophular-iaceae families showed effective cytotoxic and antineoplasticactivities The study results indicated that feruloyl and acetylgroups play an important role in mediating cytotoxicitywhich seems to be related to the substitution position offeruloyl groups The feruloyl groups at C-6 or C-11015840 are vitalfor cytotoxicity In addition the increased number of acetylgroups could induce higher tumoricidal activity
16 Evidence-Based Complementary and Alternative Medicine
Table 6 Phenylpropanoid-derived pentasaccharide esters
Number Name R1 R2 R3 R4 R5 R6 Source Parts Reference160 Tenuifoliose A G D I Ac Ac Ac Polygala tenuifolia Roots [38 42]161 Tenuifoliose B G D I H Ac Ac Polygala tenuifolia Roots [42]162 Tenuifoliose C G D I H H H Polygala tenuifolia Roots [42]163 Tenuifoliose F G D U Ac Ac Ac Polygala tenuifolia Roots [42]164 Tenuifoliose G G D U Ac H Ac Polygala tenuifolia Roots [42]165 Tenuifoliose H G D G Ac Ac Ac Polygala tenuifolia Roots [38 42 79]166 Tenuifoliose I G D G Ac H Ac Polygala tenuifolia Roots [42 79]167 Tenuifoliose J G D G H Ac Ac Polygala tenuifolia Roots [42]168 Tenuifoliose K G D G H H Ac Polygala tenuifolia Roots [42]169 Tenuifoliose L G D T Ac Ac Ac Polygala tenuifolia Roots [42 79]170 Tenuifoliose M G D T Ac H Ac Polygala tenuifolia Roots [42]171 Tenuifoliose N I D I Ac Ac Ac Polygala tenuifolia Roots [42]172 Tenuifoliose O I D I H Ac Ac Polygala tenuifolia Roots [42]173 Tenuifoliose P I D I H H Ac Polygala tenuifolia Roots [42]174 Tenuifoliose Q G D T H Ac Ac Polygala tenuifolia Roots [79]175 Tenuifoliose S G D G H H H Polygala tenuifolia Roots [42]176 Tenuifoliose T G D I H H H Polygala tenuifolia Roots [42]177 Tenuifoliose V H D I Ac Ac Ac Polygala tenuifolia Roots [42]178 Tenuifoliose W I D U Ac H Ac Polygala tenuifolia Roots [42]179 Tenuifoliose X I D I H H H Polygala tenuifolia Roots [42]See Scheme 6
O
OO
O
O
O
O
OR1
OH
OH
OH
OHOH
OH
HOHO
HO
HO
OR2
R3O
CH2OH
Scheme 5
34 Anti-Inflammatory Activity Inflammation an importantbasic pathological process is a defense response of biopsywith vascular system to damage stimuli such as pathogensimpaired cells and tissues and physical and chemical factorsHowever if the process of inflammatory response cannot endnormally when cell debris and pathogens were cleared thebiological defence response will become causative factor andbring about many diseases such as diabetes cardiovasculardiseases metabolic syndrome and cancer [100 101]
Tenuifoliside A (44) from the Polygala genus exhibitedstrong anti-inflammatory effect not only by suppressing the
production of NO but also by reducing the production ofiNOS prostaglandin E2 cyclooxygenase-2 and proinflam-matory cytokines through the inhibition of the mitogen-activated protein kinases pathway and NF-120581B pathway [102]The anti-inflammatory activities of quiquesetinerviusides D(108) and E (109) from the Calamus genus were evaluated inRAW 2647 cells Both of them showed significant inhibitoryeffects against the production of LPS-stimulated NOwith theIC50values of 90ndash295120583M [70]Six disaccharide fatty acid esters (132ndash137) were iso-
lated from the Astragalus and Equisetum genera The anti-inflammatory effects of these isolated compounds have alsobeen documented The activation of NF-120581B could upregulatethe expression of proinflammatory cytokines inducible nitricoxide synthase (iNOS) and tumornecrosis factor alpha (TNF-120572) The NF-120581B inhibitory activities of compounds 132ndash137were tested in HepG2 cells stimulated with TNF-120572 All ofthese compounds could significantly restrainTNF-120572-inducedNF-120581B transcriptional activities with the IC
50values of 44ndash
247 120583M Li et al pointed out that olefinic bonds and thelength of the fatty acid moieties contributed to the NF-120581B inhibitory activity Furthermore the inhibition increasedsignificantly with the increase of the number of olefinic bondson the aliphatic moiety [77] These results may provide ascientific basis for the development of new anti-inflammatoryagents
35 Neuroprotective and Cerebral Protective Activities Aswe all know glutamate works as a major excitatory aminoacid neurotransmitter in the mammalian central nervous
Evidence-Based Complementary and Alternative Medicine 17
R6O
R2O
OR3
OR5
OR4
CH2OR1
OCH3
Rham
OO
O
OO O
O
O
O
OO
RhamO
O
OH
OH
OHOH
OH
OHOH
OHHO
HO
HO
T O-rhamnosyl-coumaroyl U O-rhamnosyl-feruloyl
Scheme 6
system and plays a crucial role in several physiological pro-cesses [103] However the accumulation of glutamate inducesdiverse acute and chronic neurodegenerative diseases suchas epilepsy ischemic stroke and Parkinsonrsquos disease aswell as Alzheimerrsquos disease [104] DISS (123) isolated fromthe Polygala genus exhibited neuroprotective effect againstglutamate-induced SH-SY5Y neuronal cell damage The invitro test demonstrated that DISS (06 6 and 60 120583molL)played a critical role in increasing cell viability controllinglactate dehydrogenase and attenuated apoptosis ranging from195 to 258 [105]
Tenuifoliside B (102) from the Polygala genus was ableto significantly shorten the coma time of KCN-inducedanoxia mice at the doses of 3 and 10mgkg and it playedan important role in ameliorating the scopolamine-inducedimpairment of performance in passive avoidance task inrats and enhancing the tremors induced by oxotremorine inmiceThese results together demonstrated that tenuifoliside Bpossessed cognitive improving and cerebral protective effects[56]
36 Antidiabetic Activity Diabetes mellitus a chronic debil-itating metabolic disease is characterized by high bloodglucose content and comprises three types termed type Itype II and gestational diabetes [106] Stachyose (19) extract(a part) from Rehmannia glutinosa obviously exhibited theactivity of downregulating fasting plasma glucose level andpartially keeping from hyperglycemia induced by adrenalineand glucose without obvious dose-dependent effect Otherthan that in vivo tests in rats induced by alloxan revealed
that stachyose extract at the dose of 200mgkg significantlydecreased blood-sugar level [15]
Diboside A lapathosides C and D vanicosides A andB and hydropiperoside were isolated from the FagopyrumPolygonum and Persicaria genera belonging to the Polygo-naceae family Diboside A (116) could potentially inhibit 120572-amylase activity with an IC
50of 269 120583M and thus retard the
starch digestion rate which is helpful for diabetic individualsin controlling blood sugar level [107] Lapathoside D (38)exerted stronger activity of 120572-glucosidase inhibition with anIC50
value of 0113mM than acarbose which was chosen asa positive drug for the treatment of type II diabetes [43]Vanicoside B (111) was reported to have higher 120573-glucosidaseinhibitory activity with an IC
50of 505 120583M than vanicoside A
(110) with an IC50of 599 120583M because of the acetyl moiety of
the latter possibly decreasing inhibitory activity of vanicosideA [71]
Fujimoto et al investigated the inhibitory effects ofmumeoses FndashO (83ndash92) from the Prunus genus on aldosereductase and discovered that caffeoyl groups are crucialfor the inhibitory effect on aldose reductase And thusmumeoses F G H J K L M and N (IC
50= 22ndash77120583M) with
a coumaroyl group and acetyl groups inhibited moderatelyaldose reductase from reducing glucose to sorbitol whichis associated with the chronic complications of diabetes [6364]
37 Elicitors and Regulators Oligosaccharides are quitepropitious for encoding biological information because ofdiverse monosaccharide units and complex molecular struc-tures and they are therefore first described as biological
18 Evidence-Based Complementary and Alternative Medicine
181 H
H
H
H
H
H
H
H
H H
H
H
H
H
H
H
H H
HH
Benzyl
Benzyl
Benzyl
182
183
184 Ac
Ac
Ac
Ac
Ac
Ac
Ac
Ac
Ac
Ac
185
186
187
188
189
R1 R2 R3
R1 R2 R3 R4
OCH3
R3OH2C OR2
OR1
OR1
O
O
O
O O
OOO
O
OO
O
OH
OH
OH OH
OH
O O
O
O
OH
HO
OH
OH OHOH
OH
OH
OHHO
HO
OH
OH
HO
CH2OH
CH2OH
CH2OH
CH2OH
C
R2O
R3O
CH2OR4
CH2CH2 CH2CH2CH2CH2CH3
CH3
CH3
191190 192
193
O
C C
O
OO
OO
OO
OO
O O
O
O
O
O
O
O
OH
OH
OHHO
HO
HOOH
OH
OH
OH
HO
OH
OH
OH
OH
HO
HO
C C
R998400O
R998400
Figure 6
signals in plants [108] Oligosaccharides from the cell wallfragments of plants and fungi are powerful signal moleculessuch as the elicitors of plant defence response and theregulators of plant growth and they are capable of exertingbiological activities at exceedingly low concentrations [109]Heptasaccharide (HS) (15) and octasaccharide (OS) (16) iso-lated from the Paris genus possessed plant growth-regulatory
activities [29 30]The two oligosaccharides significantly pro-moted the proliferation of Paris polyphylla var yunnanensisroots at the doses of 25ndash20mgL The octasaccharide hadthe most obvious effect on the growth of Panax japonicusvar major hairy roots at a dose of 30mgL while the otherhad the most positive effect on saponin accumulation ofPanax japonicus var major hairy roots at a dose of 10mgL
Evidence-Based Complementary and Alternative Medicine 19
[29] Similarly Zhou et al evaluated the stimulating effectsof HS and OS on the root growth and saponin productionof Panax ginseng hairy roots which were induced from theplant roots infected withAgrobacterium rhizogenes strain A4The results showed that there was a maximum effect on thehairy roots growth and saponin accumulation on day 10Compared with control group the root biomass dry weightwas increased by more than 17-fold while the total saponincontent of roots increased by more than 1-fold when thesetwo oligosaccharides were added to the hairy root at a dose of30mgL [30] The above data illustrate that HS and OS couldserve as the plant growth-regulators not only in their originalspecies but also in others
38 Immunopotentiating Activity Macrophages are impor-tant targets of investigations on cytophagy cellular immunityand molecular immunology Therefore they are deemedto play a vital role in host defense comprising phagocy-tosis proteolytic processing pathogenic agent apoptosiscytokines production and foreign antigens presentation[110] The water-extracted oligosaccharides from Panax gin-seng (WGOS) exhibited better immunopotentiating activ-ity by increasing phagocytic function of macrophages andpromoting NO TNF-120572 and reactive oxygen species pro-duction [110] In addition Wan et al have obtained malto-oligosaccharides (17 119899 = 3sim8) and three oligosaccharides (213 14) from the Panax ginseng roots The in vitro bioassaypointed out thatWGOS could serve as efficacious stimulatorsof B and T lymphocytes [28] These studies provided enlight-enment that the mixture of oligosaccharides from Chineseherbalmedicine exhibits significant effect on immune system
39 Others Acetylcholinesterase (AChE) inhibitors showgood therapeutic effects onmyasthenia gravis glaucoma andAlzheimerrsquos disease through reversible enzyme inhibitionso as to increase the accumulation of acetylcholine in thesynapse and then promote and prolong the function ofacetylcholine Vanicoside B (111) showed AChE inhibitoryactivity with an IC
50of 0062mM while hydropiperoside
(42) and lapathosides C (115) and D (38) just exhibited weakenzyme inhibitory activity [43]
Wang et al has explored low molecular mass carbohy-drate polymer from Panax ginseng roots and obtained 30ethanol elution (PGO)which included peptides and oligosac-charides (17 119899 = 0sim5) identified as maltose maltotriosemaltotetraose maltopentaose maltohexaose and maltohep-taose Pharmacological experiments revealed that PGO couldsignificantly enhance the memory in scopolamine-inducedmemory deficit rats [27]
Cistanoside F (129) and kankanose (150) were isolatedfrom the Cistanche Paulownia and Acanthus genera Phar-macological experiments showed that cistanoside F andkankanose significantly exhibited vasorelaxant effects on thenoradrenaline-induced contraction of thoracic aorta fromrats [80]
4 Conclusion
Traditional Chinese medicine from natural kingdom playsan indelible role in the treatment of human diseases andit has aroused the attention of those who have engagedin medicinal pharmaceutical chemistry Therefore scientistshave made great contributions day after day to investigate thevalid chemicals from traditional Chinese medicines In thepast decades about 193 oligosaccharides and their esters havebeen identified from traditional Chinese medicinal plantsOn the one hand only a few oligosaccharides and theirmixtures were investigated and just exhibited antidepres-sant antineoplastic antidiabetic plant growth-regulatoryimmunopotentiating and enhancedmemory activitiesMoreexploratory work is still needed to excavate biological andpharmacological activities of oligosaccharides On the otherhand oligosaccharide esters exhibited multi-advantageousactivities Bioassays have revealed that antioxidant cytotoxicantineoplastic and anti-inflammatory activities are the mostnotable bioactivities Of course to search for the naturalproducts with these activities is a hotpot in the contemporarydrug research Oligosaccharide esters provide a vast treasuretrove for medical researchers After considering the currentstudies it should be taken as future directions to makemore mechanism of action studies and clinical trials tofurther evaluate its potential as new drugs Moreover thestructure-activity relationships discussed in this review willprovide reference information for further exploring theirrelationships and continually discovering the new bioactiveoligosaccharide esters
Conflict of Interests
The authors declare that there is no conflict of interestsregarding the publication of this paper
References
[1] X D Yang L J Zhang B Liang L Z Xu and S L YangldquoOligosaccharide esters isolated from plants of PolygalaceaerdquoChinese Traditional and Herbal Drugs vol 33 no 10 pp 954ndash958 2002
[2] N Ogwuru and M Adamczeski ldquoBioactive natural productsderived from Polygonum species of plants their structures andmechanisms of actionrdquo Studies in Natural Products Chemistryvol 22 pp 607ndash642 2000
[3] S Kobayashi T Miyase and H Noguchi ldquoPolyphenolic glyco-sides and oligosaccharide multiesters from the roots of Polygaladalmaisianardquo Journal of Natural Products vol 65 no 3 pp 319ndash328 2002
[4] M Takasaki S Kuroki M Kozuka and T Konoshima ldquoNewphenylpropanoid esters of sucrose from Polygonum lapathi-foliumrdquo Journal of Natural Products vol 64 no 10 pp 1305ndash1308 2001
[5] M L Zimmermann and A T Sneden ldquoVanicosides A and Bprotein kinase C inhibitors from Polygonum pensylvanicumrdquoJournal of Natural Products vol 57 no 2 pp 236ndash242 1994
[6] M Takasaki T Konoshima S Kuroki H Tokuda and HNishino ldquoCancer chemopreventive activity of phenylpropanoid
20 Evidence-Based Complementary and Alternative Medicine
esters of sucrose vanicoside B and lapathoside A from Poly-gonum lapathifoliumrdquo Cancer Letters vol 173 no 2 pp 133ndash138 2001
[7] Q Fu T Liang Z Y Li et al ldquoSeparation of carbohydrates usinghydrophilic interaction liquid chromatographyrdquo CarbohydrateResearch vol 379 pp 13ndash17 2013
[8] M F Mrozek D Zhang and D Ben-Amotz ldquoOligosaccharideidentification and mixture quantification using Raman spec-troscopy and chemometric analysisrdquo Carbohydrate Researchvol 339 no 1 pp 141ndash145 2004
[9] G S Armstrong and B Bendiak ldquoHigh-resolution four-dimen-sional carbon-correlated 1H-1H ROESY experiments employ-ing isotags and the filter diagonalization method for effectiveassignment of glycosidic linkages in oligosaccharidesrdquo Journalof Magnetic Resonance vol 181 no 1 pp 79ndash88 2006
[10] G S Armstrong V A Mandelshtam A J Shaka and BBendiak ldquoRapid high-resolution four-dimensional NMR spec-troscopy using the filter diagonalization method and its advan-tages for detailed structural elucidation of oligosaccharidesrdquoJournal of Magnetic Resonance vol 173 no 1 pp 160ndash168 2005
[11] H-M Tseng S Gattolin J Pritchard H J Newbury and DA Barrett ldquoAnalysis of mono- di- and oligosaccharides by CEusing a two-stage derivatization method and LIF detectionrdquoElectrophoresis vol 30 no 8 pp 1399ndash1405 2009
[12] N Li X Li B L Hou and D L Meng ldquoNew disaccharosidefrom Camptosorus sibiricus Ruprrdquo Natural Product Researchvol 22 no 15 pp 1379ndash1383 2008
[13] Z Zhang D Wang Y Zhao H Gao Y-H Hu and J-FHu ldquoFructose-derived carbohydrates from Alisma orientalisrdquoNatural Product Research vol 23 no 11 pp 1013ndash1020 2009
[14] X Yang Y Zhao N He and K D Croft ldquoIsolation char-acterization and immunological effects of 120572-galacto-oligo-saccharides from a new source the herb Lycopus lucidus TurczrdquoJournal of Agricultural and Food Chemistry vol 58 no 14 pp8253ndash8258 2010
[15] R X Zhang Z P Jia L Y Kong et al ldquoStachyose extractfrom Rehmannia glutinosa Libosch to lower plasma glucose innormal and diabetic rats by oral administrationrdquo Pharmazievol 59 no 7 pp 552ndash556 2004
[16] R Zhang Y Zhao Y Sun X Lu and X Yang ldquoIsolationcharacterization and hepatoprotective effects of the raffinosefamily oligosaccharides from Rehmannia glutinosa liboschrdquoJournal of Agricultural and Food Chemistry vol 61 no 32 pp7786ndash7793 2013
[17] H Li F Song Z Zheng Z Liu and S Liu ldquoCharacterization ofsaccharides and phenolic acids in the Chinese herb Tanshen byESI-FT-ICR-MS and HPLCrdquo Journal of Mass Spectrometry vol43 no 11 pp 1545ndash1552 2008
[18] J E Deng J Zhang XM ChenW Ke and G Y Tian ldquoStudieson the physicochemical properties structure and antitumoractivity of an oligosaccharide homologue SnS-2 from the root ofScrophularia ningpoensis Hemslrdquo Chinese Journal of Chemistryvol 22 no 5 pp 492ndash497 2004
[19] S C Chou LM Chuang and S S Lee ldquoHypoglycemic constit-uents of gynura divaricata subsp formosanardquo Natural ProductCommunications vol 7 no 2 pp 221ndash222 2012
[20] F Feng L-L Wang X-P Lai Y-B Li Z-M Cao and Y-J Zhou ldquoStudy on oligosaccharides from Morinda officinalisrdquoJournal of Chinese Medicinal Materials vol 35 no 8 pp 1259ndash1262 2012
[21] Y F Li Z H Gong M Yang Y M Zhao and Z P Luo ldquoInhibi-tion of the oligosaccharides extracted fromMorinda officinalis
a Chinese traditional herbal medicine on the corticosteroneinduced apoptosis in PC12 cellsrdquo Life Sciences vol 72 no 8 pp933ndash942 2003
[22] Y-F Li Y-Q Liu M Yang et al ldquoThe cytoprotective effect ofinulin-type hexasaccharide extracted from Morinda officinalison PC12 cells against the lesion induced by corticosteronerdquo LifeSciences vol 75 no 13 pp 1531ndash1538 2004
[23] D N Olennikov L M Tankhaeva and A V Rokhin ldquoGlu-cofructans from Saussurea lappa rootsrdquo Chemistry of NaturalCompounds vol 47 no 3 pp 339ndash342 2011
[24] S K Hyun H A Jung B S Min J H Jung and J S ChoildquoIsolation of phenolics nucleosides saccharides and an alkaloidfrom the root of Aralia cordatardquo Natural Product Sciences vol16 no 1 pp 20ndash25 2010
[25] Z J Xu C W Lin and M F Liao ldquoStructure analysis of a newoligosaccharides BROS from Blumea ripariardquo Chinese Journalof Organic Chemistry vol 31 no 11 pp 1811ndash1819 2011
[26] Z J Xu C W Lin and Y Shi ldquoIsolation and structuredetermination of a new oligosaccharide from Blume ripariardquoJournal of Medicinal Plants Research vol 5 no 14 pp 2956ndash2962 2011
[27] Y Wang R Z Jiang G R Li et al ldquoStructural and enhancedmemory activity studies of extracts from Panax ginseng rootrdquoFood Chemistry vol 119 no 3 pp 969ndash973 2010
[28] DWan L Jiao H Yang and S Liu ldquoStructural characterizationand immunological activities of the water-soluble oligosaccha-rides isolated from thePanax ginseng rootsrdquoPlanta vol 235 no6 pp 1289ndash1297 2012
[29] L G Zhou C Z Yang J Q Li S L Wang and J Y WuldquoHeptasaccharide and octasaccharide isolated from Paris pol-yphylla var yunnanensis and their plant growth-regulatoryactivityrdquo Plant Science vol 165 no 3 pp 571ndash575 2003
[30] L G Zhou X D Cao R F Zhang Y L Peng S J Zhao andJ Y Wu ldquoStimulation of saponin production in Panax ginsenghairy roots by two oligosaccharides from Paris polyphylla varyunnanensisrdquo Biotechnology Letters vol 29 no 4 pp 631ndash6342007
[31] M Vanhaecke W van den Ende E Lescrinier and N Dyu-bankova ldquoIsolation and characterization of a pentasaccharidefrom Stellaria mediardquo Journal of Natural Products vol 71 no 11pp 1833ndash1836 2008
[32] J Feng and W Zhao ldquoComplete 1Hand 13C NMR assignmentsof four new oligosaccharides and two new glycosides fromPeriploca forrestiirdquoMagnetic Resonance in Chemistry vol 47 no8 pp 701ndash705 2009
[33] J Q Feng R J Zhang Y Zhou et al ldquoImmunosuppressive preg-nane glycosides from Periploca sepium and Periploca forrestiirdquoPhytochemistry vol 69 no 15 pp 2716ndash2723 2008
[34] X H Long R Xu Y H Zhang X H Tan andQ Y Sun ldquoA newoligosaccharide from Periploca calophyllardquo Zhongguo ZhongyaoZazhi vol 37 no 2 pp 226ndash229 2012
[35] L Wang Z-Q Yin Y Wang X-Q Zhang Y-L Li and W-CYe ldquoPerisesaccharides A-E new oligosaccharides from the rootbarks ofPeriploca sepiumrdquoPlantaMedica vol 76 no 9 pp 909ndash915 2010
[36] T Lei L Zhang H-Y Jiang Y Hu A-H Hong and Y-Z CenldquoA new pregnane glycoside and oligosaccharide from Parabar-ium huaitingiirdquo Journal of Asian Natural Products Research vol13 no 11 pp 1030ndash1035 2011
[37] J Li Y Jiang and P F Tu ldquoTricornoses A-L oligosaccharidemulti-esters from the roots of Polygala tricornisrdquo Journal ofNatural Products vol 68 no 5 pp 739ndash744 2005
Evidence-Based Complementary and Alternative Medicine 21
[38] H H Tu P Liu L Mu et al ldquoStudy on antidepressant com-ponents of sucrose ester from Polygala tenuifoliardquo ZhongguoZhongyao Zazhi vol 33 no 11 pp 1278ndash1280 2008
[39] G M She Y Y Ba Y Liu H Lv W Wang and R B ShildquoAbsorbable phenylpropenoyl sucroses from Polygala tenuifo-liardquoMolecules vol 16 no 7 pp 5507ndash5513 2011
[40] J Yong and P F Tu ldquoStudies on the chemical constituents inroot bark of Polygala tenuifolia (II)rdquo China Journal of ChineseMateria Medica vol 29 no 8 pp 751ndash753 2004
[41] M Ono C Takamura F Sugita et al ldquoTwo new steroidglycosides and a new sesquiterpenoid glycoside from theunderground parts of Trillium kamtschaticumrdquo Chemical andPharmaceutical Bulletin vol 55 no 4 pp 551ndash556 2007
[42] Y Ling Z Li M Chen Z Sun M Fan and C HuangldquoAnalysis and detection of the chemical constituents of RadixPolygalae and their metabolites in rats after oral administrationby ultra high-performance liquid chromatography coupledwith electrospray ionization quadrupole time-of-flight tandemmass spectrometryrdquo Journal of Pharmaceutical and BiomedicalAnalysis vol 85 pp 1ndash13 2013
[43] P Fan L Terrier A-E Hay A Marston and K HostettmannldquoAntioxidant and enzyme inhibition activities and chemicalprofiles ofPolygonum sachalinensis FSchmidt exMaxim (Polyg-onaceae)rdquo Fitoterapia vol 81 no 2 pp 124ndash131 2010
[44] L J Zhang C C Liao H C Huang Y C Shen L M Yangand Y H Kuo ldquoAntioxidant phenylpropanoid glycosides fromSmilax bracteatardquo Phytochemistry vol 69 no 6 pp 1398ndash14042008
[45] L L Yan W Y Gao Y J Zhang and Y Wang ldquoA new phenyl-propanoid glycosides from Paris polyphylla var yunnanensisrdquoFitoterapia vol 79 no 4 pp 306ndash307 2008
[46] Y H Kuo Y W Hsu C C Liaw J K Lee H C Huang andL M Y Kuo ldquoCytotoxic phenylpropanoid glycosides from thestems of Smilax chinardquo Journal of Natural Products vol 68 no10 pp 1475ndash1478 2005
[47] W-X Wang T-X Li H Ma J-F Zhang and A-Q JialdquoTumoral cytotoxic and antioxidative phenylpropanoid glyco-sides in Smilax riparia A DCrdquo Journal of Ethnopharmacologyvol 149 no 2 pp 527ndash532 2013
[48] N X Nhiem P vanKiem C vanMinh et al ldquoPhenylpropanoidglycosides fromHeterosmilax erythrantha and their antioxidantactivityrdquo Archives of Pharmacal Research vol 32 no 10 pp1373ndash1377 2009
[49] Y Wang W Y Gao T J Zhang and Y Q Guo ldquoA novelphenylpropanoid glycosides and a new derivation of phenolicglycoside from Paris Polyphylla var yunnanensisrdquo ChineseChemical Letters vol 18 no 5 pp 548ndash550 2007
[50] J-Y Zhang Y-Z Wang Y-L Zhao et al ldquoPhytochemicals andbioactivities of Paris speciesrdquo Journal of Asian Natural ProductsResearch vol 13 no 7 pp 670ndash681 2011
[51] N H N Hashim F Abas K Shaari and N H Lajis ldquoLC-DAD-ESIMSMS characterization of antioxidant and anti-cholinesterase constituents present in the active fraction fromPersicaria hydropiperrdquo LWT Food Science and Technology vol46 no 2 pp 468ndash476 2012
[52] PH FanA EHayAMarstonHX Lou andKHostettmannldquoChemical variability of the invasive neophytes Polygonumcuspidatum Sieb and Zucc and Polygonum sachalinensis FSchmidt ex Maximrdquo Biochemical Systematics and Ecology vol37 no 1 pp 24ndash34 2009
[53] P Liu Y Hu D H Guo et al ldquoPotential antidepressantproperties of Radix Polygalae (Yuan Zhi)rdquo Phytomedicine vol17 no 10 pp 794ndash799 2010
[54] J F Wu S B Chen S L Chen and P F Tu ldquoThe chemical con-stituents of Polygala hongkongensisHemslrdquoActa PharmaceuticaSinica vol 42 no 7 pp 757ndash761 2007
[55] Y Song Y Jiang D Bi X Tian L Liang and P Tu ldquoChemicalconstituents from n-butanol extract of aerial part of Polygalasibiricardquo Zhongguo Zhongyao Zazhi vol 37 no 4 pp 471ndash4742012
[56] Y Ikeya S Takeda M Tunakawa et al ldquoCognitive improvingand cerebral protective effects of acylated oligosaccharides inPolygala tenuifoliardquo Biological and Pharmaceutical Bulletin vol27 no 7 pp 1081ndash1085 2004
[57] C J Zheng C L Hu X Q Ma C Peng H Zhang and L PQin ldquoCytotoxic phenylpropanoid glycosides from Fagopyrumtataricum (L) Gaertnrdquo Food Chemistry vol 132 no 1 pp 433ndash438 2012
[58] X Li Y F Zhang L Yang et al ldquoChemical profiling ofconstituents of Smilacis glabrae using ultra-high pressure liquidchromatography coupled with LTQ orbitrap mass spectrome-tryrdquo Natural Product Communications vol 7 no 2 pp 181ndash1842012
[59] T-T Sun D-W Zhang Y Han F-Y Dong andWWang ldquoSmi-lasides M and N two new phenylpropanoid glycosides fromSmilax ripariardquo Journal of Asian Natural Products Research vol14 no 2 pp 165ndash170 2012
[60] J Li X Bi G Zheng Y Hitoshi T Ikeda and T NoharaldquoSteroidal glycosides and aromatic compounds from Smilaxripariardquo Chemical amp Pharmaceutical Bulletin vol 54 no 10 pp1451ndash1454 2006
[61] N Wang X Yao R Ishii and S Kitanaka ldquoBioactive sucroseesters from Bidens parviflorardquo Phytochemistry vol 62 no 5 pp741ndash746 2003
[62] S Nakamura K Fujimoto T Matsumoto et al ldquoAcylatedsucroses and acylated quinic acids analogs from the flower budsof Prunus mume and their inhibitory effect on melanogenesisrdquoPhytochemistry vol 92 pp 128ndash136 2013
[63] K Fujimoto SNakamura TMatsumoto et al ldquoMedicinal flow-ers XXXVIII Structures of acylated sucroses and inhibitoryeffects of constituents on aldose reducatase from the flower budsofPrunusmumerdquoChemical and Pharmaceutical Bulletin vol 61no 4 pp 445ndash451 2013
[64] S Nakamura K Fujimoto T Matsumoto et al ldquoStructuresof acylated sucroses and an acylated flavonol glycoside andinhibitory effects of constituents on aldose reductase from theflower buds of Prunus mumerdquo Journal of Natural Medicines vol67 no 4 pp 799ndash806 2013
[65] L-B Dong J He X-Y Li et al ldquoChemical constituents fromthe aerial parts of Musella lasiocarpardquo Natural Products andBioprospecting vol 1 no 1 pp 41ndash47 2011
[66] Y Xiong K Z Deng Y Q Guo W Y Gao and T J ZhangldquoNew chemical constituents from the rhizomes of Sparganiumstoloniferumrdquo Archives of Pharmacal Research vol 32 no 5 pp717ndash720 2009
[67] Y Xiong K-Z Deng Y-Q Guo W-Y Gao and T-J ZhangldquoTwo new sucrose esters from Sparganium stoloniferumrdquo Jour-nal of Asian Natural Products Research vol 10 no 5 pp 425ndash428 2008
[68] B Chen N L Wang J H Huang and X S Yao ldquoIridoidand phenylpropanoid glycosides from Scrophularia ningpoensis
22 Evidence-Based Complementary and Alternative Medicine
Hemslrdquo Asian Journal of Traditional Medicines vol 2 no 3 pp119ndash123 2007
[69] H Chen Y Z Zhou L Qiao et al ldquoTwo new compounds fromCynanchum amplexicaulerdquo Journal of Asian Natural ProductsResearch vol 10 no 3 pp 248ndash251 2008
[70] C-L Chang L-J Zhang R Y Chen et al ldquoAntioxidant andanti-inflammatory phenylpropanoid derivatives from Calamusquiquesetinerviusrdquo Journal of Natural Products vol 73 no 9 pp1482ndash1488 2010
[71] Y Kawai H Kumagai H Kurihara K Yamazaki R Sawanoand N Inoue ldquo120573-Glucosidase inhibitory activities of phenyl-propanoid glycosides vanicoside A and B from Polygonumsachalinense rhizomerdquo Fitoterapia vol 77 no 6 pp 456ndash4592006
[72] P V Kiem N X Nhiem N X Cuong et al ldquoNew phenyl-propanoid esters of sucrose from Polygonum hydropiper andtheir antioxidant activityrdquo Archives of Pharmacal Research vol31 no 11 pp 1477ndash1482 2008
[73] K J Wang Y J Zhang and C R Yang ldquoAntioxidant phenolicconstituents from Fagopyrum dibotrysrdquo Journal of Ethnophar-macology vol 99 no 2 pp 259ndash264 2005
[74] N Cho J Huh H Yang et al ldquoChemical constituentsof Polygala tenuifolia roots and their inhibitory activity onlipopolysaccharide-induced nitric oxide production in BV2microgliardquo Journal of Enzyme Inhibition and Medicinal Chem-istry vol 27 no 1 pp 1ndash4 2012
[75] Q Ren C S Wu and J L Zhang ldquoUse of on-line stop-flowheart-cutting two-dimensional high performance liquid chro-matography for simultaneous determination of 12 major con-stituents in tartary buckwheat (Fagopyrum tataricum Gaertn)rdquoJournal of Chromatography A vol 1304 pp 257ndash262 2013
[76] Q Ren C S Wu Y Ren and J L Zhang ldquoCharacterizationand identification of the chemical constituents from tartarybuckwheat (Fagopyrum tataricumGaertn) by high performanceliquid chromatographyphotodiode array detectorlinear iontrap FTICR hybrid mass spectrometryrdquo Food Chemistry vol136 no 3-4 pp 1377ndash1389 2013
[77] W Li Y N Sun X T Yan et al ldquoNF-120581B inhibitory activityof sucrose fatty acid esters and related constituents fromAstragalus membranaceusrdquo Journal of Agricultural and FoodChemistry vol 61 no 29 pp 7081ndash7088 2013
[78] J T Cheng J He Y Li et al ldquoThree new sucrose fatty acid estersfrom Equisetum hiemale LrdquoHelvetica Chimica Acta vol 95 no7 pp 1158ndash1163 2012
[79] Y Jiang and P-F Tu ldquoTenuifoliose Q a new oligosaccharideester from the root of Polygala tenuifoliaWilldrdquo Journal of AsianNatural Products Research vol 5 no 4 pp 279ndash283 2003
[80] M Yoshikawa H Matsuda T Morikawa H H Xie S Naka-mura and O Muraoka ldquoPhenylethanoid oligoglycosides andacylated oligosugars with vasorelaxant activity from Cistanchetubulosardquo Bioorganic ampMedicinal Chemistry vol 14 no 22 pp7468ndash7475 2006
[81] P-F Tu H-M Shi Z-H Song Y Jiang and Y-Y ZhaoldquoChemical constituents of Cistanche sinensisrdquo Journal of AsianNatural Products Research vol 9 no 1 pp 79ndash84 2007
[82] C-L Si Y-Y Lu P-P Qin R-C Sun and Y-H Ni ldquoPhenolicextractives with chemotaxonomic significance from the bark ofPaulownia tomentosa var tomentosardquo BioResources vol 6 no4 pp 5086ndash5098 2011
[83] J Wu S Zhang Q Xiao et al ldquoPhenylethanoid and aliphaticalcohol glycosides from Acanthus ilicifoliusrdquo Phytochemistryvol 63 no 4 pp 491ndash495 2003
[84] Y Jiang and P-F Tu ldquoAnalysis of chemical constituents inCistanche speciesrdquo Journal of Chromatography A vol 1216 no11 pp 1970ndash1979 2009
[85] H Otsuka H Kuwabara and H Hoshiyama ldquoIdentification ofsucrose diesters of aryldihydronaphthalene-type lignans fromTrigonotis peduncularisand the nature of their fluorescencerdquoJournal of Natural Products vol 71 no 7 pp 1178ndash1181 2008
[86] M-R Suo J-S Yang and Q-H Liu ldquoLignan oligosaccharideesters from Eritrichium rupestrerdquo Journal of Natural Productsvol 69 no 4 pp 682ndash684 2006
[87] P-F Tu Z-H Song H-M Shi Y Jiang and Y-Y ZhaoldquoArylethyl (=phenylethanoid) glycosides and oligosaccharidefrom the stem of Cistanche tubulosardquo Helvetica Chimica Actavol 89 no 5 pp 927ndash935 2006
[88] M-H Shyr T-H Tsai and L-C Lin ldquoRossicasins A Band rosicaside F three new phenylpropanoid glycosides fromBoschniakia rossicardquoChemical and Pharmaceutical Bulletin vol54 no 2 pp 252ndash254 2006
[89] R FangNCVeitchGCKiteM J RHowes EA Porter andM S J Simmonds ldquoGlycosylated constituents of Iris fulvaandIris brevicaulisrdquoChemical amp Pharmaceutical Bulletin vol 59 no1 pp 124ndash128 2011
[90] J Fu L Zuo J Yang R Chen and D Zhang ldquoOligosaccharidepolyester and triterpenoid saponins from the roots of Polygalajaponicardquo Phytochemistry vol 69 no 7 pp 1617ndash1624 2008
[91] M-C Cheng C-Y Li H-C Ko F-N Ko Y-L Lin andT-S Wu ldquoAntidepressant principles of the roots of polygalatenuifoliardquo Journal of Natural Products vol 69 no 9 pp 1305ndash1309 2006
[92] H T Chang and P F Tu ldquoNew oligosaccharide esters andxanthone C-glucosides from Polygala telephioidesrdquo HelveticaChimica Acta vol 90 no 5 pp 944ndash950 2007
[93] J Li L Feng J Dai R Wang and T Nohara ldquoChemical con-stituents from Polygala telephioidesrdquo China Journal of ChineseMateria Medica vol 34 no 4 pp 402ndash405 2009
[94] W-P Yin T-Z Zhao and H-Y Zhang ldquoA novel oligosaccha-ride ester from Syringa pubescensrdquo Journal of Asian NaturalProducts Research vol 10 no 1 pp 95ndash100 2008
[95] M Valko D Leibfritz J Moncol M T D Cronin M Mazurand J Telser ldquoFree radicals and antioxidants in normal physio-logical functions and human diseaserdquoThe International Journalof Biochemistry amp Cell Biology vol 39 no 1 pp 44ndash84 2007
[96] D Krishnaiah R Sarbatly and R Nithyanandam ldquoA review ofthe antioxidant potential of medicinal plant speciesrdquo Food andBioproducts Processing vol 89 no 3 pp 217ndash233 2011
[97] P Liu Y Hu D-H Guo et al ldquoAntioxidant activity ofoligosaccharide ester extracted from Polygala tenuifolia roots insenescence-accelerated micerdquo Pharmaceutical Biology vol 48no 7 pp 828ndash833 2010
[98] Y Hu H-B Liao G Dai-Hong P Liu Y-Y Wang and KRahman ldquoAntidepressant-like effects of 361015840-disinapoyl sucroseon hippocampal neuronal plasticity and neurotrophic signalpathway in chronically mild stressed ratsrdquo NeurochemistryInternational vol 56 no 3 pp 461ndash465 2010
[99] Y Hu H B O Liao P Liu D-H Guo and K RahmanldquoA bioactive compound from Polygala tenuifolia regulatesefficiency of chronic stress on hypothalamic-pituitary-adrenalaxisrdquo Pharmazie vol 64 no 9 pp 605ndash608 2009
[100] A Jungbauer and SMedjakovic ldquoAnti-inflammatory propertiesof culinary herbs and spices that ameliorate the effects ofmetabolic syndromerdquoMaturitas vol 71 no 3 pp 227ndash239 2012
Evidence-Based Complementary and Alternative Medicine 23
[101] Q Xu Y Wang S Guo Z Shen and L Yang ldquoAnti-inflammatory and analgesic activity of aqueous extract of Flospopulirdquo Journal of Ethnopharmacology vol 152 no 3 pp 540ndash545 2014
[102] K S Kim D S Lee G S Bae et al ldquoThe inhibition of JNKMAPK and NF-120581B signaling by tenuifoliside A isolated fromPolygala tenuifolia in lipopolysaccharide-induced macrophagesis associated with its anti-inflammatory effectrdquo European Jour-nal of Pharmacology vol 721 no 1ndash3 pp 267ndash276 2013
[103] J-G Lee J-M Yon C Lin A Y Jung K Y Jung and S-YNamldquoCombined treatment with capsaicin and resveratrol enhancesneuroprotection against glutamate-induced toxicity in mousecerebral cortical neuronsrdquo Food and Chemical Toxicology vol50 no 11 pp 3877ndash3885 2012
[104] M L Jin S Y Park Y H Kim J-I Oh S J Lee andG Park ldquoThe neuroprotective effects of cordycepin inhibitglutamate-induced oxidative andER stress-associated apoptosisin hippocampal HT22 cellsrdquo NeuroToxicology vol 41 pp 102ndash111 2014
[105] P Liu Y Hu J Li et al ldquoProtection of SH-SY5Y neuronal cellsfrom glutamate-induced apoptosis by 36rsquo-disinapoyl sucrosea bioactive compound isolated from radix polygalardquo Journal ofBiomedicine and Biotechnology vol 2012 Article ID 728342 5pages 2012
[106] P-B Li W-L Lin Y-G Wang W Peng X-Y Cai and W-WSu ldquoAntidiabetic activities of oligosaccharides of Ophiopogonisjaponicus in experimental type 2 diabetic ratsrdquo InternationalJournal of Biological Macromolecules vol 51 no 5 pp 749ndash7552012
[107] T Liu Y M Yip L Song et al ldquoInhibiting enzymatic starchdigestion by the phenolic compound diboside A a mechanisticand in silico studyrdquo Food Research International vol 54 no 1pp 595ndash600 2013
[108] F Cote andMGHahn ldquoOligosaccharins structures and signaltransductionrdquo Plant Molecular Biology vol 26 no 5 pp 1379ndash1411 1994
[109] RACreelman and J EMullet ldquoOligosaccharins brassinolidesand jasmonates nontraditional regulators of plant growthdevelopment and gene expressionrdquo Plant Cell vol 9 no 7 pp1211ndash1223 1997
[110] L Jiao D Wan X Zhang B Li H Zhao and S LiuldquoCharacterization and immunostimulating effects on murineperitoneal macrophages of oligosaccharide isolated from Panaxginseng CAMeyerrdquo Journal of Ethnopharmacology vol 144 no3 pp 490ndash496 2012
Submit your manuscripts athttpwwwhindawicom
Stem CellsInternational
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
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Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Behavioural Neurology
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Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
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Disease Markers
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
BioMed Research International
OncologyJournal of
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Oxidative Medicine and Cellular Longevity
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
PPAR Research
The Scientific World JournalHindawi Publishing Corporation httpwwwhindawicom Volume 2014
Immunology ResearchHindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Journal of
ObesityJournal of
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Computational and Mathematical Methods in Medicine
OphthalmologyJournal of
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Diabetes ResearchJournal of
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Research and TreatmentAIDS
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Gastroenterology Research and Practice
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Parkinsonrsquos Disease
Evidence-Based Complementary and Alternative Medicine
Volume 2014Hindawi Publishing Corporationhttpwwwhindawicom
6 Evidence-Based Complementary and Alternative Medicine
18 19
20 21
2
n
OH
OH
H
OH
OH
OH
OH
OO
O
O
O
HO
HOHO
HO
HO
CH2OH
OH
OHO OHO
HO OHO OHO
HO OH
OH
O
OO
HO
HOHO
HO
CH2OH
OH
OHO OHO
HO OHO OHO
HO OH
OH
O
OO
HO
HOHO
OH
OH
OHOHO
HO
OH
OH
OH
OH
OH
OHO
O
O
O
O
O
O
HO
HO
HO
OH
OH
OH
OH O
Figure 1
D benzoyl E p-methoxybenzoyl F p-hydroxybenzoyl G coumaroyl
I feruloyl J caffeoyl K sinapoyl
L 345-trimethoxycinnamoyl M cinnamoyl
O
O
O
O O O
OO
O
OCH3
OCH3
OCH3
OCH3
OCH3
OCH3
OCH3
OH
OHOH
OHOHOH
Figure 2
Evidence-Based Complementary and Alternative Medicine 7
Table2Ph
enylprop
anoid-deriv
eddisaccharid
eeste
rs
Num
ber
Nam
eR 1
R 2R 3
R 4R 5
R 6R 7
R 8Source
Parts
Reference
35Sibiric
oseA
6H
HH
HK
HH
HPolyg
alatricornis
Polyg
alatenu
ifolia
Roots
Root
barks
[37ndash40
]
3631015840-O
-FeruloylsucroseSibiricose
A5
HH
HH
IH
HH
Polyg
alatenu
ifolia
Trillium
kamtsc
haticum
Roots
Und
ergrou
ndparts
[38ndash42]
37GlomeratoseA
HH
HH
LH
HH
Polyg
alatricornis
Roots
[37]
38LapathosideD
HH
HH
GG
HH
Polyg
onum
sachalinense
Stem
s[43]
39Helo
niosideA
HH
HH
II
HH
Trillium
kamtsc
haticum
Smila
xbracteata
Paris
polyphylla
varyunn
anensis
Und
ergrou
ndparts
Aeria
lparts
Roots
[4144
45]
40Helo
niosideB
AcH
HH
II
HH
Smila
xbracteata
Smila
xchina
Smila
xrip
aria
Heterosmila
xerythrantha
Aeria
lparts
Stem
sRo
otsa
ndrhizom
es
[4446
ndash48]
41Paris
polysid
eFH
HH
HG
IH
HPa
risPolyphylla
varyunn
anensis
Rhizom
es[4950]
42Hydropiperosid
eH
HH
HG
GH
GPolyg
onum
sachalinense
Polyg
onum
cuspidatum
Persica
riahydropiper
Stem
sLeaves
[435152]
43Tricorno
seB
DAc
HH
LH
HH
Polyg
alatricornis
Roots
[37]
44Tenu
ifolisideA
FH
HH
LH
HH
Polyg
alatenu
ifolia
Polygalahongkongensis
Polyg
alasib
irica
Roots
Who
leplants
Aeria
lparts
[3840
4253ndash
56]
45Tataris
ideA
AcH
HAc
GG
HAc
Fagopyrum
tataric
umRo
ots
[57]
46Tataris
ideE
HH
HAc
GG
HAc
Fagopyrum
tataric
umRo
ots
[57]
47Tataris
ideG
HH
HH
IG
HG
Fagopyrum
tataric
umRo
ots
[57]
48Sm
iglasid
eAAc
AcH
AcI
IH
ISm
ilaxrip
aria
Rootsa
ndrhizom
es[47]
49Sm
iglasid
eBAc
HH
AcI
IH
ISm
ilaxrip
aria
Rootsa
ndrhizom
es[47]
50Sm
iglasid
eEAc
HH
AcI
IH
GSm
ilaxchina
Stem
s[46]
51Sm
ilasid
eAAc
AcH
HI
IH
HSm
ilaxchina
Stem
s[46]
52Sm
ilasid
eBH
HH
AcI
IH
HSm
ilaxchina
Stem
s[46]
53Sm
ilasid
eCH
HH
HI
IH
GSm
ilaxchina
Stem
s[46]
54Sm
ilasid
eDH
HH
HI
IAc
GSm
ilaxchina
Stem
s[46]
8 Evidence-Based Complementary and Alternative Medicine
Table2Con
tinued
Num
ber
Nam
eR 1
R 2R 3
R 4R 5
R 6R 7
R 8Source
Parts
Reference
55Sm
ilasid
eEAc
HH
HI
IH
GSm
ilaxbracteata
Smila
xchina
Aeria
lparts
Stem
s[4446
]
56Sm
ilasid
eFAc
HH
AcG
IH
GSm
ilaxchina
Stem
s[46]
57Sm
ilasid
eGH
HH
HG
IH
GSm
ilaxbracteata
Smilacis
glabrae
Aeria
lparts
Rhizom
es[4458]
58Sm
ilasid
eHH
HH
AcG
IH
GSm
ilaxbracteata
Aeria
lparts
[44]
59Sm
ilasid
eIAc
HH
HG
IH
GSm
ilaxbracteata
Aeria
lparts
[44]
60Sm
ilasid
eJH
HH
HG
IH
ISm
ilaxbracteata
Smilacis
glabrae
Aeria
lparts
Rhizom
es[4458]
61Sm
ilasid
eKH
HH
AcI
IH
GSm
ilaxbracteata
Aeria
lparts
[44]
62Sm
ilasid
eLH
HH
HI
IH
ISm
ilaxbracteata
Smilacis
glabrae
Aeria
lparts
Rhizom
es[4458]
63Sm
ilasid
eMAc
HH
AcCis-feruloyl
IH
HSm
ilaxrip
aria
Rootsa
ndrhizom
es[59]
64Sm
ilasid
eNAc
HH
AcI
Cis-
feruloyl
HH
Smila
xrip
aria
Rootsa
ndrhizom
es[59]
65Sm
ilasid
ePH
HH
AcI
IH
ISm
ilaxrip
aria
Rootsa
ndrhizom
es[47]
66310158404101584061015840-O
-Tri-
feruloylsucrose
HH
HH
II
IH
Smila
xrip
aria
Rhizom
esand
roots
[60]
6761015840-O
-Cou
maroylsu
crose
HH
HH
HG
HH
Bidens
parviflora
Who
leplants
[61]
6811015840 -O-C
oumaroyl-61015840-O
-feruloylsucrose
HH
HH
HI
HG
Smila
xbracteata
Aeria
lparts
[44]
694-O-Benzoyl-31015840-345-
trim
etho
xycinn
amoylsu
crose
HD
HH
LH
HH
Polyg
alatricornis
Roots
[37]
706-O-Benzoyl-31015840-O
-345-
trim
etho
xycinn
amoylsu
crose
DH
HH
LH
HH
Polyg
alatricornis
Roots
[37]
716-O-Benzoyl-31015840-O
-sin
apoylsu
crose
DH
HH
KH
HH
Polyg
alatricornis
Roots
[37]
726-O-p-M
etho
xybenzoyl-31015840-O
-345-
trim
etho
xycinn
amoylsu
crose
EH
HH
LH
HH
Polyg
alatenu
ifolia
Roots
[56]
7326-Di-a
cetyl-3101584061015840-di-
feruloylsucrose
AcH
HAc
II
HH
Smila
xchina
Smila
xrip
aria
Heterosmila
xerythrantha
Stem
sRo
otsa
ndrhizom
esAe
rialp
arts
[46ndash
4859]
7426-Di-a
cetyl-31015840-O
-cis-feruloy-
61015840-tr
ans-feruloylsucrose
AcH
HAc
Cis-feruloy
IH
HSm
ilaxrip
aria
Rootsa
ndrhizom
es[59]
Evidence-Based Complementary and Alternative Medicine 9
Table2Con
tinued
Num
ber
Nam
eR 1
R 2R 3
R 4R 5
R 6R 7
R 8Source
Parts
Reference
7526-Di-a
cetyl-31015840-O
-tran
s-feruloy-
61015840-cis-feruloylsucrose
AcH
HAc
ICis-
feruloyl
HH
Smila
xrip
aria
Rootsa
ndrhizom
es[59]
76Re
galosid
eAAc
HH
HI
HH
HTrillium
kamtsc
haticum
Und
ergrou
ndparts
[41]
77Tricorno
seA
AcH
HH
LH
HH
Polyg
alatricornis
Roots
[37]
78Mum
eose
AH
HH
AcG
HH
HPrun
usmum
eFlow
erbu
ds[6263]
79Mum
eose
BAc
HAc
HG
HH
HPrun
usmum
eFlow
erbu
ds[6263]
80Mum
eose
CAc
HAc
AcG
HH
HPrun
usmum
eFlow
erbu
ds[6263]
81Mum
eose
DAc
AcAc
AcG
HH
AcPrun
usmum
eFlow
erbu
ds[6263]
82Mum
eose
EAc
AcAc
AcCis-
coum
aroyl
HH
AcPrun
usmum
eFlow
erbu
ds[6263]
83Mum
eose
FAc
AcAc
HG
HH
HPrun
usmum
eFlow
erbu
ds[63]
84Mum
eose
GAc
HAc
HG
HAc
HPrun
usmum
eFlow
erbu
ds[63]
85Mum
eose
HH
HAc
AcG
HAc
HPrun
usmum
eFlow
erbu
ds[63]
86Mum
eose
IAc
AcAc
HG
AcH
HPrun
usmum
eFlow
erbu
ds[63]
87Mum
eose
JAc
AcAc
AcG
HAc
AcPrun
usmum
eFlow
erbu
ds[63 ]
88Mum
eose
KH
HAc
AcG
HH
HPrun
usmum
eFlow
erbu
ds[64]
89Mum
eose
LAc
HAc
AcG
HAc
HPrun
usmum
eFlow
erbu
ds[64]
90Mum
eose
MAc
AcAc
HG
HAc
AcPrun
usmum
eFlow
erbu
ds[64]
91Mum
eose
NAc
AcAc
HG
AcAc
HPrun
usmum
eFlow
erbu
ds[64]
92Mum
eose
OAc
HAc
AcG
HAc
AcPrun
usmum
eFlow
erbu
ds[64]
9311015840 2346-O-Penta-acetyl-31015840-O
-tra
ns-cou
maroylsu
crose
AcAc
AcAc
GH
HAc
Musellalasio
carpa
Aeria
lparts
[65]
9411015840 2346-O-Penta-acetyl-31015840-O
-cis-cou
maroylsu
crose
AcAc
AcAc
Cis-
coum
aroyl
HH
AcMusellalasio
carpa
Aeria
lparts
[65]
9511015840 236-O-Tetra-acetyl-31015840-O
-cis-
feruloylsucrose
AcH
AcAc
Cis-feruloyl
HH
AcSparganium
stolonifer
umRh
izom
es[66]
9611015840 246-O-Tetra-acetyl-31015840-O
-tra
ns-fe
ruloylsucrose
AcAc
HAc
IH
HAc
Sparganium
stolonifer
umRh
izom
es[66]
9711015840 236-O-Tetra-acetyl-31015840-O
-tra
ns-fe
ruloylsucrose
AcH
AcAc
IH
HAc
Sparganium
stolonifer
umRh
izom
es[67]
98Sibirio
sideA
MH
HH
HH
HH
Scrophularianingpoensis
Roots
[68]
99SibricoseA
1K
HH
HH
HH
HCy
nanchu
mam
plexica
ule
Roots
[69]
100
6-O-C
affeoylsucrose
JH
HH
HH
HH
Scrophularianingpoensis
Roots
[68]
101
Acretosid
eI
HH
HH
HH
HScrophularianingpoensis
Roots
[68]
10 Evidence-Based Complementary and Alternative Medicine
Table2Con
tinued
Num
ber
Nam
eR 1
R 2R 3
R 4R 5
R 6R 7
R 8Source
Parts
Reference
102
Tenu
ifolisideB
FH
HH
KH
HH
Polyg
alatenu
ifolia
Roots
[4256]
103
Tenu
ifolisideC
KH
HH
LH
HH
Polyg
alatricornis
Polyg
alatenu
ifolia
Roots
[374256]
104
Heterosmilasid
eH
HI
HH
IH
HHeterosmila
xerythrantha
Aeria
lparts
[48]
105
Quiqu
esetinerviusideA
HI
HH
II
HH
Calamus
quiquesetin
ervius
Stem
s[70]
106
Quiqu
esetinerviusideB
AcI
HH
II
HH
Calamus
quiquesetin
ervius
Stem
s[70]
107
Quiqu
esetinerviusideC
HI
HAc
II
HH
Calamus
quiquesetin
ervius
Stem
s[70]
108
Quiqu
esetinerviusideD
AcG
HH
II
HH
Calamus
quiquesetin
ervius
Stem
s[70]
109
Quiqu
esetinerviusideE
HG
HAc
II
HH
Calamus
quiquesetin
ervius
Stem
s[70]
110
Vanicosid
eAI
HH
AcG
GH
G
Polyg
onum
sachalinensis
Polyg
onum
cuspidatum
Polyg
onum
hydropiper
Stem
sLeaves
Rhizom
es[51527172]
111
Vanicosid
eBI
HH
HG
GH
G
Polyg
onum
sachalinensis
Polyg
onum
cuspidatum
Persica
riahydropiper
Stem
sLeaves
Rhizom
es[4351527172]
112
Vanicosid
eDG
HH
HG
GH
GPersica
riahydropiper
Leaves
[51]
113
Vanicosid
eEI
AcH
AcG
GH
GPolyg
onum
hydropiper
Stem
sand
leaves
[72]
114
LapathosideA
IH
HH
GG
HI
Polyg
onum
sachalinensis
Polyg
onum
cuspidatum
Fagopyrum
dibotrys
Stem
sRh
izom
es[5173]
115
LapathosideC
IH
HH
GG
HH
Polyg
onum
sachalinensis
Polyg
onum
cuspidatum
Stem
s[4352]
116
DibosideA
GH
HH
GI
HG
Fagopyrum
tataric
umFagopyrum
dibotrys
Roots
Rhizom
es[57]
117
Hidropiperosid
eAI
HH
HH
GH
GPolyg
onum
hydropiper
Stem
sand
leaves
[72]
118
Hidropiperosid
eBI
HH
AcG
GH
IPolyg
onum
hydropiper
Stem
sand
leaves
[72]
119
Tataris
ideB
IH
HAc
GG
HAc
Fagopyrum
tataric
umRo
ots
[57]
Evidence-Based Complementary and Alternative Medicine 11
Table2Con
tinued
Num
ber
Nam
eR 1
R 2R 3
R 4R 5
R 6R 7
R 8Source
Parts
Reference
120
Tataris
ideC
IAc
HAc
GG
HAc
Fagopyrum
tataric
umRo
ots
[57]
121
Tataris
ideD
GH
HAc
GI
HH
Fagopyrum
tataric
umRo
ots
[57]
122
Tataris
ideF
GH
HH
II
HG
Fagopyrum
tataric
umRo
ots
[57]
123
310158406-O
-Di-sinapoylsu
crose
KH
HH
KH
HH
Polyg
alatricornis
Polygalahongkongensis
Polyg
alasib
irica
Polyg
alatenu
ifolia
Cynanchu
mam
plexica
ule
Roots
Root
barks
Who
leplants
Aeria
lparts
[37ndash394153ndash
566974]
124
661015840-O
-Di-c
oumaroylsu
crose
GH
HH
HG
HH
Bidens
parviflora
Who
leplants
[61]
125
11015840 3101584061015840-O
-Tri-
coum
aroyl-6
-feruloylsucrose
IH
HH
GG
HG
Fagopyrum
tataric
umRo
ots
[7576]
126
3101584061015840-O
-Di-c
oumaroyl-110158406-O
-di-
feruloylsucrose
IH
HH
GG
HI
Fagopyrum
tataric
umRo
ots
[7576]
127
31015840-O
-Cou
maroyl-11015840610158406-O
-tri-
feruloylsucrose
IH
HH
IG
HI
Fagopyrum
tataric
umRo
ots
[7576]
128
11015840 31015840610158406-O
-Tetra-fe
ruloylsucrose
IH
HH
II
HI
Fagopyrum
tataric
umRo
ots
[7576]
SeeS
chem
e2
12 Evidence-Based Complementary and Alternative Medicine
131130129
CH2OHOH
OH
OO
OH
C
C
HH
HHO
OO
O
HO
HOHO
HO
HOOH
OHOHOH
OHOH
HOO
O
O
O
HO
HO
OH
OHOHOH
OHOH
HOO
O
O
O
HO
Figure 3
12
3
4
5
6
1998400
2998400
3998400
4998400
5998400
6998400
HO
O
O
R1O
R2O
R8O
R7OOR3
OR4 OR5OR6
Scheme 2
antidepressant cytotoxic antineoplastic anti-inflammatoryantidiabetic plant growth-regulatory neuroprotective andcerebral protective activities Lignan-derived disaccharideesters phenylpropanoid-derived tetrasaccharide esters andpentasaccharide esterswith biological activities have not beenreported Aside from the isolated constituents oligosaccha-ride mixtures from Rehmannia glutinosa Panax ginseng andScrophularia ningpoensiswere also reported to display diversepharmacological activities such as antidiabetic immunopo-tentiating enhanced memory and antineoplastic activitiesThese active compounds and mixtures could serve as thevaluable candidates to be developed as possible drugs for thetreatment and prevention of diseases
31 Antioxidant Activity The adverse effects of oxidativestress proposed to play significant roles in the pathogenesis ofcardiovascular diseases atherosclerosis hypertension can-cer diabetes mellitus neurodegenerative diseases rheuma-toid arthritis ischemiareperfusion injury and ageing havebecome an inevitable and serious issue [95 96] Scientistshave thus made great efforts to explore antioxidants frommedicinal plants by using different kinds of assay methodswhich include DPPH radical scavenging assay hydroxylradical scavenging assay superoxide anion scavenging assayand ABTS radical scavenging method [96]
Lapathosides C and D hydropiperoside vanicoside Bhidropiperosides A and B lapathoside A and diboside Awere isolated from the Polygonum Persicaria and Fagopyrumgenera belonging to the Polygonaceae family The DPPH testrevealed that free radical-scavenging activity of the isolatedcompounds termed lapathoside C (115) hydropiperoside(42) vanicoside B (111) and lapathoside D (38) increasedin turn and lapathoside D exhibited strongest scavengingability with an IC
50of 0088 120583M [43] Hidropiperosides A
and B (117 118) were reported to show obvious antioxidantresponse to DPPH radicals with the SC
50values of 234
and 267 120583gmL respectively while vanicoside E moderatelyexhibited the same activity with a SC
50value of 490 120583gmL
[72] Lapathoside A (114) and diboside A (116) just showedlower antioxidant activities with the SC
50values of 19948 and
16552 120583M respectively [73]Smiglasides A and B smilaside P 26-di-acetyl-3101584061015840-
di-feruloylsucrose helonioside B smilasides GndashL and het-erosmilaside were isolated from the Heterosmilax and Smi-lax genera Compared with ascorbic acid (IC
5014352 120583M)
used as positive control smiglasides A and B and smi-laside P (48 49 65) (IC
5033958 33066 and 31449 120583M
resp) showed higher antioxidant activities than 26-di-acetyl-3101584061015840-di-feruloylsucrose (73) and helonioside B (40) (IC
50
63166 and 51827120583M resp) [47] Additionally Nhiem et alreported that helonioside B heterosmilaside (104) and 26-di-acetyl-3101584061015840-di-feruloylsucrose exhibited important DPPHradical scavenging activities with the SC
50values of 91 127
and 87 120583gmL respectively [48] Compared with smilasidesG-I (57ndash59) (ED
50685ndash794120583M) smilasides JndashL (60ndash62)
showed higher radical scavenging activities with an ED50
value of 267ndash327120583M [44]Five quiquesetinerviusides AndashE (105ndash109) isolated from
the Calamus genus showed weak DPPH scavenging activ-ities (IC
50604ndash1018120583M) but exhibited better hydroxyl
radical scavenging activities (IC50
36ndash84 120583M) Moreoverquiquesetinerviuside C showed superoxide anion scaveng-ing activity with an IC
50value of about 1843 120583M [70]
Liu et al investigated the antioxidant capacity of 310158406-O-di-sinapoylsucrose (DISS) (123) by using the acceleratedsenescence-prone short-lived mice (SAMP) in vivo Theanalyses indicated that the activities of antioxidant enzymesof SOD and glutathione peroxidase ascended obviously inSAMP mice when amended with DISS 50mgkg MoreoverDISS could downregulate and even restore the level ofmalondialdehyde in SAMP model group [97]
From the above studies it can be concluded that oligosac-charide esters with antioxidant activities have been identifiedin the Polygonaceae Liliaceae Smilacaceae and Arecaceaefamilies The results of the antioxidant assays show that theincreased number of phenolic hydroxyl groups and acetylgroups could produce higher antioxidant activity Fan etal indicated that the increased number of phenylpropanoidgroups was not beneficial to free radical scavenging activity[43] Zhang et al pointed out that oligosaccharide esters withferuloyl groups exhibited better antioxidant activities thanthose with coumaroyl groups [44]
Evidence-Based Complementary and Alternative Medicine 13
Table 3 Fatty acid-derived disaccharide esters
Number Name R1 R2 Source Parts Reference132 61015840-O-Linoleylsucrose H O Astragalus membranaceus Roots [77]133 61015840-O-Palmitoylsucrose H P Astragalus membranaceus Roots [77]134 6-O-Palmitoylsucrose P H Astragalus membranaceus Roots [77]
135 61015840-O-Linolenoylsucrose H N Astragalus membranaceusEquisetum hiemale
RootsAerial parts [77 78]
136 6-O-Linoleylsucrose O H Astragalus membranaceus Roots [77]137 6-O-Myristoylsucrose Q H Astragalus membranaceus Roots [77]
138 6-O-[(7Z10Z13Z)-Hexadeca-71013-trienoyl]sucrose H R Equisetum hiemale Aerial parts [78]
139 6-O-[(7Z10Z)-Hexadeca-710-dienoyl]sucrose H S Equisetum hiemale Aerial parts [78]
See Scheme 3
12
3
4
5
6
1998400
2998400
3998400
4998400
5998400
6998400
HO
O
O
R1O
R2O
R8O
R7OOR3
OR4 OR5OR6
O
O
O
18
18
1616
16
14
N linolenoyl
O linoleyl
P palmitoyl
Q myristoyl
O
O
O
R hexadeca-71013-trienoyl
S hexadeca-710-dienoyl
Scheme 3
32 Antidepressant Activity The oligosaccharides obtainedfrom the Morinda genus not only show specific antidepres-sant and antistress activities but also have no suppression orexcitatory effects on central nervous system as well Whatis more they can be taken orally with little toxicity [21]The inulin-type hexasaccharide (IHS) (9) from Morindaofficinalis obviously exhibited cytoprotective activity whichcontributed to the antidepressant effect not only by providingthe PC12 with protection against Cort-induced lesion withIHS 0625 and 125 120583Mbut also by reducing theCort-induced[Ca2+]
119894overloading with IHS 25 and 10 120583M IHS 5 and
10 120583Mupregulated the nerve growth factormRNAexpressionin Cort-induced PC12 cells [22] Polygalatenosides A (181)and B (182) were isolated from the Polygala genus Theysignificantly inhibited the isotope-labeled RTI-55 binding to
norepinephrine transporter protein with the IC50
values of300 and 604 120583M respectively [91]
DISS and tenuifoliside A were isolated from the PolygalaandCynanchum genera Liu et al investigated the antidepres-sant effect of YZ ethanol extract based on the tail suspensiontest (TST) and forced swimming test (FST) which arethe ease-of-use and widely-accepted models for estimatingantidepressant activities in mice The results indicated thatYZ-50 fraction at a dose of 200mgkgwas able to significantlydecrease the immobility time in TST Furthermore YZ-50possessed ability to inhibit corticosterone-induced injury ofhuman neuroblastoma SH-SY5Y cells What is more DISS(123) and tenuifoliside A (44) two major compounds of YZ-50 fraction showed effective protective response to the lesionin SY5Y cells [53] The antidepressant-like effect of DISS at
14 Evidence-Based Complementary and Alternative Medicine
H3CO
HO
HOHO
HO
HO
HO
HOHO
O O
OO O
OO
O
O
O
OO
O
O
OH
OH
OH
OH
OCH3
OCH3
CH2OH
CH2OH
CH2OAc
CH2OAc
H3CO
HOHO
HO
O
O
O
OO
O
O
OH
OH
OH
OCH3
CH2OH
CH2OH
H3CO
H3CO H3CO
HOHO
HO
O
O
O
OO
O
O
OH
OH
OH
OCH3
CH2OH
CH2OAc
CH3O
H
HOHO
HO
HO
HOO O
OO O
OO
OH
OCH3
CH2OHCH2OH
H3CO H3CO
H
CH2CH2 HO
HO
HO
HO
HOO O
OO O
OO
OH
OCH3
CH2OHCH2OAc
H3CO
H
CH2
140 141 142
143 144 145
Figure 4
Table 4 Phenylpropanoid-derived trisaccharide esters
Number Name R1 R2 R3 R4 R5 R6 R7 Source Parts Reference146 Tricornose C K H H H H L H Polygala tricornis Roots [37]147 Tricornose D K H H H H K H Polygala tricornis Roots [37]148 Tricornose E K H H H K L H Polygala tricornis Roots [37]149 Tricornose F K H H H I L H Polygala tricornis Roots [37]See Scheme 4
O
OOO
O
R2O
R4O
R3O
R6O
OH
OH
OH
OH
OR1
OR5CH2OR7
Scheme 4
the doses of 5 10 and 20mgkg was also tested in chronicallymild stressed rats DISS was able to exhibit antidepressantactivity by upregulating the expression of noradrenergic-regulated plasticity genes including cell adhesion moleculeL1 brain-derived neurotrophic factor laminin and cAMP
response element binding protein factor in hippocampus[98] DISS improved the reward reaction by increasingsucrose intake and obviously decreased the levels of serumcortisol adrenocorticotrophic hormone and corticotropin-releasing factor Further DISS played an enhanced role inthe expression of mineralocorticoid receptor together withglucocorticoid receptor mRNA [99]
33 Cytotoxic and Antineoplastic Activities Smilasides AndashFand P smiglasides A and B smilaside P and helonioside Awere isolated from the Smilax Trillium and Paris generaKuo et al obtained smilasides AndashF (51ndash56) and evaluatedtheir cytotoxicity against human tumor cell lines comprisinghuman oral epithelium carcinoma (KB) human cervicalcarcinoma (Hela) human colon tumor (DLD-1) humanbreast adenocarcinoma (MCF-7) human lung carcinoma (A-549) and humanmedulloblastoma (Med) cells byMTTassayExperimental data indicated that all but smilaside C showedcytotoxicity against three to six human tumor cell lines(ED50
= 51ndash130 120583gmL) and smilasides DndashF (ED50
= 27ndash50 120583gmL) displayed strong cytotoxic activities against DLD-1 cells [46]Wang et al reported the antitumor constituents of
Evidence-Based Complementary and Alternative Medicine 15
OH
OH
OH
OH
OH
OHOH
OHOH
OHOH
OH
OHOHOH
OH
OH
OH
OHOH
OH
OH
OHOH
H
H H
HO
O
O
O
O
O
O
O
OO
OO
O
OO
O
HO
HO
HO
OO
O
O
OO
OO
O
OO
O
OO
O
OO
O
O
O
OO
O
O
OO
O
OO
OOOO
HO
HO
HO
HO
HO
HO
HO
HO
HO
HO
HOHO
HO
HO
HO
HO
HO
150 151 152
153 180
AcO
AcO
AcOAcO
OAc
OAc
CH2OH
OHOH
OH OHOH
OHOH
OH
OHOH
CH3O
Figure 5
Table 5 Phenylpropanoid-derived tetrasaccharide esters
Number Name R1 R2 R3 Source Parts Reference154 Tricornose G K H K Polygala tricornis Roots [37]155 Tricornose H K K K Polygala tricornis Roots [37]156 Tricornose I K K L Polygala tricornis Roots [37]157 Tricornose J K I L Polygala tricornis Roots [37]158 Tricornose K K I K Polygala tricornis Roots [37]159 Tricornose L K G K Polygala tricornis Roots [37]See Scheme 5
Smilax riparia including smiglasides A (48) and B (49) 26-di-acetyl-3101584061015840-di-feruloylsucrose (73) helonioside B (40)and smilaside P (65) Only smiglasidesA andB and smilasideP exhibited cytotoxicity against human tumor cell lines withdifferent inhibitory concentrations comparing with cisplatinand paclitaxel as positive controls [47] Helonioside A (39)exhibited higher cytotoxicity with the increase of concentra-tion (01ndash100120583gmL) [45] Tatarisides AndashG (45 119ndash121 46122 47) and diboside A (116) from the Fagopyrum genusexerted cytotoxic activities against different human cell linesand the cytotoxicity of tatariside C was the most remarkablewith the IC
50values ranging from 644 to 749 120583gmL [57]
11015840236-O-Tetra-acetyl-31015840-O-cis-feruloylsucrose (95) fromthe Sparganium plants exhibited extremely weak cyto-toxicity against the growth of mice Lung Adenocarcinoma
795 cell lines with an IC50
value of 116 120583gmL [66] SnS-2oligosaccharides mixture including raffinose (3) stachyose(19) and verbascose (21) from the roots of Scrophularianingpoensis had antitumor activity against the growth ofLewis pulmonary carcinoma cells transplanted into mice[18]
Disaccharide esters and oligosaccharides mixture fromthe Liliaceae Polygonaceae Sparganiaceae and Scrpophular-iaceae families showed effective cytotoxic and antineoplasticactivities The study results indicated that feruloyl and acetylgroups play an important role in mediating cytotoxicitywhich seems to be related to the substitution position offeruloyl groups The feruloyl groups at C-6 or C-11015840 are vitalfor cytotoxicity In addition the increased number of acetylgroups could induce higher tumoricidal activity
16 Evidence-Based Complementary and Alternative Medicine
Table 6 Phenylpropanoid-derived pentasaccharide esters
Number Name R1 R2 R3 R4 R5 R6 Source Parts Reference160 Tenuifoliose A G D I Ac Ac Ac Polygala tenuifolia Roots [38 42]161 Tenuifoliose B G D I H Ac Ac Polygala tenuifolia Roots [42]162 Tenuifoliose C G D I H H H Polygala tenuifolia Roots [42]163 Tenuifoliose F G D U Ac Ac Ac Polygala tenuifolia Roots [42]164 Tenuifoliose G G D U Ac H Ac Polygala tenuifolia Roots [42]165 Tenuifoliose H G D G Ac Ac Ac Polygala tenuifolia Roots [38 42 79]166 Tenuifoliose I G D G Ac H Ac Polygala tenuifolia Roots [42 79]167 Tenuifoliose J G D G H Ac Ac Polygala tenuifolia Roots [42]168 Tenuifoliose K G D G H H Ac Polygala tenuifolia Roots [42]169 Tenuifoliose L G D T Ac Ac Ac Polygala tenuifolia Roots [42 79]170 Tenuifoliose M G D T Ac H Ac Polygala tenuifolia Roots [42]171 Tenuifoliose N I D I Ac Ac Ac Polygala tenuifolia Roots [42]172 Tenuifoliose O I D I H Ac Ac Polygala tenuifolia Roots [42]173 Tenuifoliose P I D I H H Ac Polygala tenuifolia Roots [42]174 Tenuifoliose Q G D T H Ac Ac Polygala tenuifolia Roots [79]175 Tenuifoliose S G D G H H H Polygala tenuifolia Roots [42]176 Tenuifoliose T G D I H H H Polygala tenuifolia Roots [42]177 Tenuifoliose V H D I Ac Ac Ac Polygala tenuifolia Roots [42]178 Tenuifoliose W I D U Ac H Ac Polygala tenuifolia Roots [42]179 Tenuifoliose X I D I H H H Polygala tenuifolia Roots [42]See Scheme 6
O
OO
O
O
O
O
OR1
OH
OH
OH
OHOH
OH
HOHO
HO
HO
OR2
R3O
CH2OH
Scheme 5
34 Anti-Inflammatory Activity Inflammation an importantbasic pathological process is a defense response of biopsywith vascular system to damage stimuli such as pathogensimpaired cells and tissues and physical and chemical factorsHowever if the process of inflammatory response cannot endnormally when cell debris and pathogens were cleared thebiological defence response will become causative factor andbring about many diseases such as diabetes cardiovasculardiseases metabolic syndrome and cancer [100 101]
Tenuifoliside A (44) from the Polygala genus exhibitedstrong anti-inflammatory effect not only by suppressing the
production of NO but also by reducing the production ofiNOS prostaglandin E2 cyclooxygenase-2 and proinflam-matory cytokines through the inhibition of the mitogen-activated protein kinases pathway and NF-120581B pathway [102]The anti-inflammatory activities of quiquesetinerviusides D(108) and E (109) from the Calamus genus were evaluated inRAW 2647 cells Both of them showed significant inhibitoryeffects against the production of LPS-stimulated NOwith theIC50values of 90ndash295120583M [70]Six disaccharide fatty acid esters (132ndash137) were iso-
lated from the Astragalus and Equisetum genera The anti-inflammatory effects of these isolated compounds have alsobeen documented The activation of NF-120581B could upregulatethe expression of proinflammatory cytokines inducible nitricoxide synthase (iNOS) and tumornecrosis factor alpha (TNF-120572) The NF-120581B inhibitory activities of compounds 132ndash137were tested in HepG2 cells stimulated with TNF-120572 All ofthese compounds could significantly restrainTNF-120572-inducedNF-120581B transcriptional activities with the IC
50values of 44ndash
247 120583M Li et al pointed out that olefinic bonds and thelength of the fatty acid moieties contributed to the NF-120581B inhibitory activity Furthermore the inhibition increasedsignificantly with the increase of the number of olefinic bondson the aliphatic moiety [77] These results may provide ascientific basis for the development of new anti-inflammatoryagents
35 Neuroprotective and Cerebral Protective Activities Aswe all know glutamate works as a major excitatory aminoacid neurotransmitter in the mammalian central nervous
Evidence-Based Complementary and Alternative Medicine 17
R6O
R2O
OR3
OR5
OR4
CH2OR1
OCH3
Rham
OO
O
OO O
O
O
O
OO
RhamO
O
OH
OH
OHOH
OH
OHOH
OHHO
HO
HO
T O-rhamnosyl-coumaroyl U O-rhamnosyl-feruloyl
Scheme 6
system and plays a crucial role in several physiological pro-cesses [103] However the accumulation of glutamate inducesdiverse acute and chronic neurodegenerative diseases suchas epilepsy ischemic stroke and Parkinsonrsquos disease aswell as Alzheimerrsquos disease [104] DISS (123) isolated fromthe Polygala genus exhibited neuroprotective effect againstglutamate-induced SH-SY5Y neuronal cell damage The invitro test demonstrated that DISS (06 6 and 60 120583molL)played a critical role in increasing cell viability controllinglactate dehydrogenase and attenuated apoptosis ranging from195 to 258 [105]
Tenuifoliside B (102) from the Polygala genus was ableto significantly shorten the coma time of KCN-inducedanoxia mice at the doses of 3 and 10mgkg and it playedan important role in ameliorating the scopolamine-inducedimpairment of performance in passive avoidance task inrats and enhancing the tremors induced by oxotremorine inmiceThese results together demonstrated that tenuifoliside Bpossessed cognitive improving and cerebral protective effects[56]
36 Antidiabetic Activity Diabetes mellitus a chronic debil-itating metabolic disease is characterized by high bloodglucose content and comprises three types termed type Itype II and gestational diabetes [106] Stachyose (19) extract(a part) from Rehmannia glutinosa obviously exhibited theactivity of downregulating fasting plasma glucose level andpartially keeping from hyperglycemia induced by adrenalineand glucose without obvious dose-dependent effect Otherthan that in vivo tests in rats induced by alloxan revealed
that stachyose extract at the dose of 200mgkg significantlydecreased blood-sugar level [15]
Diboside A lapathosides C and D vanicosides A andB and hydropiperoside were isolated from the FagopyrumPolygonum and Persicaria genera belonging to the Polygo-naceae family Diboside A (116) could potentially inhibit 120572-amylase activity with an IC
50of 269 120583M and thus retard the
starch digestion rate which is helpful for diabetic individualsin controlling blood sugar level [107] Lapathoside D (38)exerted stronger activity of 120572-glucosidase inhibition with anIC50
value of 0113mM than acarbose which was chosen asa positive drug for the treatment of type II diabetes [43]Vanicoside B (111) was reported to have higher 120573-glucosidaseinhibitory activity with an IC
50of 505 120583M than vanicoside A
(110) with an IC50of 599 120583M because of the acetyl moiety of
the latter possibly decreasing inhibitory activity of vanicosideA [71]
Fujimoto et al investigated the inhibitory effects ofmumeoses FndashO (83ndash92) from the Prunus genus on aldosereductase and discovered that caffeoyl groups are crucialfor the inhibitory effect on aldose reductase And thusmumeoses F G H J K L M and N (IC
50= 22ndash77120583M) with
a coumaroyl group and acetyl groups inhibited moderatelyaldose reductase from reducing glucose to sorbitol whichis associated with the chronic complications of diabetes [6364]
37 Elicitors and Regulators Oligosaccharides are quitepropitious for encoding biological information because ofdiverse monosaccharide units and complex molecular struc-tures and they are therefore first described as biological
18 Evidence-Based Complementary and Alternative Medicine
181 H
H
H
H
H
H
H
H
H H
H
H
H
H
H
H
H H
HH
Benzyl
Benzyl
Benzyl
182
183
184 Ac
Ac
Ac
Ac
Ac
Ac
Ac
Ac
Ac
Ac
185
186
187
188
189
R1 R2 R3
R1 R2 R3 R4
OCH3
R3OH2C OR2
OR1
OR1
O
O
O
O O
OOO
O
OO
O
OH
OH
OH OH
OH
O O
O
O
OH
HO
OH
OH OHOH
OH
OH
OHHO
HO
OH
OH
HO
CH2OH
CH2OH
CH2OH
CH2OH
C
R2O
R3O
CH2OR4
CH2CH2 CH2CH2CH2CH2CH3
CH3
CH3
191190 192
193
O
C C
O
OO
OO
OO
OO
O O
O
O
O
O
O
O
OH
OH
OHHO
HO
HOOH
OH
OH
OH
HO
OH
OH
OH
OH
HO
HO
C C
R998400O
R998400
Figure 6
signals in plants [108] Oligosaccharides from the cell wallfragments of plants and fungi are powerful signal moleculessuch as the elicitors of plant defence response and theregulators of plant growth and they are capable of exertingbiological activities at exceedingly low concentrations [109]Heptasaccharide (HS) (15) and octasaccharide (OS) (16) iso-lated from the Paris genus possessed plant growth-regulatory
activities [29 30]The two oligosaccharides significantly pro-moted the proliferation of Paris polyphylla var yunnanensisroots at the doses of 25ndash20mgL The octasaccharide hadthe most obvious effect on the growth of Panax japonicusvar major hairy roots at a dose of 30mgL while the otherhad the most positive effect on saponin accumulation ofPanax japonicus var major hairy roots at a dose of 10mgL
Evidence-Based Complementary and Alternative Medicine 19
[29] Similarly Zhou et al evaluated the stimulating effectsof HS and OS on the root growth and saponin productionof Panax ginseng hairy roots which were induced from theplant roots infected withAgrobacterium rhizogenes strain A4The results showed that there was a maximum effect on thehairy roots growth and saponin accumulation on day 10Compared with control group the root biomass dry weightwas increased by more than 17-fold while the total saponincontent of roots increased by more than 1-fold when thesetwo oligosaccharides were added to the hairy root at a dose of30mgL [30] The above data illustrate that HS and OS couldserve as the plant growth-regulators not only in their originalspecies but also in others
38 Immunopotentiating Activity Macrophages are impor-tant targets of investigations on cytophagy cellular immunityand molecular immunology Therefore they are deemedto play a vital role in host defense comprising phagocy-tosis proteolytic processing pathogenic agent apoptosiscytokines production and foreign antigens presentation[110] The water-extracted oligosaccharides from Panax gin-seng (WGOS) exhibited better immunopotentiating activ-ity by increasing phagocytic function of macrophages andpromoting NO TNF-120572 and reactive oxygen species pro-duction [110] In addition Wan et al have obtained malto-oligosaccharides (17 119899 = 3sim8) and three oligosaccharides (213 14) from the Panax ginseng roots The in vitro bioassaypointed out thatWGOS could serve as efficacious stimulatorsof B and T lymphocytes [28] These studies provided enlight-enment that the mixture of oligosaccharides from Chineseherbalmedicine exhibits significant effect on immune system
39 Others Acetylcholinesterase (AChE) inhibitors showgood therapeutic effects onmyasthenia gravis glaucoma andAlzheimerrsquos disease through reversible enzyme inhibitionso as to increase the accumulation of acetylcholine in thesynapse and then promote and prolong the function ofacetylcholine Vanicoside B (111) showed AChE inhibitoryactivity with an IC
50of 0062mM while hydropiperoside
(42) and lapathosides C (115) and D (38) just exhibited weakenzyme inhibitory activity [43]
Wang et al has explored low molecular mass carbohy-drate polymer from Panax ginseng roots and obtained 30ethanol elution (PGO)which included peptides and oligosac-charides (17 119899 = 0sim5) identified as maltose maltotriosemaltotetraose maltopentaose maltohexaose and maltohep-taose Pharmacological experiments revealed that PGO couldsignificantly enhance the memory in scopolamine-inducedmemory deficit rats [27]
Cistanoside F (129) and kankanose (150) were isolatedfrom the Cistanche Paulownia and Acanthus genera Phar-macological experiments showed that cistanoside F andkankanose significantly exhibited vasorelaxant effects on thenoradrenaline-induced contraction of thoracic aorta fromrats [80]
4 Conclusion
Traditional Chinese medicine from natural kingdom playsan indelible role in the treatment of human diseases andit has aroused the attention of those who have engagedin medicinal pharmaceutical chemistry Therefore scientistshave made great contributions day after day to investigate thevalid chemicals from traditional Chinese medicines In thepast decades about 193 oligosaccharides and their esters havebeen identified from traditional Chinese medicinal plantsOn the one hand only a few oligosaccharides and theirmixtures were investigated and just exhibited antidepres-sant antineoplastic antidiabetic plant growth-regulatoryimmunopotentiating and enhancedmemory activitiesMoreexploratory work is still needed to excavate biological andpharmacological activities of oligosaccharides On the otherhand oligosaccharide esters exhibited multi-advantageousactivities Bioassays have revealed that antioxidant cytotoxicantineoplastic and anti-inflammatory activities are the mostnotable bioactivities Of course to search for the naturalproducts with these activities is a hotpot in the contemporarydrug research Oligosaccharide esters provide a vast treasuretrove for medical researchers After considering the currentstudies it should be taken as future directions to makemore mechanism of action studies and clinical trials tofurther evaluate its potential as new drugs Moreover thestructure-activity relationships discussed in this review willprovide reference information for further exploring theirrelationships and continually discovering the new bioactiveoligosaccharide esters
Conflict of Interests
The authors declare that there is no conflict of interestsregarding the publication of this paper
References
[1] X D Yang L J Zhang B Liang L Z Xu and S L YangldquoOligosaccharide esters isolated from plants of PolygalaceaerdquoChinese Traditional and Herbal Drugs vol 33 no 10 pp 954ndash958 2002
[2] N Ogwuru and M Adamczeski ldquoBioactive natural productsderived from Polygonum species of plants their structures andmechanisms of actionrdquo Studies in Natural Products Chemistryvol 22 pp 607ndash642 2000
[3] S Kobayashi T Miyase and H Noguchi ldquoPolyphenolic glyco-sides and oligosaccharide multiesters from the roots of Polygaladalmaisianardquo Journal of Natural Products vol 65 no 3 pp 319ndash328 2002
[4] M Takasaki S Kuroki M Kozuka and T Konoshima ldquoNewphenylpropanoid esters of sucrose from Polygonum lapathi-foliumrdquo Journal of Natural Products vol 64 no 10 pp 1305ndash1308 2001
[5] M L Zimmermann and A T Sneden ldquoVanicosides A and Bprotein kinase C inhibitors from Polygonum pensylvanicumrdquoJournal of Natural Products vol 57 no 2 pp 236ndash242 1994
[6] M Takasaki T Konoshima S Kuroki H Tokuda and HNishino ldquoCancer chemopreventive activity of phenylpropanoid
20 Evidence-Based Complementary and Alternative Medicine
esters of sucrose vanicoside B and lapathoside A from Poly-gonum lapathifoliumrdquo Cancer Letters vol 173 no 2 pp 133ndash138 2001
[7] Q Fu T Liang Z Y Li et al ldquoSeparation of carbohydrates usinghydrophilic interaction liquid chromatographyrdquo CarbohydrateResearch vol 379 pp 13ndash17 2013
[8] M F Mrozek D Zhang and D Ben-Amotz ldquoOligosaccharideidentification and mixture quantification using Raman spec-troscopy and chemometric analysisrdquo Carbohydrate Researchvol 339 no 1 pp 141ndash145 2004
[9] G S Armstrong and B Bendiak ldquoHigh-resolution four-dimen-sional carbon-correlated 1H-1H ROESY experiments employ-ing isotags and the filter diagonalization method for effectiveassignment of glycosidic linkages in oligosaccharidesrdquo Journalof Magnetic Resonance vol 181 no 1 pp 79ndash88 2006
[10] G S Armstrong V A Mandelshtam A J Shaka and BBendiak ldquoRapid high-resolution four-dimensional NMR spec-troscopy using the filter diagonalization method and its advan-tages for detailed structural elucidation of oligosaccharidesrdquoJournal of Magnetic Resonance vol 173 no 1 pp 160ndash168 2005
[11] H-M Tseng S Gattolin J Pritchard H J Newbury and DA Barrett ldquoAnalysis of mono- di- and oligosaccharides by CEusing a two-stage derivatization method and LIF detectionrdquoElectrophoresis vol 30 no 8 pp 1399ndash1405 2009
[12] N Li X Li B L Hou and D L Meng ldquoNew disaccharosidefrom Camptosorus sibiricus Ruprrdquo Natural Product Researchvol 22 no 15 pp 1379ndash1383 2008
[13] Z Zhang D Wang Y Zhao H Gao Y-H Hu and J-FHu ldquoFructose-derived carbohydrates from Alisma orientalisrdquoNatural Product Research vol 23 no 11 pp 1013ndash1020 2009
[14] X Yang Y Zhao N He and K D Croft ldquoIsolation char-acterization and immunological effects of 120572-galacto-oligo-saccharides from a new source the herb Lycopus lucidus TurczrdquoJournal of Agricultural and Food Chemistry vol 58 no 14 pp8253ndash8258 2010
[15] R X Zhang Z P Jia L Y Kong et al ldquoStachyose extractfrom Rehmannia glutinosa Libosch to lower plasma glucose innormal and diabetic rats by oral administrationrdquo Pharmazievol 59 no 7 pp 552ndash556 2004
[16] R Zhang Y Zhao Y Sun X Lu and X Yang ldquoIsolationcharacterization and hepatoprotective effects of the raffinosefamily oligosaccharides from Rehmannia glutinosa liboschrdquoJournal of Agricultural and Food Chemistry vol 61 no 32 pp7786ndash7793 2013
[17] H Li F Song Z Zheng Z Liu and S Liu ldquoCharacterization ofsaccharides and phenolic acids in the Chinese herb Tanshen byESI-FT-ICR-MS and HPLCrdquo Journal of Mass Spectrometry vol43 no 11 pp 1545ndash1552 2008
[18] J E Deng J Zhang XM ChenW Ke and G Y Tian ldquoStudieson the physicochemical properties structure and antitumoractivity of an oligosaccharide homologue SnS-2 from the root ofScrophularia ningpoensis Hemslrdquo Chinese Journal of Chemistryvol 22 no 5 pp 492ndash497 2004
[19] S C Chou LM Chuang and S S Lee ldquoHypoglycemic constit-uents of gynura divaricata subsp formosanardquo Natural ProductCommunications vol 7 no 2 pp 221ndash222 2012
[20] F Feng L-L Wang X-P Lai Y-B Li Z-M Cao and Y-J Zhou ldquoStudy on oligosaccharides from Morinda officinalisrdquoJournal of Chinese Medicinal Materials vol 35 no 8 pp 1259ndash1262 2012
[21] Y F Li Z H Gong M Yang Y M Zhao and Z P Luo ldquoInhibi-tion of the oligosaccharides extracted fromMorinda officinalis
a Chinese traditional herbal medicine on the corticosteroneinduced apoptosis in PC12 cellsrdquo Life Sciences vol 72 no 8 pp933ndash942 2003
[22] Y-F Li Y-Q Liu M Yang et al ldquoThe cytoprotective effect ofinulin-type hexasaccharide extracted from Morinda officinalison PC12 cells against the lesion induced by corticosteronerdquo LifeSciences vol 75 no 13 pp 1531ndash1538 2004
[23] D N Olennikov L M Tankhaeva and A V Rokhin ldquoGlu-cofructans from Saussurea lappa rootsrdquo Chemistry of NaturalCompounds vol 47 no 3 pp 339ndash342 2011
[24] S K Hyun H A Jung B S Min J H Jung and J S ChoildquoIsolation of phenolics nucleosides saccharides and an alkaloidfrom the root of Aralia cordatardquo Natural Product Sciences vol16 no 1 pp 20ndash25 2010
[25] Z J Xu C W Lin and M F Liao ldquoStructure analysis of a newoligosaccharides BROS from Blumea ripariardquo Chinese Journalof Organic Chemistry vol 31 no 11 pp 1811ndash1819 2011
[26] Z J Xu C W Lin and Y Shi ldquoIsolation and structuredetermination of a new oligosaccharide from Blume ripariardquoJournal of Medicinal Plants Research vol 5 no 14 pp 2956ndash2962 2011
[27] Y Wang R Z Jiang G R Li et al ldquoStructural and enhancedmemory activity studies of extracts from Panax ginseng rootrdquoFood Chemistry vol 119 no 3 pp 969ndash973 2010
[28] DWan L Jiao H Yang and S Liu ldquoStructural characterizationand immunological activities of the water-soluble oligosaccha-rides isolated from thePanax ginseng rootsrdquoPlanta vol 235 no6 pp 1289ndash1297 2012
[29] L G Zhou C Z Yang J Q Li S L Wang and J Y WuldquoHeptasaccharide and octasaccharide isolated from Paris pol-yphylla var yunnanensis and their plant growth-regulatoryactivityrdquo Plant Science vol 165 no 3 pp 571ndash575 2003
[30] L G Zhou X D Cao R F Zhang Y L Peng S J Zhao andJ Y Wu ldquoStimulation of saponin production in Panax ginsenghairy roots by two oligosaccharides from Paris polyphylla varyunnanensisrdquo Biotechnology Letters vol 29 no 4 pp 631ndash6342007
[31] M Vanhaecke W van den Ende E Lescrinier and N Dyu-bankova ldquoIsolation and characterization of a pentasaccharidefrom Stellaria mediardquo Journal of Natural Products vol 71 no 11pp 1833ndash1836 2008
[32] J Feng and W Zhao ldquoComplete 1Hand 13C NMR assignmentsof four new oligosaccharides and two new glycosides fromPeriploca forrestiirdquoMagnetic Resonance in Chemistry vol 47 no8 pp 701ndash705 2009
[33] J Q Feng R J Zhang Y Zhou et al ldquoImmunosuppressive preg-nane glycosides from Periploca sepium and Periploca forrestiirdquoPhytochemistry vol 69 no 15 pp 2716ndash2723 2008
[34] X H Long R Xu Y H Zhang X H Tan andQ Y Sun ldquoA newoligosaccharide from Periploca calophyllardquo Zhongguo ZhongyaoZazhi vol 37 no 2 pp 226ndash229 2012
[35] L Wang Z-Q Yin Y Wang X-Q Zhang Y-L Li and W-CYe ldquoPerisesaccharides A-E new oligosaccharides from the rootbarks ofPeriploca sepiumrdquoPlantaMedica vol 76 no 9 pp 909ndash915 2010
[36] T Lei L Zhang H-Y Jiang Y Hu A-H Hong and Y-Z CenldquoA new pregnane glycoside and oligosaccharide from Parabar-ium huaitingiirdquo Journal of Asian Natural Products Research vol13 no 11 pp 1030ndash1035 2011
[37] J Li Y Jiang and P F Tu ldquoTricornoses A-L oligosaccharidemulti-esters from the roots of Polygala tricornisrdquo Journal ofNatural Products vol 68 no 5 pp 739ndash744 2005
Evidence-Based Complementary and Alternative Medicine 21
[38] H H Tu P Liu L Mu et al ldquoStudy on antidepressant com-ponents of sucrose ester from Polygala tenuifoliardquo ZhongguoZhongyao Zazhi vol 33 no 11 pp 1278ndash1280 2008
[39] G M She Y Y Ba Y Liu H Lv W Wang and R B ShildquoAbsorbable phenylpropenoyl sucroses from Polygala tenuifo-liardquoMolecules vol 16 no 7 pp 5507ndash5513 2011
[40] J Yong and P F Tu ldquoStudies on the chemical constituents inroot bark of Polygala tenuifolia (II)rdquo China Journal of ChineseMateria Medica vol 29 no 8 pp 751ndash753 2004
[41] M Ono C Takamura F Sugita et al ldquoTwo new steroidglycosides and a new sesquiterpenoid glycoside from theunderground parts of Trillium kamtschaticumrdquo Chemical andPharmaceutical Bulletin vol 55 no 4 pp 551ndash556 2007
[42] Y Ling Z Li M Chen Z Sun M Fan and C HuangldquoAnalysis and detection of the chemical constituents of RadixPolygalae and their metabolites in rats after oral administrationby ultra high-performance liquid chromatography coupledwith electrospray ionization quadrupole time-of-flight tandemmass spectrometryrdquo Journal of Pharmaceutical and BiomedicalAnalysis vol 85 pp 1ndash13 2013
[43] P Fan L Terrier A-E Hay A Marston and K HostettmannldquoAntioxidant and enzyme inhibition activities and chemicalprofiles ofPolygonum sachalinensis FSchmidt exMaxim (Polyg-onaceae)rdquo Fitoterapia vol 81 no 2 pp 124ndash131 2010
[44] L J Zhang C C Liao H C Huang Y C Shen L M Yangand Y H Kuo ldquoAntioxidant phenylpropanoid glycosides fromSmilax bracteatardquo Phytochemistry vol 69 no 6 pp 1398ndash14042008
[45] L L Yan W Y Gao Y J Zhang and Y Wang ldquoA new phenyl-propanoid glycosides from Paris polyphylla var yunnanensisrdquoFitoterapia vol 79 no 4 pp 306ndash307 2008
[46] Y H Kuo Y W Hsu C C Liaw J K Lee H C Huang andL M Y Kuo ldquoCytotoxic phenylpropanoid glycosides from thestems of Smilax chinardquo Journal of Natural Products vol 68 no10 pp 1475ndash1478 2005
[47] W-X Wang T-X Li H Ma J-F Zhang and A-Q JialdquoTumoral cytotoxic and antioxidative phenylpropanoid glyco-sides in Smilax riparia A DCrdquo Journal of Ethnopharmacologyvol 149 no 2 pp 527ndash532 2013
[48] N X Nhiem P vanKiem C vanMinh et al ldquoPhenylpropanoidglycosides fromHeterosmilax erythrantha and their antioxidantactivityrdquo Archives of Pharmacal Research vol 32 no 10 pp1373ndash1377 2009
[49] Y Wang W Y Gao T J Zhang and Y Q Guo ldquoA novelphenylpropanoid glycosides and a new derivation of phenolicglycoside from Paris Polyphylla var yunnanensisrdquo ChineseChemical Letters vol 18 no 5 pp 548ndash550 2007
[50] J-Y Zhang Y-Z Wang Y-L Zhao et al ldquoPhytochemicals andbioactivities of Paris speciesrdquo Journal of Asian Natural ProductsResearch vol 13 no 7 pp 670ndash681 2011
[51] N H N Hashim F Abas K Shaari and N H Lajis ldquoLC-DAD-ESIMSMS characterization of antioxidant and anti-cholinesterase constituents present in the active fraction fromPersicaria hydropiperrdquo LWT Food Science and Technology vol46 no 2 pp 468ndash476 2012
[52] PH FanA EHayAMarstonHX Lou andKHostettmannldquoChemical variability of the invasive neophytes Polygonumcuspidatum Sieb and Zucc and Polygonum sachalinensis FSchmidt ex Maximrdquo Biochemical Systematics and Ecology vol37 no 1 pp 24ndash34 2009
[53] P Liu Y Hu D H Guo et al ldquoPotential antidepressantproperties of Radix Polygalae (Yuan Zhi)rdquo Phytomedicine vol17 no 10 pp 794ndash799 2010
[54] J F Wu S B Chen S L Chen and P F Tu ldquoThe chemical con-stituents of Polygala hongkongensisHemslrdquoActa PharmaceuticaSinica vol 42 no 7 pp 757ndash761 2007
[55] Y Song Y Jiang D Bi X Tian L Liang and P Tu ldquoChemicalconstituents from n-butanol extract of aerial part of Polygalasibiricardquo Zhongguo Zhongyao Zazhi vol 37 no 4 pp 471ndash4742012
[56] Y Ikeya S Takeda M Tunakawa et al ldquoCognitive improvingand cerebral protective effects of acylated oligosaccharides inPolygala tenuifoliardquo Biological and Pharmaceutical Bulletin vol27 no 7 pp 1081ndash1085 2004
[57] C J Zheng C L Hu X Q Ma C Peng H Zhang and L PQin ldquoCytotoxic phenylpropanoid glycosides from Fagopyrumtataricum (L) Gaertnrdquo Food Chemistry vol 132 no 1 pp 433ndash438 2012
[58] X Li Y F Zhang L Yang et al ldquoChemical profiling ofconstituents of Smilacis glabrae using ultra-high pressure liquidchromatography coupled with LTQ orbitrap mass spectrome-tryrdquo Natural Product Communications vol 7 no 2 pp 181ndash1842012
[59] T-T Sun D-W Zhang Y Han F-Y Dong andWWang ldquoSmi-lasides M and N two new phenylpropanoid glycosides fromSmilax ripariardquo Journal of Asian Natural Products Research vol14 no 2 pp 165ndash170 2012
[60] J Li X Bi G Zheng Y Hitoshi T Ikeda and T NoharaldquoSteroidal glycosides and aromatic compounds from Smilaxripariardquo Chemical amp Pharmaceutical Bulletin vol 54 no 10 pp1451ndash1454 2006
[61] N Wang X Yao R Ishii and S Kitanaka ldquoBioactive sucroseesters from Bidens parviflorardquo Phytochemistry vol 62 no 5 pp741ndash746 2003
[62] S Nakamura K Fujimoto T Matsumoto et al ldquoAcylatedsucroses and acylated quinic acids analogs from the flower budsof Prunus mume and their inhibitory effect on melanogenesisrdquoPhytochemistry vol 92 pp 128ndash136 2013
[63] K Fujimoto SNakamura TMatsumoto et al ldquoMedicinal flow-ers XXXVIII Structures of acylated sucroses and inhibitoryeffects of constituents on aldose reducatase from the flower budsofPrunusmumerdquoChemical and Pharmaceutical Bulletin vol 61no 4 pp 445ndash451 2013
[64] S Nakamura K Fujimoto T Matsumoto et al ldquoStructuresof acylated sucroses and an acylated flavonol glycoside andinhibitory effects of constituents on aldose reductase from theflower buds of Prunus mumerdquo Journal of Natural Medicines vol67 no 4 pp 799ndash806 2013
[65] L-B Dong J He X-Y Li et al ldquoChemical constituents fromthe aerial parts of Musella lasiocarpardquo Natural Products andBioprospecting vol 1 no 1 pp 41ndash47 2011
[66] Y Xiong K Z Deng Y Q Guo W Y Gao and T J ZhangldquoNew chemical constituents from the rhizomes of Sparganiumstoloniferumrdquo Archives of Pharmacal Research vol 32 no 5 pp717ndash720 2009
[67] Y Xiong K-Z Deng Y-Q Guo W-Y Gao and T-J ZhangldquoTwo new sucrose esters from Sparganium stoloniferumrdquo Jour-nal of Asian Natural Products Research vol 10 no 5 pp 425ndash428 2008
[68] B Chen N L Wang J H Huang and X S Yao ldquoIridoidand phenylpropanoid glycosides from Scrophularia ningpoensis
22 Evidence-Based Complementary and Alternative Medicine
Hemslrdquo Asian Journal of Traditional Medicines vol 2 no 3 pp119ndash123 2007
[69] H Chen Y Z Zhou L Qiao et al ldquoTwo new compounds fromCynanchum amplexicaulerdquo Journal of Asian Natural ProductsResearch vol 10 no 3 pp 248ndash251 2008
[70] C-L Chang L-J Zhang R Y Chen et al ldquoAntioxidant andanti-inflammatory phenylpropanoid derivatives from Calamusquiquesetinerviusrdquo Journal of Natural Products vol 73 no 9 pp1482ndash1488 2010
[71] Y Kawai H Kumagai H Kurihara K Yamazaki R Sawanoand N Inoue ldquo120573-Glucosidase inhibitory activities of phenyl-propanoid glycosides vanicoside A and B from Polygonumsachalinense rhizomerdquo Fitoterapia vol 77 no 6 pp 456ndash4592006
[72] P V Kiem N X Nhiem N X Cuong et al ldquoNew phenyl-propanoid esters of sucrose from Polygonum hydropiper andtheir antioxidant activityrdquo Archives of Pharmacal Research vol31 no 11 pp 1477ndash1482 2008
[73] K J Wang Y J Zhang and C R Yang ldquoAntioxidant phenolicconstituents from Fagopyrum dibotrysrdquo Journal of Ethnophar-macology vol 99 no 2 pp 259ndash264 2005
[74] N Cho J Huh H Yang et al ldquoChemical constituentsof Polygala tenuifolia roots and their inhibitory activity onlipopolysaccharide-induced nitric oxide production in BV2microgliardquo Journal of Enzyme Inhibition and Medicinal Chem-istry vol 27 no 1 pp 1ndash4 2012
[75] Q Ren C S Wu and J L Zhang ldquoUse of on-line stop-flowheart-cutting two-dimensional high performance liquid chro-matography for simultaneous determination of 12 major con-stituents in tartary buckwheat (Fagopyrum tataricum Gaertn)rdquoJournal of Chromatography A vol 1304 pp 257ndash262 2013
[76] Q Ren C S Wu Y Ren and J L Zhang ldquoCharacterizationand identification of the chemical constituents from tartarybuckwheat (Fagopyrum tataricumGaertn) by high performanceliquid chromatographyphotodiode array detectorlinear iontrap FTICR hybrid mass spectrometryrdquo Food Chemistry vol136 no 3-4 pp 1377ndash1389 2013
[77] W Li Y N Sun X T Yan et al ldquoNF-120581B inhibitory activityof sucrose fatty acid esters and related constituents fromAstragalus membranaceusrdquo Journal of Agricultural and FoodChemistry vol 61 no 29 pp 7081ndash7088 2013
[78] J T Cheng J He Y Li et al ldquoThree new sucrose fatty acid estersfrom Equisetum hiemale LrdquoHelvetica Chimica Acta vol 95 no7 pp 1158ndash1163 2012
[79] Y Jiang and P-F Tu ldquoTenuifoliose Q a new oligosaccharideester from the root of Polygala tenuifoliaWilldrdquo Journal of AsianNatural Products Research vol 5 no 4 pp 279ndash283 2003
[80] M Yoshikawa H Matsuda T Morikawa H H Xie S Naka-mura and O Muraoka ldquoPhenylethanoid oligoglycosides andacylated oligosugars with vasorelaxant activity from Cistanchetubulosardquo Bioorganic ampMedicinal Chemistry vol 14 no 22 pp7468ndash7475 2006
[81] P-F Tu H-M Shi Z-H Song Y Jiang and Y-Y ZhaoldquoChemical constituents of Cistanche sinensisrdquo Journal of AsianNatural Products Research vol 9 no 1 pp 79ndash84 2007
[82] C-L Si Y-Y Lu P-P Qin R-C Sun and Y-H Ni ldquoPhenolicextractives with chemotaxonomic significance from the bark ofPaulownia tomentosa var tomentosardquo BioResources vol 6 no4 pp 5086ndash5098 2011
[83] J Wu S Zhang Q Xiao et al ldquoPhenylethanoid and aliphaticalcohol glycosides from Acanthus ilicifoliusrdquo Phytochemistryvol 63 no 4 pp 491ndash495 2003
[84] Y Jiang and P-F Tu ldquoAnalysis of chemical constituents inCistanche speciesrdquo Journal of Chromatography A vol 1216 no11 pp 1970ndash1979 2009
[85] H Otsuka H Kuwabara and H Hoshiyama ldquoIdentification ofsucrose diesters of aryldihydronaphthalene-type lignans fromTrigonotis peduncularisand the nature of their fluorescencerdquoJournal of Natural Products vol 71 no 7 pp 1178ndash1181 2008
[86] M-R Suo J-S Yang and Q-H Liu ldquoLignan oligosaccharideesters from Eritrichium rupestrerdquo Journal of Natural Productsvol 69 no 4 pp 682ndash684 2006
[87] P-F Tu Z-H Song H-M Shi Y Jiang and Y-Y ZhaoldquoArylethyl (=phenylethanoid) glycosides and oligosaccharidefrom the stem of Cistanche tubulosardquo Helvetica Chimica Actavol 89 no 5 pp 927ndash935 2006
[88] M-H Shyr T-H Tsai and L-C Lin ldquoRossicasins A Band rosicaside F three new phenylpropanoid glycosides fromBoschniakia rossicardquoChemical and Pharmaceutical Bulletin vol54 no 2 pp 252ndash254 2006
[89] R FangNCVeitchGCKiteM J RHowes EA Porter andM S J Simmonds ldquoGlycosylated constituents of Iris fulvaandIris brevicaulisrdquoChemical amp Pharmaceutical Bulletin vol 59 no1 pp 124ndash128 2011
[90] J Fu L Zuo J Yang R Chen and D Zhang ldquoOligosaccharidepolyester and triterpenoid saponins from the roots of Polygalajaponicardquo Phytochemistry vol 69 no 7 pp 1617ndash1624 2008
[91] M-C Cheng C-Y Li H-C Ko F-N Ko Y-L Lin andT-S Wu ldquoAntidepressant principles of the roots of polygalatenuifoliardquo Journal of Natural Products vol 69 no 9 pp 1305ndash1309 2006
[92] H T Chang and P F Tu ldquoNew oligosaccharide esters andxanthone C-glucosides from Polygala telephioidesrdquo HelveticaChimica Acta vol 90 no 5 pp 944ndash950 2007
[93] J Li L Feng J Dai R Wang and T Nohara ldquoChemical con-stituents from Polygala telephioidesrdquo China Journal of ChineseMateria Medica vol 34 no 4 pp 402ndash405 2009
[94] W-P Yin T-Z Zhao and H-Y Zhang ldquoA novel oligosaccha-ride ester from Syringa pubescensrdquo Journal of Asian NaturalProducts Research vol 10 no 1 pp 95ndash100 2008
[95] M Valko D Leibfritz J Moncol M T D Cronin M Mazurand J Telser ldquoFree radicals and antioxidants in normal physio-logical functions and human diseaserdquoThe International Journalof Biochemistry amp Cell Biology vol 39 no 1 pp 44ndash84 2007
[96] D Krishnaiah R Sarbatly and R Nithyanandam ldquoA review ofthe antioxidant potential of medicinal plant speciesrdquo Food andBioproducts Processing vol 89 no 3 pp 217ndash233 2011
[97] P Liu Y Hu D-H Guo et al ldquoAntioxidant activity ofoligosaccharide ester extracted from Polygala tenuifolia roots insenescence-accelerated micerdquo Pharmaceutical Biology vol 48no 7 pp 828ndash833 2010
[98] Y Hu H-B Liao G Dai-Hong P Liu Y-Y Wang and KRahman ldquoAntidepressant-like effects of 361015840-disinapoyl sucroseon hippocampal neuronal plasticity and neurotrophic signalpathway in chronically mild stressed ratsrdquo NeurochemistryInternational vol 56 no 3 pp 461ndash465 2010
[99] Y Hu H B O Liao P Liu D-H Guo and K RahmanldquoA bioactive compound from Polygala tenuifolia regulatesefficiency of chronic stress on hypothalamic-pituitary-adrenalaxisrdquo Pharmazie vol 64 no 9 pp 605ndash608 2009
[100] A Jungbauer and SMedjakovic ldquoAnti-inflammatory propertiesof culinary herbs and spices that ameliorate the effects ofmetabolic syndromerdquoMaturitas vol 71 no 3 pp 227ndash239 2012
Evidence-Based Complementary and Alternative Medicine 23
[101] Q Xu Y Wang S Guo Z Shen and L Yang ldquoAnti-inflammatory and analgesic activity of aqueous extract of Flospopulirdquo Journal of Ethnopharmacology vol 152 no 3 pp 540ndash545 2014
[102] K S Kim D S Lee G S Bae et al ldquoThe inhibition of JNKMAPK and NF-120581B signaling by tenuifoliside A isolated fromPolygala tenuifolia in lipopolysaccharide-induced macrophagesis associated with its anti-inflammatory effectrdquo European Jour-nal of Pharmacology vol 721 no 1ndash3 pp 267ndash276 2013
[103] J-G Lee J-M Yon C Lin A Y Jung K Y Jung and S-YNamldquoCombined treatment with capsaicin and resveratrol enhancesneuroprotection against glutamate-induced toxicity in mousecerebral cortical neuronsrdquo Food and Chemical Toxicology vol50 no 11 pp 3877ndash3885 2012
[104] M L Jin S Y Park Y H Kim J-I Oh S J Lee andG Park ldquoThe neuroprotective effects of cordycepin inhibitglutamate-induced oxidative andER stress-associated apoptosisin hippocampal HT22 cellsrdquo NeuroToxicology vol 41 pp 102ndash111 2014
[105] P Liu Y Hu J Li et al ldquoProtection of SH-SY5Y neuronal cellsfrom glutamate-induced apoptosis by 36rsquo-disinapoyl sucrosea bioactive compound isolated from radix polygalardquo Journal ofBiomedicine and Biotechnology vol 2012 Article ID 728342 5pages 2012
[106] P-B Li W-L Lin Y-G Wang W Peng X-Y Cai and W-WSu ldquoAntidiabetic activities of oligosaccharides of Ophiopogonisjaponicus in experimental type 2 diabetic ratsrdquo InternationalJournal of Biological Macromolecules vol 51 no 5 pp 749ndash7552012
[107] T Liu Y M Yip L Song et al ldquoInhibiting enzymatic starchdigestion by the phenolic compound diboside A a mechanisticand in silico studyrdquo Food Research International vol 54 no 1pp 595ndash600 2013
[108] F Cote andMGHahn ldquoOligosaccharins structures and signaltransductionrdquo Plant Molecular Biology vol 26 no 5 pp 1379ndash1411 1994
[109] RACreelman and J EMullet ldquoOligosaccharins brassinolidesand jasmonates nontraditional regulators of plant growthdevelopment and gene expressionrdquo Plant Cell vol 9 no 7 pp1211ndash1223 1997
[110] L Jiao D Wan X Zhang B Li H Zhao and S LiuldquoCharacterization and immunostimulating effects on murineperitoneal macrophages of oligosaccharide isolated from Panaxginseng CAMeyerrdquo Journal of Ethnopharmacology vol 144 no3 pp 490ndash496 2012
Submit your manuscripts athttpwwwhindawicom
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Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
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Disease Markers
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Oxidative Medicine and Cellular Longevity
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Parkinsonrsquos Disease
Evidence-Based Complementary and Alternative Medicine
Volume 2014Hindawi Publishing Corporationhttpwwwhindawicom
Evidence-Based Complementary and Alternative Medicine 7
Table2Ph
enylprop
anoid-deriv
eddisaccharid
eeste
rs
Num
ber
Nam
eR 1
R 2R 3
R 4R 5
R 6R 7
R 8Source
Parts
Reference
35Sibiric
oseA
6H
HH
HK
HH
HPolyg
alatricornis
Polyg
alatenu
ifolia
Roots
Root
barks
[37ndash40
]
3631015840-O
-FeruloylsucroseSibiricose
A5
HH
HH
IH
HH
Polyg
alatenu
ifolia
Trillium
kamtsc
haticum
Roots
Und
ergrou
ndparts
[38ndash42]
37GlomeratoseA
HH
HH
LH
HH
Polyg
alatricornis
Roots
[37]
38LapathosideD
HH
HH
GG
HH
Polyg
onum
sachalinense
Stem
s[43]
39Helo
niosideA
HH
HH
II
HH
Trillium
kamtsc
haticum
Smila
xbracteata
Paris
polyphylla
varyunn
anensis
Und
ergrou
ndparts
Aeria
lparts
Roots
[4144
45]
40Helo
niosideB
AcH
HH
II
HH
Smila
xbracteata
Smila
xchina
Smila
xrip
aria
Heterosmila
xerythrantha
Aeria
lparts
Stem
sRo
otsa
ndrhizom
es
[4446
ndash48]
41Paris
polysid
eFH
HH
HG
IH
HPa
risPolyphylla
varyunn
anensis
Rhizom
es[4950]
42Hydropiperosid
eH
HH
HG
GH
GPolyg
onum
sachalinense
Polyg
onum
cuspidatum
Persica
riahydropiper
Stem
sLeaves
[435152]
43Tricorno
seB
DAc
HH
LH
HH
Polyg
alatricornis
Roots
[37]
44Tenu
ifolisideA
FH
HH
LH
HH
Polyg
alatenu
ifolia
Polygalahongkongensis
Polyg
alasib
irica
Roots
Who
leplants
Aeria
lparts
[3840
4253ndash
56]
45Tataris
ideA
AcH
HAc
GG
HAc
Fagopyrum
tataric
umRo
ots
[57]
46Tataris
ideE
HH
HAc
GG
HAc
Fagopyrum
tataric
umRo
ots
[57]
47Tataris
ideG
HH
HH
IG
HG
Fagopyrum
tataric
umRo
ots
[57]
48Sm
iglasid
eAAc
AcH
AcI
IH
ISm
ilaxrip
aria
Rootsa
ndrhizom
es[47]
49Sm
iglasid
eBAc
HH
AcI
IH
ISm
ilaxrip
aria
Rootsa
ndrhizom
es[47]
50Sm
iglasid
eEAc
HH
AcI
IH
GSm
ilaxchina
Stem
s[46]
51Sm
ilasid
eAAc
AcH
HI
IH
HSm
ilaxchina
Stem
s[46]
52Sm
ilasid
eBH
HH
AcI
IH
HSm
ilaxchina
Stem
s[46]
53Sm
ilasid
eCH
HH
HI
IH
GSm
ilaxchina
Stem
s[46]
54Sm
ilasid
eDH
HH
HI
IAc
GSm
ilaxchina
Stem
s[46]
8 Evidence-Based Complementary and Alternative Medicine
Table2Con
tinued
Num
ber
Nam
eR 1
R 2R 3
R 4R 5
R 6R 7
R 8Source
Parts
Reference
55Sm
ilasid
eEAc
HH
HI
IH
GSm
ilaxbracteata
Smila
xchina
Aeria
lparts
Stem
s[4446
]
56Sm
ilasid
eFAc
HH
AcG
IH
GSm
ilaxchina
Stem
s[46]
57Sm
ilasid
eGH
HH
HG
IH
GSm
ilaxbracteata
Smilacis
glabrae
Aeria
lparts
Rhizom
es[4458]
58Sm
ilasid
eHH
HH
AcG
IH
GSm
ilaxbracteata
Aeria
lparts
[44]
59Sm
ilasid
eIAc
HH
HG
IH
GSm
ilaxbracteata
Aeria
lparts
[44]
60Sm
ilasid
eJH
HH
HG
IH
ISm
ilaxbracteata
Smilacis
glabrae
Aeria
lparts
Rhizom
es[4458]
61Sm
ilasid
eKH
HH
AcI
IH
GSm
ilaxbracteata
Aeria
lparts
[44]
62Sm
ilasid
eLH
HH
HI
IH
ISm
ilaxbracteata
Smilacis
glabrae
Aeria
lparts
Rhizom
es[4458]
63Sm
ilasid
eMAc
HH
AcCis-feruloyl
IH
HSm
ilaxrip
aria
Rootsa
ndrhizom
es[59]
64Sm
ilasid
eNAc
HH
AcI
Cis-
feruloyl
HH
Smila
xrip
aria
Rootsa
ndrhizom
es[59]
65Sm
ilasid
ePH
HH
AcI
IH
ISm
ilaxrip
aria
Rootsa
ndrhizom
es[47]
66310158404101584061015840-O
-Tri-
feruloylsucrose
HH
HH
II
IH
Smila
xrip
aria
Rhizom
esand
roots
[60]
6761015840-O
-Cou
maroylsu
crose
HH
HH
HG
HH
Bidens
parviflora
Who
leplants
[61]
6811015840 -O-C
oumaroyl-61015840-O
-feruloylsucrose
HH
HH
HI
HG
Smila
xbracteata
Aeria
lparts
[44]
694-O-Benzoyl-31015840-345-
trim
etho
xycinn
amoylsu
crose
HD
HH
LH
HH
Polyg
alatricornis
Roots
[37]
706-O-Benzoyl-31015840-O
-345-
trim
etho
xycinn
amoylsu
crose
DH
HH
LH
HH
Polyg
alatricornis
Roots
[37]
716-O-Benzoyl-31015840-O
-sin
apoylsu
crose
DH
HH
KH
HH
Polyg
alatricornis
Roots
[37]
726-O-p-M
etho
xybenzoyl-31015840-O
-345-
trim
etho
xycinn
amoylsu
crose
EH
HH
LH
HH
Polyg
alatenu
ifolia
Roots
[56]
7326-Di-a
cetyl-3101584061015840-di-
feruloylsucrose
AcH
HAc
II
HH
Smila
xchina
Smila
xrip
aria
Heterosmila
xerythrantha
Stem
sRo
otsa
ndrhizom
esAe
rialp
arts
[46ndash
4859]
7426-Di-a
cetyl-31015840-O
-cis-feruloy-
61015840-tr
ans-feruloylsucrose
AcH
HAc
Cis-feruloy
IH
HSm
ilaxrip
aria
Rootsa
ndrhizom
es[59]
Evidence-Based Complementary and Alternative Medicine 9
Table2Con
tinued
Num
ber
Nam
eR 1
R 2R 3
R 4R 5
R 6R 7
R 8Source
Parts
Reference
7526-Di-a
cetyl-31015840-O
-tran
s-feruloy-
61015840-cis-feruloylsucrose
AcH
HAc
ICis-
feruloyl
HH
Smila
xrip
aria
Rootsa
ndrhizom
es[59]
76Re
galosid
eAAc
HH
HI
HH
HTrillium
kamtsc
haticum
Und
ergrou
ndparts
[41]
77Tricorno
seA
AcH
HH
LH
HH
Polyg
alatricornis
Roots
[37]
78Mum
eose
AH
HH
AcG
HH
HPrun
usmum
eFlow
erbu
ds[6263]
79Mum
eose
BAc
HAc
HG
HH
HPrun
usmum
eFlow
erbu
ds[6263]
80Mum
eose
CAc
HAc
AcG
HH
HPrun
usmum
eFlow
erbu
ds[6263]
81Mum
eose
DAc
AcAc
AcG
HH
AcPrun
usmum
eFlow
erbu
ds[6263]
82Mum
eose
EAc
AcAc
AcCis-
coum
aroyl
HH
AcPrun
usmum
eFlow
erbu
ds[6263]
83Mum
eose
FAc
AcAc
HG
HH
HPrun
usmum
eFlow
erbu
ds[63]
84Mum
eose
GAc
HAc
HG
HAc
HPrun
usmum
eFlow
erbu
ds[63]
85Mum
eose
HH
HAc
AcG
HAc
HPrun
usmum
eFlow
erbu
ds[63]
86Mum
eose
IAc
AcAc
HG
AcH
HPrun
usmum
eFlow
erbu
ds[63]
87Mum
eose
JAc
AcAc
AcG
HAc
AcPrun
usmum
eFlow
erbu
ds[63 ]
88Mum
eose
KH
HAc
AcG
HH
HPrun
usmum
eFlow
erbu
ds[64]
89Mum
eose
LAc
HAc
AcG
HAc
HPrun
usmum
eFlow
erbu
ds[64]
90Mum
eose
MAc
AcAc
HG
HAc
AcPrun
usmum
eFlow
erbu
ds[64]
91Mum
eose
NAc
AcAc
HG
AcAc
HPrun
usmum
eFlow
erbu
ds[64]
92Mum
eose
OAc
HAc
AcG
HAc
AcPrun
usmum
eFlow
erbu
ds[64]
9311015840 2346-O-Penta-acetyl-31015840-O
-tra
ns-cou
maroylsu
crose
AcAc
AcAc
GH
HAc
Musellalasio
carpa
Aeria
lparts
[65]
9411015840 2346-O-Penta-acetyl-31015840-O
-cis-cou
maroylsu
crose
AcAc
AcAc
Cis-
coum
aroyl
HH
AcMusellalasio
carpa
Aeria
lparts
[65]
9511015840 236-O-Tetra-acetyl-31015840-O
-cis-
feruloylsucrose
AcH
AcAc
Cis-feruloyl
HH
AcSparganium
stolonifer
umRh
izom
es[66]
9611015840 246-O-Tetra-acetyl-31015840-O
-tra
ns-fe
ruloylsucrose
AcAc
HAc
IH
HAc
Sparganium
stolonifer
umRh
izom
es[66]
9711015840 236-O-Tetra-acetyl-31015840-O
-tra
ns-fe
ruloylsucrose
AcH
AcAc
IH
HAc
Sparganium
stolonifer
umRh
izom
es[67]
98Sibirio
sideA
MH
HH
HH
HH
Scrophularianingpoensis
Roots
[68]
99SibricoseA
1K
HH
HH
HH
HCy
nanchu
mam
plexica
ule
Roots
[69]
100
6-O-C
affeoylsucrose
JH
HH
HH
HH
Scrophularianingpoensis
Roots
[68]
101
Acretosid
eI
HH
HH
HH
HScrophularianingpoensis
Roots
[68]
10 Evidence-Based Complementary and Alternative Medicine
Table2Con
tinued
Num
ber
Nam
eR 1
R 2R 3
R 4R 5
R 6R 7
R 8Source
Parts
Reference
102
Tenu
ifolisideB
FH
HH
KH
HH
Polyg
alatenu
ifolia
Roots
[4256]
103
Tenu
ifolisideC
KH
HH
LH
HH
Polyg
alatricornis
Polyg
alatenu
ifolia
Roots
[374256]
104
Heterosmilasid
eH
HI
HH
IH
HHeterosmila
xerythrantha
Aeria
lparts
[48]
105
Quiqu
esetinerviusideA
HI
HH
II
HH
Calamus
quiquesetin
ervius
Stem
s[70]
106
Quiqu
esetinerviusideB
AcI
HH
II
HH
Calamus
quiquesetin
ervius
Stem
s[70]
107
Quiqu
esetinerviusideC
HI
HAc
II
HH
Calamus
quiquesetin
ervius
Stem
s[70]
108
Quiqu
esetinerviusideD
AcG
HH
II
HH
Calamus
quiquesetin
ervius
Stem
s[70]
109
Quiqu
esetinerviusideE
HG
HAc
II
HH
Calamus
quiquesetin
ervius
Stem
s[70]
110
Vanicosid
eAI
HH
AcG
GH
G
Polyg
onum
sachalinensis
Polyg
onum
cuspidatum
Polyg
onum
hydropiper
Stem
sLeaves
Rhizom
es[51527172]
111
Vanicosid
eBI
HH
HG
GH
G
Polyg
onum
sachalinensis
Polyg
onum
cuspidatum
Persica
riahydropiper
Stem
sLeaves
Rhizom
es[4351527172]
112
Vanicosid
eDG
HH
HG
GH
GPersica
riahydropiper
Leaves
[51]
113
Vanicosid
eEI
AcH
AcG
GH
GPolyg
onum
hydropiper
Stem
sand
leaves
[72]
114
LapathosideA
IH
HH
GG
HI
Polyg
onum
sachalinensis
Polyg
onum
cuspidatum
Fagopyrum
dibotrys
Stem
sRh
izom
es[5173]
115
LapathosideC
IH
HH
GG
HH
Polyg
onum
sachalinensis
Polyg
onum
cuspidatum
Stem
s[4352]
116
DibosideA
GH
HH
GI
HG
Fagopyrum
tataric
umFagopyrum
dibotrys
Roots
Rhizom
es[57]
117
Hidropiperosid
eAI
HH
HH
GH
GPolyg
onum
hydropiper
Stem
sand
leaves
[72]
118
Hidropiperosid
eBI
HH
AcG
GH
IPolyg
onum
hydropiper
Stem
sand
leaves
[72]
119
Tataris
ideB
IH
HAc
GG
HAc
Fagopyrum
tataric
umRo
ots
[57]
Evidence-Based Complementary and Alternative Medicine 11
Table2Con
tinued
Num
ber
Nam
eR 1
R 2R 3
R 4R 5
R 6R 7
R 8Source
Parts
Reference
120
Tataris
ideC
IAc
HAc
GG
HAc
Fagopyrum
tataric
umRo
ots
[57]
121
Tataris
ideD
GH
HAc
GI
HH
Fagopyrum
tataric
umRo
ots
[57]
122
Tataris
ideF
GH
HH
II
HG
Fagopyrum
tataric
umRo
ots
[57]
123
310158406-O
-Di-sinapoylsu
crose
KH
HH
KH
HH
Polyg
alatricornis
Polygalahongkongensis
Polyg
alasib
irica
Polyg
alatenu
ifolia
Cynanchu
mam
plexica
ule
Roots
Root
barks
Who
leplants
Aeria
lparts
[37ndash394153ndash
566974]
124
661015840-O
-Di-c
oumaroylsu
crose
GH
HH
HG
HH
Bidens
parviflora
Who
leplants
[61]
125
11015840 3101584061015840-O
-Tri-
coum
aroyl-6
-feruloylsucrose
IH
HH
GG
HG
Fagopyrum
tataric
umRo
ots
[7576]
126
3101584061015840-O
-Di-c
oumaroyl-110158406-O
-di-
feruloylsucrose
IH
HH
GG
HI
Fagopyrum
tataric
umRo
ots
[7576]
127
31015840-O
-Cou
maroyl-11015840610158406-O
-tri-
feruloylsucrose
IH
HH
IG
HI
Fagopyrum
tataric
umRo
ots
[7576]
128
11015840 31015840610158406-O
-Tetra-fe
ruloylsucrose
IH
HH
II
HI
Fagopyrum
tataric
umRo
ots
[7576]
SeeS
chem
e2
12 Evidence-Based Complementary and Alternative Medicine
131130129
CH2OHOH
OH
OO
OH
C
C
HH
HHO
OO
O
HO
HOHO
HO
HOOH
OHOHOH
OHOH
HOO
O
O
O
HO
HO
OH
OHOHOH
OHOH
HOO
O
O
O
HO
Figure 3
12
3
4
5
6
1998400
2998400
3998400
4998400
5998400
6998400
HO
O
O
R1O
R2O
R8O
R7OOR3
OR4 OR5OR6
Scheme 2
antidepressant cytotoxic antineoplastic anti-inflammatoryantidiabetic plant growth-regulatory neuroprotective andcerebral protective activities Lignan-derived disaccharideesters phenylpropanoid-derived tetrasaccharide esters andpentasaccharide esterswith biological activities have not beenreported Aside from the isolated constituents oligosaccha-ride mixtures from Rehmannia glutinosa Panax ginseng andScrophularia ningpoensiswere also reported to display diversepharmacological activities such as antidiabetic immunopo-tentiating enhanced memory and antineoplastic activitiesThese active compounds and mixtures could serve as thevaluable candidates to be developed as possible drugs for thetreatment and prevention of diseases
31 Antioxidant Activity The adverse effects of oxidativestress proposed to play significant roles in the pathogenesis ofcardiovascular diseases atherosclerosis hypertension can-cer diabetes mellitus neurodegenerative diseases rheuma-toid arthritis ischemiareperfusion injury and ageing havebecome an inevitable and serious issue [95 96] Scientistshave thus made great efforts to explore antioxidants frommedicinal plants by using different kinds of assay methodswhich include DPPH radical scavenging assay hydroxylradical scavenging assay superoxide anion scavenging assayand ABTS radical scavenging method [96]
Lapathosides C and D hydropiperoside vanicoside Bhidropiperosides A and B lapathoside A and diboside Awere isolated from the Polygonum Persicaria and Fagopyrumgenera belonging to the Polygonaceae family The DPPH testrevealed that free radical-scavenging activity of the isolatedcompounds termed lapathoside C (115) hydropiperoside(42) vanicoside B (111) and lapathoside D (38) increasedin turn and lapathoside D exhibited strongest scavengingability with an IC
50of 0088 120583M [43] Hidropiperosides A
and B (117 118) were reported to show obvious antioxidantresponse to DPPH radicals with the SC
50values of 234
and 267 120583gmL respectively while vanicoside E moderatelyexhibited the same activity with a SC
50value of 490 120583gmL
[72] Lapathoside A (114) and diboside A (116) just showedlower antioxidant activities with the SC
50values of 19948 and
16552 120583M respectively [73]Smiglasides A and B smilaside P 26-di-acetyl-3101584061015840-
di-feruloylsucrose helonioside B smilasides GndashL and het-erosmilaside were isolated from the Heterosmilax and Smi-lax genera Compared with ascorbic acid (IC
5014352 120583M)
used as positive control smiglasides A and B and smi-laside P (48 49 65) (IC
5033958 33066 and 31449 120583M
resp) showed higher antioxidant activities than 26-di-acetyl-3101584061015840-di-feruloylsucrose (73) and helonioside B (40) (IC
50
63166 and 51827120583M resp) [47] Additionally Nhiem et alreported that helonioside B heterosmilaside (104) and 26-di-acetyl-3101584061015840-di-feruloylsucrose exhibited important DPPHradical scavenging activities with the SC
50values of 91 127
and 87 120583gmL respectively [48] Compared with smilasidesG-I (57ndash59) (ED
50685ndash794120583M) smilasides JndashL (60ndash62)
showed higher radical scavenging activities with an ED50
value of 267ndash327120583M [44]Five quiquesetinerviusides AndashE (105ndash109) isolated from
the Calamus genus showed weak DPPH scavenging activ-ities (IC
50604ndash1018120583M) but exhibited better hydroxyl
radical scavenging activities (IC50
36ndash84 120583M) Moreoverquiquesetinerviuside C showed superoxide anion scaveng-ing activity with an IC
50value of about 1843 120583M [70]
Liu et al investigated the antioxidant capacity of 310158406-O-di-sinapoylsucrose (DISS) (123) by using the acceleratedsenescence-prone short-lived mice (SAMP) in vivo Theanalyses indicated that the activities of antioxidant enzymesof SOD and glutathione peroxidase ascended obviously inSAMP mice when amended with DISS 50mgkg MoreoverDISS could downregulate and even restore the level ofmalondialdehyde in SAMP model group [97]
From the above studies it can be concluded that oligosac-charide esters with antioxidant activities have been identifiedin the Polygonaceae Liliaceae Smilacaceae and Arecaceaefamilies The results of the antioxidant assays show that theincreased number of phenolic hydroxyl groups and acetylgroups could produce higher antioxidant activity Fan etal indicated that the increased number of phenylpropanoidgroups was not beneficial to free radical scavenging activity[43] Zhang et al pointed out that oligosaccharide esters withferuloyl groups exhibited better antioxidant activities thanthose with coumaroyl groups [44]
Evidence-Based Complementary and Alternative Medicine 13
Table 3 Fatty acid-derived disaccharide esters
Number Name R1 R2 Source Parts Reference132 61015840-O-Linoleylsucrose H O Astragalus membranaceus Roots [77]133 61015840-O-Palmitoylsucrose H P Astragalus membranaceus Roots [77]134 6-O-Palmitoylsucrose P H Astragalus membranaceus Roots [77]
135 61015840-O-Linolenoylsucrose H N Astragalus membranaceusEquisetum hiemale
RootsAerial parts [77 78]
136 6-O-Linoleylsucrose O H Astragalus membranaceus Roots [77]137 6-O-Myristoylsucrose Q H Astragalus membranaceus Roots [77]
138 6-O-[(7Z10Z13Z)-Hexadeca-71013-trienoyl]sucrose H R Equisetum hiemale Aerial parts [78]
139 6-O-[(7Z10Z)-Hexadeca-710-dienoyl]sucrose H S Equisetum hiemale Aerial parts [78]
See Scheme 3
12
3
4
5
6
1998400
2998400
3998400
4998400
5998400
6998400
HO
O
O
R1O
R2O
R8O
R7OOR3
OR4 OR5OR6
O
O
O
18
18
1616
16
14
N linolenoyl
O linoleyl
P palmitoyl
Q myristoyl
O
O
O
R hexadeca-71013-trienoyl
S hexadeca-710-dienoyl
Scheme 3
32 Antidepressant Activity The oligosaccharides obtainedfrom the Morinda genus not only show specific antidepres-sant and antistress activities but also have no suppression orexcitatory effects on central nervous system as well Whatis more they can be taken orally with little toxicity [21]The inulin-type hexasaccharide (IHS) (9) from Morindaofficinalis obviously exhibited cytoprotective activity whichcontributed to the antidepressant effect not only by providingthe PC12 with protection against Cort-induced lesion withIHS 0625 and 125 120583Mbut also by reducing theCort-induced[Ca2+]
119894overloading with IHS 25 and 10 120583M IHS 5 and
10 120583Mupregulated the nerve growth factormRNAexpressionin Cort-induced PC12 cells [22] Polygalatenosides A (181)and B (182) were isolated from the Polygala genus Theysignificantly inhibited the isotope-labeled RTI-55 binding to
norepinephrine transporter protein with the IC50
values of300 and 604 120583M respectively [91]
DISS and tenuifoliside A were isolated from the PolygalaandCynanchum genera Liu et al investigated the antidepres-sant effect of YZ ethanol extract based on the tail suspensiontest (TST) and forced swimming test (FST) which arethe ease-of-use and widely-accepted models for estimatingantidepressant activities in mice The results indicated thatYZ-50 fraction at a dose of 200mgkgwas able to significantlydecrease the immobility time in TST Furthermore YZ-50possessed ability to inhibit corticosterone-induced injury ofhuman neuroblastoma SH-SY5Y cells What is more DISS(123) and tenuifoliside A (44) two major compounds of YZ-50 fraction showed effective protective response to the lesionin SY5Y cells [53] The antidepressant-like effect of DISS at
14 Evidence-Based Complementary and Alternative Medicine
H3CO
HO
HOHO
HO
HO
HO
HOHO
O O
OO O
OO
O
O
O
OO
O
O
OH
OH
OH
OH
OCH3
OCH3
CH2OH
CH2OH
CH2OAc
CH2OAc
H3CO
HOHO
HO
O
O
O
OO
O
O
OH
OH
OH
OCH3
CH2OH
CH2OH
H3CO
H3CO H3CO
HOHO
HO
O
O
O
OO
O
O
OH
OH
OH
OCH3
CH2OH
CH2OAc
CH3O
H
HOHO
HO
HO
HOO O
OO O
OO
OH
OCH3
CH2OHCH2OH
H3CO H3CO
H
CH2CH2 HO
HO
HO
HO
HOO O
OO O
OO
OH
OCH3
CH2OHCH2OAc
H3CO
H
CH2
140 141 142
143 144 145
Figure 4
Table 4 Phenylpropanoid-derived trisaccharide esters
Number Name R1 R2 R3 R4 R5 R6 R7 Source Parts Reference146 Tricornose C K H H H H L H Polygala tricornis Roots [37]147 Tricornose D K H H H H K H Polygala tricornis Roots [37]148 Tricornose E K H H H K L H Polygala tricornis Roots [37]149 Tricornose F K H H H I L H Polygala tricornis Roots [37]See Scheme 4
O
OOO
O
R2O
R4O
R3O
R6O
OH
OH
OH
OH
OR1
OR5CH2OR7
Scheme 4
the doses of 5 10 and 20mgkg was also tested in chronicallymild stressed rats DISS was able to exhibit antidepressantactivity by upregulating the expression of noradrenergic-regulated plasticity genes including cell adhesion moleculeL1 brain-derived neurotrophic factor laminin and cAMP
response element binding protein factor in hippocampus[98] DISS improved the reward reaction by increasingsucrose intake and obviously decreased the levels of serumcortisol adrenocorticotrophic hormone and corticotropin-releasing factor Further DISS played an enhanced role inthe expression of mineralocorticoid receptor together withglucocorticoid receptor mRNA [99]
33 Cytotoxic and Antineoplastic Activities Smilasides AndashFand P smiglasides A and B smilaside P and helonioside Awere isolated from the Smilax Trillium and Paris generaKuo et al obtained smilasides AndashF (51ndash56) and evaluatedtheir cytotoxicity against human tumor cell lines comprisinghuman oral epithelium carcinoma (KB) human cervicalcarcinoma (Hela) human colon tumor (DLD-1) humanbreast adenocarcinoma (MCF-7) human lung carcinoma (A-549) and humanmedulloblastoma (Med) cells byMTTassayExperimental data indicated that all but smilaside C showedcytotoxicity against three to six human tumor cell lines(ED50
= 51ndash130 120583gmL) and smilasides DndashF (ED50
= 27ndash50 120583gmL) displayed strong cytotoxic activities against DLD-1 cells [46]Wang et al reported the antitumor constituents of
Evidence-Based Complementary and Alternative Medicine 15
OH
OH
OH
OH
OH
OHOH
OHOH
OHOH
OH
OHOHOH
OH
OH
OH
OHOH
OH
OH
OHOH
H
H H
HO
O
O
O
O
O
O
O
OO
OO
O
OO
O
HO
HO
HO
OO
O
O
OO
OO
O
OO
O
OO
O
OO
O
O
O
OO
O
O
OO
O
OO
OOOO
HO
HO
HO
HO
HO
HO
HO
HO
HO
HO
HOHO
HO
HO
HO
HO
HO
150 151 152
153 180
AcO
AcO
AcOAcO
OAc
OAc
CH2OH
OHOH
OH OHOH
OHOH
OH
OHOH
CH3O
Figure 5
Table 5 Phenylpropanoid-derived tetrasaccharide esters
Number Name R1 R2 R3 Source Parts Reference154 Tricornose G K H K Polygala tricornis Roots [37]155 Tricornose H K K K Polygala tricornis Roots [37]156 Tricornose I K K L Polygala tricornis Roots [37]157 Tricornose J K I L Polygala tricornis Roots [37]158 Tricornose K K I K Polygala tricornis Roots [37]159 Tricornose L K G K Polygala tricornis Roots [37]See Scheme 5
Smilax riparia including smiglasides A (48) and B (49) 26-di-acetyl-3101584061015840-di-feruloylsucrose (73) helonioside B (40)and smilaside P (65) Only smiglasidesA andB and smilasideP exhibited cytotoxicity against human tumor cell lines withdifferent inhibitory concentrations comparing with cisplatinand paclitaxel as positive controls [47] Helonioside A (39)exhibited higher cytotoxicity with the increase of concentra-tion (01ndash100120583gmL) [45] Tatarisides AndashG (45 119ndash121 46122 47) and diboside A (116) from the Fagopyrum genusexerted cytotoxic activities against different human cell linesand the cytotoxicity of tatariside C was the most remarkablewith the IC
50values ranging from 644 to 749 120583gmL [57]
11015840236-O-Tetra-acetyl-31015840-O-cis-feruloylsucrose (95) fromthe Sparganium plants exhibited extremely weak cyto-toxicity against the growth of mice Lung Adenocarcinoma
795 cell lines with an IC50
value of 116 120583gmL [66] SnS-2oligosaccharides mixture including raffinose (3) stachyose(19) and verbascose (21) from the roots of Scrophularianingpoensis had antitumor activity against the growth ofLewis pulmonary carcinoma cells transplanted into mice[18]
Disaccharide esters and oligosaccharides mixture fromthe Liliaceae Polygonaceae Sparganiaceae and Scrpophular-iaceae families showed effective cytotoxic and antineoplasticactivities The study results indicated that feruloyl and acetylgroups play an important role in mediating cytotoxicitywhich seems to be related to the substitution position offeruloyl groups The feruloyl groups at C-6 or C-11015840 are vitalfor cytotoxicity In addition the increased number of acetylgroups could induce higher tumoricidal activity
16 Evidence-Based Complementary and Alternative Medicine
Table 6 Phenylpropanoid-derived pentasaccharide esters
Number Name R1 R2 R3 R4 R5 R6 Source Parts Reference160 Tenuifoliose A G D I Ac Ac Ac Polygala tenuifolia Roots [38 42]161 Tenuifoliose B G D I H Ac Ac Polygala tenuifolia Roots [42]162 Tenuifoliose C G D I H H H Polygala tenuifolia Roots [42]163 Tenuifoliose F G D U Ac Ac Ac Polygala tenuifolia Roots [42]164 Tenuifoliose G G D U Ac H Ac Polygala tenuifolia Roots [42]165 Tenuifoliose H G D G Ac Ac Ac Polygala tenuifolia Roots [38 42 79]166 Tenuifoliose I G D G Ac H Ac Polygala tenuifolia Roots [42 79]167 Tenuifoliose J G D G H Ac Ac Polygala tenuifolia Roots [42]168 Tenuifoliose K G D G H H Ac Polygala tenuifolia Roots [42]169 Tenuifoliose L G D T Ac Ac Ac Polygala tenuifolia Roots [42 79]170 Tenuifoliose M G D T Ac H Ac Polygala tenuifolia Roots [42]171 Tenuifoliose N I D I Ac Ac Ac Polygala tenuifolia Roots [42]172 Tenuifoliose O I D I H Ac Ac Polygala tenuifolia Roots [42]173 Tenuifoliose P I D I H H Ac Polygala tenuifolia Roots [42]174 Tenuifoliose Q G D T H Ac Ac Polygala tenuifolia Roots [79]175 Tenuifoliose S G D G H H H Polygala tenuifolia Roots [42]176 Tenuifoliose T G D I H H H Polygala tenuifolia Roots [42]177 Tenuifoliose V H D I Ac Ac Ac Polygala tenuifolia Roots [42]178 Tenuifoliose W I D U Ac H Ac Polygala tenuifolia Roots [42]179 Tenuifoliose X I D I H H H Polygala tenuifolia Roots [42]See Scheme 6
O
OO
O
O
O
O
OR1
OH
OH
OH
OHOH
OH
HOHO
HO
HO
OR2
R3O
CH2OH
Scheme 5
34 Anti-Inflammatory Activity Inflammation an importantbasic pathological process is a defense response of biopsywith vascular system to damage stimuli such as pathogensimpaired cells and tissues and physical and chemical factorsHowever if the process of inflammatory response cannot endnormally when cell debris and pathogens were cleared thebiological defence response will become causative factor andbring about many diseases such as diabetes cardiovasculardiseases metabolic syndrome and cancer [100 101]
Tenuifoliside A (44) from the Polygala genus exhibitedstrong anti-inflammatory effect not only by suppressing the
production of NO but also by reducing the production ofiNOS prostaglandin E2 cyclooxygenase-2 and proinflam-matory cytokines through the inhibition of the mitogen-activated protein kinases pathway and NF-120581B pathway [102]The anti-inflammatory activities of quiquesetinerviusides D(108) and E (109) from the Calamus genus were evaluated inRAW 2647 cells Both of them showed significant inhibitoryeffects against the production of LPS-stimulated NOwith theIC50values of 90ndash295120583M [70]Six disaccharide fatty acid esters (132ndash137) were iso-
lated from the Astragalus and Equisetum genera The anti-inflammatory effects of these isolated compounds have alsobeen documented The activation of NF-120581B could upregulatethe expression of proinflammatory cytokines inducible nitricoxide synthase (iNOS) and tumornecrosis factor alpha (TNF-120572) The NF-120581B inhibitory activities of compounds 132ndash137were tested in HepG2 cells stimulated with TNF-120572 All ofthese compounds could significantly restrainTNF-120572-inducedNF-120581B transcriptional activities with the IC
50values of 44ndash
247 120583M Li et al pointed out that olefinic bonds and thelength of the fatty acid moieties contributed to the NF-120581B inhibitory activity Furthermore the inhibition increasedsignificantly with the increase of the number of olefinic bondson the aliphatic moiety [77] These results may provide ascientific basis for the development of new anti-inflammatoryagents
35 Neuroprotective and Cerebral Protective Activities Aswe all know glutamate works as a major excitatory aminoacid neurotransmitter in the mammalian central nervous
Evidence-Based Complementary and Alternative Medicine 17
R6O
R2O
OR3
OR5
OR4
CH2OR1
OCH3
Rham
OO
O
OO O
O
O
O
OO
RhamO
O
OH
OH
OHOH
OH
OHOH
OHHO
HO
HO
T O-rhamnosyl-coumaroyl U O-rhamnosyl-feruloyl
Scheme 6
system and plays a crucial role in several physiological pro-cesses [103] However the accumulation of glutamate inducesdiverse acute and chronic neurodegenerative diseases suchas epilepsy ischemic stroke and Parkinsonrsquos disease aswell as Alzheimerrsquos disease [104] DISS (123) isolated fromthe Polygala genus exhibited neuroprotective effect againstglutamate-induced SH-SY5Y neuronal cell damage The invitro test demonstrated that DISS (06 6 and 60 120583molL)played a critical role in increasing cell viability controllinglactate dehydrogenase and attenuated apoptosis ranging from195 to 258 [105]
Tenuifoliside B (102) from the Polygala genus was ableto significantly shorten the coma time of KCN-inducedanoxia mice at the doses of 3 and 10mgkg and it playedan important role in ameliorating the scopolamine-inducedimpairment of performance in passive avoidance task inrats and enhancing the tremors induced by oxotremorine inmiceThese results together demonstrated that tenuifoliside Bpossessed cognitive improving and cerebral protective effects[56]
36 Antidiabetic Activity Diabetes mellitus a chronic debil-itating metabolic disease is characterized by high bloodglucose content and comprises three types termed type Itype II and gestational diabetes [106] Stachyose (19) extract(a part) from Rehmannia glutinosa obviously exhibited theactivity of downregulating fasting plasma glucose level andpartially keeping from hyperglycemia induced by adrenalineand glucose without obvious dose-dependent effect Otherthan that in vivo tests in rats induced by alloxan revealed
that stachyose extract at the dose of 200mgkg significantlydecreased blood-sugar level [15]
Diboside A lapathosides C and D vanicosides A andB and hydropiperoside were isolated from the FagopyrumPolygonum and Persicaria genera belonging to the Polygo-naceae family Diboside A (116) could potentially inhibit 120572-amylase activity with an IC
50of 269 120583M and thus retard the
starch digestion rate which is helpful for diabetic individualsin controlling blood sugar level [107] Lapathoside D (38)exerted stronger activity of 120572-glucosidase inhibition with anIC50
value of 0113mM than acarbose which was chosen asa positive drug for the treatment of type II diabetes [43]Vanicoside B (111) was reported to have higher 120573-glucosidaseinhibitory activity with an IC
50of 505 120583M than vanicoside A
(110) with an IC50of 599 120583M because of the acetyl moiety of
the latter possibly decreasing inhibitory activity of vanicosideA [71]
Fujimoto et al investigated the inhibitory effects ofmumeoses FndashO (83ndash92) from the Prunus genus on aldosereductase and discovered that caffeoyl groups are crucialfor the inhibitory effect on aldose reductase And thusmumeoses F G H J K L M and N (IC
50= 22ndash77120583M) with
a coumaroyl group and acetyl groups inhibited moderatelyaldose reductase from reducing glucose to sorbitol whichis associated with the chronic complications of diabetes [6364]
37 Elicitors and Regulators Oligosaccharides are quitepropitious for encoding biological information because ofdiverse monosaccharide units and complex molecular struc-tures and they are therefore first described as biological
18 Evidence-Based Complementary and Alternative Medicine
181 H
H
H
H
H
H
H
H
H H
H
H
H
H
H
H
H H
HH
Benzyl
Benzyl
Benzyl
182
183
184 Ac
Ac
Ac
Ac
Ac
Ac
Ac
Ac
Ac
Ac
185
186
187
188
189
R1 R2 R3
R1 R2 R3 R4
OCH3
R3OH2C OR2
OR1
OR1
O
O
O
O O
OOO
O
OO
O
OH
OH
OH OH
OH
O O
O
O
OH
HO
OH
OH OHOH
OH
OH
OHHO
HO
OH
OH
HO
CH2OH
CH2OH
CH2OH
CH2OH
C
R2O
R3O
CH2OR4
CH2CH2 CH2CH2CH2CH2CH3
CH3
CH3
191190 192
193
O
C C
O
OO
OO
OO
OO
O O
O
O
O
O
O
O
OH
OH
OHHO
HO
HOOH
OH
OH
OH
HO
OH
OH
OH
OH
HO
HO
C C
R998400O
R998400
Figure 6
signals in plants [108] Oligosaccharides from the cell wallfragments of plants and fungi are powerful signal moleculessuch as the elicitors of plant defence response and theregulators of plant growth and they are capable of exertingbiological activities at exceedingly low concentrations [109]Heptasaccharide (HS) (15) and octasaccharide (OS) (16) iso-lated from the Paris genus possessed plant growth-regulatory
activities [29 30]The two oligosaccharides significantly pro-moted the proliferation of Paris polyphylla var yunnanensisroots at the doses of 25ndash20mgL The octasaccharide hadthe most obvious effect on the growth of Panax japonicusvar major hairy roots at a dose of 30mgL while the otherhad the most positive effect on saponin accumulation ofPanax japonicus var major hairy roots at a dose of 10mgL
Evidence-Based Complementary and Alternative Medicine 19
[29] Similarly Zhou et al evaluated the stimulating effectsof HS and OS on the root growth and saponin productionof Panax ginseng hairy roots which were induced from theplant roots infected withAgrobacterium rhizogenes strain A4The results showed that there was a maximum effect on thehairy roots growth and saponin accumulation on day 10Compared with control group the root biomass dry weightwas increased by more than 17-fold while the total saponincontent of roots increased by more than 1-fold when thesetwo oligosaccharides were added to the hairy root at a dose of30mgL [30] The above data illustrate that HS and OS couldserve as the plant growth-regulators not only in their originalspecies but also in others
38 Immunopotentiating Activity Macrophages are impor-tant targets of investigations on cytophagy cellular immunityand molecular immunology Therefore they are deemedto play a vital role in host defense comprising phagocy-tosis proteolytic processing pathogenic agent apoptosiscytokines production and foreign antigens presentation[110] The water-extracted oligosaccharides from Panax gin-seng (WGOS) exhibited better immunopotentiating activ-ity by increasing phagocytic function of macrophages andpromoting NO TNF-120572 and reactive oxygen species pro-duction [110] In addition Wan et al have obtained malto-oligosaccharides (17 119899 = 3sim8) and three oligosaccharides (213 14) from the Panax ginseng roots The in vitro bioassaypointed out thatWGOS could serve as efficacious stimulatorsof B and T lymphocytes [28] These studies provided enlight-enment that the mixture of oligosaccharides from Chineseherbalmedicine exhibits significant effect on immune system
39 Others Acetylcholinesterase (AChE) inhibitors showgood therapeutic effects onmyasthenia gravis glaucoma andAlzheimerrsquos disease through reversible enzyme inhibitionso as to increase the accumulation of acetylcholine in thesynapse and then promote and prolong the function ofacetylcholine Vanicoside B (111) showed AChE inhibitoryactivity with an IC
50of 0062mM while hydropiperoside
(42) and lapathosides C (115) and D (38) just exhibited weakenzyme inhibitory activity [43]
Wang et al has explored low molecular mass carbohy-drate polymer from Panax ginseng roots and obtained 30ethanol elution (PGO)which included peptides and oligosac-charides (17 119899 = 0sim5) identified as maltose maltotriosemaltotetraose maltopentaose maltohexaose and maltohep-taose Pharmacological experiments revealed that PGO couldsignificantly enhance the memory in scopolamine-inducedmemory deficit rats [27]
Cistanoside F (129) and kankanose (150) were isolatedfrom the Cistanche Paulownia and Acanthus genera Phar-macological experiments showed that cistanoside F andkankanose significantly exhibited vasorelaxant effects on thenoradrenaline-induced contraction of thoracic aorta fromrats [80]
4 Conclusion
Traditional Chinese medicine from natural kingdom playsan indelible role in the treatment of human diseases andit has aroused the attention of those who have engagedin medicinal pharmaceutical chemistry Therefore scientistshave made great contributions day after day to investigate thevalid chemicals from traditional Chinese medicines In thepast decades about 193 oligosaccharides and their esters havebeen identified from traditional Chinese medicinal plantsOn the one hand only a few oligosaccharides and theirmixtures were investigated and just exhibited antidepres-sant antineoplastic antidiabetic plant growth-regulatoryimmunopotentiating and enhancedmemory activitiesMoreexploratory work is still needed to excavate biological andpharmacological activities of oligosaccharides On the otherhand oligosaccharide esters exhibited multi-advantageousactivities Bioassays have revealed that antioxidant cytotoxicantineoplastic and anti-inflammatory activities are the mostnotable bioactivities Of course to search for the naturalproducts with these activities is a hotpot in the contemporarydrug research Oligosaccharide esters provide a vast treasuretrove for medical researchers After considering the currentstudies it should be taken as future directions to makemore mechanism of action studies and clinical trials tofurther evaluate its potential as new drugs Moreover thestructure-activity relationships discussed in this review willprovide reference information for further exploring theirrelationships and continually discovering the new bioactiveoligosaccharide esters
Conflict of Interests
The authors declare that there is no conflict of interestsregarding the publication of this paper
References
[1] X D Yang L J Zhang B Liang L Z Xu and S L YangldquoOligosaccharide esters isolated from plants of PolygalaceaerdquoChinese Traditional and Herbal Drugs vol 33 no 10 pp 954ndash958 2002
[2] N Ogwuru and M Adamczeski ldquoBioactive natural productsderived from Polygonum species of plants their structures andmechanisms of actionrdquo Studies in Natural Products Chemistryvol 22 pp 607ndash642 2000
[3] S Kobayashi T Miyase and H Noguchi ldquoPolyphenolic glyco-sides and oligosaccharide multiesters from the roots of Polygaladalmaisianardquo Journal of Natural Products vol 65 no 3 pp 319ndash328 2002
[4] M Takasaki S Kuroki M Kozuka and T Konoshima ldquoNewphenylpropanoid esters of sucrose from Polygonum lapathi-foliumrdquo Journal of Natural Products vol 64 no 10 pp 1305ndash1308 2001
[5] M L Zimmermann and A T Sneden ldquoVanicosides A and Bprotein kinase C inhibitors from Polygonum pensylvanicumrdquoJournal of Natural Products vol 57 no 2 pp 236ndash242 1994
[6] M Takasaki T Konoshima S Kuroki H Tokuda and HNishino ldquoCancer chemopreventive activity of phenylpropanoid
20 Evidence-Based Complementary and Alternative Medicine
esters of sucrose vanicoside B and lapathoside A from Poly-gonum lapathifoliumrdquo Cancer Letters vol 173 no 2 pp 133ndash138 2001
[7] Q Fu T Liang Z Y Li et al ldquoSeparation of carbohydrates usinghydrophilic interaction liquid chromatographyrdquo CarbohydrateResearch vol 379 pp 13ndash17 2013
[8] M F Mrozek D Zhang and D Ben-Amotz ldquoOligosaccharideidentification and mixture quantification using Raman spec-troscopy and chemometric analysisrdquo Carbohydrate Researchvol 339 no 1 pp 141ndash145 2004
[9] G S Armstrong and B Bendiak ldquoHigh-resolution four-dimen-sional carbon-correlated 1H-1H ROESY experiments employ-ing isotags and the filter diagonalization method for effectiveassignment of glycosidic linkages in oligosaccharidesrdquo Journalof Magnetic Resonance vol 181 no 1 pp 79ndash88 2006
[10] G S Armstrong V A Mandelshtam A J Shaka and BBendiak ldquoRapid high-resolution four-dimensional NMR spec-troscopy using the filter diagonalization method and its advan-tages for detailed structural elucidation of oligosaccharidesrdquoJournal of Magnetic Resonance vol 173 no 1 pp 160ndash168 2005
[11] H-M Tseng S Gattolin J Pritchard H J Newbury and DA Barrett ldquoAnalysis of mono- di- and oligosaccharides by CEusing a two-stage derivatization method and LIF detectionrdquoElectrophoresis vol 30 no 8 pp 1399ndash1405 2009
[12] N Li X Li B L Hou and D L Meng ldquoNew disaccharosidefrom Camptosorus sibiricus Ruprrdquo Natural Product Researchvol 22 no 15 pp 1379ndash1383 2008
[13] Z Zhang D Wang Y Zhao H Gao Y-H Hu and J-FHu ldquoFructose-derived carbohydrates from Alisma orientalisrdquoNatural Product Research vol 23 no 11 pp 1013ndash1020 2009
[14] X Yang Y Zhao N He and K D Croft ldquoIsolation char-acterization and immunological effects of 120572-galacto-oligo-saccharides from a new source the herb Lycopus lucidus TurczrdquoJournal of Agricultural and Food Chemistry vol 58 no 14 pp8253ndash8258 2010
[15] R X Zhang Z P Jia L Y Kong et al ldquoStachyose extractfrom Rehmannia glutinosa Libosch to lower plasma glucose innormal and diabetic rats by oral administrationrdquo Pharmazievol 59 no 7 pp 552ndash556 2004
[16] R Zhang Y Zhao Y Sun X Lu and X Yang ldquoIsolationcharacterization and hepatoprotective effects of the raffinosefamily oligosaccharides from Rehmannia glutinosa liboschrdquoJournal of Agricultural and Food Chemistry vol 61 no 32 pp7786ndash7793 2013
[17] H Li F Song Z Zheng Z Liu and S Liu ldquoCharacterization ofsaccharides and phenolic acids in the Chinese herb Tanshen byESI-FT-ICR-MS and HPLCrdquo Journal of Mass Spectrometry vol43 no 11 pp 1545ndash1552 2008
[18] J E Deng J Zhang XM ChenW Ke and G Y Tian ldquoStudieson the physicochemical properties structure and antitumoractivity of an oligosaccharide homologue SnS-2 from the root ofScrophularia ningpoensis Hemslrdquo Chinese Journal of Chemistryvol 22 no 5 pp 492ndash497 2004
[19] S C Chou LM Chuang and S S Lee ldquoHypoglycemic constit-uents of gynura divaricata subsp formosanardquo Natural ProductCommunications vol 7 no 2 pp 221ndash222 2012
[20] F Feng L-L Wang X-P Lai Y-B Li Z-M Cao and Y-J Zhou ldquoStudy on oligosaccharides from Morinda officinalisrdquoJournal of Chinese Medicinal Materials vol 35 no 8 pp 1259ndash1262 2012
[21] Y F Li Z H Gong M Yang Y M Zhao and Z P Luo ldquoInhibi-tion of the oligosaccharides extracted fromMorinda officinalis
a Chinese traditional herbal medicine on the corticosteroneinduced apoptosis in PC12 cellsrdquo Life Sciences vol 72 no 8 pp933ndash942 2003
[22] Y-F Li Y-Q Liu M Yang et al ldquoThe cytoprotective effect ofinulin-type hexasaccharide extracted from Morinda officinalison PC12 cells against the lesion induced by corticosteronerdquo LifeSciences vol 75 no 13 pp 1531ndash1538 2004
[23] D N Olennikov L M Tankhaeva and A V Rokhin ldquoGlu-cofructans from Saussurea lappa rootsrdquo Chemistry of NaturalCompounds vol 47 no 3 pp 339ndash342 2011
[24] S K Hyun H A Jung B S Min J H Jung and J S ChoildquoIsolation of phenolics nucleosides saccharides and an alkaloidfrom the root of Aralia cordatardquo Natural Product Sciences vol16 no 1 pp 20ndash25 2010
[25] Z J Xu C W Lin and M F Liao ldquoStructure analysis of a newoligosaccharides BROS from Blumea ripariardquo Chinese Journalof Organic Chemistry vol 31 no 11 pp 1811ndash1819 2011
[26] Z J Xu C W Lin and Y Shi ldquoIsolation and structuredetermination of a new oligosaccharide from Blume ripariardquoJournal of Medicinal Plants Research vol 5 no 14 pp 2956ndash2962 2011
[27] Y Wang R Z Jiang G R Li et al ldquoStructural and enhancedmemory activity studies of extracts from Panax ginseng rootrdquoFood Chemistry vol 119 no 3 pp 969ndash973 2010
[28] DWan L Jiao H Yang and S Liu ldquoStructural characterizationand immunological activities of the water-soluble oligosaccha-rides isolated from thePanax ginseng rootsrdquoPlanta vol 235 no6 pp 1289ndash1297 2012
[29] L G Zhou C Z Yang J Q Li S L Wang and J Y WuldquoHeptasaccharide and octasaccharide isolated from Paris pol-yphylla var yunnanensis and their plant growth-regulatoryactivityrdquo Plant Science vol 165 no 3 pp 571ndash575 2003
[30] L G Zhou X D Cao R F Zhang Y L Peng S J Zhao andJ Y Wu ldquoStimulation of saponin production in Panax ginsenghairy roots by two oligosaccharides from Paris polyphylla varyunnanensisrdquo Biotechnology Letters vol 29 no 4 pp 631ndash6342007
[31] M Vanhaecke W van den Ende E Lescrinier and N Dyu-bankova ldquoIsolation and characterization of a pentasaccharidefrom Stellaria mediardquo Journal of Natural Products vol 71 no 11pp 1833ndash1836 2008
[32] J Feng and W Zhao ldquoComplete 1Hand 13C NMR assignmentsof four new oligosaccharides and two new glycosides fromPeriploca forrestiirdquoMagnetic Resonance in Chemistry vol 47 no8 pp 701ndash705 2009
[33] J Q Feng R J Zhang Y Zhou et al ldquoImmunosuppressive preg-nane glycosides from Periploca sepium and Periploca forrestiirdquoPhytochemistry vol 69 no 15 pp 2716ndash2723 2008
[34] X H Long R Xu Y H Zhang X H Tan andQ Y Sun ldquoA newoligosaccharide from Periploca calophyllardquo Zhongguo ZhongyaoZazhi vol 37 no 2 pp 226ndash229 2012
[35] L Wang Z-Q Yin Y Wang X-Q Zhang Y-L Li and W-CYe ldquoPerisesaccharides A-E new oligosaccharides from the rootbarks ofPeriploca sepiumrdquoPlantaMedica vol 76 no 9 pp 909ndash915 2010
[36] T Lei L Zhang H-Y Jiang Y Hu A-H Hong and Y-Z CenldquoA new pregnane glycoside and oligosaccharide from Parabar-ium huaitingiirdquo Journal of Asian Natural Products Research vol13 no 11 pp 1030ndash1035 2011
[37] J Li Y Jiang and P F Tu ldquoTricornoses A-L oligosaccharidemulti-esters from the roots of Polygala tricornisrdquo Journal ofNatural Products vol 68 no 5 pp 739ndash744 2005
Evidence-Based Complementary and Alternative Medicine 21
[38] H H Tu P Liu L Mu et al ldquoStudy on antidepressant com-ponents of sucrose ester from Polygala tenuifoliardquo ZhongguoZhongyao Zazhi vol 33 no 11 pp 1278ndash1280 2008
[39] G M She Y Y Ba Y Liu H Lv W Wang and R B ShildquoAbsorbable phenylpropenoyl sucroses from Polygala tenuifo-liardquoMolecules vol 16 no 7 pp 5507ndash5513 2011
[40] J Yong and P F Tu ldquoStudies on the chemical constituents inroot bark of Polygala tenuifolia (II)rdquo China Journal of ChineseMateria Medica vol 29 no 8 pp 751ndash753 2004
[41] M Ono C Takamura F Sugita et al ldquoTwo new steroidglycosides and a new sesquiterpenoid glycoside from theunderground parts of Trillium kamtschaticumrdquo Chemical andPharmaceutical Bulletin vol 55 no 4 pp 551ndash556 2007
[42] Y Ling Z Li M Chen Z Sun M Fan and C HuangldquoAnalysis and detection of the chemical constituents of RadixPolygalae and their metabolites in rats after oral administrationby ultra high-performance liquid chromatography coupledwith electrospray ionization quadrupole time-of-flight tandemmass spectrometryrdquo Journal of Pharmaceutical and BiomedicalAnalysis vol 85 pp 1ndash13 2013
[43] P Fan L Terrier A-E Hay A Marston and K HostettmannldquoAntioxidant and enzyme inhibition activities and chemicalprofiles ofPolygonum sachalinensis FSchmidt exMaxim (Polyg-onaceae)rdquo Fitoterapia vol 81 no 2 pp 124ndash131 2010
[44] L J Zhang C C Liao H C Huang Y C Shen L M Yangand Y H Kuo ldquoAntioxidant phenylpropanoid glycosides fromSmilax bracteatardquo Phytochemistry vol 69 no 6 pp 1398ndash14042008
[45] L L Yan W Y Gao Y J Zhang and Y Wang ldquoA new phenyl-propanoid glycosides from Paris polyphylla var yunnanensisrdquoFitoterapia vol 79 no 4 pp 306ndash307 2008
[46] Y H Kuo Y W Hsu C C Liaw J K Lee H C Huang andL M Y Kuo ldquoCytotoxic phenylpropanoid glycosides from thestems of Smilax chinardquo Journal of Natural Products vol 68 no10 pp 1475ndash1478 2005
[47] W-X Wang T-X Li H Ma J-F Zhang and A-Q JialdquoTumoral cytotoxic and antioxidative phenylpropanoid glyco-sides in Smilax riparia A DCrdquo Journal of Ethnopharmacologyvol 149 no 2 pp 527ndash532 2013
[48] N X Nhiem P vanKiem C vanMinh et al ldquoPhenylpropanoidglycosides fromHeterosmilax erythrantha and their antioxidantactivityrdquo Archives of Pharmacal Research vol 32 no 10 pp1373ndash1377 2009
[49] Y Wang W Y Gao T J Zhang and Y Q Guo ldquoA novelphenylpropanoid glycosides and a new derivation of phenolicglycoside from Paris Polyphylla var yunnanensisrdquo ChineseChemical Letters vol 18 no 5 pp 548ndash550 2007
[50] J-Y Zhang Y-Z Wang Y-L Zhao et al ldquoPhytochemicals andbioactivities of Paris speciesrdquo Journal of Asian Natural ProductsResearch vol 13 no 7 pp 670ndash681 2011
[51] N H N Hashim F Abas K Shaari and N H Lajis ldquoLC-DAD-ESIMSMS characterization of antioxidant and anti-cholinesterase constituents present in the active fraction fromPersicaria hydropiperrdquo LWT Food Science and Technology vol46 no 2 pp 468ndash476 2012
[52] PH FanA EHayAMarstonHX Lou andKHostettmannldquoChemical variability of the invasive neophytes Polygonumcuspidatum Sieb and Zucc and Polygonum sachalinensis FSchmidt ex Maximrdquo Biochemical Systematics and Ecology vol37 no 1 pp 24ndash34 2009
[53] P Liu Y Hu D H Guo et al ldquoPotential antidepressantproperties of Radix Polygalae (Yuan Zhi)rdquo Phytomedicine vol17 no 10 pp 794ndash799 2010
[54] J F Wu S B Chen S L Chen and P F Tu ldquoThe chemical con-stituents of Polygala hongkongensisHemslrdquoActa PharmaceuticaSinica vol 42 no 7 pp 757ndash761 2007
[55] Y Song Y Jiang D Bi X Tian L Liang and P Tu ldquoChemicalconstituents from n-butanol extract of aerial part of Polygalasibiricardquo Zhongguo Zhongyao Zazhi vol 37 no 4 pp 471ndash4742012
[56] Y Ikeya S Takeda M Tunakawa et al ldquoCognitive improvingand cerebral protective effects of acylated oligosaccharides inPolygala tenuifoliardquo Biological and Pharmaceutical Bulletin vol27 no 7 pp 1081ndash1085 2004
[57] C J Zheng C L Hu X Q Ma C Peng H Zhang and L PQin ldquoCytotoxic phenylpropanoid glycosides from Fagopyrumtataricum (L) Gaertnrdquo Food Chemistry vol 132 no 1 pp 433ndash438 2012
[58] X Li Y F Zhang L Yang et al ldquoChemical profiling ofconstituents of Smilacis glabrae using ultra-high pressure liquidchromatography coupled with LTQ orbitrap mass spectrome-tryrdquo Natural Product Communications vol 7 no 2 pp 181ndash1842012
[59] T-T Sun D-W Zhang Y Han F-Y Dong andWWang ldquoSmi-lasides M and N two new phenylpropanoid glycosides fromSmilax ripariardquo Journal of Asian Natural Products Research vol14 no 2 pp 165ndash170 2012
[60] J Li X Bi G Zheng Y Hitoshi T Ikeda and T NoharaldquoSteroidal glycosides and aromatic compounds from Smilaxripariardquo Chemical amp Pharmaceutical Bulletin vol 54 no 10 pp1451ndash1454 2006
[61] N Wang X Yao R Ishii and S Kitanaka ldquoBioactive sucroseesters from Bidens parviflorardquo Phytochemistry vol 62 no 5 pp741ndash746 2003
[62] S Nakamura K Fujimoto T Matsumoto et al ldquoAcylatedsucroses and acylated quinic acids analogs from the flower budsof Prunus mume and their inhibitory effect on melanogenesisrdquoPhytochemistry vol 92 pp 128ndash136 2013
[63] K Fujimoto SNakamura TMatsumoto et al ldquoMedicinal flow-ers XXXVIII Structures of acylated sucroses and inhibitoryeffects of constituents on aldose reducatase from the flower budsofPrunusmumerdquoChemical and Pharmaceutical Bulletin vol 61no 4 pp 445ndash451 2013
[64] S Nakamura K Fujimoto T Matsumoto et al ldquoStructuresof acylated sucroses and an acylated flavonol glycoside andinhibitory effects of constituents on aldose reductase from theflower buds of Prunus mumerdquo Journal of Natural Medicines vol67 no 4 pp 799ndash806 2013
[65] L-B Dong J He X-Y Li et al ldquoChemical constituents fromthe aerial parts of Musella lasiocarpardquo Natural Products andBioprospecting vol 1 no 1 pp 41ndash47 2011
[66] Y Xiong K Z Deng Y Q Guo W Y Gao and T J ZhangldquoNew chemical constituents from the rhizomes of Sparganiumstoloniferumrdquo Archives of Pharmacal Research vol 32 no 5 pp717ndash720 2009
[67] Y Xiong K-Z Deng Y-Q Guo W-Y Gao and T-J ZhangldquoTwo new sucrose esters from Sparganium stoloniferumrdquo Jour-nal of Asian Natural Products Research vol 10 no 5 pp 425ndash428 2008
[68] B Chen N L Wang J H Huang and X S Yao ldquoIridoidand phenylpropanoid glycosides from Scrophularia ningpoensis
22 Evidence-Based Complementary and Alternative Medicine
Hemslrdquo Asian Journal of Traditional Medicines vol 2 no 3 pp119ndash123 2007
[69] H Chen Y Z Zhou L Qiao et al ldquoTwo new compounds fromCynanchum amplexicaulerdquo Journal of Asian Natural ProductsResearch vol 10 no 3 pp 248ndash251 2008
[70] C-L Chang L-J Zhang R Y Chen et al ldquoAntioxidant andanti-inflammatory phenylpropanoid derivatives from Calamusquiquesetinerviusrdquo Journal of Natural Products vol 73 no 9 pp1482ndash1488 2010
[71] Y Kawai H Kumagai H Kurihara K Yamazaki R Sawanoand N Inoue ldquo120573-Glucosidase inhibitory activities of phenyl-propanoid glycosides vanicoside A and B from Polygonumsachalinense rhizomerdquo Fitoterapia vol 77 no 6 pp 456ndash4592006
[72] P V Kiem N X Nhiem N X Cuong et al ldquoNew phenyl-propanoid esters of sucrose from Polygonum hydropiper andtheir antioxidant activityrdquo Archives of Pharmacal Research vol31 no 11 pp 1477ndash1482 2008
[73] K J Wang Y J Zhang and C R Yang ldquoAntioxidant phenolicconstituents from Fagopyrum dibotrysrdquo Journal of Ethnophar-macology vol 99 no 2 pp 259ndash264 2005
[74] N Cho J Huh H Yang et al ldquoChemical constituentsof Polygala tenuifolia roots and their inhibitory activity onlipopolysaccharide-induced nitric oxide production in BV2microgliardquo Journal of Enzyme Inhibition and Medicinal Chem-istry vol 27 no 1 pp 1ndash4 2012
[75] Q Ren C S Wu and J L Zhang ldquoUse of on-line stop-flowheart-cutting two-dimensional high performance liquid chro-matography for simultaneous determination of 12 major con-stituents in tartary buckwheat (Fagopyrum tataricum Gaertn)rdquoJournal of Chromatography A vol 1304 pp 257ndash262 2013
[76] Q Ren C S Wu Y Ren and J L Zhang ldquoCharacterizationand identification of the chemical constituents from tartarybuckwheat (Fagopyrum tataricumGaertn) by high performanceliquid chromatographyphotodiode array detectorlinear iontrap FTICR hybrid mass spectrometryrdquo Food Chemistry vol136 no 3-4 pp 1377ndash1389 2013
[77] W Li Y N Sun X T Yan et al ldquoNF-120581B inhibitory activityof sucrose fatty acid esters and related constituents fromAstragalus membranaceusrdquo Journal of Agricultural and FoodChemistry vol 61 no 29 pp 7081ndash7088 2013
[78] J T Cheng J He Y Li et al ldquoThree new sucrose fatty acid estersfrom Equisetum hiemale LrdquoHelvetica Chimica Acta vol 95 no7 pp 1158ndash1163 2012
[79] Y Jiang and P-F Tu ldquoTenuifoliose Q a new oligosaccharideester from the root of Polygala tenuifoliaWilldrdquo Journal of AsianNatural Products Research vol 5 no 4 pp 279ndash283 2003
[80] M Yoshikawa H Matsuda T Morikawa H H Xie S Naka-mura and O Muraoka ldquoPhenylethanoid oligoglycosides andacylated oligosugars with vasorelaxant activity from Cistanchetubulosardquo Bioorganic ampMedicinal Chemistry vol 14 no 22 pp7468ndash7475 2006
[81] P-F Tu H-M Shi Z-H Song Y Jiang and Y-Y ZhaoldquoChemical constituents of Cistanche sinensisrdquo Journal of AsianNatural Products Research vol 9 no 1 pp 79ndash84 2007
[82] C-L Si Y-Y Lu P-P Qin R-C Sun and Y-H Ni ldquoPhenolicextractives with chemotaxonomic significance from the bark ofPaulownia tomentosa var tomentosardquo BioResources vol 6 no4 pp 5086ndash5098 2011
[83] J Wu S Zhang Q Xiao et al ldquoPhenylethanoid and aliphaticalcohol glycosides from Acanthus ilicifoliusrdquo Phytochemistryvol 63 no 4 pp 491ndash495 2003
[84] Y Jiang and P-F Tu ldquoAnalysis of chemical constituents inCistanche speciesrdquo Journal of Chromatography A vol 1216 no11 pp 1970ndash1979 2009
[85] H Otsuka H Kuwabara and H Hoshiyama ldquoIdentification ofsucrose diesters of aryldihydronaphthalene-type lignans fromTrigonotis peduncularisand the nature of their fluorescencerdquoJournal of Natural Products vol 71 no 7 pp 1178ndash1181 2008
[86] M-R Suo J-S Yang and Q-H Liu ldquoLignan oligosaccharideesters from Eritrichium rupestrerdquo Journal of Natural Productsvol 69 no 4 pp 682ndash684 2006
[87] P-F Tu Z-H Song H-M Shi Y Jiang and Y-Y ZhaoldquoArylethyl (=phenylethanoid) glycosides and oligosaccharidefrom the stem of Cistanche tubulosardquo Helvetica Chimica Actavol 89 no 5 pp 927ndash935 2006
[88] M-H Shyr T-H Tsai and L-C Lin ldquoRossicasins A Band rosicaside F three new phenylpropanoid glycosides fromBoschniakia rossicardquoChemical and Pharmaceutical Bulletin vol54 no 2 pp 252ndash254 2006
[89] R FangNCVeitchGCKiteM J RHowes EA Porter andM S J Simmonds ldquoGlycosylated constituents of Iris fulvaandIris brevicaulisrdquoChemical amp Pharmaceutical Bulletin vol 59 no1 pp 124ndash128 2011
[90] J Fu L Zuo J Yang R Chen and D Zhang ldquoOligosaccharidepolyester and triterpenoid saponins from the roots of Polygalajaponicardquo Phytochemistry vol 69 no 7 pp 1617ndash1624 2008
[91] M-C Cheng C-Y Li H-C Ko F-N Ko Y-L Lin andT-S Wu ldquoAntidepressant principles of the roots of polygalatenuifoliardquo Journal of Natural Products vol 69 no 9 pp 1305ndash1309 2006
[92] H T Chang and P F Tu ldquoNew oligosaccharide esters andxanthone C-glucosides from Polygala telephioidesrdquo HelveticaChimica Acta vol 90 no 5 pp 944ndash950 2007
[93] J Li L Feng J Dai R Wang and T Nohara ldquoChemical con-stituents from Polygala telephioidesrdquo China Journal of ChineseMateria Medica vol 34 no 4 pp 402ndash405 2009
[94] W-P Yin T-Z Zhao and H-Y Zhang ldquoA novel oligosaccha-ride ester from Syringa pubescensrdquo Journal of Asian NaturalProducts Research vol 10 no 1 pp 95ndash100 2008
[95] M Valko D Leibfritz J Moncol M T D Cronin M Mazurand J Telser ldquoFree radicals and antioxidants in normal physio-logical functions and human diseaserdquoThe International Journalof Biochemistry amp Cell Biology vol 39 no 1 pp 44ndash84 2007
[96] D Krishnaiah R Sarbatly and R Nithyanandam ldquoA review ofthe antioxidant potential of medicinal plant speciesrdquo Food andBioproducts Processing vol 89 no 3 pp 217ndash233 2011
[97] P Liu Y Hu D-H Guo et al ldquoAntioxidant activity ofoligosaccharide ester extracted from Polygala tenuifolia roots insenescence-accelerated micerdquo Pharmaceutical Biology vol 48no 7 pp 828ndash833 2010
[98] Y Hu H-B Liao G Dai-Hong P Liu Y-Y Wang and KRahman ldquoAntidepressant-like effects of 361015840-disinapoyl sucroseon hippocampal neuronal plasticity and neurotrophic signalpathway in chronically mild stressed ratsrdquo NeurochemistryInternational vol 56 no 3 pp 461ndash465 2010
[99] Y Hu H B O Liao P Liu D-H Guo and K RahmanldquoA bioactive compound from Polygala tenuifolia regulatesefficiency of chronic stress on hypothalamic-pituitary-adrenalaxisrdquo Pharmazie vol 64 no 9 pp 605ndash608 2009
[100] A Jungbauer and SMedjakovic ldquoAnti-inflammatory propertiesof culinary herbs and spices that ameliorate the effects ofmetabolic syndromerdquoMaturitas vol 71 no 3 pp 227ndash239 2012
Evidence-Based Complementary and Alternative Medicine 23
[101] Q Xu Y Wang S Guo Z Shen and L Yang ldquoAnti-inflammatory and analgesic activity of aqueous extract of Flospopulirdquo Journal of Ethnopharmacology vol 152 no 3 pp 540ndash545 2014
[102] K S Kim D S Lee G S Bae et al ldquoThe inhibition of JNKMAPK and NF-120581B signaling by tenuifoliside A isolated fromPolygala tenuifolia in lipopolysaccharide-induced macrophagesis associated with its anti-inflammatory effectrdquo European Jour-nal of Pharmacology vol 721 no 1ndash3 pp 267ndash276 2013
[103] J-G Lee J-M Yon C Lin A Y Jung K Y Jung and S-YNamldquoCombined treatment with capsaicin and resveratrol enhancesneuroprotection against glutamate-induced toxicity in mousecerebral cortical neuronsrdquo Food and Chemical Toxicology vol50 no 11 pp 3877ndash3885 2012
[104] M L Jin S Y Park Y H Kim J-I Oh S J Lee andG Park ldquoThe neuroprotective effects of cordycepin inhibitglutamate-induced oxidative andER stress-associated apoptosisin hippocampal HT22 cellsrdquo NeuroToxicology vol 41 pp 102ndash111 2014
[105] P Liu Y Hu J Li et al ldquoProtection of SH-SY5Y neuronal cellsfrom glutamate-induced apoptosis by 36rsquo-disinapoyl sucrosea bioactive compound isolated from radix polygalardquo Journal ofBiomedicine and Biotechnology vol 2012 Article ID 728342 5pages 2012
[106] P-B Li W-L Lin Y-G Wang W Peng X-Y Cai and W-WSu ldquoAntidiabetic activities of oligosaccharides of Ophiopogonisjaponicus in experimental type 2 diabetic ratsrdquo InternationalJournal of Biological Macromolecules vol 51 no 5 pp 749ndash7552012
[107] T Liu Y M Yip L Song et al ldquoInhibiting enzymatic starchdigestion by the phenolic compound diboside A a mechanisticand in silico studyrdquo Food Research International vol 54 no 1pp 595ndash600 2013
[108] F Cote andMGHahn ldquoOligosaccharins structures and signaltransductionrdquo Plant Molecular Biology vol 26 no 5 pp 1379ndash1411 1994
[109] RACreelman and J EMullet ldquoOligosaccharins brassinolidesand jasmonates nontraditional regulators of plant growthdevelopment and gene expressionrdquo Plant Cell vol 9 no 7 pp1211ndash1223 1997
[110] L Jiao D Wan X Zhang B Li H Zhao and S LiuldquoCharacterization and immunostimulating effects on murineperitoneal macrophages of oligosaccharide isolated from Panaxginseng CAMeyerrdquo Journal of Ethnopharmacology vol 144 no3 pp 490ndash496 2012
Submit your manuscripts athttpwwwhindawicom
Stem CellsInternational
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
MEDIATORSINFLAMMATION
of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Behavioural Neurology
EndocrinologyInternational Journal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Disease Markers
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
BioMed Research International
OncologyJournal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
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Oxidative Medicine and Cellular Longevity
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
PPAR Research
The Scientific World JournalHindawi Publishing Corporation httpwwwhindawicom Volume 2014
Immunology ResearchHindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Journal of
ObesityJournal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Computational and Mathematical Methods in Medicine
OphthalmologyJournal of
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Diabetes ResearchJournal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
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Research and TreatmentAIDS
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Gastroenterology Research and Practice
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Parkinsonrsquos Disease
Evidence-Based Complementary and Alternative Medicine
Volume 2014Hindawi Publishing Corporationhttpwwwhindawicom
8 Evidence-Based Complementary and Alternative Medicine
Table2Con
tinued
Num
ber
Nam
eR 1
R 2R 3
R 4R 5
R 6R 7
R 8Source
Parts
Reference
55Sm
ilasid
eEAc
HH
HI
IH
GSm
ilaxbracteata
Smila
xchina
Aeria
lparts
Stem
s[4446
]
56Sm
ilasid
eFAc
HH
AcG
IH
GSm
ilaxchina
Stem
s[46]
57Sm
ilasid
eGH
HH
HG
IH
GSm
ilaxbracteata
Smilacis
glabrae
Aeria
lparts
Rhizom
es[4458]
58Sm
ilasid
eHH
HH
AcG
IH
GSm
ilaxbracteata
Aeria
lparts
[44]
59Sm
ilasid
eIAc
HH
HG
IH
GSm
ilaxbracteata
Aeria
lparts
[44]
60Sm
ilasid
eJH
HH
HG
IH
ISm
ilaxbracteata
Smilacis
glabrae
Aeria
lparts
Rhizom
es[4458]
61Sm
ilasid
eKH
HH
AcI
IH
GSm
ilaxbracteata
Aeria
lparts
[44]
62Sm
ilasid
eLH
HH
HI
IH
ISm
ilaxbracteata
Smilacis
glabrae
Aeria
lparts
Rhizom
es[4458]
63Sm
ilasid
eMAc
HH
AcCis-feruloyl
IH
HSm
ilaxrip
aria
Rootsa
ndrhizom
es[59]
64Sm
ilasid
eNAc
HH
AcI
Cis-
feruloyl
HH
Smila
xrip
aria
Rootsa
ndrhizom
es[59]
65Sm
ilasid
ePH
HH
AcI
IH
ISm
ilaxrip
aria
Rootsa
ndrhizom
es[47]
66310158404101584061015840-O
-Tri-
feruloylsucrose
HH
HH
II
IH
Smila
xrip
aria
Rhizom
esand
roots
[60]
6761015840-O
-Cou
maroylsu
crose
HH
HH
HG
HH
Bidens
parviflora
Who
leplants
[61]
6811015840 -O-C
oumaroyl-61015840-O
-feruloylsucrose
HH
HH
HI
HG
Smila
xbracteata
Aeria
lparts
[44]
694-O-Benzoyl-31015840-345-
trim
etho
xycinn
amoylsu
crose
HD
HH
LH
HH
Polyg
alatricornis
Roots
[37]
706-O-Benzoyl-31015840-O
-345-
trim
etho
xycinn
amoylsu
crose
DH
HH
LH
HH
Polyg
alatricornis
Roots
[37]
716-O-Benzoyl-31015840-O
-sin
apoylsu
crose
DH
HH
KH
HH
Polyg
alatricornis
Roots
[37]
726-O-p-M
etho
xybenzoyl-31015840-O
-345-
trim
etho
xycinn
amoylsu
crose
EH
HH
LH
HH
Polyg
alatenu
ifolia
Roots
[56]
7326-Di-a
cetyl-3101584061015840-di-
feruloylsucrose
AcH
HAc
II
HH
Smila
xchina
Smila
xrip
aria
Heterosmila
xerythrantha
Stem
sRo
otsa
ndrhizom
esAe
rialp
arts
[46ndash
4859]
7426-Di-a
cetyl-31015840-O
-cis-feruloy-
61015840-tr
ans-feruloylsucrose
AcH
HAc
Cis-feruloy
IH
HSm
ilaxrip
aria
Rootsa
ndrhizom
es[59]
Evidence-Based Complementary and Alternative Medicine 9
Table2Con
tinued
Num
ber
Nam
eR 1
R 2R 3
R 4R 5
R 6R 7
R 8Source
Parts
Reference
7526-Di-a
cetyl-31015840-O
-tran
s-feruloy-
61015840-cis-feruloylsucrose
AcH
HAc
ICis-
feruloyl
HH
Smila
xrip
aria
Rootsa
ndrhizom
es[59]
76Re
galosid
eAAc
HH
HI
HH
HTrillium
kamtsc
haticum
Und
ergrou
ndparts
[41]
77Tricorno
seA
AcH
HH
LH
HH
Polyg
alatricornis
Roots
[37]
78Mum
eose
AH
HH
AcG
HH
HPrun
usmum
eFlow
erbu
ds[6263]
79Mum
eose
BAc
HAc
HG
HH
HPrun
usmum
eFlow
erbu
ds[6263]
80Mum
eose
CAc
HAc
AcG
HH
HPrun
usmum
eFlow
erbu
ds[6263]
81Mum
eose
DAc
AcAc
AcG
HH
AcPrun
usmum
eFlow
erbu
ds[6263]
82Mum
eose
EAc
AcAc
AcCis-
coum
aroyl
HH
AcPrun
usmum
eFlow
erbu
ds[6263]
83Mum
eose
FAc
AcAc
HG
HH
HPrun
usmum
eFlow
erbu
ds[63]
84Mum
eose
GAc
HAc
HG
HAc
HPrun
usmum
eFlow
erbu
ds[63]
85Mum
eose
HH
HAc
AcG
HAc
HPrun
usmum
eFlow
erbu
ds[63]
86Mum
eose
IAc
AcAc
HG
AcH
HPrun
usmum
eFlow
erbu
ds[63]
87Mum
eose
JAc
AcAc
AcG
HAc
AcPrun
usmum
eFlow
erbu
ds[63 ]
88Mum
eose
KH
HAc
AcG
HH
HPrun
usmum
eFlow
erbu
ds[64]
89Mum
eose
LAc
HAc
AcG
HAc
HPrun
usmum
eFlow
erbu
ds[64]
90Mum
eose
MAc
AcAc
HG
HAc
AcPrun
usmum
eFlow
erbu
ds[64]
91Mum
eose
NAc
AcAc
HG
AcAc
HPrun
usmum
eFlow
erbu
ds[64]
92Mum
eose
OAc
HAc
AcG
HAc
AcPrun
usmum
eFlow
erbu
ds[64]
9311015840 2346-O-Penta-acetyl-31015840-O
-tra
ns-cou
maroylsu
crose
AcAc
AcAc
GH
HAc
Musellalasio
carpa
Aeria
lparts
[65]
9411015840 2346-O-Penta-acetyl-31015840-O
-cis-cou
maroylsu
crose
AcAc
AcAc
Cis-
coum
aroyl
HH
AcMusellalasio
carpa
Aeria
lparts
[65]
9511015840 236-O-Tetra-acetyl-31015840-O
-cis-
feruloylsucrose
AcH
AcAc
Cis-feruloyl
HH
AcSparganium
stolonifer
umRh
izom
es[66]
9611015840 246-O-Tetra-acetyl-31015840-O
-tra
ns-fe
ruloylsucrose
AcAc
HAc
IH
HAc
Sparganium
stolonifer
umRh
izom
es[66]
9711015840 236-O-Tetra-acetyl-31015840-O
-tra
ns-fe
ruloylsucrose
AcH
AcAc
IH
HAc
Sparganium
stolonifer
umRh
izom
es[67]
98Sibirio
sideA
MH
HH
HH
HH
Scrophularianingpoensis
Roots
[68]
99SibricoseA
1K
HH
HH
HH
HCy
nanchu
mam
plexica
ule
Roots
[69]
100
6-O-C
affeoylsucrose
JH
HH
HH
HH
Scrophularianingpoensis
Roots
[68]
101
Acretosid
eI
HH
HH
HH
HScrophularianingpoensis
Roots
[68]
10 Evidence-Based Complementary and Alternative Medicine
Table2Con
tinued
Num
ber
Nam
eR 1
R 2R 3
R 4R 5
R 6R 7
R 8Source
Parts
Reference
102
Tenu
ifolisideB
FH
HH
KH
HH
Polyg
alatenu
ifolia
Roots
[4256]
103
Tenu
ifolisideC
KH
HH
LH
HH
Polyg
alatricornis
Polyg
alatenu
ifolia
Roots
[374256]
104
Heterosmilasid
eH
HI
HH
IH
HHeterosmila
xerythrantha
Aeria
lparts
[48]
105
Quiqu
esetinerviusideA
HI
HH
II
HH
Calamus
quiquesetin
ervius
Stem
s[70]
106
Quiqu
esetinerviusideB
AcI
HH
II
HH
Calamus
quiquesetin
ervius
Stem
s[70]
107
Quiqu
esetinerviusideC
HI
HAc
II
HH
Calamus
quiquesetin
ervius
Stem
s[70]
108
Quiqu
esetinerviusideD
AcG
HH
II
HH
Calamus
quiquesetin
ervius
Stem
s[70]
109
Quiqu
esetinerviusideE
HG
HAc
II
HH
Calamus
quiquesetin
ervius
Stem
s[70]
110
Vanicosid
eAI
HH
AcG
GH
G
Polyg
onum
sachalinensis
Polyg
onum
cuspidatum
Polyg
onum
hydropiper
Stem
sLeaves
Rhizom
es[51527172]
111
Vanicosid
eBI
HH
HG
GH
G
Polyg
onum
sachalinensis
Polyg
onum
cuspidatum
Persica
riahydropiper
Stem
sLeaves
Rhizom
es[4351527172]
112
Vanicosid
eDG
HH
HG
GH
GPersica
riahydropiper
Leaves
[51]
113
Vanicosid
eEI
AcH
AcG
GH
GPolyg
onum
hydropiper
Stem
sand
leaves
[72]
114
LapathosideA
IH
HH
GG
HI
Polyg
onum
sachalinensis
Polyg
onum
cuspidatum
Fagopyrum
dibotrys
Stem
sRh
izom
es[5173]
115
LapathosideC
IH
HH
GG
HH
Polyg
onum
sachalinensis
Polyg
onum
cuspidatum
Stem
s[4352]
116
DibosideA
GH
HH
GI
HG
Fagopyrum
tataric
umFagopyrum
dibotrys
Roots
Rhizom
es[57]
117
Hidropiperosid
eAI
HH
HH
GH
GPolyg
onum
hydropiper
Stem
sand
leaves
[72]
118
Hidropiperosid
eBI
HH
AcG
GH
IPolyg
onum
hydropiper
Stem
sand
leaves
[72]
119
Tataris
ideB
IH
HAc
GG
HAc
Fagopyrum
tataric
umRo
ots
[57]
Evidence-Based Complementary and Alternative Medicine 11
Table2Con
tinued
Num
ber
Nam
eR 1
R 2R 3
R 4R 5
R 6R 7
R 8Source
Parts
Reference
120
Tataris
ideC
IAc
HAc
GG
HAc
Fagopyrum
tataric
umRo
ots
[57]
121
Tataris
ideD
GH
HAc
GI
HH
Fagopyrum
tataric
umRo
ots
[57]
122
Tataris
ideF
GH
HH
II
HG
Fagopyrum
tataric
umRo
ots
[57]
123
310158406-O
-Di-sinapoylsu
crose
KH
HH
KH
HH
Polyg
alatricornis
Polygalahongkongensis
Polyg
alasib
irica
Polyg
alatenu
ifolia
Cynanchu
mam
plexica
ule
Roots
Root
barks
Who
leplants
Aeria
lparts
[37ndash394153ndash
566974]
124
661015840-O
-Di-c
oumaroylsu
crose
GH
HH
HG
HH
Bidens
parviflora
Who
leplants
[61]
125
11015840 3101584061015840-O
-Tri-
coum
aroyl-6
-feruloylsucrose
IH
HH
GG
HG
Fagopyrum
tataric
umRo
ots
[7576]
126
3101584061015840-O
-Di-c
oumaroyl-110158406-O
-di-
feruloylsucrose
IH
HH
GG
HI
Fagopyrum
tataric
umRo
ots
[7576]
127
31015840-O
-Cou
maroyl-11015840610158406-O
-tri-
feruloylsucrose
IH
HH
IG
HI
Fagopyrum
tataric
umRo
ots
[7576]
128
11015840 31015840610158406-O
-Tetra-fe
ruloylsucrose
IH
HH
II
HI
Fagopyrum
tataric
umRo
ots
[7576]
SeeS
chem
e2
12 Evidence-Based Complementary and Alternative Medicine
131130129
CH2OHOH
OH
OO
OH
C
C
HH
HHO
OO
O
HO
HOHO
HO
HOOH
OHOHOH
OHOH
HOO
O
O
O
HO
HO
OH
OHOHOH
OHOH
HOO
O
O
O
HO
Figure 3
12
3
4
5
6
1998400
2998400
3998400
4998400
5998400
6998400
HO
O
O
R1O
R2O
R8O
R7OOR3
OR4 OR5OR6
Scheme 2
antidepressant cytotoxic antineoplastic anti-inflammatoryantidiabetic plant growth-regulatory neuroprotective andcerebral protective activities Lignan-derived disaccharideesters phenylpropanoid-derived tetrasaccharide esters andpentasaccharide esterswith biological activities have not beenreported Aside from the isolated constituents oligosaccha-ride mixtures from Rehmannia glutinosa Panax ginseng andScrophularia ningpoensiswere also reported to display diversepharmacological activities such as antidiabetic immunopo-tentiating enhanced memory and antineoplastic activitiesThese active compounds and mixtures could serve as thevaluable candidates to be developed as possible drugs for thetreatment and prevention of diseases
31 Antioxidant Activity The adverse effects of oxidativestress proposed to play significant roles in the pathogenesis ofcardiovascular diseases atherosclerosis hypertension can-cer diabetes mellitus neurodegenerative diseases rheuma-toid arthritis ischemiareperfusion injury and ageing havebecome an inevitable and serious issue [95 96] Scientistshave thus made great efforts to explore antioxidants frommedicinal plants by using different kinds of assay methodswhich include DPPH radical scavenging assay hydroxylradical scavenging assay superoxide anion scavenging assayand ABTS radical scavenging method [96]
Lapathosides C and D hydropiperoside vanicoside Bhidropiperosides A and B lapathoside A and diboside Awere isolated from the Polygonum Persicaria and Fagopyrumgenera belonging to the Polygonaceae family The DPPH testrevealed that free radical-scavenging activity of the isolatedcompounds termed lapathoside C (115) hydropiperoside(42) vanicoside B (111) and lapathoside D (38) increasedin turn and lapathoside D exhibited strongest scavengingability with an IC
50of 0088 120583M [43] Hidropiperosides A
and B (117 118) were reported to show obvious antioxidantresponse to DPPH radicals with the SC
50values of 234
and 267 120583gmL respectively while vanicoside E moderatelyexhibited the same activity with a SC
50value of 490 120583gmL
[72] Lapathoside A (114) and diboside A (116) just showedlower antioxidant activities with the SC
50values of 19948 and
16552 120583M respectively [73]Smiglasides A and B smilaside P 26-di-acetyl-3101584061015840-
di-feruloylsucrose helonioside B smilasides GndashL and het-erosmilaside were isolated from the Heterosmilax and Smi-lax genera Compared with ascorbic acid (IC
5014352 120583M)
used as positive control smiglasides A and B and smi-laside P (48 49 65) (IC
5033958 33066 and 31449 120583M
resp) showed higher antioxidant activities than 26-di-acetyl-3101584061015840-di-feruloylsucrose (73) and helonioside B (40) (IC
50
63166 and 51827120583M resp) [47] Additionally Nhiem et alreported that helonioside B heterosmilaside (104) and 26-di-acetyl-3101584061015840-di-feruloylsucrose exhibited important DPPHradical scavenging activities with the SC
50values of 91 127
and 87 120583gmL respectively [48] Compared with smilasidesG-I (57ndash59) (ED
50685ndash794120583M) smilasides JndashL (60ndash62)
showed higher radical scavenging activities with an ED50
value of 267ndash327120583M [44]Five quiquesetinerviusides AndashE (105ndash109) isolated from
the Calamus genus showed weak DPPH scavenging activ-ities (IC
50604ndash1018120583M) but exhibited better hydroxyl
radical scavenging activities (IC50
36ndash84 120583M) Moreoverquiquesetinerviuside C showed superoxide anion scaveng-ing activity with an IC
50value of about 1843 120583M [70]
Liu et al investigated the antioxidant capacity of 310158406-O-di-sinapoylsucrose (DISS) (123) by using the acceleratedsenescence-prone short-lived mice (SAMP) in vivo Theanalyses indicated that the activities of antioxidant enzymesof SOD and glutathione peroxidase ascended obviously inSAMP mice when amended with DISS 50mgkg MoreoverDISS could downregulate and even restore the level ofmalondialdehyde in SAMP model group [97]
From the above studies it can be concluded that oligosac-charide esters with antioxidant activities have been identifiedin the Polygonaceae Liliaceae Smilacaceae and Arecaceaefamilies The results of the antioxidant assays show that theincreased number of phenolic hydroxyl groups and acetylgroups could produce higher antioxidant activity Fan etal indicated that the increased number of phenylpropanoidgroups was not beneficial to free radical scavenging activity[43] Zhang et al pointed out that oligosaccharide esters withferuloyl groups exhibited better antioxidant activities thanthose with coumaroyl groups [44]
Evidence-Based Complementary and Alternative Medicine 13
Table 3 Fatty acid-derived disaccharide esters
Number Name R1 R2 Source Parts Reference132 61015840-O-Linoleylsucrose H O Astragalus membranaceus Roots [77]133 61015840-O-Palmitoylsucrose H P Astragalus membranaceus Roots [77]134 6-O-Palmitoylsucrose P H Astragalus membranaceus Roots [77]
135 61015840-O-Linolenoylsucrose H N Astragalus membranaceusEquisetum hiemale
RootsAerial parts [77 78]
136 6-O-Linoleylsucrose O H Astragalus membranaceus Roots [77]137 6-O-Myristoylsucrose Q H Astragalus membranaceus Roots [77]
138 6-O-[(7Z10Z13Z)-Hexadeca-71013-trienoyl]sucrose H R Equisetum hiemale Aerial parts [78]
139 6-O-[(7Z10Z)-Hexadeca-710-dienoyl]sucrose H S Equisetum hiemale Aerial parts [78]
See Scheme 3
12
3
4
5
6
1998400
2998400
3998400
4998400
5998400
6998400
HO
O
O
R1O
R2O
R8O
R7OOR3
OR4 OR5OR6
O
O
O
18
18
1616
16
14
N linolenoyl
O linoleyl
P palmitoyl
Q myristoyl
O
O
O
R hexadeca-71013-trienoyl
S hexadeca-710-dienoyl
Scheme 3
32 Antidepressant Activity The oligosaccharides obtainedfrom the Morinda genus not only show specific antidepres-sant and antistress activities but also have no suppression orexcitatory effects on central nervous system as well Whatis more they can be taken orally with little toxicity [21]The inulin-type hexasaccharide (IHS) (9) from Morindaofficinalis obviously exhibited cytoprotective activity whichcontributed to the antidepressant effect not only by providingthe PC12 with protection against Cort-induced lesion withIHS 0625 and 125 120583Mbut also by reducing theCort-induced[Ca2+]
119894overloading with IHS 25 and 10 120583M IHS 5 and
10 120583Mupregulated the nerve growth factormRNAexpressionin Cort-induced PC12 cells [22] Polygalatenosides A (181)and B (182) were isolated from the Polygala genus Theysignificantly inhibited the isotope-labeled RTI-55 binding to
norepinephrine transporter protein with the IC50
values of300 and 604 120583M respectively [91]
DISS and tenuifoliside A were isolated from the PolygalaandCynanchum genera Liu et al investigated the antidepres-sant effect of YZ ethanol extract based on the tail suspensiontest (TST) and forced swimming test (FST) which arethe ease-of-use and widely-accepted models for estimatingantidepressant activities in mice The results indicated thatYZ-50 fraction at a dose of 200mgkgwas able to significantlydecrease the immobility time in TST Furthermore YZ-50possessed ability to inhibit corticosterone-induced injury ofhuman neuroblastoma SH-SY5Y cells What is more DISS(123) and tenuifoliside A (44) two major compounds of YZ-50 fraction showed effective protective response to the lesionin SY5Y cells [53] The antidepressant-like effect of DISS at
14 Evidence-Based Complementary and Alternative Medicine
H3CO
HO
HOHO
HO
HO
HO
HOHO
O O
OO O
OO
O
O
O
OO
O
O
OH
OH
OH
OH
OCH3
OCH3
CH2OH
CH2OH
CH2OAc
CH2OAc
H3CO
HOHO
HO
O
O
O
OO
O
O
OH
OH
OH
OCH3
CH2OH
CH2OH
H3CO
H3CO H3CO
HOHO
HO
O
O
O
OO
O
O
OH
OH
OH
OCH3
CH2OH
CH2OAc
CH3O
H
HOHO
HO
HO
HOO O
OO O
OO
OH
OCH3
CH2OHCH2OH
H3CO H3CO
H
CH2CH2 HO
HO
HO
HO
HOO O
OO O
OO
OH
OCH3
CH2OHCH2OAc
H3CO
H
CH2
140 141 142
143 144 145
Figure 4
Table 4 Phenylpropanoid-derived trisaccharide esters
Number Name R1 R2 R3 R4 R5 R6 R7 Source Parts Reference146 Tricornose C K H H H H L H Polygala tricornis Roots [37]147 Tricornose D K H H H H K H Polygala tricornis Roots [37]148 Tricornose E K H H H K L H Polygala tricornis Roots [37]149 Tricornose F K H H H I L H Polygala tricornis Roots [37]See Scheme 4
O
OOO
O
R2O
R4O
R3O
R6O
OH
OH
OH
OH
OR1
OR5CH2OR7
Scheme 4
the doses of 5 10 and 20mgkg was also tested in chronicallymild stressed rats DISS was able to exhibit antidepressantactivity by upregulating the expression of noradrenergic-regulated plasticity genes including cell adhesion moleculeL1 brain-derived neurotrophic factor laminin and cAMP
response element binding protein factor in hippocampus[98] DISS improved the reward reaction by increasingsucrose intake and obviously decreased the levels of serumcortisol adrenocorticotrophic hormone and corticotropin-releasing factor Further DISS played an enhanced role inthe expression of mineralocorticoid receptor together withglucocorticoid receptor mRNA [99]
33 Cytotoxic and Antineoplastic Activities Smilasides AndashFand P smiglasides A and B smilaside P and helonioside Awere isolated from the Smilax Trillium and Paris generaKuo et al obtained smilasides AndashF (51ndash56) and evaluatedtheir cytotoxicity against human tumor cell lines comprisinghuman oral epithelium carcinoma (KB) human cervicalcarcinoma (Hela) human colon tumor (DLD-1) humanbreast adenocarcinoma (MCF-7) human lung carcinoma (A-549) and humanmedulloblastoma (Med) cells byMTTassayExperimental data indicated that all but smilaside C showedcytotoxicity against three to six human tumor cell lines(ED50
= 51ndash130 120583gmL) and smilasides DndashF (ED50
= 27ndash50 120583gmL) displayed strong cytotoxic activities against DLD-1 cells [46]Wang et al reported the antitumor constituents of
Evidence-Based Complementary and Alternative Medicine 15
OH
OH
OH
OH
OH
OHOH
OHOH
OHOH
OH
OHOHOH
OH
OH
OH
OHOH
OH
OH
OHOH
H
H H
HO
O
O
O
O
O
O
O
OO
OO
O
OO
O
HO
HO
HO
OO
O
O
OO
OO
O
OO
O
OO
O
OO
O
O
O
OO
O
O
OO
O
OO
OOOO
HO
HO
HO
HO
HO
HO
HO
HO
HO
HO
HOHO
HO
HO
HO
HO
HO
150 151 152
153 180
AcO
AcO
AcOAcO
OAc
OAc
CH2OH
OHOH
OH OHOH
OHOH
OH
OHOH
CH3O
Figure 5
Table 5 Phenylpropanoid-derived tetrasaccharide esters
Number Name R1 R2 R3 Source Parts Reference154 Tricornose G K H K Polygala tricornis Roots [37]155 Tricornose H K K K Polygala tricornis Roots [37]156 Tricornose I K K L Polygala tricornis Roots [37]157 Tricornose J K I L Polygala tricornis Roots [37]158 Tricornose K K I K Polygala tricornis Roots [37]159 Tricornose L K G K Polygala tricornis Roots [37]See Scheme 5
Smilax riparia including smiglasides A (48) and B (49) 26-di-acetyl-3101584061015840-di-feruloylsucrose (73) helonioside B (40)and smilaside P (65) Only smiglasidesA andB and smilasideP exhibited cytotoxicity against human tumor cell lines withdifferent inhibitory concentrations comparing with cisplatinand paclitaxel as positive controls [47] Helonioside A (39)exhibited higher cytotoxicity with the increase of concentra-tion (01ndash100120583gmL) [45] Tatarisides AndashG (45 119ndash121 46122 47) and diboside A (116) from the Fagopyrum genusexerted cytotoxic activities against different human cell linesand the cytotoxicity of tatariside C was the most remarkablewith the IC
50values ranging from 644 to 749 120583gmL [57]
11015840236-O-Tetra-acetyl-31015840-O-cis-feruloylsucrose (95) fromthe Sparganium plants exhibited extremely weak cyto-toxicity against the growth of mice Lung Adenocarcinoma
795 cell lines with an IC50
value of 116 120583gmL [66] SnS-2oligosaccharides mixture including raffinose (3) stachyose(19) and verbascose (21) from the roots of Scrophularianingpoensis had antitumor activity against the growth ofLewis pulmonary carcinoma cells transplanted into mice[18]
Disaccharide esters and oligosaccharides mixture fromthe Liliaceae Polygonaceae Sparganiaceae and Scrpophular-iaceae families showed effective cytotoxic and antineoplasticactivities The study results indicated that feruloyl and acetylgroups play an important role in mediating cytotoxicitywhich seems to be related to the substitution position offeruloyl groups The feruloyl groups at C-6 or C-11015840 are vitalfor cytotoxicity In addition the increased number of acetylgroups could induce higher tumoricidal activity
16 Evidence-Based Complementary and Alternative Medicine
Table 6 Phenylpropanoid-derived pentasaccharide esters
Number Name R1 R2 R3 R4 R5 R6 Source Parts Reference160 Tenuifoliose A G D I Ac Ac Ac Polygala tenuifolia Roots [38 42]161 Tenuifoliose B G D I H Ac Ac Polygala tenuifolia Roots [42]162 Tenuifoliose C G D I H H H Polygala tenuifolia Roots [42]163 Tenuifoliose F G D U Ac Ac Ac Polygala tenuifolia Roots [42]164 Tenuifoliose G G D U Ac H Ac Polygala tenuifolia Roots [42]165 Tenuifoliose H G D G Ac Ac Ac Polygala tenuifolia Roots [38 42 79]166 Tenuifoliose I G D G Ac H Ac Polygala tenuifolia Roots [42 79]167 Tenuifoliose J G D G H Ac Ac Polygala tenuifolia Roots [42]168 Tenuifoliose K G D G H H Ac Polygala tenuifolia Roots [42]169 Tenuifoliose L G D T Ac Ac Ac Polygala tenuifolia Roots [42 79]170 Tenuifoliose M G D T Ac H Ac Polygala tenuifolia Roots [42]171 Tenuifoliose N I D I Ac Ac Ac Polygala tenuifolia Roots [42]172 Tenuifoliose O I D I H Ac Ac Polygala tenuifolia Roots [42]173 Tenuifoliose P I D I H H Ac Polygala tenuifolia Roots [42]174 Tenuifoliose Q G D T H Ac Ac Polygala tenuifolia Roots [79]175 Tenuifoliose S G D G H H H Polygala tenuifolia Roots [42]176 Tenuifoliose T G D I H H H Polygala tenuifolia Roots [42]177 Tenuifoliose V H D I Ac Ac Ac Polygala tenuifolia Roots [42]178 Tenuifoliose W I D U Ac H Ac Polygala tenuifolia Roots [42]179 Tenuifoliose X I D I H H H Polygala tenuifolia Roots [42]See Scheme 6
O
OO
O
O
O
O
OR1
OH
OH
OH
OHOH
OH
HOHO
HO
HO
OR2
R3O
CH2OH
Scheme 5
34 Anti-Inflammatory Activity Inflammation an importantbasic pathological process is a defense response of biopsywith vascular system to damage stimuli such as pathogensimpaired cells and tissues and physical and chemical factorsHowever if the process of inflammatory response cannot endnormally when cell debris and pathogens were cleared thebiological defence response will become causative factor andbring about many diseases such as diabetes cardiovasculardiseases metabolic syndrome and cancer [100 101]
Tenuifoliside A (44) from the Polygala genus exhibitedstrong anti-inflammatory effect not only by suppressing the
production of NO but also by reducing the production ofiNOS prostaglandin E2 cyclooxygenase-2 and proinflam-matory cytokines through the inhibition of the mitogen-activated protein kinases pathway and NF-120581B pathway [102]The anti-inflammatory activities of quiquesetinerviusides D(108) and E (109) from the Calamus genus were evaluated inRAW 2647 cells Both of them showed significant inhibitoryeffects against the production of LPS-stimulated NOwith theIC50values of 90ndash295120583M [70]Six disaccharide fatty acid esters (132ndash137) were iso-
lated from the Astragalus and Equisetum genera The anti-inflammatory effects of these isolated compounds have alsobeen documented The activation of NF-120581B could upregulatethe expression of proinflammatory cytokines inducible nitricoxide synthase (iNOS) and tumornecrosis factor alpha (TNF-120572) The NF-120581B inhibitory activities of compounds 132ndash137were tested in HepG2 cells stimulated with TNF-120572 All ofthese compounds could significantly restrainTNF-120572-inducedNF-120581B transcriptional activities with the IC
50values of 44ndash
247 120583M Li et al pointed out that olefinic bonds and thelength of the fatty acid moieties contributed to the NF-120581B inhibitory activity Furthermore the inhibition increasedsignificantly with the increase of the number of olefinic bondson the aliphatic moiety [77] These results may provide ascientific basis for the development of new anti-inflammatoryagents
35 Neuroprotective and Cerebral Protective Activities Aswe all know glutamate works as a major excitatory aminoacid neurotransmitter in the mammalian central nervous
Evidence-Based Complementary and Alternative Medicine 17
R6O
R2O
OR3
OR5
OR4
CH2OR1
OCH3
Rham
OO
O
OO O
O
O
O
OO
RhamO
O
OH
OH
OHOH
OH
OHOH
OHHO
HO
HO
T O-rhamnosyl-coumaroyl U O-rhamnosyl-feruloyl
Scheme 6
system and plays a crucial role in several physiological pro-cesses [103] However the accumulation of glutamate inducesdiverse acute and chronic neurodegenerative diseases suchas epilepsy ischemic stroke and Parkinsonrsquos disease aswell as Alzheimerrsquos disease [104] DISS (123) isolated fromthe Polygala genus exhibited neuroprotective effect againstglutamate-induced SH-SY5Y neuronal cell damage The invitro test demonstrated that DISS (06 6 and 60 120583molL)played a critical role in increasing cell viability controllinglactate dehydrogenase and attenuated apoptosis ranging from195 to 258 [105]
Tenuifoliside B (102) from the Polygala genus was ableto significantly shorten the coma time of KCN-inducedanoxia mice at the doses of 3 and 10mgkg and it playedan important role in ameliorating the scopolamine-inducedimpairment of performance in passive avoidance task inrats and enhancing the tremors induced by oxotremorine inmiceThese results together demonstrated that tenuifoliside Bpossessed cognitive improving and cerebral protective effects[56]
36 Antidiabetic Activity Diabetes mellitus a chronic debil-itating metabolic disease is characterized by high bloodglucose content and comprises three types termed type Itype II and gestational diabetes [106] Stachyose (19) extract(a part) from Rehmannia glutinosa obviously exhibited theactivity of downregulating fasting plasma glucose level andpartially keeping from hyperglycemia induced by adrenalineand glucose without obvious dose-dependent effect Otherthan that in vivo tests in rats induced by alloxan revealed
that stachyose extract at the dose of 200mgkg significantlydecreased blood-sugar level [15]
Diboside A lapathosides C and D vanicosides A andB and hydropiperoside were isolated from the FagopyrumPolygonum and Persicaria genera belonging to the Polygo-naceae family Diboside A (116) could potentially inhibit 120572-amylase activity with an IC
50of 269 120583M and thus retard the
starch digestion rate which is helpful for diabetic individualsin controlling blood sugar level [107] Lapathoside D (38)exerted stronger activity of 120572-glucosidase inhibition with anIC50
value of 0113mM than acarbose which was chosen asa positive drug for the treatment of type II diabetes [43]Vanicoside B (111) was reported to have higher 120573-glucosidaseinhibitory activity with an IC
50of 505 120583M than vanicoside A
(110) with an IC50of 599 120583M because of the acetyl moiety of
the latter possibly decreasing inhibitory activity of vanicosideA [71]
Fujimoto et al investigated the inhibitory effects ofmumeoses FndashO (83ndash92) from the Prunus genus on aldosereductase and discovered that caffeoyl groups are crucialfor the inhibitory effect on aldose reductase And thusmumeoses F G H J K L M and N (IC
50= 22ndash77120583M) with
a coumaroyl group and acetyl groups inhibited moderatelyaldose reductase from reducing glucose to sorbitol whichis associated with the chronic complications of diabetes [6364]
37 Elicitors and Regulators Oligosaccharides are quitepropitious for encoding biological information because ofdiverse monosaccharide units and complex molecular struc-tures and they are therefore first described as biological
18 Evidence-Based Complementary and Alternative Medicine
181 H
H
H
H
H
H
H
H
H H
H
H
H
H
H
H
H H
HH
Benzyl
Benzyl
Benzyl
182
183
184 Ac
Ac
Ac
Ac
Ac
Ac
Ac
Ac
Ac
Ac
185
186
187
188
189
R1 R2 R3
R1 R2 R3 R4
OCH3
R3OH2C OR2
OR1
OR1
O
O
O
O O
OOO
O
OO
O
OH
OH
OH OH
OH
O O
O
O
OH
HO
OH
OH OHOH
OH
OH
OHHO
HO
OH
OH
HO
CH2OH
CH2OH
CH2OH
CH2OH
C
R2O
R3O
CH2OR4
CH2CH2 CH2CH2CH2CH2CH3
CH3
CH3
191190 192
193
O
C C
O
OO
OO
OO
OO
O O
O
O
O
O
O
O
OH
OH
OHHO
HO
HOOH
OH
OH
OH
HO
OH
OH
OH
OH
HO
HO
C C
R998400O
R998400
Figure 6
signals in plants [108] Oligosaccharides from the cell wallfragments of plants and fungi are powerful signal moleculessuch as the elicitors of plant defence response and theregulators of plant growth and they are capable of exertingbiological activities at exceedingly low concentrations [109]Heptasaccharide (HS) (15) and octasaccharide (OS) (16) iso-lated from the Paris genus possessed plant growth-regulatory
activities [29 30]The two oligosaccharides significantly pro-moted the proliferation of Paris polyphylla var yunnanensisroots at the doses of 25ndash20mgL The octasaccharide hadthe most obvious effect on the growth of Panax japonicusvar major hairy roots at a dose of 30mgL while the otherhad the most positive effect on saponin accumulation ofPanax japonicus var major hairy roots at a dose of 10mgL
Evidence-Based Complementary and Alternative Medicine 19
[29] Similarly Zhou et al evaluated the stimulating effectsof HS and OS on the root growth and saponin productionof Panax ginseng hairy roots which were induced from theplant roots infected withAgrobacterium rhizogenes strain A4The results showed that there was a maximum effect on thehairy roots growth and saponin accumulation on day 10Compared with control group the root biomass dry weightwas increased by more than 17-fold while the total saponincontent of roots increased by more than 1-fold when thesetwo oligosaccharides were added to the hairy root at a dose of30mgL [30] The above data illustrate that HS and OS couldserve as the plant growth-regulators not only in their originalspecies but also in others
38 Immunopotentiating Activity Macrophages are impor-tant targets of investigations on cytophagy cellular immunityand molecular immunology Therefore they are deemedto play a vital role in host defense comprising phagocy-tosis proteolytic processing pathogenic agent apoptosiscytokines production and foreign antigens presentation[110] The water-extracted oligosaccharides from Panax gin-seng (WGOS) exhibited better immunopotentiating activ-ity by increasing phagocytic function of macrophages andpromoting NO TNF-120572 and reactive oxygen species pro-duction [110] In addition Wan et al have obtained malto-oligosaccharides (17 119899 = 3sim8) and three oligosaccharides (213 14) from the Panax ginseng roots The in vitro bioassaypointed out thatWGOS could serve as efficacious stimulatorsof B and T lymphocytes [28] These studies provided enlight-enment that the mixture of oligosaccharides from Chineseherbalmedicine exhibits significant effect on immune system
39 Others Acetylcholinesterase (AChE) inhibitors showgood therapeutic effects onmyasthenia gravis glaucoma andAlzheimerrsquos disease through reversible enzyme inhibitionso as to increase the accumulation of acetylcholine in thesynapse and then promote and prolong the function ofacetylcholine Vanicoside B (111) showed AChE inhibitoryactivity with an IC
50of 0062mM while hydropiperoside
(42) and lapathosides C (115) and D (38) just exhibited weakenzyme inhibitory activity [43]
Wang et al has explored low molecular mass carbohy-drate polymer from Panax ginseng roots and obtained 30ethanol elution (PGO)which included peptides and oligosac-charides (17 119899 = 0sim5) identified as maltose maltotriosemaltotetraose maltopentaose maltohexaose and maltohep-taose Pharmacological experiments revealed that PGO couldsignificantly enhance the memory in scopolamine-inducedmemory deficit rats [27]
Cistanoside F (129) and kankanose (150) were isolatedfrom the Cistanche Paulownia and Acanthus genera Phar-macological experiments showed that cistanoside F andkankanose significantly exhibited vasorelaxant effects on thenoradrenaline-induced contraction of thoracic aorta fromrats [80]
4 Conclusion
Traditional Chinese medicine from natural kingdom playsan indelible role in the treatment of human diseases andit has aroused the attention of those who have engagedin medicinal pharmaceutical chemistry Therefore scientistshave made great contributions day after day to investigate thevalid chemicals from traditional Chinese medicines In thepast decades about 193 oligosaccharides and their esters havebeen identified from traditional Chinese medicinal plantsOn the one hand only a few oligosaccharides and theirmixtures were investigated and just exhibited antidepres-sant antineoplastic antidiabetic plant growth-regulatoryimmunopotentiating and enhancedmemory activitiesMoreexploratory work is still needed to excavate biological andpharmacological activities of oligosaccharides On the otherhand oligosaccharide esters exhibited multi-advantageousactivities Bioassays have revealed that antioxidant cytotoxicantineoplastic and anti-inflammatory activities are the mostnotable bioactivities Of course to search for the naturalproducts with these activities is a hotpot in the contemporarydrug research Oligosaccharide esters provide a vast treasuretrove for medical researchers After considering the currentstudies it should be taken as future directions to makemore mechanism of action studies and clinical trials tofurther evaluate its potential as new drugs Moreover thestructure-activity relationships discussed in this review willprovide reference information for further exploring theirrelationships and continually discovering the new bioactiveoligosaccharide esters
Conflict of Interests
The authors declare that there is no conflict of interestsregarding the publication of this paper
References
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[2] N Ogwuru and M Adamczeski ldquoBioactive natural productsderived from Polygonum species of plants their structures andmechanisms of actionrdquo Studies in Natural Products Chemistryvol 22 pp 607ndash642 2000
[3] S Kobayashi T Miyase and H Noguchi ldquoPolyphenolic glyco-sides and oligosaccharide multiesters from the roots of Polygaladalmaisianardquo Journal of Natural Products vol 65 no 3 pp 319ndash328 2002
[4] M Takasaki S Kuroki M Kozuka and T Konoshima ldquoNewphenylpropanoid esters of sucrose from Polygonum lapathi-foliumrdquo Journal of Natural Products vol 64 no 10 pp 1305ndash1308 2001
[5] M L Zimmermann and A T Sneden ldquoVanicosides A and Bprotein kinase C inhibitors from Polygonum pensylvanicumrdquoJournal of Natural Products vol 57 no 2 pp 236ndash242 1994
[6] M Takasaki T Konoshima S Kuroki H Tokuda and HNishino ldquoCancer chemopreventive activity of phenylpropanoid
20 Evidence-Based Complementary and Alternative Medicine
esters of sucrose vanicoside B and lapathoside A from Poly-gonum lapathifoliumrdquo Cancer Letters vol 173 no 2 pp 133ndash138 2001
[7] Q Fu T Liang Z Y Li et al ldquoSeparation of carbohydrates usinghydrophilic interaction liquid chromatographyrdquo CarbohydrateResearch vol 379 pp 13ndash17 2013
[8] M F Mrozek D Zhang and D Ben-Amotz ldquoOligosaccharideidentification and mixture quantification using Raman spec-troscopy and chemometric analysisrdquo Carbohydrate Researchvol 339 no 1 pp 141ndash145 2004
[9] G S Armstrong and B Bendiak ldquoHigh-resolution four-dimen-sional carbon-correlated 1H-1H ROESY experiments employ-ing isotags and the filter diagonalization method for effectiveassignment of glycosidic linkages in oligosaccharidesrdquo Journalof Magnetic Resonance vol 181 no 1 pp 79ndash88 2006
[10] G S Armstrong V A Mandelshtam A J Shaka and BBendiak ldquoRapid high-resolution four-dimensional NMR spec-troscopy using the filter diagonalization method and its advan-tages for detailed structural elucidation of oligosaccharidesrdquoJournal of Magnetic Resonance vol 173 no 1 pp 160ndash168 2005
[11] H-M Tseng S Gattolin J Pritchard H J Newbury and DA Barrett ldquoAnalysis of mono- di- and oligosaccharides by CEusing a two-stage derivatization method and LIF detectionrdquoElectrophoresis vol 30 no 8 pp 1399ndash1405 2009
[12] N Li X Li B L Hou and D L Meng ldquoNew disaccharosidefrom Camptosorus sibiricus Ruprrdquo Natural Product Researchvol 22 no 15 pp 1379ndash1383 2008
[13] Z Zhang D Wang Y Zhao H Gao Y-H Hu and J-FHu ldquoFructose-derived carbohydrates from Alisma orientalisrdquoNatural Product Research vol 23 no 11 pp 1013ndash1020 2009
[14] X Yang Y Zhao N He and K D Croft ldquoIsolation char-acterization and immunological effects of 120572-galacto-oligo-saccharides from a new source the herb Lycopus lucidus TurczrdquoJournal of Agricultural and Food Chemistry vol 58 no 14 pp8253ndash8258 2010
[15] R X Zhang Z P Jia L Y Kong et al ldquoStachyose extractfrom Rehmannia glutinosa Libosch to lower plasma glucose innormal and diabetic rats by oral administrationrdquo Pharmazievol 59 no 7 pp 552ndash556 2004
[16] R Zhang Y Zhao Y Sun X Lu and X Yang ldquoIsolationcharacterization and hepatoprotective effects of the raffinosefamily oligosaccharides from Rehmannia glutinosa liboschrdquoJournal of Agricultural and Food Chemistry vol 61 no 32 pp7786ndash7793 2013
[17] H Li F Song Z Zheng Z Liu and S Liu ldquoCharacterization ofsaccharides and phenolic acids in the Chinese herb Tanshen byESI-FT-ICR-MS and HPLCrdquo Journal of Mass Spectrometry vol43 no 11 pp 1545ndash1552 2008
[18] J E Deng J Zhang XM ChenW Ke and G Y Tian ldquoStudieson the physicochemical properties structure and antitumoractivity of an oligosaccharide homologue SnS-2 from the root ofScrophularia ningpoensis Hemslrdquo Chinese Journal of Chemistryvol 22 no 5 pp 492ndash497 2004
[19] S C Chou LM Chuang and S S Lee ldquoHypoglycemic constit-uents of gynura divaricata subsp formosanardquo Natural ProductCommunications vol 7 no 2 pp 221ndash222 2012
[20] F Feng L-L Wang X-P Lai Y-B Li Z-M Cao and Y-J Zhou ldquoStudy on oligosaccharides from Morinda officinalisrdquoJournal of Chinese Medicinal Materials vol 35 no 8 pp 1259ndash1262 2012
[21] Y F Li Z H Gong M Yang Y M Zhao and Z P Luo ldquoInhibi-tion of the oligosaccharides extracted fromMorinda officinalis
a Chinese traditional herbal medicine on the corticosteroneinduced apoptosis in PC12 cellsrdquo Life Sciences vol 72 no 8 pp933ndash942 2003
[22] Y-F Li Y-Q Liu M Yang et al ldquoThe cytoprotective effect ofinulin-type hexasaccharide extracted from Morinda officinalison PC12 cells against the lesion induced by corticosteronerdquo LifeSciences vol 75 no 13 pp 1531ndash1538 2004
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[24] S K Hyun H A Jung B S Min J H Jung and J S ChoildquoIsolation of phenolics nucleosides saccharides and an alkaloidfrom the root of Aralia cordatardquo Natural Product Sciences vol16 no 1 pp 20ndash25 2010
[25] Z J Xu C W Lin and M F Liao ldquoStructure analysis of a newoligosaccharides BROS from Blumea ripariardquo Chinese Journalof Organic Chemistry vol 31 no 11 pp 1811ndash1819 2011
[26] Z J Xu C W Lin and Y Shi ldquoIsolation and structuredetermination of a new oligosaccharide from Blume ripariardquoJournal of Medicinal Plants Research vol 5 no 14 pp 2956ndash2962 2011
[27] Y Wang R Z Jiang G R Li et al ldquoStructural and enhancedmemory activity studies of extracts from Panax ginseng rootrdquoFood Chemistry vol 119 no 3 pp 969ndash973 2010
[28] DWan L Jiao H Yang and S Liu ldquoStructural characterizationand immunological activities of the water-soluble oligosaccha-rides isolated from thePanax ginseng rootsrdquoPlanta vol 235 no6 pp 1289ndash1297 2012
[29] L G Zhou C Z Yang J Q Li S L Wang and J Y WuldquoHeptasaccharide and octasaccharide isolated from Paris pol-yphylla var yunnanensis and their plant growth-regulatoryactivityrdquo Plant Science vol 165 no 3 pp 571ndash575 2003
[30] L G Zhou X D Cao R F Zhang Y L Peng S J Zhao andJ Y Wu ldquoStimulation of saponin production in Panax ginsenghairy roots by two oligosaccharides from Paris polyphylla varyunnanensisrdquo Biotechnology Letters vol 29 no 4 pp 631ndash6342007
[31] M Vanhaecke W van den Ende E Lescrinier and N Dyu-bankova ldquoIsolation and characterization of a pentasaccharidefrom Stellaria mediardquo Journal of Natural Products vol 71 no 11pp 1833ndash1836 2008
[32] J Feng and W Zhao ldquoComplete 1Hand 13C NMR assignmentsof four new oligosaccharides and two new glycosides fromPeriploca forrestiirdquoMagnetic Resonance in Chemistry vol 47 no8 pp 701ndash705 2009
[33] J Q Feng R J Zhang Y Zhou et al ldquoImmunosuppressive preg-nane glycosides from Periploca sepium and Periploca forrestiirdquoPhytochemistry vol 69 no 15 pp 2716ndash2723 2008
[34] X H Long R Xu Y H Zhang X H Tan andQ Y Sun ldquoA newoligosaccharide from Periploca calophyllardquo Zhongguo ZhongyaoZazhi vol 37 no 2 pp 226ndash229 2012
[35] L Wang Z-Q Yin Y Wang X-Q Zhang Y-L Li and W-CYe ldquoPerisesaccharides A-E new oligosaccharides from the rootbarks ofPeriploca sepiumrdquoPlantaMedica vol 76 no 9 pp 909ndash915 2010
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Evidence-Based Complementary and Alternative Medicine 21
[38] H H Tu P Liu L Mu et al ldquoStudy on antidepressant com-ponents of sucrose ester from Polygala tenuifoliardquo ZhongguoZhongyao Zazhi vol 33 no 11 pp 1278ndash1280 2008
[39] G M She Y Y Ba Y Liu H Lv W Wang and R B ShildquoAbsorbable phenylpropenoyl sucroses from Polygala tenuifo-liardquoMolecules vol 16 no 7 pp 5507ndash5513 2011
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[42] Y Ling Z Li M Chen Z Sun M Fan and C HuangldquoAnalysis and detection of the chemical constituents of RadixPolygalae and their metabolites in rats after oral administrationby ultra high-performance liquid chromatography coupledwith electrospray ionization quadrupole time-of-flight tandemmass spectrometryrdquo Journal of Pharmaceutical and BiomedicalAnalysis vol 85 pp 1ndash13 2013
[43] P Fan L Terrier A-E Hay A Marston and K HostettmannldquoAntioxidant and enzyme inhibition activities and chemicalprofiles ofPolygonum sachalinensis FSchmidt exMaxim (Polyg-onaceae)rdquo Fitoterapia vol 81 no 2 pp 124ndash131 2010
[44] L J Zhang C C Liao H C Huang Y C Shen L M Yangand Y H Kuo ldquoAntioxidant phenylpropanoid glycosides fromSmilax bracteatardquo Phytochemistry vol 69 no 6 pp 1398ndash14042008
[45] L L Yan W Y Gao Y J Zhang and Y Wang ldquoA new phenyl-propanoid glycosides from Paris polyphylla var yunnanensisrdquoFitoterapia vol 79 no 4 pp 306ndash307 2008
[46] Y H Kuo Y W Hsu C C Liaw J K Lee H C Huang andL M Y Kuo ldquoCytotoxic phenylpropanoid glycosides from thestems of Smilax chinardquo Journal of Natural Products vol 68 no10 pp 1475ndash1478 2005
[47] W-X Wang T-X Li H Ma J-F Zhang and A-Q JialdquoTumoral cytotoxic and antioxidative phenylpropanoid glyco-sides in Smilax riparia A DCrdquo Journal of Ethnopharmacologyvol 149 no 2 pp 527ndash532 2013
[48] N X Nhiem P vanKiem C vanMinh et al ldquoPhenylpropanoidglycosides fromHeterosmilax erythrantha and their antioxidantactivityrdquo Archives of Pharmacal Research vol 32 no 10 pp1373ndash1377 2009
[49] Y Wang W Y Gao T J Zhang and Y Q Guo ldquoA novelphenylpropanoid glycosides and a new derivation of phenolicglycoside from Paris Polyphylla var yunnanensisrdquo ChineseChemical Letters vol 18 no 5 pp 548ndash550 2007
[50] J-Y Zhang Y-Z Wang Y-L Zhao et al ldquoPhytochemicals andbioactivities of Paris speciesrdquo Journal of Asian Natural ProductsResearch vol 13 no 7 pp 670ndash681 2011
[51] N H N Hashim F Abas K Shaari and N H Lajis ldquoLC-DAD-ESIMSMS characterization of antioxidant and anti-cholinesterase constituents present in the active fraction fromPersicaria hydropiperrdquo LWT Food Science and Technology vol46 no 2 pp 468ndash476 2012
[52] PH FanA EHayAMarstonHX Lou andKHostettmannldquoChemical variability of the invasive neophytes Polygonumcuspidatum Sieb and Zucc and Polygonum sachalinensis FSchmidt ex Maximrdquo Biochemical Systematics and Ecology vol37 no 1 pp 24ndash34 2009
[53] P Liu Y Hu D H Guo et al ldquoPotential antidepressantproperties of Radix Polygalae (Yuan Zhi)rdquo Phytomedicine vol17 no 10 pp 794ndash799 2010
[54] J F Wu S B Chen S L Chen and P F Tu ldquoThe chemical con-stituents of Polygala hongkongensisHemslrdquoActa PharmaceuticaSinica vol 42 no 7 pp 757ndash761 2007
[55] Y Song Y Jiang D Bi X Tian L Liang and P Tu ldquoChemicalconstituents from n-butanol extract of aerial part of Polygalasibiricardquo Zhongguo Zhongyao Zazhi vol 37 no 4 pp 471ndash4742012
[56] Y Ikeya S Takeda M Tunakawa et al ldquoCognitive improvingand cerebral protective effects of acylated oligosaccharides inPolygala tenuifoliardquo Biological and Pharmaceutical Bulletin vol27 no 7 pp 1081ndash1085 2004
[57] C J Zheng C L Hu X Q Ma C Peng H Zhang and L PQin ldquoCytotoxic phenylpropanoid glycosides from Fagopyrumtataricum (L) Gaertnrdquo Food Chemistry vol 132 no 1 pp 433ndash438 2012
[58] X Li Y F Zhang L Yang et al ldquoChemical profiling ofconstituents of Smilacis glabrae using ultra-high pressure liquidchromatography coupled with LTQ orbitrap mass spectrome-tryrdquo Natural Product Communications vol 7 no 2 pp 181ndash1842012
[59] T-T Sun D-W Zhang Y Han F-Y Dong andWWang ldquoSmi-lasides M and N two new phenylpropanoid glycosides fromSmilax ripariardquo Journal of Asian Natural Products Research vol14 no 2 pp 165ndash170 2012
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[61] N Wang X Yao R Ishii and S Kitanaka ldquoBioactive sucroseesters from Bidens parviflorardquo Phytochemistry vol 62 no 5 pp741ndash746 2003
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[63] K Fujimoto SNakamura TMatsumoto et al ldquoMedicinal flow-ers XXXVIII Structures of acylated sucroses and inhibitoryeffects of constituents on aldose reducatase from the flower budsofPrunusmumerdquoChemical and Pharmaceutical Bulletin vol 61no 4 pp 445ndash451 2013
[64] S Nakamura K Fujimoto T Matsumoto et al ldquoStructuresof acylated sucroses and an acylated flavonol glycoside andinhibitory effects of constituents on aldose reductase from theflower buds of Prunus mumerdquo Journal of Natural Medicines vol67 no 4 pp 799ndash806 2013
[65] L-B Dong J He X-Y Li et al ldquoChemical constituents fromthe aerial parts of Musella lasiocarpardquo Natural Products andBioprospecting vol 1 no 1 pp 41ndash47 2011
[66] Y Xiong K Z Deng Y Q Guo W Y Gao and T J ZhangldquoNew chemical constituents from the rhizomes of Sparganiumstoloniferumrdquo Archives of Pharmacal Research vol 32 no 5 pp717ndash720 2009
[67] Y Xiong K-Z Deng Y-Q Guo W-Y Gao and T-J ZhangldquoTwo new sucrose esters from Sparganium stoloniferumrdquo Jour-nal of Asian Natural Products Research vol 10 no 5 pp 425ndash428 2008
[68] B Chen N L Wang J H Huang and X S Yao ldquoIridoidand phenylpropanoid glycosides from Scrophularia ningpoensis
22 Evidence-Based Complementary and Alternative Medicine
Hemslrdquo Asian Journal of Traditional Medicines vol 2 no 3 pp119ndash123 2007
[69] H Chen Y Z Zhou L Qiao et al ldquoTwo new compounds fromCynanchum amplexicaulerdquo Journal of Asian Natural ProductsResearch vol 10 no 3 pp 248ndash251 2008
[70] C-L Chang L-J Zhang R Y Chen et al ldquoAntioxidant andanti-inflammatory phenylpropanoid derivatives from Calamusquiquesetinerviusrdquo Journal of Natural Products vol 73 no 9 pp1482ndash1488 2010
[71] Y Kawai H Kumagai H Kurihara K Yamazaki R Sawanoand N Inoue ldquo120573-Glucosidase inhibitory activities of phenyl-propanoid glycosides vanicoside A and B from Polygonumsachalinense rhizomerdquo Fitoterapia vol 77 no 6 pp 456ndash4592006
[72] P V Kiem N X Nhiem N X Cuong et al ldquoNew phenyl-propanoid esters of sucrose from Polygonum hydropiper andtheir antioxidant activityrdquo Archives of Pharmacal Research vol31 no 11 pp 1477ndash1482 2008
[73] K J Wang Y J Zhang and C R Yang ldquoAntioxidant phenolicconstituents from Fagopyrum dibotrysrdquo Journal of Ethnophar-macology vol 99 no 2 pp 259ndash264 2005
[74] N Cho J Huh H Yang et al ldquoChemical constituentsof Polygala tenuifolia roots and their inhibitory activity onlipopolysaccharide-induced nitric oxide production in BV2microgliardquo Journal of Enzyme Inhibition and Medicinal Chem-istry vol 27 no 1 pp 1ndash4 2012
[75] Q Ren C S Wu and J L Zhang ldquoUse of on-line stop-flowheart-cutting two-dimensional high performance liquid chro-matography for simultaneous determination of 12 major con-stituents in tartary buckwheat (Fagopyrum tataricum Gaertn)rdquoJournal of Chromatography A vol 1304 pp 257ndash262 2013
[76] Q Ren C S Wu Y Ren and J L Zhang ldquoCharacterizationand identification of the chemical constituents from tartarybuckwheat (Fagopyrum tataricumGaertn) by high performanceliquid chromatographyphotodiode array detectorlinear iontrap FTICR hybrid mass spectrometryrdquo Food Chemistry vol136 no 3-4 pp 1377ndash1389 2013
[77] W Li Y N Sun X T Yan et al ldquoNF-120581B inhibitory activityof sucrose fatty acid esters and related constituents fromAstragalus membranaceusrdquo Journal of Agricultural and FoodChemistry vol 61 no 29 pp 7081ndash7088 2013
[78] J T Cheng J He Y Li et al ldquoThree new sucrose fatty acid estersfrom Equisetum hiemale LrdquoHelvetica Chimica Acta vol 95 no7 pp 1158ndash1163 2012
[79] Y Jiang and P-F Tu ldquoTenuifoliose Q a new oligosaccharideester from the root of Polygala tenuifoliaWilldrdquo Journal of AsianNatural Products Research vol 5 no 4 pp 279ndash283 2003
[80] M Yoshikawa H Matsuda T Morikawa H H Xie S Naka-mura and O Muraoka ldquoPhenylethanoid oligoglycosides andacylated oligosugars with vasorelaxant activity from Cistanchetubulosardquo Bioorganic ampMedicinal Chemistry vol 14 no 22 pp7468ndash7475 2006
[81] P-F Tu H-M Shi Z-H Song Y Jiang and Y-Y ZhaoldquoChemical constituents of Cistanche sinensisrdquo Journal of AsianNatural Products Research vol 9 no 1 pp 79ndash84 2007
[82] C-L Si Y-Y Lu P-P Qin R-C Sun and Y-H Ni ldquoPhenolicextractives with chemotaxonomic significance from the bark ofPaulownia tomentosa var tomentosardquo BioResources vol 6 no4 pp 5086ndash5098 2011
[83] J Wu S Zhang Q Xiao et al ldquoPhenylethanoid and aliphaticalcohol glycosides from Acanthus ilicifoliusrdquo Phytochemistryvol 63 no 4 pp 491ndash495 2003
[84] Y Jiang and P-F Tu ldquoAnalysis of chemical constituents inCistanche speciesrdquo Journal of Chromatography A vol 1216 no11 pp 1970ndash1979 2009
[85] H Otsuka H Kuwabara and H Hoshiyama ldquoIdentification ofsucrose diesters of aryldihydronaphthalene-type lignans fromTrigonotis peduncularisand the nature of their fluorescencerdquoJournal of Natural Products vol 71 no 7 pp 1178ndash1181 2008
[86] M-R Suo J-S Yang and Q-H Liu ldquoLignan oligosaccharideesters from Eritrichium rupestrerdquo Journal of Natural Productsvol 69 no 4 pp 682ndash684 2006
[87] P-F Tu Z-H Song H-M Shi Y Jiang and Y-Y ZhaoldquoArylethyl (=phenylethanoid) glycosides and oligosaccharidefrom the stem of Cistanche tubulosardquo Helvetica Chimica Actavol 89 no 5 pp 927ndash935 2006
[88] M-H Shyr T-H Tsai and L-C Lin ldquoRossicasins A Band rosicaside F three new phenylpropanoid glycosides fromBoschniakia rossicardquoChemical and Pharmaceutical Bulletin vol54 no 2 pp 252ndash254 2006
[89] R FangNCVeitchGCKiteM J RHowes EA Porter andM S J Simmonds ldquoGlycosylated constituents of Iris fulvaandIris brevicaulisrdquoChemical amp Pharmaceutical Bulletin vol 59 no1 pp 124ndash128 2011
[90] J Fu L Zuo J Yang R Chen and D Zhang ldquoOligosaccharidepolyester and triterpenoid saponins from the roots of Polygalajaponicardquo Phytochemistry vol 69 no 7 pp 1617ndash1624 2008
[91] M-C Cheng C-Y Li H-C Ko F-N Ko Y-L Lin andT-S Wu ldquoAntidepressant principles of the roots of polygalatenuifoliardquo Journal of Natural Products vol 69 no 9 pp 1305ndash1309 2006
[92] H T Chang and P F Tu ldquoNew oligosaccharide esters andxanthone C-glucosides from Polygala telephioidesrdquo HelveticaChimica Acta vol 90 no 5 pp 944ndash950 2007
[93] J Li L Feng J Dai R Wang and T Nohara ldquoChemical con-stituents from Polygala telephioidesrdquo China Journal of ChineseMateria Medica vol 34 no 4 pp 402ndash405 2009
[94] W-P Yin T-Z Zhao and H-Y Zhang ldquoA novel oligosaccha-ride ester from Syringa pubescensrdquo Journal of Asian NaturalProducts Research vol 10 no 1 pp 95ndash100 2008
[95] M Valko D Leibfritz J Moncol M T D Cronin M Mazurand J Telser ldquoFree radicals and antioxidants in normal physio-logical functions and human diseaserdquoThe International Journalof Biochemistry amp Cell Biology vol 39 no 1 pp 44ndash84 2007
[96] D Krishnaiah R Sarbatly and R Nithyanandam ldquoA review ofthe antioxidant potential of medicinal plant speciesrdquo Food andBioproducts Processing vol 89 no 3 pp 217ndash233 2011
[97] P Liu Y Hu D-H Guo et al ldquoAntioxidant activity ofoligosaccharide ester extracted from Polygala tenuifolia roots insenescence-accelerated micerdquo Pharmaceutical Biology vol 48no 7 pp 828ndash833 2010
[98] Y Hu H-B Liao G Dai-Hong P Liu Y-Y Wang and KRahman ldquoAntidepressant-like effects of 361015840-disinapoyl sucroseon hippocampal neuronal plasticity and neurotrophic signalpathway in chronically mild stressed ratsrdquo NeurochemistryInternational vol 56 no 3 pp 461ndash465 2010
[99] Y Hu H B O Liao P Liu D-H Guo and K RahmanldquoA bioactive compound from Polygala tenuifolia regulatesefficiency of chronic stress on hypothalamic-pituitary-adrenalaxisrdquo Pharmazie vol 64 no 9 pp 605ndash608 2009
[100] A Jungbauer and SMedjakovic ldquoAnti-inflammatory propertiesof culinary herbs and spices that ameliorate the effects ofmetabolic syndromerdquoMaturitas vol 71 no 3 pp 227ndash239 2012
Evidence-Based Complementary and Alternative Medicine 23
[101] Q Xu Y Wang S Guo Z Shen and L Yang ldquoAnti-inflammatory and analgesic activity of aqueous extract of Flospopulirdquo Journal of Ethnopharmacology vol 152 no 3 pp 540ndash545 2014
[102] K S Kim D S Lee G S Bae et al ldquoThe inhibition of JNKMAPK and NF-120581B signaling by tenuifoliside A isolated fromPolygala tenuifolia in lipopolysaccharide-induced macrophagesis associated with its anti-inflammatory effectrdquo European Jour-nal of Pharmacology vol 721 no 1ndash3 pp 267ndash276 2013
[103] J-G Lee J-M Yon C Lin A Y Jung K Y Jung and S-YNamldquoCombined treatment with capsaicin and resveratrol enhancesneuroprotection against glutamate-induced toxicity in mousecerebral cortical neuronsrdquo Food and Chemical Toxicology vol50 no 11 pp 3877ndash3885 2012
[104] M L Jin S Y Park Y H Kim J-I Oh S J Lee andG Park ldquoThe neuroprotective effects of cordycepin inhibitglutamate-induced oxidative andER stress-associated apoptosisin hippocampal HT22 cellsrdquo NeuroToxicology vol 41 pp 102ndash111 2014
[105] P Liu Y Hu J Li et al ldquoProtection of SH-SY5Y neuronal cellsfrom glutamate-induced apoptosis by 36rsquo-disinapoyl sucrosea bioactive compound isolated from radix polygalardquo Journal ofBiomedicine and Biotechnology vol 2012 Article ID 728342 5pages 2012
[106] P-B Li W-L Lin Y-G Wang W Peng X-Y Cai and W-WSu ldquoAntidiabetic activities of oligosaccharides of Ophiopogonisjaponicus in experimental type 2 diabetic ratsrdquo InternationalJournal of Biological Macromolecules vol 51 no 5 pp 749ndash7552012
[107] T Liu Y M Yip L Song et al ldquoInhibiting enzymatic starchdigestion by the phenolic compound diboside A a mechanisticand in silico studyrdquo Food Research International vol 54 no 1pp 595ndash600 2013
[108] F Cote andMGHahn ldquoOligosaccharins structures and signaltransductionrdquo Plant Molecular Biology vol 26 no 5 pp 1379ndash1411 1994
[109] RACreelman and J EMullet ldquoOligosaccharins brassinolidesand jasmonates nontraditional regulators of plant growthdevelopment and gene expressionrdquo Plant Cell vol 9 no 7 pp1211ndash1223 1997
[110] L Jiao D Wan X Zhang B Li H Zhao and S LiuldquoCharacterization and immunostimulating effects on murineperitoneal macrophages of oligosaccharide isolated from Panaxginseng CAMeyerrdquo Journal of Ethnopharmacology vol 144 no3 pp 490ndash496 2012
Submit your manuscripts athttpwwwhindawicom
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Parkinsonrsquos Disease
Evidence-Based Complementary and Alternative Medicine
Volume 2014Hindawi Publishing Corporationhttpwwwhindawicom
Evidence-Based Complementary and Alternative Medicine 9
Table2Con
tinued
Num
ber
Nam
eR 1
R 2R 3
R 4R 5
R 6R 7
R 8Source
Parts
Reference
7526-Di-a
cetyl-31015840-O
-tran
s-feruloy-
61015840-cis-feruloylsucrose
AcH
HAc
ICis-
feruloyl
HH
Smila
xrip
aria
Rootsa
ndrhizom
es[59]
76Re
galosid
eAAc
HH
HI
HH
HTrillium
kamtsc
haticum
Und
ergrou
ndparts
[41]
77Tricorno
seA
AcH
HH
LH
HH
Polyg
alatricornis
Roots
[37]
78Mum
eose
AH
HH
AcG
HH
HPrun
usmum
eFlow
erbu
ds[6263]
79Mum
eose
BAc
HAc
HG
HH
HPrun
usmum
eFlow
erbu
ds[6263]
80Mum
eose
CAc
HAc
AcG
HH
HPrun
usmum
eFlow
erbu
ds[6263]
81Mum
eose
DAc
AcAc
AcG
HH
AcPrun
usmum
eFlow
erbu
ds[6263]
82Mum
eose
EAc
AcAc
AcCis-
coum
aroyl
HH
AcPrun
usmum
eFlow
erbu
ds[6263]
83Mum
eose
FAc
AcAc
HG
HH
HPrun
usmum
eFlow
erbu
ds[63]
84Mum
eose
GAc
HAc
HG
HAc
HPrun
usmum
eFlow
erbu
ds[63]
85Mum
eose
HH
HAc
AcG
HAc
HPrun
usmum
eFlow
erbu
ds[63]
86Mum
eose
IAc
AcAc
HG
AcH
HPrun
usmum
eFlow
erbu
ds[63]
87Mum
eose
JAc
AcAc
AcG
HAc
AcPrun
usmum
eFlow
erbu
ds[63 ]
88Mum
eose
KH
HAc
AcG
HH
HPrun
usmum
eFlow
erbu
ds[64]
89Mum
eose
LAc
HAc
AcG
HAc
HPrun
usmum
eFlow
erbu
ds[64]
90Mum
eose
MAc
AcAc
HG
HAc
AcPrun
usmum
eFlow
erbu
ds[64]
91Mum
eose
NAc
AcAc
HG
AcAc
HPrun
usmum
eFlow
erbu
ds[64]
92Mum
eose
OAc
HAc
AcG
HAc
AcPrun
usmum
eFlow
erbu
ds[64]
9311015840 2346-O-Penta-acetyl-31015840-O
-tra
ns-cou
maroylsu
crose
AcAc
AcAc
GH
HAc
Musellalasio
carpa
Aeria
lparts
[65]
9411015840 2346-O-Penta-acetyl-31015840-O
-cis-cou
maroylsu
crose
AcAc
AcAc
Cis-
coum
aroyl
HH
AcMusellalasio
carpa
Aeria
lparts
[65]
9511015840 236-O-Tetra-acetyl-31015840-O
-cis-
feruloylsucrose
AcH
AcAc
Cis-feruloyl
HH
AcSparganium
stolonifer
umRh
izom
es[66]
9611015840 246-O-Tetra-acetyl-31015840-O
-tra
ns-fe
ruloylsucrose
AcAc
HAc
IH
HAc
Sparganium
stolonifer
umRh
izom
es[66]
9711015840 236-O-Tetra-acetyl-31015840-O
-tra
ns-fe
ruloylsucrose
AcH
AcAc
IH
HAc
Sparganium
stolonifer
umRh
izom
es[67]
98Sibirio
sideA
MH
HH
HH
HH
Scrophularianingpoensis
Roots
[68]
99SibricoseA
1K
HH
HH
HH
HCy
nanchu
mam
plexica
ule
Roots
[69]
100
6-O-C
affeoylsucrose
JH
HH
HH
HH
Scrophularianingpoensis
Roots
[68]
101
Acretosid
eI
HH
HH
HH
HScrophularianingpoensis
Roots
[68]
10 Evidence-Based Complementary and Alternative Medicine
Table2Con
tinued
Num
ber
Nam
eR 1
R 2R 3
R 4R 5
R 6R 7
R 8Source
Parts
Reference
102
Tenu
ifolisideB
FH
HH
KH
HH
Polyg
alatenu
ifolia
Roots
[4256]
103
Tenu
ifolisideC
KH
HH
LH
HH
Polyg
alatricornis
Polyg
alatenu
ifolia
Roots
[374256]
104
Heterosmilasid
eH
HI
HH
IH
HHeterosmila
xerythrantha
Aeria
lparts
[48]
105
Quiqu
esetinerviusideA
HI
HH
II
HH
Calamus
quiquesetin
ervius
Stem
s[70]
106
Quiqu
esetinerviusideB
AcI
HH
II
HH
Calamus
quiquesetin
ervius
Stem
s[70]
107
Quiqu
esetinerviusideC
HI
HAc
II
HH
Calamus
quiquesetin
ervius
Stem
s[70]
108
Quiqu
esetinerviusideD
AcG
HH
II
HH
Calamus
quiquesetin
ervius
Stem
s[70]
109
Quiqu
esetinerviusideE
HG
HAc
II
HH
Calamus
quiquesetin
ervius
Stem
s[70]
110
Vanicosid
eAI
HH
AcG
GH
G
Polyg
onum
sachalinensis
Polyg
onum
cuspidatum
Polyg
onum
hydropiper
Stem
sLeaves
Rhizom
es[51527172]
111
Vanicosid
eBI
HH
HG
GH
G
Polyg
onum
sachalinensis
Polyg
onum
cuspidatum
Persica
riahydropiper
Stem
sLeaves
Rhizom
es[4351527172]
112
Vanicosid
eDG
HH
HG
GH
GPersica
riahydropiper
Leaves
[51]
113
Vanicosid
eEI
AcH
AcG
GH
GPolyg
onum
hydropiper
Stem
sand
leaves
[72]
114
LapathosideA
IH
HH
GG
HI
Polyg
onum
sachalinensis
Polyg
onum
cuspidatum
Fagopyrum
dibotrys
Stem
sRh
izom
es[5173]
115
LapathosideC
IH
HH
GG
HH
Polyg
onum
sachalinensis
Polyg
onum
cuspidatum
Stem
s[4352]
116
DibosideA
GH
HH
GI
HG
Fagopyrum
tataric
umFagopyrum
dibotrys
Roots
Rhizom
es[57]
117
Hidropiperosid
eAI
HH
HH
GH
GPolyg
onum
hydropiper
Stem
sand
leaves
[72]
118
Hidropiperosid
eBI
HH
AcG
GH
IPolyg
onum
hydropiper
Stem
sand
leaves
[72]
119
Tataris
ideB
IH
HAc
GG
HAc
Fagopyrum
tataric
umRo
ots
[57]
Evidence-Based Complementary and Alternative Medicine 11
Table2Con
tinued
Num
ber
Nam
eR 1
R 2R 3
R 4R 5
R 6R 7
R 8Source
Parts
Reference
120
Tataris
ideC
IAc
HAc
GG
HAc
Fagopyrum
tataric
umRo
ots
[57]
121
Tataris
ideD
GH
HAc
GI
HH
Fagopyrum
tataric
umRo
ots
[57]
122
Tataris
ideF
GH
HH
II
HG
Fagopyrum
tataric
umRo
ots
[57]
123
310158406-O
-Di-sinapoylsu
crose
KH
HH
KH
HH
Polyg
alatricornis
Polygalahongkongensis
Polyg
alasib
irica
Polyg
alatenu
ifolia
Cynanchu
mam
plexica
ule
Roots
Root
barks
Who
leplants
Aeria
lparts
[37ndash394153ndash
566974]
124
661015840-O
-Di-c
oumaroylsu
crose
GH
HH
HG
HH
Bidens
parviflora
Who
leplants
[61]
125
11015840 3101584061015840-O
-Tri-
coum
aroyl-6
-feruloylsucrose
IH
HH
GG
HG
Fagopyrum
tataric
umRo
ots
[7576]
126
3101584061015840-O
-Di-c
oumaroyl-110158406-O
-di-
feruloylsucrose
IH
HH
GG
HI
Fagopyrum
tataric
umRo
ots
[7576]
127
31015840-O
-Cou
maroyl-11015840610158406-O
-tri-
feruloylsucrose
IH
HH
IG
HI
Fagopyrum
tataric
umRo
ots
[7576]
128
11015840 31015840610158406-O
-Tetra-fe
ruloylsucrose
IH
HH
II
HI
Fagopyrum
tataric
umRo
ots
[7576]
SeeS
chem
e2
12 Evidence-Based Complementary and Alternative Medicine
131130129
CH2OHOH
OH
OO
OH
C
C
HH
HHO
OO
O
HO
HOHO
HO
HOOH
OHOHOH
OHOH
HOO
O
O
O
HO
HO
OH
OHOHOH
OHOH
HOO
O
O
O
HO
Figure 3
12
3
4
5
6
1998400
2998400
3998400
4998400
5998400
6998400
HO
O
O
R1O
R2O
R8O
R7OOR3
OR4 OR5OR6
Scheme 2
antidepressant cytotoxic antineoplastic anti-inflammatoryantidiabetic plant growth-regulatory neuroprotective andcerebral protective activities Lignan-derived disaccharideesters phenylpropanoid-derived tetrasaccharide esters andpentasaccharide esterswith biological activities have not beenreported Aside from the isolated constituents oligosaccha-ride mixtures from Rehmannia glutinosa Panax ginseng andScrophularia ningpoensiswere also reported to display diversepharmacological activities such as antidiabetic immunopo-tentiating enhanced memory and antineoplastic activitiesThese active compounds and mixtures could serve as thevaluable candidates to be developed as possible drugs for thetreatment and prevention of diseases
31 Antioxidant Activity The adverse effects of oxidativestress proposed to play significant roles in the pathogenesis ofcardiovascular diseases atherosclerosis hypertension can-cer diabetes mellitus neurodegenerative diseases rheuma-toid arthritis ischemiareperfusion injury and ageing havebecome an inevitable and serious issue [95 96] Scientistshave thus made great efforts to explore antioxidants frommedicinal plants by using different kinds of assay methodswhich include DPPH radical scavenging assay hydroxylradical scavenging assay superoxide anion scavenging assayand ABTS radical scavenging method [96]
Lapathosides C and D hydropiperoside vanicoside Bhidropiperosides A and B lapathoside A and diboside Awere isolated from the Polygonum Persicaria and Fagopyrumgenera belonging to the Polygonaceae family The DPPH testrevealed that free radical-scavenging activity of the isolatedcompounds termed lapathoside C (115) hydropiperoside(42) vanicoside B (111) and lapathoside D (38) increasedin turn and lapathoside D exhibited strongest scavengingability with an IC
50of 0088 120583M [43] Hidropiperosides A
and B (117 118) were reported to show obvious antioxidantresponse to DPPH radicals with the SC
50values of 234
and 267 120583gmL respectively while vanicoside E moderatelyexhibited the same activity with a SC
50value of 490 120583gmL
[72] Lapathoside A (114) and diboside A (116) just showedlower antioxidant activities with the SC
50values of 19948 and
16552 120583M respectively [73]Smiglasides A and B smilaside P 26-di-acetyl-3101584061015840-
di-feruloylsucrose helonioside B smilasides GndashL and het-erosmilaside were isolated from the Heterosmilax and Smi-lax genera Compared with ascorbic acid (IC
5014352 120583M)
used as positive control smiglasides A and B and smi-laside P (48 49 65) (IC
5033958 33066 and 31449 120583M
resp) showed higher antioxidant activities than 26-di-acetyl-3101584061015840-di-feruloylsucrose (73) and helonioside B (40) (IC
50
63166 and 51827120583M resp) [47] Additionally Nhiem et alreported that helonioside B heterosmilaside (104) and 26-di-acetyl-3101584061015840-di-feruloylsucrose exhibited important DPPHradical scavenging activities with the SC
50values of 91 127
and 87 120583gmL respectively [48] Compared with smilasidesG-I (57ndash59) (ED
50685ndash794120583M) smilasides JndashL (60ndash62)
showed higher radical scavenging activities with an ED50
value of 267ndash327120583M [44]Five quiquesetinerviusides AndashE (105ndash109) isolated from
the Calamus genus showed weak DPPH scavenging activ-ities (IC
50604ndash1018120583M) but exhibited better hydroxyl
radical scavenging activities (IC50
36ndash84 120583M) Moreoverquiquesetinerviuside C showed superoxide anion scaveng-ing activity with an IC
50value of about 1843 120583M [70]
Liu et al investigated the antioxidant capacity of 310158406-O-di-sinapoylsucrose (DISS) (123) by using the acceleratedsenescence-prone short-lived mice (SAMP) in vivo Theanalyses indicated that the activities of antioxidant enzymesof SOD and glutathione peroxidase ascended obviously inSAMP mice when amended with DISS 50mgkg MoreoverDISS could downregulate and even restore the level ofmalondialdehyde in SAMP model group [97]
From the above studies it can be concluded that oligosac-charide esters with antioxidant activities have been identifiedin the Polygonaceae Liliaceae Smilacaceae and Arecaceaefamilies The results of the antioxidant assays show that theincreased number of phenolic hydroxyl groups and acetylgroups could produce higher antioxidant activity Fan etal indicated that the increased number of phenylpropanoidgroups was not beneficial to free radical scavenging activity[43] Zhang et al pointed out that oligosaccharide esters withferuloyl groups exhibited better antioxidant activities thanthose with coumaroyl groups [44]
Evidence-Based Complementary and Alternative Medicine 13
Table 3 Fatty acid-derived disaccharide esters
Number Name R1 R2 Source Parts Reference132 61015840-O-Linoleylsucrose H O Astragalus membranaceus Roots [77]133 61015840-O-Palmitoylsucrose H P Astragalus membranaceus Roots [77]134 6-O-Palmitoylsucrose P H Astragalus membranaceus Roots [77]
135 61015840-O-Linolenoylsucrose H N Astragalus membranaceusEquisetum hiemale
RootsAerial parts [77 78]
136 6-O-Linoleylsucrose O H Astragalus membranaceus Roots [77]137 6-O-Myristoylsucrose Q H Astragalus membranaceus Roots [77]
138 6-O-[(7Z10Z13Z)-Hexadeca-71013-trienoyl]sucrose H R Equisetum hiemale Aerial parts [78]
139 6-O-[(7Z10Z)-Hexadeca-710-dienoyl]sucrose H S Equisetum hiemale Aerial parts [78]
See Scheme 3
12
3
4
5
6
1998400
2998400
3998400
4998400
5998400
6998400
HO
O
O
R1O
R2O
R8O
R7OOR3
OR4 OR5OR6
O
O
O
18
18
1616
16
14
N linolenoyl
O linoleyl
P palmitoyl
Q myristoyl
O
O
O
R hexadeca-71013-trienoyl
S hexadeca-710-dienoyl
Scheme 3
32 Antidepressant Activity The oligosaccharides obtainedfrom the Morinda genus not only show specific antidepres-sant and antistress activities but also have no suppression orexcitatory effects on central nervous system as well Whatis more they can be taken orally with little toxicity [21]The inulin-type hexasaccharide (IHS) (9) from Morindaofficinalis obviously exhibited cytoprotective activity whichcontributed to the antidepressant effect not only by providingthe PC12 with protection against Cort-induced lesion withIHS 0625 and 125 120583Mbut also by reducing theCort-induced[Ca2+]
119894overloading with IHS 25 and 10 120583M IHS 5 and
10 120583Mupregulated the nerve growth factormRNAexpressionin Cort-induced PC12 cells [22] Polygalatenosides A (181)and B (182) were isolated from the Polygala genus Theysignificantly inhibited the isotope-labeled RTI-55 binding to
norepinephrine transporter protein with the IC50
values of300 and 604 120583M respectively [91]
DISS and tenuifoliside A were isolated from the PolygalaandCynanchum genera Liu et al investigated the antidepres-sant effect of YZ ethanol extract based on the tail suspensiontest (TST) and forced swimming test (FST) which arethe ease-of-use and widely-accepted models for estimatingantidepressant activities in mice The results indicated thatYZ-50 fraction at a dose of 200mgkgwas able to significantlydecrease the immobility time in TST Furthermore YZ-50possessed ability to inhibit corticosterone-induced injury ofhuman neuroblastoma SH-SY5Y cells What is more DISS(123) and tenuifoliside A (44) two major compounds of YZ-50 fraction showed effective protective response to the lesionin SY5Y cells [53] The antidepressant-like effect of DISS at
14 Evidence-Based Complementary and Alternative Medicine
H3CO
HO
HOHO
HO
HO
HO
HOHO
O O
OO O
OO
O
O
O
OO
O
O
OH
OH
OH
OH
OCH3
OCH3
CH2OH
CH2OH
CH2OAc
CH2OAc
H3CO
HOHO
HO
O
O
O
OO
O
O
OH
OH
OH
OCH3
CH2OH
CH2OH
H3CO
H3CO H3CO
HOHO
HO
O
O
O
OO
O
O
OH
OH
OH
OCH3
CH2OH
CH2OAc
CH3O
H
HOHO
HO
HO
HOO O
OO O
OO
OH
OCH3
CH2OHCH2OH
H3CO H3CO
H
CH2CH2 HO
HO
HO
HO
HOO O
OO O
OO
OH
OCH3
CH2OHCH2OAc
H3CO
H
CH2
140 141 142
143 144 145
Figure 4
Table 4 Phenylpropanoid-derived trisaccharide esters
Number Name R1 R2 R3 R4 R5 R6 R7 Source Parts Reference146 Tricornose C K H H H H L H Polygala tricornis Roots [37]147 Tricornose D K H H H H K H Polygala tricornis Roots [37]148 Tricornose E K H H H K L H Polygala tricornis Roots [37]149 Tricornose F K H H H I L H Polygala tricornis Roots [37]See Scheme 4
O
OOO
O
R2O
R4O
R3O
R6O
OH
OH
OH
OH
OR1
OR5CH2OR7
Scheme 4
the doses of 5 10 and 20mgkg was also tested in chronicallymild stressed rats DISS was able to exhibit antidepressantactivity by upregulating the expression of noradrenergic-regulated plasticity genes including cell adhesion moleculeL1 brain-derived neurotrophic factor laminin and cAMP
response element binding protein factor in hippocampus[98] DISS improved the reward reaction by increasingsucrose intake and obviously decreased the levels of serumcortisol adrenocorticotrophic hormone and corticotropin-releasing factor Further DISS played an enhanced role inthe expression of mineralocorticoid receptor together withglucocorticoid receptor mRNA [99]
33 Cytotoxic and Antineoplastic Activities Smilasides AndashFand P smiglasides A and B smilaside P and helonioside Awere isolated from the Smilax Trillium and Paris generaKuo et al obtained smilasides AndashF (51ndash56) and evaluatedtheir cytotoxicity against human tumor cell lines comprisinghuman oral epithelium carcinoma (KB) human cervicalcarcinoma (Hela) human colon tumor (DLD-1) humanbreast adenocarcinoma (MCF-7) human lung carcinoma (A-549) and humanmedulloblastoma (Med) cells byMTTassayExperimental data indicated that all but smilaside C showedcytotoxicity against three to six human tumor cell lines(ED50
= 51ndash130 120583gmL) and smilasides DndashF (ED50
= 27ndash50 120583gmL) displayed strong cytotoxic activities against DLD-1 cells [46]Wang et al reported the antitumor constituents of
Evidence-Based Complementary and Alternative Medicine 15
OH
OH
OH
OH
OH
OHOH
OHOH
OHOH
OH
OHOHOH
OH
OH
OH
OHOH
OH
OH
OHOH
H
H H
HO
O
O
O
O
O
O
O
OO
OO
O
OO
O
HO
HO
HO
OO
O
O
OO
OO
O
OO
O
OO
O
OO
O
O
O
OO
O
O
OO
O
OO
OOOO
HO
HO
HO
HO
HO
HO
HO
HO
HO
HO
HOHO
HO
HO
HO
HO
HO
150 151 152
153 180
AcO
AcO
AcOAcO
OAc
OAc
CH2OH
OHOH
OH OHOH
OHOH
OH
OHOH
CH3O
Figure 5
Table 5 Phenylpropanoid-derived tetrasaccharide esters
Number Name R1 R2 R3 Source Parts Reference154 Tricornose G K H K Polygala tricornis Roots [37]155 Tricornose H K K K Polygala tricornis Roots [37]156 Tricornose I K K L Polygala tricornis Roots [37]157 Tricornose J K I L Polygala tricornis Roots [37]158 Tricornose K K I K Polygala tricornis Roots [37]159 Tricornose L K G K Polygala tricornis Roots [37]See Scheme 5
Smilax riparia including smiglasides A (48) and B (49) 26-di-acetyl-3101584061015840-di-feruloylsucrose (73) helonioside B (40)and smilaside P (65) Only smiglasidesA andB and smilasideP exhibited cytotoxicity against human tumor cell lines withdifferent inhibitory concentrations comparing with cisplatinand paclitaxel as positive controls [47] Helonioside A (39)exhibited higher cytotoxicity with the increase of concentra-tion (01ndash100120583gmL) [45] Tatarisides AndashG (45 119ndash121 46122 47) and diboside A (116) from the Fagopyrum genusexerted cytotoxic activities against different human cell linesand the cytotoxicity of tatariside C was the most remarkablewith the IC
50values ranging from 644 to 749 120583gmL [57]
11015840236-O-Tetra-acetyl-31015840-O-cis-feruloylsucrose (95) fromthe Sparganium plants exhibited extremely weak cyto-toxicity against the growth of mice Lung Adenocarcinoma
795 cell lines with an IC50
value of 116 120583gmL [66] SnS-2oligosaccharides mixture including raffinose (3) stachyose(19) and verbascose (21) from the roots of Scrophularianingpoensis had antitumor activity against the growth ofLewis pulmonary carcinoma cells transplanted into mice[18]
Disaccharide esters and oligosaccharides mixture fromthe Liliaceae Polygonaceae Sparganiaceae and Scrpophular-iaceae families showed effective cytotoxic and antineoplasticactivities The study results indicated that feruloyl and acetylgroups play an important role in mediating cytotoxicitywhich seems to be related to the substitution position offeruloyl groups The feruloyl groups at C-6 or C-11015840 are vitalfor cytotoxicity In addition the increased number of acetylgroups could induce higher tumoricidal activity
16 Evidence-Based Complementary and Alternative Medicine
Table 6 Phenylpropanoid-derived pentasaccharide esters
Number Name R1 R2 R3 R4 R5 R6 Source Parts Reference160 Tenuifoliose A G D I Ac Ac Ac Polygala tenuifolia Roots [38 42]161 Tenuifoliose B G D I H Ac Ac Polygala tenuifolia Roots [42]162 Tenuifoliose C G D I H H H Polygala tenuifolia Roots [42]163 Tenuifoliose F G D U Ac Ac Ac Polygala tenuifolia Roots [42]164 Tenuifoliose G G D U Ac H Ac Polygala tenuifolia Roots [42]165 Tenuifoliose H G D G Ac Ac Ac Polygala tenuifolia Roots [38 42 79]166 Tenuifoliose I G D G Ac H Ac Polygala tenuifolia Roots [42 79]167 Tenuifoliose J G D G H Ac Ac Polygala tenuifolia Roots [42]168 Tenuifoliose K G D G H H Ac Polygala tenuifolia Roots [42]169 Tenuifoliose L G D T Ac Ac Ac Polygala tenuifolia Roots [42 79]170 Tenuifoliose M G D T Ac H Ac Polygala tenuifolia Roots [42]171 Tenuifoliose N I D I Ac Ac Ac Polygala tenuifolia Roots [42]172 Tenuifoliose O I D I H Ac Ac Polygala tenuifolia Roots [42]173 Tenuifoliose P I D I H H Ac Polygala tenuifolia Roots [42]174 Tenuifoliose Q G D T H Ac Ac Polygala tenuifolia Roots [79]175 Tenuifoliose S G D G H H H Polygala tenuifolia Roots [42]176 Tenuifoliose T G D I H H H Polygala tenuifolia Roots [42]177 Tenuifoliose V H D I Ac Ac Ac Polygala tenuifolia Roots [42]178 Tenuifoliose W I D U Ac H Ac Polygala tenuifolia Roots [42]179 Tenuifoliose X I D I H H H Polygala tenuifolia Roots [42]See Scheme 6
O
OO
O
O
O
O
OR1
OH
OH
OH
OHOH
OH
HOHO
HO
HO
OR2
R3O
CH2OH
Scheme 5
34 Anti-Inflammatory Activity Inflammation an importantbasic pathological process is a defense response of biopsywith vascular system to damage stimuli such as pathogensimpaired cells and tissues and physical and chemical factorsHowever if the process of inflammatory response cannot endnormally when cell debris and pathogens were cleared thebiological defence response will become causative factor andbring about many diseases such as diabetes cardiovasculardiseases metabolic syndrome and cancer [100 101]
Tenuifoliside A (44) from the Polygala genus exhibitedstrong anti-inflammatory effect not only by suppressing the
production of NO but also by reducing the production ofiNOS prostaglandin E2 cyclooxygenase-2 and proinflam-matory cytokines through the inhibition of the mitogen-activated protein kinases pathway and NF-120581B pathway [102]The anti-inflammatory activities of quiquesetinerviusides D(108) and E (109) from the Calamus genus were evaluated inRAW 2647 cells Both of them showed significant inhibitoryeffects against the production of LPS-stimulated NOwith theIC50values of 90ndash295120583M [70]Six disaccharide fatty acid esters (132ndash137) were iso-
lated from the Astragalus and Equisetum genera The anti-inflammatory effects of these isolated compounds have alsobeen documented The activation of NF-120581B could upregulatethe expression of proinflammatory cytokines inducible nitricoxide synthase (iNOS) and tumornecrosis factor alpha (TNF-120572) The NF-120581B inhibitory activities of compounds 132ndash137were tested in HepG2 cells stimulated with TNF-120572 All ofthese compounds could significantly restrainTNF-120572-inducedNF-120581B transcriptional activities with the IC
50values of 44ndash
247 120583M Li et al pointed out that olefinic bonds and thelength of the fatty acid moieties contributed to the NF-120581B inhibitory activity Furthermore the inhibition increasedsignificantly with the increase of the number of olefinic bondson the aliphatic moiety [77] These results may provide ascientific basis for the development of new anti-inflammatoryagents
35 Neuroprotective and Cerebral Protective Activities Aswe all know glutamate works as a major excitatory aminoacid neurotransmitter in the mammalian central nervous
Evidence-Based Complementary and Alternative Medicine 17
R6O
R2O
OR3
OR5
OR4
CH2OR1
OCH3
Rham
OO
O
OO O
O
O
O
OO
RhamO
O
OH
OH
OHOH
OH
OHOH
OHHO
HO
HO
T O-rhamnosyl-coumaroyl U O-rhamnosyl-feruloyl
Scheme 6
system and plays a crucial role in several physiological pro-cesses [103] However the accumulation of glutamate inducesdiverse acute and chronic neurodegenerative diseases suchas epilepsy ischemic stroke and Parkinsonrsquos disease aswell as Alzheimerrsquos disease [104] DISS (123) isolated fromthe Polygala genus exhibited neuroprotective effect againstglutamate-induced SH-SY5Y neuronal cell damage The invitro test demonstrated that DISS (06 6 and 60 120583molL)played a critical role in increasing cell viability controllinglactate dehydrogenase and attenuated apoptosis ranging from195 to 258 [105]
Tenuifoliside B (102) from the Polygala genus was ableto significantly shorten the coma time of KCN-inducedanoxia mice at the doses of 3 and 10mgkg and it playedan important role in ameliorating the scopolamine-inducedimpairment of performance in passive avoidance task inrats and enhancing the tremors induced by oxotremorine inmiceThese results together demonstrated that tenuifoliside Bpossessed cognitive improving and cerebral protective effects[56]
36 Antidiabetic Activity Diabetes mellitus a chronic debil-itating metabolic disease is characterized by high bloodglucose content and comprises three types termed type Itype II and gestational diabetes [106] Stachyose (19) extract(a part) from Rehmannia glutinosa obviously exhibited theactivity of downregulating fasting plasma glucose level andpartially keeping from hyperglycemia induced by adrenalineand glucose without obvious dose-dependent effect Otherthan that in vivo tests in rats induced by alloxan revealed
that stachyose extract at the dose of 200mgkg significantlydecreased blood-sugar level [15]
Diboside A lapathosides C and D vanicosides A andB and hydropiperoside were isolated from the FagopyrumPolygonum and Persicaria genera belonging to the Polygo-naceae family Diboside A (116) could potentially inhibit 120572-amylase activity with an IC
50of 269 120583M and thus retard the
starch digestion rate which is helpful for diabetic individualsin controlling blood sugar level [107] Lapathoside D (38)exerted stronger activity of 120572-glucosidase inhibition with anIC50
value of 0113mM than acarbose which was chosen asa positive drug for the treatment of type II diabetes [43]Vanicoside B (111) was reported to have higher 120573-glucosidaseinhibitory activity with an IC
50of 505 120583M than vanicoside A
(110) with an IC50of 599 120583M because of the acetyl moiety of
the latter possibly decreasing inhibitory activity of vanicosideA [71]
Fujimoto et al investigated the inhibitory effects ofmumeoses FndashO (83ndash92) from the Prunus genus on aldosereductase and discovered that caffeoyl groups are crucialfor the inhibitory effect on aldose reductase And thusmumeoses F G H J K L M and N (IC
50= 22ndash77120583M) with
a coumaroyl group and acetyl groups inhibited moderatelyaldose reductase from reducing glucose to sorbitol whichis associated with the chronic complications of diabetes [6364]
37 Elicitors and Regulators Oligosaccharides are quitepropitious for encoding biological information because ofdiverse monosaccharide units and complex molecular struc-tures and they are therefore first described as biological
18 Evidence-Based Complementary and Alternative Medicine
181 H
H
H
H
H
H
H
H
H H
H
H
H
H
H
H
H H
HH
Benzyl
Benzyl
Benzyl
182
183
184 Ac
Ac
Ac
Ac
Ac
Ac
Ac
Ac
Ac
Ac
185
186
187
188
189
R1 R2 R3
R1 R2 R3 R4
OCH3
R3OH2C OR2
OR1
OR1
O
O
O
O O
OOO
O
OO
O
OH
OH
OH OH
OH
O O
O
O
OH
HO
OH
OH OHOH
OH
OH
OHHO
HO
OH
OH
HO
CH2OH
CH2OH
CH2OH
CH2OH
C
R2O
R3O
CH2OR4
CH2CH2 CH2CH2CH2CH2CH3
CH3
CH3
191190 192
193
O
C C
O
OO
OO
OO
OO
O O
O
O
O
O
O
O
OH
OH
OHHO
HO
HOOH
OH
OH
OH
HO
OH
OH
OH
OH
HO
HO
C C
R998400O
R998400
Figure 6
signals in plants [108] Oligosaccharides from the cell wallfragments of plants and fungi are powerful signal moleculessuch as the elicitors of plant defence response and theregulators of plant growth and they are capable of exertingbiological activities at exceedingly low concentrations [109]Heptasaccharide (HS) (15) and octasaccharide (OS) (16) iso-lated from the Paris genus possessed plant growth-regulatory
activities [29 30]The two oligosaccharides significantly pro-moted the proliferation of Paris polyphylla var yunnanensisroots at the doses of 25ndash20mgL The octasaccharide hadthe most obvious effect on the growth of Panax japonicusvar major hairy roots at a dose of 30mgL while the otherhad the most positive effect on saponin accumulation ofPanax japonicus var major hairy roots at a dose of 10mgL
Evidence-Based Complementary and Alternative Medicine 19
[29] Similarly Zhou et al evaluated the stimulating effectsof HS and OS on the root growth and saponin productionof Panax ginseng hairy roots which were induced from theplant roots infected withAgrobacterium rhizogenes strain A4The results showed that there was a maximum effect on thehairy roots growth and saponin accumulation on day 10Compared with control group the root biomass dry weightwas increased by more than 17-fold while the total saponincontent of roots increased by more than 1-fold when thesetwo oligosaccharides were added to the hairy root at a dose of30mgL [30] The above data illustrate that HS and OS couldserve as the plant growth-regulators not only in their originalspecies but also in others
38 Immunopotentiating Activity Macrophages are impor-tant targets of investigations on cytophagy cellular immunityand molecular immunology Therefore they are deemedto play a vital role in host defense comprising phagocy-tosis proteolytic processing pathogenic agent apoptosiscytokines production and foreign antigens presentation[110] The water-extracted oligosaccharides from Panax gin-seng (WGOS) exhibited better immunopotentiating activ-ity by increasing phagocytic function of macrophages andpromoting NO TNF-120572 and reactive oxygen species pro-duction [110] In addition Wan et al have obtained malto-oligosaccharides (17 119899 = 3sim8) and three oligosaccharides (213 14) from the Panax ginseng roots The in vitro bioassaypointed out thatWGOS could serve as efficacious stimulatorsof B and T lymphocytes [28] These studies provided enlight-enment that the mixture of oligosaccharides from Chineseherbalmedicine exhibits significant effect on immune system
39 Others Acetylcholinesterase (AChE) inhibitors showgood therapeutic effects onmyasthenia gravis glaucoma andAlzheimerrsquos disease through reversible enzyme inhibitionso as to increase the accumulation of acetylcholine in thesynapse and then promote and prolong the function ofacetylcholine Vanicoside B (111) showed AChE inhibitoryactivity with an IC
50of 0062mM while hydropiperoside
(42) and lapathosides C (115) and D (38) just exhibited weakenzyme inhibitory activity [43]
Wang et al has explored low molecular mass carbohy-drate polymer from Panax ginseng roots and obtained 30ethanol elution (PGO)which included peptides and oligosac-charides (17 119899 = 0sim5) identified as maltose maltotriosemaltotetraose maltopentaose maltohexaose and maltohep-taose Pharmacological experiments revealed that PGO couldsignificantly enhance the memory in scopolamine-inducedmemory deficit rats [27]
Cistanoside F (129) and kankanose (150) were isolatedfrom the Cistanche Paulownia and Acanthus genera Phar-macological experiments showed that cistanoside F andkankanose significantly exhibited vasorelaxant effects on thenoradrenaline-induced contraction of thoracic aorta fromrats [80]
4 Conclusion
Traditional Chinese medicine from natural kingdom playsan indelible role in the treatment of human diseases andit has aroused the attention of those who have engagedin medicinal pharmaceutical chemistry Therefore scientistshave made great contributions day after day to investigate thevalid chemicals from traditional Chinese medicines In thepast decades about 193 oligosaccharides and their esters havebeen identified from traditional Chinese medicinal plantsOn the one hand only a few oligosaccharides and theirmixtures were investigated and just exhibited antidepres-sant antineoplastic antidiabetic plant growth-regulatoryimmunopotentiating and enhancedmemory activitiesMoreexploratory work is still needed to excavate biological andpharmacological activities of oligosaccharides On the otherhand oligosaccharide esters exhibited multi-advantageousactivities Bioassays have revealed that antioxidant cytotoxicantineoplastic and anti-inflammatory activities are the mostnotable bioactivities Of course to search for the naturalproducts with these activities is a hotpot in the contemporarydrug research Oligosaccharide esters provide a vast treasuretrove for medical researchers After considering the currentstudies it should be taken as future directions to makemore mechanism of action studies and clinical trials tofurther evaluate its potential as new drugs Moreover thestructure-activity relationships discussed in this review willprovide reference information for further exploring theirrelationships and continually discovering the new bioactiveoligosaccharide esters
Conflict of Interests
The authors declare that there is no conflict of interestsregarding the publication of this paper
References
[1] X D Yang L J Zhang B Liang L Z Xu and S L YangldquoOligosaccharide esters isolated from plants of PolygalaceaerdquoChinese Traditional and Herbal Drugs vol 33 no 10 pp 954ndash958 2002
[2] N Ogwuru and M Adamczeski ldquoBioactive natural productsderived from Polygonum species of plants their structures andmechanisms of actionrdquo Studies in Natural Products Chemistryvol 22 pp 607ndash642 2000
[3] S Kobayashi T Miyase and H Noguchi ldquoPolyphenolic glyco-sides and oligosaccharide multiesters from the roots of Polygaladalmaisianardquo Journal of Natural Products vol 65 no 3 pp 319ndash328 2002
[4] M Takasaki S Kuroki M Kozuka and T Konoshima ldquoNewphenylpropanoid esters of sucrose from Polygonum lapathi-foliumrdquo Journal of Natural Products vol 64 no 10 pp 1305ndash1308 2001
[5] M L Zimmermann and A T Sneden ldquoVanicosides A and Bprotein kinase C inhibitors from Polygonum pensylvanicumrdquoJournal of Natural Products vol 57 no 2 pp 236ndash242 1994
[6] M Takasaki T Konoshima S Kuroki H Tokuda and HNishino ldquoCancer chemopreventive activity of phenylpropanoid
20 Evidence-Based Complementary and Alternative Medicine
esters of sucrose vanicoside B and lapathoside A from Poly-gonum lapathifoliumrdquo Cancer Letters vol 173 no 2 pp 133ndash138 2001
[7] Q Fu T Liang Z Y Li et al ldquoSeparation of carbohydrates usinghydrophilic interaction liquid chromatographyrdquo CarbohydrateResearch vol 379 pp 13ndash17 2013
[8] M F Mrozek D Zhang and D Ben-Amotz ldquoOligosaccharideidentification and mixture quantification using Raman spec-troscopy and chemometric analysisrdquo Carbohydrate Researchvol 339 no 1 pp 141ndash145 2004
[9] G S Armstrong and B Bendiak ldquoHigh-resolution four-dimen-sional carbon-correlated 1H-1H ROESY experiments employ-ing isotags and the filter diagonalization method for effectiveassignment of glycosidic linkages in oligosaccharidesrdquo Journalof Magnetic Resonance vol 181 no 1 pp 79ndash88 2006
[10] G S Armstrong V A Mandelshtam A J Shaka and BBendiak ldquoRapid high-resolution four-dimensional NMR spec-troscopy using the filter diagonalization method and its advan-tages for detailed structural elucidation of oligosaccharidesrdquoJournal of Magnetic Resonance vol 173 no 1 pp 160ndash168 2005
[11] H-M Tseng S Gattolin J Pritchard H J Newbury and DA Barrett ldquoAnalysis of mono- di- and oligosaccharides by CEusing a two-stage derivatization method and LIF detectionrdquoElectrophoresis vol 30 no 8 pp 1399ndash1405 2009
[12] N Li X Li B L Hou and D L Meng ldquoNew disaccharosidefrom Camptosorus sibiricus Ruprrdquo Natural Product Researchvol 22 no 15 pp 1379ndash1383 2008
[13] Z Zhang D Wang Y Zhao H Gao Y-H Hu and J-FHu ldquoFructose-derived carbohydrates from Alisma orientalisrdquoNatural Product Research vol 23 no 11 pp 1013ndash1020 2009
[14] X Yang Y Zhao N He and K D Croft ldquoIsolation char-acterization and immunological effects of 120572-galacto-oligo-saccharides from a new source the herb Lycopus lucidus TurczrdquoJournal of Agricultural and Food Chemistry vol 58 no 14 pp8253ndash8258 2010
[15] R X Zhang Z P Jia L Y Kong et al ldquoStachyose extractfrom Rehmannia glutinosa Libosch to lower plasma glucose innormal and diabetic rats by oral administrationrdquo Pharmazievol 59 no 7 pp 552ndash556 2004
[16] R Zhang Y Zhao Y Sun X Lu and X Yang ldquoIsolationcharacterization and hepatoprotective effects of the raffinosefamily oligosaccharides from Rehmannia glutinosa liboschrdquoJournal of Agricultural and Food Chemistry vol 61 no 32 pp7786ndash7793 2013
[17] H Li F Song Z Zheng Z Liu and S Liu ldquoCharacterization ofsaccharides and phenolic acids in the Chinese herb Tanshen byESI-FT-ICR-MS and HPLCrdquo Journal of Mass Spectrometry vol43 no 11 pp 1545ndash1552 2008
[18] J E Deng J Zhang XM ChenW Ke and G Y Tian ldquoStudieson the physicochemical properties structure and antitumoractivity of an oligosaccharide homologue SnS-2 from the root ofScrophularia ningpoensis Hemslrdquo Chinese Journal of Chemistryvol 22 no 5 pp 492ndash497 2004
[19] S C Chou LM Chuang and S S Lee ldquoHypoglycemic constit-uents of gynura divaricata subsp formosanardquo Natural ProductCommunications vol 7 no 2 pp 221ndash222 2012
[20] F Feng L-L Wang X-P Lai Y-B Li Z-M Cao and Y-J Zhou ldquoStudy on oligosaccharides from Morinda officinalisrdquoJournal of Chinese Medicinal Materials vol 35 no 8 pp 1259ndash1262 2012
[21] Y F Li Z H Gong M Yang Y M Zhao and Z P Luo ldquoInhibi-tion of the oligosaccharides extracted fromMorinda officinalis
a Chinese traditional herbal medicine on the corticosteroneinduced apoptosis in PC12 cellsrdquo Life Sciences vol 72 no 8 pp933ndash942 2003
[22] Y-F Li Y-Q Liu M Yang et al ldquoThe cytoprotective effect ofinulin-type hexasaccharide extracted from Morinda officinalison PC12 cells against the lesion induced by corticosteronerdquo LifeSciences vol 75 no 13 pp 1531ndash1538 2004
[23] D N Olennikov L M Tankhaeva and A V Rokhin ldquoGlu-cofructans from Saussurea lappa rootsrdquo Chemistry of NaturalCompounds vol 47 no 3 pp 339ndash342 2011
[24] S K Hyun H A Jung B S Min J H Jung and J S ChoildquoIsolation of phenolics nucleosides saccharides and an alkaloidfrom the root of Aralia cordatardquo Natural Product Sciences vol16 no 1 pp 20ndash25 2010
[25] Z J Xu C W Lin and M F Liao ldquoStructure analysis of a newoligosaccharides BROS from Blumea ripariardquo Chinese Journalof Organic Chemistry vol 31 no 11 pp 1811ndash1819 2011
[26] Z J Xu C W Lin and Y Shi ldquoIsolation and structuredetermination of a new oligosaccharide from Blume ripariardquoJournal of Medicinal Plants Research vol 5 no 14 pp 2956ndash2962 2011
[27] Y Wang R Z Jiang G R Li et al ldquoStructural and enhancedmemory activity studies of extracts from Panax ginseng rootrdquoFood Chemistry vol 119 no 3 pp 969ndash973 2010
[28] DWan L Jiao H Yang and S Liu ldquoStructural characterizationand immunological activities of the water-soluble oligosaccha-rides isolated from thePanax ginseng rootsrdquoPlanta vol 235 no6 pp 1289ndash1297 2012
[29] L G Zhou C Z Yang J Q Li S L Wang and J Y WuldquoHeptasaccharide and octasaccharide isolated from Paris pol-yphylla var yunnanensis and their plant growth-regulatoryactivityrdquo Plant Science vol 165 no 3 pp 571ndash575 2003
[30] L G Zhou X D Cao R F Zhang Y L Peng S J Zhao andJ Y Wu ldquoStimulation of saponin production in Panax ginsenghairy roots by two oligosaccharides from Paris polyphylla varyunnanensisrdquo Biotechnology Letters vol 29 no 4 pp 631ndash6342007
[31] M Vanhaecke W van den Ende E Lescrinier and N Dyu-bankova ldquoIsolation and characterization of a pentasaccharidefrom Stellaria mediardquo Journal of Natural Products vol 71 no 11pp 1833ndash1836 2008
[32] J Feng and W Zhao ldquoComplete 1Hand 13C NMR assignmentsof four new oligosaccharides and two new glycosides fromPeriploca forrestiirdquoMagnetic Resonance in Chemistry vol 47 no8 pp 701ndash705 2009
[33] J Q Feng R J Zhang Y Zhou et al ldquoImmunosuppressive preg-nane glycosides from Periploca sepium and Periploca forrestiirdquoPhytochemistry vol 69 no 15 pp 2716ndash2723 2008
[34] X H Long R Xu Y H Zhang X H Tan andQ Y Sun ldquoA newoligosaccharide from Periploca calophyllardquo Zhongguo ZhongyaoZazhi vol 37 no 2 pp 226ndash229 2012
[35] L Wang Z-Q Yin Y Wang X-Q Zhang Y-L Li and W-CYe ldquoPerisesaccharides A-E new oligosaccharides from the rootbarks ofPeriploca sepiumrdquoPlantaMedica vol 76 no 9 pp 909ndash915 2010
[36] T Lei L Zhang H-Y Jiang Y Hu A-H Hong and Y-Z CenldquoA new pregnane glycoside and oligosaccharide from Parabar-ium huaitingiirdquo Journal of Asian Natural Products Research vol13 no 11 pp 1030ndash1035 2011
[37] J Li Y Jiang and P F Tu ldquoTricornoses A-L oligosaccharidemulti-esters from the roots of Polygala tricornisrdquo Journal ofNatural Products vol 68 no 5 pp 739ndash744 2005
Evidence-Based Complementary and Alternative Medicine 21
[38] H H Tu P Liu L Mu et al ldquoStudy on antidepressant com-ponents of sucrose ester from Polygala tenuifoliardquo ZhongguoZhongyao Zazhi vol 33 no 11 pp 1278ndash1280 2008
[39] G M She Y Y Ba Y Liu H Lv W Wang and R B ShildquoAbsorbable phenylpropenoyl sucroses from Polygala tenuifo-liardquoMolecules vol 16 no 7 pp 5507ndash5513 2011
[40] J Yong and P F Tu ldquoStudies on the chemical constituents inroot bark of Polygala tenuifolia (II)rdquo China Journal of ChineseMateria Medica vol 29 no 8 pp 751ndash753 2004
[41] M Ono C Takamura F Sugita et al ldquoTwo new steroidglycosides and a new sesquiterpenoid glycoside from theunderground parts of Trillium kamtschaticumrdquo Chemical andPharmaceutical Bulletin vol 55 no 4 pp 551ndash556 2007
[42] Y Ling Z Li M Chen Z Sun M Fan and C HuangldquoAnalysis and detection of the chemical constituents of RadixPolygalae and their metabolites in rats after oral administrationby ultra high-performance liquid chromatography coupledwith electrospray ionization quadrupole time-of-flight tandemmass spectrometryrdquo Journal of Pharmaceutical and BiomedicalAnalysis vol 85 pp 1ndash13 2013
[43] P Fan L Terrier A-E Hay A Marston and K HostettmannldquoAntioxidant and enzyme inhibition activities and chemicalprofiles ofPolygonum sachalinensis FSchmidt exMaxim (Polyg-onaceae)rdquo Fitoterapia vol 81 no 2 pp 124ndash131 2010
[44] L J Zhang C C Liao H C Huang Y C Shen L M Yangand Y H Kuo ldquoAntioxidant phenylpropanoid glycosides fromSmilax bracteatardquo Phytochemistry vol 69 no 6 pp 1398ndash14042008
[45] L L Yan W Y Gao Y J Zhang and Y Wang ldquoA new phenyl-propanoid glycosides from Paris polyphylla var yunnanensisrdquoFitoterapia vol 79 no 4 pp 306ndash307 2008
[46] Y H Kuo Y W Hsu C C Liaw J K Lee H C Huang andL M Y Kuo ldquoCytotoxic phenylpropanoid glycosides from thestems of Smilax chinardquo Journal of Natural Products vol 68 no10 pp 1475ndash1478 2005
[47] W-X Wang T-X Li H Ma J-F Zhang and A-Q JialdquoTumoral cytotoxic and antioxidative phenylpropanoid glyco-sides in Smilax riparia A DCrdquo Journal of Ethnopharmacologyvol 149 no 2 pp 527ndash532 2013
[48] N X Nhiem P vanKiem C vanMinh et al ldquoPhenylpropanoidglycosides fromHeterosmilax erythrantha and their antioxidantactivityrdquo Archives of Pharmacal Research vol 32 no 10 pp1373ndash1377 2009
[49] Y Wang W Y Gao T J Zhang and Y Q Guo ldquoA novelphenylpropanoid glycosides and a new derivation of phenolicglycoside from Paris Polyphylla var yunnanensisrdquo ChineseChemical Letters vol 18 no 5 pp 548ndash550 2007
[50] J-Y Zhang Y-Z Wang Y-L Zhao et al ldquoPhytochemicals andbioactivities of Paris speciesrdquo Journal of Asian Natural ProductsResearch vol 13 no 7 pp 670ndash681 2011
[51] N H N Hashim F Abas K Shaari and N H Lajis ldquoLC-DAD-ESIMSMS characterization of antioxidant and anti-cholinesterase constituents present in the active fraction fromPersicaria hydropiperrdquo LWT Food Science and Technology vol46 no 2 pp 468ndash476 2012
[52] PH FanA EHayAMarstonHX Lou andKHostettmannldquoChemical variability of the invasive neophytes Polygonumcuspidatum Sieb and Zucc and Polygonum sachalinensis FSchmidt ex Maximrdquo Biochemical Systematics and Ecology vol37 no 1 pp 24ndash34 2009
[53] P Liu Y Hu D H Guo et al ldquoPotential antidepressantproperties of Radix Polygalae (Yuan Zhi)rdquo Phytomedicine vol17 no 10 pp 794ndash799 2010
[54] J F Wu S B Chen S L Chen and P F Tu ldquoThe chemical con-stituents of Polygala hongkongensisHemslrdquoActa PharmaceuticaSinica vol 42 no 7 pp 757ndash761 2007
[55] Y Song Y Jiang D Bi X Tian L Liang and P Tu ldquoChemicalconstituents from n-butanol extract of aerial part of Polygalasibiricardquo Zhongguo Zhongyao Zazhi vol 37 no 4 pp 471ndash4742012
[56] Y Ikeya S Takeda M Tunakawa et al ldquoCognitive improvingand cerebral protective effects of acylated oligosaccharides inPolygala tenuifoliardquo Biological and Pharmaceutical Bulletin vol27 no 7 pp 1081ndash1085 2004
[57] C J Zheng C L Hu X Q Ma C Peng H Zhang and L PQin ldquoCytotoxic phenylpropanoid glycosides from Fagopyrumtataricum (L) Gaertnrdquo Food Chemistry vol 132 no 1 pp 433ndash438 2012
[58] X Li Y F Zhang L Yang et al ldquoChemical profiling ofconstituents of Smilacis glabrae using ultra-high pressure liquidchromatography coupled with LTQ orbitrap mass spectrome-tryrdquo Natural Product Communications vol 7 no 2 pp 181ndash1842012
[59] T-T Sun D-W Zhang Y Han F-Y Dong andWWang ldquoSmi-lasides M and N two new phenylpropanoid glycosides fromSmilax ripariardquo Journal of Asian Natural Products Research vol14 no 2 pp 165ndash170 2012
[60] J Li X Bi G Zheng Y Hitoshi T Ikeda and T NoharaldquoSteroidal glycosides and aromatic compounds from Smilaxripariardquo Chemical amp Pharmaceutical Bulletin vol 54 no 10 pp1451ndash1454 2006
[61] N Wang X Yao R Ishii and S Kitanaka ldquoBioactive sucroseesters from Bidens parviflorardquo Phytochemistry vol 62 no 5 pp741ndash746 2003
[62] S Nakamura K Fujimoto T Matsumoto et al ldquoAcylatedsucroses and acylated quinic acids analogs from the flower budsof Prunus mume and their inhibitory effect on melanogenesisrdquoPhytochemistry vol 92 pp 128ndash136 2013
[63] K Fujimoto SNakamura TMatsumoto et al ldquoMedicinal flow-ers XXXVIII Structures of acylated sucroses and inhibitoryeffects of constituents on aldose reducatase from the flower budsofPrunusmumerdquoChemical and Pharmaceutical Bulletin vol 61no 4 pp 445ndash451 2013
[64] S Nakamura K Fujimoto T Matsumoto et al ldquoStructuresof acylated sucroses and an acylated flavonol glycoside andinhibitory effects of constituents on aldose reductase from theflower buds of Prunus mumerdquo Journal of Natural Medicines vol67 no 4 pp 799ndash806 2013
[65] L-B Dong J He X-Y Li et al ldquoChemical constituents fromthe aerial parts of Musella lasiocarpardquo Natural Products andBioprospecting vol 1 no 1 pp 41ndash47 2011
[66] Y Xiong K Z Deng Y Q Guo W Y Gao and T J ZhangldquoNew chemical constituents from the rhizomes of Sparganiumstoloniferumrdquo Archives of Pharmacal Research vol 32 no 5 pp717ndash720 2009
[67] Y Xiong K-Z Deng Y-Q Guo W-Y Gao and T-J ZhangldquoTwo new sucrose esters from Sparganium stoloniferumrdquo Jour-nal of Asian Natural Products Research vol 10 no 5 pp 425ndash428 2008
[68] B Chen N L Wang J H Huang and X S Yao ldquoIridoidand phenylpropanoid glycosides from Scrophularia ningpoensis
22 Evidence-Based Complementary and Alternative Medicine
Hemslrdquo Asian Journal of Traditional Medicines vol 2 no 3 pp119ndash123 2007
[69] H Chen Y Z Zhou L Qiao et al ldquoTwo new compounds fromCynanchum amplexicaulerdquo Journal of Asian Natural ProductsResearch vol 10 no 3 pp 248ndash251 2008
[70] C-L Chang L-J Zhang R Y Chen et al ldquoAntioxidant andanti-inflammatory phenylpropanoid derivatives from Calamusquiquesetinerviusrdquo Journal of Natural Products vol 73 no 9 pp1482ndash1488 2010
[71] Y Kawai H Kumagai H Kurihara K Yamazaki R Sawanoand N Inoue ldquo120573-Glucosidase inhibitory activities of phenyl-propanoid glycosides vanicoside A and B from Polygonumsachalinense rhizomerdquo Fitoterapia vol 77 no 6 pp 456ndash4592006
[72] P V Kiem N X Nhiem N X Cuong et al ldquoNew phenyl-propanoid esters of sucrose from Polygonum hydropiper andtheir antioxidant activityrdquo Archives of Pharmacal Research vol31 no 11 pp 1477ndash1482 2008
[73] K J Wang Y J Zhang and C R Yang ldquoAntioxidant phenolicconstituents from Fagopyrum dibotrysrdquo Journal of Ethnophar-macology vol 99 no 2 pp 259ndash264 2005
[74] N Cho J Huh H Yang et al ldquoChemical constituentsof Polygala tenuifolia roots and their inhibitory activity onlipopolysaccharide-induced nitric oxide production in BV2microgliardquo Journal of Enzyme Inhibition and Medicinal Chem-istry vol 27 no 1 pp 1ndash4 2012
[75] Q Ren C S Wu and J L Zhang ldquoUse of on-line stop-flowheart-cutting two-dimensional high performance liquid chro-matography for simultaneous determination of 12 major con-stituents in tartary buckwheat (Fagopyrum tataricum Gaertn)rdquoJournal of Chromatography A vol 1304 pp 257ndash262 2013
[76] Q Ren C S Wu Y Ren and J L Zhang ldquoCharacterizationand identification of the chemical constituents from tartarybuckwheat (Fagopyrum tataricumGaertn) by high performanceliquid chromatographyphotodiode array detectorlinear iontrap FTICR hybrid mass spectrometryrdquo Food Chemistry vol136 no 3-4 pp 1377ndash1389 2013
[77] W Li Y N Sun X T Yan et al ldquoNF-120581B inhibitory activityof sucrose fatty acid esters and related constituents fromAstragalus membranaceusrdquo Journal of Agricultural and FoodChemistry vol 61 no 29 pp 7081ndash7088 2013
[78] J T Cheng J He Y Li et al ldquoThree new sucrose fatty acid estersfrom Equisetum hiemale LrdquoHelvetica Chimica Acta vol 95 no7 pp 1158ndash1163 2012
[79] Y Jiang and P-F Tu ldquoTenuifoliose Q a new oligosaccharideester from the root of Polygala tenuifoliaWilldrdquo Journal of AsianNatural Products Research vol 5 no 4 pp 279ndash283 2003
[80] M Yoshikawa H Matsuda T Morikawa H H Xie S Naka-mura and O Muraoka ldquoPhenylethanoid oligoglycosides andacylated oligosugars with vasorelaxant activity from Cistanchetubulosardquo Bioorganic ampMedicinal Chemistry vol 14 no 22 pp7468ndash7475 2006
[81] P-F Tu H-M Shi Z-H Song Y Jiang and Y-Y ZhaoldquoChemical constituents of Cistanche sinensisrdquo Journal of AsianNatural Products Research vol 9 no 1 pp 79ndash84 2007
[82] C-L Si Y-Y Lu P-P Qin R-C Sun and Y-H Ni ldquoPhenolicextractives with chemotaxonomic significance from the bark ofPaulownia tomentosa var tomentosardquo BioResources vol 6 no4 pp 5086ndash5098 2011
[83] J Wu S Zhang Q Xiao et al ldquoPhenylethanoid and aliphaticalcohol glycosides from Acanthus ilicifoliusrdquo Phytochemistryvol 63 no 4 pp 491ndash495 2003
[84] Y Jiang and P-F Tu ldquoAnalysis of chemical constituents inCistanche speciesrdquo Journal of Chromatography A vol 1216 no11 pp 1970ndash1979 2009
[85] H Otsuka H Kuwabara and H Hoshiyama ldquoIdentification ofsucrose diesters of aryldihydronaphthalene-type lignans fromTrigonotis peduncularisand the nature of their fluorescencerdquoJournal of Natural Products vol 71 no 7 pp 1178ndash1181 2008
[86] M-R Suo J-S Yang and Q-H Liu ldquoLignan oligosaccharideesters from Eritrichium rupestrerdquo Journal of Natural Productsvol 69 no 4 pp 682ndash684 2006
[87] P-F Tu Z-H Song H-M Shi Y Jiang and Y-Y ZhaoldquoArylethyl (=phenylethanoid) glycosides and oligosaccharidefrom the stem of Cistanche tubulosardquo Helvetica Chimica Actavol 89 no 5 pp 927ndash935 2006
[88] M-H Shyr T-H Tsai and L-C Lin ldquoRossicasins A Band rosicaside F three new phenylpropanoid glycosides fromBoschniakia rossicardquoChemical and Pharmaceutical Bulletin vol54 no 2 pp 252ndash254 2006
[89] R FangNCVeitchGCKiteM J RHowes EA Porter andM S J Simmonds ldquoGlycosylated constituents of Iris fulvaandIris brevicaulisrdquoChemical amp Pharmaceutical Bulletin vol 59 no1 pp 124ndash128 2011
[90] J Fu L Zuo J Yang R Chen and D Zhang ldquoOligosaccharidepolyester and triterpenoid saponins from the roots of Polygalajaponicardquo Phytochemistry vol 69 no 7 pp 1617ndash1624 2008
[91] M-C Cheng C-Y Li H-C Ko F-N Ko Y-L Lin andT-S Wu ldquoAntidepressant principles of the roots of polygalatenuifoliardquo Journal of Natural Products vol 69 no 9 pp 1305ndash1309 2006
[92] H T Chang and P F Tu ldquoNew oligosaccharide esters andxanthone C-glucosides from Polygala telephioidesrdquo HelveticaChimica Acta vol 90 no 5 pp 944ndash950 2007
[93] J Li L Feng J Dai R Wang and T Nohara ldquoChemical con-stituents from Polygala telephioidesrdquo China Journal of ChineseMateria Medica vol 34 no 4 pp 402ndash405 2009
[94] W-P Yin T-Z Zhao and H-Y Zhang ldquoA novel oligosaccha-ride ester from Syringa pubescensrdquo Journal of Asian NaturalProducts Research vol 10 no 1 pp 95ndash100 2008
[95] M Valko D Leibfritz J Moncol M T D Cronin M Mazurand J Telser ldquoFree radicals and antioxidants in normal physio-logical functions and human diseaserdquoThe International Journalof Biochemistry amp Cell Biology vol 39 no 1 pp 44ndash84 2007
[96] D Krishnaiah R Sarbatly and R Nithyanandam ldquoA review ofthe antioxidant potential of medicinal plant speciesrdquo Food andBioproducts Processing vol 89 no 3 pp 217ndash233 2011
[97] P Liu Y Hu D-H Guo et al ldquoAntioxidant activity ofoligosaccharide ester extracted from Polygala tenuifolia roots insenescence-accelerated micerdquo Pharmaceutical Biology vol 48no 7 pp 828ndash833 2010
[98] Y Hu H-B Liao G Dai-Hong P Liu Y-Y Wang and KRahman ldquoAntidepressant-like effects of 361015840-disinapoyl sucroseon hippocampal neuronal plasticity and neurotrophic signalpathway in chronically mild stressed ratsrdquo NeurochemistryInternational vol 56 no 3 pp 461ndash465 2010
[99] Y Hu H B O Liao P Liu D-H Guo and K RahmanldquoA bioactive compound from Polygala tenuifolia regulatesefficiency of chronic stress on hypothalamic-pituitary-adrenalaxisrdquo Pharmazie vol 64 no 9 pp 605ndash608 2009
[100] A Jungbauer and SMedjakovic ldquoAnti-inflammatory propertiesof culinary herbs and spices that ameliorate the effects ofmetabolic syndromerdquoMaturitas vol 71 no 3 pp 227ndash239 2012
Evidence-Based Complementary and Alternative Medicine 23
[101] Q Xu Y Wang S Guo Z Shen and L Yang ldquoAnti-inflammatory and analgesic activity of aqueous extract of Flospopulirdquo Journal of Ethnopharmacology vol 152 no 3 pp 540ndash545 2014
[102] K S Kim D S Lee G S Bae et al ldquoThe inhibition of JNKMAPK and NF-120581B signaling by tenuifoliside A isolated fromPolygala tenuifolia in lipopolysaccharide-induced macrophagesis associated with its anti-inflammatory effectrdquo European Jour-nal of Pharmacology vol 721 no 1ndash3 pp 267ndash276 2013
[103] J-G Lee J-M Yon C Lin A Y Jung K Y Jung and S-YNamldquoCombined treatment with capsaicin and resveratrol enhancesneuroprotection against glutamate-induced toxicity in mousecerebral cortical neuronsrdquo Food and Chemical Toxicology vol50 no 11 pp 3877ndash3885 2012
[104] M L Jin S Y Park Y H Kim J-I Oh S J Lee andG Park ldquoThe neuroprotective effects of cordycepin inhibitglutamate-induced oxidative andER stress-associated apoptosisin hippocampal HT22 cellsrdquo NeuroToxicology vol 41 pp 102ndash111 2014
[105] P Liu Y Hu J Li et al ldquoProtection of SH-SY5Y neuronal cellsfrom glutamate-induced apoptosis by 36rsquo-disinapoyl sucrosea bioactive compound isolated from radix polygalardquo Journal ofBiomedicine and Biotechnology vol 2012 Article ID 728342 5pages 2012
[106] P-B Li W-L Lin Y-G Wang W Peng X-Y Cai and W-WSu ldquoAntidiabetic activities of oligosaccharides of Ophiopogonisjaponicus in experimental type 2 diabetic ratsrdquo InternationalJournal of Biological Macromolecules vol 51 no 5 pp 749ndash7552012
[107] T Liu Y M Yip L Song et al ldquoInhibiting enzymatic starchdigestion by the phenolic compound diboside A a mechanisticand in silico studyrdquo Food Research International vol 54 no 1pp 595ndash600 2013
[108] F Cote andMGHahn ldquoOligosaccharins structures and signaltransductionrdquo Plant Molecular Biology vol 26 no 5 pp 1379ndash1411 1994
[109] RACreelman and J EMullet ldquoOligosaccharins brassinolidesand jasmonates nontraditional regulators of plant growthdevelopment and gene expressionrdquo Plant Cell vol 9 no 7 pp1211ndash1223 1997
[110] L Jiao D Wan X Zhang B Li H Zhao and S LiuldquoCharacterization and immunostimulating effects on murineperitoneal macrophages of oligosaccharide isolated from Panaxginseng CAMeyerrdquo Journal of Ethnopharmacology vol 144 no3 pp 490ndash496 2012
Submit your manuscripts athttpwwwhindawicom
Stem CellsInternational
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
MEDIATORSINFLAMMATION
of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Behavioural Neurology
EndocrinologyInternational Journal of
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Disease Markers
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
BioMed Research International
OncologyJournal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
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Oxidative Medicine and Cellular Longevity
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
PPAR Research
The Scientific World JournalHindawi Publishing Corporation httpwwwhindawicom Volume 2014
Immunology ResearchHindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Journal of
ObesityJournal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
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Computational and Mathematical Methods in Medicine
OphthalmologyJournal of
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Research and TreatmentAIDS
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Gastroenterology Research and Practice
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Parkinsonrsquos Disease
Evidence-Based Complementary and Alternative Medicine
Volume 2014Hindawi Publishing Corporationhttpwwwhindawicom
10 Evidence-Based Complementary and Alternative Medicine
Table2Con
tinued
Num
ber
Nam
eR 1
R 2R 3
R 4R 5
R 6R 7
R 8Source
Parts
Reference
102
Tenu
ifolisideB
FH
HH
KH
HH
Polyg
alatenu
ifolia
Roots
[4256]
103
Tenu
ifolisideC
KH
HH
LH
HH
Polyg
alatricornis
Polyg
alatenu
ifolia
Roots
[374256]
104
Heterosmilasid
eH
HI
HH
IH
HHeterosmila
xerythrantha
Aeria
lparts
[48]
105
Quiqu
esetinerviusideA
HI
HH
II
HH
Calamus
quiquesetin
ervius
Stem
s[70]
106
Quiqu
esetinerviusideB
AcI
HH
II
HH
Calamus
quiquesetin
ervius
Stem
s[70]
107
Quiqu
esetinerviusideC
HI
HAc
II
HH
Calamus
quiquesetin
ervius
Stem
s[70]
108
Quiqu
esetinerviusideD
AcG
HH
II
HH
Calamus
quiquesetin
ervius
Stem
s[70]
109
Quiqu
esetinerviusideE
HG
HAc
II
HH
Calamus
quiquesetin
ervius
Stem
s[70]
110
Vanicosid
eAI
HH
AcG
GH
G
Polyg
onum
sachalinensis
Polyg
onum
cuspidatum
Polyg
onum
hydropiper
Stem
sLeaves
Rhizom
es[51527172]
111
Vanicosid
eBI
HH
HG
GH
G
Polyg
onum
sachalinensis
Polyg
onum
cuspidatum
Persica
riahydropiper
Stem
sLeaves
Rhizom
es[4351527172]
112
Vanicosid
eDG
HH
HG
GH
GPersica
riahydropiper
Leaves
[51]
113
Vanicosid
eEI
AcH
AcG
GH
GPolyg
onum
hydropiper
Stem
sand
leaves
[72]
114
LapathosideA
IH
HH
GG
HI
Polyg
onum
sachalinensis
Polyg
onum
cuspidatum
Fagopyrum
dibotrys
Stem
sRh
izom
es[5173]
115
LapathosideC
IH
HH
GG
HH
Polyg
onum
sachalinensis
Polyg
onum
cuspidatum
Stem
s[4352]
116
DibosideA
GH
HH
GI
HG
Fagopyrum
tataric
umFagopyrum
dibotrys
Roots
Rhizom
es[57]
117
Hidropiperosid
eAI
HH
HH
GH
GPolyg
onum
hydropiper
Stem
sand
leaves
[72]
118
Hidropiperosid
eBI
HH
AcG
GH
IPolyg
onum
hydropiper
Stem
sand
leaves
[72]
119
Tataris
ideB
IH
HAc
GG
HAc
Fagopyrum
tataric
umRo
ots
[57]
Evidence-Based Complementary and Alternative Medicine 11
Table2Con
tinued
Num
ber
Nam
eR 1
R 2R 3
R 4R 5
R 6R 7
R 8Source
Parts
Reference
120
Tataris
ideC
IAc
HAc
GG
HAc
Fagopyrum
tataric
umRo
ots
[57]
121
Tataris
ideD
GH
HAc
GI
HH
Fagopyrum
tataric
umRo
ots
[57]
122
Tataris
ideF
GH
HH
II
HG
Fagopyrum
tataric
umRo
ots
[57]
123
310158406-O
-Di-sinapoylsu
crose
KH
HH
KH
HH
Polyg
alatricornis
Polygalahongkongensis
Polyg
alasib
irica
Polyg
alatenu
ifolia
Cynanchu
mam
plexica
ule
Roots
Root
barks
Who
leplants
Aeria
lparts
[37ndash394153ndash
566974]
124
661015840-O
-Di-c
oumaroylsu
crose
GH
HH
HG
HH
Bidens
parviflora
Who
leplants
[61]
125
11015840 3101584061015840-O
-Tri-
coum
aroyl-6
-feruloylsucrose
IH
HH
GG
HG
Fagopyrum
tataric
umRo
ots
[7576]
126
3101584061015840-O
-Di-c
oumaroyl-110158406-O
-di-
feruloylsucrose
IH
HH
GG
HI
Fagopyrum
tataric
umRo
ots
[7576]
127
31015840-O
-Cou
maroyl-11015840610158406-O
-tri-
feruloylsucrose
IH
HH
IG
HI
Fagopyrum
tataric
umRo
ots
[7576]
128
11015840 31015840610158406-O
-Tetra-fe
ruloylsucrose
IH
HH
II
HI
Fagopyrum
tataric
umRo
ots
[7576]
SeeS
chem
e2
12 Evidence-Based Complementary and Alternative Medicine
131130129
CH2OHOH
OH
OO
OH
C
C
HH
HHO
OO
O
HO
HOHO
HO
HOOH
OHOHOH
OHOH
HOO
O
O
O
HO
HO
OH
OHOHOH
OHOH
HOO
O
O
O
HO
Figure 3
12
3
4
5
6
1998400
2998400
3998400
4998400
5998400
6998400
HO
O
O
R1O
R2O
R8O
R7OOR3
OR4 OR5OR6
Scheme 2
antidepressant cytotoxic antineoplastic anti-inflammatoryantidiabetic plant growth-regulatory neuroprotective andcerebral protective activities Lignan-derived disaccharideesters phenylpropanoid-derived tetrasaccharide esters andpentasaccharide esterswith biological activities have not beenreported Aside from the isolated constituents oligosaccha-ride mixtures from Rehmannia glutinosa Panax ginseng andScrophularia ningpoensiswere also reported to display diversepharmacological activities such as antidiabetic immunopo-tentiating enhanced memory and antineoplastic activitiesThese active compounds and mixtures could serve as thevaluable candidates to be developed as possible drugs for thetreatment and prevention of diseases
31 Antioxidant Activity The adverse effects of oxidativestress proposed to play significant roles in the pathogenesis ofcardiovascular diseases atherosclerosis hypertension can-cer diabetes mellitus neurodegenerative diseases rheuma-toid arthritis ischemiareperfusion injury and ageing havebecome an inevitable and serious issue [95 96] Scientistshave thus made great efforts to explore antioxidants frommedicinal plants by using different kinds of assay methodswhich include DPPH radical scavenging assay hydroxylradical scavenging assay superoxide anion scavenging assayand ABTS radical scavenging method [96]
Lapathosides C and D hydropiperoside vanicoside Bhidropiperosides A and B lapathoside A and diboside Awere isolated from the Polygonum Persicaria and Fagopyrumgenera belonging to the Polygonaceae family The DPPH testrevealed that free radical-scavenging activity of the isolatedcompounds termed lapathoside C (115) hydropiperoside(42) vanicoside B (111) and lapathoside D (38) increasedin turn and lapathoside D exhibited strongest scavengingability with an IC
50of 0088 120583M [43] Hidropiperosides A
and B (117 118) were reported to show obvious antioxidantresponse to DPPH radicals with the SC
50values of 234
and 267 120583gmL respectively while vanicoside E moderatelyexhibited the same activity with a SC
50value of 490 120583gmL
[72] Lapathoside A (114) and diboside A (116) just showedlower antioxidant activities with the SC
50values of 19948 and
16552 120583M respectively [73]Smiglasides A and B smilaside P 26-di-acetyl-3101584061015840-
di-feruloylsucrose helonioside B smilasides GndashL and het-erosmilaside were isolated from the Heterosmilax and Smi-lax genera Compared with ascorbic acid (IC
5014352 120583M)
used as positive control smiglasides A and B and smi-laside P (48 49 65) (IC
5033958 33066 and 31449 120583M
resp) showed higher antioxidant activities than 26-di-acetyl-3101584061015840-di-feruloylsucrose (73) and helonioside B (40) (IC
50
63166 and 51827120583M resp) [47] Additionally Nhiem et alreported that helonioside B heterosmilaside (104) and 26-di-acetyl-3101584061015840-di-feruloylsucrose exhibited important DPPHradical scavenging activities with the SC
50values of 91 127
and 87 120583gmL respectively [48] Compared with smilasidesG-I (57ndash59) (ED
50685ndash794120583M) smilasides JndashL (60ndash62)
showed higher radical scavenging activities with an ED50
value of 267ndash327120583M [44]Five quiquesetinerviusides AndashE (105ndash109) isolated from
the Calamus genus showed weak DPPH scavenging activ-ities (IC
50604ndash1018120583M) but exhibited better hydroxyl
radical scavenging activities (IC50
36ndash84 120583M) Moreoverquiquesetinerviuside C showed superoxide anion scaveng-ing activity with an IC
50value of about 1843 120583M [70]
Liu et al investigated the antioxidant capacity of 310158406-O-di-sinapoylsucrose (DISS) (123) by using the acceleratedsenescence-prone short-lived mice (SAMP) in vivo Theanalyses indicated that the activities of antioxidant enzymesof SOD and glutathione peroxidase ascended obviously inSAMP mice when amended with DISS 50mgkg MoreoverDISS could downregulate and even restore the level ofmalondialdehyde in SAMP model group [97]
From the above studies it can be concluded that oligosac-charide esters with antioxidant activities have been identifiedin the Polygonaceae Liliaceae Smilacaceae and Arecaceaefamilies The results of the antioxidant assays show that theincreased number of phenolic hydroxyl groups and acetylgroups could produce higher antioxidant activity Fan etal indicated that the increased number of phenylpropanoidgroups was not beneficial to free radical scavenging activity[43] Zhang et al pointed out that oligosaccharide esters withferuloyl groups exhibited better antioxidant activities thanthose with coumaroyl groups [44]
Evidence-Based Complementary and Alternative Medicine 13
Table 3 Fatty acid-derived disaccharide esters
Number Name R1 R2 Source Parts Reference132 61015840-O-Linoleylsucrose H O Astragalus membranaceus Roots [77]133 61015840-O-Palmitoylsucrose H P Astragalus membranaceus Roots [77]134 6-O-Palmitoylsucrose P H Astragalus membranaceus Roots [77]
135 61015840-O-Linolenoylsucrose H N Astragalus membranaceusEquisetum hiemale
RootsAerial parts [77 78]
136 6-O-Linoleylsucrose O H Astragalus membranaceus Roots [77]137 6-O-Myristoylsucrose Q H Astragalus membranaceus Roots [77]
138 6-O-[(7Z10Z13Z)-Hexadeca-71013-trienoyl]sucrose H R Equisetum hiemale Aerial parts [78]
139 6-O-[(7Z10Z)-Hexadeca-710-dienoyl]sucrose H S Equisetum hiemale Aerial parts [78]
See Scheme 3
12
3
4
5
6
1998400
2998400
3998400
4998400
5998400
6998400
HO
O
O
R1O
R2O
R8O
R7OOR3
OR4 OR5OR6
O
O
O
18
18
1616
16
14
N linolenoyl
O linoleyl
P palmitoyl
Q myristoyl
O
O
O
R hexadeca-71013-trienoyl
S hexadeca-710-dienoyl
Scheme 3
32 Antidepressant Activity The oligosaccharides obtainedfrom the Morinda genus not only show specific antidepres-sant and antistress activities but also have no suppression orexcitatory effects on central nervous system as well Whatis more they can be taken orally with little toxicity [21]The inulin-type hexasaccharide (IHS) (9) from Morindaofficinalis obviously exhibited cytoprotective activity whichcontributed to the antidepressant effect not only by providingthe PC12 with protection against Cort-induced lesion withIHS 0625 and 125 120583Mbut also by reducing theCort-induced[Ca2+]
119894overloading with IHS 25 and 10 120583M IHS 5 and
10 120583Mupregulated the nerve growth factormRNAexpressionin Cort-induced PC12 cells [22] Polygalatenosides A (181)and B (182) were isolated from the Polygala genus Theysignificantly inhibited the isotope-labeled RTI-55 binding to
norepinephrine transporter protein with the IC50
values of300 and 604 120583M respectively [91]
DISS and tenuifoliside A were isolated from the PolygalaandCynanchum genera Liu et al investigated the antidepres-sant effect of YZ ethanol extract based on the tail suspensiontest (TST) and forced swimming test (FST) which arethe ease-of-use and widely-accepted models for estimatingantidepressant activities in mice The results indicated thatYZ-50 fraction at a dose of 200mgkgwas able to significantlydecrease the immobility time in TST Furthermore YZ-50possessed ability to inhibit corticosterone-induced injury ofhuman neuroblastoma SH-SY5Y cells What is more DISS(123) and tenuifoliside A (44) two major compounds of YZ-50 fraction showed effective protective response to the lesionin SY5Y cells [53] The antidepressant-like effect of DISS at
14 Evidence-Based Complementary and Alternative Medicine
H3CO
HO
HOHO
HO
HO
HO
HOHO
O O
OO O
OO
O
O
O
OO
O
O
OH
OH
OH
OH
OCH3
OCH3
CH2OH
CH2OH
CH2OAc
CH2OAc
H3CO
HOHO
HO
O
O
O
OO
O
O
OH
OH
OH
OCH3
CH2OH
CH2OH
H3CO
H3CO H3CO
HOHO
HO
O
O
O
OO
O
O
OH
OH
OH
OCH3
CH2OH
CH2OAc
CH3O
H
HOHO
HO
HO
HOO O
OO O
OO
OH
OCH3
CH2OHCH2OH
H3CO H3CO
H
CH2CH2 HO
HO
HO
HO
HOO O
OO O
OO
OH
OCH3
CH2OHCH2OAc
H3CO
H
CH2
140 141 142
143 144 145
Figure 4
Table 4 Phenylpropanoid-derived trisaccharide esters
Number Name R1 R2 R3 R4 R5 R6 R7 Source Parts Reference146 Tricornose C K H H H H L H Polygala tricornis Roots [37]147 Tricornose D K H H H H K H Polygala tricornis Roots [37]148 Tricornose E K H H H K L H Polygala tricornis Roots [37]149 Tricornose F K H H H I L H Polygala tricornis Roots [37]See Scheme 4
O
OOO
O
R2O
R4O
R3O
R6O
OH
OH
OH
OH
OR1
OR5CH2OR7
Scheme 4
the doses of 5 10 and 20mgkg was also tested in chronicallymild stressed rats DISS was able to exhibit antidepressantactivity by upregulating the expression of noradrenergic-regulated plasticity genes including cell adhesion moleculeL1 brain-derived neurotrophic factor laminin and cAMP
response element binding protein factor in hippocampus[98] DISS improved the reward reaction by increasingsucrose intake and obviously decreased the levels of serumcortisol adrenocorticotrophic hormone and corticotropin-releasing factor Further DISS played an enhanced role inthe expression of mineralocorticoid receptor together withglucocorticoid receptor mRNA [99]
33 Cytotoxic and Antineoplastic Activities Smilasides AndashFand P smiglasides A and B smilaside P and helonioside Awere isolated from the Smilax Trillium and Paris generaKuo et al obtained smilasides AndashF (51ndash56) and evaluatedtheir cytotoxicity against human tumor cell lines comprisinghuman oral epithelium carcinoma (KB) human cervicalcarcinoma (Hela) human colon tumor (DLD-1) humanbreast adenocarcinoma (MCF-7) human lung carcinoma (A-549) and humanmedulloblastoma (Med) cells byMTTassayExperimental data indicated that all but smilaside C showedcytotoxicity against three to six human tumor cell lines(ED50
= 51ndash130 120583gmL) and smilasides DndashF (ED50
= 27ndash50 120583gmL) displayed strong cytotoxic activities against DLD-1 cells [46]Wang et al reported the antitumor constituents of
Evidence-Based Complementary and Alternative Medicine 15
OH
OH
OH
OH
OH
OHOH
OHOH
OHOH
OH
OHOHOH
OH
OH
OH
OHOH
OH
OH
OHOH
H
H H
HO
O
O
O
O
O
O
O
OO
OO
O
OO
O
HO
HO
HO
OO
O
O
OO
OO
O
OO
O
OO
O
OO
O
O
O
OO
O
O
OO
O
OO
OOOO
HO
HO
HO
HO
HO
HO
HO
HO
HO
HO
HOHO
HO
HO
HO
HO
HO
150 151 152
153 180
AcO
AcO
AcOAcO
OAc
OAc
CH2OH
OHOH
OH OHOH
OHOH
OH
OHOH
CH3O
Figure 5
Table 5 Phenylpropanoid-derived tetrasaccharide esters
Number Name R1 R2 R3 Source Parts Reference154 Tricornose G K H K Polygala tricornis Roots [37]155 Tricornose H K K K Polygala tricornis Roots [37]156 Tricornose I K K L Polygala tricornis Roots [37]157 Tricornose J K I L Polygala tricornis Roots [37]158 Tricornose K K I K Polygala tricornis Roots [37]159 Tricornose L K G K Polygala tricornis Roots [37]See Scheme 5
Smilax riparia including smiglasides A (48) and B (49) 26-di-acetyl-3101584061015840-di-feruloylsucrose (73) helonioside B (40)and smilaside P (65) Only smiglasidesA andB and smilasideP exhibited cytotoxicity against human tumor cell lines withdifferent inhibitory concentrations comparing with cisplatinand paclitaxel as positive controls [47] Helonioside A (39)exhibited higher cytotoxicity with the increase of concentra-tion (01ndash100120583gmL) [45] Tatarisides AndashG (45 119ndash121 46122 47) and diboside A (116) from the Fagopyrum genusexerted cytotoxic activities against different human cell linesand the cytotoxicity of tatariside C was the most remarkablewith the IC
50values ranging from 644 to 749 120583gmL [57]
11015840236-O-Tetra-acetyl-31015840-O-cis-feruloylsucrose (95) fromthe Sparganium plants exhibited extremely weak cyto-toxicity against the growth of mice Lung Adenocarcinoma
795 cell lines with an IC50
value of 116 120583gmL [66] SnS-2oligosaccharides mixture including raffinose (3) stachyose(19) and verbascose (21) from the roots of Scrophularianingpoensis had antitumor activity against the growth ofLewis pulmonary carcinoma cells transplanted into mice[18]
Disaccharide esters and oligosaccharides mixture fromthe Liliaceae Polygonaceae Sparganiaceae and Scrpophular-iaceae families showed effective cytotoxic and antineoplasticactivities The study results indicated that feruloyl and acetylgroups play an important role in mediating cytotoxicitywhich seems to be related to the substitution position offeruloyl groups The feruloyl groups at C-6 or C-11015840 are vitalfor cytotoxicity In addition the increased number of acetylgroups could induce higher tumoricidal activity
16 Evidence-Based Complementary and Alternative Medicine
Table 6 Phenylpropanoid-derived pentasaccharide esters
Number Name R1 R2 R3 R4 R5 R6 Source Parts Reference160 Tenuifoliose A G D I Ac Ac Ac Polygala tenuifolia Roots [38 42]161 Tenuifoliose B G D I H Ac Ac Polygala tenuifolia Roots [42]162 Tenuifoliose C G D I H H H Polygala tenuifolia Roots [42]163 Tenuifoliose F G D U Ac Ac Ac Polygala tenuifolia Roots [42]164 Tenuifoliose G G D U Ac H Ac Polygala tenuifolia Roots [42]165 Tenuifoliose H G D G Ac Ac Ac Polygala tenuifolia Roots [38 42 79]166 Tenuifoliose I G D G Ac H Ac Polygala tenuifolia Roots [42 79]167 Tenuifoliose J G D G H Ac Ac Polygala tenuifolia Roots [42]168 Tenuifoliose K G D G H H Ac Polygala tenuifolia Roots [42]169 Tenuifoliose L G D T Ac Ac Ac Polygala tenuifolia Roots [42 79]170 Tenuifoliose M G D T Ac H Ac Polygala tenuifolia Roots [42]171 Tenuifoliose N I D I Ac Ac Ac Polygala tenuifolia Roots [42]172 Tenuifoliose O I D I H Ac Ac Polygala tenuifolia Roots [42]173 Tenuifoliose P I D I H H Ac Polygala tenuifolia Roots [42]174 Tenuifoliose Q G D T H Ac Ac Polygala tenuifolia Roots [79]175 Tenuifoliose S G D G H H H Polygala tenuifolia Roots [42]176 Tenuifoliose T G D I H H H Polygala tenuifolia Roots [42]177 Tenuifoliose V H D I Ac Ac Ac Polygala tenuifolia Roots [42]178 Tenuifoliose W I D U Ac H Ac Polygala tenuifolia Roots [42]179 Tenuifoliose X I D I H H H Polygala tenuifolia Roots [42]See Scheme 6
O
OO
O
O
O
O
OR1
OH
OH
OH
OHOH
OH
HOHO
HO
HO
OR2
R3O
CH2OH
Scheme 5
34 Anti-Inflammatory Activity Inflammation an importantbasic pathological process is a defense response of biopsywith vascular system to damage stimuli such as pathogensimpaired cells and tissues and physical and chemical factorsHowever if the process of inflammatory response cannot endnormally when cell debris and pathogens were cleared thebiological defence response will become causative factor andbring about many diseases such as diabetes cardiovasculardiseases metabolic syndrome and cancer [100 101]
Tenuifoliside A (44) from the Polygala genus exhibitedstrong anti-inflammatory effect not only by suppressing the
production of NO but also by reducing the production ofiNOS prostaglandin E2 cyclooxygenase-2 and proinflam-matory cytokines through the inhibition of the mitogen-activated protein kinases pathway and NF-120581B pathway [102]The anti-inflammatory activities of quiquesetinerviusides D(108) and E (109) from the Calamus genus were evaluated inRAW 2647 cells Both of them showed significant inhibitoryeffects against the production of LPS-stimulated NOwith theIC50values of 90ndash295120583M [70]Six disaccharide fatty acid esters (132ndash137) were iso-
lated from the Astragalus and Equisetum genera The anti-inflammatory effects of these isolated compounds have alsobeen documented The activation of NF-120581B could upregulatethe expression of proinflammatory cytokines inducible nitricoxide synthase (iNOS) and tumornecrosis factor alpha (TNF-120572) The NF-120581B inhibitory activities of compounds 132ndash137were tested in HepG2 cells stimulated with TNF-120572 All ofthese compounds could significantly restrainTNF-120572-inducedNF-120581B transcriptional activities with the IC
50values of 44ndash
247 120583M Li et al pointed out that olefinic bonds and thelength of the fatty acid moieties contributed to the NF-120581B inhibitory activity Furthermore the inhibition increasedsignificantly with the increase of the number of olefinic bondson the aliphatic moiety [77] These results may provide ascientific basis for the development of new anti-inflammatoryagents
35 Neuroprotective and Cerebral Protective Activities Aswe all know glutamate works as a major excitatory aminoacid neurotransmitter in the mammalian central nervous
Evidence-Based Complementary and Alternative Medicine 17
R6O
R2O
OR3
OR5
OR4
CH2OR1
OCH3
Rham
OO
O
OO O
O
O
O
OO
RhamO
O
OH
OH
OHOH
OH
OHOH
OHHO
HO
HO
T O-rhamnosyl-coumaroyl U O-rhamnosyl-feruloyl
Scheme 6
system and plays a crucial role in several physiological pro-cesses [103] However the accumulation of glutamate inducesdiverse acute and chronic neurodegenerative diseases suchas epilepsy ischemic stroke and Parkinsonrsquos disease aswell as Alzheimerrsquos disease [104] DISS (123) isolated fromthe Polygala genus exhibited neuroprotective effect againstglutamate-induced SH-SY5Y neuronal cell damage The invitro test demonstrated that DISS (06 6 and 60 120583molL)played a critical role in increasing cell viability controllinglactate dehydrogenase and attenuated apoptosis ranging from195 to 258 [105]
Tenuifoliside B (102) from the Polygala genus was ableto significantly shorten the coma time of KCN-inducedanoxia mice at the doses of 3 and 10mgkg and it playedan important role in ameliorating the scopolamine-inducedimpairment of performance in passive avoidance task inrats and enhancing the tremors induced by oxotremorine inmiceThese results together demonstrated that tenuifoliside Bpossessed cognitive improving and cerebral protective effects[56]
36 Antidiabetic Activity Diabetes mellitus a chronic debil-itating metabolic disease is characterized by high bloodglucose content and comprises three types termed type Itype II and gestational diabetes [106] Stachyose (19) extract(a part) from Rehmannia glutinosa obviously exhibited theactivity of downregulating fasting plasma glucose level andpartially keeping from hyperglycemia induced by adrenalineand glucose without obvious dose-dependent effect Otherthan that in vivo tests in rats induced by alloxan revealed
that stachyose extract at the dose of 200mgkg significantlydecreased blood-sugar level [15]
Diboside A lapathosides C and D vanicosides A andB and hydropiperoside were isolated from the FagopyrumPolygonum and Persicaria genera belonging to the Polygo-naceae family Diboside A (116) could potentially inhibit 120572-amylase activity with an IC
50of 269 120583M and thus retard the
starch digestion rate which is helpful for diabetic individualsin controlling blood sugar level [107] Lapathoside D (38)exerted stronger activity of 120572-glucosidase inhibition with anIC50
value of 0113mM than acarbose which was chosen asa positive drug for the treatment of type II diabetes [43]Vanicoside B (111) was reported to have higher 120573-glucosidaseinhibitory activity with an IC
50of 505 120583M than vanicoside A
(110) with an IC50of 599 120583M because of the acetyl moiety of
the latter possibly decreasing inhibitory activity of vanicosideA [71]
Fujimoto et al investigated the inhibitory effects ofmumeoses FndashO (83ndash92) from the Prunus genus on aldosereductase and discovered that caffeoyl groups are crucialfor the inhibitory effect on aldose reductase And thusmumeoses F G H J K L M and N (IC
50= 22ndash77120583M) with
a coumaroyl group and acetyl groups inhibited moderatelyaldose reductase from reducing glucose to sorbitol whichis associated with the chronic complications of diabetes [6364]
37 Elicitors and Regulators Oligosaccharides are quitepropitious for encoding biological information because ofdiverse monosaccharide units and complex molecular struc-tures and they are therefore first described as biological
18 Evidence-Based Complementary and Alternative Medicine
181 H
H
H
H
H
H
H
H
H H
H
H
H
H
H
H
H H
HH
Benzyl
Benzyl
Benzyl
182
183
184 Ac
Ac
Ac
Ac
Ac
Ac
Ac
Ac
Ac
Ac
185
186
187
188
189
R1 R2 R3
R1 R2 R3 R4
OCH3
R3OH2C OR2
OR1
OR1
O
O
O
O O
OOO
O
OO
O
OH
OH
OH OH
OH
O O
O
O
OH
HO
OH
OH OHOH
OH
OH
OHHO
HO
OH
OH
HO
CH2OH
CH2OH
CH2OH
CH2OH
C
R2O
R3O
CH2OR4
CH2CH2 CH2CH2CH2CH2CH3
CH3
CH3
191190 192
193
O
C C
O
OO
OO
OO
OO
O O
O
O
O
O
O
O
OH
OH
OHHO
HO
HOOH
OH
OH
OH
HO
OH
OH
OH
OH
HO
HO
C C
R998400O
R998400
Figure 6
signals in plants [108] Oligosaccharides from the cell wallfragments of plants and fungi are powerful signal moleculessuch as the elicitors of plant defence response and theregulators of plant growth and they are capable of exertingbiological activities at exceedingly low concentrations [109]Heptasaccharide (HS) (15) and octasaccharide (OS) (16) iso-lated from the Paris genus possessed plant growth-regulatory
activities [29 30]The two oligosaccharides significantly pro-moted the proliferation of Paris polyphylla var yunnanensisroots at the doses of 25ndash20mgL The octasaccharide hadthe most obvious effect on the growth of Panax japonicusvar major hairy roots at a dose of 30mgL while the otherhad the most positive effect on saponin accumulation ofPanax japonicus var major hairy roots at a dose of 10mgL
Evidence-Based Complementary and Alternative Medicine 19
[29] Similarly Zhou et al evaluated the stimulating effectsof HS and OS on the root growth and saponin productionof Panax ginseng hairy roots which were induced from theplant roots infected withAgrobacterium rhizogenes strain A4The results showed that there was a maximum effect on thehairy roots growth and saponin accumulation on day 10Compared with control group the root biomass dry weightwas increased by more than 17-fold while the total saponincontent of roots increased by more than 1-fold when thesetwo oligosaccharides were added to the hairy root at a dose of30mgL [30] The above data illustrate that HS and OS couldserve as the plant growth-regulators not only in their originalspecies but also in others
38 Immunopotentiating Activity Macrophages are impor-tant targets of investigations on cytophagy cellular immunityand molecular immunology Therefore they are deemedto play a vital role in host defense comprising phagocy-tosis proteolytic processing pathogenic agent apoptosiscytokines production and foreign antigens presentation[110] The water-extracted oligosaccharides from Panax gin-seng (WGOS) exhibited better immunopotentiating activ-ity by increasing phagocytic function of macrophages andpromoting NO TNF-120572 and reactive oxygen species pro-duction [110] In addition Wan et al have obtained malto-oligosaccharides (17 119899 = 3sim8) and three oligosaccharides (213 14) from the Panax ginseng roots The in vitro bioassaypointed out thatWGOS could serve as efficacious stimulatorsof B and T lymphocytes [28] These studies provided enlight-enment that the mixture of oligosaccharides from Chineseherbalmedicine exhibits significant effect on immune system
39 Others Acetylcholinesterase (AChE) inhibitors showgood therapeutic effects onmyasthenia gravis glaucoma andAlzheimerrsquos disease through reversible enzyme inhibitionso as to increase the accumulation of acetylcholine in thesynapse and then promote and prolong the function ofacetylcholine Vanicoside B (111) showed AChE inhibitoryactivity with an IC
50of 0062mM while hydropiperoside
(42) and lapathosides C (115) and D (38) just exhibited weakenzyme inhibitory activity [43]
Wang et al has explored low molecular mass carbohy-drate polymer from Panax ginseng roots and obtained 30ethanol elution (PGO)which included peptides and oligosac-charides (17 119899 = 0sim5) identified as maltose maltotriosemaltotetraose maltopentaose maltohexaose and maltohep-taose Pharmacological experiments revealed that PGO couldsignificantly enhance the memory in scopolamine-inducedmemory deficit rats [27]
Cistanoside F (129) and kankanose (150) were isolatedfrom the Cistanche Paulownia and Acanthus genera Phar-macological experiments showed that cistanoside F andkankanose significantly exhibited vasorelaxant effects on thenoradrenaline-induced contraction of thoracic aorta fromrats [80]
4 Conclusion
Traditional Chinese medicine from natural kingdom playsan indelible role in the treatment of human diseases andit has aroused the attention of those who have engagedin medicinal pharmaceutical chemistry Therefore scientistshave made great contributions day after day to investigate thevalid chemicals from traditional Chinese medicines In thepast decades about 193 oligosaccharides and their esters havebeen identified from traditional Chinese medicinal plantsOn the one hand only a few oligosaccharides and theirmixtures were investigated and just exhibited antidepres-sant antineoplastic antidiabetic plant growth-regulatoryimmunopotentiating and enhancedmemory activitiesMoreexploratory work is still needed to excavate biological andpharmacological activities of oligosaccharides On the otherhand oligosaccharide esters exhibited multi-advantageousactivities Bioassays have revealed that antioxidant cytotoxicantineoplastic and anti-inflammatory activities are the mostnotable bioactivities Of course to search for the naturalproducts with these activities is a hotpot in the contemporarydrug research Oligosaccharide esters provide a vast treasuretrove for medical researchers After considering the currentstudies it should be taken as future directions to makemore mechanism of action studies and clinical trials tofurther evaluate its potential as new drugs Moreover thestructure-activity relationships discussed in this review willprovide reference information for further exploring theirrelationships and continually discovering the new bioactiveoligosaccharide esters
Conflict of Interests
The authors declare that there is no conflict of interestsregarding the publication of this paper
References
[1] X D Yang L J Zhang B Liang L Z Xu and S L YangldquoOligosaccharide esters isolated from plants of PolygalaceaerdquoChinese Traditional and Herbal Drugs vol 33 no 10 pp 954ndash958 2002
[2] N Ogwuru and M Adamczeski ldquoBioactive natural productsderived from Polygonum species of plants their structures andmechanisms of actionrdquo Studies in Natural Products Chemistryvol 22 pp 607ndash642 2000
[3] S Kobayashi T Miyase and H Noguchi ldquoPolyphenolic glyco-sides and oligosaccharide multiesters from the roots of Polygaladalmaisianardquo Journal of Natural Products vol 65 no 3 pp 319ndash328 2002
[4] M Takasaki S Kuroki M Kozuka and T Konoshima ldquoNewphenylpropanoid esters of sucrose from Polygonum lapathi-foliumrdquo Journal of Natural Products vol 64 no 10 pp 1305ndash1308 2001
[5] M L Zimmermann and A T Sneden ldquoVanicosides A and Bprotein kinase C inhibitors from Polygonum pensylvanicumrdquoJournal of Natural Products vol 57 no 2 pp 236ndash242 1994
[6] M Takasaki T Konoshima S Kuroki H Tokuda and HNishino ldquoCancer chemopreventive activity of phenylpropanoid
20 Evidence-Based Complementary and Alternative Medicine
esters of sucrose vanicoside B and lapathoside A from Poly-gonum lapathifoliumrdquo Cancer Letters vol 173 no 2 pp 133ndash138 2001
[7] Q Fu T Liang Z Y Li et al ldquoSeparation of carbohydrates usinghydrophilic interaction liquid chromatographyrdquo CarbohydrateResearch vol 379 pp 13ndash17 2013
[8] M F Mrozek D Zhang and D Ben-Amotz ldquoOligosaccharideidentification and mixture quantification using Raman spec-troscopy and chemometric analysisrdquo Carbohydrate Researchvol 339 no 1 pp 141ndash145 2004
[9] G S Armstrong and B Bendiak ldquoHigh-resolution four-dimen-sional carbon-correlated 1H-1H ROESY experiments employ-ing isotags and the filter diagonalization method for effectiveassignment of glycosidic linkages in oligosaccharidesrdquo Journalof Magnetic Resonance vol 181 no 1 pp 79ndash88 2006
[10] G S Armstrong V A Mandelshtam A J Shaka and BBendiak ldquoRapid high-resolution four-dimensional NMR spec-troscopy using the filter diagonalization method and its advan-tages for detailed structural elucidation of oligosaccharidesrdquoJournal of Magnetic Resonance vol 173 no 1 pp 160ndash168 2005
[11] H-M Tseng S Gattolin J Pritchard H J Newbury and DA Barrett ldquoAnalysis of mono- di- and oligosaccharides by CEusing a two-stage derivatization method and LIF detectionrdquoElectrophoresis vol 30 no 8 pp 1399ndash1405 2009
[12] N Li X Li B L Hou and D L Meng ldquoNew disaccharosidefrom Camptosorus sibiricus Ruprrdquo Natural Product Researchvol 22 no 15 pp 1379ndash1383 2008
[13] Z Zhang D Wang Y Zhao H Gao Y-H Hu and J-FHu ldquoFructose-derived carbohydrates from Alisma orientalisrdquoNatural Product Research vol 23 no 11 pp 1013ndash1020 2009
[14] X Yang Y Zhao N He and K D Croft ldquoIsolation char-acterization and immunological effects of 120572-galacto-oligo-saccharides from a new source the herb Lycopus lucidus TurczrdquoJournal of Agricultural and Food Chemistry vol 58 no 14 pp8253ndash8258 2010
[15] R X Zhang Z P Jia L Y Kong et al ldquoStachyose extractfrom Rehmannia glutinosa Libosch to lower plasma glucose innormal and diabetic rats by oral administrationrdquo Pharmazievol 59 no 7 pp 552ndash556 2004
[16] R Zhang Y Zhao Y Sun X Lu and X Yang ldquoIsolationcharacterization and hepatoprotective effects of the raffinosefamily oligosaccharides from Rehmannia glutinosa liboschrdquoJournal of Agricultural and Food Chemistry vol 61 no 32 pp7786ndash7793 2013
[17] H Li F Song Z Zheng Z Liu and S Liu ldquoCharacterization ofsaccharides and phenolic acids in the Chinese herb Tanshen byESI-FT-ICR-MS and HPLCrdquo Journal of Mass Spectrometry vol43 no 11 pp 1545ndash1552 2008
[18] J E Deng J Zhang XM ChenW Ke and G Y Tian ldquoStudieson the physicochemical properties structure and antitumoractivity of an oligosaccharide homologue SnS-2 from the root ofScrophularia ningpoensis Hemslrdquo Chinese Journal of Chemistryvol 22 no 5 pp 492ndash497 2004
[19] S C Chou LM Chuang and S S Lee ldquoHypoglycemic constit-uents of gynura divaricata subsp formosanardquo Natural ProductCommunications vol 7 no 2 pp 221ndash222 2012
[20] F Feng L-L Wang X-P Lai Y-B Li Z-M Cao and Y-J Zhou ldquoStudy on oligosaccharides from Morinda officinalisrdquoJournal of Chinese Medicinal Materials vol 35 no 8 pp 1259ndash1262 2012
[21] Y F Li Z H Gong M Yang Y M Zhao and Z P Luo ldquoInhibi-tion of the oligosaccharides extracted fromMorinda officinalis
a Chinese traditional herbal medicine on the corticosteroneinduced apoptosis in PC12 cellsrdquo Life Sciences vol 72 no 8 pp933ndash942 2003
[22] Y-F Li Y-Q Liu M Yang et al ldquoThe cytoprotective effect ofinulin-type hexasaccharide extracted from Morinda officinalison PC12 cells against the lesion induced by corticosteronerdquo LifeSciences vol 75 no 13 pp 1531ndash1538 2004
[23] D N Olennikov L M Tankhaeva and A V Rokhin ldquoGlu-cofructans from Saussurea lappa rootsrdquo Chemistry of NaturalCompounds vol 47 no 3 pp 339ndash342 2011
[24] S K Hyun H A Jung B S Min J H Jung and J S ChoildquoIsolation of phenolics nucleosides saccharides and an alkaloidfrom the root of Aralia cordatardquo Natural Product Sciences vol16 no 1 pp 20ndash25 2010
[25] Z J Xu C W Lin and M F Liao ldquoStructure analysis of a newoligosaccharides BROS from Blumea ripariardquo Chinese Journalof Organic Chemistry vol 31 no 11 pp 1811ndash1819 2011
[26] Z J Xu C W Lin and Y Shi ldquoIsolation and structuredetermination of a new oligosaccharide from Blume ripariardquoJournal of Medicinal Plants Research vol 5 no 14 pp 2956ndash2962 2011
[27] Y Wang R Z Jiang G R Li et al ldquoStructural and enhancedmemory activity studies of extracts from Panax ginseng rootrdquoFood Chemistry vol 119 no 3 pp 969ndash973 2010
[28] DWan L Jiao H Yang and S Liu ldquoStructural characterizationand immunological activities of the water-soluble oligosaccha-rides isolated from thePanax ginseng rootsrdquoPlanta vol 235 no6 pp 1289ndash1297 2012
[29] L G Zhou C Z Yang J Q Li S L Wang and J Y WuldquoHeptasaccharide and octasaccharide isolated from Paris pol-yphylla var yunnanensis and their plant growth-regulatoryactivityrdquo Plant Science vol 165 no 3 pp 571ndash575 2003
[30] L G Zhou X D Cao R F Zhang Y L Peng S J Zhao andJ Y Wu ldquoStimulation of saponin production in Panax ginsenghairy roots by two oligosaccharides from Paris polyphylla varyunnanensisrdquo Biotechnology Letters vol 29 no 4 pp 631ndash6342007
[31] M Vanhaecke W van den Ende E Lescrinier and N Dyu-bankova ldquoIsolation and characterization of a pentasaccharidefrom Stellaria mediardquo Journal of Natural Products vol 71 no 11pp 1833ndash1836 2008
[32] J Feng and W Zhao ldquoComplete 1Hand 13C NMR assignmentsof four new oligosaccharides and two new glycosides fromPeriploca forrestiirdquoMagnetic Resonance in Chemistry vol 47 no8 pp 701ndash705 2009
[33] J Q Feng R J Zhang Y Zhou et al ldquoImmunosuppressive preg-nane glycosides from Periploca sepium and Periploca forrestiirdquoPhytochemistry vol 69 no 15 pp 2716ndash2723 2008
[34] X H Long R Xu Y H Zhang X H Tan andQ Y Sun ldquoA newoligosaccharide from Periploca calophyllardquo Zhongguo ZhongyaoZazhi vol 37 no 2 pp 226ndash229 2012
[35] L Wang Z-Q Yin Y Wang X-Q Zhang Y-L Li and W-CYe ldquoPerisesaccharides A-E new oligosaccharides from the rootbarks ofPeriploca sepiumrdquoPlantaMedica vol 76 no 9 pp 909ndash915 2010
[36] T Lei L Zhang H-Y Jiang Y Hu A-H Hong and Y-Z CenldquoA new pregnane glycoside and oligosaccharide from Parabar-ium huaitingiirdquo Journal of Asian Natural Products Research vol13 no 11 pp 1030ndash1035 2011
[37] J Li Y Jiang and P F Tu ldquoTricornoses A-L oligosaccharidemulti-esters from the roots of Polygala tricornisrdquo Journal ofNatural Products vol 68 no 5 pp 739ndash744 2005
Evidence-Based Complementary and Alternative Medicine 21
[38] H H Tu P Liu L Mu et al ldquoStudy on antidepressant com-ponents of sucrose ester from Polygala tenuifoliardquo ZhongguoZhongyao Zazhi vol 33 no 11 pp 1278ndash1280 2008
[39] G M She Y Y Ba Y Liu H Lv W Wang and R B ShildquoAbsorbable phenylpropenoyl sucroses from Polygala tenuifo-liardquoMolecules vol 16 no 7 pp 5507ndash5513 2011
[40] J Yong and P F Tu ldquoStudies on the chemical constituents inroot bark of Polygala tenuifolia (II)rdquo China Journal of ChineseMateria Medica vol 29 no 8 pp 751ndash753 2004
[41] M Ono C Takamura F Sugita et al ldquoTwo new steroidglycosides and a new sesquiterpenoid glycoside from theunderground parts of Trillium kamtschaticumrdquo Chemical andPharmaceutical Bulletin vol 55 no 4 pp 551ndash556 2007
[42] Y Ling Z Li M Chen Z Sun M Fan and C HuangldquoAnalysis and detection of the chemical constituents of RadixPolygalae and their metabolites in rats after oral administrationby ultra high-performance liquid chromatography coupledwith electrospray ionization quadrupole time-of-flight tandemmass spectrometryrdquo Journal of Pharmaceutical and BiomedicalAnalysis vol 85 pp 1ndash13 2013
[43] P Fan L Terrier A-E Hay A Marston and K HostettmannldquoAntioxidant and enzyme inhibition activities and chemicalprofiles ofPolygonum sachalinensis FSchmidt exMaxim (Polyg-onaceae)rdquo Fitoterapia vol 81 no 2 pp 124ndash131 2010
[44] L J Zhang C C Liao H C Huang Y C Shen L M Yangand Y H Kuo ldquoAntioxidant phenylpropanoid glycosides fromSmilax bracteatardquo Phytochemistry vol 69 no 6 pp 1398ndash14042008
[45] L L Yan W Y Gao Y J Zhang and Y Wang ldquoA new phenyl-propanoid glycosides from Paris polyphylla var yunnanensisrdquoFitoterapia vol 79 no 4 pp 306ndash307 2008
[46] Y H Kuo Y W Hsu C C Liaw J K Lee H C Huang andL M Y Kuo ldquoCytotoxic phenylpropanoid glycosides from thestems of Smilax chinardquo Journal of Natural Products vol 68 no10 pp 1475ndash1478 2005
[47] W-X Wang T-X Li H Ma J-F Zhang and A-Q JialdquoTumoral cytotoxic and antioxidative phenylpropanoid glyco-sides in Smilax riparia A DCrdquo Journal of Ethnopharmacologyvol 149 no 2 pp 527ndash532 2013
[48] N X Nhiem P vanKiem C vanMinh et al ldquoPhenylpropanoidglycosides fromHeterosmilax erythrantha and their antioxidantactivityrdquo Archives of Pharmacal Research vol 32 no 10 pp1373ndash1377 2009
[49] Y Wang W Y Gao T J Zhang and Y Q Guo ldquoA novelphenylpropanoid glycosides and a new derivation of phenolicglycoside from Paris Polyphylla var yunnanensisrdquo ChineseChemical Letters vol 18 no 5 pp 548ndash550 2007
[50] J-Y Zhang Y-Z Wang Y-L Zhao et al ldquoPhytochemicals andbioactivities of Paris speciesrdquo Journal of Asian Natural ProductsResearch vol 13 no 7 pp 670ndash681 2011
[51] N H N Hashim F Abas K Shaari and N H Lajis ldquoLC-DAD-ESIMSMS characterization of antioxidant and anti-cholinesterase constituents present in the active fraction fromPersicaria hydropiperrdquo LWT Food Science and Technology vol46 no 2 pp 468ndash476 2012
[52] PH FanA EHayAMarstonHX Lou andKHostettmannldquoChemical variability of the invasive neophytes Polygonumcuspidatum Sieb and Zucc and Polygonum sachalinensis FSchmidt ex Maximrdquo Biochemical Systematics and Ecology vol37 no 1 pp 24ndash34 2009
[53] P Liu Y Hu D H Guo et al ldquoPotential antidepressantproperties of Radix Polygalae (Yuan Zhi)rdquo Phytomedicine vol17 no 10 pp 794ndash799 2010
[54] J F Wu S B Chen S L Chen and P F Tu ldquoThe chemical con-stituents of Polygala hongkongensisHemslrdquoActa PharmaceuticaSinica vol 42 no 7 pp 757ndash761 2007
[55] Y Song Y Jiang D Bi X Tian L Liang and P Tu ldquoChemicalconstituents from n-butanol extract of aerial part of Polygalasibiricardquo Zhongguo Zhongyao Zazhi vol 37 no 4 pp 471ndash4742012
[56] Y Ikeya S Takeda M Tunakawa et al ldquoCognitive improvingand cerebral protective effects of acylated oligosaccharides inPolygala tenuifoliardquo Biological and Pharmaceutical Bulletin vol27 no 7 pp 1081ndash1085 2004
[57] C J Zheng C L Hu X Q Ma C Peng H Zhang and L PQin ldquoCytotoxic phenylpropanoid glycosides from Fagopyrumtataricum (L) Gaertnrdquo Food Chemistry vol 132 no 1 pp 433ndash438 2012
[58] X Li Y F Zhang L Yang et al ldquoChemical profiling ofconstituents of Smilacis glabrae using ultra-high pressure liquidchromatography coupled with LTQ orbitrap mass spectrome-tryrdquo Natural Product Communications vol 7 no 2 pp 181ndash1842012
[59] T-T Sun D-W Zhang Y Han F-Y Dong andWWang ldquoSmi-lasides M and N two new phenylpropanoid glycosides fromSmilax ripariardquo Journal of Asian Natural Products Research vol14 no 2 pp 165ndash170 2012
[60] J Li X Bi G Zheng Y Hitoshi T Ikeda and T NoharaldquoSteroidal glycosides and aromatic compounds from Smilaxripariardquo Chemical amp Pharmaceutical Bulletin vol 54 no 10 pp1451ndash1454 2006
[61] N Wang X Yao R Ishii and S Kitanaka ldquoBioactive sucroseesters from Bidens parviflorardquo Phytochemistry vol 62 no 5 pp741ndash746 2003
[62] S Nakamura K Fujimoto T Matsumoto et al ldquoAcylatedsucroses and acylated quinic acids analogs from the flower budsof Prunus mume and their inhibitory effect on melanogenesisrdquoPhytochemistry vol 92 pp 128ndash136 2013
[63] K Fujimoto SNakamura TMatsumoto et al ldquoMedicinal flow-ers XXXVIII Structures of acylated sucroses and inhibitoryeffects of constituents on aldose reducatase from the flower budsofPrunusmumerdquoChemical and Pharmaceutical Bulletin vol 61no 4 pp 445ndash451 2013
[64] S Nakamura K Fujimoto T Matsumoto et al ldquoStructuresof acylated sucroses and an acylated flavonol glycoside andinhibitory effects of constituents on aldose reductase from theflower buds of Prunus mumerdquo Journal of Natural Medicines vol67 no 4 pp 799ndash806 2013
[65] L-B Dong J He X-Y Li et al ldquoChemical constituents fromthe aerial parts of Musella lasiocarpardquo Natural Products andBioprospecting vol 1 no 1 pp 41ndash47 2011
[66] Y Xiong K Z Deng Y Q Guo W Y Gao and T J ZhangldquoNew chemical constituents from the rhizomes of Sparganiumstoloniferumrdquo Archives of Pharmacal Research vol 32 no 5 pp717ndash720 2009
[67] Y Xiong K-Z Deng Y-Q Guo W-Y Gao and T-J ZhangldquoTwo new sucrose esters from Sparganium stoloniferumrdquo Jour-nal of Asian Natural Products Research vol 10 no 5 pp 425ndash428 2008
[68] B Chen N L Wang J H Huang and X S Yao ldquoIridoidand phenylpropanoid glycosides from Scrophularia ningpoensis
22 Evidence-Based Complementary and Alternative Medicine
Hemslrdquo Asian Journal of Traditional Medicines vol 2 no 3 pp119ndash123 2007
[69] H Chen Y Z Zhou L Qiao et al ldquoTwo new compounds fromCynanchum amplexicaulerdquo Journal of Asian Natural ProductsResearch vol 10 no 3 pp 248ndash251 2008
[70] C-L Chang L-J Zhang R Y Chen et al ldquoAntioxidant andanti-inflammatory phenylpropanoid derivatives from Calamusquiquesetinerviusrdquo Journal of Natural Products vol 73 no 9 pp1482ndash1488 2010
[71] Y Kawai H Kumagai H Kurihara K Yamazaki R Sawanoand N Inoue ldquo120573-Glucosidase inhibitory activities of phenyl-propanoid glycosides vanicoside A and B from Polygonumsachalinense rhizomerdquo Fitoterapia vol 77 no 6 pp 456ndash4592006
[72] P V Kiem N X Nhiem N X Cuong et al ldquoNew phenyl-propanoid esters of sucrose from Polygonum hydropiper andtheir antioxidant activityrdquo Archives of Pharmacal Research vol31 no 11 pp 1477ndash1482 2008
[73] K J Wang Y J Zhang and C R Yang ldquoAntioxidant phenolicconstituents from Fagopyrum dibotrysrdquo Journal of Ethnophar-macology vol 99 no 2 pp 259ndash264 2005
[74] N Cho J Huh H Yang et al ldquoChemical constituentsof Polygala tenuifolia roots and their inhibitory activity onlipopolysaccharide-induced nitric oxide production in BV2microgliardquo Journal of Enzyme Inhibition and Medicinal Chem-istry vol 27 no 1 pp 1ndash4 2012
[75] Q Ren C S Wu and J L Zhang ldquoUse of on-line stop-flowheart-cutting two-dimensional high performance liquid chro-matography for simultaneous determination of 12 major con-stituents in tartary buckwheat (Fagopyrum tataricum Gaertn)rdquoJournal of Chromatography A vol 1304 pp 257ndash262 2013
[76] Q Ren C S Wu Y Ren and J L Zhang ldquoCharacterizationand identification of the chemical constituents from tartarybuckwheat (Fagopyrum tataricumGaertn) by high performanceliquid chromatographyphotodiode array detectorlinear iontrap FTICR hybrid mass spectrometryrdquo Food Chemistry vol136 no 3-4 pp 1377ndash1389 2013
[77] W Li Y N Sun X T Yan et al ldquoNF-120581B inhibitory activityof sucrose fatty acid esters and related constituents fromAstragalus membranaceusrdquo Journal of Agricultural and FoodChemistry vol 61 no 29 pp 7081ndash7088 2013
[78] J T Cheng J He Y Li et al ldquoThree new sucrose fatty acid estersfrom Equisetum hiemale LrdquoHelvetica Chimica Acta vol 95 no7 pp 1158ndash1163 2012
[79] Y Jiang and P-F Tu ldquoTenuifoliose Q a new oligosaccharideester from the root of Polygala tenuifoliaWilldrdquo Journal of AsianNatural Products Research vol 5 no 4 pp 279ndash283 2003
[80] M Yoshikawa H Matsuda T Morikawa H H Xie S Naka-mura and O Muraoka ldquoPhenylethanoid oligoglycosides andacylated oligosugars with vasorelaxant activity from Cistanchetubulosardquo Bioorganic ampMedicinal Chemistry vol 14 no 22 pp7468ndash7475 2006
[81] P-F Tu H-M Shi Z-H Song Y Jiang and Y-Y ZhaoldquoChemical constituents of Cistanche sinensisrdquo Journal of AsianNatural Products Research vol 9 no 1 pp 79ndash84 2007
[82] C-L Si Y-Y Lu P-P Qin R-C Sun and Y-H Ni ldquoPhenolicextractives with chemotaxonomic significance from the bark ofPaulownia tomentosa var tomentosardquo BioResources vol 6 no4 pp 5086ndash5098 2011
[83] J Wu S Zhang Q Xiao et al ldquoPhenylethanoid and aliphaticalcohol glycosides from Acanthus ilicifoliusrdquo Phytochemistryvol 63 no 4 pp 491ndash495 2003
[84] Y Jiang and P-F Tu ldquoAnalysis of chemical constituents inCistanche speciesrdquo Journal of Chromatography A vol 1216 no11 pp 1970ndash1979 2009
[85] H Otsuka H Kuwabara and H Hoshiyama ldquoIdentification ofsucrose diesters of aryldihydronaphthalene-type lignans fromTrigonotis peduncularisand the nature of their fluorescencerdquoJournal of Natural Products vol 71 no 7 pp 1178ndash1181 2008
[86] M-R Suo J-S Yang and Q-H Liu ldquoLignan oligosaccharideesters from Eritrichium rupestrerdquo Journal of Natural Productsvol 69 no 4 pp 682ndash684 2006
[87] P-F Tu Z-H Song H-M Shi Y Jiang and Y-Y ZhaoldquoArylethyl (=phenylethanoid) glycosides and oligosaccharidefrom the stem of Cistanche tubulosardquo Helvetica Chimica Actavol 89 no 5 pp 927ndash935 2006
[88] M-H Shyr T-H Tsai and L-C Lin ldquoRossicasins A Band rosicaside F three new phenylpropanoid glycosides fromBoschniakia rossicardquoChemical and Pharmaceutical Bulletin vol54 no 2 pp 252ndash254 2006
[89] R FangNCVeitchGCKiteM J RHowes EA Porter andM S J Simmonds ldquoGlycosylated constituents of Iris fulvaandIris brevicaulisrdquoChemical amp Pharmaceutical Bulletin vol 59 no1 pp 124ndash128 2011
[90] J Fu L Zuo J Yang R Chen and D Zhang ldquoOligosaccharidepolyester and triterpenoid saponins from the roots of Polygalajaponicardquo Phytochemistry vol 69 no 7 pp 1617ndash1624 2008
[91] M-C Cheng C-Y Li H-C Ko F-N Ko Y-L Lin andT-S Wu ldquoAntidepressant principles of the roots of polygalatenuifoliardquo Journal of Natural Products vol 69 no 9 pp 1305ndash1309 2006
[92] H T Chang and P F Tu ldquoNew oligosaccharide esters andxanthone C-glucosides from Polygala telephioidesrdquo HelveticaChimica Acta vol 90 no 5 pp 944ndash950 2007
[93] J Li L Feng J Dai R Wang and T Nohara ldquoChemical con-stituents from Polygala telephioidesrdquo China Journal of ChineseMateria Medica vol 34 no 4 pp 402ndash405 2009
[94] W-P Yin T-Z Zhao and H-Y Zhang ldquoA novel oligosaccha-ride ester from Syringa pubescensrdquo Journal of Asian NaturalProducts Research vol 10 no 1 pp 95ndash100 2008
[95] M Valko D Leibfritz J Moncol M T D Cronin M Mazurand J Telser ldquoFree radicals and antioxidants in normal physio-logical functions and human diseaserdquoThe International Journalof Biochemistry amp Cell Biology vol 39 no 1 pp 44ndash84 2007
[96] D Krishnaiah R Sarbatly and R Nithyanandam ldquoA review ofthe antioxidant potential of medicinal plant speciesrdquo Food andBioproducts Processing vol 89 no 3 pp 217ndash233 2011
[97] P Liu Y Hu D-H Guo et al ldquoAntioxidant activity ofoligosaccharide ester extracted from Polygala tenuifolia roots insenescence-accelerated micerdquo Pharmaceutical Biology vol 48no 7 pp 828ndash833 2010
[98] Y Hu H-B Liao G Dai-Hong P Liu Y-Y Wang and KRahman ldquoAntidepressant-like effects of 361015840-disinapoyl sucroseon hippocampal neuronal plasticity and neurotrophic signalpathway in chronically mild stressed ratsrdquo NeurochemistryInternational vol 56 no 3 pp 461ndash465 2010
[99] Y Hu H B O Liao P Liu D-H Guo and K RahmanldquoA bioactive compound from Polygala tenuifolia regulatesefficiency of chronic stress on hypothalamic-pituitary-adrenalaxisrdquo Pharmazie vol 64 no 9 pp 605ndash608 2009
[100] A Jungbauer and SMedjakovic ldquoAnti-inflammatory propertiesof culinary herbs and spices that ameliorate the effects ofmetabolic syndromerdquoMaturitas vol 71 no 3 pp 227ndash239 2012
Evidence-Based Complementary and Alternative Medicine 23
[101] Q Xu Y Wang S Guo Z Shen and L Yang ldquoAnti-inflammatory and analgesic activity of aqueous extract of Flospopulirdquo Journal of Ethnopharmacology vol 152 no 3 pp 540ndash545 2014
[102] K S Kim D S Lee G S Bae et al ldquoThe inhibition of JNKMAPK and NF-120581B signaling by tenuifoliside A isolated fromPolygala tenuifolia in lipopolysaccharide-induced macrophagesis associated with its anti-inflammatory effectrdquo European Jour-nal of Pharmacology vol 721 no 1ndash3 pp 267ndash276 2013
[103] J-G Lee J-M Yon C Lin A Y Jung K Y Jung and S-YNamldquoCombined treatment with capsaicin and resveratrol enhancesneuroprotection against glutamate-induced toxicity in mousecerebral cortical neuronsrdquo Food and Chemical Toxicology vol50 no 11 pp 3877ndash3885 2012
[104] M L Jin S Y Park Y H Kim J-I Oh S J Lee andG Park ldquoThe neuroprotective effects of cordycepin inhibitglutamate-induced oxidative andER stress-associated apoptosisin hippocampal HT22 cellsrdquo NeuroToxicology vol 41 pp 102ndash111 2014
[105] P Liu Y Hu J Li et al ldquoProtection of SH-SY5Y neuronal cellsfrom glutamate-induced apoptosis by 36rsquo-disinapoyl sucrosea bioactive compound isolated from radix polygalardquo Journal ofBiomedicine and Biotechnology vol 2012 Article ID 728342 5pages 2012
[106] P-B Li W-L Lin Y-G Wang W Peng X-Y Cai and W-WSu ldquoAntidiabetic activities of oligosaccharides of Ophiopogonisjaponicus in experimental type 2 diabetic ratsrdquo InternationalJournal of Biological Macromolecules vol 51 no 5 pp 749ndash7552012
[107] T Liu Y M Yip L Song et al ldquoInhibiting enzymatic starchdigestion by the phenolic compound diboside A a mechanisticand in silico studyrdquo Food Research International vol 54 no 1pp 595ndash600 2013
[108] F Cote andMGHahn ldquoOligosaccharins structures and signaltransductionrdquo Plant Molecular Biology vol 26 no 5 pp 1379ndash1411 1994
[109] RACreelman and J EMullet ldquoOligosaccharins brassinolidesand jasmonates nontraditional regulators of plant growthdevelopment and gene expressionrdquo Plant Cell vol 9 no 7 pp1211ndash1223 1997
[110] L Jiao D Wan X Zhang B Li H Zhao and S LiuldquoCharacterization and immunostimulating effects on murineperitoneal macrophages of oligosaccharide isolated from Panaxginseng CAMeyerrdquo Journal of Ethnopharmacology vol 144 no3 pp 490ndash496 2012
Submit your manuscripts athttpwwwhindawicom
Stem CellsInternational
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
MEDIATORSINFLAMMATION
of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Behavioural Neurology
EndocrinologyInternational Journal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Disease Markers
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
BioMed Research International
OncologyJournal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Oxidative Medicine and Cellular Longevity
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
PPAR Research
The Scientific World JournalHindawi Publishing Corporation httpwwwhindawicom Volume 2014
Immunology ResearchHindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Journal of
ObesityJournal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Computational and Mathematical Methods in Medicine
OphthalmologyJournal of
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Diabetes ResearchJournal of
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Research and TreatmentAIDS
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Gastroenterology Research and Practice
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Parkinsonrsquos Disease
Evidence-Based Complementary and Alternative Medicine
Volume 2014Hindawi Publishing Corporationhttpwwwhindawicom
Evidence-Based Complementary and Alternative Medicine 11
Table2Con
tinued
Num
ber
Nam
eR 1
R 2R 3
R 4R 5
R 6R 7
R 8Source
Parts
Reference
120
Tataris
ideC
IAc
HAc
GG
HAc
Fagopyrum
tataric
umRo
ots
[57]
121
Tataris
ideD
GH
HAc
GI
HH
Fagopyrum
tataric
umRo
ots
[57]
122
Tataris
ideF
GH
HH
II
HG
Fagopyrum
tataric
umRo
ots
[57]
123
310158406-O
-Di-sinapoylsu
crose
KH
HH
KH
HH
Polyg
alatricornis
Polygalahongkongensis
Polyg
alasib
irica
Polyg
alatenu
ifolia
Cynanchu
mam
plexica
ule
Roots
Root
barks
Who
leplants
Aeria
lparts
[37ndash394153ndash
566974]
124
661015840-O
-Di-c
oumaroylsu
crose
GH
HH
HG
HH
Bidens
parviflora
Who
leplants
[61]
125
11015840 3101584061015840-O
-Tri-
coum
aroyl-6
-feruloylsucrose
IH
HH
GG
HG
Fagopyrum
tataric
umRo
ots
[7576]
126
3101584061015840-O
-Di-c
oumaroyl-110158406-O
-di-
feruloylsucrose
IH
HH
GG
HI
Fagopyrum
tataric
umRo
ots
[7576]
127
31015840-O
-Cou
maroyl-11015840610158406-O
-tri-
feruloylsucrose
IH
HH
IG
HI
Fagopyrum
tataric
umRo
ots
[7576]
128
11015840 31015840610158406-O
-Tetra-fe
ruloylsucrose
IH
HH
II
HI
Fagopyrum
tataric
umRo
ots
[7576]
SeeS
chem
e2
12 Evidence-Based Complementary and Alternative Medicine
131130129
CH2OHOH
OH
OO
OH
C
C
HH
HHO
OO
O
HO
HOHO
HO
HOOH
OHOHOH
OHOH
HOO
O
O
O
HO
HO
OH
OHOHOH
OHOH
HOO
O
O
O
HO
Figure 3
12
3
4
5
6
1998400
2998400
3998400
4998400
5998400
6998400
HO
O
O
R1O
R2O
R8O
R7OOR3
OR4 OR5OR6
Scheme 2
antidepressant cytotoxic antineoplastic anti-inflammatoryantidiabetic plant growth-regulatory neuroprotective andcerebral protective activities Lignan-derived disaccharideesters phenylpropanoid-derived tetrasaccharide esters andpentasaccharide esterswith biological activities have not beenreported Aside from the isolated constituents oligosaccha-ride mixtures from Rehmannia glutinosa Panax ginseng andScrophularia ningpoensiswere also reported to display diversepharmacological activities such as antidiabetic immunopo-tentiating enhanced memory and antineoplastic activitiesThese active compounds and mixtures could serve as thevaluable candidates to be developed as possible drugs for thetreatment and prevention of diseases
31 Antioxidant Activity The adverse effects of oxidativestress proposed to play significant roles in the pathogenesis ofcardiovascular diseases atherosclerosis hypertension can-cer diabetes mellitus neurodegenerative diseases rheuma-toid arthritis ischemiareperfusion injury and ageing havebecome an inevitable and serious issue [95 96] Scientistshave thus made great efforts to explore antioxidants frommedicinal plants by using different kinds of assay methodswhich include DPPH radical scavenging assay hydroxylradical scavenging assay superoxide anion scavenging assayand ABTS radical scavenging method [96]
Lapathosides C and D hydropiperoside vanicoside Bhidropiperosides A and B lapathoside A and diboside Awere isolated from the Polygonum Persicaria and Fagopyrumgenera belonging to the Polygonaceae family The DPPH testrevealed that free radical-scavenging activity of the isolatedcompounds termed lapathoside C (115) hydropiperoside(42) vanicoside B (111) and lapathoside D (38) increasedin turn and lapathoside D exhibited strongest scavengingability with an IC
50of 0088 120583M [43] Hidropiperosides A
and B (117 118) were reported to show obvious antioxidantresponse to DPPH radicals with the SC
50values of 234
and 267 120583gmL respectively while vanicoside E moderatelyexhibited the same activity with a SC
50value of 490 120583gmL
[72] Lapathoside A (114) and diboside A (116) just showedlower antioxidant activities with the SC
50values of 19948 and
16552 120583M respectively [73]Smiglasides A and B smilaside P 26-di-acetyl-3101584061015840-
di-feruloylsucrose helonioside B smilasides GndashL and het-erosmilaside were isolated from the Heterosmilax and Smi-lax genera Compared with ascorbic acid (IC
5014352 120583M)
used as positive control smiglasides A and B and smi-laside P (48 49 65) (IC
5033958 33066 and 31449 120583M
resp) showed higher antioxidant activities than 26-di-acetyl-3101584061015840-di-feruloylsucrose (73) and helonioside B (40) (IC
50
63166 and 51827120583M resp) [47] Additionally Nhiem et alreported that helonioside B heterosmilaside (104) and 26-di-acetyl-3101584061015840-di-feruloylsucrose exhibited important DPPHradical scavenging activities with the SC
50values of 91 127
and 87 120583gmL respectively [48] Compared with smilasidesG-I (57ndash59) (ED
50685ndash794120583M) smilasides JndashL (60ndash62)
showed higher radical scavenging activities with an ED50
value of 267ndash327120583M [44]Five quiquesetinerviusides AndashE (105ndash109) isolated from
the Calamus genus showed weak DPPH scavenging activ-ities (IC
50604ndash1018120583M) but exhibited better hydroxyl
radical scavenging activities (IC50
36ndash84 120583M) Moreoverquiquesetinerviuside C showed superoxide anion scaveng-ing activity with an IC
50value of about 1843 120583M [70]
Liu et al investigated the antioxidant capacity of 310158406-O-di-sinapoylsucrose (DISS) (123) by using the acceleratedsenescence-prone short-lived mice (SAMP) in vivo Theanalyses indicated that the activities of antioxidant enzymesof SOD and glutathione peroxidase ascended obviously inSAMP mice when amended with DISS 50mgkg MoreoverDISS could downregulate and even restore the level ofmalondialdehyde in SAMP model group [97]
From the above studies it can be concluded that oligosac-charide esters with antioxidant activities have been identifiedin the Polygonaceae Liliaceae Smilacaceae and Arecaceaefamilies The results of the antioxidant assays show that theincreased number of phenolic hydroxyl groups and acetylgroups could produce higher antioxidant activity Fan etal indicated that the increased number of phenylpropanoidgroups was not beneficial to free radical scavenging activity[43] Zhang et al pointed out that oligosaccharide esters withferuloyl groups exhibited better antioxidant activities thanthose with coumaroyl groups [44]
Evidence-Based Complementary and Alternative Medicine 13
Table 3 Fatty acid-derived disaccharide esters
Number Name R1 R2 Source Parts Reference132 61015840-O-Linoleylsucrose H O Astragalus membranaceus Roots [77]133 61015840-O-Palmitoylsucrose H P Astragalus membranaceus Roots [77]134 6-O-Palmitoylsucrose P H Astragalus membranaceus Roots [77]
135 61015840-O-Linolenoylsucrose H N Astragalus membranaceusEquisetum hiemale
RootsAerial parts [77 78]
136 6-O-Linoleylsucrose O H Astragalus membranaceus Roots [77]137 6-O-Myristoylsucrose Q H Astragalus membranaceus Roots [77]
138 6-O-[(7Z10Z13Z)-Hexadeca-71013-trienoyl]sucrose H R Equisetum hiemale Aerial parts [78]
139 6-O-[(7Z10Z)-Hexadeca-710-dienoyl]sucrose H S Equisetum hiemale Aerial parts [78]
See Scheme 3
12
3
4
5
6
1998400
2998400
3998400
4998400
5998400
6998400
HO
O
O
R1O
R2O
R8O
R7OOR3
OR4 OR5OR6
O
O
O
18
18
1616
16
14
N linolenoyl
O linoleyl
P palmitoyl
Q myristoyl
O
O
O
R hexadeca-71013-trienoyl
S hexadeca-710-dienoyl
Scheme 3
32 Antidepressant Activity The oligosaccharides obtainedfrom the Morinda genus not only show specific antidepres-sant and antistress activities but also have no suppression orexcitatory effects on central nervous system as well Whatis more they can be taken orally with little toxicity [21]The inulin-type hexasaccharide (IHS) (9) from Morindaofficinalis obviously exhibited cytoprotective activity whichcontributed to the antidepressant effect not only by providingthe PC12 with protection against Cort-induced lesion withIHS 0625 and 125 120583Mbut also by reducing theCort-induced[Ca2+]
119894overloading with IHS 25 and 10 120583M IHS 5 and
10 120583Mupregulated the nerve growth factormRNAexpressionin Cort-induced PC12 cells [22] Polygalatenosides A (181)and B (182) were isolated from the Polygala genus Theysignificantly inhibited the isotope-labeled RTI-55 binding to
norepinephrine transporter protein with the IC50
values of300 and 604 120583M respectively [91]
DISS and tenuifoliside A were isolated from the PolygalaandCynanchum genera Liu et al investigated the antidepres-sant effect of YZ ethanol extract based on the tail suspensiontest (TST) and forced swimming test (FST) which arethe ease-of-use and widely-accepted models for estimatingantidepressant activities in mice The results indicated thatYZ-50 fraction at a dose of 200mgkgwas able to significantlydecrease the immobility time in TST Furthermore YZ-50possessed ability to inhibit corticosterone-induced injury ofhuman neuroblastoma SH-SY5Y cells What is more DISS(123) and tenuifoliside A (44) two major compounds of YZ-50 fraction showed effective protective response to the lesionin SY5Y cells [53] The antidepressant-like effect of DISS at
14 Evidence-Based Complementary and Alternative Medicine
H3CO
HO
HOHO
HO
HO
HO
HOHO
O O
OO O
OO
O
O
O
OO
O
O
OH
OH
OH
OH
OCH3
OCH3
CH2OH
CH2OH
CH2OAc
CH2OAc
H3CO
HOHO
HO
O
O
O
OO
O
O
OH
OH
OH
OCH3
CH2OH
CH2OH
H3CO
H3CO H3CO
HOHO
HO
O
O
O
OO
O
O
OH
OH
OH
OCH3
CH2OH
CH2OAc
CH3O
H
HOHO
HO
HO
HOO O
OO O
OO
OH
OCH3
CH2OHCH2OH
H3CO H3CO
H
CH2CH2 HO
HO
HO
HO
HOO O
OO O
OO
OH
OCH3
CH2OHCH2OAc
H3CO
H
CH2
140 141 142
143 144 145
Figure 4
Table 4 Phenylpropanoid-derived trisaccharide esters
Number Name R1 R2 R3 R4 R5 R6 R7 Source Parts Reference146 Tricornose C K H H H H L H Polygala tricornis Roots [37]147 Tricornose D K H H H H K H Polygala tricornis Roots [37]148 Tricornose E K H H H K L H Polygala tricornis Roots [37]149 Tricornose F K H H H I L H Polygala tricornis Roots [37]See Scheme 4
O
OOO
O
R2O
R4O
R3O
R6O
OH
OH
OH
OH
OR1
OR5CH2OR7
Scheme 4
the doses of 5 10 and 20mgkg was also tested in chronicallymild stressed rats DISS was able to exhibit antidepressantactivity by upregulating the expression of noradrenergic-regulated plasticity genes including cell adhesion moleculeL1 brain-derived neurotrophic factor laminin and cAMP
response element binding protein factor in hippocampus[98] DISS improved the reward reaction by increasingsucrose intake and obviously decreased the levels of serumcortisol adrenocorticotrophic hormone and corticotropin-releasing factor Further DISS played an enhanced role inthe expression of mineralocorticoid receptor together withglucocorticoid receptor mRNA [99]
33 Cytotoxic and Antineoplastic Activities Smilasides AndashFand P smiglasides A and B smilaside P and helonioside Awere isolated from the Smilax Trillium and Paris generaKuo et al obtained smilasides AndashF (51ndash56) and evaluatedtheir cytotoxicity against human tumor cell lines comprisinghuman oral epithelium carcinoma (KB) human cervicalcarcinoma (Hela) human colon tumor (DLD-1) humanbreast adenocarcinoma (MCF-7) human lung carcinoma (A-549) and humanmedulloblastoma (Med) cells byMTTassayExperimental data indicated that all but smilaside C showedcytotoxicity against three to six human tumor cell lines(ED50
= 51ndash130 120583gmL) and smilasides DndashF (ED50
= 27ndash50 120583gmL) displayed strong cytotoxic activities against DLD-1 cells [46]Wang et al reported the antitumor constituents of
Evidence-Based Complementary and Alternative Medicine 15
OH
OH
OH
OH
OH
OHOH
OHOH
OHOH
OH
OHOHOH
OH
OH
OH
OHOH
OH
OH
OHOH
H
H H
HO
O
O
O
O
O
O
O
OO
OO
O
OO
O
HO
HO
HO
OO
O
O
OO
OO
O
OO
O
OO
O
OO
O
O
O
OO
O
O
OO
O
OO
OOOO
HO
HO
HO
HO
HO
HO
HO
HO
HO
HO
HOHO
HO
HO
HO
HO
HO
150 151 152
153 180
AcO
AcO
AcOAcO
OAc
OAc
CH2OH
OHOH
OH OHOH
OHOH
OH
OHOH
CH3O
Figure 5
Table 5 Phenylpropanoid-derived tetrasaccharide esters
Number Name R1 R2 R3 Source Parts Reference154 Tricornose G K H K Polygala tricornis Roots [37]155 Tricornose H K K K Polygala tricornis Roots [37]156 Tricornose I K K L Polygala tricornis Roots [37]157 Tricornose J K I L Polygala tricornis Roots [37]158 Tricornose K K I K Polygala tricornis Roots [37]159 Tricornose L K G K Polygala tricornis Roots [37]See Scheme 5
Smilax riparia including smiglasides A (48) and B (49) 26-di-acetyl-3101584061015840-di-feruloylsucrose (73) helonioside B (40)and smilaside P (65) Only smiglasidesA andB and smilasideP exhibited cytotoxicity against human tumor cell lines withdifferent inhibitory concentrations comparing with cisplatinand paclitaxel as positive controls [47] Helonioside A (39)exhibited higher cytotoxicity with the increase of concentra-tion (01ndash100120583gmL) [45] Tatarisides AndashG (45 119ndash121 46122 47) and diboside A (116) from the Fagopyrum genusexerted cytotoxic activities against different human cell linesand the cytotoxicity of tatariside C was the most remarkablewith the IC
50values ranging from 644 to 749 120583gmL [57]
11015840236-O-Tetra-acetyl-31015840-O-cis-feruloylsucrose (95) fromthe Sparganium plants exhibited extremely weak cyto-toxicity against the growth of mice Lung Adenocarcinoma
795 cell lines with an IC50
value of 116 120583gmL [66] SnS-2oligosaccharides mixture including raffinose (3) stachyose(19) and verbascose (21) from the roots of Scrophularianingpoensis had antitumor activity against the growth ofLewis pulmonary carcinoma cells transplanted into mice[18]
Disaccharide esters and oligosaccharides mixture fromthe Liliaceae Polygonaceae Sparganiaceae and Scrpophular-iaceae families showed effective cytotoxic and antineoplasticactivities The study results indicated that feruloyl and acetylgroups play an important role in mediating cytotoxicitywhich seems to be related to the substitution position offeruloyl groups The feruloyl groups at C-6 or C-11015840 are vitalfor cytotoxicity In addition the increased number of acetylgroups could induce higher tumoricidal activity
16 Evidence-Based Complementary and Alternative Medicine
Table 6 Phenylpropanoid-derived pentasaccharide esters
Number Name R1 R2 R3 R4 R5 R6 Source Parts Reference160 Tenuifoliose A G D I Ac Ac Ac Polygala tenuifolia Roots [38 42]161 Tenuifoliose B G D I H Ac Ac Polygala tenuifolia Roots [42]162 Tenuifoliose C G D I H H H Polygala tenuifolia Roots [42]163 Tenuifoliose F G D U Ac Ac Ac Polygala tenuifolia Roots [42]164 Tenuifoliose G G D U Ac H Ac Polygala tenuifolia Roots [42]165 Tenuifoliose H G D G Ac Ac Ac Polygala tenuifolia Roots [38 42 79]166 Tenuifoliose I G D G Ac H Ac Polygala tenuifolia Roots [42 79]167 Tenuifoliose J G D G H Ac Ac Polygala tenuifolia Roots [42]168 Tenuifoliose K G D G H H Ac Polygala tenuifolia Roots [42]169 Tenuifoliose L G D T Ac Ac Ac Polygala tenuifolia Roots [42 79]170 Tenuifoliose M G D T Ac H Ac Polygala tenuifolia Roots [42]171 Tenuifoliose N I D I Ac Ac Ac Polygala tenuifolia Roots [42]172 Tenuifoliose O I D I H Ac Ac Polygala tenuifolia Roots [42]173 Tenuifoliose P I D I H H Ac Polygala tenuifolia Roots [42]174 Tenuifoliose Q G D T H Ac Ac Polygala tenuifolia Roots [79]175 Tenuifoliose S G D G H H H Polygala tenuifolia Roots [42]176 Tenuifoliose T G D I H H H Polygala tenuifolia Roots [42]177 Tenuifoliose V H D I Ac Ac Ac Polygala tenuifolia Roots [42]178 Tenuifoliose W I D U Ac H Ac Polygala tenuifolia Roots [42]179 Tenuifoliose X I D I H H H Polygala tenuifolia Roots [42]See Scheme 6
O
OO
O
O
O
O
OR1
OH
OH
OH
OHOH
OH
HOHO
HO
HO
OR2
R3O
CH2OH
Scheme 5
34 Anti-Inflammatory Activity Inflammation an importantbasic pathological process is a defense response of biopsywith vascular system to damage stimuli such as pathogensimpaired cells and tissues and physical and chemical factorsHowever if the process of inflammatory response cannot endnormally when cell debris and pathogens were cleared thebiological defence response will become causative factor andbring about many diseases such as diabetes cardiovasculardiseases metabolic syndrome and cancer [100 101]
Tenuifoliside A (44) from the Polygala genus exhibitedstrong anti-inflammatory effect not only by suppressing the
production of NO but also by reducing the production ofiNOS prostaglandin E2 cyclooxygenase-2 and proinflam-matory cytokines through the inhibition of the mitogen-activated protein kinases pathway and NF-120581B pathway [102]The anti-inflammatory activities of quiquesetinerviusides D(108) and E (109) from the Calamus genus were evaluated inRAW 2647 cells Both of them showed significant inhibitoryeffects against the production of LPS-stimulated NOwith theIC50values of 90ndash295120583M [70]Six disaccharide fatty acid esters (132ndash137) were iso-
lated from the Astragalus and Equisetum genera The anti-inflammatory effects of these isolated compounds have alsobeen documented The activation of NF-120581B could upregulatethe expression of proinflammatory cytokines inducible nitricoxide synthase (iNOS) and tumornecrosis factor alpha (TNF-120572) The NF-120581B inhibitory activities of compounds 132ndash137were tested in HepG2 cells stimulated with TNF-120572 All ofthese compounds could significantly restrainTNF-120572-inducedNF-120581B transcriptional activities with the IC
50values of 44ndash
247 120583M Li et al pointed out that olefinic bonds and thelength of the fatty acid moieties contributed to the NF-120581B inhibitory activity Furthermore the inhibition increasedsignificantly with the increase of the number of olefinic bondson the aliphatic moiety [77] These results may provide ascientific basis for the development of new anti-inflammatoryagents
35 Neuroprotective and Cerebral Protective Activities Aswe all know glutamate works as a major excitatory aminoacid neurotransmitter in the mammalian central nervous
Evidence-Based Complementary and Alternative Medicine 17
R6O
R2O
OR3
OR5
OR4
CH2OR1
OCH3
Rham
OO
O
OO O
O
O
O
OO
RhamO
O
OH
OH
OHOH
OH
OHOH
OHHO
HO
HO
T O-rhamnosyl-coumaroyl U O-rhamnosyl-feruloyl
Scheme 6
system and plays a crucial role in several physiological pro-cesses [103] However the accumulation of glutamate inducesdiverse acute and chronic neurodegenerative diseases suchas epilepsy ischemic stroke and Parkinsonrsquos disease aswell as Alzheimerrsquos disease [104] DISS (123) isolated fromthe Polygala genus exhibited neuroprotective effect againstglutamate-induced SH-SY5Y neuronal cell damage The invitro test demonstrated that DISS (06 6 and 60 120583molL)played a critical role in increasing cell viability controllinglactate dehydrogenase and attenuated apoptosis ranging from195 to 258 [105]
Tenuifoliside B (102) from the Polygala genus was ableto significantly shorten the coma time of KCN-inducedanoxia mice at the doses of 3 and 10mgkg and it playedan important role in ameliorating the scopolamine-inducedimpairment of performance in passive avoidance task inrats and enhancing the tremors induced by oxotremorine inmiceThese results together demonstrated that tenuifoliside Bpossessed cognitive improving and cerebral protective effects[56]
36 Antidiabetic Activity Diabetes mellitus a chronic debil-itating metabolic disease is characterized by high bloodglucose content and comprises three types termed type Itype II and gestational diabetes [106] Stachyose (19) extract(a part) from Rehmannia glutinosa obviously exhibited theactivity of downregulating fasting plasma glucose level andpartially keeping from hyperglycemia induced by adrenalineand glucose without obvious dose-dependent effect Otherthan that in vivo tests in rats induced by alloxan revealed
that stachyose extract at the dose of 200mgkg significantlydecreased blood-sugar level [15]
Diboside A lapathosides C and D vanicosides A andB and hydropiperoside were isolated from the FagopyrumPolygonum and Persicaria genera belonging to the Polygo-naceae family Diboside A (116) could potentially inhibit 120572-amylase activity with an IC
50of 269 120583M and thus retard the
starch digestion rate which is helpful for diabetic individualsin controlling blood sugar level [107] Lapathoside D (38)exerted stronger activity of 120572-glucosidase inhibition with anIC50
value of 0113mM than acarbose which was chosen asa positive drug for the treatment of type II diabetes [43]Vanicoside B (111) was reported to have higher 120573-glucosidaseinhibitory activity with an IC
50of 505 120583M than vanicoside A
(110) with an IC50of 599 120583M because of the acetyl moiety of
the latter possibly decreasing inhibitory activity of vanicosideA [71]
Fujimoto et al investigated the inhibitory effects ofmumeoses FndashO (83ndash92) from the Prunus genus on aldosereductase and discovered that caffeoyl groups are crucialfor the inhibitory effect on aldose reductase And thusmumeoses F G H J K L M and N (IC
50= 22ndash77120583M) with
a coumaroyl group and acetyl groups inhibited moderatelyaldose reductase from reducing glucose to sorbitol whichis associated with the chronic complications of diabetes [6364]
37 Elicitors and Regulators Oligosaccharides are quitepropitious for encoding biological information because ofdiverse monosaccharide units and complex molecular struc-tures and they are therefore first described as biological
18 Evidence-Based Complementary and Alternative Medicine
181 H
H
H
H
H
H
H
H
H H
H
H
H
H
H
H
H H
HH
Benzyl
Benzyl
Benzyl
182
183
184 Ac
Ac
Ac
Ac
Ac
Ac
Ac
Ac
Ac
Ac
185
186
187
188
189
R1 R2 R3
R1 R2 R3 R4
OCH3
R3OH2C OR2
OR1
OR1
O
O
O
O O
OOO
O
OO
O
OH
OH
OH OH
OH
O O
O
O
OH
HO
OH
OH OHOH
OH
OH
OHHO
HO
OH
OH
HO
CH2OH
CH2OH
CH2OH
CH2OH
C
R2O
R3O
CH2OR4
CH2CH2 CH2CH2CH2CH2CH3
CH3
CH3
191190 192
193
O
C C
O
OO
OO
OO
OO
O O
O
O
O
O
O
O
OH
OH
OHHO
HO
HOOH
OH
OH
OH
HO
OH
OH
OH
OH
HO
HO
C C
R998400O
R998400
Figure 6
signals in plants [108] Oligosaccharides from the cell wallfragments of plants and fungi are powerful signal moleculessuch as the elicitors of plant defence response and theregulators of plant growth and they are capable of exertingbiological activities at exceedingly low concentrations [109]Heptasaccharide (HS) (15) and octasaccharide (OS) (16) iso-lated from the Paris genus possessed plant growth-regulatory
activities [29 30]The two oligosaccharides significantly pro-moted the proliferation of Paris polyphylla var yunnanensisroots at the doses of 25ndash20mgL The octasaccharide hadthe most obvious effect on the growth of Panax japonicusvar major hairy roots at a dose of 30mgL while the otherhad the most positive effect on saponin accumulation ofPanax japonicus var major hairy roots at a dose of 10mgL
Evidence-Based Complementary and Alternative Medicine 19
[29] Similarly Zhou et al evaluated the stimulating effectsof HS and OS on the root growth and saponin productionof Panax ginseng hairy roots which were induced from theplant roots infected withAgrobacterium rhizogenes strain A4The results showed that there was a maximum effect on thehairy roots growth and saponin accumulation on day 10Compared with control group the root biomass dry weightwas increased by more than 17-fold while the total saponincontent of roots increased by more than 1-fold when thesetwo oligosaccharides were added to the hairy root at a dose of30mgL [30] The above data illustrate that HS and OS couldserve as the plant growth-regulators not only in their originalspecies but also in others
38 Immunopotentiating Activity Macrophages are impor-tant targets of investigations on cytophagy cellular immunityand molecular immunology Therefore they are deemedto play a vital role in host defense comprising phagocy-tosis proteolytic processing pathogenic agent apoptosiscytokines production and foreign antigens presentation[110] The water-extracted oligosaccharides from Panax gin-seng (WGOS) exhibited better immunopotentiating activ-ity by increasing phagocytic function of macrophages andpromoting NO TNF-120572 and reactive oxygen species pro-duction [110] In addition Wan et al have obtained malto-oligosaccharides (17 119899 = 3sim8) and three oligosaccharides (213 14) from the Panax ginseng roots The in vitro bioassaypointed out thatWGOS could serve as efficacious stimulatorsof B and T lymphocytes [28] These studies provided enlight-enment that the mixture of oligosaccharides from Chineseherbalmedicine exhibits significant effect on immune system
39 Others Acetylcholinesterase (AChE) inhibitors showgood therapeutic effects onmyasthenia gravis glaucoma andAlzheimerrsquos disease through reversible enzyme inhibitionso as to increase the accumulation of acetylcholine in thesynapse and then promote and prolong the function ofacetylcholine Vanicoside B (111) showed AChE inhibitoryactivity with an IC
50of 0062mM while hydropiperoside
(42) and lapathosides C (115) and D (38) just exhibited weakenzyme inhibitory activity [43]
Wang et al has explored low molecular mass carbohy-drate polymer from Panax ginseng roots and obtained 30ethanol elution (PGO)which included peptides and oligosac-charides (17 119899 = 0sim5) identified as maltose maltotriosemaltotetraose maltopentaose maltohexaose and maltohep-taose Pharmacological experiments revealed that PGO couldsignificantly enhance the memory in scopolamine-inducedmemory deficit rats [27]
Cistanoside F (129) and kankanose (150) were isolatedfrom the Cistanche Paulownia and Acanthus genera Phar-macological experiments showed that cistanoside F andkankanose significantly exhibited vasorelaxant effects on thenoradrenaline-induced contraction of thoracic aorta fromrats [80]
4 Conclusion
Traditional Chinese medicine from natural kingdom playsan indelible role in the treatment of human diseases andit has aroused the attention of those who have engagedin medicinal pharmaceutical chemistry Therefore scientistshave made great contributions day after day to investigate thevalid chemicals from traditional Chinese medicines In thepast decades about 193 oligosaccharides and their esters havebeen identified from traditional Chinese medicinal plantsOn the one hand only a few oligosaccharides and theirmixtures were investigated and just exhibited antidepres-sant antineoplastic antidiabetic plant growth-regulatoryimmunopotentiating and enhancedmemory activitiesMoreexploratory work is still needed to excavate biological andpharmacological activities of oligosaccharides On the otherhand oligosaccharide esters exhibited multi-advantageousactivities Bioassays have revealed that antioxidant cytotoxicantineoplastic and anti-inflammatory activities are the mostnotable bioactivities Of course to search for the naturalproducts with these activities is a hotpot in the contemporarydrug research Oligosaccharide esters provide a vast treasuretrove for medical researchers After considering the currentstudies it should be taken as future directions to makemore mechanism of action studies and clinical trials tofurther evaluate its potential as new drugs Moreover thestructure-activity relationships discussed in this review willprovide reference information for further exploring theirrelationships and continually discovering the new bioactiveoligosaccharide esters
Conflict of Interests
The authors declare that there is no conflict of interestsregarding the publication of this paper
References
[1] X D Yang L J Zhang B Liang L Z Xu and S L YangldquoOligosaccharide esters isolated from plants of PolygalaceaerdquoChinese Traditional and Herbal Drugs vol 33 no 10 pp 954ndash958 2002
[2] N Ogwuru and M Adamczeski ldquoBioactive natural productsderived from Polygonum species of plants their structures andmechanisms of actionrdquo Studies in Natural Products Chemistryvol 22 pp 607ndash642 2000
[3] S Kobayashi T Miyase and H Noguchi ldquoPolyphenolic glyco-sides and oligosaccharide multiesters from the roots of Polygaladalmaisianardquo Journal of Natural Products vol 65 no 3 pp 319ndash328 2002
[4] M Takasaki S Kuroki M Kozuka and T Konoshima ldquoNewphenylpropanoid esters of sucrose from Polygonum lapathi-foliumrdquo Journal of Natural Products vol 64 no 10 pp 1305ndash1308 2001
[5] M L Zimmermann and A T Sneden ldquoVanicosides A and Bprotein kinase C inhibitors from Polygonum pensylvanicumrdquoJournal of Natural Products vol 57 no 2 pp 236ndash242 1994
[6] M Takasaki T Konoshima S Kuroki H Tokuda and HNishino ldquoCancer chemopreventive activity of phenylpropanoid
20 Evidence-Based Complementary and Alternative Medicine
esters of sucrose vanicoside B and lapathoside A from Poly-gonum lapathifoliumrdquo Cancer Letters vol 173 no 2 pp 133ndash138 2001
[7] Q Fu T Liang Z Y Li et al ldquoSeparation of carbohydrates usinghydrophilic interaction liquid chromatographyrdquo CarbohydrateResearch vol 379 pp 13ndash17 2013
[8] M F Mrozek D Zhang and D Ben-Amotz ldquoOligosaccharideidentification and mixture quantification using Raman spec-troscopy and chemometric analysisrdquo Carbohydrate Researchvol 339 no 1 pp 141ndash145 2004
[9] G S Armstrong and B Bendiak ldquoHigh-resolution four-dimen-sional carbon-correlated 1H-1H ROESY experiments employ-ing isotags and the filter diagonalization method for effectiveassignment of glycosidic linkages in oligosaccharidesrdquo Journalof Magnetic Resonance vol 181 no 1 pp 79ndash88 2006
[10] G S Armstrong V A Mandelshtam A J Shaka and BBendiak ldquoRapid high-resolution four-dimensional NMR spec-troscopy using the filter diagonalization method and its advan-tages for detailed structural elucidation of oligosaccharidesrdquoJournal of Magnetic Resonance vol 173 no 1 pp 160ndash168 2005
[11] H-M Tseng S Gattolin J Pritchard H J Newbury and DA Barrett ldquoAnalysis of mono- di- and oligosaccharides by CEusing a two-stage derivatization method and LIF detectionrdquoElectrophoresis vol 30 no 8 pp 1399ndash1405 2009
[12] N Li X Li B L Hou and D L Meng ldquoNew disaccharosidefrom Camptosorus sibiricus Ruprrdquo Natural Product Researchvol 22 no 15 pp 1379ndash1383 2008
[13] Z Zhang D Wang Y Zhao H Gao Y-H Hu and J-FHu ldquoFructose-derived carbohydrates from Alisma orientalisrdquoNatural Product Research vol 23 no 11 pp 1013ndash1020 2009
[14] X Yang Y Zhao N He and K D Croft ldquoIsolation char-acterization and immunological effects of 120572-galacto-oligo-saccharides from a new source the herb Lycopus lucidus TurczrdquoJournal of Agricultural and Food Chemistry vol 58 no 14 pp8253ndash8258 2010
[15] R X Zhang Z P Jia L Y Kong et al ldquoStachyose extractfrom Rehmannia glutinosa Libosch to lower plasma glucose innormal and diabetic rats by oral administrationrdquo Pharmazievol 59 no 7 pp 552ndash556 2004
[16] R Zhang Y Zhao Y Sun X Lu and X Yang ldquoIsolationcharacterization and hepatoprotective effects of the raffinosefamily oligosaccharides from Rehmannia glutinosa liboschrdquoJournal of Agricultural and Food Chemistry vol 61 no 32 pp7786ndash7793 2013
[17] H Li F Song Z Zheng Z Liu and S Liu ldquoCharacterization ofsaccharides and phenolic acids in the Chinese herb Tanshen byESI-FT-ICR-MS and HPLCrdquo Journal of Mass Spectrometry vol43 no 11 pp 1545ndash1552 2008
[18] J E Deng J Zhang XM ChenW Ke and G Y Tian ldquoStudieson the physicochemical properties structure and antitumoractivity of an oligosaccharide homologue SnS-2 from the root ofScrophularia ningpoensis Hemslrdquo Chinese Journal of Chemistryvol 22 no 5 pp 492ndash497 2004
[19] S C Chou LM Chuang and S S Lee ldquoHypoglycemic constit-uents of gynura divaricata subsp formosanardquo Natural ProductCommunications vol 7 no 2 pp 221ndash222 2012
[20] F Feng L-L Wang X-P Lai Y-B Li Z-M Cao and Y-J Zhou ldquoStudy on oligosaccharides from Morinda officinalisrdquoJournal of Chinese Medicinal Materials vol 35 no 8 pp 1259ndash1262 2012
[21] Y F Li Z H Gong M Yang Y M Zhao and Z P Luo ldquoInhibi-tion of the oligosaccharides extracted fromMorinda officinalis
a Chinese traditional herbal medicine on the corticosteroneinduced apoptosis in PC12 cellsrdquo Life Sciences vol 72 no 8 pp933ndash942 2003
[22] Y-F Li Y-Q Liu M Yang et al ldquoThe cytoprotective effect ofinulin-type hexasaccharide extracted from Morinda officinalison PC12 cells against the lesion induced by corticosteronerdquo LifeSciences vol 75 no 13 pp 1531ndash1538 2004
[23] D N Olennikov L M Tankhaeva and A V Rokhin ldquoGlu-cofructans from Saussurea lappa rootsrdquo Chemistry of NaturalCompounds vol 47 no 3 pp 339ndash342 2011
[24] S K Hyun H A Jung B S Min J H Jung and J S ChoildquoIsolation of phenolics nucleosides saccharides and an alkaloidfrom the root of Aralia cordatardquo Natural Product Sciences vol16 no 1 pp 20ndash25 2010
[25] Z J Xu C W Lin and M F Liao ldquoStructure analysis of a newoligosaccharides BROS from Blumea ripariardquo Chinese Journalof Organic Chemistry vol 31 no 11 pp 1811ndash1819 2011
[26] Z J Xu C W Lin and Y Shi ldquoIsolation and structuredetermination of a new oligosaccharide from Blume ripariardquoJournal of Medicinal Plants Research vol 5 no 14 pp 2956ndash2962 2011
[27] Y Wang R Z Jiang G R Li et al ldquoStructural and enhancedmemory activity studies of extracts from Panax ginseng rootrdquoFood Chemistry vol 119 no 3 pp 969ndash973 2010
[28] DWan L Jiao H Yang and S Liu ldquoStructural characterizationand immunological activities of the water-soluble oligosaccha-rides isolated from thePanax ginseng rootsrdquoPlanta vol 235 no6 pp 1289ndash1297 2012
[29] L G Zhou C Z Yang J Q Li S L Wang and J Y WuldquoHeptasaccharide and octasaccharide isolated from Paris pol-yphylla var yunnanensis and their plant growth-regulatoryactivityrdquo Plant Science vol 165 no 3 pp 571ndash575 2003
[30] L G Zhou X D Cao R F Zhang Y L Peng S J Zhao andJ Y Wu ldquoStimulation of saponin production in Panax ginsenghairy roots by two oligosaccharides from Paris polyphylla varyunnanensisrdquo Biotechnology Letters vol 29 no 4 pp 631ndash6342007
[31] M Vanhaecke W van den Ende E Lescrinier and N Dyu-bankova ldquoIsolation and characterization of a pentasaccharidefrom Stellaria mediardquo Journal of Natural Products vol 71 no 11pp 1833ndash1836 2008
[32] J Feng and W Zhao ldquoComplete 1Hand 13C NMR assignmentsof four new oligosaccharides and two new glycosides fromPeriploca forrestiirdquoMagnetic Resonance in Chemistry vol 47 no8 pp 701ndash705 2009
[33] J Q Feng R J Zhang Y Zhou et al ldquoImmunosuppressive preg-nane glycosides from Periploca sepium and Periploca forrestiirdquoPhytochemistry vol 69 no 15 pp 2716ndash2723 2008
[34] X H Long R Xu Y H Zhang X H Tan andQ Y Sun ldquoA newoligosaccharide from Periploca calophyllardquo Zhongguo ZhongyaoZazhi vol 37 no 2 pp 226ndash229 2012
[35] L Wang Z-Q Yin Y Wang X-Q Zhang Y-L Li and W-CYe ldquoPerisesaccharides A-E new oligosaccharides from the rootbarks ofPeriploca sepiumrdquoPlantaMedica vol 76 no 9 pp 909ndash915 2010
[36] T Lei L Zhang H-Y Jiang Y Hu A-H Hong and Y-Z CenldquoA new pregnane glycoside and oligosaccharide from Parabar-ium huaitingiirdquo Journal of Asian Natural Products Research vol13 no 11 pp 1030ndash1035 2011
[37] J Li Y Jiang and P F Tu ldquoTricornoses A-L oligosaccharidemulti-esters from the roots of Polygala tricornisrdquo Journal ofNatural Products vol 68 no 5 pp 739ndash744 2005
Evidence-Based Complementary and Alternative Medicine 21
[38] H H Tu P Liu L Mu et al ldquoStudy on antidepressant com-ponents of sucrose ester from Polygala tenuifoliardquo ZhongguoZhongyao Zazhi vol 33 no 11 pp 1278ndash1280 2008
[39] G M She Y Y Ba Y Liu H Lv W Wang and R B ShildquoAbsorbable phenylpropenoyl sucroses from Polygala tenuifo-liardquoMolecules vol 16 no 7 pp 5507ndash5513 2011
[40] J Yong and P F Tu ldquoStudies on the chemical constituents inroot bark of Polygala tenuifolia (II)rdquo China Journal of ChineseMateria Medica vol 29 no 8 pp 751ndash753 2004
[41] M Ono C Takamura F Sugita et al ldquoTwo new steroidglycosides and a new sesquiterpenoid glycoside from theunderground parts of Trillium kamtschaticumrdquo Chemical andPharmaceutical Bulletin vol 55 no 4 pp 551ndash556 2007
[42] Y Ling Z Li M Chen Z Sun M Fan and C HuangldquoAnalysis and detection of the chemical constituents of RadixPolygalae and their metabolites in rats after oral administrationby ultra high-performance liquid chromatography coupledwith electrospray ionization quadrupole time-of-flight tandemmass spectrometryrdquo Journal of Pharmaceutical and BiomedicalAnalysis vol 85 pp 1ndash13 2013
[43] P Fan L Terrier A-E Hay A Marston and K HostettmannldquoAntioxidant and enzyme inhibition activities and chemicalprofiles ofPolygonum sachalinensis FSchmidt exMaxim (Polyg-onaceae)rdquo Fitoterapia vol 81 no 2 pp 124ndash131 2010
[44] L J Zhang C C Liao H C Huang Y C Shen L M Yangand Y H Kuo ldquoAntioxidant phenylpropanoid glycosides fromSmilax bracteatardquo Phytochemistry vol 69 no 6 pp 1398ndash14042008
[45] L L Yan W Y Gao Y J Zhang and Y Wang ldquoA new phenyl-propanoid glycosides from Paris polyphylla var yunnanensisrdquoFitoterapia vol 79 no 4 pp 306ndash307 2008
[46] Y H Kuo Y W Hsu C C Liaw J K Lee H C Huang andL M Y Kuo ldquoCytotoxic phenylpropanoid glycosides from thestems of Smilax chinardquo Journal of Natural Products vol 68 no10 pp 1475ndash1478 2005
[47] W-X Wang T-X Li H Ma J-F Zhang and A-Q JialdquoTumoral cytotoxic and antioxidative phenylpropanoid glyco-sides in Smilax riparia A DCrdquo Journal of Ethnopharmacologyvol 149 no 2 pp 527ndash532 2013
[48] N X Nhiem P vanKiem C vanMinh et al ldquoPhenylpropanoidglycosides fromHeterosmilax erythrantha and their antioxidantactivityrdquo Archives of Pharmacal Research vol 32 no 10 pp1373ndash1377 2009
[49] Y Wang W Y Gao T J Zhang and Y Q Guo ldquoA novelphenylpropanoid glycosides and a new derivation of phenolicglycoside from Paris Polyphylla var yunnanensisrdquo ChineseChemical Letters vol 18 no 5 pp 548ndash550 2007
[50] J-Y Zhang Y-Z Wang Y-L Zhao et al ldquoPhytochemicals andbioactivities of Paris speciesrdquo Journal of Asian Natural ProductsResearch vol 13 no 7 pp 670ndash681 2011
[51] N H N Hashim F Abas K Shaari and N H Lajis ldquoLC-DAD-ESIMSMS characterization of antioxidant and anti-cholinesterase constituents present in the active fraction fromPersicaria hydropiperrdquo LWT Food Science and Technology vol46 no 2 pp 468ndash476 2012
[52] PH FanA EHayAMarstonHX Lou andKHostettmannldquoChemical variability of the invasive neophytes Polygonumcuspidatum Sieb and Zucc and Polygonum sachalinensis FSchmidt ex Maximrdquo Biochemical Systematics and Ecology vol37 no 1 pp 24ndash34 2009
[53] P Liu Y Hu D H Guo et al ldquoPotential antidepressantproperties of Radix Polygalae (Yuan Zhi)rdquo Phytomedicine vol17 no 10 pp 794ndash799 2010
[54] J F Wu S B Chen S L Chen and P F Tu ldquoThe chemical con-stituents of Polygala hongkongensisHemslrdquoActa PharmaceuticaSinica vol 42 no 7 pp 757ndash761 2007
[55] Y Song Y Jiang D Bi X Tian L Liang and P Tu ldquoChemicalconstituents from n-butanol extract of aerial part of Polygalasibiricardquo Zhongguo Zhongyao Zazhi vol 37 no 4 pp 471ndash4742012
[56] Y Ikeya S Takeda M Tunakawa et al ldquoCognitive improvingand cerebral protective effects of acylated oligosaccharides inPolygala tenuifoliardquo Biological and Pharmaceutical Bulletin vol27 no 7 pp 1081ndash1085 2004
[57] C J Zheng C L Hu X Q Ma C Peng H Zhang and L PQin ldquoCytotoxic phenylpropanoid glycosides from Fagopyrumtataricum (L) Gaertnrdquo Food Chemistry vol 132 no 1 pp 433ndash438 2012
[58] X Li Y F Zhang L Yang et al ldquoChemical profiling ofconstituents of Smilacis glabrae using ultra-high pressure liquidchromatography coupled with LTQ orbitrap mass spectrome-tryrdquo Natural Product Communications vol 7 no 2 pp 181ndash1842012
[59] T-T Sun D-W Zhang Y Han F-Y Dong andWWang ldquoSmi-lasides M and N two new phenylpropanoid glycosides fromSmilax ripariardquo Journal of Asian Natural Products Research vol14 no 2 pp 165ndash170 2012
[60] J Li X Bi G Zheng Y Hitoshi T Ikeda and T NoharaldquoSteroidal glycosides and aromatic compounds from Smilaxripariardquo Chemical amp Pharmaceutical Bulletin vol 54 no 10 pp1451ndash1454 2006
[61] N Wang X Yao R Ishii and S Kitanaka ldquoBioactive sucroseesters from Bidens parviflorardquo Phytochemistry vol 62 no 5 pp741ndash746 2003
[62] S Nakamura K Fujimoto T Matsumoto et al ldquoAcylatedsucroses and acylated quinic acids analogs from the flower budsof Prunus mume and their inhibitory effect on melanogenesisrdquoPhytochemistry vol 92 pp 128ndash136 2013
[63] K Fujimoto SNakamura TMatsumoto et al ldquoMedicinal flow-ers XXXVIII Structures of acylated sucroses and inhibitoryeffects of constituents on aldose reducatase from the flower budsofPrunusmumerdquoChemical and Pharmaceutical Bulletin vol 61no 4 pp 445ndash451 2013
[64] S Nakamura K Fujimoto T Matsumoto et al ldquoStructuresof acylated sucroses and an acylated flavonol glycoside andinhibitory effects of constituents on aldose reductase from theflower buds of Prunus mumerdquo Journal of Natural Medicines vol67 no 4 pp 799ndash806 2013
[65] L-B Dong J He X-Y Li et al ldquoChemical constituents fromthe aerial parts of Musella lasiocarpardquo Natural Products andBioprospecting vol 1 no 1 pp 41ndash47 2011
[66] Y Xiong K Z Deng Y Q Guo W Y Gao and T J ZhangldquoNew chemical constituents from the rhizomes of Sparganiumstoloniferumrdquo Archives of Pharmacal Research vol 32 no 5 pp717ndash720 2009
[67] Y Xiong K-Z Deng Y-Q Guo W-Y Gao and T-J ZhangldquoTwo new sucrose esters from Sparganium stoloniferumrdquo Jour-nal of Asian Natural Products Research vol 10 no 5 pp 425ndash428 2008
[68] B Chen N L Wang J H Huang and X S Yao ldquoIridoidand phenylpropanoid glycosides from Scrophularia ningpoensis
22 Evidence-Based Complementary and Alternative Medicine
Hemslrdquo Asian Journal of Traditional Medicines vol 2 no 3 pp119ndash123 2007
[69] H Chen Y Z Zhou L Qiao et al ldquoTwo new compounds fromCynanchum amplexicaulerdquo Journal of Asian Natural ProductsResearch vol 10 no 3 pp 248ndash251 2008
[70] C-L Chang L-J Zhang R Y Chen et al ldquoAntioxidant andanti-inflammatory phenylpropanoid derivatives from Calamusquiquesetinerviusrdquo Journal of Natural Products vol 73 no 9 pp1482ndash1488 2010
[71] Y Kawai H Kumagai H Kurihara K Yamazaki R Sawanoand N Inoue ldquo120573-Glucosidase inhibitory activities of phenyl-propanoid glycosides vanicoside A and B from Polygonumsachalinense rhizomerdquo Fitoterapia vol 77 no 6 pp 456ndash4592006
[72] P V Kiem N X Nhiem N X Cuong et al ldquoNew phenyl-propanoid esters of sucrose from Polygonum hydropiper andtheir antioxidant activityrdquo Archives of Pharmacal Research vol31 no 11 pp 1477ndash1482 2008
[73] K J Wang Y J Zhang and C R Yang ldquoAntioxidant phenolicconstituents from Fagopyrum dibotrysrdquo Journal of Ethnophar-macology vol 99 no 2 pp 259ndash264 2005
[74] N Cho J Huh H Yang et al ldquoChemical constituentsof Polygala tenuifolia roots and their inhibitory activity onlipopolysaccharide-induced nitric oxide production in BV2microgliardquo Journal of Enzyme Inhibition and Medicinal Chem-istry vol 27 no 1 pp 1ndash4 2012
[75] Q Ren C S Wu and J L Zhang ldquoUse of on-line stop-flowheart-cutting two-dimensional high performance liquid chro-matography for simultaneous determination of 12 major con-stituents in tartary buckwheat (Fagopyrum tataricum Gaertn)rdquoJournal of Chromatography A vol 1304 pp 257ndash262 2013
[76] Q Ren C S Wu Y Ren and J L Zhang ldquoCharacterizationand identification of the chemical constituents from tartarybuckwheat (Fagopyrum tataricumGaertn) by high performanceliquid chromatographyphotodiode array detectorlinear iontrap FTICR hybrid mass spectrometryrdquo Food Chemistry vol136 no 3-4 pp 1377ndash1389 2013
[77] W Li Y N Sun X T Yan et al ldquoNF-120581B inhibitory activityof sucrose fatty acid esters and related constituents fromAstragalus membranaceusrdquo Journal of Agricultural and FoodChemistry vol 61 no 29 pp 7081ndash7088 2013
[78] J T Cheng J He Y Li et al ldquoThree new sucrose fatty acid estersfrom Equisetum hiemale LrdquoHelvetica Chimica Acta vol 95 no7 pp 1158ndash1163 2012
[79] Y Jiang and P-F Tu ldquoTenuifoliose Q a new oligosaccharideester from the root of Polygala tenuifoliaWilldrdquo Journal of AsianNatural Products Research vol 5 no 4 pp 279ndash283 2003
[80] M Yoshikawa H Matsuda T Morikawa H H Xie S Naka-mura and O Muraoka ldquoPhenylethanoid oligoglycosides andacylated oligosugars with vasorelaxant activity from Cistanchetubulosardquo Bioorganic ampMedicinal Chemistry vol 14 no 22 pp7468ndash7475 2006
[81] P-F Tu H-M Shi Z-H Song Y Jiang and Y-Y ZhaoldquoChemical constituents of Cistanche sinensisrdquo Journal of AsianNatural Products Research vol 9 no 1 pp 79ndash84 2007
[82] C-L Si Y-Y Lu P-P Qin R-C Sun and Y-H Ni ldquoPhenolicextractives with chemotaxonomic significance from the bark ofPaulownia tomentosa var tomentosardquo BioResources vol 6 no4 pp 5086ndash5098 2011
[83] J Wu S Zhang Q Xiao et al ldquoPhenylethanoid and aliphaticalcohol glycosides from Acanthus ilicifoliusrdquo Phytochemistryvol 63 no 4 pp 491ndash495 2003
[84] Y Jiang and P-F Tu ldquoAnalysis of chemical constituents inCistanche speciesrdquo Journal of Chromatography A vol 1216 no11 pp 1970ndash1979 2009
[85] H Otsuka H Kuwabara and H Hoshiyama ldquoIdentification ofsucrose diesters of aryldihydronaphthalene-type lignans fromTrigonotis peduncularisand the nature of their fluorescencerdquoJournal of Natural Products vol 71 no 7 pp 1178ndash1181 2008
[86] M-R Suo J-S Yang and Q-H Liu ldquoLignan oligosaccharideesters from Eritrichium rupestrerdquo Journal of Natural Productsvol 69 no 4 pp 682ndash684 2006
[87] P-F Tu Z-H Song H-M Shi Y Jiang and Y-Y ZhaoldquoArylethyl (=phenylethanoid) glycosides and oligosaccharidefrom the stem of Cistanche tubulosardquo Helvetica Chimica Actavol 89 no 5 pp 927ndash935 2006
[88] M-H Shyr T-H Tsai and L-C Lin ldquoRossicasins A Band rosicaside F three new phenylpropanoid glycosides fromBoschniakia rossicardquoChemical and Pharmaceutical Bulletin vol54 no 2 pp 252ndash254 2006
[89] R FangNCVeitchGCKiteM J RHowes EA Porter andM S J Simmonds ldquoGlycosylated constituents of Iris fulvaandIris brevicaulisrdquoChemical amp Pharmaceutical Bulletin vol 59 no1 pp 124ndash128 2011
[90] J Fu L Zuo J Yang R Chen and D Zhang ldquoOligosaccharidepolyester and triterpenoid saponins from the roots of Polygalajaponicardquo Phytochemistry vol 69 no 7 pp 1617ndash1624 2008
[91] M-C Cheng C-Y Li H-C Ko F-N Ko Y-L Lin andT-S Wu ldquoAntidepressant principles of the roots of polygalatenuifoliardquo Journal of Natural Products vol 69 no 9 pp 1305ndash1309 2006
[92] H T Chang and P F Tu ldquoNew oligosaccharide esters andxanthone C-glucosides from Polygala telephioidesrdquo HelveticaChimica Acta vol 90 no 5 pp 944ndash950 2007
[93] J Li L Feng J Dai R Wang and T Nohara ldquoChemical con-stituents from Polygala telephioidesrdquo China Journal of ChineseMateria Medica vol 34 no 4 pp 402ndash405 2009
[94] W-P Yin T-Z Zhao and H-Y Zhang ldquoA novel oligosaccha-ride ester from Syringa pubescensrdquo Journal of Asian NaturalProducts Research vol 10 no 1 pp 95ndash100 2008
[95] M Valko D Leibfritz J Moncol M T D Cronin M Mazurand J Telser ldquoFree radicals and antioxidants in normal physio-logical functions and human diseaserdquoThe International Journalof Biochemistry amp Cell Biology vol 39 no 1 pp 44ndash84 2007
[96] D Krishnaiah R Sarbatly and R Nithyanandam ldquoA review ofthe antioxidant potential of medicinal plant speciesrdquo Food andBioproducts Processing vol 89 no 3 pp 217ndash233 2011
[97] P Liu Y Hu D-H Guo et al ldquoAntioxidant activity ofoligosaccharide ester extracted from Polygala tenuifolia roots insenescence-accelerated micerdquo Pharmaceutical Biology vol 48no 7 pp 828ndash833 2010
[98] Y Hu H-B Liao G Dai-Hong P Liu Y-Y Wang and KRahman ldquoAntidepressant-like effects of 361015840-disinapoyl sucroseon hippocampal neuronal plasticity and neurotrophic signalpathway in chronically mild stressed ratsrdquo NeurochemistryInternational vol 56 no 3 pp 461ndash465 2010
[99] Y Hu H B O Liao P Liu D-H Guo and K RahmanldquoA bioactive compound from Polygala tenuifolia regulatesefficiency of chronic stress on hypothalamic-pituitary-adrenalaxisrdquo Pharmazie vol 64 no 9 pp 605ndash608 2009
[100] A Jungbauer and SMedjakovic ldquoAnti-inflammatory propertiesof culinary herbs and spices that ameliorate the effects ofmetabolic syndromerdquoMaturitas vol 71 no 3 pp 227ndash239 2012
Evidence-Based Complementary and Alternative Medicine 23
[101] Q Xu Y Wang S Guo Z Shen and L Yang ldquoAnti-inflammatory and analgesic activity of aqueous extract of Flospopulirdquo Journal of Ethnopharmacology vol 152 no 3 pp 540ndash545 2014
[102] K S Kim D S Lee G S Bae et al ldquoThe inhibition of JNKMAPK and NF-120581B signaling by tenuifoliside A isolated fromPolygala tenuifolia in lipopolysaccharide-induced macrophagesis associated with its anti-inflammatory effectrdquo European Jour-nal of Pharmacology vol 721 no 1ndash3 pp 267ndash276 2013
[103] J-G Lee J-M Yon C Lin A Y Jung K Y Jung and S-YNamldquoCombined treatment with capsaicin and resveratrol enhancesneuroprotection against glutamate-induced toxicity in mousecerebral cortical neuronsrdquo Food and Chemical Toxicology vol50 no 11 pp 3877ndash3885 2012
[104] M L Jin S Y Park Y H Kim J-I Oh S J Lee andG Park ldquoThe neuroprotective effects of cordycepin inhibitglutamate-induced oxidative andER stress-associated apoptosisin hippocampal HT22 cellsrdquo NeuroToxicology vol 41 pp 102ndash111 2014
[105] P Liu Y Hu J Li et al ldquoProtection of SH-SY5Y neuronal cellsfrom glutamate-induced apoptosis by 36rsquo-disinapoyl sucrosea bioactive compound isolated from radix polygalardquo Journal ofBiomedicine and Biotechnology vol 2012 Article ID 728342 5pages 2012
[106] P-B Li W-L Lin Y-G Wang W Peng X-Y Cai and W-WSu ldquoAntidiabetic activities of oligosaccharides of Ophiopogonisjaponicus in experimental type 2 diabetic ratsrdquo InternationalJournal of Biological Macromolecules vol 51 no 5 pp 749ndash7552012
[107] T Liu Y M Yip L Song et al ldquoInhibiting enzymatic starchdigestion by the phenolic compound diboside A a mechanisticand in silico studyrdquo Food Research International vol 54 no 1pp 595ndash600 2013
[108] F Cote andMGHahn ldquoOligosaccharins structures and signaltransductionrdquo Plant Molecular Biology vol 26 no 5 pp 1379ndash1411 1994
[109] RACreelman and J EMullet ldquoOligosaccharins brassinolidesand jasmonates nontraditional regulators of plant growthdevelopment and gene expressionrdquo Plant Cell vol 9 no 7 pp1211ndash1223 1997
[110] L Jiao D Wan X Zhang B Li H Zhao and S LiuldquoCharacterization and immunostimulating effects on murineperitoneal macrophages of oligosaccharide isolated from Panaxginseng CAMeyerrdquo Journal of Ethnopharmacology vol 144 no3 pp 490ndash496 2012
Submit your manuscripts athttpwwwhindawicom
Stem CellsInternational
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
MEDIATORSINFLAMMATION
of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Behavioural Neurology
EndocrinologyInternational Journal of
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Disease Markers
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
BioMed Research International
OncologyJournal of
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Oxidative Medicine and Cellular Longevity
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
PPAR Research
The Scientific World JournalHindawi Publishing Corporation httpwwwhindawicom Volume 2014
Immunology ResearchHindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Journal of
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Computational and Mathematical Methods in Medicine
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Research and TreatmentAIDS
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
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Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Parkinsonrsquos Disease
Evidence-Based Complementary and Alternative Medicine
Volume 2014Hindawi Publishing Corporationhttpwwwhindawicom
12 Evidence-Based Complementary and Alternative Medicine
131130129
CH2OHOH
OH
OO
OH
C
C
HH
HHO
OO
O
HO
HOHO
HO
HOOH
OHOHOH
OHOH
HOO
O
O
O
HO
HO
OH
OHOHOH
OHOH
HOO
O
O
O
HO
Figure 3
12
3
4
5
6
1998400
2998400
3998400
4998400
5998400
6998400
HO
O
O
R1O
R2O
R8O
R7OOR3
OR4 OR5OR6
Scheme 2
antidepressant cytotoxic antineoplastic anti-inflammatoryantidiabetic plant growth-regulatory neuroprotective andcerebral protective activities Lignan-derived disaccharideesters phenylpropanoid-derived tetrasaccharide esters andpentasaccharide esterswith biological activities have not beenreported Aside from the isolated constituents oligosaccha-ride mixtures from Rehmannia glutinosa Panax ginseng andScrophularia ningpoensiswere also reported to display diversepharmacological activities such as antidiabetic immunopo-tentiating enhanced memory and antineoplastic activitiesThese active compounds and mixtures could serve as thevaluable candidates to be developed as possible drugs for thetreatment and prevention of diseases
31 Antioxidant Activity The adverse effects of oxidativestress proposed to play significant roles in the pathogenesis ofcardiovascular diseases atherosclerosis hypertension can-cer diabetes mellitus neurodegenerative diseases rheuma-toid arthritis ischemiareperfusion injury and ageing havebecome an inevitable and serious issue [95 96] Scientistshave thus made great efforts to explore antioxidants frommedicinal plants by using different kinds of assay methodswhich include DPPH radical scavenging assay hydroxylradical scavenging assay superoxide anion scavenging assayand ABTS radical scavenging method [96]
Lapathosides C and D hydropiperoside vanicoside Bhidropiperosides A and B lapathoside A and diboside Awere isolated from the Polygonum Persicaria and Fagopyrumgenera belonging to the Polygonaceae family The DPPH testrevealed that free radical-scavenging activity of the isolatedcompounds termed lapathoside C (115) hydropiperoside(42) vanicoside B (111) and lapathoside D (38) increasedin turn and lapathoside D exhibited strongest scavengingability with an IC
50of 0088 120583M [43] Hidropiperosides A
and B (117 118) were reported to show obvious antioxidantresponse to DPPH radicals with the SC
50values of 234
and 267 120583gmL respectively while vanicoside E moderatelyexhibited the same activity with a SC
50value of 490 120583gmL
[72] Lapathoside A (114) and diboside A (116) just showedlower antioxidant activities with the SC
50values of 19948 and
16552 120583M respectively [73]Smiglasides A and B smilaside P 26-di-acetyl-3101584061015840-
di-feruloylsucrose helonioside B smilasides GndashL and het-erosmilaside were isolated from the Heterosmilax and Smi-lax genera Compared with ascorbic acid (IC
5014352 120583M)
used as positive control smiglasides A and B and smi-laside P (48 49 65) (IC
5033958 33066 and 31449 120583M
resp) showed higher antioxidant activities than 26-di-acetyl-3101584061015840-di-feruloylsucrose (73) and helonioside B (40) (IC
50
63166 and 51827120583M resp) [47] Additionally Nhiem et alreported that helonioside B heterosmilaside (104) and 26-di-acetyl-3101584061015840-di-feruloylsucrose exhibited important DPPHradical scavenging activities with the SC
50values of 91 127
and 87 120583gmL respectively [48] Compared with smilasidesG-I (57ndash59) (ED
50685ndash794120583M) smilasides JndashL (60ndash62)
showed higher radical scavenging activities with an ED50
value of 267ndash327120583M [44]Five quiquesetinerviusides AndashE (105ndash109) isolated from
the Calamus genus showed weak DPPH scavenging activ-ities (IC
50604ndash1018120583M) but exhibited better hydroxyl
radical scavenging activities (IC50
36ndash84 120583M) Moreoverquiquesetinerviuside C showed superoxide anion scaveng-ing activity with an IC
50value of about 1843 120583M [70]
Liu et al investigated the antioxidant capacity of 310158406-O-di-sinapoylsucrose (DISS) (123) by using the acceleratedsenescence-prone short-lived mice (SAMP) in vivo Theanalyses indicated that the activities of antioxidant enzymesof SOD and glutathione peroxidase ascended obviously inSAMP mice when amended with DISS 50mgkg MoreoverDISS could downregulate and even restore the level ofmalondialdehyde in SAMP model group [97]
From the above studies it can be concluded that oligosac-charide esters with antioxidant activities have been identifiedin the Polygonaceae Liliaceae Smilacaceae and Arecaceaefamilies The results of the antioxidant assays show that theincreased number of phenolic hydroxyl groups and acetylgroups could produce higher antioxidant activity Fan etal indicated that the increased number of phenylpropanoidgroups was not beneficial to free radical scavenging activity[43] Zhang et al pointed out that oligosaccharide esters withferuloyl groups exhibited better antioxidant activities thanthose with coumaroyl groups [44]
Evidence-Based Complementary and Alternative Medicine 13
Table 3 Fatty acid-derived disaccharide esters
Number Name R1 R2 Source Parts Reference132 61015840-O-Linoleylsucrose H O Astragalus membranaceus Roots [77]133 61015840-O-Palmitoylsucrose H P Astragalus membranaceus Roots [77]134 6-O-Palmitoylsucrose P H Astragalus membranaceus Roots [77]
135 61015840-O-Linolenoylsucrose H N Astragalus membranaceusEquisetum hiemale
RootsAerial parts [77 78]
136 6-O-Linoleylsucrose O H Astragalus membranaceus Roots [77]137 6-O-Myristoylsucrose Q H Astragalus membranaceus Roots [77]
138 6-O-[(7Z10Z13Z)-Hexadeca-71013-trienoyl]sucrose H R Equisetum hiemale Aerial parts [78]
139 6-O-[(7Z10Z)-Hexadeca-710-dienoyl]sucrose H S Equisetum hiemale Aerial parts [78]
See Scheme 3
12
3
4
5
6
1998400
2998400
3998400
4998400
5998400
6998400
HO
O
O
R1O
R2O
R8O
R7OOR3
OR4 OR5OR6
O
O
O
18
18
1616
16
14
N linolenoyl
O linoleyl
P palmitoyl
Q myristoyl
O
O
O
R hexadeca-71013-trienoyl
S hexadeca-710-dienoyl
Scheme 3
32 Antidepressant Activity The oligosaccharides obtainedfrom the Morinda genus not only show specific antidepres-sant and antistress activities but also have no suppression orexcitatory effects on central nervous system as well Whatis more they can be taken orally with little toxicity [21]The inulin-type hexasaccharide (IHS) (9) from Morindaofficinalis obviously exhibited cytoprotective activity whichcontributed to the antidepressant effect not only by providingthe PC12 with protection against Cort-induced lesion withIHS 0625 and 125 120583Mbut also by reducing theCort-induced[Ca2+]
119894overloading with IHS 25 and 10 120583M IHS 5 and
10 120583Mupregulated the nerve growth factormRNAexpressionin Cort-induced PC12 cells [22] Polygalatenosides A (181)and B (182) were isolated from the Polygala genus Theysignificantly inhibited the isotope-labeled RTI-55 binding to
norepinephrine transporter protein with the IC50
values of300 and 604 120583M respectively [91]
DISS and tenuifoliside A were isolated from the PolygalaandCynanchum genera Liu et al investigated the antidepres-sant effect of YZ ethanol extract based on the tail suspensiontest (TST) and forced swimming test (FST) which arethe ease-of-use and widely-accepted models for estimatingantidepressant activities in mice The results indicated thatYZ-50 fraction at a dose of 200mgkgwas able to significantlydecrease the immobility time in TST Furthermore YZ-50possessed ability to inhibit corticosterone-induced injury ofhuman neuroblastoma SH-SY5Y cells What is more DISS(123) and tenuifoliside A (44) two major compounds of YZ-50 fraction showed effective protective response to the lesionin SY5Y cells [53] The antidepressant-like effect of DISS at
14 Evidence-Based Complementary and Alternative Medicine
H3CO
HO
HOHO
HO
HO
HO
HOHO
O O
OO O
OO
O
O
O
OO
O
O
OH
OH
OH
OH
OCH3
OCH3
CH2OH
CH2OH
CH2OAc
CH2OAc
H3CO
HOHO
HO
O
O
O
OO
O
O
OH
OH
OH
OCH3
CH2OH
CH2OH
H3CO
H3CO H3CO
HOHO
HO
O
O
O
OO
O
O
OH
OH
OH
OCH3
CH2OH
CH2OAc
CH3O
H
HOHO
HO
HO
HOO O
OO O
OO
OH
OCH3
CH2OHCH2OH
H3CO H3CO
H
CH2CH2 HO
HO
HO
HO
HOO O
OO O
OO
OH
OCH3
CH2OHCH2OAc
H3CO
H
CH2
140 141 142
143 144 145
Figure 4
Table 4 Phenylpropanoid-derived trisaccharide esters
Number Name R1 R2 R3 R4 R5 R6 R7 Source Parts Reference146 Tricornose C K H H H H L H Polygala tricornis Roots [37]147 Tricornose D K H H H H K H Polygala tricornis Roots [37]148 Tricornose E K H H H K L H Polygala tricornis Roots [37]149 Tricornose F K H H H I L H Polygala tricornis Roots [37]See Scheme 4
O
OOO
O
R2O
R4O
R3O
R6O
OH
OH
OH
OH
OR1
OR5CH2OR7
Scheme 4
the doses of 5 10 and 20mgkg was also tested in chronicallymild stressed rats DISS was able to exhibit antidepressantactivity by upregulating the expression of noradrenergic-regulated plasticity genes including cell adhesion moleculeL1 brain-derived neurotrophic factor laminin and cAMP
response element binding protein factor in hippocampus[98] DISS improved the reward reaction by increasingsucrose intake and obviously decreased the levels of serumcortisol adrenocorticotrophic hormone and corticotropin-releasing factor Further DISS played an enhanced role inthe expression of mineralocorticoid receptor together withglucocorticoid receptor mRNA [99]
33 Cytotoxic and Antineoplastic Activities Smilasides AndashFand P smiglasides A and B smilaside P and helonioside Awere isolated from the Smilax Trillium and Paris generaKuo et al obtained smilasides AndashF (51ndash56) and evaluatedtheir cytotoxicity against human tumor cell lines comprisinghuman oral epithelium carcinoma (KB) human cervicalcarcinoma (Hela) human colon tumor (DLD-1) humanbreast adenocarcinoma (MCF-7) human lung carcinoma (A-549) and humanmedulloblastoma (Med) cells byMTTassayExperimental data indicated that all but smilaside C showedcytotoxicity against three to six human tumor cell lines(ED50
= 51ndash130 120583gmL) and smilasides DndashF (ED50
= 27ndash50 120583gmL) displayed strong cytotoxic activities against DLD-1 cells [46]Wang et al reported the antitumor constituents of
Evidence-Based Complementary and Alternative Medicine 15
OH
OH
OH
OH
OH
OHOH
OHOH
OHOH
OH
OHOHOH
OH
OH
OH
OHOH
OH
OH
OHOH
H
H H
HO
O
O
O
O
O
O
O
OO
OO
O
OO
O
HO
HO
HO
OO
O
O
OO
OO
O
OO
O
OO
O
OO
O
O
O
OO
O
O
OO
O
OO
OOOO
HO
HO
HO
HO
HO
HO
HO
HO
HO
HO
HOHO
HO
HO
HO
HO
HO
150 151 152
153 180
AcO
AcO
AcOAcO
OAc
OAc
CH2OH
OHOH
OH OHOH
OHOH
OH
OHOH
CH3O
Figure 5
Table 5 Phenylpropanoid-derived tetrasaccharide esters
Number Name R1 R2 R3 Source Parts Reference154 Tricornose G K H K Polygala tricornis Roots [37]155 Tricornose H K K K Polygala tricornis Roots [37]156 Tricornose I K K L Polygala tricornis Roots [37]157 Tricornose J K I L Polygala tricornis Roots [37]158 Tricornose K K I K Polygala tricornis Roots [37]159 Tricornose L K G K Polygala tricornis Roots [37]See Scheme 5
Smilax riparia including smiglasides A (48) and B (49) 26-di-acetyl-3101584061015840-di-feruloylsucrose (73) helonioside B (40)and smilaside P (65) Only smiglasidesA andB and smilasideP exhibited cytotoxicity against human tumor cell lines withdifferent inhibitory concentrations comparing with cisplatinand paclitaxel as positive controls [47] Helonioside A (39)exhibited higher cytotoxicity with the increase of concentra-tion (01ndash100120583gmL) [45] Tatarisides AndashG (45 119ndash121 46122 47) and diboside A (116) from the Fagopyrum genusexerted cytotoxic activities against different human cell linesand the cytotoxicity of tatariside C was the most remarkablewith the IC
50values ranging from 644 to 749 120583gmL [57]
11015840236-O-Tetra-acetyl-31015840-O-cis-feruloylsucrose (95) fromthe Sparganium plants exhibited extremely weak cyto-toxicity against the growth of mice Lung Adenocarcinoma
795 cell lines with an IC50
value of 116 120583gmL [66] SnS-2oligosaccharides mixture including raffinose (3) stachyose(19) and verbascose (21) from the roots of Scrophularianingpoensis had antitumor activity against the growth ofLewis pulmonary carcinoma cells transplanted into mice[18]
Disaccharide esters and oligosaccharides mixture fromthe Liliaceae Polygonaceae Sparganiaceae and Scrpophular-iaceae families showed effective cytotoxic and antineoplasticactivities The study results indicated that feruloyl and acetylgroups play an important role in mediating cytotoxicitywhich seems to be related to the substitution position offeruloyl groups The feruloyl groups at C-6 or C-11015840 are vitalfor cytotoxicity In addition the increased number of acetylgroups could induce higher tumoricidal activity
16 Evidence-Based Complementary and Alternative Medicine
Table 6 Phenylpropanoid-derived pentasaccharide esters
Number Name R1 R2 R3 R4 R5 R6 Source Parts Reference160 Tenuifoliose A G D I Ac Ac Ac Polygala tenuifolia Roots [38 42]161 Tenuifoliose B G D I H Ac Ac Polygala tenuifolia Roots [42]162 Tenuifoliose C G D I H H H Polygala tenuifolia Roots [42]163 Tenuifoliose F G D U Ac Ac Ac Polygala tenuifolia Roots [42]164 Tenuifoliose G G D U Ac H Ac Polygala tenuifolia Roots [42]165 Tenuifoliose H G D G Ac Ac Ac Polygala tenuifolia Roots [38 42 79]166 Tenuifoliose I G D G Ac H Ac Polygala tenuifolia Roots [42 79]167 Tenuifoliose J G D G H Ac Ac Polygala tenuifolia Roots [42]168 Tenuifoliose K G D G H H Ac Polygala tenuifolia Roots [42]169 Tenuifoliose L G D T Ac Ac Ac Polygala tenuifolia Roots [42 79]170 Tenuifoliose M G D T Ac H Ac Polygala tenuifolia Roots [42]171 Tenuifoliose N I D I Ac Ac Ac Polygala tenuifolia Roots [42]172 Tenuifoliose O I D I H Ac Ac Polygala tenuifolia Roots [42]173 Tenuifoliose P I D I H H Ac Polygala tenuifolia Roots [42]174 Tenuifoliose Q G D T H Ac Ac Polygala tenuifolia Roots [79]175 Tenuifoliose S G D G H H H Polygala tenuifolia Roots [42]176 Tenuifoliose T G D I H H H Polygala tenuifolia Roots [42]177 Tenuifoliose V H D I Ac Ac Ac Polygala tenuifolia Roots [42]178 Tenuifoliose W I D U Ac H Ac Polygala tenuifolia Roots [42]179 Tenuifoliose X I D I H H H Polygala tenuifolia Roots [42]See Scheme 6
O
OO
O
O
O
O
OR1
OH
OH
OH
OHOH
OH
HOHO
HO
HO
OR2
R3O
CH2OH
Scheme 5
34 Anti-Inflammatory Activity Inflammation an importantbasic pathological process is a defense response of biopsywith vascular system to damage stimuli such as pathogensimpaired cells and tissues and physical and chemical factorsHowever if the process of inflammatory response cannot endnormally when cell debris and pathogens were cleared thebiological defence response will become causative factor andbring about many diseases such as diabetes cardiovasculardiseases metabolic syndrome and cancer [100 101]
Tenuifoliside A (44) from the Polygala genus exhibitedstrong anti-inflammatory effect not only by suppressing the
production of NO but also by reducing the production ofiNOS prostaglandin E2 cyclooxygenase-2 and proinflam-matory cytokines through the inhibition of the mitogen-activated protein kinases pathway and NF-120581B pathway [102]The anti-inflammatory activities of quiquesetinerviusides D(108) and E (109) from the Calamus genus were evaluated inRAW 2647 cells Both of them showed significant inhibitoryeffects against the production of LPS-stimulated NOwith theIC50values of 90ndash295120583M [70]Six disaccharide fatty acid esters (132ndash137) were iso-
lated from the Astragalus and Equisetum genera The anti-inflammatory effects of these isolated compounds have alsobeen documented The activation of NF-120581B could upregulatethe expression of proinflammatory cytokines inducible nitricoxide synthase (iNOS) and tumornecrosis factor alpha (TNF-120572) The NF-120581B inhibitory activities of compounds 132ndash137were tested in HepG2 cells stimulated with TNF-120572 All ofthese compounds could significantly restrainTNF-120572-inducedNF-120581B transcriptional activities with the IC
50values of 44ndash
247 120583M Li et al pointed out that olefinic bonds and thelength of the fatty acid moieties contributed to the NF-120581B inhibitory activity Furthermore the inhibition increasedsignificantly with the increase of the number of olefinic bondson the aliphatic moiety [77] These results may provide ascientific basis for the development of new anti-inflammatoryagents
35 Neuroprotective and Cerebral Protective Activities Aswe all know glutamate works as a major excitatory aminoacid neurotransmitter in the mammalian central nervous
Evidence-Based Complementary and Alternative Medicine 17
R6O
R2O
OR3
OR5
OR4
CH2OR1
OCH3
Rham
OO
O
OO O
O
O
O
OO
RhamO
O
OH
OH
OHOH
OH
OHOH
OHHO
HO
HO
T O-rhamnosyl-coumaroyl U O-rhamnosyl-feruloyl
Scheme 6
system and plays a crucial role in several physiological pro-cesses [103] However the accumulation of glutamate inducesdiverse acute and chronic neurodegenerative diseases suchas epilepsy ischemic stroke and Parkinsonrsquos disease aswell as Alzheimerrsquos disease [104] DISS (123) isolated fromthe Polygala genus exhibited neuroprotective effect againstglutamate-induced SH-SY5Y neuronal cell damage The invitro test demonstrated that DISS (06 6 and 60 120583molL)played a critical role in increasing cell viability controllinglactate dehydrogenase and attenuated apoptosis ranging from195 to 258 [105]
Tenuifoliside B (102) from the Polygala genus was ableto significantly shorten the coma time of KCN-inducedanoxia mice at the doses of 3 and 10mgkg and it playedan important role in ameliorating the scopolamine-inducedimpairment of performance in passive avoidance task inrats and enhancing the tremors induced by oxotremorine inmiceThese results together demonstrated that tenuifoliside Bpossessed cognitive improving and cerebral protective effects[56]
36 Antidiabetic Activity Diabetes mellitus a chronic debil-itating metabolic disease is characterized by high bloodglucose content and comprises three types termed type Itype II and gestational diabetes [106] Stachyose (19) extract(a part) from Rehmannia glutinosa obviously exhibited theactivity of downregulating fasting plasma glucose level andpartially keeping from hyperglycemia induced by adrenalineand glucose without obvious dose-dependent effect Otherthan that in vivo tests in rats induced by alloxan revealed
that stachyose extract at the dose of 200mgkg significantlydecreased blood-sugar level [15]
Diboside A lapathosides C and D vanicosides A andB and hydropiperoside were isolated from the FagopyrumPolygonum and Persicaria genera belonging to the Polygo-naceae family Diboside A (116) could potentially inhibit 120572-amylase activity with an IC
50of 269 120583M and thus retard the
starch digestion rate which is helpful for diabetic individualsin controlling blood sugar level [107] Lapathoside D (38)exerted stronger activity of 120572-glucosidase inhibition with anIC50
value of 0113mM than acarbose which was chosen asa positive drug for the treatment of type II diabetes [43]Vanicoside B (111) was reported to have higher 120573-glucosidaseinhibitory activity with an IC
50of 505 120583M than vanicoside A
(110) with an IC50of 599 120583M because of the acetyl moiety of
the latter possibly decreasing inhibitory activity of vanicosideA [71]
Fujimoto et al investigated the inhibitory effects ofmumeoses FndashO (83ndash92) from the Prunus genus on aldosereductase and discovered that caffeoyl groups are crucialfor the inhibitory effect on aldose reductase And thusmumeoses F G H J K L M and N (IC
50= 22ndash77120583M) with
a coumaroyl group and acetyl groups inhibited moderatelyaldose reductase from reducing glucose to sorbitol whichis associated with the chronic complications of diabetes [6364]
37 Elicitors and Regulators Oligosaccharides are quitepropitious for encoding biological information because ofdiverse monosaccharide units and complex molecular struc-tures and they are therefore first described as biological
18 Evidence-Based Complementary and Alternative Medicine
181 H
H
H
H
H
H
H
H
H H
H
H
H
H
H
H
H H
HH
Benzyl
Benzyl
Benzyl
182
183
184 Ac
Ac
Ac
Ac
Ac
Ac
Ac
Ac
Ac
Ac
185
186
187
188
189
R1 R2 R3
R1 R2 R3 R4
OCH3
R3OH2C OR2
OR1
OR1
O
O
O
O O
OOO
O
OO
O
OH
OH
OH OH
OH
O O
O
O
OH
HO
OH
OH OHOH
OH
OH
OHHO
HO
OH
OH
HO
CH2OH
CH2OH
CH2OH
CH2OH
C
R2O
R3O
CH2OR4
CH2CH2 CH2CH2CH2CH2CH3
CH3
CH3
191190 192
193
O
C C
O
OO
OO
OO
OO
O O
O
O
O
O
O
O
OH
OH
OHHO
HO
HOOH
OH
OH
OH
HO
OH
OH
OH
OH
HO
HO
C C
R998400O
R998400
Figure 6
signals in plants [108] Oligosaccharides from the cell wallfragments of plants and fungi are powerful signal moleculessuch as the elicitors of plant defence response and theregulators of plant growth and they are capable of exertingbiological activities at exceedingly low concentrations [109]Heptasaccharide (HS) (15) and octasaccharide (OS) (16) iso-lated from the Paris genus possessed plant growth-regulatory
activities [29 30]The two oligosaccharides significantly pro-moted the proliferation of Paris polyphylla var yunnanensisroots at the doses of 25ndash20mgL The octasaccharide hadthe most obvious effect on the growth of Panax japonicusvar major hairy roots at a dose of 30mgL while the otherhad the most positive effect on saponin accumulation ofPanax japonicus var major hairy roots at a dose of 10mgL
Evidence-Based Complementary and Alternative Medicine 19
[29] Similarly Zhou et al evaluated the stimulating effectsof HS and OS on the root growth and saponin productionof Panax ginseng hairy roots which were induced from theplant roots infected withAgrobacterium rhizogenes strain A4The results showed that there was a maximum effect on thehairy roots growth and saponin accumulation on day 10Compared with control group the root biomass dry weightwas increased by more than 17-fold while the total saponincontent of roots increased by more than 1-fold when thesetwo oligosaccharides were added to the hairy root at a dose of30mgL [30] The above data illustrate that HS and OS couldserve as the plant growth-regulators not only in their originalspecies but also in others
38 Immunopotentiating Activity Macrophages are impor-tant targets of investigations on cytophagy cellular immunityand molecular immunology Therefore they are deemedto play a vital role in host defense comprising phagocy-tosis proteolytic processing pathogenic agent apoptosiscytokines production and foreign antigens presentation[110] The water-extracted oligosaccharides from Panax gin-seng (WGOS) exhibited better immunopotentiating activ-ity by increasing phagocytic function of macrophages andpromoting NO TNF-120572 and reactive oxygen species pro-duction [110] In addition Wan et al have obtained malto-oligosaccharides (17 119899 = 3sim8) and three oligosaccharides (213 14) from the Panax ginseng roots The in vitro bioassaypointed out thatWGOS could serve as efficacious stimulatorsof B and T lymphocytes [28] These studies provided enlight-enment that the mixture of oligosaccharides from Chineseherbalmedicine exhibits significant effect on immune system
39 Others Acetylcholinesterase (AChE) inhibitors showgood therapeutic effects onmyasthenia gravis glaucoma andAlzheimerrsquos disease through reversible enzyme inhibitionso as to increase the accumulation of acetylcholine in thesynapse and then promote and prolong the function ofacetylcholine Vanicoside B (111) showed AChE inhibitoryactivity with an IC
50of 0062mM while hydropiperoside
(42) and lapathosides C (115) and D (38) just exhibited weakenzyme inhibitory activity [43]
Wang et al has explored low molecular mass carbohy-drate polymer from Panax ginseng roots and obtained 30ethanol elution (PGO)which included peptides and oligosac-charides (17 119899 = 0sim5) identified as maltose maltotriosemaltotetraose maltopentaose maltohexaose and maltohep-taose Pharmacological experiments revealed that PGO couldsignificantly enhance the memory in scopolamine-inducedmemory deficit rats [27]
Cistanoside F (129) and kankanose (150) were isolatedfrom the Cistanche Paulownia and Acanthus genera Phar-macological experiments showed that cistanoside F andkankanose significantly exhibited vasorelaxant effects on thenoradrenaline-induced contraction of thoracic aorta fromrats [80]
4 Conclusion
Traditional Chinese medicine from natural kingdom playsan indelible role in the treatment of human diseases andit has aroused the attention of those who have engagedin medicinal pharmaceutical chemistry Therefore scientistshave made great contributions day after day to investigate thevalid chemicals from traditional Chinese medicines In thepast decades about 193 oligosaccharides and their esters havebeen identified from traditional Chinese medicinal plantsOn the one hand only a few oligosaccharides and theirmixtures were investigated and just exhibited antidepres-sant antineoplastic antidiabetic plant growth-regulatoryimmunopotentiating and enhancedmemory activitiesMoreexploratory work is still needed to excavate biological andpharmacological activities of oligosaccharides On the otherhand oligosaccharide esters exhibited multi-advantageousactivities Bioassays have revealed that antioxidant cytotoxicantineoplastic and anti-inflammatory activities are the mostnotable bioactivities Of course to search for the naturalproducts with these activities is a hotpot in the contemporarydrug research Oligosaccharide esters provide a vast treasuretrove for medical researchers After considering the currentstudies it should be taken as future directions to makemore mechanism of action studies and clinical trials tofurther evaluate its potential as new drugs Moreover thestructure-activity relationships discussed in this review willprovide reference information for further exploring theirrelationships and continually discovering the new bioactiveoligosaccharide esters
Conflict of Interests
The authors declare that there is no conflict of interestsregarding the publication of this paper
References
[1] X D Yang L J Zhang B Liang L Z Xu and S L YangldquoOligosaccharide esters isolated from plants of PolygalaceaerdquoChinese Traditional and Herbal Drugs vol 33 no 10 pp 954ndash958 2002
[2] N Ogwuru and M Adamczeski ldquoBioactive natural productsderived from Polygonum species of plants their structures andmechanisms of actionrdquo Studies in Natural Products Chemistryvol 22 pp 607ndash642 2000
[3] S Kobayashi T Miyase and H Noguchi ldquoPolyphenolic glyco-sides and oligosaccharide multiesters from the roots of Polygaladalmaisianardquo Journal of Natural Products vol 65 no 3 pp 319ndash328 2002
[4] M Takasaki S Kuroki M Kozuka and T Konoshima ldquoNewphenylpropanoid esters of sucrose from Polygonum lapathi-foliumrdquo Journal of Natural Products vol 64 no 10 pp 1305ndash1308 2001
[5] M L Zimmermann and A T Sneden ldquoVanicosides A and Bprotein kinase C inhibitors from Polygonum pensylvanicumrdquoJournal of Natural Products vol 57 no 2 pp 236ndash242 1994
[6] M Takasaki T Konoshima S Kuroki H Tokuda and HNishino ldquoCancer chemopreventive activity of phenylpropanoid
20 Evidence-Based Complementary and Alternative Medicine
esters of sucrose vanicoside B and lapathoside A from Poly-gonum lapathifoliumrdquo Cancer Letters vol 173 no 2 pp 133ndash138 2001
[7] Q Fu T Liang Z Y Li et al ldquoSeparation of carbohydrates usinghydrophilic interaction liquid chromatographyrdquo CarbohydrateResearch vol 379 pp 13ndash17 2013
[8] M F Mrozek D Zhang and D Ben-Amotz ldquoOligosaccharideidentification and mixture quantification using Raman spec-troscopy and chemometric analysisrdquo Carbohydrate Researchvol 339 no 1 pp 141ndash145 2004
[9] G S Armstrong and B Bendiak ldquoHigh-resolution four-dimen-sional carbon-correlated 1H-1H ROESY experiments employ-ing isotags and the filter diagonalization method for effectiveassignment of glycosidic linkages in oligosaccharidesrdquo Journalof Magnetic Resonance vol 181 no 1 pp 79ndash88 2006
[10] G S Armstrong V A Mandelshtam A J Shaka and BBendiak ldquoRapid high-resolution four-dimensional NMR spec-troscopy using the filter diagonalization method and its advan-tages for detailed structural elucidation of oligosaccharidesrdquoJournal of Magnetic Resonance vol 173 no 1 pp 160ndash168 2005
[11] H-M Tseng S Gattolin J Pritchard H J Newbury and DA Barrett ldquoAnalysis of mono- di- and oligosaccharides by CEusing a two-stage derivatization method and LIF detectionrdquoElectrophoresis vol 30 no 8 pp 1399ndash1405 2009
[12] N Li X Li B L Hou and D L Meng ldquoNew disaccharosidefrom Camptosorus sibiricus Ruprrdquo Natural Product Researchvol 22 no 15 pp 1379ndash1383 2008
[13] Z Zhang D Wang Y Zhao H Gao Y-H Hu and J-FHu ldquoFructose-derived carbohydrates from Alisma orientalisrdquoNatural Product Research vol 23 no 11 pp 1013ndash1020 2009
[14] X Yang Y Zhao N He and K D Croft ldquoIsolation char-acterization and immunological effects of 120572-galacto-oligo-saccharides from a new source the herb Lycopus lucidus TurczrdquoJournal of Agricultural and Food Chemistry vol 58 no 14 pp8253ndash8258 2010
[15] R X Zhang Z P Jia L Y Kong et al ldquoStachyose extractfrom Rehmannia glutinosa Libosch to lower plasma glucose innormal and diabetic rats by oral administrationrdquo Pharmazievol 59 no 7 pp 552ndash556 2004
[16] R Zhang Y Zhao Y Sun X Lu and X Yang ldquoIsolationcharacterization and hepatoprotective effects of the raffinosefamily oligosaccharides from Rehmannia glutinosa liboschrdquoJournal of Agricultural and Food Chemistry vol 61 no 32 pp7786ndash7793 2013
[17] H Li F Song Z Zheng Z Liu and S Liu ldquoCharacterization ofsaccharides and phenolic acids in the Chinese herb Tanshen byESI-FT-ICR-MS and HPLCrdquo Journal of Mass Spectrometry vol43 no 11 pp 1545ndash1552 2008
[18] J E Deng J Zhang XM ChenW Ke and G Y Tian ldquoStudieson the physicochemical properties structure and antitumoractivity of an oligosaccharide homologue SnS-2 from the root ofScrophularia ningpoensis Hemslrdquo Chinese Journal of Chemistryvol 22 no 5 pp 492ndash497 2004
[19] S C Chou LM Chuang and S S Lee ldquoHypoglycemic constit-uents of gynura divaricata subsp formosanardquo Natural ProductCommunications vol 7 no 2 pp 221ndash222 2012
[20] F Feng L-L Wang X-P Lai Y-B Li Z-M Cao and Y-J Zhou ldquoStudy on oligosaccharides from Morinda officinalisrdquoJournal of Chinese Medicinal Materials vol 35 no 8 pp 1259ndash1262 2012
[21] Y F Li Z H Gong M Yang Y M Zhao and Z P Luo ldquoInhibi-tion of the oligosaccharides extracted fromMorinda officinalis
a Chinese traditional herbal medicine on the corticosteroneinduced apoptosis in PC12 cellsrdquo Life Sciences vol 72 no 8 pp933ndash942 2003
[22] Y-F Li Y-Q Liu M Yang et al ldquoThe cytoprotective effect ofinulin-type hexasaccharide extracted from Morinda officinalison PC12 cells against the lesion induced by corticosteronerdquo LifeSciences vol 75 no 13 pp 1531ndash1538 2004
[23] D N Olennikov L M Tankhaeva and A V Rokhin ldquoGlu-cofructans from Saussurea lappa rootsrdquo Chemistry of NaturalCompounds vol 47 no 3 pp 339ndash342 2011
[24] S K Hyun H A Jung B S Min J H Jung and J S ChoildquoIsolation of phenolics nucleosides saccharides and an alkaloidfrom the root of Aralia cordatardquo Natural Product Sciences vol16 no 1 pp 20ndash25 2010
[25] Z J Xu C W Lin and M F Liao ldquoStructure analysis of a newoligosaccharides BROS from Blumea ripariardquo Chinese Journalof Organic Chemistry vol 31 no 11 pp 1811ndash1819 2011
[26] Z J Xu C W Lin and Y Shi ldquoIsolation and structuredetermination of a new oligosaccharide from Blume ripariardquoJournal of Medicinal Plants Research vol 5 no 14 pp 2956ndash2962 2011
[27] Y Wang R Z Jiang G R Li et al ldquoStructural and enhancedmemory activity studies of extracts from Panax ginseng rootrdquoFood Chemistry vol 119 no 3 pp 969ndash973 2010
[28] DWan L Jiao H Yang and S Liu ldquoStructural characterizationand immunological activities of the water-soluble oligosaccha-rides isolated from thePanax ginseng rootsrdquoPlanta vol 235 no6 pp 1289ndash1297 2012
[29] L G Zhou C Z Yang J Q Li S L Wang and J Y WuldquoHeptasaccharide and octasaccharide isolated from Paris pol-yphylla var yunnanensis and their plant growth-regulatoryactivityrdquo Plant Science vol 165 no 3 pp 571ndash575 2003
[30] L G Zhou X D Cao R F Zhang Y L Peng S J Zhao andJ Y Wu ldquoStimulation of saponin production in Panax ginsenghairy roots by two oligosaccharides from Paris polyphylla varyunnanensisrdquo Biotechnology Letters vol 29 no 4 pp 631ndash6342007
[31] M Vanhaecke W van den Ende E Lescrinier and N Dyu-bankova ldquoIsolation and characterization of a pentasaccharidefrom Stellaria mediardquo Journal of Natural Products vol 71 no 11pp 1833ndash1836 2008
[32] J Feng and W Zhao ldquoComplete 1Hand 13C NMR assignmentsof four new oligosaccharides and two new glycosides fromPeriploca forrestiirdquoMagnetic Resonance in Chemistry vol 47 no8 pp 701ndash705 2009
[33] J Q Feng R J Zhang Y Zhou et al ldquoImmunosuppressive preg-nane glycosides from Periploca sepium and Periploca forrestiirdquoPhytochemistry vol 69 no 15 pp 2716ndash2723 2008
[34] X H Long R Xu Y H Zhang X H Tan andQ Y Sun ldquoA newoligosaccharide from Periploca calophyllardquo Zhongguo ZhongyaoZazhi vol 37 no 2 pp 226ndash229 2012
[35] L Wang Z-Q Yin Y Wang X-Q Zhang Y-L Li and W-CYe ldquoPerisesaccharides A-E new oligosaccharides from the rootbarks ofPeriploca sepiumrdquoPlantaMedica vol 76 no 9 pp 909ndash915 2010
[36] T Lei L Zhang H-Y Jiang Y Hu A-H Hong and Y-Z CenldquoA new pregnane glycoside and oligosaccharide from Parabar-ium huaitingiirdquo Journal of Asian Natural Products Research vol13 no 11 pp 1030ndash1035 2011
[37] J Li Y Jiang and P F Tu ldquoTricornoses A-L oligosaccharidemulti-esters from the roots of Polygala tricornisrdquo Journal ofNatural Products vol 68 no 5 pp 739ndash744 2005
Evidence-Based Complementary and Alternative Medicine 21
[38] H H Tu P Liu L Mu et al ldquoStudy on antidepressant com-ponents of sucrose ester from Polygala tenuifoliardquo ZhongguoZhongyao Zazhi vol 33 no 11 pp 1278ndash1280 2008
[39] G M She Y Y Ba Y Liu H Lv W Wang and R B ShildquoAbsorbable phenylpropenoyl sucroses from Polygala tenuifo-liardquoMolecules vol 16 no 7 pp 5507ndash5513 2011
[40] J Yong and P F Tu ldquoStudies on the chemical constituents inroot bark of Polygala tenuifolia (II)rdquo China Journal of ChineseMateria Medica vol 29 no 8 pp 751ndash753 2004
[41] M Ono C Takamura F Sugita et al ldquoTwo new steroidglycosides and a new sesquiterpenoid glycoside from theunderground parts of Trillium kamtschaticumrdquo Chemical andPharmaceutical Bulletin vol 55 no 4 pp 551ndash556 2007
[42] Y Ling Z Li M Chen Z Sun M Fan and C HuangldquoAnalysis and detection of the chemical constituents of RadixPolygalae and their metabolites in rats after oral administrationby ultra high-performance liquid chromatography coupledwith electrospray ionization quadrupole time-of-flight tandemmass spectrometryrdquo Journal of Pharmaceutical and BiomedicalAnalysis vol 85 pp 1ndash13 2013
[43] P Fan L Terrier A-E Hay A Marston and K HostettmannldquoAntioxidant and enzyme inhibition activities and chemicalprofiles ofPolygonum sachalinensis FSchmidt exMaxim (Polyg-onaceae)rdquo Fitoterapia vol 81 no 2 pp 124ndash131 2010
[44] L J Zhang C C Liao H C Huang Y C Shen L M Yangand Y H Kuo ldquoAntioxidant phenylpropanoid glycosides fromSmilax bracteatardquo Phytochemistry vol 69 no 6 pp 1398ndash14042008
[45] L L Yan W Y Gao Y J Zhang and Y Wang ldquoA new phenyl-propanoid glycosides from Paris polyphylla var yunnanensisrdquoFitoterapia vol 79 no 4 pp 306ndash307 2008
[46] Y H Kuo Y W Hsu C C Liaw J K Lee H C Huang andL M Y Kuo ldquoCytotoxic phenylpropanoid glycosides from thestems of Smilax chinardquo Journal of Natural Products vol 68 no10 pp 1475ndash1478 2005
[47] W-X Wang T-X Li H Ma J-F Zhang and A-Q JialdquoTumoral cytotoxic and antioxidative phenylpropanoid glyco-sides in Smilax riparia A DCrdquo Journal of Ethnopharmacologyvol 149 no 2 pp 527ndash532 2013
[48] N X Nhiem P vanKiem C vanMinh et al ldquoPhenylpropanoidglycosides fromHeterosmilax erythrantha and their antioxidantactivityrdquo Archives of Pharmacal Research vol 32 no 10 pp1373ndash1377 2009
[49] Y Wang W Y Gao T J Zhang and Y Q Guo ldquoA novelphenylpropanoid glycosides and a new derivation of phenolicglycoside from Paris Polyphylla var yunnanensisrdquo ChineseChemical Letters vol 18 no 5 pp 548ndash550 2007
[50] J-Y Zhang Y-Z Wang Y-L Zhao et al ldquoPhytochemicals andbioactivities of Paris speciesrdquo Journal of Asian Natural ProductsResearch vol 13 no 7 pp 670ndash681 2011
[51] N H N Hashim F Abas K Shaari and N H Lajis ldquoLC-DAD-ESIMSMS characterization of antioxidant and anti-cholinesterase constituents present in the active fraction fromPersicaria hydropiperrdquo LWT Food Science and Technology vol46 no 2 pp 468ndash476 2012
[52] PH FanA EHayAMarstonHX Lou andKHostettmannldquoChemical variability of the invasive neophytes Polygonumcuspidatum Sieb and Zucc and Polygonum sachalinensis FSchmidt ex Maximrdquo Biochemical Systematics and Ecology vol37 no 1 pp 24ndash34 2009
[53] P Liu Y Hu D H Guo et al ldquoPotential antidepressantproperties of Radix Polygalae (Yuan Zhi)rdquo Phytomedicine vol17 no 10 pp 794ndash799 2010
[54] J F Wu S B Chen S L Chen and P F Tu ldquoThe chemical con-stituents of Polygala hongkongensisHemslrdquoActa PharmaceuticaSinica vol 42 no 7 pp 757ndash761 2007
[55] Y Song Y Jiang D Bi X Tian L Liang and P Tu ldquoChemicalconstituents from n-butanol extract of aerial part of Polygalasibiricardquo Zhongguo Zhongyao Zazhi vol 37 no 4 pp 471ndash4742012
[56] Y Ikeya S Takeda M Tunakawa et al ldquoCognitive improvingand cerebral protective effects of acylated oligosaccharides inPolygala tenuifoliardquo Biological and Pharmaceutical Bulletin vol27 no 7 pp 1081ndash1085 2004
[57] C J Zheng C L Hu X Q Ma C Peng H Zhang and L PQin ldquoCytotoxic phenylpropanoid glycosides from Fagopyrumtataricum (L) Gaertnrdquo Food Chemistry vol 132 no 1 pp 433ndash438 2012
[58] X Li Y F Zhang L Yang et al ldquoChemical profiling ofconstituents of Smilacis glabrae using ultra-high pressure liquidchromatography coupled with LTQ orbitrap mass spectrome-tryrdquo Natural Product Communications vol 7 no 2 pp 181ndash1842012
[59] T-T Sun D-W Zhang Y Han F-Y Dong andWWang ldquoSmi-lasides M and N two new phenylpropanoid glycosides fromSmilax ripariardquo Journal of Asian Natural Products Research vol14 no 2 pp 165ndash170 2012
[60] J Li X Bi G Zheng Y Hitoshi T Ikeda and T NoharaldquoSteroidal glycosides and aromatic compounds from Smilaxripariardquo Chemical amp Pharmaceutical Bulletin vol 54 no 10 pp1451ndash1454 2006
[61] N Wang X Yao R Ishii and S Kitanaka ldquoBioactive sucroseesters from Bidens parviflorardquo Phytochemistry vol 62 no 5 pp741ndash746 2003
[62] S Nakamura K Fujimoto T Matsumoto et al ldquoAcylatedsucroses and acylated quinic acids analogs from the flower budsof Prunus mume and their inhibitory effect on melanogenesisrdquoPhytochemistry vol 92 pp 128ndash136 2013
[63] K Fujimoto SNakamura TMatsumoto et al ldquoMedicinal flow-ers XXXVIII Structures of acylated sucroses and inhibitoryeffects of constituents on aldose reducatase from the flower budsofPrunusmumerdquoChemical and Pharmaceutical Bulletin vol 61no 4 pp 445ndash451 2013
[64] S Nakamura K Fujimoto T Matsumoto et al ldquoStructuresof acylated sucroses and an acylated flavonol glycoside andinhibitory effects of constituents on aldose reductase from theflower buds of Prunus mumerdquo Journal of Natural Medicines vol67 no 4 pp 799ndash806 2013
[65] L-B Dong J He X-Y Li et al ldquoChemical constituents fromthe aerial parts of Musella lasiocarpardquo Natural Products andBioprospecting vol 1 no 1 pp 41ndash47 2011
[66] Y Xiong K Z Deng Y Q Guo W Y Gao and T J ZhangldquoNew chemical constituents from the rhizomes of Sparganiumstoloniferumrdquo Archives of Pharmacal Research vol 32 no 5 pp717ndash720 2009
[67] Y Xiong K-Z Deng Y-Q Guo W-Y Gao and T-J ZhangldquoTwo new sucrose esters from Sparganium stoloniferumrdquo Jour-nal of Asian Natural Products Research vol 10 no 5 pp 425ndash428 2008
[68] B Chen N L Wang J H Huang and X S Yao ldquoIridoidand phenylpropanoid glycosides from Scrophularia ningpoensis
22 Evidence-Based Complementary and Alternative Medicine
Hemslrdquo Asian Journal of Traditional Medicines vol 2 no 3 pp119ndash123 2007
[69] H Chen Y Z Zhou L Qiao et al ldquoTwo new compounds fromCynanchum amplexicaulerdquo Journal of Asian Natural ProductsResearch vol 10 no 3 pp 248ndash251 2008
[70] C-L Chang L-J Zhang R Y Chen et al ldquoAntioxidant andanti-inflammatory phenylpropanoid derivatives from Calamusquiquesetinerviusrdquo Journal of Natural Products vol 73 no 9 pp1482ndash1488 2010
[71] Y Kawai H Kumagai H Kurihara K Yamazaki R Sawanoand N Inoue ldquo120573-Glucosidase inhibitory activities of phenyl-propanoid glycosides vanicoside A and B from Polygonumsachalinense rhizomerdquo Fitoterapia vol 77 no 6 pp 456ndash4592006
[72] P V Kiem N X Nhiem N X Cuong et al ldquoNew phenyl-propanoid esters of sucrose from Polygonum hydropiper andtheir antioxidant activityrdquo Archives of Pharmacal Research vol31 no 11 pp 1477ndash1482 2008
[73] K J Wang Y J Zhang and C R Yang ldquoAntioxidant phenolicconstituents from Fagopyrum dibotrysrdquo Journal of Ethnophar-macology vol 99 no 2 pp 259ndash264 2005
[74] N Cho J Huh H Yang et al ldquoChemical constituentsof Polygala tenuifolia roots and their inhibitory activity onlipopolysaccharide-induced nitric oxide production in BV2microgliardquo Journal of Enzyme Inhibition and Medicinal Chem-istry vol 27 no 1 pp 1ndash4 2012
[75] Q Ren C S Wu and J L Zhang ldquoUse of on-line stop-flowheart-cutting two-dimensional high performance liquid chro-matography for simultaneous determination of 12 major con-stituents in tartary buckwheat (Fagopyrum tataricum Gaertn)rdquoJournal of Chromatography A vol 1304 pp 257ndash262 2013
[76] Q Ren C S Wu Y Ren and J L Zhang ldquoCharacterizationand identification of the chemical constituents from tartarybuckwheat (Fagopyrum tataricumGaertn) by high performanceliquid chromatographyphotodiode array detectorlinear iontrap FTICR hybrid mass spectrometryrdquo Food Chemistry vol136 no 3-4 pp 1377ndash1389 2013
[77] W Li Y N Sun X T Yan et al ldquoNF-120581B inhibitory activityof sucrose fatty acid esters and related constituents fromAstragalus membranaceusrdquo Journal of Agricultural and FoodChemistry vol 61 no 29 pp 7081ndash7088 2013
[78] J T Cheng J He Y Li et al ldquoThree new sucrose fatty acid estersfrom Equisetum hiemale LrdquoHelvetica Chimica Acta vol 95 no7 pp 1158ndash1163 2012
[79] Y Jiang and P-F Tu ldquoTenuifoliose Q a new oligosaccharideester from the root of Polygala tenuifoliaWilldrdquo Journal of AsianNatural Products Research vol 5 no 4 pp 279ndash283 2003
[80] M Yoshikawa H Matsuda T Morikawa H H Xie S Naka-mura and O Muraoka ldquoPhenylethanoid oligoglycosides andacylated oligosugars with vasorelaxant activity from Cistanchetubulosardquo Bioorganic ampMedicinal Chemistry vol 14 no 22 pp7468ndash7475 2006
[81] P-F Tu H-M Shi Z-H Song Y Jiang and Y-Y ZhaoldquoChemical constituents of Cistanche sinensisrdquo Journal of AsianNatural Products Research vol 9 no 1 pp 79ndash84 2007
[82] C-L Si Y-Y Lu P-P Qin R-C Sun and Y-H Ni ldquoPhenolicextractives with chemotaxonomic significance from the bark ofPaulownia tomentosa var tomentosardquo BioResources vol 6 no4 pp 5086ndash5098 2011
[83] J Wu S Zhang Q Xiao et al ldquoPhenylethanoid and aliphaticalcohol glycosides from Acanthus ilicifoliusrdquo Phytochemistryvol 63 no 4 pp 491ndash495 2003
[84] Y Jiang and P-F Tu ldquoAnalysis of chemical constituents inCistanche speciesrdquo Journal of Chromatography A vol 1216 no11 pp 1970ndash1979 2009
[85] H Otsuka H Kuwabara and H Hoshiyama ldquoIdentification ofsucrose diesters of aryldihydronaphthalene-type lignans fromTrigonotis peduncularisand the nature of their fluorescencerdquoJournal of Natural Products vol 71 no 7 pp 1178ndash1181 2008
[86] M-R Suo J-S Yang and Q-H Liu ldquoLignan oligosaccharideesters from Eritrichium rupestrerdquo Journal of Natural Productsvol 69 no 4 pp 682ndash684 2006
[87] P-F Tu Z-H Song H-M Shi Y Jiang and Y-Y ZhaoldquoArylethyl (=phenylethanoid) glycosides and oligosaccharidefrom the stem of Cistanche tubulosardquo Helvetica Chimica Actavol 89 no 5 pp 927ndash935 2006
[88] M-H Shyr T-H Tsai and L-C Lin ldquoRossicasins A Band rosicaside F three new phenylpropanoid glycosides fromBoschniakia rossicardquoChemical and Pharmaceutical Bulletin vol54 no 2 pp 252ndash254 2006
[89] R FangNCVeitchGCKiteM J RHowes EA Porter andM S J Simmonds ldquoGlycosylated constituents of Iris fulvaandIris brevicaulisrdquoChemical amp Pharmaceutical Bulletin vol 59 no1 pp 124ndash128 2011
[90] J Fu L Zuo J Yang R Chen and D Zhang ldquoOligosaccharidepolyester and triterpenoid saponins from the roots of Polygalajaponicardquo Phytochemistry vol 69 no 7 pp 1617ndash1624 2008
[91] M-C Cheng C-Y Li H-C Ko F-N Ko Y-L Lin andT-S Wu ldquoAntidepressant principles of the roots of polygalatenuifoliardquo Journal of Natural Products vol 69 no 9 pp 1305ndash1309 2006
[92] H T Chang and P F Tu ldquoNew oligosaccharide esters andxanthone C-glucosides from Polygala telephioidesrdquo HelveticaChimica Acta vol 90 no 5 pp 944ndash950 2007
[93] J Li L Feng J Dai R Wang and T Nohara ldquoChemical con-stituents from Polygala telephioidesrdquo China Journal of ChineseMateria Medica vol 34 no 4 pp 402ndash405 2009
[94] W-P Yin T-Z Zhao and H-Y Zhang ldquoA novel oligosaccha-ride ester from Syringa pubescensrdquo Journal of Asian NaturalProducts Research vol 10 no 1 pp 95ndash100 2008
[95] M Valko D Leibfritz J Moncol M T D Cronin M Mazurand J Telser ldquoFree radicals and antioxidants in normal physio-logical functions and human diseaserdquoThe International Journalof Biochemistry amp Cell Biology vol 39 no 1 pp 44ndash84 2007
[96] D Krishnaiah R Sarbatly and R Nithyanandam ldquoA review ofthe antioxidant potential of medicinal plant speciesrdquo Food andBioproducts Processing vol 89 no 3 pp 217ndash233 2011
[97] P Liu Y Hu D-H Guo et al ldquoAntioxidant activity ofoligosaccharide ester extracted from Polygala tenuifolia roots insenescence-accelerated micerdquo Pharmaceutical Biology vol 48no 7 pp 828ndash833 2010
[98] Y Hu H-B Liao G Dai-Hong P Liu Y-Y Wang and KRahman ldquoAntidepressant-like effects of 361015840-disinapoyl sucroseon hippocampal neuronal plasticity and neurotrophic signalpathway in chronically mild stressed ratsrdquo NeurochemistryInternational vol 56 no 3 pp 461ndash465 2010
[99] Y Hu H B O Liao P Liu D-H Guo and K RahmanldquoA bioactive compound from Polygala tenuifolia regulatesefficiency of chronic stress on hypothalamic-pituitary-adrenalaxisrdquo Pharmazie vol 64 no 9 pp 605ndash608 2009
[100] A Jungbauer and SMedjakovic ldquoAnti-inflammatory propertiesof culinary herbs and spices that ameliorate the effects ofmetabolic syndromerdquoMaturitas vol 71 no 3 pp 227ndash239 2012
Evidence-Based Complementary and Alternative Medicine 23
[101] Q Xu Y Wang S Guo Z Shen and L Yang ldquoAnti-inflammatory and analgesic activity of aqueous extract of Flospopulirdquo Journal of Ethnopharmacology vol 152 no 3 pp 540ndash545 2014
[102] K S Kim D S Lee G S Bae et al ldquoThe inhibition of JNKMAPK and NF-120581B signaling by tenuifoliside A isolated fromPolygala tenuifolia in lipopolysaccharide-induced macrophagesis associated with its anti-inflammatory effectrdquo European Jour-nal of Pharmacology vol 721 no 1ndash3 pp 267ndash276 2013
[103] J-G Lee J-M Yon C Lin A Y Jung K Y Jung and S-YNamldquoCombined treatment with capsaicin and resveratrol enhancesneuroprotection against glutamate-induced toxicity in mousecerebral cortical neuronsrdquo Food and Chemical Toxicology vol50 no 11 pp 3877ndash3885 2012
[104] M L Jin S Y Park Y H Kim J-I Oh S J Lee andG Park ldquoThe neuroprotective effects of cordycepin inhibitglutamate-induced oxidative andER stress-associated apoptosisin hippocampal HT22 cellsrdquo NeuroToxicology vol 41 pp 102ndash111 2014
[105] P Liu Y Hu J Li et al ldquoProtection of SH-SY5Y neuronal cellsfrom glutamate-induced apoptosis by 36rsquo-disinapoyl sucrosea bioactive compound isolated from radix polygalardquo Journal ofBiomedicine and Biotechnology vol 2012 Article ID 728342 5pages 2012
[106] P-B Li W-L Lin Y-G Wang W Peng X-Y Cai and W-WSu ldquoAntidiabetic activities of oligosaccharides of Ophiopogonisjaponicus in experimental type 2 diabetic ratsrdquo InternationalJournal of Biological Macromolecules vol 51 no 5 pp 749ndash7552012
[107] T Liu Y M Yip L Song et al ldquoInhibiting enzymatic starchdigestion by the phenolic compound diboside A a mechanisticand in silico studyrdquo Food Research International vol 54 no 1pp 595ndash600 2013
[108] F Cote andMGHahn ldquoOligosaccharins structures and signaltransductionrdquo Plant Molecular Biology vol 26 no 5 pp 1379ndash1411 1994
[109] RACreelman and J EMullet ldquoOligosaccharins brassinolidesand jasmonates nontraditional regulators of plant growthdevelopment and gene expressionrdquo Plant Cell vol 9 no 7 pp1211ndash1223 1997
[110] L Jiao D Wan X Zhang B Li H Zhao and S LiuldquoCharacterization and immunostimulating effects on murineperitoneal macrophages of oligosaccharide isolated from Panaxginseng CAMeyerrdquo Journal of Ethnopharmacology vol 144 no3 pp 490ndash496 2012
Submit your manuscripts athttpwwwhindawicom
Stem CellsInternational
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
MEDIATORSINFLAMMATION
of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Behavioural Neurology
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Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Disease Markers
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
BioMed Research International
OncologyJournal of
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Oxidative Medicine and Cellular Longevity
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
PPAR Research
The Scientific World JournalHindawi Publishing Corporation httpwwwhindawicom Volume 2014
Immunology ResearchHindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Journal of
ObesityJournal of
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Computational and Mathematical Methods in Medicine
OphthalmologyJournal of
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Research and TreatmentAIDS
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Gastroenterology Research and Practice
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Parkinsonrsquos Disease
Evidence-Based Complementary and Alternative Medicine
Volume 2014Hindawi Publishing Corporationhttpwwwhindawicom
Evidence-Based Complementary and Alternative Medicine 13
Table 3 Fatty acid-derived disaccharide esters
Number Name R1 R2 Source Parts Reference132 61015840-O-Linoleylsucrose H O Astragalus membranaceus Roots [77]133 61015840-O-Palmitoylsucrose H P Astragalus membranaceus Roots [77]134 6-O-Palmitoylsucrose P H Astragalus membranaceus Roots [77]
135 61015840-O-Linolenoylsucrose H N Astragalus membranaceusEquisetum hiemale
RootsAerial parts [77 78]
136 6-O-Linoleylsucrose O H Astragalus membranaceus Roots [77]137 6-O-Myristoylsucrose Q H Astragalus membranaceus Roots [77]
138 6-O-[(7Z10Z13Z)-Hexadeca-71013-trienoyl]sucrose H R Equisetum hiemale Aerial parts [78]
139 6-O-[(7Z10Z)-Hexadeca-710-dienoyl]sucrose H S Equisetum hiemale Aerial parts [78]
See Scheme 3
12
3
4
5
6
1998400
2998400
3998400
4998400
5998400
6998400
HO
O
O
R1O
R2O
R8O
R7OOR3
OR4 OR5OR6
O
O
O
18
18
1616
16
14
N linolenoyl
O linoleyl
P palmitoyl
Q myristoyl
O
O
O
R hexadeca-71013-trienoyl
S hexadeca-710-dienoyl
Scheme 3
32 Antidepressant Activity The oligosaccharides obtainedfrom the Morinda genus not only show specific antidepres-sant and antistress activities but also have no suppression orexcitatory effects on central nervous system as well Whatis more they can be taken orally with little toxicity [21]The inulin-type hexasaccharide (IHS) (9) from Morindaofficinalis obviously exhibited cytoprotective activity whichcontributed to the antidepressant effect not only by providingthe PC12 with protection against Cort-induced lesion withIHS 0625 and 125 120583Mbut also by reducing theCort-induced[Ca2+]
119894overloading with IHS 25 and 10 120583M IHS 5 and
10 120583Mupregulated the nerve growth factormRNAexpressionin Cort-induced PC12 cells [22] Polygalatenosides A (181)and B (182) were isolated from the Polygala genus Theysignificantly inhibited the isotope-labeled RTI-55 binding to
norepinephrine transporter protein with the IC50
values of300 and 604 120583M respectively [91]
DISS and tenuifoliside A were isolated from the PolygalaandCynanchum genera Liu et al investigated the antidepres-sant effect of YZ ethanol extract based on the tail suspensiontest (TST) and forced swimming test (FST) which arethe ease-of-use and widely-accepted models for estimatingantidepressant activities in mice The results indicated thatYZ-50 fraction at a dose of 200mgkgwas able to significantlydecrease the immobility time in TST Furthermore YZ-50possessed ability to inhibit corticosterone-induced injury ofhuman neuroblastoma SH-SY5Y cells What is more DISS(123) and tenuifoliside A (44) two major compounds of YZ-50 fraction showed effective protective response to the lesionin SY5Y cells [53] The antidepressant-like effect of DISS at
14 Evidence-Based Complementary and Alternative Medicine
H3CO
HO
HOHO
HO
HO
HO
HOHO
O O
OO O
OO
O
O
O
OO
O
O
OH
OH
OH
OH
OCH3
OCH3
CH2OH
CH2OH
CH2OAc
CH2OAc
H3CO
HOHO
HO
O
O
O
OO
O
O
OH
OH
OH
OCH3
CH2OH
CH2OH
H3CO
H3CO H3CO
HOHO
HO
O
O
O
OO
O
O
OH
OH
OH
OCH3
CH2OH
CH2OAc
CH3O
H
HOHO
HO
HO
HOO O
OO O
OO
OH
OCH3
CH2OHCH2OH
H3CO H3CO
H
CH2CH2 HO
HO
HO
HO
HOO O
OO O
OO
OH
OCH3
CH2OHCH2OAc
H3CO
H
CH2
140 141 142
143 144 145
Figure 4
Table 4 Phenylpropanoid-derived trisaccharide esters
Number Name R1 R2 R3 R4 R5 R6 R7 Source Parts Reference146 Tricornose C K H H H H L H Polygala tricornis Roots [37]147 Tricornose D K H H H H K H Polygala tricornis Roots [37]148 Tricornose E K H H H K L H Polygala tricornis Roots [37]149 Tricornose F K H H H I L H Polygala tricornis Roots [37]See Scheme 4
O
OOO
O
R2O
R4O
R3O
R6O
OH
OH
OH
OH
OR1
OR5CH2OR7
Scheme 4
the doses of 5 10 and 20mgkg was also tested in chronicallymild stressed rats DISS was able to exhibit antidepressantactivity by upregulating the expression of noradrenergic-regulated plasticity genes including cell adhesion moleculeL1 brain-derived neurotrophic factor laminin and cAMP
response element binding protein factor in hippocampus[98] DISS improved the reward reaction by increasingsucrose intake and obviously decreased the levels of serumcortisol adrenocorticotrophic hormone and corticotropin-releasing factor Further DISS played an enhanced role inthe expression of mineralocorticoid receptor together withglucocorticoid receptor mRNA [99]
33 Cytotoxic and Antineoplastic Activities Smilasides AndashFand P smiglasides A and B smilaside P and helonioside Awere isolated from the Smilax Trillium and Paris generaKuo et al obtained smilasides AndashF (51ndash56) and evaluatedtheir cytotoxicity against human tumor cell lines comprisinghuman oral epithelium carcinoma (KB) human cervicalcarcinoma (Hela) human colon tumor (DLD-1) humanbreast adenocarcinoma (MCF-7) human lung carcinoma (A-549) and humanmedulloblastoma (Med) cells byMTTassayExperimental data indicated that all but smilaside C showedcytotoxicity against three to six human tumor cell lines(ED50
= 51ndash130 120583gmL) and smilasides DndashF (ED50
= 27ndash50 120583gmL) displayed strong cytotoxic activities against DLD-1 cells [46]Wang et al reported the antitumor constituents of
Evidence-Based Complementary and Alternative Medicine 15
OH
OH
OH
OH
OH
OHOH
OHOH
OHOH
OH
OHOHOH
OH
OH
OH
OHOH
OH
OH
OHOH
H
H H
HO
O
O
O
O
O
O
O
OO
OO
O
OO
O
HO
HO
HO
OO
O
O
OO
OO
O
OO
O
OO
O
OO
O
O
O
OO
O
O
OO
O
OO
OOOO
HO
HO
HO
HO
HO
HO
HO
HO
HO
HO
HOHO
HO
HO
HO
HO
HO
150 151 152
153 180
AcO
AcO
AcOAcO
OAc
OAc
CH2OH
OHOH
OH OHOH
OHOH
OH
OHOH
CH3O
Figure 5
Table 5 Phenylpropanoid-derived tetrasaccharide esters
Number Name R1 R2 R3 Source Parts Reference154 Tricornose G K H K Polygala tricornis Roots [37]155 Tricornose H K K K Polygala tricornis Roots [37]156 Tricornose I K K L Polygala tricornis Roots [37]157 Tricornose J K I L Polygala tricornis Roots [37]158 Tricornose K K I K Polygala tricornis Roots [37]159 Tricornose L K G K Polygala tricornis Roots [37]See Scheme 5
Smilax riparia including smiglasides A (48) and B (49) 26-di-acetyl-3101584061015840-di-feruloylsucrose (73) helonioside B (40)and smilaside P (65) Only smiglasidesA andB and smilasideP exhibited cytotoxicity against human tumor cell lines withdifferent inhibitory concentrations comparing with cisplatinand paclitaxel as positive controls [47] Helonioside A (39)exhibited higher cytotoxicity with the increase of concentra-tion (01ndash100120583gmL) [45] Tatarisides AndashG (45 119ndash121 46122 47) and diboside A (116) from the Fagopyrum genusexerted cytotoxic activities against different human cell linesand the cytotoxicity of tatariside C was the most remarkablewith the IC
50values ranging from 644 to 749 120583gmL [57]
11015840236-O-Tetra-acetyl-31015840-O-cis-feruloylsucrose (95) fromthe Sparganium plants exhibited extremely weak cyto-toxicity against the growth of mice Lung Adenocarcinoma
795 cell lines with an IC50
value of 116 120583gmL [66] SnS-2oligosaccharides mixture including raffinose (3) stachyose(19) and verbascose (21) from the roots of Scrophularianingpoensis had antitumor activity against the growth ofLewis pulmonary carcinoma cells transplanted into mice[18]
Disaccharide esters and oligosaccharides mixture fromthe Liliaceae Polygonaceae Sparganiaceae and Scrpophular-iaceae families showed effective cytotoxic and antineoplasticactivities The study results indicated that feruloyl and acetylgroups play an important role in mediating cytotoxicitywhich seems to be related to the substitution position offeruloyl groups The feruloyl groups at C-6 or C-11015840 are vitalfor cytotoxicity In addition the increased number of acetylgroups could induce higher tumoricidal activity
16 Evidence-Based Complementary and Alternative Medicine
Table 6 Phenylpropanoid-derived pentasaccharide esters
Number Name R1 R2 R3 R4 R5 R6 Source Parts Reference160 Tenuifoliose A G D I Ac Ac Ac Polygala tenuifolia Roots [38 42]161 Tenuifoliose B G D I H Ac Ac Polygala tenuifolia Roots [42]162 Tenuifoliose C G D I H H H Polygala tenuifolia Roots [42]163 Tenuifoliose F G D U Ac Ac Ac Polygala tenuifolia Roots [42]164 Tenuifoliose G G D U Ac H Ac Polygala tenuifolia Roots [42]165 Tenuifoliose H G D G Ac Ac Ac Polygala tenuifolia Roots [38 42 79]166 Tenuifoliose I G D G Ac H Ac Polygala tenuifolia Roots [42 79]167 Tenuifoliose J G D G H Ac Ac Polygala tenuifolia Roots [42]168 Tenuifoliose K G D G H H Ac Polygala tenuifolia Roots [42]169 Tenuifoliose L G D T Ac Ac Ac Polygala tenuifolia Roots [42 79]170 Tenuifoliose M G D T Ac H Ac Polygala tenuifolia Roots [42]171 Tenuifoliose N I D I Ac Ac Ac Polygala tenuifolia Roots [42]172 Tenuifoliose O I D I H Ac Ac Polygala tenuifolia Roots [42]173 Tenuifoliose P I D I H H Ac Polygala tenuifolia Roots [42]174 Tenuifoliose Q G D T H Ac Ac Polygala tenuifolia Roots [79]175 Tenuifoliose S G D G H H H Polygala tenuifolia Roots [42]176 Tenuifoliose T G D I H H H Polygala tenuifolia Roots [42]177 Tenuifoliose V H D I Ac Ac Ac Polygala tenuifolia Roots [42]178 Tenuifoliose W I D U Ac H Ac Polygala tenuifolia Roots [42]179 Tenuifoliose X I D I H H H Polygala tenuifolia Roots [42]See Scheme 6
O
OO
O
O
O
O
OR1
OH
OH
OH
OHOH
OH
HOHO
HO
HO
OR2
R3O
CH2OH
Scheme 5
34 Anti-Inflammatory Activity Inflammation an importantbasic pathological process is a defense response of biopsywith vascular system to damage stimuli such as pathogensimpaired cells and tissues and physical and chemical factorsHowever if the process of inflammatory response cannot endnormally when cell debris and pathogens were cleared thebiological defence response will become causative factor andbring about many diseases such as diabetes cardiovasculardiseases metabolic syndrome and cancer [100 101]
Tenuifoliside A (44) from the Polygala genus exhibitedstrong anti-inflammatory effect not only by suppressing the
production of NO but also by reducing the production ofiNOS prostaglandin E2 cyclooxygenase-2 and proinflam-matory cytokines through the inhibition of the mitogen-activated protein kinases pathway and NF-120581B pathway [102]The anti-inflammatory activities of quiquesetinerviusides D(108) and E (109) from the Calamus genus were evaluated inRAW 2647 cells Both of them showed significant inhibitoryeffects against the production of LPS-stimulated NOwith theIC50values of 90ndash295120583M [70]Six disaccharide fatty acid esters (132ndash137) were iso-
lated from the Astragalus and Equisetum genera The anti-inflammatory effects of these isolated compounds have alsobeen documented The activation of NF-120581B could upregulatethe expression of proinflammatory cytokines inducible nitricoxide synthase (iNOS) and tumornecrosis factor alpha (TNF-120572) The NF-120581B inhibitory activities of compounds 132ndash137were tested in HepG2 cells stimulated with TNF-120572 All ofthese compounds could significantly restrainTNF-120572-inducedNF-120581B transcriptional activities with the IC
50values of 44ndash
247 120583M Li et al pointed out that olefinic bonds and thelength of the fatty acid moieties contributed to the NF-120581B inhibitory activity Furthermore the inhibition increasedsignificantly with the increase of the number of olefinic bondson the aliphatic moiety [77] These results may provide ascientific basis for the development of new anti-inflammatoryagents
35 Neuroprotective and Cerebral Protective Activities Aswe all know glutamate works as a major excitatory aminoacid neurotransmitter in the mammalian central nervous
Evidence-Based Complementary and Alternative Medicine 17
R6O
R2O
OR3
OR5
OR4
CH2OR1
OCH3
Rham
OO
O
OO O
O
O
O
OO
RhamO
O
OH
OH
OHOH
OH
OHOH
OHHO
HO
HO
T O-rhamnosyl-coumaroyl U O-rhamnosyl-feruloyl
Scheme 6
system and plays a crucial role in several physiological pro-cesses [103] However the accumulation of glutamate inducesdiverse acute and chronic neurodegenerative diseases suchas epilepsy ischemic stroke and Parkinsonrsquos disease aswell as Alzheimerrsquos disease [104] DISS (123) isolated fromthe Polygala genus exhibited neuroprotective effect againstglutamate-induced SH-SY5Y neuronal cell damage The invitro test demonstrated that DISS (06 6 and 60 120583molL)played a critical role in increasing cell viability controllinglactate dehydrogenase and attenuated apoptosis ranging from195 to 258 [105]
Tenuifoliside B (102) from the Polygala genus was ableto significantly shorten the coma time of KCN-inducedanoxia mice at the doses of 3 and 10mgkg and it playedan important role in ameliorating the scopolamine-inducedimpairment of performance in passive avoidance task inrats and enhancing the tremors induced by oxotremorine inmiceThese results together demonstrated that tenuifoliside Bpossessed cognitive improving and cerebral protective effects[56]
36 Antidiabetic Activity Diabetes mellitus a chronic debil-itating metabolic disease is characterized by high bloodglucose content and comprises three types termed type Itype II and gestational diabetes [106] Stachyose (19) extract(a part) from Rehmannia glutinosa obviously exhibited theactivity of downregulating fasting plasma glucose level andpartially keeping from hyperglycemia induced by adrenalineand glucose without obvious dose-dependent effect Otherthan that in vivo tests in rats induced by alloxan revealed
that stachyose extract at the dose of 200mgkg significantlydecreased blood-sugar level [15]
Diboside A lapathosides C and D vanicosides A andB and hydropiperoside were isolated from the FagopyrumPolygonum and Persicaria genera belonging to the Polygo-naceae family Diboside A (116) could potentially inhibit 120572-amylase activity with an IC
50of 269 120583M and thus retard the
starch digestion rate which is helpful for diabetic individualsin controlling blood sugar level [107] Lapathoside D (38)exerted stronger activity of 120572-glucosidase inhibition with anIC50
value of 0113mM than acarbose which was chosen asa positive drug for the treatment of type II diabetes [43]Vanicoside B (111) was reported to have higher 120573-glucosidaseinhibitory activity with an IC
50of 505 120583M than vanicoside A
(110) with an IC50of 599 120583M because of the acetyl moiety of
the latter possibly decreasing inhibitory activity of vanicosideA [71]
Fujimoto et al investigated the inhibitory effects ofmumeoses FndashO (83ndash92) from the Prunus genus on aldosereductase and discovered that caffeoyl groups are crucialfor the inhibitory effect on aldose reductase And thusmumeoses F G H J K L M and N (IC
50= 22ndash77120583M) with
a coumaroyl group and acetyl groups inhibited moderatelyaldose reductase from reducing glucose to sorbitol whichis associated with the chronic complications of diabetes [6364]
37 Elicitors and Regulators Oligosaccharides are quitepropitious for encoding biological information because ofdiverse monosaccharide units and complex molecular struc-tures and they are therefore first described as biological
18 Evidence-Based Complementary and Alternative Medicine
181 H
H
H
H
H
H
H
H
H H
H
H
H
H
H
H
H H
HH
Benzyl
Benzyl
Benzyl
182
183
184 Ac
Ac
Ac
Ac
Ac
Ac
Ac
Ac
Ac
Ac
185
186
187
188
189
R1 R2 R3
R1 R2 R3 R4
OCH3
R3OH2C OR2
OR1
OR1
O
O
O
O O
OOO
O
OO
O
OH
OH
OH OH
OH
O O
O
O
OH
HO
OH
OH OHOH
OH
OH
OHHO
HO
OH
OH
HO
CH2OH
CH2OH
CH2OH
CH2OH
C
R2O
R3O
CH2OR4
CH2CH2 CH2CH2CH2CH2CH3
CH3
CH3
191190 192
193
O
C C
O
OO
OO
OO
OO
O O
O
O
O
O
O
O
OH
OH
OHHO
HO
HOOH
OH
OH
OH
HO
OH
OH
OH
OH
HO
HO
C C
R998400O
R998400
Figure 6
signals in plants [108] Oligosaccharides from the cell wallfragments of plants and fungi are powerful signal moleculessuch as the elicitors of plant defence response and theregulators of plant growth and they are capable of exertingbiological activities at exceedingly low concentrations [109]Heptasaccharide (HS) (15) and octasaccharide (OS) (16) iso-lated from the Paris genus possessed plant growth-regulatory
activities [29 30]The two oligosaccharides significantly pro-moted the proliferation of Paris polyphylla var yunnanensisroots at the doses of 25ndash20mgL The octasaccharide hadthe most obvious effect on the growth of Panax japonicusvar major hairy roots at a dose of 30mgL while the otherhad the most positive effect on saponin accumulation ofPanax japonicus var major hairy roots at a dose of 10mgL
Evidence-Based Complementary and Alternative Medicine 19
[29] Similarly Zhou et al evaluated the stimulating effectsof HS and OS on the root growth and saponin productionof Panax ginseng hairy roots which were induced from theplant roots infected withAgrobacterium rhizogenes strain A4The results showed that there was a maximum effect on thehairy roots growth and saponin accumulation on day 10Compared with control group the root biomass dry weightwas increased by more than 17-fold while the total saponincontent of roots increased by more than 1-fold when thesetwo oligosaccharides were added to the hairy root at a dose of30mgL [30] The above data illustrate that HS and OS couldserve as the plant growth-regulators not only in their originalspecies but also in others
38 Immunopotentiating Activity Macrophages are impor-tant targets of investigations on cytophagy cellular immunityand molecular immunology Therefore they are deemedto play a vital role in host defense comprising phagocy-tosis proteolytic processing pathogenic agent apoptosiscytokines production and foreign antigens presentation[110] The water-extracted oligosaccharides from Panax gin-seng (WGOS) exhibited better immunopotentiating activ-ity by increasing phagocytic function of macrophages andpromoting NO TNF-120572 and reactive oxygen species pro-duction [110] In addition Wan et al have obtained malto-oligosaccharides (17 119899 = 3sim8) and three oligosaccharides (213 14) from the Panax ginseng roots The in vitro bioassaypointed out thatWGOS could serve as efficacious stimulatorsof B and T lymphocytes [28] These studies provided enlight-enment that the mixture of oligosaccharides from Chineseherbalmedicine exhibits significant effect on immune system
39 Others Acetylcholinesterase (AChE) inhibitors showgood therapeutic effects onmyasthenia gravis glaucoma andAlzheimerrsquos disease through reversible enzyme inhibitionso as to increase the accumulation of acetylcholine in thesynapse and then promote and prolong the function ofacetylcholine Vanicoside B (111) showed AChE inhibitoryactivity with an IC
50of 0062mM while hydropiperoside
(42) and lapathosides C (115) and D (38) just exhibited weakenzyme inhibitory activity [43]
Wang et al has explored low molecular mass carbohy-drate polymer from Panax ginseng roots and obtained 30ethanol elution (PGO)which included peptides and oligosac-charides (17 119899 = 0sim5) identified as maltose maltotriosemaltotetraose maltopentaose maltohexaose and maltohep-taose Pharmacological experiments revealed that PGO couldsignificantly enhance the memory in scopolamine-inducedmemory deficit rats [27]
Cistanoside F (129) and kankanose (150) were isolatedfrom the Cistanche Paulownia and Acanthus genera Phar-macological experiments showed that cistanoside F andkankanose significantly exhibited vasorelaxant effects on thenoradrenaline-induced contraction of thoracic aorta fromrats [80]
4 Conclusion
Traditional Chinese medicine from natural kingdom playsan indelible role in the treatment of human diseases andit has aroused the attention of those who have engagedin medicinal pharmaceutical chemistry Therefore scientistshave made great contributions day after day to investigate thevalid chemicals from traditional Chinese medicines In thepast decades about 193 oligosaccharides and their esters havebeen identified from traditional Chinese medicinal plantsOn the one hand only a few oligosaccharides and theirmixtures were investigated and just exhibited antidepres-sant antineoplastic antidiabetic plant growth-regulatoryimmunopotentiating and enhancedmemory activitiesMoreexploratory work is still needed to excavate biological andpharmacological activities of oligosaccharides On the otherhand oligosaccharide esters exhibited multi-advantageousactivities Bioassays have revealed that antioxidant cytotoxicantineoplastic and anti-inflammatory activities are the mostnotable bioactivities Of course to search for the naturalproducts with these activities is a hotpot in the contemporarydrug research Oligosaccharide esters provide a vast treasuretrove for medical researchers After considering the currentstudies it should be taken as future directions to makemore mechanism of action studies and clinical trials tofurther evaluate its potential as new drugs Moreover thestructure-activity relationships discussed in this review willprovide reference information for further exploring theirrelationships and continually discovering the new bioactiveoligosaccharide esters
Conflict of Interests
The authors declare that there is no conflict of interestsregarding the publication of this paper
References
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[2] N Ogwuru and M Adamczeski ldquoBioactive natural productsderived from Polygonum species of plants their structures andmechanisms of actionrdquo Studies in Natural Products Chemistryvol 22 pp 607ndash642 2000
[3] S Kobayashi T Miyase and H Noguchi ldquoPolyphenolic glyco-sides and oligosaccharide multiesters from the roots of Polygaladalmaisianardquo Journal of Natural Products vol 65 no 3 pp 319ndash328 2002
[4] M Takasaki S Kuroki M Kozuka and T Konoshima ldquoNewphenylpropanoid esters of sucrose from Polygonum lapathi-foliumrdquo Journal of Natural Products vol 64 no 10 pp 1305ndash1308 2001
[5] M L Zimmermann and A T Sneden ldquoVanicosides A and Bprotein kinase C inhibitors from Polygonum pensylvanicumrdquoJournal of Natural Products vol 57 no 2 pp 236ndash242 1994
[6] M Takasaki T Konoshima S Kuroki H Tokuda and HNishino ldquoCancer chemopreventive activity of phenylpropanoid
20 Evidence-Based Complementary and Alternative Medicine
esters of sucrose vanicoside B and lapathoside A from Poly-gonum lapathifoliumrdquo Cancer Letters vol 173 no 2 pp 133ndash138 2001
[7] Q Fu T Liang Z Y Li et al ldquoSeparation of carbohydrates usinghydrophilic interaction liquid chromatographyrdquo CarbohydrateResearch vol 379 pp 13ndash17 2013
[8] M F Mrozek D Zhang and D Ben-Amotz ldquoOligosaccharideidentification and mixture quantification using Raman spec-troscopy and chemometric analysisrdquo Carbohydrate Researchvol 339 no 1 pp 141ndash145 2004
[9] G S Armstrong and B Bendiak ldquoHigh-resolution four-dimen-sional carbon-correlated 1H-1H ROESY experiments employ-ing isotags and the filter diagonalization method for effectiveassignment of glycosidic linkages in oligosaccharidesrdquo Journalof Magnetic Resonance vol 181 no 1 pp 79ndash88 2006
[10] G S Armstrong V A Mandelshtam A J Shaka and BBendiak ldquoRapid high-resolution four-dimensional NMR spec-troscopy using the filter diagonalization method and its advan-tages for detailed structural elucidation of oligosaccharidesrdquoJournal of Magnetic Resonance vol 173 no 1 pp 160ndash168 2005
[11] H-M Tseng S Gattolin J Pritchard H J Newbury and DA Barrett ldquoAnalysis of mono- di- and oligosaccharides by CEusing a two-stage derivatization method and LIF detectionrdquoElectrophoresis vol 30 no 8 pp 1399ndash1405 2009
[12] N Li X Li B L Hou and D L Meng ldquoNew disaccharosidefrom Camptosorus sibiricus Ruprrdquo Natural Product Researchvol 22 no 15 pp 1379ndash1383 2008
[13] Z Zhang D Wang Y Zhao H Gao Y-H Hu and J-FHu ldquoFructose-derived carbohydrates from Alisma orientalisrdquoNatural Product Research vol 23 no 11 pp 1013ndash1020 2009
[14] X Yang Y Zhao N He and K D Croft ldquoIsolation char-acterization and immunological effects of 120572-galacto-oligo-saccharides from a new source the herb Lycopus lucidus TurczrdquoJournal of Agricultural and Food Chemistry vol 58 no 14 pp8253ndash8258 2010
[15] R X Zhang Z P Jia L Y Kong et al ldquoStachyose extractfrom Rehmannia glutinosa Libosch to lower plasma glucose innormal and diabetic rats by oral administrationrdquo Pharmazievol 59 no 7 pp 552ndash556 2004
[16] R Zhang Y Zhao Y Sun X Lu and X Yang ldquoIsolationcharacterization and hepatoprotective effects of the raffinosefamily oligosaccharides from Rehmannia glutinosa liboschrdquoJournal of Agricultural and Food Chemistry vol 61 no 32 pp7786ndash7793 2013
[17] H Li F Song Z Zheng Z Liu and S Liu ldquoCharacterization ofsaccharides and phenolic acids in the Chinese herb Tanshen byESI-FT-ICR-MS and HPLCrdquo Journal of Mass Spectrometry vol43 no 11 pp 1545ndash1552 2008
[18] J E Deng J Zhang XM ChenW Ke and G Y Tian ldquoStudieson the physicochemical properties structure and antitumoractivity of an oligosaccharide homologue SnS-2 from the root ofScrophularia ningpoensis Hemslrdquo Chinese Journal of Chemistryvol 22 no 5 pp 492ndash497 2004
[19] S C Chou LM Chuang and S S Lee ldquoHypoglycemic constit-uents of gynura divaricata subsp formosanardquo Natural ProductCommunications vol 7 no 2 pp 221ndash222 2012
[20] F Feng L-L Wang X-P Lai Y-B Li Z-M Cao and Y-J Zhou ldquoStudy on oligosaccharides from Morinda officinalisrdquoJournal of Chinese Medicinal Materials vol 35 no 8 pp 1259ndash1262 2012
[21] Y F Li Z H Gong M Yang Y M Zhao and Z P Luo ldquoInhibi-tion of the oligosaccharides extracted fromMorinda officinalis
a Chinese traditional herbal medicine on the corticosteroneinduced apoptosis in PC12 cellsrdquo Life Sciences vol 72 no 8 pp933ndash942 2003
[22] Y-F Li Y-Q Liu M Yang et al ldquoThe cytoprotective effect ofinulin-type hexasaccharide extracted from Morinda officinalison PC12 cells against the lesion induced by corticosteronerdquo LifeSciences vol 75 no 13 pp 1531ndash1538 2004
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[25] Z J Xu C W Lin and M F Liao ldquoStructure analysis of a newoligosaccharides BROS from Blumea ripariardquo Chinese Journalof Organic Chemistry vol 31 no 11 pp 1811ndash1819 2011
[26] Z J Xu C W Lin and Y Shi ldquoIsolation and structuredetermination of a new oligosaccharide from Blume ripariardquoJournal of Medicinal Plants Research vol 5 no 14 pp 2956ndash2962 2011
[27] Y Wang R Z Jiang G R Li et al ldquoStructural and enhancedmemory activity studies of extracts from Panax ginseng rootrdquoFood Chemistry vol 119 no 3 pp 969ndash973 2010
[28] DWan L Jiao H Yang and S Liu ldquoStructural characterizationand immunological activities of the water-soluble oligosaccha-rides isolated from thePanax ginseng rootsrdquoPlanta vol 235 no6 pp 1289ndash1297 2012
[29] L G Zhou C Z Yang J Q Li S L Wang and J Y WuldquoHeptasaccharide and octasaccharide isolated from Paris pol-yphylla var yunnanensis and their plant growth-regulatoryactivityrdquo Plant Science vol 165 no 3 pp 571ndash575 2003
[30] L G Zhou X D Cao R F Zhang Y L Peng S J Zhao andJ Y Wu ldquoStimulation of saponin production in Panax ginsenghairy roots by two oligosaccharides from Paris polyphylla varyunnanensisrdquo Biotechnology Letters vol 29 no 4 pp 631ndash6342007
[31] M Vanhaecke W van den Ende E Lescrinier and N Dyu-bankova ldquoIsolation and characterization of a pentasaccharidefrom Stellaria mediardquo Journal of Natural Products vol 71 no 11pp 1833ndash1836 2008
[32] J Feng and W Zhao ldquoComplete 1Hand 13C NMR assignmentsof four new oligosaccharides and two new glycosides fromPeriploca forrestiirdquoMagnetic Resonance in Chemistry vol 47 no8 pp 701ndash705 2009
[33] J Q Feng R J Zhang Y Zhou et al ldquoImmunosuppressive preg-nane glycosides from Periploca sepium and Periploca forrestiirdquoPhytochemistry vol 69 no 15 pp 2716ndash2723 2008
[34] X H Long R Xu Y H Zhang X H Tan andQ Y Sun ldquoA newoligosaccharide from Periploca calophyllardquo Zhongguo ZhongyaoZazhi vol 37 no 2 pp 226ndash229 2012
[35] L Wang Z-Q Yin Y Wang X-Q Zhang Y-L Li and W-CYe ldquoPerisesaccharides A-E new oligosaccharides from the rootbarks ofPeriploca sepiumrdquoPlantaMedica vol 76 no 9 pp 909ndash915 2010
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Evidence-Based Complementary and Alternative Medicine 21
[38] H H Tu P Liu L Mu et al ldquoStudy on antidepressant com-ponents of sucrose ester from Polygala tenuifoliardquo ZhongguoZhongyao Zazhi vol 33 no 11 pp 1278ndash1280 2008
[39] G M She Y Y Ba Y Liu H Lv W Wang and R B ShildquoAbsorbable phenylpropenoyl sucroses from Polygala tenuifo-liardquoMolecules vol 16 no 7 pp 5507ndash5513 2011
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[42] Y Ling Z Li M Chen Z Sun M Fan and C HuangldquoAnalysis and detection of the chemical constituents of RadixPolygalae and their metabolites in rats after oral administrationby ultra high-performance liquid chromatography coupledwith electrospray ionization quadrupole time-of-flight tandemmass spectrometryrdquo Journal of Pharmaceutical and BiomedicalAnalysis vol 85 pp 1ndash13 2013
[43] P Fan L Terrier A-E Hay A Marston and K HostettmannldquoAntioxidant and enzyme inhibition activities and chemicalprofiles ofPolygonum sachalinensis FSchmidt exMaxim (Polyg-onaceae)rdquo Fitoterapia vol 81 no 2 pp 124ndash131 2010
[44] L J Zhang C C Liao H C Huang Y C Shen L M Yangand Y H Kuo ldquoAntioxidant phenylpropanoid glycosides fromSmilax bracteatardquo Phytochemistry vol 69 no 6 pp 1398ndash14042008
[45] L L Yan W Y Gao Y J Zhang and Y Wang ldquoA new phenyl-propanoid glycosides from Paris polyphylla var yunnanensisrdquoFitoterapia vol 79 no 4 pp 306ndash307 2008
[46] Y H Kuo Y W Hsu C C Liaw J K Lee H C Huang andL M Y Kuo ldquoCytotoxic phenylpropanoid glycosides from thestems of Smilax chinardquo Journal of Natural Products vol 68 no10 pp 1475ndash1478 2005
[47] W-X Wang T-X Li H Ma J-F Zhang and A-Q JialdquoTumoral cytotoxic and antioxidative phenylpropanoid glyco-sides in Smilax riparia A DCrdquo Journal of Ethnopharmacologyvol 149 no 2 pp 527ndash532 2013
[48] N X Nhiem P vanKiem C vanMinh et al ldquoPhenylpropanoidglycosides fromHeterosmilax erythrantha and their antioxidantactivityrdquo Archives of Pharmacal Research vol 32 no 10 pp1373ndash1377 2009
[49] Y Wang W Y Gao T J Zhang and Y Q Guo ldquoA novelphenylpropanoid glycosides and a new derivation of phenolicglycoside from Paris Polyphylla var yunnanensisrdquo ChineseChemical Letters vol 18 no 5 pp 548ndash550 2007
[50] J-Y Zhang Y-Z Wang Y-L Zhao et al ldquoPhytochemicals andbioactivities of Paris speciesrdquo Journal of Asian Natural ProductsResearch vol 13 no 7 pp 670ndash681 2011
[51] N H N Hashim F Abas K Shaari and N H Lajis ldquoLC-DAD-ESIMSMS characterization of antioxidant and anti-cholinesterase constituents present in the active fraction fromPersicaria hydropiperrdquo LWT Food Science and Technology vol46 no 2 pp 468ndash476 2012
[52] PH FanA EHayAMarstonHX Lou andKHostettmannldquoChemical variability of the invasive neophytes Polygonumcuspidatum Sieb and Zucc and Polygonum sachalinensis FSchmidt ex Maximrdquo Biochemical Systematics and Ecology vol37 no 1 pp 24ndash34 2009
[53] P Liu Y Hu D H Guo et al ldquoPotential antidepressantproperties of Radix Polygalae (Yuan Zhi)rdquo Phytomedicine vol17 no 10 pp 794ndash799 2010
[54] J F Wu S B Chen S L Chen and P F Tu ldquoThe chemical con-stituents of Polygala hongkongensisHemslrdquoActa PharmaceuticaSinica vol 42 no 7 pp 757ndash761 2007
[55] Y Song Y Jiang D Bi X Tian L Liang and P Tu ldquoChemicalconstituents from n-butanol extract of aerial part of Polygalasibiricardquo Zhongguo Zhongyao Zazhi vol 37 no 4 pp 471ndash4742012
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[65] L-B Dong J He X-Y Li et al ldquoChemical constituents fromthe aerial parts of Musella lasiocarpardquo Natural Products andBioprospecting vol 1 no 1 pp 41ndash47 2011
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[68] B Chen N L Wang J H Huang and X S Yao ldquoIridoidand phenylpropanoid glycosides from Scrophularia ningpoensis
22 Evidence-Based Complementary and Alternative Medicine
Hemslrdquo Asian Journal of Traditional Medicines vol 2 no 3 pp119ndash123 2007
[69] H Chen Y Z Zhou L Qiao et al ldquoTwo new compounds fromCynanchum amplexicaulerdquo Journal of Asian Natural ProductsResearch vol 10 no 3 pp 248ndash251 2008
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[71] Y Kawai H Kumagai H Kurihara K Yamazaki R Sawanoand N Inoue ldquo120573-Glucosidase inhibitory activities of phenyl-propanoid glycosides vanicoside A and B from Polygonumsachalinense rhizomerdquo Fitoterapia vol 77 no 6 pp 456ndash4592006
[72] P V Kiem N X Nhiem N X Cuong et al ldquoNew phenyl-propanoid esters of sucrose from Polygonum hydropiper andtheir antioxidant activityrdquo Archives of Pharmacal Research vol31 no 11 pp 1477ndash1482 2008
[73] K J Wang Y J Zhang and C R Yang ldquoAntioxidant phenolicconstituents from Fagopyrum dibotrysrdquo Journal of Ethnophar-macology vol 99 no 2 pp 259ndash264 2005
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[75] Q Ren C S Wu and J L Zhang ldquoUse of on-line stop-flowheart-cutting two-dimensional high performance liquid chro-matography for simultaneous determination of 12 major con-stituents in tartary buckwheat (Fagopyrum tataricum Gaertn)rdquoJournal of Chromatography A vol 1304 pp 257ndash262 2013
[76] Q Ren C S Wu Y Ren and J L Zhang ldquoCharacterizationand identification of the chemical constituents from tartarybuckwheat (Fagopyrum tataricumGaertn) by high performanceliquid chromatographyphotodiode array detectorlinear iontrap FTICR hybrid mass spectrometryrdquo Food Chemistry vol136 no 3-4 pp 1377ndash1389 2013
[77] W Li Y N Sun X T Yan et al ldquoNF-120581B inhibitory activityof sucrose fatty acid esters and related constituents fromAstragalus membranaceusrdquo Journal of Agricultural and FoodChemistry vol 61 no 29 pp 7081ndash7088 2013
[78] J T Cheng J He Y Li et al ldquoThree new sucrose fatty acid estersfrom Equisetum hiemale LrdquoHelvetica Chimica Acta vol 95 no7 pp 1158ndash1163 2012
[79] Y Jiang and P-F Tu ldquoTenuifoliose Q a new oligosaccharideester from the root of Polygala tenuifoliaWilldrdquo Journal of AsianNatural Products Research vol 5 no 4 pp 279ndash283 2003
[80] M Yoshikawa H Matsuda T Morikawa H H Xie S Naka-mura and O Muraoka ldquoPhenylethanoid oligoglycosides andacylated oligosugars with vasorelaxant activity from Cistanchetubulosardquo Bioorganic ampMedicinal Chemistry vol 14 no 22 pp7468ndash7475 2006
[81] P-F Tu H-M Shi Z-H Song Y Jiang and Y-Y ZhaoldquoChemical constituents of Cistanche sinensisrdquo Journal of AsianNatural Products Research vol 9 no 1 pp 79ndash84 2007
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[83] J Wu S Zhang Q Xiao et al ldquoPhenylethanoid and aliphaticalcohol glycosides from Acanthus ilicifoliusrdquo Phytochemistryvol 63 no 4 pp 491ndash495 2003
[84] Y Jiang and P-F Tu ldquoAnalysis of chemical constituents inCistanche speciesrdquo Journal of Chromatography A vol 1216 no11 pp 1970ndash1979 2009
[85] H Otsuka H Kuwabara and H Hoshiyama ldquoIdentification ofsucrose diesters of aryldihydronaphthalene-type lignans fromTrigonotis peduncularisand the nature of their fluorescencerdquoJournal of Natural Products vol 71 no 7 pp 1178ndash1181 2008
[86] M-R Suo J-S Yang and Q-H Liu ldquoLignan oligosaccharideesters from Eritrichium rupestrerdquo Journal of Natural Productsvol 69 no 4 pp 682ndash684 2006
[87] P-F Tu Z-H Song H-M Shi Y Jiang and Y-Y ZhaoldquoArylethyl (=phenylethanoid) glycosides and oligosaccharidefrom the stem of Cistanche tubulosardquo Helvetica Chimica Actavol 89 no 5 pp 927ndash935 2006
[88] M-H Shyr T-H Tsai and L-C Lin ldquoRossicasins A Band rosicaside F three new phenylpropanoid glycosides fromBoschniakia rossicardquoChemical and Pharmaceutical Bulletin vol54 no 2 pp 252ndash254 2006
[89] R FangNCVeitchGCKiteM J RHowes EA Porter andM S J Simmonds ldquoGlycosylated constituents of Iris fulvaandIris brevicaulisrdquoChemical amp Pharmaceutical Bulletin vol 59 no1 pp 124ndash128 2011
[90] J Fu L Zuo J Yang R Chen and D Zhang ldquoOligosaccharidepolyester and triterpenoid saponins from the roots of Polygalajaponicardquo Phytochemistry vol 69 no 7 pp 1617ndash1624 2008
[91] M-C Cheng C-Y Li H-C Ko F-N Ko Y-L Lin andT-S Wu ldquoAntidepressant principles of the roots of polygalatenuifoliardquo Journal of Natural Products vol 69 no 9 pp 1305ndash1309 2006
[92] H T Chang and P F Tu ldquoNew oligosaccharide esters andxanthone C-glucosides from Polygala telephioidesrdquo HelveticaChimica Acta vol 90 no 5 pp 944ndash950 2007
[93] J Li L Feng J Dai R Wang and T Nohara ldquoChemical con-stituents from Polygala telephioidesrdquo China Journal of ChineseMateria Medica vol 34 no 4 pp 402ndash405 2009
[94] W-P Yin T-Z Zhao and H-Y Zhang ldquoA novel oligosaccha-ride ester from Syringa pubescensrdquo Journal of Asian NaturalProducts Research vol 10 no 1 pp 95ndash100 2008
[95] M Valko D Leibfritz J Moncol M T D Cronin M Mazurand J Telser ldquoFree radicals and antioxidants in normal physio-logical functions and human diseaserdquoThe International Journalof Biochemistry amp Cell Biology vol 39 no 1 pp 44ndash84 2007
[96] D Krishnaiah R Sarbatly and R Nithyanandam ldquoA review ofthe antioxidant potential of medicinal plant speciesrdquo Food andBioproducts Processing vol 89 no 3 pp 217ndash233 2011
[97] P Liu Y Hu D-H Guo et al ldquoAntioxidant activity ofoligosaccharide ester extracted from Polygala tenuifolia roots insenescence-accelerated micerdquo Pharmaceutical Biology vol 48no 7 pp 828ndash833 2010
[98] Y Hu H-B Liao G Dai-Hong P Liu Y-Y Wang and KRahman ldquoAntidepressant-like effects of 361015840-disinapoyl sucroseon hippocampal neuronal plasticity and neurotrophic signalpathway in chronically mild stressed ratsrdquo NeurochemistryInternational vol 56 no 3 pp 461ndash465 2010
[99] Y Hu H B O Liao P Liu D-H Guo and K RahmanldquoA bioactive compound from Polygala tenuifolia regulatesefficiency of chronic stress on hypothalamic-pituitary-adrenalaxisrdquo Pharmazie vol 64 no 9 pp 605ndash608 2009
[100] A Jungbauer and SMedjakovic ldquoAnti-inflammatory propertiesof culinary herbs and spices that ameliorate the effects ofmetabolic syndromerdquoMaturitas vol 71 no 3 pp 227ndash239 2012
Evidence-Based Complementary and Alternative Medicine 23
[101] Q Xu Y Wang S Guo Z Shen and L Yang ldquoAnti-inflammatory and analgesic activity of aqueous extract of Flospopulirdquo Journal of Ethnopharmacology vol 152 no 3 pp 540ndash545 2014
[102] K S Kim D S Lee G S Bae et al ldquoThe inhibition of JNKMAPK and NF-120581B signaling by tenuifoliside A isolated fromPolygala tenuifolia in lipopolysaccharide-induced macrophagesis associated with its anti-inflammatory effectrdquo European Jour-nal of Pharmacology vol 721 no 1ndash3 pp 267ndash276 2013
[103] J-G Lee J-M Yon C Lin A Y Jung K Y Jung and S-YNamldquoCombined treatment with capsaicin and resveratrol enhancesneuroprotection against glutamate-induced toxicity in mousecerebral cortical neuronsrdquo Food and Chemical Toxicology vol50 no 11 pp 3877ndash3885 2012
[104] M L Jin S Y Park Y H Kim J-I Oh S J Lee andG Park ldquoThe neuroprotective effects of cordycepin inhibitglutamate-induced oxidative andER stress-associated apoptosisin hippocampal HT22 cellsrdquo NeuroToxicology vol 41 pp 102ndash111 2014
[105] P Liu Y Hu J Li et al ldquoProtection of SH-SY5Y neuronal cellsfrom glutamate-induced apoptosis by 36rsquo-disinapoyl sucrosea bioactive compound isolated from radix polygalardquo Journal ofBiomedicine and Biotechnology vol 2012 Article ID 728342 5pages 2012
[106] P-B Li W-L Lin Y-G Wang W Peng X-Y Cai and W-WSu ldquoAntidiabetic activities of oligosaccharides of Ophiopogonisjaponicus in experimental type 2 diabetic ratsrdquo InternationalJournal of Biological Macromolecules vol 51 no 5 pp 749ndash7552012
[107] T Liu Y M Yip L Song et al ldquoInhibiting enzymatic starchdigestion by the phenolic compound diboside A a mechanisticand in silico studyrdquo Food Research International vol 54 no 1pp 595ndash600 2013
[108] F Cote andMGHahn ldquoOligosaccharins structures and signaltransductionrdquo Plant Molecular Biology vol 26 no 5 pp 1379ndash1411 1994
[109] RACreelman and J EMullet ldquoOligosaccharins brassinolidesand jasmonates nontraditional regulators of plant growthdevelopment and gene expressionrdquo Plant Cell vol 9 no 7 pp1211ndash1223 1997
[110] L Jiao D Wan X Zhang B Li H Zhao and S LiuldquoCharacterization and immunostimulating effects on murineperitoneal macrophages of oligosaccharide isolated from Panaxginseng CAMeyerrdquo Journal of Ethnopharmacology vol 144 no3 pp 490ndash496 2012
Submit your manuscripts athttpwwwhindawicom
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Evidence-Based Complementary and Alternative Medicine
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14 Evidence-Based Complementary and Alternative Medicine
H3CO
HO
HOHO
HO
HO
HO
HOHO
O O
OO O
OO
O
O
O
OO
O
O
OH
OH
OH
OH
OCH3
OCH3
CH2OH
CH2OH
CH2OAc
CH2OAc
H3CO
HOHO
HO
O
O
O
OO
O
O
OH
OH
OH
OCH3
CH2OH
CH2OH
H3CO
H3CO H3CO
HOHO
HO
O
O
O
OO
O
O
OH
OH
OH
OCH3
CH2OH
CH2OAc
CH3O
H
HOHO
HO
HO
HOO O
OO O
OO
OH
OCH3
CH2OHCH2OH
H3CO H3CO
H
CH2CH2 HO
HO
HO
HO
HOO O
OO O
OO
OH
OCH3
CH2OHCH2OAc
H3CO
H
CH2
140 141 142
143 144 145
Figure 4
Table 4 Phenylpropanoid-derived trisaccharide esters
Number Name R1 R2 R3 R4 R5 R6 R7 Source Parts Reference146 Tricornose C K H H H H L H Polygala tricornis Roots [37]147 Tricornose D K H H H H K H Polygala tricornis Roots [37]148 Tricornose E K H H H K L H Polygala tricornis Roots [37]149 Tricornose F K H H H I L H Polygala tricornis Roots [37]See Scheme 4
O
OOO
O
R2O
R4O
R3O
R6O
OH
OH
OH
OH
OR1
OR5CH2OR7
Scheme 4
the doses of 5 10 and 20mgkg was also tested in chronicallymild stressed rats DISS was able to exhibit antidepressantactivity by upregulating the expression of noradrenergic-regulated plasticity genes including cell adhesion moleculeL1 brain-derived neurotrophic factor laminin and cAMP
response element binding protein factor in hippocampus[98] DISS improved the reward reaction by increasingsucrose intake and obviously decreased the levels of serumcortisol adrenocorticotrophic hormone and corticotropin-releasing factor Further DISS played an enhanced role inthe expression of mineralocorticoid receptor together withglucocorticoid receptor mRNA [99]
33 Cytotoxic and Antineoplastic Activities Smilasides AndashFand P smiglasides A and B smilaside P and helonioside Awere isolated from the Smilax Trillium and Paris generaKuo et al obtained smilasides AndashF (51ndash56) and evaluatedtheir cytotoxicity against human tumor cell lines comprisinghuman oral epithelium carcinoma (KB) human cervicalcarcinoma (Hela) human colon tumor (DLD-1) humanbreast adenocarcinoma (MCF-7) human lung carcinoma (A-549) and humanmedulloblastoma (Med) cells byMTTassayExperimental data indicated that all but smilaside C showedcytotoxicity against three to six human tumor cell lines(ED50
= 51ndash130 120583gmL) and smilasides DndashF (ED50
= 27ndash50 120583gmL) displayed strong cytotoxic activities against DLD-1 cells [46]Wang et al reported the antitumor constituents of
Evidence-Based Complementary and Alternative Medicine 15
OH
OH
OH
OH
OH
OHOH
OHOH
OHOH
OH
OHOHOH
OH
OH
OH
OHOH
OH
OH
OHOH
H
H H
HO
O
O
O
O
O
O
O
OO
OO
O
OO
O
HO
HO
HO
OO
O
O
OO
OO
O
OO
O
OO
O
OO
O
O
O
OO
O
O
OO
O
OO
OOOO
HO
HO
HO
HO
HO
HO
HO
HO
HO
HO
HOHO
HO
HO
HO
HO
HO
150 151 152
153 180
AcO
AcO
AcOAcO
OAc
OAc
CH2OH
OHOH
OH OHOH
OHOH
OH
OHOH
CH3O
Figure 5
Table 5 Phenylpropanoid-derived tetrasaccharide esters
Number Name R1 R2 R3 Source Parts Reference154 Tricornose G K H K Polygala tricornis Roots [37]155 Tricornose H K K K Polygala tricornis Roots [37]156 Tricornose I K K L Polygala tricornis Roots [37]157 Tricornose J K I L Polygala tricornis Roots [37]158 Tricornose K K I K Polygala tricornis Roots [37]159 Tricornose L K G K Polygala tricornis Roots [37]See Scheme 5
Smilax riparia including smiglasides A (48) and B (49) 26-di-acetyl-3101584061015840-di-feruloylsucrose (73) helonioside B (40)and smilaside P (65) Only smiglasidesA andB and smilasideP exhibited cytotoxicity against human tumor cell lines withdifferent inhibitory concentrations comparing with cisplatinand paclitaxel as positive controls [47] Helonioside A (39)exhibited higher cytotoxicity with the increase of concentra-tion (01ndash100120583gmL) [45] Tatarisides AndashG (45 119ndash121 46122 47) and diboside A (116) from the Fagopyrum genusexerted cytotoxic activities against different human cell linesand the cytotoxicity of tatariside C was the most remarkablewith the IC
50values ranging from 644 to 749 120583gmL [57]
11015840236-O-Tetra-acetyl-31015840-O-cis-feruloylsucrose (95) fromthe Sparganium plants exhibited extremely weak cyto-toxicity against the growth of mice Lung Adenocarcinoma
795 cell lines with an IC50
value of 116 120583gmL [66] SnS-2oligosaccharides mixture including raffinose (3) stachyose(19) and verbascose (21) from the roots of Scrophularianingpoensis had antitumor activity against the growth ofLewis pulmonary carcinoma cells transplanted into mice[18]
Disaccharide esters and oligosaccharides mixture fromthe Liliaceae Polygonaceae Sparganiaceae and Scrpophular-iaceae families showed effective cytotoxic and antineoplasticactivities The study results indicated that feruloyl and acetylgroups play an important role in mediating cytotoxicitywhich seems to be related to the substitution position offeruloyl groups The feruloyl groups at C-6 or C-11015840 are vitalfor cytotoxicity In addition the increased number of acetylgroups could induce higher tumoricidal activity
16 Evidence-Based Complementary and Alternative Medicine
Table 6 Phenylpropanoid-derived pentasaccharide esters
Number Name R1 R2 R3 R4 R5 R6 Source Parts Reference160 Tenuifoliose A G D I Ac Ac Ac Polygala tenuifolia Roots [38 42]161 Tenuifoliose B G D I H Ac Ac Polygala tenuifolia Roots [42]162 Tenuifoliose C G D I H H H Polygala tenuifolia Roots [42]163 Tenuifoliose F G D U Ac Ac Ac Polygala tenuifolia Roots [42]164 Tenuifoliose G G D U Ac H Ac Polygala tenuifolia Roots [42]165 Tenuifoliose H G D G Ac Ac Ac Polygala tenuifolia Roots [38 42 79]166 Tenuifoliose I G D G Ac H Ac Polygala tenuifolia Roots [42 79]167 Tenuifoliose J G D G H Ac Ac Polygala tenuifolia Roots [42]168 Tenuifoliose K G D G H H Ac Polygala tenuifolia Roots [42]169 Tenuifoliose L G D T Ac Ac Ac Polygala tenuifolia Roots [42 79]170 Tenuifoliose M G D T Ac H Ac Polygala tenuifolia Roots [42]171 Tenuifoliose N I D I Ac Ac Ac Polygala tenuifolia Roots [42]172 Tenuifoliose O I D I H Ac Ac Polygala tenuifolia Roots [42]173 Tenuifoliose P I D I H H Ac Polygala tenuifolia Roots [42]174 Tenuifoliose Q G D T H Ac Ac Polygala tenuifolia Roots [79]175 Tenuifoliose S G D G H H H Polygala tenuifolia Roots [42]176 Tenuifoliose T G D I H H H Polygala tenuifolia Roots [42]177 Tenuifoliose V H D I Ac Ac Ac Polygala tenuifolia Roots [42]178 Tenuifoliose W I D U Ac H Ac Polygala tenuifolia Roots [42]179 Tenuifoliose X I D I H H H Polygala tenuifolia Roots [42]See Scheme 6
O
OO
O
O
O
O
OR1
OH
OH
OH
OHOH
OH
HOHO
HO
HO
OR2
R3O
CH2OH
Scheme 5
34 Anti-Inflammatory Activity Inflammation an importantbasic pathological process is a defense response of biopsywith vascular system to damage stimuli such as pathogensimpaired cells and tissues and physical and chemical factorsHowever if the process of inflammatory response cannot endnormally when cell debris and pathogens were cleared thebiological defence response will become causative factor andbring about many diseases such as diabetes cardiovasculardiseases metabolic syndrome and cancer [100 101]
Tenuifoliside A (44) from the Polygala genus exhibitedstrong anti-inflammatory effect not only by suppressing the
production of NO but also by reducing the production ofiNOS prostaglandin E2 cyclooxygenase-2 and proinflam-matory cytokines through the inhibition of the mitogen-activated protein kinases pathway and NF-120581B pathway [102]The anti-inflammatory activities of quiquesetinerviusides D(108) and E (109) from the Calamus genus were evaluated inRAW 2647 cells Both of them showed significant inhibitoryeffects against the production of LPS-stimulated NOwith theIC50values of 90ndash295120583M [70]Six disaccharide fatty acid esters (132ndash137) were iso-
lated from the Astragalus and Equisetum genera The anti-inflammatory effects of these isolated compounds have alsobeen documented The activation of NF-120581B could upregulatethe expression of proinflammatory cytokines inducible nitricoxide synthase (iNOS) and tumornecrosis factor alpha (TNF-120572) The NF-120581B inhibitory activities of compounds 132ndash137were tested in HepG2 cells stimulated with TNF-120572 All ofthese compounds could significantly restrainTNF-120572-inducedNF-120581B transcriptional activities with the IC
50values of 44ndash
247 120583M Li et al pointed out that olefinic bonds and thelength of the fatty acid moieties contributed to the NF-120581B inhibitory activity Furthermore the inhibition increasedsignificantly with the increase of the number of olefinic bondson the aliphatic moiety [77] These results may provide ascientific basis for the development of new anti-inflammatoryagents
35 Neuroprotective and Cerebral Protective Activities Aswe all know glutamate works as a major excitatory aminoacid neurotransmitter in the mammalian central nervous
Evidence-Based Complementary and Alternative Medicine 17
R6O
R2O
OR3
OR5
OR4
CH2OR1
OCH3
Rham
OO
O
OO O
O
O
O
OO
RhamO
O
OH
OH
OHOH
OH
OHOH
OHHO
HO
HO
T O-rhamnosyl-coumaroyl U O-rhamnosyl-feruloyl
Scheme 6
system and plays a crucial role in several physiological pro-cesses [103] However the accumulation of glutamate inducesdiverse acute and chronic neurodegenerative diseases suchas epilepsy ischemic stroke and Parkinsonrsquos disease aswell as Alzheimerrsquos disease [104] DISS (123) isolated fromthe Polygala genus exhibited neuroprotective effect againstglutamate-induced SH-SY5Y neuronal cell damage The invitro test demonstrated that DISS (06 6 and 60 120583molL)played a critical role in increasing cell viability controllinglactate dehydrogenase and attenuated apoptosis ranging from195 to 258 [105]
Tenuifoliside B (102) from the Polygala genus was ableto significantly shorten the coma time of KCN-inducedanoxia mice at the doses of 3 and 10mgkg and it playedan important role in ameliorating the scopolamine-inducedimpairment of performance in passive avoidance task inrats and enhancing the tremors induced by oxotremorine inmiceThese results together demonstrated that tenuifoliside Bpossessed cognitive improving and cerebral protective effects[56]
36 Antidiabetic Activity Diabetes mellitus a chronic debil-itating metabolic disease is characterized by high bloodglucose content and comprises three types termed type Itype II and gestational diabetes [106] Stachyose (19) extract(a part) from Rehmannia glutinosa obviously exhibited theactivity of downregulating fasting plasma glucose level andpartially keeping from hyperglycemia induced by adrenalineand glucose without obvious dose-dependent effect Otherthan that in vivo tests in rats induced by alloxan revealed
that stachyose extract at the dose of 200mgkg significantlydecreased blood-sugar level [15]
Diboside A lapathosides C and D vanicosides A andB and hydropiperoside were isolated from the FagopyrumPolygonum and Persicaria genera belonging to the Polygo-naceae family Diboside A (116) could potentially inhibit 120572-amylase activity with an IC
50of 269 120583M and thus retard the
starch digestion rate which is helpful for diabetic individualsin controlling blood sugar level [107] Lapathoside D (38)exerted stronger activity of 120572-glucosidase inhibition with anIC50
value of 0113mM than acarbose which was chosen asa positive drug for the treatment of type II diabetes [43]Vanicoside B (111) was reported to have higher 120573-glucosidaseinhibitory activity with an IC
50of 505 120583M than vanicoside A
(110) with an IC50of 599 120583M because of the acetyl moiety of
the latter possibly decreasing inhibitory activity of vanicosideA [71]
Fujimoto et al investigated the inhibitory effects ofmumeoses FndashO (83ndash92) from the Prunus genus on aldosereductase and discovered that caffeoyl groups are crucialfor the inhibitory effect on aldose reductase And thusmumeoses F G H J K L M and N (IC
50= 22ndash77120583M) with
a coumaroyl group and acetyl groups inhibited moderatelyaldose reductase from reducing glucose to sorbitol whichis associated with the chronic complications of diabetes [6364]
37 Elicitors and Regulators Oligosaccharides are quitepropitious for encoding biological information because ofdiverse monosaccharide units and complex molecular struc-tures and they are therefore first described as biological
18 Evidence-Based Complementary and Alternative Medicine
181 H
H
H
H
H
H
H
H
H H
H
H
H
H
H
H
H H
HH
Benzyl
Benzyl
Benzyl
182
183
184 Ac
Ac
Ac
Ac
Ac
Ac
Ac
Ac
Ac
Ac
185
186
187
188
189
R1 R2 R3
R1 R2 R3 R4
OCH3
R3OH2C OR2
OR1
OR1
O
O
O
O O
OOO
O
OO
O
OH
OH
OH OH
OH
O O
O
O
OH
HO
OH
OH OHOH
OH
OH
OHHO
HO
OH
OH
HO
CH2OH
CH2OH
CH2OH
CH2OH
C
R2O
R3O
CH2OR4
CH2CH2 CH2CH2CH2CH2CH3
CH3
CH3
191190 192
193
O
C C
O
OO
OO
OO
OO
O O
O
O
O
O
O
O
OH
OH
OHHO
HO
HOOH
OH
OH
OH
HO
OH
OH
OH
OH
HO
HO
C C
R998400O
R998400
Figure 6
signals in plants [108] Oligosaccharides from the cell wallfragments of plants and fungi are powerful signal moleculessuch as the elicitors of plant defence response and theregulators of plant growth and they are capable of exertingbiological activities at exceedingly low concentrations [109]Heptasaccharide (HS) (15) and octasaccharide (OS) (16) iso-lated from the Paris genus possessed plant growth-regulatory
activities [29 30]The two oligosaccharides significantly pro-moted the proliferation of Paris polyphylla var yunnanensisroots at the doses of 25ndash20mgL The octasaccharide hadthe most obvious effect on the growth of Panax japonicusvar major hairy roots at a dose of 30mgL while the otherhad the most positive effect on saponin accumulation ofPanax japonicus var major hairy roots at a dose of 10mgL
Evidence-Based Complementary and Alternative Medicine 19
[29] Similarly Zhou et al evaluated the stimulating effectsof HS and OS on the root growth and saponin productionof Panax ginseng hairy roots which were induced from theplant roots infected withAgrobacterium rhizogenes strain A4The results showed that there was a maximum effect on thehairy roots growth and saponin accumulation on day 10Compared with control group the root biomass dry weightwas increased by more than 17-fold while the total saponincontent of roots increased by more than 1-fold when thesetwo oligosaccharides were added to the hairy root at a dose of30mgL [30] The above data illustrate that HS and OS couldserve as the plant growth-regulators not only in their originalspecies but also in others
38 Immunopotentiating Activity Macrophages are impor-tant targets of investigations on cytophagy cellular immunityand molecular immunology Therefore they are deemedto play a vital role in host defense comprising phagocy-tosis proteolytic processing pathogenic agent apoptosiscytokines production and foreign antigens presentation[110] The water-extracted oligosaccharides from Panax gin-seng (WGOS) exhibited better immunopotentiating activ-ity by increasing phagocytic function of macrophages andpromoting NO TNF-120572 and reactive oxygen species pro-duction [110] In addition Wan et al have obtained malto-oligosaccharides (17 119899 = 3sim8) and three oligosaccharides (213 14) from the Panax ginseng roots The in vitro bioassaypointed out thatWGOS could serve as efficacious stimulatorsof B and T lymphocytes [28] These studies provided enlight-enment that the mixture of oligosaccharides from Chineseherbalmedicine exhibits significant effect on immune system
39 Others Acetylcholinesterase (AChE) inhibitors showgood therapeutic effects onmyasthenia gravis glaucoma andAlzheimerrsquos disease through reversible enzyme inhibitionso as to increase the accumulation of acetylcholine in thesynapse and then promote and prolong the function ofacetylcholine Vanicoside B (111) showed AChE inhibitoryactivity with an IC
50of 0062mM while hydropiperoside
(42) and lapathosides C (115) and D (38) just exhibited weakenzyme inhibitory activity [43]
Wang et al has explored low molecular mass carbohy-drate polymer from Panax ginseng roots and obtained 30ethanol elution (PGO)which included peptides and oligosac-charides (17 119899 = 0sim5) identified as maltose maltotriosemaltotetraose maltopentaose maltohexaose and maltohep-taose Pharmacological experiments revealed that PGO couldsignificantly enhance the memory in scopolamine-inducedmemory deficit rats [27]
Cistanoside F (129) and kankanose (150) were isolatedfrom the Cistanche Paulownia and Acanthus genera Phar-macological experiments showed that cistanoside F andkankanose significantly exhibited vasorelaxant effects on thenoradrenaline-induced contraction of thoracic aorta fromrats [80]
4 Conclusion
Traditional Chinese medicine from natural kingdom playsan indelible role in the treatment of human diseases andit has aroused the attention of those who have engagedin medicinal pharmaceutical chemistry Therefore scientistshave made great contributions day after day to investigate thevalid chemicals from traditional Chinese medicines In thepast decades about 193 oligosaccharides and their esters havebeen identified from traditional Chinese medicinal plantsOn the one hand only a few oligosaccharides and theirmixtures were investigated and just exhibited antidepres-sant antineoplastic antidiabetic plant growth-regulatoryimmunopotentiating and enhancedmemory activitiesMoreexploratory work is still needed to excavate biological andpharmacological activities of oligosaccharides On the otherhand oligosaccharide esters exhibited multi-advantageousactivities Bioassays have revealed that antioxidant cytotoxicantineoplastic and anti-inflammatory activities are the mostnotable bioactivities Of course to search for the naturalproducts with these activities is a hotpot in the contemporarydrug research Oligosaccharide esters provide a vast treasuretrove for medical researchers After considering the currentstudies it should be taken as future directions to makemore mechanism of action studies and clinical trials tofurther evaluate its potential as new drugs Moreover thestructure-activity relationships discussed in this review willprovide reference information for further exploring theirrelationships and continually discovering the new bioactiveoligosaccharide esters
Conflict of Interests
The authors declare that there is no conflict of interestsregarding the publication of this paper
References
[1] X D Yang L J Zhang B Liang L Z Xu and S L YangldquoOligosaccharide esters isolated from plants of PolygalaceaerdquoChinese Traditional and Herbal Drugs vol 33 no 10 pp 954ndash958 2002
[2] N Ogwuru and M Adamczeski ldquoBioactive natural productsderived from Polygonum species of plants their structures andmechanisms of actionrdquo Studies in Natural Products Chemistryvol 22 pp 607ndash642 2000
[3] S Kobayashi T Miyase and H Noguchi ldquoPolyphenolic glyco-sides and oligosaccharide multiesters from the roots of Polygaladalmaisianardquo Journal of Natural Products vol 65 no 3 pp 319ndash328 2002
[4] M Takasaki S Kuroki M Kozuka and T Konoshima ldquoNewphenylpropanoid esters of sucrose from Polygonum lapathi-foliumrdquo Journal of Natural Products vol 64 no 10 pp 1305ndash1308 2001
[5] M L Zimmermann and A T Sneden ldquoVanicosides A and Bprotein kinase C inhibitors from Polygonum pensylvanicumrdquoJournal of Natural Products vol 57 no 2 pp 236ndash242 1994
[6] M Takasaki T Konoshima S Kuroki H Tokuda and HNishino ldquoCancer chemopreventive activity of phenylpropanoid
20 Evidence-Based Complementary and Alternative Medicine
esters of sucrose vanicoside B and lapathoside A from Poly-gonum lapathifoliumrdquo Cancer Letters vol 173 no 2 pp 133ndash138 2001
[7] Q Fu T Liang Z Y Li et al ldquoSeparation of carbohydrates usinghydrophilic interaction liquid chromatographyrdquo CarbohydrateResearch vol 379 pp 13ndash17 2013
[8] M F Mrozek D Zhang and D Ben-Amotz ldquoOligosaccharideidentification and mixture quantification using Raman spec-troscopy and chemometric analysisrdquo Carbohydrate Researchvol 339 no 1 pp 141ndash145 2004
[9] G S Armstrong and B Bendiak ldquoHigh-resolution four-dimen-sional carbon-correlated 1H-1H ROESY experiments employ-ing isotags and the filter diagonalization method for effectiveassignment of glycosidic linkages in oligosaccharidesrdquo Journalof Magnetic Resonance vol 181 no 1 pp 79ndash88 2006
[10] G S Armstrong V A Mandelshtam A J Shaka and BBendiak ldquoRapid high-resolution four-dimensional NMR spec-troscopy using the filter diagonalization method and its advan-tages for detailed structural elucidation of oligosaccharidesrdquoJournal of Magnetic Resonance vol 173 no 1 pp 160ndash168 2005
[11] H-M Tseng S Gattolin J Pritchard H J Newbury and DA Barrett ldquoAnalysis of mono- di- and oligosaccharides by CEusing a two-stage derivatization method and LIF detectionrdquoElectrophoresis vol 30 no 8 pp 1399ndash1405 2009
[12] N Li X Li B L Hou and D L Meng ldquoNew disaccharosidefrom Camptosorus sibiricus Ruprrdquo Natural Product Researchvol 22 no 15 pp 1379ndash1383 2008
[13] Z Zhang D Wang Y Zhao H Gao Y-H Hu and J-FHu ldquoFructose-derived carbohydrates from Alisma orientalisrdquoNatural Product Research vol 23 no 11 pp 1013ndash1020 2009
[14] X Yang Y Zhao N He and K D Croft ldquoIsolation char-acterization and immunological effects of 120572-galacto-oligo-saccharides from a new source the herb Lycopus lucidus TurczrdquoJournal of Agricultural and Food Chemistry vol 58 no 14 pp8253ndash8258 2010
[15] R X Zhang Z P Jia L Y Kong et al ldquoStachyose extractfrom Rehmannia glutinosa Libosch to lower plasma glucose innormal and diabetic rats by oral administrationrdquo Pharmazievol 59 no 7 pp 552ndash556 2004
[16] R Zhang Y Zhao Y Sun X Lu and X Yang ldquoIsolationcharacterization and hepatoprotective effects of the raffinosefamily oligosaccharides from Rehmannia glutinosa liboschrdquoJournal of Agricultural and Food Chemistry vol 61 no 32 pp7786ndash7793 2013
[17] H Li F Song Z Zheng Z Liu and S Liu ldquoCharacterization ofsaccharides and phenolic acids in the Chinese herb Tanshen byESI-FT-ICR-MS and HPLCrdquo Journal of Mass Spectrometry vol43 no 11 pp 1545ndash1552 2008
[18] J E Deng J Zhang XM ChenW Ke and G Y Tian ldquoStudieson the physicochemical properties structure and antitumoractivity of an oligosaccharide homologue SnS-2 from the root ofScrophularia ningpoensis Hemslrdquo Chinese Journal of Chemistryvol 22 no 5 pp 492ndash497 2004
[19] S C Chou LM Chuang and S S Lee ldquoHypoglycemic constit-uents of gynura divaricata subsp formosanardquo Natural ProductCommunications vol 7 no 2 pp 221ndash222 2012
[20] F Feng L-L Wang X-P Lai Y-B Li Z-M Cao and Y-J Zhou ldquoStudy on oligosaccharides from Morinda officinalisrdquoJournal of Chinese Medicinal Materials vol 35 no 8 pp 1259ndash1262 2012
[21] Y F Li Z H Gong M Yang Y M Zhao and Z P Luo ldquoInhibi-tion of the oligosaccharides extracted fromMorinda officinalis
a Chinese traditional herbal medicine on the corticosteroneinduced apoptosis in PC12 cellsrdquo Life Sciences vol 72 no 8 pp933ndash942 2003
[22] Y-F Li Y-Q Liu M Yang et al ldquoThe cytoprotective effect ofinulin-type hexasaccharide extracted from Morinda officinalison PC12 cells against the lesion induced by corticosteronerdquo LifeSciences vol 75 no 13 pp 1531ndash1538 2004
[23] D N Olennikov L M Tankhaeva and A V Rokhin ldquoGlu-cofructans from Saussurea lappa rootsrdquo Chemistry of NaturalCompounds vol 47 no 3 pp 339ndash342 2011
[24] S K Hyun H A Jung B S Min J H Jung and J S ChoildquoIsolation of phenolics nucleosides saccharides and an alkaloidfrom the root of Aralia cordatardquo Natural Product Sciences vol16 no 1 pp 20ndash25 2010
[25] Z J Xu C W Lin and M F Liao ldquoStructure analysis of a newoligosaccharides BROS from Blumea ripariardquo Chinese Journalof Organic Chemistry vol 31 no 11 pp 1811ndash1819 2011
[26] Z J Xu C W Lin and Y Shi ldquoIsolation and structuredetermination of a new oligosaccharide from Blume ripariardquoJournal of Medicinal Plants Research vol 5 no 14 pp 2956ndash2962 2011
[27] Y Wang R Z Jiang G R Li et al ldquoStructural and enhancedmemory activity studies of extracts from Panax ginseng rootrdquoFood Chemistry vol 119 no 3 pp 969ndash973 2010
[28] DWan L Jiao H Yang and S Liu ldquoStructural characterizationand immunological activities of the water-soluble oligosaccha-rides isolated from thePanax ginseng rootsrdquoPlanta vol 235 no6 pp 1289ndash1297 2012
[29] L G Zhou C Z Yang J Q Li S L Wang and J Y WuldquoHeptasaccharide and octasaccharide isolated from Paris pol-yphylla var yunnanensis and their plant growth-regulatoryactivityrdquo Plant Science vol 165 no 3 pp 571ndash575 2003
[30] L G Zhou X D Cao R F Zhang Y L Peng S J Zhao andJ Y Wu ldquoStimulation of saponin production in Panax ginsenghairy roots by two oligosaccharides from Paris polyphylla varyunnanensisrdquo Biotechnology Letters vol 29 no 4 pp 631ndash6342007
[31] M Vanhaecke W van den Ende E Lescrinier and N Dyu-bankova ldquoIsolation and characterization of a pentasaccharidefrom Stellaria mediardquo Journal of Natural Products vol 71 no 11pp 1833ndash1836 2008
[32] J Feng and W Zhao ldquoComplete 1Hand 13C NMR assignmentsof four new oligosaccharides and two new glycosides fromPeriploca forrestiirdquoMagnetic Resonance in Chemistry vol 47 no8 pp 701ndash705 2009
[33] J Q Feng R J Zhang Y Zhou et al ldquoImmunosuppressive preg-nane glycosides from Periploca sepium and Periploca forrestiirdquoPhytochemistry vol 69 no 15 pp 2716ndash2723 2008
[34] X H Long R Xu Y H Zhang X H Tan andQ Y Sun ldquoA newoligosaccharide from Periploca calophyllardquo Zhongguo ZhongyaoZazhi vol 37 no 2 pp 226ndash229 2012
[35] L Wang Z-Q Yin Y Wang X-Q Zhang Y-L Li and W-CYe ldquoPerisesaccharides A-E new oligosaccharides from the rootbarks ofPeriploca sepiumrdquoPlantaMedica vol 76 no 9 pp 909ndash915 2010
[36] T Lei L Zhang H-Y Jiang Y Hu A-H Hong and Y-Z CenldquoA new pregnane glycoside and oligosaccharide from Parabar-ium huaitingiirdquo Journal of Asian Natural Products Research vol13 no 11 pp 1030ndash1035 2011
[37] J Li Y Jiang and P F Tu ldquoTricornoses A-L oligosaccharidemulti-esters from the roots of Polygala tricornisrdquo Journal ofNatural Products vol 68 no 5 pp 739ndash744 2005
Evidence-Based Complementary and Alternative Medicine 21
[38] H H Tu P Liu L Mu et al ldquoStudy on antidepressant com-ponents of sucrose ester from Polygala tenuifoliardquo ZhongguoZhongyao Zazhi vol 33 no 11 pp 1278ndash1280 2008
[39] G M She Y Y Ba Y Liu H Lv W Wang and R B ShildquoAbsorbable phenylpropenoyl sucroses from Polygala tenuifo-liardquoMolecules vol 16 no 7 pp 5507ndash5513 2011
[40] J Yong and P F Tu ldquoStudies on the chemical constituents inroot bark of Polygala tenuifolia (II)rdquo China Journal of ChineseMateria Medica vol 29 no 8 pp 751ndash753 2004
[41] M Ono C Takamura F Sugita et al ldquoTwo new steroidglycosides and a new sesquiterpenoid glycoside from theunderground parts of Trillium kamtschaticumrdquo Chemical andPharmaceutical Bulletin vol 55 no 4 pp 551ndash556 2007
[42] Y Ling Z Li M Chen Z Sun M Fan and C HuangldquoAnalysis and detection of the chemical constituents of RadixPolygalae and their metabolites in rats after oral administrationby ultra high-performance liquid chromatography coupledwith electrospray ionization quadrupole time-of-flight tandemmass spectrometryrdquo Journal of Pharmaceutical and BiomedicalAnalysis vol 85 pp 1ndash13 2013
[43] P Fan L Terrier A-E Hay A Marston and K HostettmannldquoAntioxidant and enzyme inhibition activities and chemicalprofiles ofPolygonum sachalinensis FSchmidt exMaxim (Polyg-onaceae)rdquo Fitoterapia vol 81 no 2 pp 124ndash131 2010
[44] L J Zhang C C Liao H C Huang Y C Shen L M Yangand Y H Kuo ldquoAntioxidant phenylpropanoid glycosides fromSmilax bracteatardquo Phytochemistry vol 69 no 6 pp 1398ndash14042008
[45] L L Yan W Y Gao Y J Zhang and Y Wang ldquoA new phenyl-propanoid glycosides from Paris polyphylla var yunnanensisrdquoFitoterapia vol 79 no 4 pp 306ndash307 2008
[46] Y H Kuo Y W Hsu C C Liaw J K Lee H C Huang andL M Y Kuo ldquoCytotoxic phenylpropanoid glycosides from thestems of Smilax chinardquo Journal of Natural Products vol 68 no10 pp 1475ndash1478 2005
[47] W-X Wang T-X Li H Ma J-F Zhang and A-Q JialdquoTumoral cytotoxic and antioxidative phenylpropanoid glyco-sides in Smilax riparia A DCrdquo Journal of Ethnopharmacologyvol 149 no 2 pp 527ndash532 2013
[48] N X Nhiem P vanKiem C vanMinh et al ldquoPhenylpropanoidglycosides fromHeterosmilax erythrantha and their antioxidantactivityrdquo Archives of Pharmacal Research vol 32 no 10 pp1373ndash1377 2009
[49] Y Wang W Y Gao T J Zhang and Y Q Guo ldquoA novelphenylpropanoid glycosides and a new derivation of phenolicglycoside from Paris Polyphylla var yunnanensisrdquo ChineseChemical Letters vol 18 no 5 pp 548ndash550 2007
[50] J-Y Zhang Y-Z Wang Y-L Zhao et al ldquoPhytochemicals andbioactivities of Paris speciesrdquo Journal of Asian Natural ProductsResearch vol 13 no 7 pp 670ndash681 2011
[51] N H N Hashim F Abas K Shaari and N H Lajis ldquoLC-DAD-ESIMSMS characterization of antioxidant and anti-cholinesterase constituents present in the active fraction fromPersicaria hydropiperrdquo LWT Food Science and Technology vol46 no 2 pp 468ndash476 2012
[52] PH FanA EHayAMarstonHX Lou andKHostettmannldquoChemical variability of the invasive neophytes Polygonumcuspidatum Sieb and Zucc and Polygonum sachalinensis FSchmidt ex Maximrdquo Biochemical Systematics and Ecology vol37 no 1 pp 24ndash34 2009
[53] P Liu Y Hu D H Guo et al ldquoPotential antidepressantproperties of Radix Polygalae (Yuan Zhi)rdquo Phytomedicine vol17 no 10 pp 794ndash799 2010
[54] J F Wu S B Chen S L Chen and P F Tu ldquoThe chemical con-stituents of Polygala hongkongensisHemslrdquoActa PharmaceuticaSinica vol 42 no 7 pp 757ndash761 2007
[55] Y Song Y Jiang D Bi X Tian L Liang and P Tu ldquoChemicalconstituents from n-butanol extract of aerial part of Polygalasibiricardquo Zhongguo Zhongyao Zazhi vol 37 no 4 pp 471ndash4742012
[56] Y Ikeya S Takeda M Tunakawa et al ldquoCognitive improvingand cerebral protective effects of acylated oligosaccharides inPolygala tenuifoliardquo Biological and Pharmaceutical Bulletin vol27 no 7 pp 1081ndash1085 2004
[57] C J Zheng C L Hu X Q Ma C Peng H Zhang and L PQin ldquoCytotoxic phenylpropanoid glycosides from Fagopyrumtataricum (L) Gaertnrdquo Food Chemistry vol 132 no 1 pp 433ndash438 2012
[58] X Li Y F Zhang L Yang et al ldquoChemical profiling ofconstituents of Smilacis glabrae using ultra-high pressure liquidchromatography coupled with LTQ orbitrap mass spectrome-tryrdquo Natural Product Communications vol 7 no 2 pp 181ndash1842012
[59] T-T Sun D-W Zhang Y Han F-Y Dong andWWang ldquoSmi-lasides M and N two new phenylpropanoid glycosides fromSmilax ripariardquo Journal of Asian Natural Products Research vol14 no 2 pp 165ndash170 2012
[60] J Li X Bi G Zheng Y Hitoshi T Ikeda and T NoharaldquoSteroidal glycosides and aromatic compounds from Smilaxripariardquo Chemical amp Pharmaceutical Bulletin vol 54 no 10 pp1451ndash1454 2006
[61] N Wang X Yao R Ishii and S Kitanaka ldquoBioactive sucroseesters from Bidens parviflorardquo Phytochemistry vol 62 no 5 pp741ndash746 2003
[62] S Nakamura K Fujimoto T Matsumoto et al ldquoAcylatedsucroses and acylated quinic acids analogs from the flower budsof Prunus mume and their inhibitory effect on melanogenesisrdquoPhytochemistry vol 92 pp 128ndash136 2013
[63] K Fujimoto SNakamura TMatsumoto et al ldquoMedicinal flow-ers XXXVIII Structures of acylated sucroses and inhibitoryeffects of constituents on aldose reducatase from the flower budsofPrunusmumerdquoChemical and Pharmaceutical Bulletin vol 61no 4 pp 445ndash451 2013
[64] S Nakamura K Fujimoto T Matsumoto et al ldquoStructuresof acylated sucroses and an acylated flavonol glycoside andinhibitory effects of constituents on aldose reductase from theflower buds of Prunus mumerdquo Journal of Natural Medicines vol67 no 4 pp 799ndash806 2013
[65] L-B Dong J He X-Y Li et al ldquoChemical constituents fromthe aerial parts of Musella lasiocarpardquo Natural Products andBioprospecting vol 1 no 1 pp 41ndash47 2011
[66] Y Xiong K Z Deng Y Q Guo W Y Gao and T J ZhangldquoNew chemical constituents from the rhizomes of Sparganiumstoloniferumrdquo Archives of Pharmacal Research vol 32 no 5 pp717ndash720 2009
[67] Y Xiong K-Z Deng Y-Q Guo W-Y Gao and T-J ZhangldquoTwo new sucrose esters from Sparganium stoloniferumrdquo Jour-nal of Asian Natural Products Research vol 10 no 5 pp 425ndash428 2008
[68] B Chen N L Wang J H Huang and X S Yao ldquoIridoidand phenylpropanoid glycosides from Scrophularia ningpoensis
22 Evidence-Based Complementary and Alternative Medicine
Hemslrdquo Asian Journal of Traditional Medicines vol 2 no 3 pp119ndash123 2007
[69] H Chen Y Z Zhou L Qiao et al ldquoTwo new compounds fromCynanchum amplexicaulerdquo Journal of Asian Natural ProductsResearch vol 10 no 3 pp 248ndash251 2008
[70] C-L Chang L-J Zhang R Y Chen et al ldquoAntioxidant andanti-inflammatory phenylpropanoid derivatives from Calamusquiquesetinerviusrdquo Journal of Natural Products vol 73 no 9 pp1482ndash1488 2010
[71] Y Kawai H Kumagai H Kurihara K Yamazaki R Sawanoand N Inoue ldquo120573-Glucosidase inhibitory activities of phenyl-propanoid glycosides vanicoside A and B from Polygonumsachalinense rhizomerdquo Fitoterapia vol 77 no 6 pp 456ndash4592006
[72] P V Kiem N X Nhiem N X Cuong et al ldquoNew phenyl-propanoid esters of sucrose from Polygonum hydropiper andtheir antioxidant activityrdquo Archives of Pharmacal Research vol31 no 11 pp 1477ndash1482 2008
[73] K J Wang Y J Zhang and C R Yang ldquoAntioxidant phenolicconstituents from Fagopyrum dibotrysrdquo Journal of Ethnophar-macology vol 99 no 2 pp 259ndash264 2005
[74] N Cho J Huh H Yang et al ldquoChemical constituentsof Polygala tenuifolia roots and their inhibitory activity onlipopolysaccharide-induced nitric oxide production in BV2microgliardquo Journal of Enzyme Inhibition and Medicinal Chem-istry vol 27 no 1 pp 1ndash4 2012
[75] Q Ren C S Wu and J L Zhang ldquoUse of on-line stop-flowheart-cutting two-dimensional high performance liquid chro-matography for simultaneous determination of 12 major con-stituents in tartary buckwheat (Fagopyrum tataricum Gaertn)rdquoJournal of Chromatography A vol 1304 pp 257ndash262 2013
[76] Q Ren C S Wu Y Ren and J L Zhang ldquoCharacterizationand identification of the chemical constituents from tartarybuckwheat (Fagopyrum tataricumGaertn) by high performanceliquid chromatographyphotodiode array detectorlinear iontrap FTICR hybrid mass spectrometryrdquo Food Chemistry vol136 no 3-4 pp 1377ndash1389 2013
[77] W Li Y N Sun X T Yan et al ldquoNF-120581B inhibitory activityof sucrose fatty acid esters and related constituents fromAstragalus membranaceusrdquo Journal of Agricultural and FoodChemistry vol 61 no 29 pp 7081ndash7088 2013
[78] J T Cheng J He Y Li et al ldquoThree new sucrose fatty acid estersfrom Equisetum hiemale LrdquoHelvetica Chimica Acta vol 95 no7 pp 1158ndash1163 2012
[79] Y Jiang and P-F Tu ldquoTenuifoliose Q a new oligosaccharideester from the root of Polygala tenuifoliaWilldrdquo Journal of AsianNatural Products Research vol 5 no 4 pp 279ndash283 2003
[80] M Yoshikawa H Matsuda T Morikawa H H Xie S Naka-mura and O Muraoka ldquoPhenylethanoid oligoglycosides andacylated oligosugars with vasorelaxant activity from Cistanchetubulosardquo Bioorganic ampMedicinal Chemistry vol 14 no 22 pp7468ndash7475 2006
[81] P-F Tu H-M Shi Z-H Song Y Jiang and Y-Y ZhaoldquoChemical constituents of Cistanche sinensisrdquo Journal of AsianNatural Products Research vol 9 no 1 pp 79ndash84 2007
[82] C-L Si Y-Y Lu P-P Qin R-C Sun and Y-H Ni ldquoPhenolicextractives with chemotaxonomic significance from the bark ofPaulownia tomentosa var tomentosardquo BioResources vol 6 no4 pp 5086ndash5098 2011
[83] J Wu S Zhang Q Xiao et al ldquoPhenylethanoid and aliphaticalcohol glycosides from Acanthus ilicifoliusrdquo Phytochemistryvol 63 no 4 pp 491ndash495 2003
[84] Y Jiang and P-F Tu ldquoAnalysis of chemical constituents inCistanche speciesrdquo Journal of Chromatography A vol 1216 no11 pp 1970ndash1979 2009
[85] H Otsuka H Kuwabara and H Hoshiyama ldquoIdentification ofsucrose diesters of aryldihydronaphthalene-type lignans fromTrigonotis peduncularisand the nature of their fluorescencerdquoJournal of Natural Products vol 71 no 7 pp 1178ndash1181 2008
[86] M-R Suo J-S Yang and Q-H Liu ldquoLignan oligosaccharideesters from Eritrichium rupestrerdquo Journal of Natural Productsvol 69 no 4 pp 682ndash684 2006
[87] P-F Tu Z-H Song H-M Shi Y Jiang and Y-Y ZhaoldquoArylethyl (=phenylethanoid) glycosides and oligosaccharidefrom the stem of Cistanche tubulosardquo Helvetica Chimica Actavol 89 no 5 pp 927ndash935 2006
[88] M-H Shyr T-H Tsai and L-C Lin ldquoRossicasins A Band rosicaside F three new phenylpropanoid glycosides fromBoschniakia rossicardquoChemical and Pharmaceutical Bulletin vol54 no 2 pp 252ndash254 2006
[89] R FangNCVeitchGCKiteM J RHowes EA Porter andM S J Simmonds ldquoGlycosylated constituents of Iris fulvaandIris brevicaulisrdquoChemical amp Pharmaceutical Bulletin vol 59 no1 pp 124ndash128 2011
[90] J Fu L Zuo J Yang R Chen and D Zhang ldquoOligosaccharidepolyester and triterpenoid saponins from the roots of Polygalajaponicardquo Phytochemistry vol 69 no 7 pp 1617ndash1624 2008
[91] M-C Cheng C-Y Li H-C Ko F-N Ko Y-L Lin andT-S Wu ldquoAntidepressant principles of the roots of polygalatenuifoliardquo Journal of Natural Products vol 69 no 9 pp 1305ndash1309 2006
[92] H T Chang and P F Tu ldquoNew oligosaccharide esters andxanthone C-glucosides from Polygala telephioidesrdquo HelveticaChimica Acta vol 90 no 5 pp 944ndash950 2007
[93] J Li L Feng J Dai R Wang and T Nohara ldquoChemical con-stituents from Polygala telephioidesrdquo China Journal of ChineseMateria Medica vol 34 no 4 pp 402ndash405 2009
[94] W-P Yin T-Z Zhao and H-Y Zhang ldquoA novel oligosaccha-ride ester from Syringa pubescensrdquo Journal of Asian NaturalProducts Research vol 10 no 1 pp 95ndash100 2008
[95] M Valko D Leibfritz J Moncol M T D Cronin M Mazurand J Telser ldquoFree radicals and antioxidants in normal physio-logical functions and human diseaserdquoThe International Journalof Biochemistry amp Cell Biology vol 39 no 1 pp 44ndash84 2007
[96] D Krishnaiah R Sarbatly and R Nithyanandam ldquoA review ofthe antioxidant potential of medicinal plant speciesrdquo Food andBioproducts Processing vol 89 no 3 pp 217ndash233 2011
[97] P Liu Y Hu D-H Guo et al ldquoAntioxidant activity ofoligosaccharide ester extracted from Polygala tenuifolia roots insenescence-accelerated micerdquo Pharmaceutical Biology vol 48no 7 pp 828ndash833 2010
[98] Y Hu H-B Liao G Dai-Hong P Liu Y-Y Wang and KRahman ldquoAntidepressant-like effects of 361015840-disinapoyl sucroseon hippocampal neuronal plasticity and neurotrophic signalpathway in chronically mild stressed ratsrdquo NeurochemistryInternational vol 56 no 3 pp 461ndash465 2010
[99] Y Hu H B O Liao P Liu D-H Guo and K RahmanldquoA bioactive compound from Polygala tenuifolia regulatesefficiency of chronic stress on hypothalamic-pituitary-adrenalaxisrdquo Pharmazie vol 64 no 9 pp 605ndash608 2009
[100] A Jungbauer and SMedjakovic ldquoAnti-inflammatory propertiesof culinary herbs and spices that ameliorate the effects ofmetabolic syndromerdquoMaturitas vol 71 no 3 pp 227ndash239 2012
Evidence-Based Complementary and Alternative Medicine 23
[101] Q Xu Y Wang S Guo Z Shen and L Yang ldquoAnti-inflammatory and analgesic activity of aqueous extract of Flospopulirdquo Journal of Ethnopharmacology vol 152 no 3 pp 540ndash545 2014
[102] K S Kim D S Lee G S Bae et al ldquoThe inhibition of JNKMAPK and NF-120581B signaling by tenuifoliside A isolated fromPolygala tenuifolia in lipopolysaccharide-induced macrophagesis associated with its anti-inflammatory effectrdquo European Jour-nal of Pharmacology vol 721 no 1ndash3 pp 267ndash276 2013
[103] J-G Lee J-M Yon C Lin A Y Jung K Y Jung and S-YNamldquoCombined treatment with capsaicin and resveratrol enhancesneuroprotection against glutamate-induced toxicity in mousecerebral cortical neuronsrdquo Food and Chemical Toxicology vol50 no 11 pp 3877ndash3885 2012
[104] M L Jin S Y Park Y H Kim J-I Oh S J Lee andG Park ldquoThe neuroprotective effects of cordycepin inhibitglutamate-induced oxidative andER stress-associated apoptosisin hippocampal HT22 cellsrdquo NeuroToxicology vol 41 pp 102ndash111 2014
[105] P Liu Y Hu J Li et al ldquoProtection of SH-SY5Y neuronal cellsfrom glutamate-induced apoptosis by 36rsquo-disinapoyl sucrosea bioactive compound isolated from radix polygalardquo Journal ofBiomedicine and Biotechnology vol 2012 Article ID 728342 5pages 2012
[106] P-B Li W-L Lin Y-G Wang W Peng X-Y Cai and W-WSu ldquoAntidiabetic activities of oligosaccharides of Ophiopogonisjaponicus in experimental type 2 diabetic ratsrdquo InternationalJournal of Biological Macromolecules vol 51 no 5 pp 749ndash7552012
[107] T Liu Y M Yip L Song et al ldquoInhibiting enzymatic starchdigestion by the phenolic compound diboside A a mechanisticand in silico studyrdquo Food Research International vol 54 no 1pp 595ndash600 2013
[108] F Cote andMGHahn ldquoOligosaccharins structures and signaltransductionrdquo Plant Molecular Biology vol 26 no 5 pp 1379ndash1411 1994
[109] RACreelman and J EMullet ldquoOligosaccharins brassinolidesand jasmonates nontraditional regulators of plant growthdevelopment and gene expressionrdquo Plant Cell vol 9 no 7 pp1211ndash1223 1997
[110] L Jiao D Wan X Zhang B Li H Zhao and S LiuldquoCharacterization and immunostimulating effects on murineperitoneal macrophages of oligosaccharide isolated from Panaxginseng CAMeyerrdquo Journal of Ethnopharmacology vol 144 no3 pp 490ndash496 2012
Submit your manuscripts athttpwwwhindawicom
Stem CellsInternational
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
MEDIATORSINFLAMMATION
of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Behavioural Neurology
EndocrinologyInternational Journal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Disease Markers
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
BioMed Research International
OncologyJournal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
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Oxidative Medicine and Cellular Longevity
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
PPAR Research
The Scientific World JournalHindawi Publishing Corporation httpwwwhindawicom Volume 2014
Immunology ResearchHindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Journal of
ObesityJournal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
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Computational and Mathematical Methods in Medicine
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Research and TreatmentAIDS
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
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Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Parkinsonrsquos Disease
Evidence-Based Complementary and Alternative Medicine
Volume 2014Hindawi Publishing Corporationhttpwwwhindawicom
Evidence-Based Complementary and Alternative Medicine 15
OH
OH
OH
OH
OH
OHOH
OHOH
OHOH
OH
OHOHOH
OH
OH
OH
OHOH
OH
OH
OHOH
H
H H
HO
O
O
O
O
O
O
O
OO
OO
O
OO
O
HO
HO
HO
OO
O
O
OO
OO
O
OO
O
OO
O
OO
O
O
O
OO
O
O
OO
O
OO
OOOO
HO
HO
HO
HO
HO
HO
HO
HO
HO
HO
HOHO
HO
HO
HO
HO
HO
150 151 152
153 180
AcO
AcO
AcOAcO
OAc
OAc
CH2OH
OHOH
OH OHOH
OHOH
OH
OHOH
CH3O
Figure 5
Table 5 Phenylpropanoid-derived tetrasaccharide esters
Number Name R1 R2 R3 Source Parts Reference154 Tricornose G K H K Polygala tricornis Roots [37]155 Tricornose H K K K Polygala tricornis Roots [37]156 Tricornose I K K L Polygala tricornis Roots [37]157 Tricornose J K I L Polygala tricornis Roots [37]158 Tricornose K K I K Polygala tricornis Roots [37]159 Tricornose L K G K Polygala tricornis Roots [37]See Scheme 5
Smilax riparia including smiglasides A (48) and B (49) 26-di-acetyl-3101584061015840-di-feruloylsucrose (73) helonioside B (40)and smilaside P (65) Only smiglasidesA andB and smilasideP exhibited cytotoxicity against human tumor cell lines withdifferent inhibitory concentrations comparing with cisplatinand paclitaxel as positive controls [47] Helonioside A (39)exhibited higher cytotoxicity with the increase of concentra-tion (01ndash100120583gmL) [45] Tatarisides AndashG (45 119ndash121 46122 47) and diboside A (116) from the Fagopyrum genusexerted cytotoxic activities against different human cell linesand the cytotoxicity of tatariside C was the most remarkablewith the IC
50values ranging from 644 to 749 120583gmL [57]
11015840236-O-Tetra-acetyl-31015840-O-cis-feruloylsucrose (95) fromthe Sparganium plants exhibited extremely weak cyto-toxicity against the growth of mice Lung Adenocarcinoma
795 cell lines with an IC50
value of 116 120583gmL [66] SnS-2oligosaccharides mixture including raffinose (3) stachyose(19) and verbascose (21) from the roots of Scrophularianingpoensis had antitumor activity against the growth ofLewis pulmonary carcinoma cells transplanted into mice[18]
Disaccharide esters and oligosaccharides mixture fromthe Liliaceae Polygonaceae Sparganiaceae and Scrpophular-iaceae families showed effective cytotoxic and antineoplasticactivities The study results indicated that feruloyl and acetylgroups play an important role in mediating cytotoxicitywhich seems to be related to the substitution position offeruloyl groups The feruloyl groups at C-6 or C-11015840 are vitalfor cytotoxicity In addition the increased number of acetylgroups could induce higher tumoricidal activity
16 Evidence-Based Complementary and Alternative Medicine
Table 6 Phenylpropanoid-derived pentasaccharide esters
Number Name R1 R2 R3 R4 R5 R6 Source Parts Reference160 Tenuifoliose A G D I Ac Ac Ac Polygala tenuifolia Roots [38 42]161 Tenuifoliose B G D I H Ac Ac Polygala tenuifolia Roots [42]162 Tenuifoliose C G D I H H H Polygala tenuifolia Roots [42]163 Tenuifoliose F G D U Ac Ac Ac Polygala tenuifolia Roots [42]164 Tenuifoliose G G D U Ac H Ac Polygala tenuifolia Roots [42]165 Tenuifoliose H G D G Ac Ac Ac Polygala tenuifolia Roots [38 42 79]166 Tenuifoliose I G D G Ac H Ac Polygala tenuifolia Roots [42 79]167 Tenuifoliose J G D G H Ac Ac Polygala tenuifolia Roots [42]168 Tenuifoliose K G D G H H Ac Polygala tenuifolia Roots [42]169 Tenuifoliose L G D T Ac Ac Ac Polygala tenuifolia Roots [42 79]170 Tenuifoliose M G D T Ac H Ac Polygala tenuifolia Roots [42]171 Tenuifoliose N I D I Ac Ac Ac Polygala tenuifolia Roots [42]172 Tenuifoliose O I D I H Ac Ac Polygala tenuifolia Roots [42]173 Tenuifoliose P I D I H H Ac Polygala tenuifolia Roots [42]174 Tenuifoliose Q G D T H Ac Ac Polygala tenuifolia Roots [79]175 Tenuifoliose S G D G H H H Polygala tenuifolia Roots [42]176 Tenuifoliose T G D I H H H Polygala tenuifolia Roots [42]177 Tenuifoliose V H D I Ac Ac Ac Polygala tenuifolia Roots [42]178 Tenuifoliose W I D U Ac H Ac Polygala tenuifolia Roots [42]179 Tenuifoliose X I D I H H H Polygala tenuifolia Roots [42]See Scheme 6
O
OO
O
O
O
O
OR1
OH
OH
OH
OHOH
OH
HOHO
HO
HO
OR2
R3O
CH2OH
Scheme 5
34 Anti-Inflammatory Activity Inflammation an importantbasic pathological process is a defense response of biopsywith vascular system to damage stimuli such as pathogensimpaired cells and tissues and physical and chemical factorsHowever if the process of inflammatory response cannot endnormally when cell debris and pathogens were cleared thebiological defence response will become causative factor andbring about many diseases such as diabetes cardiovasculardiseases metabolic syndrome and cancer [100 101]
Tenuifoliside A (44) from the Polygala genus exhibitedstrong anti-inflammatory effect not only by suppressing the
production of NO but also by reducing the production ofiNOS prostaglandin E2 cyclooxygenase-2 and proinflam-matory cytokines through the inhibition of the mitogen-activated protein kinases pathway and NF-120581B pathway [102]The anti-inflammatory activities of quiquesetinerviusides D(108) and E (109) from the Calamus genus were evaluated inRAW 2647 cells Both of them showed significant inhibitoryeffects against the production of LPS-stimulated NOwith theIC50values of 90ndash295120583M [70]Six disaccharide fatty acid esters (132ndash137) were iso-
lated from the Astragalus and Equisetum genera The anti-inflammatory effects of these isolated compounds have alsobeen documented The activation of NF-120581B could upregulatethe expression of proinflammatory cytokines inducible nitricoxide synthase (iNOS) and tumornecrosis factor alpha (TNF-120572) The NF-120581B inhibitory activities of compounds 132ndash137were tested in HepG2 cells stimulated with TNF-120572 All ofthese compounds could significantly restrainTNF-120572-inducedNF-120581B transcriptional activities with the IC
50values of 44ndash
247 120583M Li et al pointed out that olefinic bonds and thelength of the fatty acid moieties contributed to the NF-120581B inhibitory activity Furthermore the inhibition increasedsignificantly with the increase of the number of olefinic bondson the aliphatic moiety [77] These results may provide ascientific basis for the development of new anti-inflammatoryagents
35 Neuroprotective and Cerebral Protective Activities Aswe all know glutamate works as a major excitatory aminoacid neurotransmitter in the mammalian central nervous
Evidence-Based Complementary and Alternative Medicine 17
R6O
R2O
OR3
OR5
OR4
CH2OR1
OCH3
Rham
OO
O
OO O
O
O
O
OO
RhamO
O
OH
OH
OHOH
OH
OHOH
OHHO
HO
HO
T O-rhamnosyl-coumaroyl U O-rhamnosyl-feruloyl
Scheme 6
system and plays a crucial role in several physiological pro-cesses [103] However the accumulation of glutamate inducesdiverse acute and chronic neurodegenerative diseases suchas epilepsy ischemic stroke and Parkinsonrsquos disease aswell as Alzheimerrsquos disease [104] DISS (123) isolated fromthe Polygala genus exhibited neuroprotective effect againstglutamate-induced SH-SY5Y neuronal cell damage The invitro test demonstrated that DISS (06 6 and 60 120583molL)played a critical role in increasing cell viability controllinglactate dehydrogenase and attenuated apoptosis ranging from195 to 258 [105]
Tenuifoliside B (102) from the Polygala genus was ableto significantly shorten the coma time of KCN-inducedanoxia mice at the doses of 3 and 10mgkg and it playedan important role in ameliorating the scopolamine-inducedimpairment of performance in passive avoidance task inrats and enhancing the tremors induced by oxotremorine inmiceThese results together demonstrated that tenuifoliside Bpossessed cognitive improving and cerebral protective effects[56]
36 Antidiabetic Activity Diabetes mellitus a chronic debil-itating metabolic disease is characterized by high bloodglucose content and comprises three types termed type Itype II and gestational diabetes [106] Stachyose (19) extract(a part) from Rehmannia glutinosa obviously exhibited theactivity of downregulating fasting plasma glucose level andpartially keeping from hyperglycemia induced by adrenalineand glucose without obvious dose-dependent effect Otherthan that in vivo tests in rats induced by alloxan revealed
that stachyose extract at the dose of 200mgkg significantlydecreased blood-sugar level [15]
Diboside A lapathosides C and D vanicosides A andB and hydropiperoside were isolated from the FagopyrumPolygonum and Persicaria genera belonging to the Polygo-naceae family Diboside A (116) could potentially inhibit 120572-amylase activity with an IC
50of 269 120583M and thus retard the
starch digestion rate which is helpful for diabetic individualsin controlling blood sugar level [107] Lapathoside D (38)exerted stronger activity of 120572-glucosidase inhibition with anIC50
value of 0113mM than acarbose which was chosen asa positive drug for the treatment of type II diabetes [43]Vanicoside B (111) was reported to have higher 120573-glucosidaseinhibitory activity with an IC
50of 505 120583M than vanicoside A
(110) with an IC50of 599 120583M because of the acetyl moiety of
the latter possibly decreasing inhibitory activity of vanicosideA [71]
Fujimoto et al investigated the inhibitory effects ofmumeoses FndashO (83ndash92) from the Prunus genus on aldosereductase and discovered that caffeoyl groups are crucialfor the inhibitory effect on aldose reductase And thusmumeoses F G H J K L M and N (IC
50= 22ndash77120583M) with
a coumaroyl group and acetyl groups inhibited moderatelyaldose reductase from reducing glucose to sorbitol whichis associated with the chronic complications of diabetes [6364]
37 Elicitors and Regulators Oligosaccharides are quitepropitious for encoding biological information because ofdiverse monosaccharide units and complex molecular struc-tures and they are therefore first described as biological
18 Evidence-Based Complementary and Alternative Medicine
181 H
H
H
H
H
H
H
H
H H
H
H
H
H
H
H
H H
HH
Benzyl
Benzyl
Benzyl
182
183
184 Ac
Ac
Ac
Ac
Ac
Ac
Ac
Ac
Ac
Ac
185
186
187
188
189
R1 R2 R3
R1 R2 R3 R4
OCH3
R3OH2C OR2
OR1
OR1
O
O
O
O O
OOO
O
OO
O
OH
OH
OH OH
OH
O O
O
O
OH
HO
OH
OH OHOH
OH
OH
OHHO
HO
OH
OH
HO
CH2OH
CH2OH
CH2OH
CH2OH
C
R2O
R3O
CH2OR4
CH2CH2 CH2CH2CH2CH2CH3
CH3
CH3
191190 192
193
O
C C
O
OO
OO
OO
OO
O O
O
O
O
O
O
O
OH
OH
OHHO
HO
HOOH
OH
OH
OH
HO
OH
OH
OH
OH
HO
HO
C C
R998400O
R998400
Figure 6
signals in plants [108] Oligosaccharides from the cell wallfragments of plants and fungi are powerful signal moleculessuch as the elicitors of plant defence response and theregulators of plant growth and they are capable of exertingbiological activities at exceedingly low concentrations [109]Heptasaccharide (HS) (15) and octasaccharide (OS) (16) iso-lated from the Paris genus possessed plant growth-regulatory
activities [29 30]The two oligosaccharides significantly pro-moted the proliferation of Paris polyphylla var yunnanensisroots at the doses of 25ndash20mgL The octasaccharide hadthe most obvious effect on the growth of Panax japonicusvar major hairy roots at a dose of 30mgL while the otherhad the most positive effect on saponin accumulation ofPanax japonicus var major hairy roots at a dose of 10mgL
Evidence-Based Complementary and Alternative Medicine 19
[29] Similarly Zhou et al evaluated the stimulating effectsof HS and OS on the root growth and saponin productionof Panax ginseng hairy roots which were induced from theplant roots infected withAgrobacterium rhizogenes strain A4The results showed that there was a maximum effect on thehairy roots growth and saponin accumulation on day 10Compared with control group the root biomass dry weightwas increased by more than 17-fold while the total saponincontent of roots increased by more than 1-fold when thesetwo oligosaccharides were added to the hairy root at a dose of30mgL [30] The above data illustrate that HS and OS couldserve as the plant growth-regulators not only in their originalspecies but also in others
38 Immunopotentiating Activity Macrophages are impor-tant targets of investigations on cytophagy cellular immunityand molecular immunology Therefore they are deemedto play a vital role in host defense comprising phagocy-tosis proteolytic processing pathogenic agent apoptosiscytokines production and foreign antigens presentation[110] The water-extracted oligosaccharides from Panax gin-seng (WGOS) exhibited better immunopotentiating activ-ity by increasing phagocytic function of macrophages andpromoting NO TNF-120572 and reactive oxygen species pro-duction [110] In addition Wan et al have obtained malto-oligosaccharides (17 119899 = 3sim8) and three oligosaccharides (213 14) from the Panax ginseng roots The in vitro bioassaypointed out thatWGOS could serve as efficacious stimulatorsof B and T lymphocytes [28] These studies provided enlight-enment that the mixture of oligosaccharides from Chineseherbalmedicine exhibits significant effect on immune system
39 Others Acetylcholinesterase (AChE) inhibitors showgood therapeutic effects onmyasthenia gravis glaucoma andAlzheimerrsquos disease through reversible enzyme inhibitionso as to increase the accumulation of acetylcholine in thesynapse and then promote and prolong the function ofacetylcholine Vanicoside B (111) showed AChE inhibitoryactivity with an IC
50of 0062mM while hydropiperoside
(42) and lapathosides C (115) and D (38) just exhibited weakenzyme inhibitory activity [43]
Wang et al has explored low molecular mass carbohy-drate polymer from Panax ginseng roots and obtained 30ethanol elution (PGO)which included peptides and oligosac-charides (17 119899 = 0sim5) identified as maltose maltotriosemaltotetraose maltopentaose maltohexaose and maltohep-taose Pharmacological experiments revealed that PGO couldsignificantly enhance the memory in scopolamine-inducedmemory deficit rats [27]
Cistanoside F (129) and kankanose (150) were isolatedfrom the Cistanche Paulownia and Acanthus genera Phar-macological experiments showed that cistanoside F andkankanose significantly exhibited vasorelaxant effects on thenoradrenaline-induced contraction of thoracic aorta fromrats [80]
4 Conclusion
Traditional Chinese medicine from natural kingdom playsan indelible role in the treatment of human diseases andit has aroused the attention of those who have engagedin medicinal pharmaceutical chemistry Therefore scientistshave made great contributions day after day to investigate thevalid chemicals from traditional Chinese medicines In thepast decades about 193 oligosaccharides and their esters havebeen identified from traditional Chinese medicinal plantsOn the one hand only a few oligosaccharides and theirmixtures were investigated and just exhibited antidepres-sant antineoplastic antidiabetic plant growth-regulatoryimmunopotentiating and enhancedmemory activitiesMoreexploratory work is still needed to excavate biological andpharmacological activities of oligosaccharides On the otherhand oligosaccharide esters exhibited multi-advantageousactivities Bioassays have revealed that antioxidant cytotoxicantineoplastic and anti-inflammatory activities are the mostnotable bioactivities Of course to search for the naturalproducts with these activities is a hotpot in the contemporarydrug research Oligosaccharide esters provide a vast treasuretrove for medical researchers After considering the currentstudies it should be taken as future directions to makemore mechanism of action studies and clinical trials tofurther evaluate its potential as new drugs Moreover thestructure-activity relationships discussed in this review willprovide reference information for further exploring theirrelationships and continually discovering the new bioactiveoligosaccharide esters
Conflict of Interests
The authors declare that there is no conflict of interestsregarding the publication of this paper
References
[1] X D Yang L J Zhang B Liang L Z Xu and S L YangldquoOligosaccharide esters isolated from plants of PolygalaceaerdquoChinese Traditional and Herbal Drugs vol 33 no 10 pp 954ndash958 2002
[2] N Ogwuru and M Adamczeski ldquoBioactive natural productsderived from Polygonum species of plants their structures andmechanisms of actionrdquo Studies in Natural Products Chemistryvol 22 pp 607ndash642 2000
[3] S Kobayashi T Miyase and H Noguchi ldquoPolyphenolic glyco-sides and oligosaccharide multiesters from the roots of Polygaladalmaisianardquo Journal of Natural Products vol 65 no 3 pp 319ndash328 2002
[4] M Takasaki S Kuroki M Kozuka and T Konoshima ldquoNewphenylpropanoid esters of sucrose from Polygonum lapathi-foliumrdquo Journal of Natural Products vol 64 no 10 pp 1305ndash1308 2001
[5] M L Zimmermann and A T Sneden ldquoVanicosides A and Bprotein kinase C inhibitors from Polygonum pensylvanicumrdquoJournal of Natural Products vol 57 no 2 pp 236ndash242 1994
[6] M Takasaki T Konoshima S Kuroki H Tokuda and HNishino ldquoCancer chemopreventive activity of phenylpropanoid
20 Evidence-Based Complementary and Alternative Medicine
esters of sucrose vanicoside B and lapathoside A from Poly-gonum lapathifoliumrdquo Cancer Letters vol 173 no 2 pp 133ndash138 2001
[7] Q Fu T Liang Z Y Li et al ldquoSeparation of carbohydrates usinghydrophilic interaction liquid chromatographyrdquo CarbohydrateResearch vol 379 pp 13ndash17 2013
[8] M F Mrozek D Zhang and D Ben-Amotz ldquoOligosaccharideidentification and mixture quantification using Raman spec-troscopy and chemometric analysisrdquo Carbohydrate Researchvol 339 no 1 pp 141ndash145 2004
[9] G S Armstrong and B Bendiak ldquoHigh-resolution four-dimen-sional carbon-correlated 1H-1H ROESY experiments employ-ing isotags and the filter diagonalization method for effectiveassignment of glycosidic linkages in oligosaccharidesrdquo Journalof Magnetic Resonance vol 181 no 1 pp 79ndash88 2006
[10] G S Armstrong V A Mandelshtam A J Shaka and BBendiak ldquoRapid high-resolution four-dimensional NMR spec-troscopy using the filter diagonalization method and its advan-tages for detailed structural elucidation of oligosaccharidesrdquoJournal of Magnetic Resonance vol 173 no 1 pp 160ndash168 2005
[11] H-M Tseng S Gattolin J Pritchard H J Newbury and DA Barrett ldquoAnalysis of mono- di- and oligosaccharides by CEusing a two-stage derivatization method and LIF detectionrdquoElectrophoresis vol 30 no 8 pp 1399ndash1405 2009
[12] N Li X Li B L Hou and D L Meng ldquoNew disaccharosidefrom Camptosorus sibiricus Ruprrdquo Natural Product Researchvol 22 no 15 pp 1379ndash1383 2008
[13] Z Zhang D Wang Y Zhao H Gao Y-H Hu and J-FHu ldquoFructose-derived carbohydrates from Alisma orientalisrdquoNatural Product Research vol 23 no 11 pp 1013ndash1020 2009
[14] X Yang Y Zhao N He and K D Croft ldquoIsolation char-acterization and immunological effects of 120572-galacto-oligo-saccharides from a new source the herb Lycopus lucidus TurczrdquoJournal of Agricultural and Food Chemistry vol 58 no 14 pp8253ndash8258 2010
[15] R X Zhang Z P Jia L Y Kong et al ldquoStachyose extractfrom Rehmannia glutinosa Libosch to lower plasma glucose innormal and diabetic rats by oral administrationrdquo Pharmazievol 59 no 7 pp 552ndash556 2004
[16] R Zhang Y Zhao Y Sun X Lu and X Yang ldquoIsolationcharacterization and hepatoprotective effects of the raffinosefamily oligosaccharides from Rehmannia glutinosa liboschrdquoJournal of Agricultural and Food Chemistry vol 61 no 32 pp7786ndash7793 2013
[17] H Li F Song Z Zheng Z Liu and S Liu ldquoCharacterization ofsaccharides and phenolic acids in the Chinese herb Tanshen byESI-FT-ICR-MS and HPLCrdquo Journal of Mass Spectrometry vol43 no 11 pp 1545ndash1552 2008
[18] J E Deng J Zhang XM ChenW Ke and G Y Tian ldquoStudieson the physicochemical properties structure and antitumoractivity of an oligosaccharide homologue SnS-2 from the root ofScrophularia ningpoensis Hemslrdquo Chinese Journal of Chemistryvol 22 no 5 pp 492ndash497 2004
[19] S C Chou LM Chuang and S S Lee ldquoHypoglycemic constit-uents of gynura divaricata subsp formosanardquo Natural ProductCommunications vol 7 no 2 pp 221ndash222 2012
[20] F Feng L-L Wang X-P Lai Y-B Li Z-M Cao and Y-J Zhou ldquoStudy on oligosaccharides from Morinda officinalisrdquoJournal of Chinese Medicinal Materials vol 35 no 8 pp 1259ndash1262 2012
[21] Y F Li Z H Gong M Yang Y M Zhao and Z P Luo ldquoInhibi-tion of the oligosaccharides extracted fromMorinda officinalis
a Chinese traditional herbal medicine on the corticosteroneinduced apoptosis in PC12 cellsrdquo Life Sciences vol 72 no 8 pp933ndash942 2003
[22] Y-F Li Y-Q Liu M Yang et al ldquoThe cytoprotective effect ofinulin-type hexasaccharide extracted from Morinda officinalison PC12 cells against the lesion induced by corticosteronerdquo LifeSciences vol 75 no 13 pp 1531ndash1538 2004
[23] D N Olennikov L M Tankhaeva and A V Rokhin ldquoGlu-cofructans from Saussurea lappa rootsrdquo Chemistry of NaturalCompounds vol 47 no 3 pp 339ndash342 2011
[24] S K Hyun H A Jung B S Min J H Jung and J S ChoildquoIsolation of phenolics nucleosides saccharides and an alkaloidfrom the root of Aralia cordatardquo Natural Product Sciences vol16 no 1 pp 20ndash25 2010
[25] Z J Xu C W Lin and M F Liao ldquoStructure analysis of a newoligosaccharides BROS from Blumea ripariardquo Chinese Journalof Organic Chemistry vol 31 no 11 pp 1811ndash1819 2011
[26] Z J Xu C W Lin and Y Shi ldquoIsolation and structuredetermination of a new oligosaccharide from Blume ripariardquoJournal of Medicinal Plants Research vol 5 no 14 pp 2956ndash2962 2011
[27] Y Wang R Z Jiang G R Li et al ldquoStructural and enhancedmemory activity studies of extracts from Panax ginseng rootrdquoFood Chemistry vol 119 no 3 pp 969ndash973 2010
[28] DWan L Jiao H Yang and S Liu ldquoStructural characterizationand immunological activities of the water-soluble oligosaccha-rides isolated from thePanax ginseng rootsrdquoPlanta vol 235 no6 pp 1289ndash1297 2012
[29] L G Zhou C Z Yang J Q Li S L Wang and J Y WuldquoHeptasaccharide and octasaccharide isolated from Paris pol-yphylla var yunnanensis and their plant growth-regulatoryactivityrdquo Plant Science vol 165 no 3 pp 571ndash575 2003
[30] L G Zhou X D Cao R F Zhang Y L Peng S J Zhao andJ Y Wu ldquoStimulation of saponin production in Panax ginsenghairy roots by two oligosaccharides from Paris polyphylla varyunnanensisrdquo Biotechnology Letters vol 29 no 4 pp 631ndash6342007
[31] M Vanhaecke W van den Ende E Lescrinier and N Dyu-bankova ldquoIsolation and characterization of a pentasaccharidefrom Stellaria mediardquo Journal of Natural Products vol 71 no 11pp 1833ndash1836 2008
[32] J Feng and W Zhao ldquoComplete 1Hand 13C NMR assignmentsof four new oligosaccharides and two new glycosides fromPeriploca forrestiirdquoMagnetic Resonance in Chemistry vol 47 no8 pp 701ndash705 2009
[33] J Q Feng R J Zhang Y Zhou et al ldquoImmunosuppressive preg-nane glycosides from Periploca sepium and Periploca forrestiirdquoPhytochemistry vol 69 no 15 pp 2716ndash2723 2008
[34] X H Long R Xu Y H Zhang X H Tan andQ Y Sun ldquoA newoligosaccharide from Periploca calophyllardquo Zhongguo ZhongyaoZazhi vol 37 no 2 pp 226ndash229 2012
[35] L Wang Z-Q Yin Y Wang X-Q Zhang Y-L Li and W-CYe ldquoPerisesaccharides A-E new oligosaccharides from the rootbarks ofPeriploca sepiumrdquoPlantaMedica vol 76 no 9 pp 909ndash915 2010
[36] T Lei L Zhang H-Y Jiang Y Hu A-H Hong and Y-Z CenldquoA new pregnane glycoside and oligosaccharide from Parabar-ium huaitingiirdquo Journal of Asian Natural Products Research vol13 no 11 pp 1030ndash1035 2011
[37] J Li Y Jiang and P F Tu ldquoTricornoses A-L oligosaccharidemulti-esters from the roots of Polygala tricornisrdquo Journal ofNatural Products vol 68 no 5 pp 739ndash744 2005
Evidence-Based Complementary and Alternative Medicine 21
[38] H H Tu P Liu L Mu et al ldquoStudy on antidepressant com-ponents of sucrose ester from Polygala tenuifoliardquo ZhongguoZhongyao Zazhi vol 33 no 11 pp 1278ndash1280 2008
[39] G M She Y Y Ba Y Liu H Lv W Wang and R B ShildquoAbsorbable phenylpropenoyl sucroses from Polygala tenuifo-liardquoMolecules vol 16 no 7 pp 5507ndash5513 2011
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[42] Y Ling Z Li M Chen Z Sun M Fan and C HuangldquoAnalysis and detection of the chemical constituents of RadixPolygalae and their metabolites in rats after oral administrationby ultra high-performance liquid chromatography coupledwith electrospray ionization quadrupole time-of-flight tandemmass spectrometryrdquo Journal of Pharmaceutical and BiomedicalAnalysis vol 85 pp 1ndash13 2013
[43] P Fan L Terrier A-E Hay A Marston and K HostettmannldquoAntioxidant and enzyme inhibition activities and chemicalprofiles ofPolygonum sachalinensis FSchmidt exMaxim (Polyg-onaceae)rdquo Fitoterapia vol 81 no 2 pp 124ndash131 2010
[44] L J Zhang C C Liao H C Huang Y C Shen L M Yangand Y H Kuo ldquoAntioxidant phenylpropanoid glycosides fromSmilax bracteatardquo Phytochemistry vol 69 no 6 pp 1398ndash14042008
[45] L L Yan W Y Gao Y J Zhang and Y Wang ldquoA new phenyl-propanoid glycosides from Paris polyphylla var yunnanensisrdquoFitoterapia vol 79 no 4 pp 306ndash307 2008
[46] Y H Kuo Y W Hsu C C Liaw J K Lee H C Huang andL M Y Kuo ldquoCytotoxic phenylpropanoid glycosides from thestems of Smilax chinardquo Journal of Natural Products vol 68 no10 pp 1475ndash1478 2005
[47] W-X Wang T-X Li H Ma J-F Zhang and A-Q JialdquoTumoral cytotoxic and antioxidative phenylpropanoid glyco-sides in Smilax riparia A DCrdquo Journal of Ethnopharmacologyvol 149 no 2 pp 527ndash532 2013
[48] N X Nhiem P vanKiem C vanMinh et al ldquoPhenylpropanoidglycosides fromHeterosmilax erythrantha and their antioxidantactivityrdquo Archives of Pharmacal Research vol 32 no 10 pp1373ndash1377 2009
[49] Y Wang W Y Gao T J Zhang and Y Q Guo ldquoA novelphenylpropanoid glycosides and a new derivation of phenolicglycoside from Paris Polyphylla var yunnanensisrdquo ChineseChemical Letters vol 18 no 5 pp 548ndash550 2007
[50] J-Y Zhang Y-Z Wang Y-L Zhao et al ldquoPhytochemicals andbioactivities of Paris speciesrdquo Journal of Asian Natural ProductsResearch vol 13 no 7 pp 670ndash681 2011
[51] N H N Hashim F Abas K Shaari and N H Lajis ldquoLC-DAD-ESIMSMS characterization of antioxidant and anti-cholinesterase constituents present in the active fraction fromPersicaria hydropiperrdquo LWT Food Science and Technology vol46 no 2 pp 468ndash476 2012
[52] PH FanA EHayAMarstonHX Lou andKHostettmannldquoChemical variability of the invasive neophytes Polygonumcuspidatum Sieb and Zucc and Polygonum sachalinensis FSchmidt ex Maximrdquo Biochemical Systematics and Ecology vol37 no 1 pp 24ndash34 2009
[53] P Liu Y Hu D H Guo et al ldquoPotential antidepressantproperties of Radix Polygalae (Yuan Zhi)rdquo Phytomedicine vol17 no 10 pp 794ndash799 2010
[54] J F Wu S B Chen S L Chen and P F Tu ldquoThe chemical con-stituents of Polygala hongkongensisHemslrdquoActa PharmaceuticaSinica vol 42 no 7 pp 757ndash761 2007
[55] Y Song Y Jiang D Bi X Tian L Liang and P Tu ldquoChemicalconstituents from n-butanol extract of aerial part of Polygalasibiricardquo Zhongguo Zhongyao Zazhi vol 37 no 4 pp 471ndash4742012
[56] Y Ikeya S Takeda M Tunakawa et al ldquoCognitive improvingand cerebral protective effects of acylated oligosaccharides inPolygala tenuifoliardquo Biological and Pharmaceutical Bulletin vol27 no 7 pp 1081ndash1085 2004
[57] C J Zheng C L Hu X Q Ma C Peng H Zhang and L PQin ldquoCytotoxic phenylpropanoid glycosides from Fagopyrumtataricum (L) Gaertnrdquo Food Chemistry vol 132 no 1 pp 433ndash438 2012
[58] X Li Y F Zhang L Yang et al ldquoChemical profiling ofconstituents of Smilacis glabrae using ultra-high pressure liquidchromatography coupled with LTQ orbitrap mass spectrome-tryrdquo Natural Product Communications vol 7 no 2 pp 181ndash1842012
[59] T-T Sun D-W Zhang Y Han F-Y Dong andWWang ldquoSmi-lasides M and N two new phenylpropanoid glycosides fromSmilax ripariardquo Journal of Asian Natural Products Research vol14 no 2 pp 165ndash170 2012
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[61] N Wang X Yao R Ishii and S Kitanaka ldquoBioactive sucroseesters from Bidens parviflorardquo Phytochemistry vol 62 no 5 pp741ndash746 2003
[62] S Nakamura K Fujimoto T Matsumoto et al ldquoAcylatedsucroses and acylated quinic acids analogs from the flower budsof Prunus mume and their inhibitory effect on melanogenesisrdquoPhytochemistry vol 92 pp 128ndash136 2013
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[65] L-B Dong J He X-Y Li et al ldquoChemical constituents fromthe aerial parts of Musella lasiocarpardquo Natural Products andBioprospecting vol 1 no 1 pp 41ndash47 2011
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[68] B Chen N L Wang J H Huang and X S Yao ldquoIridoidand phenylpropanoid glycosides from Scrophularia ningpoensis
22 Evidence-Based Complementary and Alternative Medicine
Hemslrdquo Asian Journal of Traditional Medicines vol 2 no 3 pp119ndash123 2007
[69] H Chen Y Z Zhou L Qiao et al ldquoTwo new compounds fromCynanchum amplexicaulerdquo Journal of Asian Natural ProductsResearch vol 10 no 3 pp 248ndash251 2008
[70] C-L Chang L-J Zhang R Y Chen et al ldquoAntioxidant andanti-inflammatory phenylpropanoid derivatives from Calamusquiquesetinerviusrdquo Journal of Natural Products vol 73 no 9 pp1482ndash1488 2010
[71] Y Kawai H Kumagai H Kurihara K Yamazaki R Sawanoand N Inoue ldquo120573-Glucosidase inhibitory activities of phenyl-propanoid glycosides vanicoside A and B from Polygonumsachalinense rhizomerdquo Fitoterapia vol 77 no 6 pp 456ndash4592006
[72] P V Kiem N X Nhiem N X Cuong et al ldquoNew phenyl-propanoid esters of sucrose from Polygonum hydropiper andtheir antioxidant activityrdquo Archives of Pharmacal Research vol31 no 11 pp 1477ndash1482 2008
[73] K J Wang Y J Zhang and C R Yang ldquoAntioxidant phenolicconstituents from Fagopyrum dibotrysrdquo Journal of Ethnophar-macology vol 99 no 2 pp 259ndash264 2005
[74] N Cho J Huh H Yang et al ldquoChemical constituentsof Polygala tenuifolia roots and their inhibitory activity onlipopolysaccharide-induced nitric oxide production in BV2microgliardquo Journal of Enzyme Inhibition and Medicinal Chem-istry vol 27 no 1 pp 1ndash4 2012
[75] Q Ren C S Wu and J L Zhang ldquoUse of on-line stop-flowheart-cutting two-dimensional high performance liquid chro-matography for simultaneous determination of 12 major con-stituents in tartary buckwheat (Fagopyrum tataricum Gaertn)rdquoJournal of Chromatography A vol 1304 pp 257ndash262 2013
[76] Q Ren C S Wu Y Ren and J L Zhang ldquoCharacterizationand identification of the chemical constituents from tartarybuckwheat (Fagopyrum tataricumGaertn) by high performanceliquid chromatographyphotodiode array detectorlinear iontrap FTICR hybrid mass spectrometryrdquo Food Chemistry vol136 no 3-4 pp 1377ndash1389 2013
[77] W Li Y N Sun X T Yan et al ldquoNF-120581B inhibitory activityof sucrose fatty acid esters and related constituents fromAstragalus membranaceusrdquo Journal of Agricultural and FoodChemistry vol 61 no 29 pp 7081ndash7088 2013
[78] J T Cheng J He Y Li et al ldquoThree new sucrose fatty acid estersfrom Equisetum hiemale LrdquoHelvetica Chimica Acta vol 95 no7 pp 1158ndash1163 2012
[79] Y Jiang and P-F Tu ldquoTenuifoliose Q a new oligosaccharideester from the root of Polygala tenuifoliaWilldrdquo Journal of AsianNatural Products Research vol 5 no 4 pp 279ndash283 2003
[80] M Yoshikawa H Matsuda T Morikawa H H Xie S Naka-mura and O Muraoka ldquoPhenylethanoid oligoglycosides andacylated oligosugars with vasorelaxant activity from Cistanchetubulosardquo Bioorganic ampMedicinal Chemistry vol 14 no 22 pp7468ndash7475 2006
[81] P-F Tu H-M Shi Z-H Song Y Jiang and Y-Y ZhaoldquoChemical constituents of Cistanche sinensisrdquo Journal of AsianNatural Products Research vol 9 no 1 pp 79ndash84 2007
[82] C-L Si Y-Y Lu P-P Qin R-C Sun and Y-H Ni ldquoPhenolicextractives with chemotaxonomic significance from the bark ofPaulownia tomentosa var tomentosardquo BioResources vol 6 no4 pp 5086ndash5098 2011
[83] J Wu S Zhang Q Xiao et al ldquoPhenylethanoid and aliphaticalcohol glycosides from Acanthus ilicifoliusrdquo Phytochemistryvol 63 no 4 pp 491ndash495 2003
[84] Y Jiang and P-F Tu ldquoAnalysis of chemical constituents inCistanche speciesrdquo Journal of Chromatography A vol 1216 no11 pp 1970ndash1979 2009
[85] H Otsuka H Kuwabara and H Hoshiyama ldquoIdentification ofsucrose diesters of aryldihydronaphthalene-type lignans fromTrigonotis peduncularisand the nature of their fluorescencerdquoJournal of Natural Products vol 71 no 7 pp 1178ndash1181 2008
[86] M-R Suo J-S Yang and Q-H Liu ldquoLignan oligosaccharideesters from Eritrichium rupestrerdquo Journal of Natural Productsvol 69 no 4 pp 682ndash684 2006
[87] P-F Tu Z-H Song H-M Shi Y Jiang and Y-Y ZhaoldquoArylethyl (=phenylethanoid) glycosides and oligosaccharidefrom the stem of Cistanche tubulosardquo Helvetica Chimica Actavol 89 no 5 pp 927ndash935 2006
[88] M-H Shyr T-H Tsai and L-C Lin ldquoRossicasins A Band rosicaside F three new phenylpropanoid glycosides fromBoschniakia rossicardquoChemical and Pharmaceutical Bulletin vol54 no 2 pp 252ndash254 2006
[89] R FangNCVeitchGCKiteM J RHowes EA Porter andM S J Simmonds ldquoGlycosylated constituents of Iris fulvaandIris brevicaulisrdquoChemical amp Pharmaceutical Bulletin vol 59 no1 pp 124ndash128 2011
[90] J Fu L Zuo J Yang R Chen and D Zhang ldquoOligosaccharidepolyester and triterpenoid saponins from the roots of Polygalajaponicardquo Phytochemistry vol 69 no 7 pp 1617ndash1624 2008
[91] M-C Cheng C-Y Li H-C Ko F-N Ko Y-L Lin andT-S Wu ldquoAntidepressant principles of the roots of polygalatenuifoliardquo Journal of Natural Products vol 69 no 9 pp 1305ndash1309 2006
[92] H T Chang and P F Tu ldquoNew oligosaccharide esters andxanthone C-glucosides from Polygala telephioidesrdquo HelveticaChimica Acta vol 90 no 5 pp 944ndash950 2007
[93] J Li L Feng J Dai R Wang and T Nohara ldquoChemical con-stituents from Polygala telephioidesrdquo China Journal of ChineseMateria Medica vol 34 no 4 pp 402ndash405 2009
[94] W-P Yin T-Z Zhao and H-Y Zhang ldquoA novel oligosaccha-ride ester from Syringa pubescensrdquo Journal of Asian NaturalProducts Research vol 10 no 1 pp 95ndash100 2008
[95] M Valko D Leibfritz J Moncol M T D Cronin M Mazurand J Telser ldquoFree radicals and antioxidants in normal physio-logical functions and human diseaserdquoThe International Journalof Biochemistry amp Cell Biology vol 39 no 1 pp 44ndash84 2007
[96] D Krishnaiah R Sarbatly and R Nithyanandam ldquoA review ofthe antioxidant potential of medicinal plant speciesrdquo Food andBioproducts Processing vol 89 no 3 pp 217ndash233 2011
[97] P Liu Y Hu D-H Guo et al ldquoAntioxidant activity ofoligosaccharide ester extracted from Polygala tenuifolia roots insenescence-accelerated micerdquo Pharmaceutical Biology vol 48no 7 pp 828ndash833 2010
[98] Y Hu H-B Liao G Dai-Hong P Liu Y-Y Wang and KRahman ldquoAntidepressant-like effects of 361015840-disinapoyl sucroseon hippocampal neuronal plasticity and neurotrophic signalpathway in chronically mild stressed ratsrdquo NeurochemistryInternational vol 56 no 3 pp 461ndash465 2010
[99] Y Hu H B O Liao P Liu D-H Guo and K RahmanldquoA bioactive compound from Polygala tenuifolia regulatesefficiency of chronic stress on hypothalamic-pituitary-adrenalaxisrdquo Pharmazie vol 64 no 9 pp 605ndash608 2009
[100] A Jungbauer and SMedjakovic ldquoAnti-inflammatory propertiesof culinary herbs and spices that ameliorate the effects ofmetabolic syndromerdquoMaturitas vol 71 no 3 pp 227ndash239 2012
Evidence-Based Complementary and Alternative Medicine 23
[101] Q Xu Y Wang S Guo Z Shen and L Yang ldquoAnti-inflammatory and analgesic activity of aqueous extract of Flospopulirdquo Journal of Ethnopharmacology vol 152 no 3 pp 540ndash545 2014
[102] K S Kim D S Lee G S Bae et al ldquoThe inhibition of JNKMAPK and NF-120581B signaling by tenuifoliside A isolated fromPolygala tenuifolia in lipopolysaccharide-induced macrophagesis associated with its anti-inflammatory effectrdquo European Jour-nal of Pharmacology vol 721 no 1ndash3 pp 267ndash276 2013
[103] J-G Lee J-M Yon C Lin A Y Jung K Y Jung and S-YNamldquoCombined treatment with capsaicin and resveratrol enhancesneuroprotection against glutamate-induced toxicity in mousecerebral cortical neuronsrdquo Food and Chemical Toxicology vol50 no 11 pp 3877ndash3885 2012
[104] M L Jin S Y Park Y H Kim J-I Oh S J Lee andG Park ldquoThe neuroprotective effects of cordycepin inhibitglutamate-induced oxidative andER stress-associated apoptosisin hippocampal HT22 cellsrdquo NeuroToxicology vol 41 pp 102ndash111 2014
[105] P Liu Y Hu J Li et al ldquoProtection of SH-SY5Y neuronal cellsfrom glutamate-induced apoptosis by 36rsquo-disinapoyl sucrosea bioactive compound isolated from radix polygalardquo Journal ofBiomedicine and Biotechnology vol 2012 Article ID 728342 5pages 2012
[106] P-B Li W-L Lin Y-G Wang W Peng X-Y Cai and W-WSu ldquoAntidiabetic activities of oligosaccharides of Ophiopogonisjaponicus in experimental type 2 diabetic ratsrdquo InternationalJournal of Biological Macromolecules vol 51 no 5 pp 749ndash7552012
[107] T Liu Y M Yip L Song et al ldquoInhibiting enzymatic starchdigestion by the phenolic compound diboside A a mechanisticand in silico studyrdquo Food Research International vol 54 no 1pp 595ndash600 2013
[108] F Cote andMGHahn ldquoOligosaccharins structures and signaltransductionrdquo Plant Molecular Biology vol 26 no 5 pp 1379ndash1411 1994
[109] RACreelman and J EMullet ldquoOligosaccharins brassinolidesand jasmonates nontraditional regulators of plant growthdevelopment and gene expressionrdquo Plant Cell vol 9 no 7 pp1211ndash1223 1997
[110] L Jiao D Wan X Zhang B Li H Zhao and S LiuldquoCharacterization and immunostimulating effects on murineperitoneal macrophages of oligosaccharide isolated from Panaxginseng CAMeyerrdquo Journal of Ethnopharmacology vol 144 no3 pp 490ndash496 2012
Submit your manuscripts athttpwwwhindawicom
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Evidence-Based Complementary and Alternative Medicine
Volume 2014Hindawi Publishing Corporationhttpwwwhindawicom
16 Evidence-Based Complementary and Alternative Medicine
Table 6 Phenylpropanoid-derived pentasaccharide esters
Number Name R1 R2 R3 R4 R5 R6 Source Parts Reference160 Tenuifoliose A G D I Ac Ac Ac Polygala tenuifolia Roots [38 42]161 Tenuifoliose B G D I H Ac Ac Polygala tenuifolia Roots [42]162 Tenuifoliose C G D I H H H Polygala tenuifolia Roots [42]163 Tenuifoliose F G D U Ac Ac Ac Polygala tenuifolia Roots [42]164 Tenuifoliose G G D U Ac H Ac Polygala tenuifolia Roots [42]165 Tenuifoliose H G D G Ac Ac Ac Polygala tenuifolia Roots [38 42 79]166 Tenuifoliose I G D G Ac H Ac Polygala tenuifolia Roots [42 79]167 Tenuifoliose J G D G H Ac Ac Polygala tenuifolia Roots [42]168 Tenuifoliose K G D G H H Ac Polygala tenuifolia Roots [42]169 Tenuifoliose L G D T Ac Ac Ac Polygala tenuifolia Roots [42 79]170 Tenuifoliose M G D T Ac H Ac Polygala tenuifolia Roots [42]171 Tenuifoliose N I D I Ac Ac Ac Polygala tenuifolia Roots [42]172 Tenuifoliose O I D I H Ac Ac Polygala tenuifolia Roots [42]173 Tenuifoliose P I D I H H Ac Polygala tenuifolia Roots [42]174 Tenuifoliose Q G D T H Ac Ac Polygala tenuifolia Roots [79]175 Tenuifoliose S G D G H H H Polygala tenuifolia Roots [42]176 Tenuifoliose T G D I H H H Polygala tenuifolia Roots [42]177 Tenuifoliose V H D I Ac Ac Ac Polygala tenuifolia Roots [42]178 Tenuifoliose W I D U Ac H Ac Polygala tenuifolia Roots [42]179 Tenuifoliose X I D I H H H Polygala tenuifolia Roots [42]See Scheme 6
O
OO
O
O
O
O
OR1
OH
OH
OH
OHOH
OH
HOHO
HO
HO
OR2
R3O
CH2OH
Scheme 5
34 Anti-Inflammatory Activity Inflammation an importantbasic pathological process is a defense response of biopsywith vascular system to damage stimuli such as pathogensimpaired cells and tissues and physical and chemical factorsHowever if the process of inflammatory response cannot endnormally when cell debris and pathogens were cleared thebiological defence response will become causative factor andbring about many diseases such as diabetes cardiovasculardiseases metabolic syndrome and cancer [100 101]
Tenuifoliside A (44) from the Polygala genus exhibitedstrong anti-inflammatory effect not only by suppressing the
production of NO but also by reducing the production ofiNOS prostaglandin E2 cyclooxygenase-2 and proinflam-matory cytokines through the inhibition of the mitogen-activated protein kinases pathway and NF-120581B pathway [102]The anti-inflammatory activities of quiquesetinerviusides D(108) and E (109) from the Calamus genus were evaluated inRAW 2647 cells Both of them showed significant inhibitoryeffects against the production of LPS-stimulated NOwith theIC50values of 90ndash295120583M [70]Six disaccharide fatty acid esters (132ndash137) were iso-
lated from the Astragalus and Equisetum genera The anti-inflammatory effects of these isolated compounds have alsobeen documented The activation of NF-120581B could upregulatethe expression of proinflammatory cytokines inducible nitricoxide synthase (iNOS) and tumornecrosis factor alpha (TNF-120572) The NF-120581B inhibitory activities of compounds 132ndash137were tested in HepG2 cells stimulated with TNF-120572 All ofthese compounds could significantly restrainTNF-120572-inducedNF-120581B transcriptional activities with the IC
50values of 44ndash
247 120583M Li et al pointed out that olefinic bonds and thelength of the fatty acid moieties contributed to the NF-120581B inhibitory activity Furthermore the inhibition increasedsignificantly with the increase of the number of olefinic bondson the aliphatic moiety [77] These results may provide ascientific basis for the development of new anti-inflammatoryagents
35 Neuroprotective and Cerebral Protective Activities Aswe all know glutamate works as a major excitatory aminoacid neurotransmitter in the mammalian central nervous
Evidence-Based Complementary and Alternative Medicine 17
R6O
R2O
OR3
OR5
OR4
CH2OR1
OCH3
Rham
OO
O
OO O
O
O
O
OO
RhamO
O
OH
OH
OHOH
OH
OHOH
OHHO
HO
HO
T O-rhamnosyl-coumaroyl U O-rhamnosyl-feruloyl
Scheme 6
system and plays a crucial role in several physiological pro-cesses [103] However the accumulation of glutamate inducesdiverse acute and chronic neurodegenerative diseases suchas epilepsy ischemic stroke and Parkinsonrsquos disease aswell as Alzheimerrsquos disease [104] DISS (123) isolated fromthe Polygala genus exhibited neuroprotective effect againstglutamate-induced SH-SY5Y neuronal cell damage The invitro test demonstrated that DISS (06 6 and 60 120583molL)played a critical role in increasing cell viability controllinglactate dehydrogenase and attenuated apoptosis ranging from195 to 258 [105]
Tenuifoliside B (102) from the Polygala genus was ableto significantly shorten the coma time of KCN-inducedanoxia mice at the doses of 3 and 10mgkg and it playedan important role in ameliorating the scopolamine-inducedimpairment of performance in passive avoidance task inrats and enhancing the tremors induced by oxotremorine inmiceThese results together demonstrated that tenuifoliside Bpossessed cognitive improving and cerebral protective effects[56]
36 Antidiabetic Activity Diabetes mellitus a chronic debil-itating metabolic disease is characterized by high bloodglucose content and comprises three types termed type Itype II and gestational diabetes [106] Stachyose (19) extract(a part) from Rehmannia glutinosa obviously exhibited theactivity of downregulating fasting plasma glucose level andpartially keeping from hyperglycemia induced by adrenalineand glucose without obvious dose-dependent effect Otherthan that in vivo tests in rats induced by alloxan revealed
that stachyose extract at the dose of 200mgkg significantlydecreased blood-sugar level [15]
Diboside A lapathosides C and D vanicosides A andB and hydropiperoside were isolated from the FagopyrumPolygonum and Persicaria genera belonging to the Polygo-naceae family Diboside A (116) could potentially inhibit 120572-amylase activity with an IC
50of 269 120583M and thus retard the
starch digestion rate which is helpful for diabetic individualsin controlling blood sugar level [107] Lapathoside D (38)exerted stronger activity of 120572-glucosidase inhibition with anIC50
value of 0113mM than acarbose which was chosen asa positive drug for the treatment of type II diabetes [43]Vanicoside B (111) was reported to have higher 120573-glucosidaseinhibitory activity with an IC
50of 505 120583M than vanicoside A
(110) with an IC50of 599 120583M because of the acetyl moiety of
the latter possibly decreasing inhibitory activity of vanicosideA [71]
Fujimoto et al investigated the inhibitory effects ofmumeoses FndashO (83ndash92) from the Prunus genus on aldosereductase and discovered that caffeoyl groups are crucialfor the inhibitory effect on aldose reductase And thusmumeoses F G H J K L M and N (IC
50= 22ndash77120583M) with
a coumaroyl group and acetyl groups inhibited moderatelyaldose reductase from reducing glucose to sorbitol whichis associated with the chronic complications of diabetes [6364]
37 Elicitors and Regulators Oligosaccharides are quitepropitious for encoding biological information because ofdiverse monosaccharide units and complex molecular struc-tures and they are therefore first described as biological
18 Evidence-Based Complementary and Alternative Medicine
181 H
H
H
H
H
H
H
H
H H
H
H
H
H
H
H
H H
HH
Benzyl
Benzyl
Benzyl
182
183
184 Ac
Ac
Ac
Ac
Ac
Ac
Ac
Ac
Ac
Ac
185
186
187
188
189
R1 R2 R3
R1 R2 R3 R4
OCH3
R3OH2C OR2
OR1
OR1
O
O
O
O O
OOO
O
OO
O
OH
OH
OH OH
OH
O O
O
O
OH
HO
OH
OH OHOH
OH
OH
OHHO
HO
OH
OH
HO
CH2OH
CH2OH
CH2OH
CH2OH
C
R2O
R3O
CH2OR4
CH2CH2 CH2CH2CH2CH2CH3
CH3
CH3
191190 192
193
O
C C
O
OO
OO
OO
OO
O O
O
O
O
O
O
O
OH
OH
OHHO
HO
HOOH
OH
OH
OH
HO
OH
OH
OH
OH
HO
HO
C C
R998400O
R998400
Figure 6
signals in plants [108] Oligosaccharides from the cell wallfragments of plants and fungi are powerful signal moleculessuch as the elicitors of plant defence response and theregulators of plant growth and they are capable of exertingbiological activities at exceedingly low concentrations [109]Heptasaccharide (HS) (15) and octasaccharide (OS) (16) iso-lated from the Paris genus possessed plant growth-regulatory
activities [29 30]The two oligosaccharides significantly pro-moted the proliferation of Paris polyphylla var yunnanensisroots at the doses of 25ndash20mgL The octasaccharide hadthe most obvious effect on the growth of Panax japonicusvar major hairy roots at a dose of 30mgL while the otherhad the most positive effect on saponin accumulation ofPanax japonicus var major hairy roots at a dose of 10mgL
Evidence-Based Complementary and Alternative Medicine 19
[29] Similarly Zhou et al evaluated the stimulating effectsof HS and OS on the root growth and saponin productionof Panax ginseng hairy roots which were induced from theplant roots infected withAgrobacterium rhizogenes strain A4The results showed that there was a maximum effect on thehairy roots growth and saponin accumulation on day 10Compared with control group the root biomass dry weightwas increased by more than 17-fold while the total saponincontent of roots increased by more than 1-fold when thesetwo oligosaccharides were added to the hairy root at a dose of30mgL [30] The above data illustrate that HS and OS couldserve as the plant growth-regulators not only in their originalspecies but also in others
38 Immunopotentiating Activity Macrophages are impor-tant targets of investigations on cytophagy cellular immunityand molecular immunology Therefore they are deemedto play a vital role in host defense comprising phagocy-tosis proteolytic processing pathogenic agent apoptosiscytokines production and foreign antigens presentation[110] The water-extracted oligosaccharides from Panax gin-seng (WGOS) exhibited better immunopotentiating activ-ity by increasing phagocytic function of macrophages andpromoting NO TNF-120572 and reactive oxygen species pro-duction [110] In addition Wan et al have obtained malto-oligosaccharides (17 119899 = 3sim8) and three oligosaccharides (213 14) from the Panax ginseng roots The in vitro bioassaypointed out thatWGOS could serve as efficacious stimulatorsof B and T lymphocytes [28] These studies provided enlight-enment that the mixture of oligosaccharides from Chineseherbalmedicine exhibits significant effect on immune system
39 Others Acetylcholinesterase (AChE) inhibitors showgood therapeutic effects onmyasthenia gravis glaucoma andAlzheimerrsquos disease through reversible enzyme inhibitionso as to increase the accumulation of acetylcholine in thesynapse and then promote and prolong the function ofacetylcholine Vanicoside B (111) showed AChE inhibitoryactivity with an IC
50of 0062mM while hydropiperoside
(42) and lapathosides C (115) and D (38) just exhibited weakenzyme inhibitory activity [43]
Wang et al has explored low molecular mass carbohy-drate polymer from Panax ginseng roots and obtained 30ethanol elution (PGO)which included peptides and oligosac-charides (17 119899 = 0sim5) identified as maltose maltotriosemaltotetraose maltopentaose maltohexaose and maltohep-taose Pharmacological experiments revealed that PGO couldsignificantly enhance the memory in scopolamine-inducedmemory deficit rats [27]
Cistanoside F (129) and kankanose (150) were isolatedfrom the Cistanche Paulownia and Acanthus genera Phar-macological experiments showed that cistanoside F andkankanose significantly exhibited vasorelaxant effects on thenoradrenaline-induced contraction of thoracic aorta fromrats [80]
4 Conclusion
Traditional Chinese medicine from natural kingdom playsan indelible role in the treatment of human diseases andit has aroused the attention of those who have engagedin medicinal pharmaceutical chemistry Therefore scientistshave made great contributions day after day to investigate thevalid chemicals from traditional Chinese medicines In thepast decades about 193 oligosaccharides and their esters havebeen identified from traditional Chinese medicinal plantsOn the one hand only a few oligosaccharides and theirmixtures were investigated and just exhibited antidepres-sant antineoplastic antidiabetic plant growth-regulatoryimmunopotentiating and enhancedmemory activitiesMoreexploratory work is still needed to excavate biological andpharmacological activities of oligosaccharides On the otherhand oligosaccharide esters exhibited multi-advantageousactivities Bioassays have revealed that antioxidant cytotoxicantineoplastic and anti-inflammatory activities are the mostnotable bioactivities Of course to search for the naturalproducts with these activities is a hotpot in the contemporarydrug research Oligosaccharide esters provide a vast treasuretrove for medical researchers After considering the currentstudies it should be taken as future directions to makemore mechanism of action studies and clinical trials tofurther evaluate its potential as new drugs Moreover thestructure-activity relationships discussed in this review willprovide reference information for further exploring theirrelationships and continually discovering the new bioactiveoligosaccharide esters
Conflict of Interests
The authors declare that there is no conflict of interestsregarding the publication of this paper
References
[1] X D Yang L J Zhang B Liang L Z Xu and S L YangldquoOligosaccharide esters isolated from plants of PolygalaceaerdquoChinese Traditional and Herbal Drugs vol 33 no 10 pp 954ndash958 2002
[2] N Ogwuru and M Adamczeski ldquoBioactive natural productsderived from Polygonum species of plants their structures andmechanisms of actionrdquo Studies in Natural Products Chemistryvol 22 pp 607ndash642 2000
[3] S Kobayashi T Miyase and H Noguchi ldquoPolyphenolic glyco-sides and oligosaccharide multiesters from the roots of Polygaladalmaisianardquo Journal of Natural Products vol 65 no 3 pp 319ndash328 2002
[4] M Takasaki S Kuroki M Kozuka and T Konoshima ldquoNewphenylpropanoid esters of sucrose from Polygonum lapathi-foliumrdquo Journal of Natural Products vol 64 no 10 pp 1305ndash1308 2001
[5] M L Zimmermann and A T Sneden ldquoVanicosides A and Bprotein kinase C inhibitors from Polygonum pensylvanicumrdquoJournal of Natural Products vol 57 no 2 pp 236ndash242 1994
[6] M Takasaki T Konoshima S Kuroki H Tokuda and HNishino ldquoCancer chemopreventive activity of phenylpropanoid
20 Evidence-Based Complementary and Alternative Medicine
esters of sucrose vanicoside B and lapathoside A from Poly-gonum lapathifoliumrdquo Cancer Letters vol 173 no 2 pp 133ndash138 2001
[7] Q Fu T Liang Z Y Li et al ldquoSeparation of carbohydrates usinghydrophilic interaction liquid chromatographyrdquo CarbohydrateResearch vol 379 pp 13ndash17 2013
[8] M F Mrozek D Zhang and D Ben-Amotz ldquoOligosaccharideidentification and mixture quantification using Raman spec-troscopy and chemometric analysisrdquo Carbohydrate Researchvol 339 no 1 pp 141ndash145 2004
[9] G S Armstrong and B Bendiak ldquoHigh-resolution four-dimen-sional carbon-correlated 1H-1H ROESY experiments employ-ing isotags and the filter diagonalization method for effectiveassignment of glycosidic linkages in oligosaccharidesrdquo Journalof Magnetic Resonance vol 181 no 1 pp 79ndash88 2006
[10] G S Armstrong V A Mandelshtam A J Shaka and BBendiak ldquoRapid high-resolution four-dimensional NMR spec-troscopy using the filter diagonalization method and its advan-tages for detailed structural elucidation of oligosaccharidesrdquoJournal of Magnetic Resonance vol 173 no 1 pp 160ndash168 2005
[11] H-M Tseng S Gattolin J Pritchard H J Newbury and DA Barrett ldquoAnalysis of mono- di- and oligosaccharides by CEusing a two-stage derivatization method and LIF detectionrdquoElectrophoresis vol 30 no 8 pp 1399ndash1405 2009
[12] N Li X Li B L Hou and D L Meng ldquoNew disaccharosidefrom Camptosorus sibiricus Ruprrdquo Natural Product Researchvol 22 no 15 pp 1379ndash1383 2008
[13] Z Zhang D Wang Y Zhao H Gao Y-H Hu and J-FHu ldquoFructose-derived carbohydrates from Alisma orientalisrdquoNatural Product Research vol 23 no 11 pp 1013ndash1020 2009
[14] X Yang Y Zhao N He and K D Croft ldquoIsolation char-acterization and immunological effects of 120572-galacto-oligo-saccharides from a new source the herb Lycopus lucidus TurczrdquoJournal of Agricultural and Food Chemistry vol 58 no 14 pp8253ndash8258 2010
[15] R X Zhang Z P Jia L Y Kong et al ldquoStachyose extractfrom Rehmannia glutinosa Libosch to lower plasma glucose innormal and diabetic rats by oral administrationrdquo Pharmazievol 59 no 7 pp 552ndash556 2004
[16] R Zhang Y Zhao Y Sun X Lu and X Yang ldquoIsolationcharacterization and hepatoprotective effects of the raffinosefamily oligosaccharides from Rehmannia glutinosa liboschrdquoJournal of Agricultural and Food Chemistry vol 61 no 32 pp7786ndash7793 2013
[17] H Li F Song Z Zheng Z Liu and S Liu ldquoCharacterization ofsaccharides and phenolic acids in the Chinese herb Tanshen byESI-FT-ICR-MS and HPLCrdquo Journal of Mass Spectrometry vol43 no 11 pp 1545ndash1552 2008
[18] J E Deng J Zhang XM ChenW Ke and G Y Tian ldquoStudieson the physicochemical properties structure and antitumoractivity of an oligosaccharide homologue SnS-2 from the root ofScrophularia ningpoensis Hemslrdquo Chinese Journal of Chemistryvol 22 no 5 pp 492ndash497 2004
[19] S C Chou LM Chuang and S S Lee ldquoHypoglycemic constit-uents of gynura divaricata subsp formosanardquo Natural ProductCommunications vol 7 no 2 pp 221ndash222 2012
[20] F Feng L-L Wang X-P Lai Y-B Li Z-M Cao and Y-J Zhou ldquoStudy on oligosaccharides from Morinda officinalisrdquoJournal of Chinese Medicinal Materials vol 35 no 8 pp 1259ndash1262 2012
[21] Y F Li Z H Gong M Yang Y M Zhao and Z P Luo ldquoInhibi-tion of the oligosaccharides extracted fromMorinda officinalis
a Chinese traditional herbal medicine on the corticosteroneinduced apoptosis in PC12 cellsrdquo Life Sciences vol 72 no 8 pp933ndash942 2003
[22] Y-F Li Y-Q Liu M Yang et al ldquoThe cytoprotective effect ofinulin-type hexasaccharide extracted from Morinda officinalison PC12 cells against the lesion induced by corticosteronerdquo LifeSciences vol 75 no 13 pp 1531ndash1538 2004
[23] D N Olennikov L M Tankhaeva and A V Rokhin ldquoGlu-cofructans from Saussurea lappa rootsrdquo Chemistry of NaturalCompounds vol 47 no 3 pp 339ndash342 2011
[24] S K Hyun H A Jung B S Min J H Jung and J S ChoildquoIsolation of phenolics nucleosides saccharides and an alkaloidfrom the root of Aralia cordatardquo Natural Product Sciences vol16 no 1 pp 20ndash25 2010
[25] Z J Xu C W Lin and M F Liao ldquoStructure analysis of a newoligosaccharides BROS from Blumea ripariardquo Chinese Journalof Organic Chemistry vol 31 no 11 pp 1811ndash1819 2011
[26] Z J Xu C W Lin and Y Shi ldquoIsolation and structuredetermination of a new oligosaccharide from Blume ripariardquoJournal of Medicinal Plants Research vol 5 no 14 pp 2956ndash2962 2011
[27] Y Wang R Z Jiang G R Li et al ldquoStructural and enhancedmemory activity studies of extracts from Panax ginseng rootrdquoFood Chemistry vol 119 no 3 pp 969ndash973 2010
[28] DWan L Jiao H Yang and S Liu ldquoStructural characterizationand immunological activities of the water-soluble oligosaccha-rides isolated from thePanax ginseng rootsrdquoPlanta vol 235 no6 pp 1289ndash1297 2012
[29] L G Zhou C Z Yang J Q Li S L Wang and J Y WuldquoHeptasaccharide and octasaccharide isolated from Paris pol-yphylla var yunnanensis and their plant growth-regulatoryactivityrdquo Plant Science vol 165 no 3 pp 571ndash575 2003
[30] L G Zhou X D Cao R F Zhang Y L Peng S J Zhao andJ Y Wu ldquoStimulation of saponin production in Panax ginsenghairy roots by two oligosaccharides from Paris polyphylla varyunnanensisrdquo Biotechnology Letters vol 29 no 4 pp 631ndash6342007
[31] M Vanhaecke W van den Ende E Lescrinier and N Dyu-bankova ldquoIsolation and characterization of a pentasaccharidefrom Stellaria mediardquo Journal of Natural Products vol 71 no 11pp 1833ndash1836 2008
[32] J Feng and W Zhao ldquoComplete 1Hand 13C NMR assignmentsof four new oligosaccharides and two new glycosides fromPeriploca forrestiirdquoMagnetic Resonance in Chemistry vol 47 no8 pp 701ndash705 2009
[33] J Q Feng R J Zhang Y Zhou et al ldquoImmunosuppressive preg-nane glycosides from Periploca sepium and Periploca forrestiirdquoPhytochemistry vol 69 no 15 pp 2716ndash2723 2008
[34] X H Long R Xu Y H Zhang X H Tan andQ Y Sun ldquoA newoligosaccharide from Periploca calophyllardquo Zhongguo ZhongyaoZazhi vol 37 no 2 pp 226ndash229 2012
[35] L Wang Z-Q Yin Y Wang X-Q Zhang Y-L Li and W-CYe ldquoPerisesaccharides A-E new oligosaccharides from the rootbarks ofPeriploca sepiumrdquoPlantaMedica vol 76 no 9 pp 909ndash915 2010
[36] T Lei L Zhang H-Y Jiang Y Hu A-H Hong and Y-Z CenldquoA new pregnane glycoside and oligosaccharide from Parabar-ium huaitingiirdquo Journal of Asian Natural Products Research vol13 no 11 pp 1030ndash1035 2011
[37] J Li Y Jiang and P F Tu ldquoTricornoses A-L oligosaccharidemulti-esters from the roots of Polygala tricornisrdquo Journal ofNatural Products vol 68 no 5 pp 739ndash744 2005
Evidence-Based Complementary and Alternative Medicine 21
[38] H H Tu P Liu L Mu et al ldquoStudy on antidepressant com-ponents of sucrose ester from Polygala tenuifoliardquo ZhongguoZhongyao Zazhi vol 33 no 11 pp 1278ndash1280 2008
[39] G M She Y Y Ba Y Liu H Lv W Wang and R B ShildquoAbsorbable phenylpropenoyl sucroses from Polygala tenuifo-liardquoMolecules vol 16 no 7 pp 5507ndash5513 2011
[40] J Yong and P F Tu ldquoStudies on the chemical constituents inroot bark of Polygala tenuifolia (II)rdquo China Journal of ChineseMateria Medica vol 29 no 8 pp 751ndash753 2004
[41] M Ono C Takamura F Sugita et al ldquoTwo new steroidglycosides and a new sesquiterpenoid glycoside from theunderground parts of Trillium kamtschaticumrdquo Chemical andPharmaceutical Bulletin vol 55 no 4 pp 551ndash556 2007
[42] Y Ling Z Li M Chen Z Sun M Fan and C HuangldquoAnalysis and detection of the chemical constituents of RadixPolygalae and their metabolites in rats after oral administrationby ultra high-performance liquid chromatography coupledwith electrospray ionization quadrupole time-of-flight tandemmass spectrometryrdquo Journal of Pharmaceutical and BiomedicalAnalysis vol 85 pp 1ndash13 2013
[43] P Fan L Terrier A-E Hay A Marston and K HostettmannldquoAntioxidant and enzyme inhibition activities and chemicalprofiles ofPolygonum sachalinensis FSchmidt exMaxim (Polyg-onaceae)rdquo Fitoterapia vol 81 no 2 pp 124ndash131 2010
[44] L J Zhang C C Liao H C Huang Y C Shen L M Yangand Y H Kuo ldquoAntioxidant phenylpropanoid glycosides fromSmilax bracteatardquo Phytochemistry vol 69 no 6 pp 1398ndash14042008
[45] L L Yan W Y Gao Y J Zhang and Y Wang ldquoA new phenyl-propanoid glycosides from Paris polyphylla var yunnanensisrdquoFitoterapia vol 79 no 4 pp 306ndash307 2008
[46] Y H Kuo Y W Hsu C C Liaw J K Lee H C Huang andL M Y Kuo ldquoCytotoxic phenylpropanoid glycosides from thestems of Smilax chinardquo Journal of Natural Products vol 68 no10 pp 1475ndash1478 2005
[47] W-X Wang T-X Li H Ma J-F Zhang and A-Q JialdquoTumoral cytotoxic and antioxidative phenylpropanoid glyco-sides in Smilax riparia A DCrdquo Journal of Ethnopharmacologyvol 149 no 2 pp 527ndash532 2013
[48] N X Nhiem P vanKiem C vanMinh et al ldquoPhenylpropanoidglycosides fromHeterosmilax erythrantha and their antioxidantactivityrdquo Archives of Pharmacal Research vol 32 no 10 pp1373ndash1377 2009
[49] Y Wang W Y Gao T J Zhang and Y Q Guo ldquoA novelphenylpropanoid glycosides and a new derivation of phenolicglycoside from Paris Polyphylla var yunnanensisrdquo ChineseChemical Letters vol 18 no 5 pp 548ndash550 2007
[50] J-Y Zhang Y-Z Wang Y-L Zhao et al ldquoPhytochemicals andbioactivities of Paris speciesrdquo Journal of Asian Natural ProductsResearch vol 13 no 7 pp 670ndash681 2011
[51] N H N Hashim F Abas K Shaari and N H Lajis ldquoLC-DAD-ESIMSMS characterization of antioxidant and anti-cholinesterase constituents present in the active fraction fromPersicaria hydropiperrdquo LWT Food Science and Technology vol46 no 2 pp 468ndash476 2012
[52] PH FanA EHayAMarstonHX Lou andKHostettmannldquoChemical variability of the invasive neophytes Polygonumcuspidatum Sieb and Zucc and Polygonum sachalinensis FSchmidt ex Maximrdquo Biochemical Systematics and Ecology vol37 no 1 pp 24ndash34 2009
[53] P Liu Y Hu D H Guo et al ldquoPotential antidepressantproperties of Radix Polygalae (Yuan Zhi)rdquo Phytomedicine vol17 no 10 pp 794ndash799 2010
[54] J F Wu S B Chen S L Chen and P F Tu ldquoThe chemical con-stituents of Polygala hongkongensisHemslrdquoActa PharmaceuticaSinica vol 42 no 7 pp 757ndash761 2007
[55] Y Song Y Jiang D Bi X Tian L Liang and P Tu ldquoChemicalconstituents from n-butanol extract of aerial part of Polygalasibiricardquo Zhongguo Zhongyao Zazhi vol 37 no 4 pp 471ndash4742012
[56] Y Ikeya S Takeda M Tunakawa et al ldquoCognitive improvingand cerebral protective effects of acylated oligosaccharides inPolygala tenuifoliardquo Biological and Pharmaceutical Bulletin vol27 no 7 pp 1081ndash1085 2004
[57] C J Zheng C L Hu X Q Ma C Peng H Zhang and L PQin ldquoCytotoxic phenylpropanoid glycosides from Fagopyrumtataricum (L) Gaertnrdquo Food Chemistry vol 132 no 1 pp 433ndash438 2012
[58] X Li Y F Zhang L Yang et al ldquoChemical profiling ofconstituents of Smilacis glabrae using ultra-high pressure liquidchromatography coupled with LTQ orbitrap mass spectrome-tryrdquo Natural Product Communications vol 7 no 2 pp 181ndash1842012
[59] T-T Sun D-W Zhang Y Han F-Y Dong andWWang ldquoSmi-lasides M and N two new phenylpropanoid glycosides fromSmilax ripariardquo Journal of Asian Natural Products Research vol14 no 2 pp 165ndash170 2012
[60] J Li X Bi G Zheng Y Hitoshi T Ikeda and T NoharaldquoSteroidal glycosides and aromatic compounds from Smilaxripariardquo Chemical amp Pharmaceutical Bulletin vol 54 no 10 pp1451ndash1454 2006
[61] N Wang X Yao R Ishii and S Kitanaka ldquoBioactive sucroseesters from Bidens parviflorardquo Phytochemistry vol 62 no 5 pp741ndash746 2003
[62] S Nakamura K Fujimoto T Matsumoto et al ldquoAcylatedsucroses and acylated quinic acids analogs from the flower budsof Prunus mume and their inhibitory effect on melanogenesisrdquoPhytochemistry vol 92 pp 128ndash136 2013
[63] K Fujimoto SNakamura TMatsumoto et al ldquoMedicinal flow-ers XXXVIII Structures of acylated sucroses and inhibitoryeffects of constituents on aldose reducatase from the flower budsofPrunusmumerdquoChemical and Pharmaceutical Bulletin vol 61no 4 pp 445ndash451 2013
[64] S Nakamura K Fujimoto T Matsumoto et al ldquoStructuresof acylated sucroses and an acylated flavonol glycoside andinhibitory effects of constituents on aldose reductase from theflower buds of Prunus mumerdquo Journal of Natural Medicines vol67 no 4 pp 799ndash806 2013
[65] L-B Dong J He X-Y Li et al ldquoChemical constituents fromthe aerial parts of Musella lasiocarpardquo Natural Products andBioprospecting vol 1 no 1 pp 41ndash47 2011
[66] Y Xiong K Z Deng Y Q Guo W Y Gao and T J ZhangldquoNew chemical constituents from the rhizomes of Sparganiumstoloniferumrdquo Archives of Pharmacal Research vol 32 no 5 pp717ndash720 2009
[67] Y Xiong K-Z Deng Y-Q Guo W-Y Gao and T-J ZhangldquoTwo new sucrose esters from Sparganium stoloniferumrdquo Jour-nal of Asian Natural Products Research vol 10 no 5 pp 425ndash428 2008
[68] B Chen N L Wang J H Huang and X S Yao ldquoIridoidand phenylpropanoid glycosides from Scrophularia ningpoensis
22 Evidence-Based Complementary and Alternative Medicine
Hemslrdquo Asian Journal of Traditional Medicines vol 2 no 3 pp119ndash123 2007
[69] H Chen Y Z Zhou L Qiao et al ldquoTwo new compounds fromCynanchum amplexicaulerdquo Journal of Asian Natural ProductsResearch vol 10 no 3 pp 248ndash251 2008
[70] C-L Chang L-J Zhang R Y Chen et al ldquoAntioxidant andanti-inflammatory phenylpropanoid derivatives from Calamusquiquesetinerviusrdquo Journal of Natural Products vol 73 no 9 pp1482ndash1488 2010
[71] Y Kawai H Kumagai H Kurihara K Yamazaki R Sawanoand N Inoue ldquo120573-Glucosidase inhibitory activities of phenyl-propanoid glycosides vanicoside A and B from Polygonumsachalinense rhizomerdquo Fitoterapia vol 77 no 6 pp 456ndash4592006
[72] P V Kiem N X Nhiem N X Cuong et al ldquoNew phenyl-propanoid esters of sucrose from Polygonum hydropiper andtheir antioxidant activityrdquo Archives of Pharmacal Research vol31 no 11 pp 1477ndash1482 2008
[73] K J Wang Y J Zhang and C R Yang ldquoAntioxidant phenolicconstituents from Fagopyrum dibotrysrdquo Journal of Ethnophar-macology vol 99 no 2 pp 259ndash264 2005
[74] N Cho J Huh H Yang et al ldquoChemical constituentsof Polygala tenuifolia roots and their inhibitory activity onlipopolysaccharide-induced nitric oxide production in BV2microgliardquo Journal of Enzyme Inhibition and Medicinal Chem-istry vol 27 no 1 pp 1ndash4 2012
[75] Q Ren C S Wu and J L Zhang ldquoUse of on-line stop-flowheart-cutting two-dimensional high performance liquid chro-matography for simultaneous determination of 12 major con-stituents in tartary buckwheat (Fagopyrum tataricum Gaertn)rdquoJournal of Chromatography A vol 1304 pp 257ndash262 2013
[76] Q Ren C S Wu Y Ren and J L Zhang ldquoCharacterizationand identification of the chemical constituents from tartarybuckwheat (Fagopyrum tataricumGaertn) by high performanceliquid chromatographyphotodiode array detectorlinear iontrap FTICR hybrid mass spectrometryrdquo Food Chemistry vol136 no 3-4 pp 1377ndash1389 2013
[77] W Li Y N Sun X T Yan et al ldquoNF-120581B inhibitory activityof sucrose fatty acid esters and related constituents fromAstragalus membranaceusrdquo Journal of Agricultural and FoodChemistry vol 61 no 29 pp 7081ndash7088 2013
[78] J T Cheng J He Y Li et al ldquoThree new sucrose fatty acid estersfrom Equisetum hiemale LrdquoHelvetica Chimica Acta vol 95 no7 pp 1158ndash1163 2012
[79] Y Jiang and P-F Tu ldquoTenuifoliose Q a new oligosaccharideester from the root of Polygala tenuifoliaWilldrdquo Journal of AsianNatural Products Research vol 5 no 4 pp 279ndash283 2003
[80] M Yoshikawa H Matsuda T Morikawa H H Xie S Naka-mura and O Muraoka ldquoPhenylethanoid oligoglycosides andacylated oligosugars with vasorelaxant activity from Cistanchetubulosardquo Bioorganic ampMedicinal Chemistry vol 14 no 22 pp7468ndash7475 2006
[81] P-F Tu H-M Shi Z-H Song Y Jiang and Y-Y ZhaoldquoChemical constituents of Cistanche sinensisrdquo Journal of AsianNatural Products Research vol 9 no 1 pp 79ndash84 2007
[82] C-L Si Y-Y Lu P-P Qin R-C Sun and Y-H Ni ldquoPhenolicextractives with chemotaxonomic significance from the bark ofPaulownia tomentosa var tomentosardquo BioResources vol 6 no4 pp 5086ndash5098 2011
[83] J Wu S Zhang Q Xiao et al ldquoPhenylethanoid and aliphaticalcohol glycosides from Acanthus ilicifoliusrdquo Phytochemistryvol 63 no 4 pp 491ndash495 2003
[84] Y Jiang and P-F Tu ldquoAnalysis of chemical constituents inCistanche speciesrdquo Journal of Chromatography A vol 1216 no11 pp 1970ndash1979 2009
[85] H Otsuka H Kuwabara and H Hoshiyama ldquoIdentification ofsucrose diesters of aryldihydronaphthalene-type lignans fromTrigonotis peduncularisand the nature of their fluorescencerdquoJournal of Natural Products vol 71 no 7 pp 1178ndash1181 2008
[86] M-R Suo J-S Yang and Q-H Liu ldquoLignan oligosaccharideesters from Eritrichium rupestrerdquo Journal of Natural Productsvol 69 no 4 pp 682ndash684 2006
[87] P-F Tu Z-H Song H-M Shi Y Jiang and Y-Y ZhaoldquoArylethyl (=phenylethanoid) glycosides and oligosaccharidefrom the stem of Cistanche tubulosardquo Helvetica Chimica Actavol 89 no 5 pp 927ndash935 2006
[88] M-H Shyr T-H Tsai and L-C Lin ldquoRossicasins A Band rosicaside F three new phenylpropanoid glycosides fromBoschniakia rossicardquoChemical and Pharmaceutical Bulletin vol54 no 2 pp 252ndash254 2006
[89] R FangNCVeitchGCKiteM J RHowes EA Porter andM S J Simmonds ldquoGlycosylated constituents of Iris fulvaandIris brevicaulisrdquoChemical amp Pharmaceutical Bulletin vol 59 no1 pp 124ndash128 2011
[90] J Fu L Zuo J Yang R Chen and D Zhang ldquoOligosaccharidepolyester and triterpenoid saponins from the roots of Polygalajaponicardquo Phytochemistry vol 69 no 7 pp 1617ndash1624 2008
[91] M-C Cheng C-Y Li H-C Ko F-N Ko Y-L Lin andT-S Wu ldquoAntidepressant principles of the roots of polygalatenuifoliardquo Journal of Natural Products vol 69 no 9 pp 1305ndash1309 2006
[92] H T Chang and P F Tu ldquoNew oligosaccharide esters andxanthone C-glucosides from Polygala telephioidesrdquo HelveticaChimica Acta vol 90 no 5 pp 944ndash950 2007
[93] J Li L Feng J Dai R Wang and T Nohara ldquoChemical con-stituents from Polygala telephioidesrdquo China Journal of ChineseMateria Medica vol 34 no 4 pp 402ndash405 2009
[94] W-P Yin T-Z Zhao and H-Y Zhang ldquoA novel oligosaccha-ride ester from Syringa pubescensrdquo Journal of Asian NaturalProducts Research vol 10 no 1 pp 95ndash100 2008
[95] M Valko D Leibfritz J Moncol M T D Cronin M Mazurand J Telser ldquoFree radicals and antioxidants in normal physio-logical functions and human diseaserdquoThe International Journalof Biochemistry amp Cell Biology vol 39 no 1 pp 44ndash84 2007
[96] D Krishnaiah R Sarbatly and R Nithyanandam ldquoA review ofthe antioxidant potential of medicinal plant speciesrdquo Food andBioproducts Processing vol 89 no 3 pp 217ndash233 2011
[97] P Liu Y Hu D-H Guo et al ldquoAntioxidant activity ofoligosaccharide ester extracted from Polygala tenuifolia roots insenescence-accelerated micerdquo Pharmaceutical Biology vol 48no 7 pp 828ndash833 2010
[98] Y Hu H-B Liao G Dai-Hong P Liu Y-Y Wang and KRahman ldquoAntidepressant-like effects of 361015840-disinapoyl sucroseon hippocampal neuronal plasticity and neurotrophic signalpathway in chronically mild stressed ratsrdquo NeurochemistryInternational vol 56 no 3 pp 461ndash465 2010
[99] Y Hu H B O Liao P Liu D-H Guo and K RahmanldquoA bioactive compound from Polygala tenuifolia regulatesefficiency of chronic stress on hypothalamic-pituitary-adrenalaxisrdquo Pharmazie vol 64 no 9 pp 605ndash608 2009
[100] A Jungbauer and SMedjakovic ldquoAnti-inflammatory propertiesof culinary herbs and spices that ameliorate the effects ofmetabolic syndromerdquoMaturitas vol 71 no 3 pp 227ndash239 2012
Evidence-Based Complementary and Alternative Medicine 23
[101] Q Xu Y Wang S Guo Z Shen and L Yang ldquoAnti-inflammatory and analgesic activity of aqueous extract of Flospopulirdquo Journal of Ethnopharmacology vol 152 no 3 pp 540ndash545 2014
[102] K S Kim D S Lee G S Bae et al ldquoThe inhibition of JNKMAPK and NF-120581B signaling by tenuifoliside A isolated fromPolygala tenuifolia in lipopolysaccharide-induced macrophagesis associated with its anti-inflammatory effectrdquo European Jour-nal of Pharmacology vol 721 no 1ndash3 pp 267ndash276 2013
[103] J-G Lee J-M Yon C Lin A Y Jung K Y Jung and S-YNamldquoCombined treatment with capsaicin and resveratrol enhancesneuroprotection against glutamate-induced toxicity in mousecerebral cortical neuronsrdquo Food and Chemical Toxicology vol50 no 11 pp 3877ndash3885 2012
[104] M L Jin S Y Park Y H Kim J-I Oh S J Lee andG Park ldquoThe neuroprotective effects of cordycepin inhibitglutamate-induced oxidative andER stress-associated apoptosisin hippocampal HT22 cellsrdquo NeuroToxicology vol 41 pp 102ndash111 2014
[105] P Liu Y Hu J Li et al ldquoProtection of SH-SY5Y neuronal cellsfrom glutamate-induced apoptosis by 36rsquo-disinapoyl sucrosea bioactive compound isolated from radix polygalardquo Journal ofBiomedicine and Biotechnology vol 2012 Article ID 728342 5pages 2012
[106] P-B Li W-L Lin Y-G Wang W Peng X-Y Cai and W-WSu ldquoAntidiabetic activities of oligosaccharides of Ophiopogonisjaponicus in experimental type 2 diabetic ratsrdquo InternationalJournal of Biological Macromolecules vol 51 no 5 pp 749ndash7552012
[107] T Liu Y M Yip L Song et al ldquoInhibiting enzymatic starchdigestion by the phenolic compound diboside A a mechanisticand in silico studyrdquo Food Research International vol 54 no 1pp 595ndash600 2013
[108] F Cote andMGHahn ldquoOligosaccharins structures and signaltransductionrdquo Plant Molecular Biology vol 26 no 5 pp 1379ndash1411 1994
[109] RACreelman and J EMullet ldquoOligosaccharins brassinolidesand jasmonates nontraditional regulators of plant growthdevelopment and gene expressionrdquo Plant Cell vol 9 no 7 pp1211ndash1223 1997
[110] L Jiao D Wan X Zhang B Li H Zhao and S LiuldquoCharacterization and immunostimulating effects on murineperitoneal macrophages of oligosaccharide isolated from Panaxginseng CAMeyerrdquo Journal of Ethnopharmacology vol 144 no3 pp 490ndash496 2012
Submit your manuscripts athttpwwwhindawicom
Stem CellsInternational
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
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Disease Markers
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OncologyJournal of
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Oxidative Medicine and Cellular Longevity
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PPAR Research
The Scientific World JournalHindawi Publishing Corporation httpwwwhindawicom Volume 2014
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Journal of
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Computational and Mathematical Methods in Medicine
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Research and TreatmentAIDS
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Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Parkinsonrsquos Disease
Evidence-Based Complementary and Alternative Medicine
Volume 2014Hindawi Publishing Corporationhttpwwwhindawicom
Evidence-Based Complementary and Alternative Medicine 17
R6O
R2O
OR3
OR5
OR4
CH2OR1
OCH3
Rham
OO
O
OO O
O
O
O
OO
RhamO
O
OH
OH
OHOH
OH
OHOH
OHHO
HO
HO
T O-rhamnosyl-coumaroyl U O-rhamnosyl-feruloyl
Scheme 6
system and plays a crucial role in several physiological pro-cesses [103] However the accumulation of glutamate inducesdiverse acute and chronic neurodegenerative diseases suchas epilepsy ischemic stroke and Parkinsonrsquos disease aswell as Alzheimerrsquos disease [104] DISS (123) isolated fromthe Polygala genus exhibited neuroprotective effect againstglutamate-induced SH-SY5Y neuronal cell damage The invitro test demonstrated that DISS (06 6 and 60 120583molL)played a critical role in increasing cell viability controllinglactate dehydrogenase and attenuated apoptosis ranging from195 to 258 [105]
Tenuifoliside B (102) from the Polygala genus was ableto significantly shorten the coma time of KCN-inducedanoxia mice at the doses of 3 and 10mgkg and it playedan important role in ameliorating the scopolamine-inducedimpairment of performance in passive avoidance task inrats and enhancing the tremors induced by oxotremorine inmiceThese results together demonstrated that tenuifoliside Bpossessed cognitive improving and cerebral protective effects[56]
36 Antidiabetic Activity Diabetes mellitus a chronic debil-itating metabolic disease is characterized by high bloodglucose content and comprises three types termed type Itype II and gestational diabetes [106] Stachyose (19) extract(a part) from Rehmannia glutinosa obviously exhibited theactivity of downregulating fasting plasma glucose level andpartially keeping from hyperglycemia induced by adrenalineand glucose without obvious dose-dependent effect Otherthan that in vivo tests in rats induced by alloxan revealed
that stachyose extract at the dose of 200mgkg significantlydecreased blood-sugar level [15]
Diboside A lapathosides C and D vanicosides A andB and hydropiperoside were isolated from the FagopyrumPolygonum and Persicaria genera belonging to the Polygo-naceae family Diboside A (116) could potentially inhibit 120572-amylase activity with an IC
50of 269 120583M and thus retard the
starch digestion rate which is helpful for diabetic individualsin controlling blood sugar level [107] Lapathoside D (38)exerted stronger activity of 120572-glucosidase inhibition with anIC50
value of 0113mM than acarbose which was chosen asa positive drug for the treatment of type II diabetes [43]Vanicoside B (111) was reported to have higher 120573-glucosidaseinhibitory activity with an IC
50of 505 120583M than vanicoside A
(110) with an IC50of 599 120583M because of the acetyl moiety of
the latter possibly decreasing inhibitory activity of vanicosideA [71]
Fujimoto et al investigated the inhibitory effects ofmumeoses FndashO (83ndash92) from the Prunus genus on aldosereductase and discovered that caffeoyl groups are crucialfor the inhibitory effect on aldose reductase And thusmumeoses F G H J K L M and N (IC
50= 22ndash77120583M) with
a coumaroyl group and acetyl groups inhibited moderatelyaldose reductase from reducing glucose to sorbitol whichis associated with the chronic complications of diabetes [6364]
37 Elicitors and Regulators Oligosaccharides are quitepropitious for encoding biological information because ofdiverse monosaccharide units and complex molecular struc-tures and they are therefore first described as biological
18 Evidence-Based Complementary and Alternative Medicine
181 H
H
H
H
H
H
H
H
H H
H
H
H
H
H
H
H H
HH
Benzyl
Benzyl
Benzyl
182
183
184 Ac
Ac
Ac
Ac
Ac
Ac
Ac
Ac
Ac
Ac
185
186
187
188
189
R1 R2 R3
R1 R2 R3 R4
OCH3
R3OH2C OR2
OR1
OR1
O
O
O
O O
OOO
O
OO
O
OH
OH
OH OH
OH
O O
O
O
OH
HO
OH
OH OHOH
OH
OH
OHHO
HO
OH
OH
HO
CH2OH
CH2OH
CH2OH
CH2OH
C
R2O
R3O
CH2OR4
CH2CH2 CH2CH2CH2CH2CH3
CH3
CH3
191190 192
193
O
C C
O
OO
OO
OO
OO
O O
O
O
O
O
O
O
OH
OH
OHHO
HO
HOOH
OH
OH
OH
HO
OH
OH
OH
OH
HO
HO
C C
R998400O
R998400
Figure 6
signals in plants [108] Oligosaccharides from the cell wallfragments of plants and fungi are powerful signal moleculessuch as the elicitors of plant defence response and theregulators of plant growth and they are capable of exertingbiological activities at exceedingly low concentrations [109]Heptasaccharide (HS) (15) and octasaccharide (OS) (16) iso-lated from the Paris genus possessed plant growth-regulatory
activities [29 30]The two oligosaccharides significantly pro-moted the proliferation of Paris polyphylla var yunnanensisroots at the doses of 25ndash20mgL The octasaccharide hadthe most obvious effect on the growth of Panax japonicusvar major hairy roots at a dose of 30mgL while the otherhad the most positive effect on saponin accumulation ofPanax japonicus var major hairy roots at a dose of 10mgL
Evidence-Based Complementary and Alternative Medicine 19
[29] Similarly Zhou et al evaluated the stimulating effectsof HS and OS on the root growth and saponin productionof Panax ginseng hairy roots which were induced from theplant roots infected withAgrobacterium rhizogenes strain A4The results showed that there was a maximum effect on thehairy roots growth and saponin accumulation on day 10Compared with control group the root biomass dry weightwas increased by more than 17-fold while the total saponincontent of roots increased by more than 1-fold when thesetwo oligosaccharides were added to the hairy root at a dose of30mgL [30] The above data illustrate that HS and OS couldserve as the plant growth-regulators not only in their originalspecies but also in others
38 Immunopotentiating Activity Macrophages are impor-tant targets of investigations on cytophagy cellular immunityand molecular immunology Therefore they are deemedto play a vital role in host defense comprising phagocy-tosis proteolytic processing pathogenic agent apoptosiscytokines production and foreign antigens presentation[110] The water-extracted oligosaccharides from Panax gin-seng (WGOS) exhibited better immunopotentiating activ-ity by increasing phagocytic function of macrophages andpromoting NO TNF-120572 and reactive oxygen species pro-duction [110] In addition Wan et al have obtained malto-oligosaccharides (17 119899 = 3sim8) and three oligosaccharides (213 14) from the Panax ginseng roots The in vitro bioassaypointed out thatWGOS could serve as efficacious stimulatorsof B and T lymphocytes [28] These studies provided enlight-enment that the mixture of oligosaccharides from Chineseherbalmedicine exhibits significant effect on immune system
39 Others Acetylcholinesterase (AChE) inhibitors showgood therapeutic effects onmyasthenia gravis glaucoma andAlzheimerrsquos disease through reversible enzyme inhibitionso as to increase the accumulation of acetylcholine in thesynapse and then promote and prolong the function ofacetylcholine Vanicoside B (111) showed AChE inhibitoryactivity with an IC
50of 0062mM while hydropiperoside
(42) and lapathosides C (115) and D (38) just exhibited weakenzyme inhibitory activity [43]
Wang et al has explored low molecular mass carbohy-drate polymer from Panax ginseng roots and obtained 30ethanol elution (PGO)which included peptides and oligosac-charides (17 119899 = 0sim5) identified as maltose maltotriosemaltotetraose maltopentaose maltohexaose and maltohep-taose Pharmacological experiments revealed that PGO couldsignificantly enhance the memory in scopolamine-inducedmemory deficit rats [27]
Cistanoside F (129) and kankanose (150) were isolatedfrom the Cistanche Paulownia and Acanthus genera Phar-macological experiments showed that cistanoside F andkankanose significantly exhibited vasorelaxant effects on thenoradrenaline-induced contraction of thoracic aorta fromrats [80]
4 Conclusion
Traditional Chinese medicine from natural kingdom playsan indelible role in the treatment of human diseases andit has aroused the attention of those who have engagedin medicinal pharmaceutical chemistry Therefore scientistshave made great contributions day after day to investigate thevalid chemicals from traditional Chinese medicines In thepast decades about 193 oligosaccharides and their esters havebeen identified from traditional Chinese medicinal plantsOn the one hand only a few oligosaccharides and theirmixtures were investigated and just exhibited antidepres-sant antineoplastic antidiabetic plant growth-regulatoryimmunopotentiating and enhancedmemory activitiesMoreexploratory work is still needed to excavate biological andpharmacological activities of oligosaccharides On the otherhand oligosaccharide esters exhibited multi-advantageousactivities Bioassays have revealed that antioxidant cytotoxicantineoplastic and anti-inflammatory activities are the mostnotable bioactivities Of course to search for the naturalproducts with these activities is a hotpot in the contemporarydrug research Oligosaccharide esters provide a vast treasuretrove for medical researchers After considering the currentstudies it should be taken as future directions to makemore mechanism of action studies and clinical trials tofurther evaluate its potential as new drugs Moreover thestructure-activity relationships discussed in this review willprovide reference information for further exploring theirrelationships and continually discovering the new bioactiveoligosaccharide esters
Conflict of Interests
The authors declare that there is no conflict of interestsregarding the publication of this paper
References
[1] X D Yang L J Zhang B Liang L Z Xu and S L YangldquoOligosaccharide esters isolated from plants of PolygalaceaerdquoChinese Traditional and Herbal Drugs vol 33 no 10 pp 954ndash958 2002
[2] N Ogwuru and M Adamczeski ldquoBioactive natural productsderived from Polygonum species of plants their structures andmechanisms of actionrdquo Studies in Natural Products Chemistryvol 22 pp 607ndash642 2000
[3] S Kobayashi T Miyase and H Noguchi ldquoPolyphenolic glyco-sides and oligosaccharide multiesters from the roots of Polygaladalmaisianardquo Journal of Natural Products vol 65 no 3 pp 319ndash328 2002
[4] M Takasaki S Kuroki M Kozuka and T Konoshima ldquoNewphenylpropanoid esters of sucrose from Polygonum lapathi-foliumrdquo Journal of Natural Products vol 64 no 10 pp 1305ndash1308 2001
[5] M L Zimmermann and A T Sneden ldquoVanicosides A and Bprotein kinase C inhibitors from Polygonum pensylvanicumrdquoJournal of Natural Products vol 57 no 2 pp 236ndash242 1994
[6] M Takasaki T Konoshima S Kuroki H Tokuda and HNishino ldquoCancer chemopreventive activity of phenylpropanoid
20 Evidence-Based Complementary and Alternative Medicine
esters of sucrose vanicoside B and lapathoside A from Poly-gonum lapathifoliumrdquo Cancer Letters vol 173 no 2 pp 133ndash138 2001
[7] Q Fu T Liang Z Y Li et al ldquoSeparation of carbohydrates usinghydrophilic interaction liquid chromatographyrdquo CarbohydrateResearch vol 379 pp 13ndash17 2013
[8] M F Mrozek D Zhang and D Ben-Amotz ldquoOligosaccharideidentification and mixture quantification using Raman spec-troscopy and chemometric analysisrdquo Carbohydrate Researchvol 339 no 1 pp 141ndash145 2004
[9] G S Armstrong and B Bendiak ldquoHigh-resolution four-dimen-sional carbon-correlated 1H-1H ROESY experiments employ-ing isotags and the filter diagonalization method for effectiveassignment of glycosidic linkages in oligosaccharidesrdquo Journalof Magnetic Resonance vol 181 no 1 pp 79ndash88 2006
[10] G S Armstrong V A Mandelshtam A J Shaka and BBendiak ldquoRapid high-resolution four-dimensional NMR spec-troscopy using the filter diagonalization method and its advan-tages for detailed structural elucidation of oligosaccharidesrdquoJournal of Magnetic Resonance vol 173 no 1 pp 160ndash168 2005
[11] H-M Tseng S Gattolin J Pritchard H J Newbury and DA Barrett ldquoAnalysis of mono- di- and oligosaccharides by CEusing a two-stage derivatization method and LIF detectionrdquoElectrophoresis vol 30 no 8 pp 1399ndash1405 2009
[12] N Li X Li B L Hou and D L Meng ldquoNew disaccharosidefrom Camptosorus sibiricus Ruprrdquo Natural Product Researchvol 22 no 15 pp 1379ndash1383 2008
[13] Z Zhang D Wang Y Zhao H Gao Y-H Hu and J-FHu ldquoFructose-derived carbohydrates from Alisma orientalisrdquoNatural Product Research vol 23 no 11 pp 1013ndash1020 2009
[14] X Yang Y Zhao N He and K D Croft ldquoIsolation char-acterization and immunological effects of 120572-galacto-oligo-saccharides from a new source the herb Lycopus lucidus TurczrdquoJournal of Agricultural and Food Chemistry vol 58 no 14 pp8253ndash8258 2010
[15] R X Zhang Z P Jia L Y Kong et al ldquoStachyose extractfrom Rehmannia glutinosa Libosch to lower plasma glucose innormal and diabetic rats by oral administrationrdquo Pharmazievol 59 no 7 pp 552ndash556 2004
[16] R Zhang Y Zhao Y Sun X Lu and X Yang ldquoIsolationcharacterization and hepatoprotective effects of the raffinosefamily oligosaccharides from Rehmannia glutinosa liboschrdquoJournal of Agricultural and Food Chemistry vol 61 no 32 pp7786ndash7793 2013
[17] H Li F Song Z Zheng Z Liu and S Liu ldquoCharacterization ofsaccharides and phenolic acids in the Chinese herb Tanshen byESI-FT-ICR-MS and HPLCrdquo Journal of Mass Spectrometry vol43 no 11 pp 1545ndash1552 2008
[18] J E Deng J Zhang XM ChenW Ke and G Y Tian ldquoStudieson the physicochemical properties structure and antitumoractivity of an oligosaccharide homologue SnS-2 from the root ofScrophularia ningpoensis Hemslrdquo Chinese Journal of Chemistryvol 22 no 5 pp 492ndash497 2004
[19] S C Chou LM Chuang and S S Lee ldquoHypoglycemic constit-uents of gynura divaricata subsp formosanardquo Natural ProductCommunications vol 7 no 2 pp 221ndash222 2012
[20] F Feng L-L Wang X-P Lai Y-B Li Z-M Cao and Y-J Zhou ldquoStudy on oligosaccharides from Morinda officinalisrdquoJournal of Chinese Medicinal Materials vol 35 no 8 pp 1259ndash1262 2012
[21] Y F Li Z H Gong M Yang Y M Zhao and Z P Luo ldquoInhibi-tion of the oligosaccharides extracted fromMorinda officinalis
a Chinese traditional herbal medicine on the corticosteroneinduced apoptosis in PC12 cellsrdquo Life Sciences vol 72 no 8 pp933ndash942 2003
[22] Y-F Li Y-Q Liu M Yang et al ldquoThe cytoprotective effect ofinulin-type hexasaccharide extracted from Morinda officinalison PC12 cells against the lesion induced by corticosteronerdquo LifeSciences vol 75 no 13 pp 1531ndash1538 2004
[23] D N Olennikov L M Tankhaeva and A V Rokhin ldquoGlu-cofructans from Saussurea lappa rootsrdquo Chemistry of NaturalCompounds vol 47 no 3 pp 339ndash342 2011
[24] S K Hyun H A Jung B S Min J H Jung and J S ChoildquoIsolation of phenolics nucleosides saccharides and an alkaloidfrom the root of Aralia cordatardquo Natural Product Sciences vol16 no 1 pp 20ndash25 2010
[25] Z J Xu C W Lin and M F Liao ldquoStructure analysis of a newoligosaccharides BROS from Blumea ripariardquo Chinese Journalof Organic Chemistry vol 31 no 11 pp 1811ndash1819 2011
[26] Z J Xu C W Lin and Y Shi ldquoIsolation and structuredetermination of a new oligosaccharide from Blume ripariardquoJournal of Medicinal Plants Research vol 5 no 14 pp 2956ndash2962 2011
[27] Y Wang R Z Jiang G R Li et al ldquoStructural and enhancedmemory activity studies of extracts from Panax ginseng rootrdquoFood Chemistry vol 119 no 3 pp 969ndash973 2010
[28] DWan L Jiao H Yang and S Liu ldquoStructural characterizationand immunological activities of the water-soluble oligosaccha-rides isolated from thePanax ginseng rootsrdquoPlanta vol 235 no6 pp 1289ndash1297 2012
[29] L G Zhou C Z Yang J Q Li S L Wang and J Y WuldquoHeptasaccharide and octasaccharide isolated from Paris pol-yphylla var yunnanensis and their plant growth-regulatoryactivityrdquo Plant Science vol 165 no 3 pp 571ndash575 2003
[30] L G Zhou X D Cao R F Zhang Y L Peng S J Zhao andJ Y Wu ldquoStimulation of saponin production in Panax ginsenghairy roots by two oligosaccharides from Paris polyphylla varyunnanensisrdquo Biotechnology Letters vol 29 no 4 pp 631ndash6342007
[31] M Vanhaecke W van den Ende E Lescrinier and N Dyu-bankova ldquoIsolation and characterization of a pentasaccharidefrom Stellaria mediardquo Journal of Natural Products vol 71 no 11pp 1833ndash1836 2008
[32] J Feng and W Zhao ldquoComplete 1Hand 13C NMR assignmentsof four new oligosaccharides and two new glycosides fromPeriploca forrestiirdquoMagnetic Resonance in Chemistry vol 47 no8 pp 701ndash705 2009
[33] J Q Feng R J Zhang Y Zhou et al ldquoImmunosuppressive preg-nane glycosides from Periploca sepium and Periploca forrestiirdquoPhytochemistry vol 69 no 15 pp 2716ndash2723 2008
[34] X H Long R Xu Y H Zhang X H Tan andQ Y Sun ldquoA newoligosaccharide from Periploca calophyllardquo Zhongguo ZhongyaoZazhi vol 37 no 2 pp 226ndash229 2012
[35] L Wang Z-Q Yin Y Wang X-Q Zhang Y-L Li and W-CYe ldquoPerisesaccharides A-E new oligosaccharides from the rootbarks ofPeriploca sepiumrdquoPlantaMedica vol 76 no 9 pp 909ndash915 2010
[36] T Lei L Zhang H-Y Jiang Y Hu A-H Hong and Y-Z CenldquoA new pregnane glycoside and oligosaccharide from Parabar-ium huaitingiirdquo Journal of Asian Natural Products Research vol13 no 11 pp 1030ndash1035 2011
[37] J Li Y Jiang and P F Tu ldquoTricornoses A-L oligosaccharidemulti-esters from the roots of Polygala tricornisrdquo Journal ofNatural Products vol 68 no 5 pp 739ndash744 2005
Evidence-Based Complementary and Alternative Medicine 21
[38] H H Tu P Liu L Mu et al ldquoStudy on antidepressant com-ponents of sucrose ester from Polygala tenuifoliardquo ZhongguoZhongyao Zazhi vol 33 no 11 pp 1278ndash1280 2008
[39] G M She Y Y Ba Y Liu H Lv W Wang and R B ShildquoAbsorbable phenylpropenoyl sucroses from Polygala tenuifo-liardquoMolecules vol 16 no 7 pp 5507ndash5513 2011
[40] J Yong and P F Tu ldquoStudies on the chemical constituents inroot bark of Polygala tenuifolia (II)rdquo China Journal of ChineseMateria Medica vol 29 no 8 pp 751ndash753 2004
[41] M Ono C Takamura F Sugita et al ldquoTwo new steroidglycosides and a new sesquiterpenoid glycoside from theunderground parts of Trillium kamtschaticumrdquo Chemical andPharmaceutical Bulletin vol 55 no 4 pp 551ndash556 2007
[42] Y Ling Z Li M Chen Z Sun M Fan and C HuangldquoAnalysis and detection of the chemical constituents of RadixPolygalae and their metabolites in rats after oral administrationby ultra high-performance liquid chromatography coupledwith electrospray ionization quadrupole time-of-flight tandemmass spectrometryrdquo Journal of Pharmaceutical and BiomedicalAnalysis vol 85 pp 1ndash13 2013
[43] P Fan L Terrier A-E Hay A Marston and K HostettmannldquoAntioxidant and enzyme inhibition activities and chemicalprofiles ofPolygonum sachalinensis FSchmidt exMaxim (Polyg-onaceae)rdquo Fitoterapia vol 81 no 2 pp 124ndash131 2010
[44] L J Zhang C C Liao H C Huang Y C Shen L M Yangand Y H Kuo ldquoAntioxidant phenylpropanoid glycosides fromSmilax bracteatardquo Phytochemistry vol 69 no 6 pp 1398ndash14042008
[45] L L Yan W Y Gao Y J Zhang and Y Wang ldquoA new phenyl-propanoid glycosides from Paris polyphylla var yunnanensisrdquoFitoterapia vol 79 no 4 pp 306ndash307 2008
[46] Y H Kuo Y W Hsu C C Liaw J K Lee H C Huang andL M Y Kuo ldquoCytotoxic phenylpropanoid glycosides from thestems of Smilax chinardquo Journal of Natural Products vol 68 no10 pp 1475ndash1478 2005
[47] W-X Wang T-X Li H Ma J-F Zhang and A-Q JialdquoTumoral cytotoxic and antioxidative phenylpropanoid glyco-sides in Smilax riparia A DCrdquo Journal of Ethnopharmacologyvol 149 no 2 pp 527ndash532 2013
[48] N X Nhiem P vanKiem C vanMinh et al ldquoPhenylpropanoidglycosides fromHeterosmilax erythrantha and their antioxidantactivityrdquo Archives of Pharmacal Research vol 32 no 10 pp1373ndash1377 2009
[49] Y Wang W Y Gao T J Zhang and Y Q Guo ldquoA novelphenylpropanoid glycosides and a new derivation of phenolicglycoside from Paris Polyphylla var yunnanensisrdquo ChineseChemical Letters vol 18 no 5 pp 548ndash550 2007
[50] J-Y Zhang Y-Z Wang Y-L Zhao et al ldquoPhytochemicals andbioactivities of Paris speciesrdquo Journal of Asian Natural ProductsResearch vol 13 no 7 pp 670ndash681 2011
[51] N H N Hashim F Abas K Shaari and N H Lajis ldquoLC-DAD-ESIMSMS characterization of antioxidant and anti-cholinesterase constituents present in the active fraction fromPersicaria hydropiperrdquo LWT Food Science and Technology vol46 no 2 pp 468ndash476 2012
[52] PH FanA EHayAMarstonHX Lou andKHostettmannldquoChemical variability of the invasive neophytes Polygonumcuspidatum Sieb and Zucc and Polygonum sachalinensis FSchmidt ex Maximrdquo Biochemical Systematics and Ecology vol37 no 1 pp 24ndash34 2009
[53] P Liu Y Hu D H Guo et al ldquoPotential antidepressantproperties of Radix Polygalae (Yuan Zhi)rdquo Phytomedicine vol17 no 10 pp 794ndash799 2010
[54] J F Wu S B Chen S L Chen and P F Tu ldquoThe chemical con-stituents of Polygala hongkongensisHemslrdquoActa PharmaceuticaSinica vol 42 no 7 pp 757ndash761 2007
[55] Y Song Y Jiang D Bi X Tian L Liang and P Tu ldquoChemicalconstituents from n-butanol extract of aerial part of Polygalasibiricardquo Zhongguo Zhongyao Zazhi vol 37 no 4 pp 471ndash4742012
[56] Y Ikeya S Takeda M Tunakawa et al ldquoCognitive improvingand cerebral protective effects of acylated oligosaccharides inPolygala tenuifoliardquo Biological and Pharmaceutical Bulletin vol27 no 7 pp 1081ndash1085 2004
[57] C J Zheng C L Hu X Q Ma C Peng H Zhang and L PQin ldquoCytotoxic phenylpropanoid glycosides from Fagopyrumtataricum (L) Gaertnrdquo Food Chemistry vol 132 no 1 pp 433ndash438 2012
[58] X Li Y F Zhang L Yang et al ldquoChemical profiling ofconstituents of Smilacis glabrae using ultra-high pressure liquidchromatography coupled with LTQ orbitrap mass spectrome-tryrdquo Natural Product Communications vol 7 no 2 pp 181ndash1842012
[59] T-T Sun D-W Zhang Y Han F-Y Dong andWWang ldquoSmi-lasides M and N two new phenylpropanoid glycosides fromSmilax ripariardquo Journal of Asian Natural Products Research vol14 no 2 pp 165ndash170 2012
[60] J Li X Bi G Zheng Y Hitoshi T Ikeda and T NoharaldquoSteroidal glycosides and aromatic compounds from Smilaxripariardquo Chemical amp Pharmaceutical Bulletin vol 54 no 10 pp1451ndash1454 2006
[61] N Wang X Yao R Ishii and S Kitanaka ldquoBioactive sucroseesters from Bidens parviflorardquo Phytochemistry vol 62 no 5 pp741ndash746 2003
[62] S Nakamura K Fujimoto T Matsumoto et al ldquoAcylatedsucroses and acylated quinic acids analogs from the flower budsof Prunus mume and their inhibitory effect on melanogenesisrdquoPhytochemistry vol 92 pp 128ndash136 2013
[63] K Fujimoto SNakamura TMatsumoto et al ldquoMedicinal flow-ers XXXVIII Structures of acylated sucroses and inhibitoryeffects of constituents on aldose reducatase from the flower budsofPrunusmumerdquoChemical and Pharmaceutical Bulletin vol 61no 4 pp 445ndash451 2013
[64] S Nakamura K Fujimoto T Matsumoto et al ldquoStructuresof acylated sucroses and an acylated flavonol glycoside andinhibitory effects of constituents on aldose reductase from theflower buds of Prunus mumerdquo Journal of Natural Medicines vol67 no 4 pp 799ndash806 2013
[65] L-B Dong J He X-Y Li et al ldquoChemical constituents fromthe aerial parts of Musella lasiocarpardquo Natural Products andBioprospecting vol 1 no 1 pp 41ndash47 2011
[66] Y Xiong K Z Deng Y Q Guo W Y Gao and T J ZhangldquoNew chemical constituents from the rhizomes of Sparganiumstoloniferumrdquo Archives of Pharmacal Research vol 32 no 5 pp717ndash720 2009
[67] Y Xiong K-Z Deng Y-Q Guo W-Y Gao and T-J ZhangldquoTwo new sucrose esters from Sparganium stoloniferumrdquo Jour-nal of Asian Natural Products Research vol 10 no 5 pp 425ndash428 2008
[68] B Chen N L Wang J H Huang and X S Yao ldquoIridoidand phenylpropanoid glycosides from Scrophularia ningpoensis
22 Evidence-Based Complementary and Alternative Medicine
Hemslrdquo Asian Journal of Traditional Medicines vol 2 no 3 pp119ndash123 2007
[69] H Chen Y Z Zhou L Qiao et al ldquoTwo new compounds fromCynanchum amplexicaulerdquo Journal of Asian Natural ProductsResearch vol 10 no 3 pp 248ndash251 2008
[70] C-L Chang L-J Zhang R Y Chen et al ldquoAntioxidant andanti-inflammatory phenylpropanoid derivatives from Calamusquiquesetinerviusrdquo Journal of Natural Products vol 73 no 9 pp1482ndash1488 2010
[71] Y Kawai H Kumagai H Kurihara K Yamazaki R Sawanoand N Inoue ldquo120573-Glucosidase inhibitory activities of phenyl-propanoid glycosides vanicoside A and B from Polygonumsachalinense rhizomerdquo Fitoterapia vol 77 no 6 pp 456ndash4592006
[72] P V Kiem N X Nhiem N X Cuong et al ldquoNew phenyl-propanoid esters of sucrose from Polygonum hydropiper andtheir antioxidant activityrdquo Archives of Pharmacal Research vol31 no 11 pp 1477ndash1482 2008
[73] K J Wang Y J Zhang and C R Yang ldquoAntioxidant phenolicconstituents from Fagopyrum dibotrysrdquo Journal of Ethnophar-macology vol 99 no 2 pp 259ndash264 2005
[74] N Cho J Huh H Yang et al ldquoChemical constituentsof Polygala tenuifolia roots and their inhibitory activity onlipopolysaccharide-induced nitric oxide production in BV2microgliardquo Journal of Enzyme Inhibition and Medicinal Chem-istry vol 27 no 1 pp 1ndash4 2012
[75] Q Ren C S Wu and J L Zhang ldquoUse of on-line stop-flowheart-cutting two-dimensional high performance liquid chro-matography for simultaneous determination of 12 major con-stituents in tartary buckwheat (Fagopyrum tataricum Gaertn)rdquoJournal of Chromatography A vol 1304 pp 257ndash262 2013
[76] Q Ren C S Wu Y Ren and J L Zhang ldquoCharacterizationand identification of the chemical constituents from tartarybuckwheat (Fagopyrum tataricumGaertn) by high performanceliquid chromatographyphotodiode array detectorlinear iontrap FTICR hybrid mass spectrometryrdquo Food Chemistry vol136 no 3-4 pp 1377ndash1389 2013
[77] W Li Y N Sun X T Yan et al ldquoNF-120581B inhibitory activityof sucrose fatty acid esters and related constituents fromAstragalus membranaceusrdquo Journal of Agricultural and FoodChemistry vol 61 no 29 pp 7081ndash7088 2013
[78] J T Cheng J He Y Li et al ldquoThree new sucrose fatty acid estersfrom Equisetum hiemale LrdquoHelvetica Chimica Acta vol 95 no7 pp 1158ndash1163 2012
[79] Y Jiang and P-F Tu ldquoTenuifoliose Q a new oligosaccharideester from the root of Polygala tenuifoliaWilldrdquo Journal of AsianNatural Products Research vol 5 no 4 pp 279ndash283 2003
[80] M Yoshikawa H Matsuda T Morikawa H H Xie S Naka-mura and O Muraoka ldquoPhenylethanoid oligoglycosides andacylated oligosugars with vasorelaxant activity from Cistanchetubulosardquo Bioorganic ampMedicinal Chemistry vol 14 no 22 pp7468ndash7475 2006
[81] P-F Tu H-M Shi Z-H Song Y Jiang and Y-Y ZhaoldquoChemical constituents of Cistanche sinensisrdquo Journal of AsianNatural Products Research vol 9 no 1 pp 79ndash84 2007
[82] C-L Si Y-Y Lu P-P Qin R-C Sun and Y-H Ni ldquoPhenolicextractives with chemotaxonomic significance from the bark ofPaulownia tomentosa var tomentosardquo BioResources vol 6 no4 pp 5086ndash5098 2011
[83] J Wu S Zhang Q Xiao et al ldquoPhenylethanoid and aliphaticalcohol glycosides from Acanthus ilicifoliusrdquo Phytochemistryvol 63 no 4 pp 491ndash495 2003
[84] Y Jiang and P-F Tu ldquoAnalysis of chemical constituents inCistanche speciesrdquo Journal of Chromatography A vol 1216 no11 pp 1970ndash1979 2009
[85] H Otsuka H Kuwabara and H Hoshiyama ldquoIdentification ofsucrose diesters of aryldihydronaphthalene-type lignans fromTrigonotis peduncularisand the nature of their fluorescencerdquoJournal of Natural Products vol 71 no 7 pp 1178ndash1181 2008
[86] M-R Suo J-S Yang and Q-H Liu ldquoLignan oligosaccharideesters from Eritrichium rupestrerdquo Journal of Natural Productsvol 69 no 4 pp 682ndash684 2006
[87] P-F Tu Z-H Song H-M Shi Y Jiang and Y-Y ZhaoldquoArylethyl (=phenylethanoid) glycosides and oligosaccharidefrom the stem of Cistanche tubulosardquo Helvetica Chimica Actavol 89 no 5 pp 927ndash935 2006
[88] M-H Shyr T-H Tsai and L-C Lin ldquoRossicasins A Band rosicaside F three new phenylpropanoid glycosides fromBoschniakia rossicardquoChemical and Pharmaceutical Bulletin vol54 no 2 pp 252ndash254 2006
[89] R FangNCVeitchGCKiteM J RHowes EA Porter andM S J Simmonds ldquoGlycosylated constituents of Iris fulvaandIris brevicaulisrdquoChemical amp Pharmaceutical Bulletin vol 59 no1 pp 124ndash128 2011
[90] J Fu L Zuo J Yang R Chen and D Zhang ldquoOligosaccharidepolyester and triterpenoid saponins from the roots of Polygalajaponicardquo Phytochemistry vol 69 no 7 pp 1617ndash1624 2008
[91] M-C Cheng C-Y Li H-C Ko F-N Ko Y-L Lin andT-S Wu ldquoAntidepressant principles of the roots of polygalatenuifoliardquo Journal of Natural Products vol 69 no 9 pp 1305ndash1309 2006
[92] H T Chang and P F Tu ldquoNew oligosaccharide esters andxanthone C-glucosides from Polygala telephioidesrdquo HelveticaChimica Acta vol 90 no 5 pp 944ndash950 2007
[93] J Li L Feng J Dai R Wang and T Nohara ldquoChemical con-stituents from Polygala telephioidesrdquo China Journal of ChineseMateria Medica vol 34 no 4 pp 402ndash405 2009
[94] W-P Yin T-Z Zhao and H-Y Zhang ldquoA novel oligosaccha-ride ester from Syringa pubescensrdquo Journal of Asian NaturalProducts Research vol 10 no 1 pp 95ndash100 2008
[95] M Valko D Leibfritz J Moncol M T D Cronin M Mazurand J Telser ldquoFree radicals and antioxidants in normal physio-logical functions and human diseaserdquoThe International Journalof Biochemistry amp Cell Biology vol 39 no 1 pp 44ndash84 2007
[96] D Krishnaiah R Sarbatly and R Nithyanandam ldquoA review ofthe antioxidant potential of medicinal plant speciesrdquo Food andBioproducts Processing vol 89 no 3 pp 217ndash233 2011
[97] P Liu Y Hu D-H Guo et al ldquoAntioxidant activity ofoligosaccharide ester extracted from Polygala tenuifolia roots insenescence-accelerated micerdquo Pharmaceutical Biology vol 48no 7 pp 828ndash833 2010
[98] Y Hu H-B Liao G Dai-Hong P Liu Y-Y Wang and KRahman ldquoAntidepressant-like effects of 361015840-disinapoyl sucroseon hippocampal neuronal plasticity and neurotrophic signalpathway in chronically mild stressed ratsrdquo NeurochemistryInternational vol 56 no 3 pp 461ndash465 2010
[99] Y Hu H B O Liao P Liu D-H Guo and K RahmanldquoA bioactive compound from Polygala tenuifolia regulatesefficiency of chronic stress on hypothalamic-pituitary-adrenalaxisrdquo Pharmazie vol 64 no 9 pp 605ndash608 2009
[100] A Jungbauer and SMedjakovic ldquoAnti-inflammatory propertiesof culinary herbs and spices that ameliorate the effects ofmetabolic syndromerdquoMaturitas vol 71 no 3 pp 227ndash239 2012
Evidence-Based Complementary and Alternative Medicine 23
[101] Q Xu Y Wang S Guo Z Shen and L Yang ldquoAnti-inflammatory and analgesic activity of aqueous extract of Flospopulirdquo Journal of Ethnopharmacology vol 152 no 3 pp 540ndash545 2014
[102] K S Kim D S Lee G S Bae et al ldquoThe inhibition of JNKMAPK and NF-120581B signaling by tenuifoliside A isolated fromPolygala tenuifolia in lipopolysaccharide-induced macrophagesis associated with its anti-inflammatory effectrdquo European Jour-nal of Pharmacology vol 721 no 1ndash3 pp 267ndash276 2013
[103] J-G Lee J-M Yon C Lin A Y Jung K Y Jung and S-YNamldquoCombined treatment with capsaicin and resveratrol enhancesneuroprotection against glutamate-induced toxicity in mousecerebral cortical neuronsrdquo Food and Chemical Toxicology vol50 no 11 pp 3877ndash3885 2012
[104] M L Jin S Y Park Y H Kim J-I Oh S J Lee andG Park ldquoThe neuroprotective effects of cordycepin inhibitglutamate-induced oxidative andER stress-associated apoptosisin hippocampal HT22 cellsrdquo NeuroToxicology vol 41 pp 102ndash111 2014
[105] P Liu Y Hu J Li et al ldquoProtection of SH-SY5Y neuronal cellsfrom glutamate-induced apoptosis by 36rsquo-disinapoyl sucrosea bioactive compound isolated from radix polygalardquo Journal ofBiomedicine and Biotechnology vol 2012 Article ID 728342 5pages 2012
[106] P-B Li W-L Lin Y-G Wang W Peng X-Y Cai and W-WSu ldquoAntidiabetic activities of oligosaccharides of Ophiopogonisjaponicus in experimental type 2 diabetic ratsrdquo InternationalJournal of Biological Macromolecules vol 51 no 5 pp 749ndash7552012
[107] T Liu Y M Yip L Song et al ldquoInhibiting enzymatic starchdigestion by the phenolic compound diboside A a mechanisticand in silico studyrdquo Food Research International vol 54 no 1pp 595ndash600 2013
[108] F Cote andMGHahn ldquoOligosaccharins structures and signaltransductionrdquo Plant Molecular Biology vol 26 no 5 pp 1379ndash1411 1994
[109] RACreelman and J EMullet ldquoOligosaccharins brassinolidesand jasmonates nontraditional regulators of plant growthdevelopment and gene expressionrdquo Plant Cell vol 9 no 7 pp1211ndash1223 1997
[110] L Jiao D Wan X Zhang B Li H Zhao and S LiuldquoCharacterization and immunostimulating effects on murineperitoneal macrophages of oligosaccharide isolated from Panaxginseng CAMeyerrdquo Journal of Ethnopharmacology vol 144 no3 pp 490ndash496 2012
Submit your manuscripts athttpwwwhindawicom
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Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
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Disease Markers
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OncologyJournal of
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Oxidative Medicine and Cellular Longevity
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The Scientific World JournalHindawi Publishing Corporation httpwwwhindawicom Volume 2014
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Research and TreatmentAIDS
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Parkinsonrsquos Disease
Evidence-Based Complementary and Alternative Medicine
Volume 2014Hindawi Publishing Corporationhttpwwwhindawicom
18 Evidence-Based Complementary and Alternative Medicine
181 H
H
H
H
H
H
H
H
H H
H
H
H
H
H
H
H H
HH
Benzyl
Benzyl
Benzyl
182
183
184 Ac
Ac
Ac
Ac
Ac
Ac
Ac
Ac
Ac
Ac
185
186
187
188
189
R1 R2 R3
R1 R2 R3 R4
OCH3
R3OH2C OR2
OR1
OR1
O
O
O
O O
OOO
O
OO
O
OH
OH
OH OH
OH
O O
O
O
OH
HO
OH
OH OHOH
OH
OH
OHHO
HO
OH
OH
HO
CH2OH
CH2OH
CH2OH
CH2OH
C
R2O
R3O
CH2OR4
CH2CH2 CH2CH2CH2CH2CH3
CH3
CH3
191190 192
193
O
C C
O
OO
OO
OO
OO
O O
O
O
O
O
O
O
OH
OH
OHHO
HO
HOOH
OH
OH
OH
HO
OH
OH
OH
OH
HO
HO
C C
R998400O
R998400
Figure 6
signals in plants [108] Oligosaccharides from the cell wallfragments of plants and fungi are powerful signal moleculessuch as the elicitors of plant defence response and theregulators of plant growth and they are capable of exertingbiological activities at exceedingly low concentrations [109]Heptasaccharide (HS) (15) and octasaccharide (OS) (16) iso-lated from the Paris genus possessed plant growth-regulatory
activities [29 30]The two oligosaccharides significantly pro-moted the proliferation of Paris polyphylla var yunnanensisroots at the doses of 25ndash20mgL The octasaccharide hadthe most obvious effect on the growth of Panax japonicusvar major hairy roots at a dose of 30mgL while the otherhad the most positive effect on saponin accumulation ofPanax japonicus var major hairy roots at a dose of 10mgL
Evidence-Based Complementary and Alternative Medicine 19
[29] Similarly Zhou et al evaluated the stimulating effectsof HS and OS on the root growth and saponin productionof Panax ginseng hairy roots which were induced from theplant roots infected withAgrobacterium rhizogenes strain A4The results showed that there was a maximum effect on thehairy roots growth and saponin accumulation on day 10Compared with control group the root biomass dry weightwas increased by more than 17-fold while the total saponincontent of roots increased by more than 1-fold when thesetwo oligosaccharides were added to the hairy root at a dose of30mgL [30] The above data illustrate that HS and OS couldserve as the plant growth-regulators not only in their originalspecies but also in others
38 Immunopotentiating Activity Macrophages are impor-tant targets of investigations on cytophagy cellular immunityand molecular immunology Therefore they are deemedto play a vital role in host defense comprising phagocy-tosis proteolytic processing pathogenic agent apoptosiscytokines production and foreign antigens presentation[110] The water-extracted oligosaccharides from Panax gin-seng (WGOS) exhibited better immunopotentiating activ-ity by increasing phagocytic function of macrophages andpromoting NO TNF-120572 and reactive oxygen species pro-duction [110] In addition Wan et al have obtained malto-oligosaccharides (17 119899 = 3sim8) and three oligosaccharides (213 14) from the Panax ginseng roots The in vitro bioassaypointed out thatWGOS could serve as efficacious stimulatorsof B and T lymphocytes [28] These studies provided enlight-enment that the mixture of oligosaccharides from Chineseherbalmedicine exhibits significant effect on immune system
39 Others Acetylcholinesterase (AChE) inhibitors showgood therapeutic effects onmyasthenia gravis glaucoma andAlzheimerrsquos disease through reversible enzyme inhibitionso as to increase the accumulation of acetylcholine in thesynapse and then promote and prolong the function ofacetylcholine Vanicoside B (111) showed AChE inhibitoryactivity with an IC
50of 0062mM while hydropiperoside
(42) and lapathosides C (115) and D (38) just exhibited weakenzyme inhibitory activity [43]
Wang et al has explored low molecular mass carbohy-drate polymer from Panax ginseng roots and obtained 30ethanol elution (PGO)which included peptides and oligosac-charides (17 119899 = 0sim5) identified as maltose maltotriosemaltotetraose maltopentaose maltohexaose and maltohep-taose Pharmacological experiments revealed that PGO couldsignificantly enhance the memory in scopolamine-inducedmemory deficit rats [27]
Cistanoside F (129) and kankanose (150) were isolatedfrom the Cistanche Paulownia and Acanthus genera Phar-macological experiments showed that cistanoside F andkankanose significantly exhibited vasorelaxant effects on thenoradrenaline-induced contraction of thoracic aorta fromrats [80]
4 Conclusion
Traditional Chinese medicine from natural kingdom playsan indelible role in the treatment of human diseases andit has aroused the attention of those who have engagedin medicinal pharmaceutical chemistry Therefore scientistshave made great contributions day after day to investigate thevalid chemicals from traditional Chinese medicines In thepast decades about 193 oligosaccharides and their esters havebeen identified from traditional Chinese medicinal plantsOn the one hand only a few oligosaccharides and theirmixtures were investigated and just exhibited antidepres-sant antineoplastic antidiabetic plant growth-regulatoryimmunopotentiating and enhancedmemory activitiesMoreexploratory work is still needed to excavate biological andpharmacological activities of oligosaccharides On the otherhand oligosaccharide esters exhibited multi-advantageousactivities Bioassays have revealed that antioxidant cytotoxicantineoplastic and anti-inflammatory activities are the mostnotable bioactivities Of course to search for the naturalproducts with these activities is a hotpot in the contemporarydrug research Oligosaccharide esters provide a vast treasuretrove for medical researchers After considering the currentstudies it should be taken as future directions to makemore mechanism of action studies and clinical trials tofurther evaluate its potential as new drugs Moreover thestructure-activity relationships discussed in this review willprovide reference information for further exploring theirrelationships and continually discovering the new bioactiveoligosaccharide esters
Conflict of Interests
The authors declare that there is no conflict of interestsregarding the publication of this paper
References
[1] X D Yang L J Zhang B Liang L Z Xu and S L YangldquoOligosaccharide esters isolated from plants of PolygalaceaerdquoChinese Traditional and Herbal Drugs vol 33 no 10 pp 954ndash958 2002
[2] N Ogwuru and M Adamczeski ldquoBioactive natural productsderived from Polygonum species of plants their structures andmechanisms of actionrdquo Studies in Natural Products Chemistryvol 22 pp 607ndash642 2000
[3] S Kobayashi T Miyase and H Noguchi ldquoPolyphenolic glyco-sides and oligosaccharide multiesters from the roots of Polygaladalmaisianardquo Journal of Natural Products vol 65 no 3 pp 319ndash328 2002
[4] M Takasaki S Kuroki M Kozuka and T Konoshima ldquoNewphenylpropanoid esters of sucrose from Polygonum lapathi-foliumrdquo Journal of Natural Products vol 64 no 10 pp 1305ndash1308 2001
[5] M L Zimmermann and A T Sneden ldquoVanicosides A and Bprotein kinase C inhibitors from Polygonum pensylvanicumrdquoJournal of Natural Products vol 57 no 2 pp 236ndash242 1994
[6] M Takasaki T Konoshima S Kuroki H Tokuda and HNishino ldquoCancer chemopreventive activity of phenylpropanoid
20 Evidence-Based Complementary and Alternative Medicine
esters of sucrose vanicoside B and lapathoside A from Poly-gonum lapathifoliumrdquo Cancer Letters vol 173 no 2 pp 133ndash138 2001
[7] Q Fu T Liang Z Y Li et al ldquoSeparation of carbohydrates usinghydrophilic interaction liquid chromatographyrdquo CarbohydrateResearch vol 379 pp 13ndash17 2013
[8] M F Mrozek D Zhang and D Ben-Amotz ldquoOligosaccharideidentification and mixture quantification using Raman spec-troscopy and chemometric analysisrdquo Carbohydrate Researchvol 339 no 1 pp 141ndash145 2004
[9] G S Armstrong and B Bendiak ldquoHigh-resolution four-dimen-sional carbon-correlated 1H-1H ROESY experiments employ-ing isotags and the filter diagonalization method for effectiveassignment of glycosidic linkages in oligosaccharidesrdquo Journalof Magnetic Resonance vol 181 no 1 pp 79ndash88 2006
[10] G S Armstrong V A Mandelshtam A J Shaka and BBendiak ldquoRapid high-resolution four-dimensional NMR spec-troscopy using the filter diagonalization method and its advan-tages for detailed structural elucidation of oligosaccharidesrdquoJournal of Magnetic Resonance vol 173 no 1 pp 160ndash168 2005
[11] H-M Tseng S Gattolin J Pritchard H J Newbury and DA Barrett ldquoAnalysis of mono- di- and oligosaccharides by CEusing a two-stage derivatization method and LIF detectionrdquoElectrophoresis vol 30 no 8 pp 1399ndash1405 2009
[12] N Li X Li B L Hou and D L Meng ldquoNew disaccharosidefrom Camptosorus sibiricus Ruprrdquo Natural Product Researchvol 22 no 15 pp 1379ndash1383 2008
[13] Z Zhang D Wang Y Zhao H Gao Y-H Hu and J-FHu ldquoFructose-derived carbohydrates from Alisma orientalisrdquoNatural Product Research vol 23 no 11 pp 1013ndash1020 2009
[14] X Yang Y Zhao N He and K D Croft ldquoIsolation char-acterization and immunological effects of 120572-galacto-oligo-saccharides from a new source the herb Lycopus lucidus TurczrdquoJournal of Agricultural and Food Chemistry vol 58 no 14 pp8253ndash8258 2010
[15] R X Zhang Z P Jia L Y Kong et al ldquoStachyose extractfrom Rehmannia glutinosa Libosch to lower plasma glucose innormal and diabetic rats by oral administrationrdquo Pharmazievol 59 no 7 pp 552ndash556 2004
[16] R Zhang Y Zhao Y Sun X Lu and X Yang ldquoIsolationcharacterization and hepatoprotective effects of the raffinosefamily oligosaccharides from Rehmannia glutinosa liboschrdquoJournal of Agricultural and Food Chemistry vol 61 no 32 pp7786ndash7793 2013
[17] H Li F Song Z Zheng Z Liu and S Liu ldquoCharacterization ofsaccharides and phenolic acids in the Chinese herb Tanshen byESI-FT-ICR-MS and HPLCrdquo Journal of Mass Spectrometry vol43 no 11 pp 1545ndash1552 2008
[18] J E Deng J Zhang XM ChenW Ke and G Y Tian ldquoStudieson the physicochemical properties structure and antitumoractivity of an oligosaccharide homologue SnS-2 from the root ofScrophularia ningpoensis Hemslrdquo Chinese Journal of Chemistryvol 22 no 5 pp 492ndash497 2004
[19] S C Chou LM Chuang and S S Lee ldquoHypoglycemic constit-uents of gynura divaricata subsp formosanardquo Natural ProductCommunications vol 7 no 2 pp 221ndash222 2012
[20] F Feng L-L Wang X-P Lai Y-B Li Z-M Cao and Y-J Zhou ldquoStudy on oligosaccharides from Morinda officinalisrdquoJournal of Chinese Medicinal Materials vol 35 no 8 pp 1259ndash1262 2012
[21] Y F Li Z H Gong M Yang Y M Zhao and Z P Luo ldquoInhibi-tion of the oligosaccharides extracted fromMorinda officinalis
a Chinese traditional herbal medicine on the corticosteroneinduced apoptosis in PC12 cellsrdquo Life Sciences vol 72 no 8 pp933ndash942 2003
[22] Y-F Li Y-Q Liu M Yang et al ldquoThe cytoprotective effect ofinulin-type hexasaccharide extracted from Morinda officinalison PC12 cells against the lesion induced by corticosteronerdquo LifeSciences vol 75 no 13 pp 1531ndash1538 2004
[23] D N Olennikov L M Tankhaeva and A V Rokhin ldquoGlu-cofructans from Saussurea lappa rootsrdquo Chemistry of NaturalCompounds vol 47 no 3 pp 339ndash342 2011
[24] S K Hyun H A Jung B S Min J H Jung and J S ChoildquoIsolation of phenolics nucleosides saccharides and an alkaloidfrom the root of Aralia cordatardquo Natural Product Sciences vol16 no 1 pp 20ndash25 2010
[25] Z J Xu C W Lin and M F Liao ldquoStructure analysis of a newoligosaccharides BROS from Blumea ripariardquo Chinese Journalof Organic Chemistry vol 31 no 11 pp 1811ndash1819 2011
[26] Z J Xu C W Lin and Y Shi ldquoIsolation and structuredetermination of a new oligosaccharide from Blume ripariardquoJournal of Medicinal Plants Research vol 5 no 14 pp 2956ndash2962 2011
[27] Y Wang R Z Jiang G R Li et al ldquoStructural and enhancedmemory activity studies of extracts from Panax ginseng rootrdquoFood Chemistry vol 119 no 3 pp 969ndash973 2010
[28] DWan L Jiao H Yang and S Liu ldquoStructural characterizationand immunological activities of the water-soluble oligosaccha-rides isolated from thePanax ginseng rootsrdquoPlanta vol 235 no6 pp 1289ndash1297 2012
[29] L G Zhou C Z Yang J Q Li S L Wang and J Y WuldquoHeptasaccharide and octasaccharide isolated from Paris pol-yphylla var yunnanensis and their plant growth-regulatoryactivityrdquo Plant Science vol 165 no 3 pp 571ndash575 2003
[30] L G Zhou X D Cao R F Zhang Y L Peng S J Zhao andJ Y Wu ldquoStimulation of saponin production in Panax ginsenghairy roots by two oligosaccharides from Paris polyphylla varyunnanensisrdquo Biotechnology Letters vol 29 no 4 pp 631ndash6342007
[31] M Vanhaecke W van den Ende E Lescrinier and N Dyu-bankova ldquoIsolation and characterization of a pentasaccharidefrom Stellaria mediardquo Journal of Natural Products vol 71 no 11pp 1833ndash1836 2008
[32] J Feng and W Zhao ldquoComplete 1Hand 13C NMR assignmentsof four new oligosaccharides and two new glycosides fromPeriploca forrestiirdquoMagnetic Resonance in Chemistry vol 47 no8 pp 701ndash705 2009
[33] J Q Feng R J Zhang Y Zhou et al ldquoImmunosuppressive preg-nane glycosides from Periploca sepium and Periploca forrestiirdquoPhytochemistry vol 69 no 15 pp 2716ndash2723 2008
[34] X H Long R Xu Y H Zhang X H Tan andQ Y Sun ldquoA newoligosaccharide from Periploca calophyllardquo Zhongguo ZhongyaoZazhi vol 37 no 2 pp 226ndash229 2012
[35] L Wang Z-Q Yin Y Wang X-Q Zhang Y-L Li and W-CYe ldquoPerisesaccharides A-E new oligosaccharides from the rootbarks ofPeriploca sepiumrdquoPlantaMedica vol 76 no 9 pp 909ndash915 2010
[36] T Lei L Zhang H-Y Jiang Y Hu A-H Hong and Y-Z CenldquoA new pregnane glycoside and oligosaccharide from Parabar-ium huaitingiirdquo Journal of Asian Natural Products Research vol13 no 11 pp 1030ndash1035 2011
[37] J Li Y Jiang and P F Tu ldquoTricornoses A-L oligosaccharidemulti-esters from the roots of Polygala tricornisrdquo Journal ofNatural Products vol 68 no 5 pp 739ndash744 2005
Evidence-Based Complementary and Alternative Medicine 21
[38] H H Tu P Liu L Mu et al ldquoStudy on antidepressant com-ponents of sucrose ester from Polygala tenuifoliardquo ZhongguoZhongyao Zazhi vol 33 no 11 pp 1278ndash1280 2008
[39] G M She Y Y Ba Y Liu H Lv W Wang and R B ShildquoAbsorbable phenylpropenoyl sucroses from Polygala tenuifo-liardquoMolecules vol 16 no 7 pp 5507ndash5513 2011
[40] J Yong and P F Tu ldquoStudies on the chemical constituents inroot bark of Polygala tenuifolia (II)rdquo China Journal of ChineseMateria Medica vol 29 no 8 pp 751ndash753 2004
[41] M Ono C Takamura F Sugita et al ldquoTwo new steroidglycosides and a new sesquiterpenoid glycoside from theunderground parts of Trillium kamtschaticumrdquo Chemical andPharmaceutical Bulletin vol 55 no 4 pp 551ndash556 2007
[42] Y Ling Z Li M Chen Z Sun M Fan and C HuangldquoAnalysis and detection of the chemical constituents of RadixPolygalae and their metabolites in rats after oral administrationby ultra high-performance liquid chromatography coupledwith electrospray ionization quadrupole time-of-flight tandemmass spectrometryrdquo Journal of Pharmaceutical and BiomedicalAnalysis vol 85 pp 1ndash13 2013
[43] P Fan L Terrier A-E Hay A Marston and K HostettmannldquoAntioxidant and enzyme inhibition activities and chemicalprofiles ofPolygonum sachalinensis FSchmidt exMaxim (Polyg-onaceae)rdquo Fitoterapia vol 81 no 2 pp 124ndash131 2010
[44] L J Zhang C C Liao H C Huang Y C Shen L M Yangand Y H Kuo ldquoAntioxidant phenylpropanoid glycosides fromSmilax bracteatardquo Phytochemistry vol 69 no 6 pp 1398ndash14042008
[45] L L Yan W Y Gao Y J Zhang and Y Wang ldquoA new phenyl-propanoid glycosides from Paris polyphylla var yunnanensisrdquoFitoterapia vol 79 no 4 pp 306ndash307 2008
[46] Y H Kuo Y W Hsu C C Liaw J K Lee H C Huang andL M Y Kuo ldquoCytotoxic phenylpropanoid glycosides from thestems of Smilax chinardquo Journal of Natural Products vol 68 no10 pp 1475ndash1478 2005
[47] W-X Wang T-X Li H Ma J-F Zhang and A-Q JialdquoTumoral cytotoxic and antioxidative phenylpropanoid glyco-sides in Smilax riparia A DCrdquo Journal of Ethnopharmacologyvol 149 no 2 pp 527ndash532 2013
[48] N X Nhiem P vanKiem C vanMinh et al ldquoPhenylpropanoidglycosides fromHeterosmilax erythrantha and their antioxidantactivityrdquo Archives of Pharmacal Research vol 32 no 10 pp1373ndash1377 2009
[49] Y Wang W Y Gao T J Zhang and Y Q Guo ldquoA novelphenylpropanoid glycosides and a new derivation of phenolicglycoside from Paris Polyphylla var yunnanensisrdquo ChineseChemical Letters vol 18 no 5 pp 548ndash550 2007
[50] J-Y Zhang Y-Z Wang Y-L Zhao et al ldquoPhytochemicals andbioactivities of Paris speciesrdquo Journal of Asian Natural ProductsResearch vol 13 no 7 pp 670ndash681 2011
[51] N H N Hashim F Abas K Shaari and N H Lajis ldquoLC-DAD-ESIMSMS characterization of antioxidant and anti-cholinesterase constituents present in the active fraction fromPersicaria hydropiperrdquo LWT Food Science and Technology vol46 no 2 pp 468ndash476 2012
[52] PH FanA EHayAMarstonHX Lou andKHostettmannldquoChemical variability of the invasive neophytes Polygonumcuspidatum Sieb and Zucc and Polygonum sachalinensis FSchmidt ex Maximrdquo Biochemical Systematics and Ecology vol37 no 1 pp 24ndash34 2009
[53] P Liu Y Hu D H Guo et al ldquoPotential antidepressantproperties of Radix Polygalae (Yuan Zhi)rdquo Phytomedicine vol17 no 10 pp 794ndash799 2010
[54] J F Wu S B Chen S L Chen and P F Tu ldquoThe chemical con-stituents of Polygala hongkongensisHemslrdquoActa PharmaceuticaSinica vol 42 no 7 pp 757ndash761 2007
[55] Y Song Y Jiang D Bi X Tian L Liang and P Tu ldquoChemicalconstituents from n-butanol extract of aerial part of Polygalasibiricardquo Zhongguo Zhongyao Zazhi vol 37 no 4 pp 471ndash4742012
[56] Y Ikeya S Takeda M Tunakawa et al ldquoCognitive improvingand cerebral protective effects of acylated oligosaccharides inPolygala tenuifoliardquo Biological and Pharmaceutical Bulletin vol27 no 7 pp 1081ndash1085 2004
[57] C J Zheng C L Hu X Q Ma C Peng H Zhang and L PQin ldquoCytotoxic phenylpropanoid glycosides from Fagopyrumtataricum (L) Gaertnrdquo Food Chemistry vol 132 no 1 pp 433ndash438 2012
[58] X Li Y F Zhang L Yang et al ldquoChemical profiling ofconstituents of Smilacis glabrae using ultra-high pressure liquidchromatography coupled with LTQ orbitrap mass spectrome-tryrdquo Natural Product Communications vol 7 no 2 pp 181ndash1842012
[59] T-T Sun D-W Zhang Y Han F-Y Dong andWWang ldquoSmi-lasides M and N two new phenylpropanoid glycosides fromSmilax ripariardquo Journal of Asian Natural Products Research vol14 no 2 pp 165ndash170 2012
[60] J Li X Bi G Zheng Y Hitoshi T Ikeda and T NoharaldquoSteroidal glycosides and aromatic compounds from Smilaxripariardquo Chemical amp Pharmaceutical Bulletin vol 54 no 10 pp1451ndash1454 2006
[61] N Wang X Yao R Ishii and S Kitanaka ldquoBioactive sucroseesters from Bidens parviflorardquo Phytochemistry vol 62 no 5 pp741ndash746 2003
[62] S Nakamura K Fujimoto T Matsumoto et al ldquoAcylatedsucroses and acylated quinic acids analogs from the flower budsof Prunus mume and their inhibitory effect on melanogenesisrdquoPhytochemistry vol 92 pp 128ndash136 2013
[63] K Fujimoto SNakamura TMatsumoto et al ldquoMedicinal flow-ers XXXVIII Structures of acylated sucroses and inhibitoryeffects of constituents on aldose reducatase from the flower budsofPrunusmumerdquoChemical and Pharmaceutical Bulletin vol 61no 4 pp 445ndash451 2013
[64] S Nakamura K Fujimoto T Matsumoto et al ldquoStructuresof acylated sucroses and an acylated flavonol glycoside andinhibitory effects of constituents on aldose reductase from theflower buds of Prunus mumerdquo Journal of Natural Medicines vol67 no 4 pp 799ndash806 2013
[65] L-B Dong J He X-Y Li et al ldquoChemical constituents fromthe aerial parts of Musella lasiocarpardquo Natural Products andBioprospecting vol 1 no 1 pp 41ndash47 2011
[66] Y Xiong K Z Deng Y Q Guo W Y Gao and T J ZhangldquoNew chemical constituents from the rhizomes of Sparganiumstoloniferumrdquo Archives of Pharmacal Research vol 32 no 5 pp717ndash720 2009
[67] Y Xiong K-Z Deng Y-Q Guo W-Y Gao and T-J ZhangldquoTwo new sucrose esters from Sparganium stoloniferumrdquo Jour-nal of Asian Natural Products Research vol 10 no 5 pp 425ndash428 2008
[68] B Chen N L Wang J H Huang and X S Yao ldquoIridoidand phenylpropanoid glycosides from Scrophularia ningpoensis
22 Evidence-Based Complementary and Alternative Medicine
Hemslrdquo Asian Journal of Traditional Medicines vol 2 no 3 pp119ndash123 2007
[69] H Chen Y Z Zhou L Qiao et al ldquoTwo new compounds fromCynanchum amplexicaulerdquo Journal of Asian Natural ProductsResearch vol 10 no 3 pp 248ndash251 2008
[70] C-L Chang L-J Zhang R Y Chen et al ldquoAntioxidant andanti-inflammatory phenylpropanoid derivatives from Calamusquiquesetinerviusrdquo Journal of Natural Products vol 73 no 9 pp1482ndash1488 2010
[71] Y Kawai H Kumagai H Kurihara K Yamazaki R Sawanoand N Inoue ldquo120573-Glucosidase inhibitory activities of phenyl-propanoid glycosides vanicoside A and B from Polygonumsachalinense rhizomerdquo Fitoterapia vol 77 no 6 pp 456ndash4592006
[72] P V Kiem N X Nhiem N X Cuong et al ldquoNew phenyl-propanoid esters of sucrose from Polygonum hydropiper andtheir antioxidant activityrdquo Archives of Pharmacal Research vol31 no 11 pp 1477ndash1482 2008
[73] K J Wang Y J Zhang and C R Yang ldquoAntioxidant phenolicconstituents from Fagopyrum dibotrysrdquo Journal of Ethnophar-macology vol 99 no 2 pp 259ndash264 2005
[74] N Cho J Huh H Yang et al ldquoChemical constituentsof Polygala tenuifolia roots and their inhibitory activity onlipopolysaccharide-induced nitric oxide production in BV2microgliardquo Journal of Enzyme Inhibition and Medicinal Chem-istry vol 27 no 1 pp 1ndash4 2012
[75] Q Ren C S Wu and J L Zhang ldquoUse of on-line stop-flowheart-cutting two-dimensional high performance liquid chro-matography for simultaneous determination of 12 major con-stituents in tartary buckwheat (Fagopyrum tataricum Gaertn)rdquoJournal of Chromatography A vol 1304 pp 257ndash262 2013
[76] Q Ren C S Wu Y Ren and J L Zhang ldquoCharacterizationand identification of the chemical constituents from tartarybuckwheat (Fagopyrum tataricumGaertn) by high performanceliquid chromatographyphotodiode array detectorlinear iontrap FTICR hybrid mass spectrometryrdquo Food Chemistry vol136 no 3-4 pp 1377ndash1389 2013
[77] W Li Y N Sun X T Yan et al ldquoNF-120581B inhibitory activityof sucrose fatty acid esters and related constituents fromAstragalus membranaceusrdquo Journal of Agricultural and FoodChemistry vol 61 no 29 pp 7081ndash7088 2013
[78] J T Cheng J He Y Li et al ldquoThree new sucrose fatty acid estersfrom Equisetum hiemale LrdquoHelvetica Chimica Acta vol 95 no7 pp 1158ndash1163 2012
[79] Y Jiang and P-F Tu ldquoTenuifoliose Q a new oligosaccharideester from the root of Polygala tenuifoliaWilldrdquo Journal of AsianNatural Products Research vol 5 no 4 pp 279ndash283 2003
[80] M Yoshikawa H Matsuda T Morikawa H H Xie S Naka-mura and O Muraoka ldquoPhenylethanoid oligoglycosides andacylated oligosugars with vasorelaxant activity from Cistanchetubulosardquo Bioorganic ampMedicinal Chemistry vol 14 no 22 pp7468ndash7475 2006
[81] P-F Tu H-M Shi Z-H Song Y Jiang and Y-Y ZhaoldquoChemical constituents of Cistanche sinensisrdquo Journal of AsianNatural Products Research vol 9 no 1 pp 79ndash84 2007
[82] C-L Si Y-Y Lu P-P Qin R-C Sun and Y-H Ni ldquoPhenolicextractives with chemotaxonomic significance from the bark ofPaulownia tomentosa var tomentosardquo BioResources vol 6 no4 pp 5086ndash5098 2011
[83] J Wu S Zhang Q Xiao et al ldquoPhenylethanoid and aliphaticalcohol glycosides from Acanthus ilicifoliusrdquo Phytochemistryvol 63 no 4 pp 491ndash495 2003
[84] Y Jiang and P-F Tu ldquoAnalysis of chemical constituents inCistanche speciesrdquo Journal of Chromatography A vol 1216 no11 pp 1970ndash1979 2009
[85] H Otsuka H Kuwabara and H Hoshiyama ldquoIdentification ofsucrose diesters of aryldihydronaphthalene-type lignans fromTrigonotis peduncularisand the nature of their fluorescencerdquoJournal of Natural Products vol 71 no 7 pp 1178ndash1181 2008
[86] M-R Suo J-S Yang and Q-H Liu ldquoLignan oligosaccharideesters from Eritrichium rupestrerdquo Journal of Natural Productsvol 69 no 4 pp 682ndash684 2006
[87] P-F Tu Z-H Song H-M Shi Y Jiang and Y-Y ZhaoldquoArylethyl (=phenylethanoid) glycosides and oligosaccharidefrom the stem of Cistanche tubulosardquo Helvetica Chimica Actavol 89 no 5 pp 927ndash935 2006
[88] M-H Shyr T-H Tsai and L-C Lin ldquoRossicasins A Band rosicaside F three new phenylpropanoid glycosides fromBoschniakia rossicardquoChemical and Pharmaceutical Bulletin vol54 no 2 pp 252ndash254 2006
[89] R FangNCVeitchGCKiteM J RHowes EA Porter andM S J Simmonds ldquoGlycosylated constituents of Iris fulvaandIris brevicaulisrdquoChemical amp Pharmaceutical Bulletin vol 59 no1 pp 124ndash128 2011
[90] J Fu L Zuo J Yang R Chen and D Zhang ldquoOligosaccharidepolyester and triterpenoid saponins from the roots of Polygalajaponicardquo Phytochemistry vol 69 no 7 pp 1617ndash1624 2008
[91] M-C Cheng C-Y Li H-C Ko F-N Ko Y-L Lin andT-S Wu ldquoAntidepressant principles of the roots of polygalatenuifoliardquo Journal of Natural Products vol 69 no 9 pp 1305ndash1309 2006
[92] H T Chang and P F Tu ldquoNew oligosaccharide esters andxanthone C-glucosides from Polygala telephioidesrdquo HelveticaChimica Acta vol 90 no 5 pp 944ndash950 2007
[93] J Li L Feng J Dai R Wang and T Nohara ldquoChemical con-stituents from Polygala telephioidesrdquo China Journal of ChineseMateria Medica vol 34 no 4 pp 402ndash405 2009
[94] W-P Yin T-Z Zhao and H-Y Zhang ldquoA novel oligosaccha-ride ester from Syringa pubescensrdquo Journal of Asian NaturalProducts Research vol 10 no 1 pp 95ndash100 2008
[95] M Valko D Leibfritz J Moncol M T D Cronin M Mazurand J Telser ldquoFree radicals and antioxidants in normal physio-logical functions and human diseaserdquoThe International Journalof Biochemistry amp Cell Biology vol 39 no 1 pp 44ndash84 2007
[96] D Krishnaiah R Sarbatly and R Nithyanandam ldquoA review ofthe antioxidant potential of medicinal plant speciesrdquo Food andBioproducts Processing vol 89 no 3 pp 217ndash233 2011
[97] P Liu Y Hu D-H Guo et al ldquoAntioxidant activity ofoligosaccharide ester extracted from Polygala tenuifolia roots insenescence-accelerated micerdquo Pharmaceutical Biology vol 48no 7 pp 828ndash833 2010
[98] Y Hu H-B Liao G Dai-Hong P Liu Y-Y Wang and KRahman ldquoAntidepressant-like effects of 361015840-disinapoyl sucroseon hippocampal neuronal plasticity and neurotrophic signalpathway in chronically mild stressed ratsrdquo NeurochemistryInternational vol 56 no 3 pp 461ndash465 2010
[99] Y Hu H B O Liao P Liu D-H Guo and K RahmanldquoA bioactive compound from Polygala tenuifolia regulatesefficiency of chronic stress on hypothalamic-pituitary-adrenalaxisrdquo Pharmazie vol 64 no 9 pp 605ndash608 2009
[100] A Jungbauer and SMedjakovic ldquoAnti-inflammatory propertiesof culinary herbs and spices that ameliorate the effects ofmetabolic syndromerdquoMaturitas vol 71 no 3 pp 227ndash239 2012
Evidence-Based Complementary and Alternative Medicine 23
[101] Q Xu Y Wang S Guo Z Shen and L Yang ldquoAnti-inflammatory and analgesic activity of aqueous extract of Flospopulirdquo Journal of Ethnopharmacology vol 152 no 3 pp 540ndash545 2014
[102] K S Kim D S Lee G S Bae et al ldquoThe inhibition of JNKMAPK and NF-120581B signaling by tenuifoliside A isolated fromPolygala tenuifolia in lipopolysaccharide-induced macrophagesis associated with its anti-inflammatory effectrdquo European Jour-nal of Pharmacology vol 721 no 1ndash3 pp 267ndash276 2013
[103] J-G Lee J-M Yon C Lin A Y Jung K Y Jung and S-YNamldquoCombined treatment with capsaicin and resveratrol enhancesneuroprotection against glutamate-induced toxicity in mousecerebral cortical neuronsrdquo Food and Chemical Toxicology vol50 no 11 pp 3877ndash3885 2012
[104] M L Jin S Y Park Y H Kim J-I Oh S J Lee andG Park ldquoThe neuroprotective effects of cordycepin inhibitglutamate-induced oxidative andER stress-associated apoptosisin hippocampal HT22 cellsrdquo NeuroToxicology vol 41 pp 102ndash111 2014
[105] P Liu Y Hu J Li et al ldquoProtection of SH-SY5Y neuronal cellsfrom glutamate-induced apoptosis by 36rsquo-disinapoyl sucrosea bioactive compound isolated from radix polygalardquo Journal ofBiomedicine and Biotechnology vol 2012 Article ID 728342 5pages 2012
[106] P-B Li W-L Lin Y-G Wang W Peng X-Y Cai and W-WSu ldquoAntidiabetic activities of oligosaccharides of Ophiopogonisjaponicus in experimental type 2 diabetic ratsrdquo InternationalJournal of Biological Macromolecules vol 51 no 5 pp 749ndash7552012
[107] T Liu Y M Yip L Song et al ldquoInhibiting enzymatic starchdigestion by the phenolic compound diboside A a mechanisticand in silico studyrdquo Food Research International vol 54 no 1pp 595ndash600 2013
[108] F Cote andMGHahn ldquoOligosaccharins structures and signaltransductionrdquo Plant Molecular Biology vol 26 no 5 pp 1379ndash1411 1994
[109] RACreelman and J EMullet ldquoOligosaccharins brassinolidesand jasmonates nontraditional regulators of plant growthdevelopment and gene expressionrdquo Plant Cell vol 9 no 7 pp1211ndash1223 1997
[110] L Jiao D Wan X Zhang B Li H Zhao and S LiuldquoCharacterization and immunostimulating effects on murineperitoneal macrophages of oligosaccharide isolated from Panaxginseng CAMeyerrdquo Journal of Ethnopharmacology vol 144 no3 pp 490ndash496 2012
Submit your manuscripts athttpwwwhindawicom
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Disease Markers
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Evidence-Based Complementary and Alternative Medicine
Volume 2014Hindawi Publishing Corporationhttpwwwhindawicom
Evidence-Based Complementary and Alternative Medicine 19
[29] Similarly Zhou et al evaluated the stimulating effectsof HS and OS on the root growth and saponin productionof Panax ginseng hairy roots which were induced from theplant roots infected withAgrobacterium rhizogenes strain A4The results showed that there was a maximum effect on thehairy roots growth and saponin accumulation on day 10Compared with control group the root biomass dry weightwas increased by more than 17-fold while the total saponincontent of roots increased by more than 1-fold when thesetwo oligosaccharides were added to the hairy root at a dose of30mgL [30] The above data illustrate that HS and OS couldserve as the plant growth-regulators not only in their originalspecies but also in others
38 Immunopotentiating Activity Macrophages are impor-tant targets of investigations on cytophagy cellular immunityand molecular immunology Therefore they are deemedto play a vital role in host defense comprising phagocy-tosis proteolytic processing pathogenic agent apoptosiscytokines production and foreign antigens presentation[110] The water-extracted oligosaccharides from Panax gin-seng (WGOS) exhibited better immunopotentiating activ-ity by increasing phagocytic function of macrophages andpromoting NO TNF-120572 and reactive oxygen species pro-duction [110] In addition Wan et al have obtained malto-oligosaccharides (17 119899 = 3sim8) and three oligosaccharides (213 14) from the Panax ginseng roots The in vitro bioassaypointed out thatWGOS could serve as efficacious stimulatorsof B and T lymphocytes [28] These studies provided enlight-enment that the mixture of oligosaccharides from Chineseherbalmedicine exhibits significant effect on immune system
39 Others Acetylcholinesterase (AChE) inhibitors showgood therapeutic effects onmyasthenia gravis glaucoma andAlzheimerrsquos disease through reversible enzyme inhibitionso as to increase the accumulation of acetylcholine in thesynapse and then promote and prolong the function ofacetylcholine Vanicoside B (111) showed AChE inhibitoryactivity with an IC
50of 0062mM while hydropiperoside
(42) and lapathosides C (115) and D (38) just exhibited weakenzyme inhibitory activity [43]
Wang et al has explored low molecular mass carbohy-drate polymer from Panax ginseng roots and obtained 30ethanol elution (PGO)which included peptides and oligosac-charides (17 119899 = 0sim5) identified as maltose maltotriosemaltotetraose maltopentaose maltohexaose and maltohep-taose Pharmacological experiments revealed that PGO couldsignificantly enhance the memory in scopolamine-inducedmemory deficit rats [27]
Cistanoside F (129) and kankanose (150) were isolatedfrom the Cistanche Paulownia and Acanthus genera Phar-macological experiments showed that cistanoside F andkankanose significantly exhibited vasorelaxant effects on thenoradrenaline-induced contraction of thoracic aorta fromrats [80]
4 Conclusion
Traditional Chinese medicine from natural kingdom playsan indelible role in the treatment of human diseases andit has aroused the attention of those who have engagedin medicinal pharmaceutical chemistry Therefore scientistshave made great contributions day after day to investigate thevalid chemicals from traditional Chinese medicines In thepast decades about 193 oligosaccharides and their esters havebeen identified from traditional Chinese medicinal plantsOn the one hand only a few oligosaccharides and theirmixtures were investigated and just exhibited antidepres-sant antineoplastic antidiabetic plant growth-regulatoryimmunopotentiating and enhancedmemory activitiesMoreexploratory work is still needed to excavate biological andpharmacological activities of oligosaccharides On the otherhand oligosaccharide esters exhibited multi-advantageousactivities Bioassays have revealed that antioxidant cytotoxicantineoplastic and anti-inflammatory activities are the mostnotable bioactivities Of course to search for the naturalproducts with these activities is a hotpot in the contemporarydrug research Oligosaccharide esters provide a vast treasuretrove for medical researchers After considering the currentstudies it should be taken as future directions to makemore mechanism of action studies and clinical trials tofurther evaluate its potential as new drugs Moreover thestructure-activity relationships discussed in this review willprovide reference information for further exploring theirrelationships and continually discovering the new bioactiveoligosaccharide esters
Conflict of Interests
The authors declare that there is no conflict of interestsregarding the publication of this paper
References
[1] X D Yang L J Zhang B Liang L Z Xu and S L YangldquoOligosaccharide esters isolated from plants of PolygalaceaerdquoChinese Traditional and Herbal Drugs vol 33 no 10 pp 954ndash958 2002
[2] N Ogwuru and M Adamczeski ldquoBioactive natural productsderived from Polygonum species of plants their structures andmechanisms of actionrdquo Studies in Natural Products Chemistryvol 22 pp 607ndash642 2000
[3] S Kobayashi T Miyase and H Noguchi ldquoPolyphenolic glyco-sides and oligosaccharide multiesters from the roots of Polygaladalmaisianardquo Journal of Natural Products vol 65 no 3 pp 319ndash328 2002
[4] M Takasaki S Kuroki M Kozuka and T Konoshima ldquoNewphenylpropanoid esters of sucrose from Polygonum lapathi-foliumrdquo Journal of Natural Products vol 64 no 10 pp 1305ndash1308 2001
[5] M L Zimmermann and A T Sneden ldquoVanicosides A and Bprotein kinase C inhibitors from Polygonum pensylvanicumrdquoJournal of Natural Products vol 57 no 2 pp 236ndash242 1994
[6] M Takasaki T Konoshima S Kuroki H Tokuda and HNishino ldquoCancer chemopreventive activity of phenylpropanoid
20 Evidence-Based Complementary and Alternative Medicine
esters of sucrose vanicoside B and lapathoside A from Poly-gonum lapathifoliumrdquo Cancer Letters vol 173 no 2 pp 133ndash138 2001
[7] Q Fu T Liang Z Y Li et al ldquoSeparation of carbohydrates usinghydrophilic interaction liquid chromatographyrdquo CarbohydrateResearch vol 379 pp 13ndash17 2013
[8] M F Mrozek D Zhang and D Ben-Amotz ldquoOligosaccharideidentification and mixture quantification using Raman spec-troscopy and chemometric analysisrdquo Carbohydrate Researchvol 339 no 1 pp 141ndash145 2004
[9] G S Armstrong and B Bendiak ldquoHigh-resolution four-dimen-sional carbon-correlated 1H-1H ROESY experiments employ-ing isotags and the filter diagonalization method for effectiveassignment of glycosidic linkages in oligosaccharidesrdquo Journalof Magnetic Resonance vol 181 no 1 pp 79ndash88 2006
[10] G S Armstrong V A Mandelshtam A J Shaka and BBendiak ldquoRapid high-resolution four-dimensional NMR spec-troscopy using the filter diagonalization method and its advan-tages for detailed structural elucidation of oligosaccharidesrdquoJournal of Magnetic Resonance vol 173 no 1 pp 160ndash168 2005
[11] H-M Tseng S Gattolin J Pritchard H J Newbury and DA Barrett ldquoAnalysis of mono- di- and oligosaccharides by CEusing a two-stage derivatization method and LIF detectionrdquoElectrophoresis vol 30 no 8 pp 1399ndash1405 2009
[12] N Li X Li B L Hou and D L Meng ldquoNew disaccharosidefrom Camptosorus sibiricus Ruprrdquo Natural Product Researchvol 22 no 15 pp 1379ndash1383 2008
[13] Z Zhang D Wang Y Zhao H Gao Y-H Hu and J-FHu ldquoFructose-derived carbohydrates from Alisma orientalisrdquoNatural Product Research vol 23 no 11 pp 1013ndash1020 2009
[14] X Yang Y Zhao N He and K D Croft ldquoIsolation char-acterization and immunological effects of 120572-galacto-oligo-saccharides from a new source the herb Lycopus lucidus TurczrdquoJournal of Agricultural and Food Chemistry vol 58 no 14 pp8253ndash8258 2010
[15] R X Zhang Z P Jia L Y Kong et al ldquoStachyose extractfrom Rehmannia glutinosa Libosch to lower plasma glucose innormal and diabetic rats by oral administrationrdquo Pharmazievol 59 no 7 pp 552ndash556 2004
[16] R Zhang Y Zhao Y Sun X Lu and X Yang ldquoIsolationcharacterization and hepatoprotective effects of the raffinosefamily oligosaccharides from Rehmannia glutinosa liboschrdquoJournal of Agricultural and Food Chemistry vol 61 no 32 pp7786ndash7793 2013
[17] H Li F Song Z Zheng Z Liu and S Liu ldquoCharacterization ofsaccharides and phenolic acids in the Chinese herb Tanshen byESI-FT-ICR-MS and HPLCrdquo Journal of Mass Spectrometry vol43 no 11 pp 1545ndash1552 2008
[18] J E Deng J Zhang XM ChenW Ke and G Y Tian ldquoStudieson the physicochemical properties structure and antitumoractivity of an oligosaccharide homologue SnS-2 from the root ofScrophularia ningpoensis Hemslrdquo Chinese Journal of Chemistryvol 22 no 5 pp 492ndash497 2004
[19] S C Chou LM Chuang and S S Lee ldquoHypoglycemic constit-uents of gynura divaricata subsp formosanardquo Natural ProductCommunications vol 7 no 2 pp 221ndash222 2012
[20] F Feng L-L Wang X-P Lai Y-B Li Z-M Cao and Y-J Zhou ldquoStudy on oligosaccharides from Morinda officinalisrdquoJournal of Chinese Medicinal Materials vol 35 no 8 pp 1259ndash1262 2012
[21] Y F Li Z H Gong M Yang Y M Zhao and Z P Luo ldquoInhibi-tion of the oligosaccharides extracted fromMorinda officinalis
a Chinese traditional herbal medicine on the corticosteroneinduced apoptosis in PC12 cellsrdquo Life Sciences vol 72 no 8 pp933ndash942 2003
[22] Y-F Li Y-Q Liu M Yang et al ldquoThe cytoprotective effect ofinulin-type hexasaccharide extracted from Morinda officinalison PC12 cells against the lesion induced by corticosteronerdquo LifeSciences vol 75 no 13 pp 1531ndash1538 2004
[23] D N Olennikov L M Tankhaeva and A V Rokhin ldquoGlu-cofructans from Saussurea lappa rootsrdquo Chemistry of NaturalCompounds vol 47 no 3 pp 339ndash342 2011
[24] S K Hyun H A Jung B S Min J H Jung and J S ChoildquoIsolation of phenolics nucleosides saccharides and an alkaloidfrom the root of Aralia cordatardquo Natural Product Sciences vol16 no 1 pp 20ndash25 2010
[25] Z J Xu C W Lin and M F Liao ldquoStructure analysis of a newoligosaccharides BROS from Blumea ripariardquo Chinese Journalof Organic Chemistry vol 31 no 11 pp 1811ndash1819 2011
[26] Z J Xu C W Lin and Y Shi ldquoIsolation and structuredetermination of a new oligosaccharide from Blume ripariardquoJournal of Medicinal Plants Research vol 5 no 14 pp 2956ndash2962 2011
[27] Y Wang R Z Jiang G R Li et al ldquoStructural and enhancedmemory activity studies of extracts from Panax ginseng rootrdquoFood Chemistry vol 119 no 3 pp 969ndash973 2010
[28] DWan L Jiao H Yang and S Liu ldquoStructural characterizationand immunological activities of the water-soluble oligosaccha-rides isolated from thePanax ginseng rootsrdquoPlanta vol 235 no6 pp 1289ndash1297 2012
[29] L G Zhou C Z Yang J Q Li S L Wang and J Y WuldquoHeptasaccharide and octasaccharide isolated from Paris pol-yphylla var yunnanensis and their plant growth-regulatoryactivityrdquo Plant Science vol 165 no 3 pp 571ndash575 2003
[30] L G Zhou X D Cao R F Zhang Y L Peng S J Zhao andJ Y Wu ldquoStimulation of saponin production in Panax ginsenghairy roots by two oligosaccharides from Paris polyphylla varyunnanensisrdquo Biotechnology Letters vol 29 no 4 pp 631ndash6342007
[31] M Vanhaecke W van den Ende E Lescrinier and N Dyu-bankova ldquoIsolation and characterization of a pentasaccharidefrom Stellaria mediardquo Journal of Natural Products vol 71 no 11pp 1833ndash1836 2008
[32] J Feng and W Zhao ldquoComplete 1Hand 13C NMR assignmentsof four new oligosaccharides and two new glycosides fromPeriploca forrestiirdquoMagnetic Resonance in Chemistry vol 47 no8 pp 701ndash705 2009
[33] J Q Feng R J Zhang Y Zhou et al ldquoImmunosuppressive preg-nane glycosides from Periploca sepium and Periploca forrestiirdquoPhytochemistry vol 69 no 15 pp 2716ndash2723 2008
[34] X H Long R Xu Y H Zhang X H Tan andQ Y Sun ldquoA newoligosaccharide from Periploca calophyllardquo Zhongguo ZhongyaoZazhi vol 37 no 2 pp 226ndash229 2012
[35] L Wang Z-Q Yin Y Wang X-Q Zhang Y-L Li and W-CYe ldquoPerisesaccharides A-E new oligosaccharides from the rootbarks ofPeriploca sepiumrdquoPlantaMedica vol 76 no 9 pp 909ndash915 2010
[36] T Lei L Zhang H-Y Jiang Y Hu A-H Hong and Y-Z CenldquoA new pregnane glycoside and oligosaccharide from Parabar-ium huaitingiirdquo Journal of Asian Natural Products Research vol13 no 11 pp 1030ndash1035 2011
[37] J Li Y Jiang and P F Tu ldquoTricornoses A-L oligosaccharidemulti-esters from the roots of Polygala tricornisrdquo Journal ofNatural Products vol 68 no 5 pp 739ndash744 2005
Evidence-Based Complementary and Alternative Medicine 21
[38] H H Tu P Liu L Mu et al ldquoStudy on antidepressant com-ponents of sucrose ester from Polygala tenuifoliardquo ZhongguoZhongyao Zazhi vol 33 no 11 pp 1278ndash1280 2008
[39] G M She Y Y Ba Y Liu H Lv W Wang and R B ShildquoAbsorbable phenylpropenoyl sucroses from Polygala tenuifo-liardquoMolecules vol 16 no 7 pp 5507ndash5513 2011
[40] J Yong and P F Tu ldquoStudies on the chemical constituents inroot bark of Polygala tenuifolia (II)rdquo China Journal of ChineseMateria Medica vol 29 no 8 pp 751ndash753 2004
[41] M Ono C Takamura F Sugita et al ldquoTwo new steroidglycosides and a new sesquiterpenoid glycoside from theunderground parts of Trillium kamtschaticumrdquo Chemical andPharmaceutical Bulletin vol 55 no 4 pp 551ndash556 2007
[42] Y Ling Z Li M Chen Z Sun M Fan and C HuangldquoAnalysis and detection of the chemical constituents of RadixPolygalae and their metabolites in rats after oral administrationby ultra high-performance liquid chromatography coupledwith electrospray ionization quadrupole time-of-flight tandemmass spectrometryrdquo Journal of Pharmaceutical and BiomedicalAnalysis vol 85 pp 1ndash13 2013
[43] P Fan L Terrier A-E Hay A Marston and K HostettmannldquoAntioxidant and enzyme inhibition activities and chemicalprofiles ofPolygonum sachalinensis FSchmidt exMaxim (Polyg-onaceae)rdquo Fitoterapia vol 81 no 2 pp 124ndash131 2010
[44] L J Zhang C C Liao H C Huang Y C Shen L M Yangand Y H Kuo ldquoAntioxidant phenylpropanoid glycosides fromSmilax bracteatardquo Phytochemistry vol 69 no 6 pp 1398ndash14042008
[45] L L Yan W Y Gao Y J Zhang and Y Wang ldquoA new phenyl-propanoid glycosides from Paris polyphylla var yunnanensisrdquoFitoterapia vol 79 no 4 pp 306ndash307 2008
[46] Y H Kuo Y W Hsu C C Liaw J K Lee H C Huang andL M Y Kuo ldquoCytotoxic phenylpropanoid glycosides from thestems of Smilax chinardquo Journal of Natural Products vol 68 no10 pp 1475ndash1478 2005
[47] W-X Wang T-X Li H Ma J-F Zhang and A-Q JialdquoTumoral cytotoxic and antioxidative phenylpropanoid glyco-sides in Smilax riparia A DCrdquo Journal of Ethnopharmacologyvol 149 no 2 pp 527ndash532 2013
[48] N X Nhiem P vanKiem C vanMinh et al ldquoPhenylpropanoidglycosides fromHeterosmilax erythrantha and their antioxidantactivityrdquo Archives of Pharmacal Research vol 32 no 10 pp1373ndash1377 2009
[49] Y Wang W Y Gao T J Zhang and Y Q Guo ldquoA novelphenylpropanoid glycosides and a new derivation of phenolicglycoside from Paris Polyphylla var yunnanensisrdquo ChineseChemical Letters vol 18 no 5 pp 548ndash550 2007
[50] J-Y Zhang Y-Z Wang Y-L Zhao et al ldquoPhytochemicals andbioactivities of Paris speciesrdquo Journal of Asian Natural ProductsResearch vol 13 no 7 pp 670ndash681 2011
[51] N H N Hashim F Abas K Shaari and N H Lajis ldquoLC-DAD-ESIMSMS characterization of antioxidant and anti-cholinesterase constituents present in the active fraction fromPersicaria hydropiperrdquo LWT Food Science and Technology vol46 no 2 pp 468ndash476 2012
[52] PH FanA EHayAMarstonHX Lou andKHostettmannldquoChemical variability of the invasive neophytes Polygonumcuspidatum Sieb and Zucc and Polygonum sachalinensis FSchmidt ex Maximrdquo Biochemical Systematics and Ecology vol37 no 1 pp 24ndash34 2009
[53] P Liu Y Hu D H Guo et al ldquoPotential antidepressantproperties of Radix Polygalae (Yuan Zhi)rdquo Phytomedicine vol17 no 10 pp 794ndash799 2010
[54] J F Wu S B Chen S L Chen and P F Tu ldquoThe chemical con-stituents of Polygala hongkongensisHemslrdquoActa PharmaceuticaSinica vol 42 no 7 pp 757ndash761 2007
[55] Y Song Y Jiang D Bi X Tian L Liang and P Tu ldquoChemicalconstituents from n-butanol extract of aerial part of Polygalasibiricardquo Zhongguo Zhongyao Zazhi vol 37 no 4 pp 471ndash4742012
[56] Y Ikeya S Takeda M Tunakawa et al ldquoCognitive improvingand cerebral protective effects of acylated oligosaccharides inPolygala tenuifoliardquo Biological and Pharmaceutical Bulletin vol27 no 7 pp 1081ndash1085 2004
[57] C J Zheng C L Hu X Q Ma C Peng H Zhang and L PQin ldquoCytotoxic phenylpropanoid glycosides from Fagopyrumtataricum (L) Gaertnrdquo Food Chemistry vol 132 no 1 pp 433ndash438 2012
[58] X Li Y F Zhang L Yang et al ldquoChemical profiling ofconstituents of Smilacis glabrae using ultra-high pressure liquidchromatography coupled with LTQ orbitrap mass spectrome-tryrdquo Natural Product Communications vol 7 no 2 pp 181ndash1842012
[59] T-T Sun D-W Zhang Y Han F-Y Dong andWWang ldquoSmi-lasides M and N two new phenylpropanoid glycosides fromSmilax ripariardquo Journal of Asian Natural Products Research vol14 no 2 pp 165ndash170 2012
[60] J Li X Bi G Zheng Y Hitoshi T Ikeda and T NoharaldquoSteroidal glycosides and aromatic compounds from Smilaxripariardquo Chemical amp Pharmaceutical Bulletin vol 54 no 10 pp1451ndash1454 2006
[61] N Wang X Yao R Ishii and S Kitanaka ldquoBioactive sucroseesters from Bidens parviflorardquo Phytochemistry vol 62 no 5 pp741ndash746 2003
[62] S Nakamura K Fujimoto T Matsumoto et al ldquoAcylatedsucroses and acylated quinic acids analogs from the flower budsof Prunus mume and their inhibitory effect on melanogenesisrdquoPhytochemistry vol 92 pp 128ndash136 2013
[63] K Fujimoto SNakamura TMatsumoto et al ldquoMedicinal flow-ers XXXVIII Structures of acylated sucroses and inhibitoryeffects of constituents on aldose reducatase from the flower budsofPrunusmumerdquoChemical and Pharmaceutical Bulletin vol 61no 4 pp 445ndash451 2013
[64] S Nakamura K Fujimoto T Matsumoto et al ldquoStructuresof acylated sucroses and an acylated flavonol glycoside andinhibitory effects of constituents on aldose reductase from theflower buds of Prunus mumerdquo Journal of Natural Medicines vol67 no 4 pp 799ndash806 2013
[65] L-B Dong J He X-Y Li et al ldquoChemical constituents fromthe aerial parts of Musella lasiocarpardquo Natural Products andBioprospecting vol 1 no 1 pp 41ndash47 2011
[66] Y Xiong K Z Deng Y Q Guo W Y Gao and T J ZhangldquoNew chemical constituents from the rhizomes of Sparganiumstoloniferumrdquo Archives of Pharmacal Research vol 32 no 5 pp717ndash720 2009
[67] Y Xiong K-Z Deng Y-Q Guo W-Y Gao and T-J ZhangldquoTwo new sucrose esters from Sparganium stoloniferumrdquo Jour-nal of Asian Natural Products Research vol 10 no 5 pp 425ndash428 2008
[68] B Chen N L Wang J H Huang and X S Yao ldquoIridoidand phenylpropanoid glycosides from Scrophularia ningpoensis
22 Evidence-Based Complementary and Alternative Medicine
Hemslrdquo Asian Journal of Traditional Medicines vol 2 no 3 pp119ndash123 2007
[69] H Chen Y Z Zhou L Qiao et al ldquoTwo new compounds fromCynanchum amplexicaulerdquo Journal of Asian Natural ProductsResearch vol 10 no 3 pp 248ndash251 2008
[70] C-L Chang L-J Zhang R Y Chen et al ldquoAntioxidant andanti-inflammatory phenylpropanoid derivatives from Calamusquiquesetinerviusrdquo Journal of Natural Products vol 73 no 9 pp1482ndash1488 2010
[71] Y Kawai H Kumagai H Kurihara K Yamazaki R Sawanoand N Inoue ldquo120573-Glucosidase inhibitory activities of phenyl-propanoid glycosides vanicoside A and B from Polygonumsachalinense rhizomerdquo Fitoterapia vol 77 no 6 pp 456ndash4592006
[72] P V Kiem N X Nhiem N X Cuong et al ldquoNew phenyl-propanoid esters of sucrose from Polygonum hydropiper andtheir antioxidant activityrdquo Archives of Pharmacal Research vol31 no 11 pp 1477ndash1482 2008
[73] K J Wang Y J Zhang and C R Yang ldquoAntioxidant phenolicconstituents from Fagopyrum dibotrysrdquo Journal of Ethnophar-macology vol 99 no 2 pp 259ndash264 2005
[74] N Cho J Huh H Yang et al ldquoChemical constituentsof Polygala tenuifolia roots and their inhibitory activity onlipopolysaccharide-induced nitric oxide production in BV2microgliardquo Journal of Enzyme Inhibition and Medicinal Chem-istry vol 27 no 1 pp 1ndash4 2012
[75] Q Ren C S Wu and J L Zhang ldquoUse of on-line stop-flowheart-cutting two-dimensional high performance liquid chro-matography for simultaneous determination of 12 major con-stituents in tartary buckwheat (Fagopyrum tataricum Gaertn)rdquoJournal of Chromatography A vol 1304 pp 257ndash262 2013
[76] Q Ren C S Wu Y Ren and J L Zhang ldquoCharacterizationand identification of the chemical constituents from tartarybuckwheat (Fagopyrum tataricumGaertn) by high performanceliquid chromatographyphotodiode array detectorlinear iontrap FTICR hybrid mass spectrometryrdquo Food Chemistry vol136 no 3-4 pp 1377ndash1389 2013
[77] W Li Y N Sun X T Yan et al ldquoNF-120581B inhibitory activityof sucrose fatty acid esters and related constituents fromAstragalus membranaceusrdquo Journal of Agricultural and FoodChemistry vol 61 no 29 pp 7081ndash7088 2013
[78] J T Cheng J He Y Li et al ldquoThree new sucrose fatty acid estersfrom Equisetum hiemale LrdquoHelvetica Chimica Acta vol 95 no7 pp 1158ndash1163 2012
[79] Y Jiang and P-F Tu ldquoTenuifoliose Q a new oligosaccharideester from the root of Polygala tenuifoliaWilldrdquo Journal of AsianNatural Products Research vol 5 no 4 pp 279ndash283 2003
[80] M Yoshikawa H Matsuda T Morikawa H H Xie S Naka-mura and O Muraoka ldquoPhenylethanoid oligoglycosides andacylated oligosugars with vasorelaxant activity from Cistanchetubulosardquo Bioorganic ampMedicinal Chemistry vol 14 no 22 pp7468ndash7475 2006
[81] P-F Tu H-M Shi Z-H Song Y Jiang and Y-Y ZhaoldquoChemical constituents of Cistanche sinensisrdquo Journal of AsianNatural Products Research vol 9 no 1 pp 79ndash84 2007
[82] C-L Si Y-Y Lu P-P Qin R-C Sun and Y-H Ni ldquoPhenolicextractives with chemotaxonomic significance from the bark ofPaulownia tomentosa var tomentosardquo BioResources vol 6 no4 pp 5086ndash5098 2011
[83] J Wu S Zhang Q Xiao et al ldquoPhenylethanoid and aliphaticalcohol glycosides from Acanthus ilicifoliusrdquo Phytochemistryvol 63 no 4 pp 491ndash495 2003
[84] Y Jiang and P-F Tu ldquoAnalysis of chemical constituents inCistanche speciesrdquo Journal of Chromatography A vol 1216 no11 pp 1970ndash1979 2009
[85] H Otsuka H Kuwabara and H Hoshiyama ldquoIdentification ofsucrose diesters of aryldihydronaphthalene-type lignans fromTrigonotis peduncularisand the nature of their fluorescencerdquoJournal of Natural Products vol 71 no 7 pp 1178ndash1181 2008
[86] M-R Suo J-S Yang and Q-H Liu ldquoLignan oligosaccharideesters from Eritrichium rupestrerdquo Journal of Natural Productsvol 69 no 4 pp 682ndash684 2006
[87] P-F Tu Z-H Song H-M Shi Y Jiang and Y-Y ZhaoldquoArylethyl (=phenylethanoid) glycosides and oligosaccharidefrom the stem of Cistanche tubulosardquo Helvetica Chimica Actavol 89 no 5 pp 927ndash935 2006
[88] M-H Shyr T-H Tsai and L-C Lin ldquoRossicasins A Band rosicaside F three new phenylpropanoid glycosides fromBoschniakia rossicardquoChemical and Pharmaceutical Bulletin vol54 no 2 pp 252ndash254 2006
[89] R FangNCVeitchGCKiteM J RHowes EA Porter andM S J Simmonds ldquoGlycosylated constituents of Iris fulvaandIris brevicaulisrdquoChemical amp Pharmaceutical Bulletin vol 59 no1 pp 124ndash128 2011
[90] J Fu L Zuo J Yang R Chen and D Zhang ldquoOligosaccharidepolyester and triterpenoid saponins from the roots of Polygalajaponicardquo Phytochemistry vol 69 no 7 pp 1617ndash1624 2008
[91] M-C Cheng C-Y Li H-C Ko F-N Ko Y-L Lin andT-S Wu ldquoAntidepressant principles of the roots of polygalatenuifoliardquo Journal of Natural Products vol 69 no 9 pp 1305ndash1309 2006
[92] H T Chang and P F Tu ldquoNew oligosaccharide esters andxanthone C-glucosides from Polygala telephioidesrdquo HelveticaChimica Acta vol 90 no 5 pp 944ndash950 2007
[93] J Li L Feng J Dai R Wang and T Nohara ldquoChemical con-stituents from Polygala telephioidesrdquo China Journal of ChineseMateria Medica vol 34 no 4 pp 402ndash405 2009
[94] W-P Yin T-Z Zhao and H-Y Zhang ldquoA novel oligosaccha-ride ester from Syringa pubescensrdquo Journal of Asian NaturalProducts Research vol 10 no 1 pp 95ndash100 2008
[95] M Valko D Leibfritz J Moncol M T D Cronin M Mazurand J Telser ldquoFree radicals and antioxidants in normal physio-logical functions and human diseaserdquoThe International Journalof Biochemistry amp Cell Biology vol 39 no 1 pp 44ndash84 2007
[96] D Krishnaiah R Sarbatly and R Nithyanandam ldquoA review ofthe antioxidant potential of medicinal plant speciesrdquo Food andBioproducts Processing vol 89 no 3 pp 217ndash233 2011
[97] P Liu Y Hu D-H Guo et al ldquoAntioxidant activity ofoligosaccharide ester extracted from Polygala tenuifolia roots insenescence-accelerated micerdquo Pharmaceutical Biology vol 48no 7 pp 828ndash833 2010
[98] Y Hu H-B Liao G Dai-Hong P Liu Y-Y Wang and KRahman ldquoAntidepressant-like effects of 361015840-disinapoyl sucroseon hippocampal neuronal plasticity and neurotrophic signalpathway in chronically mild stressed ratsrdquo NeurochemistryInternational vol 56 no 3 pp 461ndash465 2010
[99] Y Hu H B O Liao P Liu D-H Guo and K RahmanldquoA bioactive compound from Polygala tenuifolia regulatesefficiency of chronic stress on hypothalamic-pituitary-adrenalaxisrdquo Pharmazie vol 64 no 9 pp 605ndash608 2009
[100] A Jungbauer and SMedjakovic ldquoAnti-inflammatory propertiesof culinary herbs and spices that ameliorate the effects ofmetabolic syndromerdquoMaturitas vol 71 no 3 pp 227ndash239 2012
Evidence-Based Complementary and Alternative Medicine 23
[101] Q Xu Y Wang S Guo Z Shen and L Yang ldquoAnti-inflammatory and analgesic activity of aqueous extract of Flospopulirdquo Journal of Ethnopharmacology vol 152 no 3 pp 540ndash545 2014
[102] K S Kim D S Lee G S Bae et al ldquoThe inhibition of JNKMAPK and NF-120581B signaling by tenuifoliside A isolated fromPolygala tenuifolia in lipopolysaccharide-induced macrophagesis associated with its anti-inflammatory effectrdquo European Jour-nal of Pharmacology vol 721 no 1ndash3 pp 267ndash276 2013
[103] J-G Lee J-M Yon C Lin A Y Jung K Y Jung and S-YNamldquoCombined treatment with capsaicin and resveratrol enhancesneuroprotection against glutamate-induced toxicity in mousecerebral cortical neuronsrdquo Food and Chemical Toxicology vol50 no 11 pp 3877ndash3885 2012
[104] M L Jin S Y Park Y H Kim J-I Oh S J Lee andG Park ldquoThe neuroprotective effects of cordycepin inhibitglutamate-induced oxidative andER stress-associated apoptosisin hippocampal HT22 cellsrdquo NeuroToxicology vol 41 pp 102ndash111 2014
[105] P Liu Y Hu J Li et al ldquoProtection of SH-SY5Y neuronal cellsfrom glutamate-induced apoptosis by 36rsquo-disinapoyl sucrosea bioactive compound isolated from radix polygalardquo Journal ofBiomedicine and Biotechnology vol 2012 Article ID 728342 5pages 2012
[106] P-B Li W-L Lin Y-G Wang W Peng X-Y Cai and W-WSu ldquoAntidiabetic activities of oligosaccharides of Ophiopogonisjaponicus in experimental type 2 diabetic ratsrdquo InternationalJournal of Biological Macromolecules vol 51 no 5 pp 749ndash7552012
[107] T Liu Y M Yip L Song et al ldquoInhibiting enzymatic starchdigestion by the phenolic compound diboside A a mechanisticand in silico studyrdquo Food Research International vol 54 no 1pp 595ndash600 2013
[108] F Cote andMGHahn ldquoOligosaccharins structures and signaltransductionrdquo Plant Molecular Biology vol 26 no 5 pp 1379ndash1411 1994
[109] RACreelman and J EMullet ldquoOligosaccharins brassinolidesand jasmonates nontraditional regulators of plant growthdevelopment and gene expressionrdquo Plant Cell vol 9 no 7 pp1211ndash1223 1997
[110] L Jiao D Wan X Zhang B Li H Zhao and S LiuldquoCharacterization and immunostimulating effects on murineperitoneal macrophages of oligosaccharide isolated from Panaxginseng CAMeyerrdquo Journal of Ethnopharmacology vol 144 no3 pp 490ndash496 2012
Submit your manuscripts athttpwwwhindawicom
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Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
MEDIATORSINFLAMMATION
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Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
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EndocrinologyInternational Journal of
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Disease Markers
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
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OncologyJournal of
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Oxidative Medicine and Cellular Longevity
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
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The Scientific World JournalHindawi Publishing Corporation httpwwwhindawicom Volume 2014
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Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
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Research and TreatmentAIDS
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
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Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Parkinsonrsquos Disease
Evidence-Based Complementary and Alternative Medicine
Volume 2014Hindawi Publishing Corporationhttpwwwhindawicom
20 Evidence-Based Complementary and Alternative Medicine
esters of sucrose vanicoside B and lapathoside A from Poly-gonum lapathifoliumrdquo Cancer Letters vol 173 no 2 pp 133ndash138 2001
[7] Q Fu T Liang Z Y Li et al ldquoSeparation of carbohydrates usinghydrophilic interaction liquid chromatographyrdquo CarbohydrateResearch vol 379 pp 13ndash17 2013
[8] M F Mrozek D Zhang and D Ben-Amotz ldquoOligosaccharideidentification and mixture quantification using Raman spec-troscopy and chemometric analysisrdquo Carbohydrate Researchvol 339 no 1 pp 141ndash145 2004
[9] G S Armstrong and B Bendiak ldquoHigh-resolution four-dimen-sional carbon-correlated 1H-1H ROESY experiments employ-ing isotags and the filter diagonalization method for effectiveassignment of glycosidic linkages in oligosaccharidesrdquo Journalof Magnetic Resonance vol 181 no 1 pp 79ndash88 2006
[10] G S Armstrong V A Mandelshtam A J Shaka and BBendiak ldquoRapid high-resolution four-dimensional NMR spec-troscopy using the filter diagonalization method and its advan-tages for detailed structural elucidation of oligosaccharidesrdquoJournal of Magnetic Resonance vol 173 no 1 pp 160ndash168 2005
[11] H-M Tseng S Gattolin J Pritchard H J Newbury and DA Barrett ldquoAnalysis of mono- di- and oligosaccharides by CEusing a two-stage derivatization method and LIF detectionrdquoElectrophoresis vol 30 no 8 pp 1399ndash1405 2009
[12] N Li X Li B L Hou and D L Meng ldquoNew disaccharosidefrom Camptosorus sibiricus Ruprrdquo Natural Product Researchvol 22 no 15 pp 1379ndash1383 2008
[13] Z Zhang D Wang Y Zhao H Gao Y-H Hu and J-FHu ldquoFructose-derived carbohydrates from Alisma orientalisrdquoNatural Product Research vol 23 no 11 pp 1013ndash1020 2009
[14] X Yang Y Zhao N He and K D Croft ldquoIsolation char-acterization and immunological effects of 120572-galacto-oligo-saccharides from a new source the herb Lycopus lucidus TurczrdquoJournal of Agricultural and Food Chemistry vol 58 no 14 pp8253ndash8258 2010
[15] R X Zhang Z P Jia L Y Kong et al ldquoStachyose extractfrom Rehmannia glutinosa Libosch to lower plasma glucose innormal and diabetic rats by oral administrationrdquo Pharmazievol 59 no 7 pp 552ndash556 2004
[16] R Zhang Y Zhao Y Sun X Lu and X Yang ldquoIsolationcharacterization and hepatoprotective effects of the raffinosefamily oligosaccharides from Rehmannia glutinosa liboschrdquoJournal of Agricultural and Food Chemistry vol 61 no 32 pp7786ndash7793 2013
[17] H Li F Song Z Zheng Z Liu and S Liu ldquoCharacterization ofsaccharides and phenolic acids in the Chinese herb Tanshen byESI-FT-ICR-MS and HPLCrdquo Journal of Mass Spectrometry vol43 no 11 pp 1545ndash1552 2008
[18] J E Deng J Zhang XM ChenW Ke and G Y Tian ldquoStudieson the physicochemical properties structure and antitumoractivity of an oligosaccharide homologue SnS-2 from the root ofScrophularia ningpoensis Hemslrdquo Chinese Journal of Chemistryvol 22 no 5 pp 492ndash497 2004
[19] S C Chou LM Chuang and S S Lee ldquoHypoglycemic constit-uents of gynura divaricata subsp formosanardquo Natural ProductCommunications vol 7 no 2 pp 221ndash222 2012
[20] F Feng L-L Wang X-P Lai Y-B Li Z-M Cao and Y-J Zhou ldquoStudy on oligosaccharides from Morinda officinalisrdquoJournal of Chinese Medicinal Materials vol 35 no 8 pp 1259ndash1262 2012
[21] Y F Li Z H Gong M Yang Y M Zhao and Z P Luo ldquoInhibi-tion of the oligosaccharides extracted fromMorinda officinalis
a Chinese traditional herbal medicine on the corticosteroneinduced apoptosis in PC12 cellsrdquo Life Sciences vol 72 no 8 pp933ndash942 2003
[22] Y-F Li Y-Q Liu M Yang et al ldquoThe cytoprotective effect ofinulin-type hexasaccharide extracted from Morinda officinalison PC12 cells against the lesion induced by corticosteronerdquo LifeSciences vol 75 no 13 pp 1531ndash1538 2004
[23] D N Olennikov L M Tankhaeva and A V Rokhin ldquoGlu-cofructans from Saussurea lappa rootsrdquo Chemistry of NaturalCompounds vol 47 no 3 pp 339ndash342 2011
[24] S K Hyun H A Jung B S Min J H Jung and J S ChoildquoIsolation of phenolics nucleosides saccharides and an alkaloidfrom the root of Aralia cordatardquo Natural Product Sciences vol16 no 1 pp 20ndash25 2010
[25] Z J Xu C W Lin and M F Liao ldquoStructure analysis of a newoligosaccharides BROS from Blumea ripariardquo Chinese Journalof Organic Chemistry vol 31 no 11 pp 1811ndash1819 2011
[26] Z J Xu C W Lin and Y Shi ldquoIsolation and structuredetermination of a new oligosaccharide from Blume ripariardquoJournal of Medicinal Plants Research vol 5 no 14 pp 2956ndash2962 2011
[27] Y Wang R Z Jiang G R Li et al ldquoStructural and enhancedmemory activity studies of extracts from Panax ginseng rootrdquoFood Chemistry vol 119 no 3 pp 969ndash973 2010
[28] DWan L Jiao H Yang and S Liu ldquoStructural characterizationand immunological activities of the water-soluble oligosaccha-rides isolated from thePanax ginseng rootsrdquoPlanta vol 235 no6 pp 1289ndash1297 2012
[29] L G Zhou C Z Yang J Q Li S L Wang and J Y WuldquoHeptasaccharide and octasaccharide isolated from Paris pol-yphylla var yunnanensis and their plant growth-regulatoryactivityrdquo Plant Science vol 165 no 3 pp 571ndash575 2003
[30] L G Zhou X D Cao R F Zhang Y L Peng S J Zhao andJ Y Wu ldquoStimulation of saponin production in Panax ginsenghairy roots by two oligosaccharides from Paris polyphylla varyunnanensisrdquo Biotechnology Letters vol 29 no 4 pp 631ndash6342007
[31] M Vanhaecke W van den Ende E Lescrinier and N Dyu-bankova ldquoIsolation and characterization of a pentasaccharidefrom Stellaria mediardquo Journal of Natural Products vol 71 no 11pp 1833ndash1836 2008
[32] J Feng and W Zhao ldquoComplete 1Hand 13C NMR assignmentsof four new oligosaccharides and two new glycosides fromPeriploca forrestiirdquoMagnetic Resonance in Chemistry vol 47 no8 pp 701ndash705 2009
[33] J Q Feng R J Zhang Y Zhou et al ldquoImmunosuppressive preg-nane glycosides from Periploca sepium and Periploca forrestiirdquoPhytochemistry vol 69 no 15 pp 2716ndash2723 2008
[34] X H Long R Xu Y H Zhang X H Tan andQ Y Sun ldquoA newoligosaccharide from Periploca calophyllardquo Zhongguo ZhongyaoZazhi vol 37 no 2 pp 226ndash229 2012
[35] L Wang Z-Q Yin Y Wang X-Q Zhang Y-L Li and W-CYe ldquoPerisesaccharides A-E new oligosaccharides from the rootbarks ofPeriploca sepiumrdquoPlantaMedica vol 76 no 9 pp 909ndash915 2010
[36] T Lei L Zhang H-Y Jiang Y Hu A-H Hong and Y-Z CenldquoA new pregnane glycoside and oligosaccharide from Parabar-ium huaitingiirdquo Journal of Asian Natural Products Research vol13 no 11 pp 1030ndash1035 2011
[37] J Li Y Jiang and P F Tu ldquoTricornoses A-L oligosaccharidemulti-esters from the roots of Polygala tricornisrdquo Journal ofNatural Products vol 68 no 5 pp 739ndash744 2005
Evidence-Based Complementary and Alternative Medicine 21
[38] H H Tu P Liu L Mu et al ldquoStudy on antidepressant com-ponents of sucrose ester from Polygala tenuifoliardquo ZhongguoZhongyao Zazhi vol 33 no 11 pp 1278ndash1280 2008
[39] G M She Y Y Ba Y Liu H Lv W Wang and R B ShildquoAbsorbable phenylpropenoyl sucroses from Polygala tenuifo-liardquoMolecules vol 16 no 7 pp 5507ndash5513 2011
[40] J Yong and P F Tu ldquoStudies on the chemical constituents inroot bark of Polygala tenuifolia (II)rdquo China Journal of ChineseMateria Medica vol 29 no 8 pp 751ndash753 2004
[41] M Ono C Takamura F Sugita et al ldquoTwo new steroidglycosides and a new sesquiterpenoid glycoside from theunderground parts of Trillium kamtschaticumrdquo Chemical andPharmaceutical Bulletin vol 55 no 4 pp 551ndash556 2007
[42] Y Ling Z Li M Chen Z Sun M Fan and C HuangldquoAnalysis and detection of the chemical constituents of RadixPolygalae and their metabolites in rats after oral administrationby ultra high-performance liquid chromatography coupledwith electrospray ionization quadrupole time-of-flight tandemmass spectrometryrdquo Journal of Pharmaceutical and BiomedicalAnalysis vol 85 pp 1ndash13 2013
[43] P Fan L Terrier A-E Hay A Marston and K HostettmannldquoAntioxidant and enzyme inhibition activities and chemicalprofiles ofPolygonum sachalinensis FSchmidt exMaxim (Polyg-onaceae)rdquo Fitoterapia vol 81 no 2 pp 124ndash131 2010
[44] L J Zhang C C Liao H C Huang Y C Shen L M Yangand Y H Kuo ldquoAntioxidant phenylpropanoid glycosides fromSmilax bracteatardquo Phytochemistry vol 69 no 6 pp 1398ndash14042008
[45] L L Yan W Y Gao Y J Zhang and Y Wang ldquoA new phenyl-propanoid glycosides from Paris polyphylla var yunnanensisrdquoFitoterapia vol 79 no 4 pp 306ndash307 2008
[46] Y H Kuo Y W Hsu C C Liaw J K Lee H C Huang andL M Y Kuo ldquoCytotoxic phenylpropanoid glycosides from thestems of Smilax chinardquo Journal of Natural Products vol 68 no10 pp 1475ndash1478 2005
[47] W-X Wang T-X Li H Ma J-F Zhang and A-Q JialdquoTumoral cytotoxic and antioxidative phenylpropanoid glyco-sides in Smilax riparia A DCrdquo Journal of Ethnopharmacologyvol 149 no 2 pp 527ndash532 2013
[48] N X Nhiem P vanKiem C vanMinh et al ldquoPhenylpropanoidglycosides fromHeterosmilax erythrantha and their antioxidantactivityrdquo Archives of Pharmacal Research vol 32 no 10 pp1373ndash1377 2009
[49] Y Wang W Y Gao T J Zhang and Y Q Guo ldquoA novelphenylpropanoid glycosides and a new derivation of phenolicglycoside from Paris Polyphylla var yunnanensisrdquo ChineseChemical Letters vol 18 no 5 pp 548ndash550 2007
[50] J-Y Zhang Y-Z Wang Y-L Zhao et al ldquoPhytochemicals andbioactivities of Paris speciesrdquo Journal of Asian Natural ProductsResearch vol 13 no 7 pp 670ndash681 2011
[51] N H N Hashim F Abas K Shaari and N H Lajis ldquoLC-DAD-ESIMSMS characterization of antioxidant and anti-cholinesterase constituents present in the active fraction fromPersicaria hydropiperrdquo LWT Food Science and Technology vol46 no 2 pp 468ndash476 2012
[52] PH FanA EHayAMarstonHX Lou andKHostettmannldquoChemical variability of the invasive neophytes Polygonumcuspidatum Sieb and Zucc and Polygonum sachalinensis FSchmidt ex Maximrdquo Biochemical Systematics and Ecology vol37 no 1 pp 24ndash34 2009
[53] P Liu Y Hu D H Guo et al ldquoPotential antidepressantproperties of Radix Polygalae (Yuan Zhi)rdquo Phytomedicine vol17 no 10 pp 794ndash799 2010
[54] J F Wu S B Chen S L Chen and P F Tu ldquoThe chemical con-stituents of Polygala hongkongensisHemslrdquoActa PharmaceuticaSinica vol 42 no 7 pp 757ndash761 2007
[55] Y Song Y Jiang D Bi X Tian L Liang and P Tu ldquoChemicalconstituents from n-butanol extract of aerial part of Polygalasibiricardquo Zhongguo Zhongyao Zazhi vol 37 no 4 pp 471ndash4742012
[56] Y Ikeya S Takeda M Tunakawa et al ldquoCognitive improvingand cerebral protective effects of acylated oligosaccharides inPolygala tenuifoliardquo Biological and Pharmaceutical Bulletin vol27 no 7 pp 1081ndash1085 2004
[57] C J Zheng C L Hu X Q Ma C Peng H Zhang and L PQin ldquoCytotoxic phenylpropanoid glycosides from Fagopyrumtataricum (L) Gaertnrdquo Food Chemistry vol 132 no 1 pp 433ndash438 2012
[58] X Li Y F Zhang L Yang et al ldquoChemical profiling ofconstituents of Smilacis glabrae using ultra-high pressure liquidchromatography coupled with LTQ orbitrap mass spectrome-tryrdquo Natural Product Communications vol 7 no 2 pp 181ndash1842012
[59] T-T Sun D-W Zhang Y Han F-Y Dong andWWang ldquoSmi-lasides M and N two new phenylpropanoid glycosides fromSmilax ripariardquo Journal of Asian Natural Products Research vol14 no 2 pp 165ndash170 2012
[60] J Li X Bi G Zheng Y Hitoshi T Ikeda and T NoharaldquoSteroidal glycosides and aromatic compounds from Smilaxripariardquo Chemical amp Pharmaceutical Bulletin vol 54 no 10 pp1451ndash1454 2006
[61] N Wang X Yao R Ishii and S Kitanaka ldquoBioactive sucroseesters from Bidens parviflorardquo Phytochemistry vol 62 no 5 pp741ndash746 2003
[62] S Nakamura K Fujimoto T Matsumoto et al ldquoAcylatedsucroses and acylated quinic acids analogs from the flower budsof Prunus mume and their inhibitory effect on melanogenesisrdquoPhytochemistry vol 92 pp 128ndash136 2013
[63] K Fujimoto SNakamura TMatsumoto et al ldquoMedicinal flow-ers XXXVIII Structures of acylated sucroses and inhibitoryeffects of constituents on aldose reducatase from the flower budsofPrunusmumerdquoChemical and Pharmaceutical Bulletin vol 61no 4 pp 445ndash451 2013
[64] S Nakamura K Fujimoto T Matsumoto et al ldquoStructuresof acylated sucroses and an acylated flavonol glycoside andinhibitory effects of constituents on aldose reductase from theflower buds of Prunus mumerdquo Journal of Natural Medicines vol67 no 4 pp 799ndash806 2013
[65] L-B Dong J He X-Y Li et al ldquoChemical constituents fromthe aerial parts of Musella lasiocarpardquo Natural Products andBioprospecting vol 1 no 1 pp 41ndash47 2011
[66] Y Xiong K Z Deng Y Q Guo W Y Gao and T J ZhangldquoNew chemical constituents from the rhizomes of Sparganiumstoloniferumrdquo Archives of Pharmacal Research vol 32 no 5 pp717ndash720 2009
[67] Y Xiong K-Z Deng Y-Q Guo W-Y Gao and T-J ZhangldquoTwo new sucrose esters from Sparganium stoloniferumrdquo Jour-nal of Asian Natural Products Research vol 10 no 5 pp 425ndash428 2008
[68] B Chen N L Wang J H Huang and X S Yao ldquoIridoidand phenylpropanoid glycosides from Scrophularia ningpoensis
22 Evidence-Based Complementary and Alternative Medicine
Hemslrdquo Asian Journal of Traditional Medicines vol 2 no 3 pp119ndash123 2007
[69] H Chen Y Z Zhou L Qiao et al ldquoTwo new compounds fromCynanchum amplexicaulerdquo Journal of Asian Natural ProductsResearch vol 10 no 3 pp 248ndash251 2008
[70] C-L Chang L-J Zhang R Y Chen et al ldquoAntioxidant andanti-inflammatory phenylpropanoid derivatives from Calamusquiquesetinerviusrdquo Journal of Natural Products vol 73 no 9 pp1482ndash1488 2010
[71] Y Kawai H Kumagai H Kurihara K Yamazaki R Sawanoand N Inoue ldquo120573-Glucosidase inhibitory activities of phenyl-propanoid glycosides vanicoside A and B from Polygonumsachalinense rhizomerdquo Fitoterapia vol 77 no 6 pp 456ndash4592006
[72] P V Kiem N X Nhiem N X Cuong et al ldquoNew phenyl-propanoid esters of sucrose from Polygonum hydropiper andtheir antioxidant activityrdquo Archives of Pharmacal Research vol31 no 11 pp 1477ndash1482 2008
[73] K J Wang Y J Zhang and C R Yang ldquoAntioxidant phenolicconstituents from Fagopyrum dibotrysrdquo Journal of Ethnophar-macology vol 99 no 2 pp 259ndash264 2005
[74] N Cho J Huh H Yang et al ldquoChemical constituentsof Polygala tenuifolia roots and their inhibitory activity onlipopolysaccharide-induced nitric oxide production in BV2microgliardquo Journal of Enzyme Inhibition and Medicinal Chem-istry vol 27 no 1 pp 1ndash4 2012
[75] Q Ren C S Wu and J L Zhang ldquoUse of on-line stop-flowheart-cutting two-dimensional high performance liquid chro-matography for simultaneous determination of 12 major con-stituents in tartary buckwheat (Fagopyrum tataricum Gaertn)rdquoJournal of Chromatography A vol 1304 pp 257ndash262 2013
[76] Q Ren C S Wu Y Ren and J L Zhang ldquoCharacterizationand identification of the chemical constituents from tartarybuckwheat (Fagopyrum tataricumGaertn) by high performanceliquid chromatographyphotodiode array detectorlinear iontrap FTICR hybrid mass spectrometryrdquo Food Chemistry vol136 no 3-4 pp 1377ndash1389 2013
[77] W Li Y N Sun X T Yan et al ldquoNF-120581B inhibitory activityof sucrose fatty acid esters and related constituents fromAstragalus membranaceusrdquo Journal of Agricultural and FoodChemistry vol 61 no 29 pp 7081ndash7088 2013
[78] J T Cheng J He Y Li et al ldquoThree new sucrose fatty acid estersfrom Equisetum hiemale LrdquoHelvetica Chimica Acta vol 95 no7 pp 1158ndash1163 2012
[79] Y Jiang and P-F Tu ldquoTenuifoliose Q a new oligosaccharideester from the root of Polygala tenuifoliaWilldrdquo Journal of AsianNatural Products Research vol 5 no 4 pp 279ndash283 2003
[80] M Yoshikawa H Matsuda T Morikawa H H Xie S Naka-mura and O Muraoka ldquoPhenylethanoid oligoglycosides andacylated oligosugars with vasorelaxant activity from Cistanchetubulosardquo Bioorganic ampMedicinal Chemistry vol 14 no 22 pp7468ndash7475 2006
[81] P-F Tu H-M Shi Z-H Song Y Jiang and Y-Y ZhaoldquoChemical constituents of Cistanche sinensisrdquo Journal of AsianNatural Products Research vol 9 no 1 pp 79ndash84 2007
[82] C-L Si Y-Y Lu P-P Qin R-C Sun and Y-H Ni ldquoPhenolicextractives with chemotaxonomic significance from the bark ofPaulownia tomentosa var tomentosardquo BioResources vol 6 no4 pp 5086ndash5098 2011
[83] J Wu S Zhang Q Xiao et al ldquoPhenylethanoid and aliphaticalcohol glycosides from Acanthus ilicifoliusrdquo Phytochemistryvol 63 no 4 pp 491ndash495 2003
[84] Y Jiang and P-F Tu ldquoAnalysis of chemical constituents inCistanche speciesrdquo Journal of Chromatography A vol 1216 no11 pp 1970ndash1979 2009
[85] H Otsuka H Kuwabara and H Hoshiyama ldquoIdentification ofsucrose diesters of aryldihydronaphthalene-type lignans fromTrigonotis peduncularisand the nature of their fluorescencerdquoJournal of Natural Products vol 71 no 7 pp 1178ndash1181 2008
[86] M-R Suo J-S Yang and Q-H Liu ldquoLignan oligosaccharideesters from Eritrichium rupestrerdquo Journal of Natural Productsvol 69 no 4 pp 682ndash684 2006
[87] P-F Tu Z-H Song H-M Shi Y Jiang and Y-Y ZhaoldquoArylethyl (=phenylethanoid) glycosides and oligosaccharidefrom the stem of Cistanche tubulosardquo Helvetica Chimica Actavol 89 no 5 pp 927ndash935 2006
[88] M-H Shyr T-H Tsai and L-C Lin ldquoRossicasins A Band rosicaside F three new phenylpropanoid glycosides fromBoschniakia rossicardquoChemical and Pharmaceutical Bulletin vol54 no 2 pp 252ndash254 2006
[89] R FangNCVeitchGCKiteM J RHowes EA Porter andM S J Simmonds ldquoGlycosylated constituents of Iris fulvaandIris brevicaulisrdquoChemical amp Pharmaceutical Bulletin vol 59 no1 pp 124ndash128 2011
[90] J Fu L Zuo J Yang R Chen and D Zhang ldquoOligosaccharidepolyester and triterpenoid saponins from the roots of Polygalajaponicardquo Phytochemistry vol 69 no 7 pp 1617ndash1624 2008
[91] M-C Cheng C-Y Li H-C Ko F-N Ko Y-L Lin andT-S Wu ldquoAntidepressant principles of the roots of polygalatenuifoliardquo Journal of Natural Products vol 69 no 9 pp 1305ndash1309 2006
[92] H T Chang and P F Tu ldquoNew oligosaccharide esters andxanthone C-glucosides from Polygala telephioidesrdquo HelveticaChimica Acta vol 90 no 5 pp 944ndash950 2007
[93] J Li L Feng J Dai R Wang and T Nohara ldquoChemical con-stituents from Polygala telephioidesrdquo China Journal of ChineseMateria Medica vol 34 no 4 pp 402ndash405 2009
[94] W-P Yin T-Z Zhao and H-Y Zhang ldquoA novel oligosaccha-ride ester from Syringa pubescensrdquo Journal of Asian NaturalProducts Research vol 10 no 1 pp 95ndash100 2008
[95] M Valko D Leibfritz J Moncol M T D Cronin M Mazurand J Telser ldquoFree radicals and antioxidants in normal physio-logical functions and human diseaserdquoThe International Journalof Biochemistry amp Cell Biology vol 39 no 1 pp 44ndash84 2007
[96] D Krishnaiah R Sarbatly and R Nithyanandam ldquoA review ofthe antioxidant potential of medicinal plant speciesrdquo Food andBioproducts Processing vol 89 no 3 pp 217ndash233 2011
[97] P Liu Y Hu D-H Guo et al ldquoAntioxidant activity ofoligosaccharide ester extracted from Polygala tenuifolia roots insenescence-accelerated micerdquo Pharmaceutical Biology vol 48no 7 pp 828ndash833 2010
[98] Y Hu H-B Liao G Dai-Hong P Liu Y-Y Wang and KRahman ldquoAntidepressant-like effects of 361015840-disinapoyl sucroseon hippocampal neuronal plasticity and neurotrophic signalpathway in chronically mild stressed ratsrdquo NeurochemistryInternational vol 56 no 3 pp 461ndash465 2010
[99] Y Hu H B O Liao P Liu D-H Guo and K RahmanldquoA bioactive compound from Polygala tenuifolia regulatesefficiency of chronic stress on hypothalamic-pituitary-adrenalaxisrdquo Pharmazie vol 64 no 9 pp 605ndash608 2009
[100] A Jungbauer and SMedjakovic ldquoAnti-inflammatory propertiesof culinary herbs and spices that ameliorate the effects ofmetabolic syndromerdquoMaturitas vol 71 no 3 pp 227ndash239 2012
Evidence-Based Complementary and Alternative Medicine 23
[101] Q Xu Y Wang S Guo Z Shen and L Yang ldquoAnti-inflammatory and analgesic activity of aqueous extract of Flospopulirdquo Journal of Ethnopharmacology vol 152 no 3 pp 540ndash545 2014
[102] K S Kim D S Lee G S Bae et al ldquoThe inhibition of JNKMAPK and NF-120581B signaling by tenuifoliside A isolated fromPolygala tenuifolia in lipopolysaccharide-induced macrophagesis associated with its anti-inflammatory effectrdquo European Jour-nal of Pharmacology vol 721 no 1ndash3 pp 267ndash276 2013
[103] J-G Lee J-M Yon C Lin A Y Jung K Y Jung and S-YNamldquoCombined treatment with capsaicin and resveratrol enhancesneuroprotection against glutamate-induced toxicity in mousecerebral cortical neuronsrdquo Food and Chemical Toxicology vol50 no 11 pp 3877ndash3885 2012
[104] M L Jin S Y Park Y H Kim J-I Oh S J Lee andG Park ldquoThe neuroprotective effects of cordycepin inhibitglutamate-induced oxidative andER stress-associated apoptosisin hippocampal HT22 cellsrdquo NeuroToxicology vol 41 pp 102ndash111 2014
[105] P Liu Y Hu J Li et al ldquoProtection of SH-SY5Y neuronal cellsfrom glutamate-induced apoptosis by 36rsquo-disinapoyl sucrosea bioactive compound isolated from radix polygalardquo Journal ofBiomedicine and Biotechnology vol 2012 Article ID 728342 5pages 2012
[106] P-B Li W-L Lin Y-G Wang W Peng X-Y Cai and W-WSu ldquoAntidiabetic activities of oligosaccharides of Ophiopogonisjaponicus in experimental type 2 diabetic ratsrdquo InternationalJournal of Biological Macromolecules vol 51 no 5 pp 749ndash7552012
[107] T Liu Y M Yip L Song et al ldquoInhibiting enzymatic starchdigestion by the phenolic compound diboside A a mechanisticand in silico studyrdquo Food Research International vol 54 no 1pp 595ndash600 2013
[108] F Cote andMGHahn ldquoOligosaccharins structures and signaltransductionrdquo Plant Molecular Biology vol 26 no 5 pp 1379ndash1411 1994
[109] RACreelman and J EMullet ldquoOligosaccharins brassinolidesand jasmonates nontraditional regulators of plant growthdevelopment and gene expressionrdquo Plant Cell vol 9 no 7 pp1211ndash1223 1997
[110] L Jiao D Wan X Zhang B Li H Zhao and S LiuldquoCharacterization and immunostimulating effects on murineperitoneal macrophages of oligosaccharide isolated from Panaxginseng CAMeyerrdquo Journal of Ethnopharmacology vol 144 no3 pp 490ndash496 2012
Submit your manuscripts athttpwwwhindawicom
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Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
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Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
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EndocrinologyInternational Journal of
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Disease Markers
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
BioMed Research International
OncologyJournal of
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Oxidative Medicine and Cellular Longevity
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
PPAR Research
The Scientific World JournalHindawi Publishing Corporation httpwwwhindawicom Volume 2014
Immunology ResearchHindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Journal of
ObesityJournal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
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Computational and Mathematical Methods in Medicine
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Diabetes ResearchJournal of
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Research and TreatmentAIDS
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Gastroenterology Research and Practice
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Parkinsonrsquos Disease
Evidence-Based Complementary and Alternative Medicine
Volume 2014Hindawi Publishing Corporationhttpwwwhindawicom
Evidence-Based Complementary and Alternative Medicine 21
[38] H H Tu P Liu L Mu et al ldquoStudy on antidepressant com-ponents of sucrose ester from Polygala tenuifoliardquo ZhongguoZhongyao Zazhi vol 33 no 11 pp 1278ndash1280 2008
[39] G M She Y Y Ba Y Liu H Lv W Wang and R B ShildquoAbsorbable phenylpropenoyl sucroses from Polygala tenuifo-liardquoMolecules vol 16 no 7 pp 5507ndash5513 2011
[40] J Yong and P F Tu ldquoStudies on the chemical constituents inroot bark of Polygala tenuifolia (II)rdquo China Journal of ChineseMateria Medica vol 29 no 8 pp 751ndash753 2004
[41] M Ono C Takamura F Sugita et al ldquoTwo new steroidglycosides and a new sesquiterpenoid glycoside from theunderground parts of Trillium kamtschaticumrdquo Chemical andPharmaceutical Bulletin vol 55 no 4 pp 551ndash556 2007
[42] Y Ling Z Li M Chen Z Sun M Fan and C HuangldquoAnalysis and detection of the chemical constituents of RadixPolygalae and their metabolites in rats after oral administrationby ultra high-performance liquid chromatography coupledwith electrospray ionization quadrupole time-of-flight tandemmass spectrometryrdquo Journal of Pharmaceutical and BiomedicalAnalysis vol 85 pp 1ndash13 2013
[43] P Fan L Terrier A-E Hay A Marston and K HostettmannldquoAntioxidant and enzyme inhibition activities and chemicalprofiles ofPolygonum sachalinensis FSchmidt exMaxim (Polyg-onaceae)rdquo Fitoterapia vol 81 no 2 pp 124ndash131 2010
[44] L J Zhang C C Liao H C Huang Y C Shen L M Yangand Y H Kuo ldquoAntioxidant phenylpropanoid glycosides fromSmilax bracteatardquo Phytochemistry vol 69 no 6 pp 1398ndash14042008
[45] L L Yan W Y Gao Y J Zhang and Y Wang ldquoA new phenyl-propanoid glycosides from Paris polyphylla var yunnanensisrdquoFitoterapia vol 79 no 4 pp 306ndash307 2008
[46] Y H Kuo Y W Hsu C C Liaw J K Lee H C Huang andL M Y Kuo ldquoCytotoxic phenylpropanoid glycosides from thestems of Smilax chinardquo Journal of Natural Products vol 68 no10 pp 1475ndash1478 2005
[47] W-X Wang T-X Li H Ma J-F Zhang and A-Q JialdquoTumoral cytotoxic and antioxidative phenylpropanoid glyco-sides in Smilax riparia A DCrdquo Journal of Ethnopharmacologyvol 149 no 2 pp 527ndash532 2013
[48] N X Nhiem P vanKiem C vanMinh et al ldquoPhenylpropanoidglycosides fromHeterosmilax erythrantha and their antioxidantactivityrdquo Archives of Pharmacal Research vol 32 no 10 pp1373ndash1377 2009
[49] Y Wang W Y Gao T J Zhang and Y Q Guo ldquoA novelphenylpropanoid glycosides and a new derivation of phenolicglycoside from Paris Polyphylla var yunnanensisrdquo ChineseChemical Letters vol 18 no 5 pp 548ndash550 2007
[50] J-Y Zhang Y-Z Wang Y-L Zhao et al ldquoPhytochemicals andbioactivities of Paris speciesrdquo Journal of Asian Natural ProductsResearch vol 13 no 7 pp 670ndash681 2011
[51] N H N Hashim F Abas K Shaari and N H Lajis ldquoLC-DAD-ESIMSMS characterization of antioxidant and anti-cholinesterase constituents present in the active fraction fromPersicaria hydropiperrdquo LWT Food Science and Technology vol46 no 2 pp 468ndash476 2012
[52] PH FanA EHayAMarstonHX Lou andKHostettmannldquoChemical variability of the invasive neophytes Polygonumcuspidatum Sieb and Zucc and Polygonum sachalinensis FSchmidt ex Maximrdquo Biochemical Systematics and Ecology vol37 no 1 pp 24ndash34 2009
[53] P Liu Y Hu D H Guo et al ldquoPotential antidepressantproperties of Radix Polygalae (Yuan Zhi)rdquo Phytomedicine vol17 no 10 pp 794ndash799 2010
[54] J F Wu S B Chen S L Chen and P F Tu ldquoThe chemical con-stituents of Polygala hongkongensisHemslrdquoActa PharmaceuticaSinica vol 42 no 7 pp 757ndash761 2007
[55] Y Song Y Jiang D Bi X Tian L Liang and P Tu ldquoChemicalconstituents from n-butanol extract of aerial part of Polygalasibiricardquo Zhongguo Zhongyao Zazhi vol 37 no 4 pp 471ndash4742012
[56] Y Ikeya S Takeda M Tunakawa et al ldquoCognitive improvingand cerebral protective effects of acylated oligosaccharides inPolygala tenuifoliardquo Biological and Pharmaceutical Bulletin vol27 no 7 pp 1081ndash1085 2004
[57] C J Zheng C L Hu X Q Ma C Peng H Zhang and L PQin ldquoCytotoxic phenylpropanoid glycosides from Fagopyrumtataricum (L) Gaertnrdquo Food Chemistry vol 132 no 1 pp 433ndash438 2012
[58] X Li Y F Zhang L Yang et al ldquoChemical profiling ofconstituents of Smilacis glabrae using ultra-high pressure liquidchromatography coupled with LTQ orbitrap mass spectrome-tryrdquo Natural Product Communications vol 7 no 2 pp 181ndash1842012
[59] T-T Sun D-W Zhang Y Han F-Y Dong andWWang ldquoSmi-lasides M and N two new phenylpropanoid glycosides fromSmilax ripariardquo Journal of Asian Natural Products Research vol14 no 2 pp 165ndash170 2012
[60] J Li X Bi G Zheng Y Hitoshi T Ikeda and T NoharaldquoSteroidal glycosides and aromatic compounds from Smilaxripariardquo Chemical amp Pharmaceutical Bulletin vol 54 no 10 pp1451ndash1454 2006
[61] N Wang X Yao R Ishii and S Kitanaka ldquoBioactive sucroseesters from Bidens parviflorardquo Phytochemistry vol 62 no 5 pp741ndash746 2003
[62] S Nakamura K Fujimoto T Matsumoto et al ldquoAcylatedsucroses and acylated quinic acids analogs from the flower budsof Prunus mume and their inhibitory effect on melanogenesisrdquoPhytochemistry vol 92 pp 128ndash136 2013
[63] K Fujimoto SNakamura TMatsumoto et al ldquoMedicinal flow-ers XXXVIII Structures of acylated sucroses and inhibitoryeffects of constituents on aldose reducatase from the flower budsofPrunusmumerdquoChemical and Pharmaceutical Bulletin vol 61no 4 pp 445ndash451 2013
[64] S Nakamura K Fujimoto T Matsumoto et al ldquoStructuresof acylated sucroses and an acylated flavonol glycoside andinhibitory effects of constituents on aldose reductase from theflower buds of Prunus mumerdquo Journal of Natural Medicines vol67 no 4 pp 799ndash806 2013
[65] L-B Dong J He X-Y Li et al ldquoChemical constituents fromthe aerial parts of Musella lasiocarpardquo Natural Products andBioprospecting vol 1 no 1 pp 41ndash47 2011
[66] Y Xiong K Z Deng Y Q Guo W Y Gao and T J ZhangldquoNew chemical constituents from the rhizomes of Sparganiumstoloniferumrdquo Archives of Pharmacal Research vol 32 no 5 pp717ndash720 2009
[67] Y Xiong K-Z Deng Y-Q Guo W-Y Gao and T-J ZhangldquoTwo new sucrose esters from Sparganium stoloniferumrdquo Jour-nal of Asian Natural Products Research vol 10 no 5 pp 425ndash428 2008
[68] B Chen N L Wang J H Huang and X S Yao ldquoIridoidand phenylpropanoid glycosides from Scrophularia ningpoensis
22 Evidence-Based Complementary and Alternative Medicine
Hemslrdquo Asian Journal of Traditional Medicines vol 2 no 3 pp119ndash123 2007
[69] H Chen Y Z Zhou L Qiao et al ldquoTwo new compounds fromCynanchum amplexicaulerdquo Journal of Asian Natural ProductsResearch vol 10 no 3 pp 248ndash251 2008
[70] C-L Chang L-J Zhang R Y Chen et al ldquoAntioxidant andanti-inflammatory phenylpropanoid derivatives from Calamusquiquesetinerviusrdquo Journal of Natural Products vol 73 no 9 pp1482ndash1488 2010
[71] Y Kawai H Kumagai H Kurihara K Yamazaki R Sawanoand N Inoue ldquo120573-Glucosidase inhibitory activities of phenyl-propanoid glycosides vanicoside A and B from Polygonumsachalinense rhizomerdquo Fitoterapia vol 77 no 6 pp 456ndash4592006
[72] P V Kiem N X Nhiem N X Cuong et al ldquoNew phenyl-propanoid esters of sucrose from Polygonum hydropiper andtheir antioxidant activityrdquo Archives of Pharmacal Research vol31 no 11 pp 1477ndash1482 2008
[73] K J Wang Y J Zhang and C R Yang ldquoAntioxidant phenolicconstituents from Fagopyrum dibotrysrdquo Journal of Ethnophar-macology vol 99 no 2 pp 259ndash264 2005
[74] N Cho J Huh H Yang et al ldquoChemical constituentsof Polygala tenuifolia roots and their inhibitory activity onlipopolysaccharide-induced nitric oxide production in BV2microgliardquo Journal of Enzyme Inhibition and Medicinal Chem-istry vol 27 no 1 pp 1ndash4 2012
[75] Q Ren C S Wu and J L Zhang ldquoUse of on-line stop-flowheart-cutting two-dimensional high performance liquid chro-matography for simultaneous determination of 12 major con-stituents in tartary buckwheat (Fagopyrum tataricum Gaertn)rdquoJournal of Chromatography A vol 1304 pp 257ndash262 2013
[76] Q Ren C S Wu Y Ren and J L Zhang ldquoCharacterizationand identification of the chemical constituents from tartarybuckwheat (Fagopyrum tataricumGaertn) by high performanceliquid chromatographyphotodiode array detectorlinear iontrap FTICR hybrid mass spectrometryrdquo Food Chemistry vol136 no 3-4 pp 1377ndash1389 2013
[77] W Li Y N Sun X T Yan et al ldquoNF-120581B inhibitory activityof sucrose fatty acid esters and related constituents fromAstragalus membranaceusrdquo Journal of Agricultural and FoodChemistry vol 61 no 29 pp 7081ndash7088 2013
[78] J T Cheng J He Y Li et al ldquoThree new sucrose fatty acid estersfrom Equisetum hiemale LrdquoHelvetica Chimica Acta vol 95 no7 pp 1158ndash1163 2012
[79] Y Jiang and P-F Tu ldquoTenuifoliose Q a new oligosaccharideester from the root of Polygala tenuifoliaWilldrdquo Journal of AsianNatural Products Research vol 5 no 4 pp 279ndash283 2003
[80] M Yoshikawa H Matsuda T Morikawa H H Xie S Naka-mura and O Muraoka ldquoPhenylethanoid oligoglycosides andacylated oligosugars with vasorelaxant activity from Cistanchetubulosardquo Bioorganic ampMedicinal Chemistry vol 14 no 22 pp7468ndash7475 2006
[81] P-F Tu H-M Shi Z-H Song Y Jiang and Y-Y ZhaoldquoChemical constituents of Cistanche sinensisrdquo Journal of AsianNatural Products Research vol 9 no 1 pp 79ndash84 2007
[82] C-L Si Y-Y Lu P-P Qin R-C Sun and Y-H Ni ldquoPhenolicextractives with chemotaxonomic significance from the bark ofPaulownia tomentosa var tomentosardquo BioResources vol 6 no4 pp 5086ndash5098 2011
[83] J Wu S Zhang Q Xiao et al ldquoPhenylethanoid and aliphaticalcohol glycosides from Acanthus ilicifoliusrdquo Phytochemistryvol 63 no 4 pp 491ndash495 2003
[84] Y Jiang and P-F Tu ldquoAnalysis of chemical constituents inCistanche speciesrdquo Journal of Chromatography A vol 1216 no11 pp 1970ndash1979 2009
[85] H Otsuka H Kuwabara and H Hoshiyama ldquoIdentification ofsucrose diesters of aryldihydronaphthalene-type lignans fromTrigonotis peduncularisand the nature of their fluorescencerdquoJournal of Natural Products vol 71 no 7 pp 1178ndash1181 2008
[86] M-R Suo J-S Yang and Q-H Liu ldquoLignan oligosaccharideesters from Eritrichium rupestrerdquo Journal of Natural Productsvol 69 no 4 pp 682ndash684 2006
[87] P-F Tu Z-H Song H-M Shi Y Jiang and Y-Y ZhaoldquoArylethyl (=phenylethanoid) glycosides and oligosaccharidefrom the stem of Cistanche tubulosardquo Helvetica Chimica Actavol 89 no 5 pp 927ndash935 2006
[88] M-H Shyr T-H Tsai and L-C Lin ldquoRossicasins A Band rosicaside F three new phenylpropanoid glycosides fromBoschniakia rossicardquoChemical and Pharmaceutical Bulletin vol54 no 2 pp 252ndash254 2006
[89] R FangNCVeitchGCKiteM J RHowes EA Porter andM S J Simmonds ldquoGlycosylated constituents of Iris fulvaandIris brevicaulisrdquoChemical amp Pharmaceutical Bulletin vol 59 no1 pp 124ndash128 2011
[90] J Fu L Zuo J Yang R Chen and D Zhang ldquoOligosaccharidepolyester and triterpenoid saponins from the roots of Polygalajaponicardquo Phytochemistry vol 69 no 7 pp 1617ndash1624 2008
[91] M-C Cheng C-Y Li H-C Ko F-N Ko Y-L Lin andT-S Wu ldquoAntidepressant principles of the roots of polygalatenuifoliardquo Journal of Natural Products vol 69 no 9 pp 1305ndash1309 2006
[92] H T Chang and P F Tu ldquoNew oligosaccharide esters andxanthone C-glucosides from Polygala telephioidesrdquo HelveticaChimica Acta vol 90 no 5 pp 944ndash950 2007
[93] J Li L Feng J Dai R Wang and T Nohara ldquoChemical con-stituents from Polygala telephioidesrdquo China Journal of ChineseMateria Medica vol 34 no 4 pp 402ndash405 2009
[94] W-P Yin T-Z Zhao and H-Y Zhang ldquoA novel oligosaccha-ride ester from Syringa pubescensrdquo Journal of Asian NaturalProducts Research vol 10 no 1 pp 95ndash100 2008
[95] M Valko D Leibfritz J Moncol M T D Cronin M Mazurand J Telser ldquoFree radicals and antioxidants in normal physio-logical functions and human diseaserdquoThe International Journalof Biochemistry amp Cell Biology vol 39 no 1 pp 44ndash84 2007
[96] D Krishnaiah R Sarbatly and R Nithyanandam ldquoA review ofthe antioxidant potential of medicinal plant speciesrdquo Food andBioproducts Processing vol 89 no 3 pp 217ndash233 2011
[97] P Liu Y Hu D-H Guo et al ldquoAntioxidant activity ofoligosaccharide ester extracted from Polygala tenuifolia roots insenescence-accelerated micerdquo Pharmaceutical Biology vol 48no 7 pp 828ndash833 2010
[98] Y Hu H-B Liao G Dai-Hong P Liu Y-Y Wang and KRahman ldquoAntidepressant-like effects of 361015840-disinapoyl sucroseon hippocampal neuronal plasticity and neurotrophic signalpathway in chronically mild stressed ratsrdquo NeurochemistryInternational vol 56 no 3 pp 461ndash465 2010
[99] Y Hu H B O Liao P Liu D-H Guo and K RahmanldquoA bioactive compound from Polygala tenuifolia regulatesefficiency of chronic stress on hypothalamic-pituitary-adrenalaxisrdquo Pharmazie vol 64 no 9 pp 605ndash608 2009
[100] A Jungbauer and SMedjakovic ldquoAnti-inflammatory propertiesof culinary herbs and spices that ameliorate the effects ofmetabolic syndromerdquoMaturitas vol 71 no 3 pp 227ndash239 2012
Evidence-Based Complementary and Alternative Medicine 23
[101] Q Xu Y Wang S Guo Z Shen and L Yang ldquoAnti-inflammatory and analgesic activity of aqueous extract of Flospopulirdquo Journal of Ethnopharmacology vol 152 no 3 pp 540ndash545 2014
[102] K S Kim D S Lee G S Bae et al ldquoThe inhibition of JNKMAPK and NF-120581B signaling by tenuifoliside A isolated fromPolygala tenuifolia in lipopolysaccharide-induced macrophagesis associated with its anti-inflammatory effectrdquo European Jour-nal of Pharmacology vol 721 no 1ndash3 pp 267ndash276 2013
[103] J-G Lee J-M Yon C Lin A Y Jung K Y Jung and S-YNamldquoCombined treatment with capsaicin and resveratrol enhancesneuroprotection against glutamate-induced toxicity in mousecerebral cortical neuronsrdquo Food and Chemical Toxicology vol50 no 11 pp 3877ndash3885 2012
[104] M L Jin S Y Park Y H Kim J-I Oh S J Lee andG Park ldquoThe neuroprotective effects of cordycepin inhibitglutamate-induced oxidative andER stress-associated apoptosisin hippocampal HT22 cellsrdquo NeuroToxicology vol 41 pp 102ndash111 2014
[105] P Liu Y Hu J Li et al ldquoProtection of SH-SY5Y neuronal cellsfrom glutamate-induced apoptosis by 36rsquo-disinapoyl sucrosea bioactive compound isolated from radix polygalardquo Journal ofBiomedicine and Biotechnology vol 2012 Article ID 728342 5pages 2012
[106] P-B Li W-L Lin Y-G Wang W Peng X-Y Cai and W-WSu ldquoAntidiabetic activities of oligosaccharides of Ophiopogonisjaponicus in experimental type 2 diabetic ratsrdquo InternationalJournal of Biological Macromolecules vol 51 no 5 pp 749ndash7552012
[107] T Liu Y M Yip L Song et al ldquoInhibiting enzymatic starchdigestion by the phenolic compound diboside A a mechanisticand in silico studyrdquo Food Research International vol 54 no 1pp 595ndash600 2013
[108] F Cote andMGHahn ldquoOligosaccharins structures and signaltransductionrdquo Plant Molecular Biology vol 26 no 5 pp 1379ndash1411 1994
[109] RACreelman and J EMullet ldquoOligosaccharins brassinolidesand jasmonates nontraditional regulators of plant growthdevelopment and gene expressionrdquo Plant Cell vol 9 no 7 pp1211ndash1223 1997
[110] L Jiao D Wan X Zhang B Li H Zhao and S LiuldquoCharacterization and immunostimulating effects on murineperitoneal macrophages of oligosaccharide isolated from Panaxginseng CAMeyerrdquo Journal of Ethnopharmacology vol 144 no3 pp 490ndash496 2012
Submit your manuscripts athttpwwwhindawicom
Stem CellsInternational
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
MEDIATORSINFLAMMATION
of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Behavioural Neurology
EndocrinologyInternational Journal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Disease Markers
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
BioMed Research International
OncologyJournal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Oxidative Medicine and Cellular Longevity
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
PPAR Research
The Scientific World JournalHindawi Publishing Corporation httpwwwhindawicom Volume 2014
Immunology ResearchHindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Journal of
ObesityJournal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Computational and Mathematical Methods in Medicine
OphthalmologyJournal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Diabetes ResearchJournal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Research and TreatmentAIDS
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Gastroenterology Research and Practice
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Parkinsonrsquos Disease
Evidence-Based Complementary and Alternative Medicine
Volume 2014Hindawi Publishing Corporationhttpwwwhindawicom
22 Evidence-Based Complementary and Alternative Medicine
Hemslrdquo Asian Journal of Traditional Medicines vol 2 no 3 pp119ndash123 2007
[69] H Chen Y Z Zhou L Qiao et al ldquoTwo new compounds fromCynanchum amplexicaulerdquo Journal of Asian Natural ProductsResearch vol 10 no 3 pp 248ndash251 2008
[70] C-L Chang L-J Zhang R Y Chen et al ldquoAntioxidant andanti-inflammatory phenylpropanoid derivatives from Calamusquiquesetinerviusrdquo Journal of Natural Products vol 73 no 9 pp1482ndash1488 2010
[71] Y Kawai H Kumagai H Kurihara K Yamazaki R Sawanoand N Inoue ldquo120573-Glucosidase inhibitory activities of phenyl-propanoid glycosides vanicoside A and B from Polygonumsachalinense rhizomerdquo Fitoterapia vol 77 no 6 pp 456ndash4592006
[72] P V Kiem N X Nhiem N X Cuong et al ldquoNew phenyl-propanoid esters of sucrose from Polygonum hydropiper andtheir antioxidant activityrdquo Archives of Pharmacal Research vol31 no 11 pp 1477ndash1482 2008
[73] K J Wang Y J Zhang and C R Yang ldquoAntioxidant phenolicconstituents from Fagopyrum dibotrysrdquo Journal of Ethnophar-macology vol 99 no 2 pp 259ndash264 2005
[74] N Cho J Huh H Yang et al ldquoChemical constituentsof Polygala tenuifolia roots and their inhibitory activity onlipopolysaccharide-induced nitric oxide production in BV2microgliardquo Journal of Enzyme Inhibition and Medicinal Chem-istry vol 27 no 1 pp 1ndash4 2012
[75] Q Ren C S Wu and J L Zhang ldquoUse of on-line stop-flowheart-cutting two-dimensional high performance liquid chro-matography for simultaneous determination of 12 major con-stituents in tartary buckwheat (Fagopyrum tataricum Gaertn)rdquoJournal of Chromatography A vol 1304 pp 257ndash262 2013
[76] Q Ren C S Wu Y Ren and J L Zhang ldquoCharacterizationand identification of the chemical constituents from tartarybuckwheat (Fagopyrum tataricumGaertn) by high performanceliquid chromatographyphotodiode array detectorlinear iontrap FTICR hybrid mass spectrometryrdquo Food Chemistry vol136 no 3-4 pp 1377ndash1389 2013
[77] W Li Y N Sun X T Yan et al ldquoNF-120581B inhibitory activityof sucrose fatty acid esters and related constituents fromAstragalus membranaceusrdquo Journal of Agricultural and FoodChemistry vol 61 no 29 pp 7081ndash7088 2013
[78] J T Cheng J He Y Li et al ldquoThree new sucrose fatty acid estersfrom Equisetum hiemale LrdquoHelvetica Chimica Acta vol 95 no7 pp 1158ndash1163 2012
[79] Y Jiang and P-F Tu ldquoTenuifoliose Q a new oligosaccharideester from the root of Polygala tenuifoliaWilldrdquo Journal of AsianNatural Products Research vol 5 no 4 pp 279ndash283 2003
[80] M Yoshikawa H Matsuda T Morikawa H H Xie S Naka-mura and O Muraoka ldquoPhenylethanoid oligoglycosides andacylated oligosugars with vasorelaxant activity from Cistanchetubulosardquo Bioorganic ampMedicinal Chemistry vol 14 no 22 pp7468ndash7475 2006
[81] P-F Tu H-M Shi Z-H Song Y Jiang and Y-Y ZhaoldquoChemical constituents of Cistanche sinensisrdquo Journal of AsianNatural Products Research vol 9 no 1 pp 79ndash84 2007
[82] C-L Si Y-Y Lu P-P Qin R-C Sun and Y-H Ni ldquoPhenolicextractives with chemotaxonomic significance from the bark ofPaulownia tomentosa var tomentosardquo BioResources vol 6 no4 pp 5086ndash5098 2011
[83] J Wu S Zhang Q Xiao et al ldquoPhenylethanoid and aliphaticalcohol glycosides from Acanthus ilicifoliusrdquo Phytochemistryvol 63 no 4 pp 491ndash495 2003
[84] Y Jiang and P-F Tu ldquoAnalysis of chemical constituents inCistanche speciesrdquo Journal of Chromatography A vol 1216 no11 pp 1970ndash1979 2009
[85] H Otsuka H Kuwabara and H Hoshiyama ldquoIdentification ofsucrose diesters of aryldihydronaphthalene-type lignans fromTrigonotis peduncularisand the nature of their fluorescencerdquoJournal of Natural Products vol 71 no 7 pp 1178ndash1181 2008
[86] M-R Suo J-S Yang and Q-H Liu ldquoLignan oligosaccharideesters from Eritrichium rupestrerdquo Journal of Natural Productsvol 69 no 4 pp 682ndash684 2006
[87] P-F Tu Z-H Song H-M Shi Y Jiang and Y-Y ZhaoldquoArylethyl (=phenylethanoid) glycosides and oligosaccharidefrom the stem of Cistanche tubulosardquo Helvetica Chimica Actavol 89 no 5 pp 927ndash935 2006
[88] M-H Shyr T-H Tsai and L-C Lin ldquoRossicasins A Band rosicaside F three new phenylpropanoid glycosides fromBoschniakia rossicardquoChemical and Pharmaceutical Bulletin vol54 no 2 pp 252ndash254 2006
[89] R FangNCVeitchGCKiteM J RHowes EA Porter andM S J Simmonds ldquoGlycosylated constituents of Iris fulvaandIris brevicaulisrdquoChemical amp Pharmaceutical Bulletin vol 59 no1 pp 124ndash128 2011
[90] J Fu L Zuo J Yang R Chen and D Zhang ldquoOligosaccharidepolyester and triterpenoid saponins from the roots of Polygalajaponicardquo Phytochemistry vol 69 no 7 pp 1617ndash1624 2008
[91] M-C Cheng C-Y Li H-C Ko F-N Ko Y-L Lin andT-S Wu ldquoAntidepressant principles of the roots of polygalatenuifoliardquo Journal of Natural Products vol 69 no 9 pp 1305ndash1309 2006
[92] H T Chang and P F Tu ldquoNew oligosaccharide esters andxanthone C-glucosides from Polygala telephioidesrdquo HelveticaChimica Acta vol 90 no 5 pp 944ndash950 2007
[93] J Li L Feng J Dai R Wang and T Nohara ldquoChemical con-stituents from Polygala telephioidesrdquo China Journal of ChineseMateria Medica vol 34 no 4 pp 402ndash405 2009
[94] W-P Yin T-Z Zhao and H-Y Zhang ldquoA novel oligosaccha-ride ester from Syringa pubescensrdquo Journal of Asian NaturalProducts Research vol 10 no 1 pp 95ndash100 2008
[95] M Valko D Leibfritz J Moncol M T D Cronin M Mazurand J Telser ldquoFree radicals and antioxidants in normal physio-logical functions and human diseaserdquoThe International Journalof Biochemistry amp Cell Biology vol 39 no 1 pp 44ndash84 2007
[96] D Krishnaiah R Sarbatly and R Nithyanandam ldquoA review ofthe antioxidant potential of medicinal plant speciesrdquo Food andBioproducts Processing vol 89 no 3 pp 217ndash233 2011
[97] P Liu Y Hu D-H Guo et al ldquoAntioxidant activity ofoligosaccharide ester extracted from Polygala tenuifolia roots insenescence-accelerated micerdquo Pharmaceutical Biology vol 48no 7 pp 828ndash833 2010
[98] Y Hu H-B Liao G Dai-Hong P Liu Y-Y Wang and KRahman ldquoAntidepressant-like effects of 361015840-disinapoyl sucroseon hippocampal neuronal plasticity and neurotrophic signalpathway in chronically mild stressed ratsrdquo NeurochemistryInternational vol 56 no 3 pp 461ndash465 2010
[99] Y Hu H B O Liao P Liu D-H Guo and K RahmanldquoA bioactive compound from Polygala tenuifolia regulatesefficiency of chronic stress on hypothalamic-pituitary-adrenalaxisrdquo Pharmazie vol 64 no 9 pp 605ndash608 2009
[100] A Jungbauer and SMedjakovic ldquoAnti-inflammatory propertiesof culinary herbs and spices that ameliorate the effects ofmetabolic syndromerdquoMaturitas vol 71 no 3 pp 227ndash239 2012
Evidence-Based Complementary and Alternative Medicine 23
[101] Q Xu Y Wang S Guo Z Shen and L Yang ldquoAnti-inflammatory and analgesic activity of aqueous extract of Flospopulirdquo Journal of Ethnopharmacology vol 152 no 3 pp 540ndash545 2014
[102] K S Kim D S Lee G S Bae et al ldquoThe inhibition of JNKMAPK and NF-120581B signaling by tenuifoliside A isolated fromPolygala tenuifolia in lipopolysaccharide-induced macrophagesis associated with its anti-inflammatory effectrdquo European Jour-nal of Pharmacology vol 721 no 1ndash3 pp 267ndash276 2013
[103] J-G Lee J-M Yon C Lin A Y Jung K Y Jung and S-YNamldquoCombined treatment with capsaicin and resveratrol enhancesneuroprotection against glutamate-induced toxicity in mousecerebral cortical neuronsrdquo Food and Chemical Toxicology vol50 no 11 pp 3877ndash3885 2012
[104] M L Jin S Y Park Y H Kim J-I Oh S J Lee andG Park ldquoThe neuroprotective effects of cordycepin inhibitglutamate-induced oxidative andER stress-associated apoptosisin hippocampal HT22 cellsrdquo NeuroToxicology vol 41 pp 102ndash111 2014
[105] P Liu Y Hu J Li et al ldquoProtection of SH-SY5Y neuronal cellsfrom glutamate-induced apoptosis by 36rsquo-disinapoyl sucrosea bioactive compound isolated from radix polygalardquo Journal ofBiomedicine and Biotechnology vol 2012 Article ID 728342 5pages 2012
[106] P-B Li W-L Lin Y-G Wang W Peng X-Y Cai and W-WSu ldquoAntidiabetic activities of oligosaccharides of Ophiopogonisjaponicus in experimental type 2 diabetic ratsrdquo InternationalJournal of Biological Macromolecules vol 51 no 5 pp 749ndash7552012
[107] T Liu Y M Yip L Song et al ldquoInhibiting enzymatic starchdigestion by the phenolic compound diboside A a mechanisticand in silico studyrdquo Food Research International vol 54 no 1pp 595ndash600 2013
[108] F Cote andMGHahn ldquoOligosaccharins structures and signaltransductionrdquo Plant Molecular Biology vol 26 no 5 pp 1379ndash1411 1994
[109] RACreelman and J EMullet ldquoOligosaccharins brassinolidesand jasmonates nontraditional regulators of plant growthdevelopment and gene expressionrdquo Plant Cell vol 9 no 7 pp1211ndash1223 1997
[110] L Jiao D Wan X Zhang B Li H Zhao and S LiuldquoCharacterization and immunostimulating effects on murineperitoneal macrophages of oligosaccharide isolated from Panaxginseng CAMeyerrdquo Journal of Ethnopharmacology vol 144 no3 pp 490ndash496 2012
Submit your manuscripts athttpwwwhindawicom
Stem CellsInternational
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
MEDIATORSINFLAMMATION
of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Behavioural Neurology
EndocrinologyInternational Journal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Disease Markers
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
BioMed Research International
OncologyJournal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Oxidative Medicine and Cellular Longevity
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
PPAR Research
The Scientific World JournalHindawi Publishing Corporation httpwwwhindawicom Volume 2014
Immunology ResearchHindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Journal of
ObesityJournal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Computational and Mathematical Methods in Medicine
OphthalmologyJournal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Diabetes ResearchJournal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Research and TreatmentAIDS
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Gastroenterology Research and Practice
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Parkinsonrsquos Disease
Evidence-Based Complementary and Alternative Medicine
Volume 2014Hindawi Publishing Corporationhttpwwwhindawicom
Evidence-Based Complementary and Alternative Medicine 23
[101] Q Xu Y Wang S Guo Z Shen and L Yang ldquoAnti-inflammatory and analgesic activity of aqueous extract of Flospopulirdquo Journal of Ethnopharmacology vol 152 no 3 pp 540ndash545 2014
[102] K S Kim D S Lee G S Bae et al ldquoThe inhibition of JNKMAPK and NF-120581B signaling by tenuifoliside A isolated fromPolygala tenuifolia in lipopolysaccharide-induced macrophagesis associated with its anti-inflammatory effectrdquo European Jour-nal of Pharmacology vol 721 no 1ndash3 pp 267ndash276 2013
[103] J-G Lee J-M Yon C Lin A Y Jung K Y Jung and S-YNamldquoCombined treatment with capsaicin and resveratrol enhancesneuroprotection against glutamate-induced toxicity in mousecerebral cortical neuronsrdquo Food and Chemical Toxicology vol50 no 11 pp 3877ndash3885 2012
[104] M L Jin S Y Park Y H Kim J-I Oh S J Lee andG Park ldquoThe neuroprotective effects of cordycepin inhibitglutamate-induced oxidative andER stress-associated apoptosisin hippocampal HT22 cellsrdquo NeuroToxicology vol 41 pp 102ndash111 2014
[105] P Liu Y Hu J Li et al ldquoProtection of SH-SY5Y neuronal cellsfrom glutamate-induced apoptosis by 36rsquo-disinapoyl sucrosea bioactive compound isolated from radix polygalardquo Journal ofBiomedicine and Biotechnology vol 2012 Article ID 728342 5pages 2012
[106] P-B Li W-L Lin Y-G Wang W Peng X-Y Cai and W-WSu ldquoAntidiabetic activities of oligosaccharides of Ophiopogonisjaponicus in experimental type 2 diabetic ratsrdquo InternationalJournal of Biological Macromolecules vol 51 no 5 pp 749ndash7552012
[107] T Liu Y M Yip L Song et al ldquoInhibiting enzymatic starchdigestion by the phenolic compound diboside A a mechanisticand in silico studyrdquo Food Research International vol 54 no 1pp 595ndash600 2013
[108] F Cote andMGHahn ldquoOligosaccharins structures and signaltransductionrdquo Plant Molecular Biology vol 26 no 5 pp 1379ndash1411 1994
[109] RACreelman and J EMullet ldquoOligosaccharins brassinolidesand jasmonates nontraditional regulators of plant growthdevelopment and gene expressionrdquo Plant Cell vol 9 no 7 pp1211ndash1223 1997
[110] L Jiao D Wan X Zhang B Li H Zhao and S LiuldquoCharacterization and immunostimulating effects on murineperitoneal macrophages of oligosaccharide isolated from Panaxginseng CAMeyerrdquo Journal of Ethnopharmacology vol 144 no3 pp 490ndash496 2012
Submit your manuscripts athttpwwwhindawicom
Stem CellsInternational
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
MEDIATORSINFLAMMATION
of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Behavioural Neurology
EndocrinologyInternational Journal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Disease Markers
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
BioMed Research International
OncologyJournal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Oxidative Medicine and Cellular Longevity
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
PPAR Research
The Scientific World JournalHindawi Publishing Corporation httpwwwhindawicom Volume 2014
Immunology ResearchHindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Journal of
ObesityJournal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Computational and Mathematical Methods in Medicine
OphthalmologyJournal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Diabetes ResearchJournal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Research and TreatmentAIDS
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Gastroenterology Research and Practice
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Parkinsonrsquos Disease
Evidence-Based Complementary and Alternative Medicine
Volume 2014Hindawi Publishing Corporationhttpwwwhindawicom
Submit your manuscripts athttpwwwhindawicom
Stem CellsInternational
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
MEDIATORSINFLAMMATION
of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Behavioural Neurology
EndocrinologyInternational Journal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Disease Markers
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
BioMed Research International
OncologyJournal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Oxidative Medicine and Cellular Longevity
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
PPAR Research
The Scientific World JournalHindawi Publishing Corporation httpwwwhindawicom Volume 2014
Immunology ResearchHindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Journal of
ObesityJournal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Computational and Mathematical Methods in Medicine
OphthalmologyJournal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Diabetes ResearchJournal of
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Research and TreatmentAIDS
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Gastroenterology Research and Practice
Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014
Parkinsonrsquos Disease
Evidence-Based Complementary and Alternative Medicine
Volume 2014Hindawi Publishing Corporationhttpwwwhindawicom