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SOME REPRESENTATIVE
COMPOUNDS ISOLATED
FROM MARINE ORGANISMS
AEROPLYSININ-1
from the sponge Aplysina aerophoba
Chem. Comm. 751 (1970)
1970
OCH3
Br
HO
Br
HO
CN
AEROTHIONIN
from the sponge Aplysina aerophoba
Chem. Comm. 752 (1970)
1970
OCH3
Br
O
Br
HO
N CONHCH2CH2CH2CH2NHCO
O
N
OCH3
Br Br
OH
NITENIN
from the sponge Spongia nitens
1971
Tetrahedron, 27, 309 (1971)
The first furanoterpene from marine organisms
O
CO
O
H
O
OROIDINfrom the sponge Agelas oroides
The proposed uncorrect
structure
The first bromoalkaloid from marine organisms
Chem. Comm. , 1129 (1971)
1971
NH
CONH
N
NH
CH2NH2
Br
Br
NH
CONHBr
Br
NH
N NH2
CH2
SCALARIN
from the sponge Cacospongia scalaris
The starting point
of the “scalarane” sesterpenes
Tetrahedron, 28, 5993 (1972)
1972
OOCOCH3
O
HO
AXISONITRILE-1 – AXISOTHIOCYANATE-1from the sponge Axinella cannabina
The first isonitrile and
isothiocyanate
from marine organisms
Tetrahedron, 29 4259 (1973)
1973
N NCSC
CALYSTEROL from the sponge Calyx nicaensis
A unique cyclopropene-containing
sterol
Tetrahedron, 31, 1715 (1975)
1975
HO
CAULERPENYNEfrom the green alga Caulerpa prolifera
Tetrahedron Letters, 3593 (1978)
The well-known ecotoxin
of Caulerpa algae
1978
AcO
OAc
OAcH
AN UNBELIEVABLE ARRAY OF NEW
DITERPENE SKELETONS FROM THE RED ALGA
Sphaerococcus coroponifolius
and a biogenetic hypothesis
Gazz. Chim. It. 106, 779 (1976)
Tetrahedron Letters, 4123 (1981)
Tetrahedron Letters 25, 3141 (1984)
J. Org. Chem. 50, 3982 (1985)
Tetrahedron 42, 4273 (1986).
Gazz. Chim. It. 117, 87 (1987).
Phytochemistry 27, 621 (1988).
1976/1988
o
H
HH
HH
H
H2O
Br+
H
OH
Br
Br+
OH
Br
H
H
CH2Br
OPP
PROPOSED MECHANISM FOR THE BIOGENESIS OF
DITERPENES IN SPHAEROCOCCUS CORONOPIFOLIUS
Tetrahedron Letters 25, 3141 (1984)
CLATHRIDINE
FROM THE SPONGE Clathrina clathrus
Tetrahedron, 45, 3873 (1989) ; 46, 4387 (1990)
The first marine
alkaloid Zn complex
1990
N
N
N
N
N
O
OO
O
N
N
HN
N
N
O
O
O
O
Zn
INCISTEROLSfrom the sponge Dictyonella incisa
O
R
O
H3CO
H
R=
Unique sterols deriving
from a dramatic biodegradation
of the sterol nucleus
J. Am Chem Soc, 112, 3505 (1995)
1995
PLAKOSIDE A and Bfrom the sponge Plakortis simplex
OOH
H
H
HO
H
HOH
O
OH
Plakoside A: R =
Plakoside B: R =
ROH
OOH
NH
C10H21
C10H21
C10H21
Unique prenylated glycolipids
with immunosuppressive activity
J. Am. Chem. Soc., 119,12465 (1997)
1997
CARBOXYHOMOYESSOTOXINfrom contaminated Mytilus galloprovincialis
O
O
O
O
O
O
O
O
O
O
NaO3SO
NaO3SO Me
Me
Me
Me
Me
O
Me
40
( )n
41
COOH
OH
H
H
H H H HH
H
H
H
H
HH H
H
H
H
H
HO
A major toxin present in contaminated
Adriatic mussels
Chem Res. Tox.- 13, 770 (2000)
2000
HEXADECANOIC ACID 5’,6’,9’,10’,12’,13’,14’,16’,18’,18’,21’-UNDECACHLORO-
11’,15’,17’,22’,23’-PENTHYDROXY-1’-METHYL-7’-SULFOOXYTRICOS-2’-ENYL
ESTER
from contaminated Mytilus galloprovincialis
OH
O Cl
Cl
OSO3Cl
Cl
OH
Cl
Cl
Cl
OH
Cl
OH
Cl Cl
Cl
OH
C
O
(CH2)14
CH3
A unique chlorosulfolipid with a dense
functionalization of the alkenyl chain with
eleven chlorine atoms
J. Am. Chem. Soc., 124,13114 (2002)
2002
CLIONASTATIN A - Bfrom the burrowing sponge Cliona nigricans
OO
Cl Cl
Cl
H
OO
Cl Cl
Cl
H
Cl
•First polyhalogenated steroids found in nature•First halogenated androstanes found in nature
Org. Letters, 6, 1633 (2004)
From the comment of a Organic Letters REFEREE :
“Short of marinating the marine sponge in bleach after collection and before
extraction, I cannot see how this structure can arises, biosynthetically. It
challenges the conventional wisdoms of both the nature of halogenases
responsible for introduction of Cl into isoprenoid carbon skeletons and the
locus and detailed steps of nor-side-chain sterol biosynthesis within
invertebrates”.
2004
O
NH
S
O
O
OH
OOO
NH
S
O
O
OH
OO
A
B C D
ThiaplidiaquinonesThiaplidiaquinones AA--BB maymay targettarget thethe plasmaplasma membranemembrane redoxredox systemsysteminin thethe samesame wayway thatthat capsaicincapsaicin andand resiniferatoxinresiniferatoxin.. TheyThey produceproduce bothboth aadramaticdramatic increaseincrease inin thethe reactivereactive oxygenoxygen speciesspecies (ROS)(ROS) generationgeneration andand aafallfall inin thethe transmembranetransmembrane mitochondrialmitochondrial potentialpotential inducinginducing cellcell deathdeath bybyapoptosisapoptosis..
THIAPLIDINONE A – Bcytotoxic quinones from the marine
tunicate Aplidium conicum
J. Med Chem., 48, 3410-3416 (2005)
2004
O
H
HO
H
HO
H
OHH
O
O
OH
O
OH
NH OH
H
C13H27
C19H39
OHO
H
H
HO
H
OH
H H
O
OH
HO
H
OHH
HO
H
H
O
H
O
H2
O
H
HHO
H OH
OH
H
OH
OH
H
OH H
OH
HO
H
HO
HO
HO
OH
Vesparioside B Vesparioside B
from the spongefrom the sponge Spheciospongia vespariaSpheciospongia vesparia
The most complex
glycosphingolipid
isolated from
a marine
sponge to date
J. Org. Chem. 2008, 73, 6158–6165
2008
42-Hydroxy Palytoxin
O
OH
O
O
OH
O
OH
HO
OH
OHMe
O
HO
O
HO
Me
O
HO
O
O
OHHO
O
O
HN
O
NH
H2N
OH
HO
OH
OH
OH
OH
OH
OH
OH
OH
OH
OHOHHO
OH
OH
Me
MeOH
OHHO
OHOH
OH Me HO
OH
OH
OH
Me
Me
OH
HO
OH
HO
OH
OH
da
27
28
34
85
85' 84
86115
b
c
e
f
3948
2009
Chem. Res. in Toxicol, 22, 1851 (2009)
Hawaiian
Palythoa toxica
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