iridoids a pharmacists prospective...coumaroyl iridoids and a depside from cranberry (vaccinium...
TRANSCRIPT
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IRIDOIDS – A PHARMACISTS
PROSPECTIVE
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IRIDOIDS – A PHARMACISTS
PROSPECTIVE
Lecturis salutem!
My name is dr. ZSOLT PETENDI
I’m a pharmacist from Budapest, Hungary
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IRIDOIDS – A PHARMACISTS
PROSPECTIVE
Iridoids… are the
„materials of life”
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IRIDOIDS – A PHARMACISTS
PROSPECTIVE
The knowledge of pharmacists are fused together from
three parts: botany, chemisty, physiology.
So when I talk different audiences – even to healthcare
professionals’ – and I see the uncertain expression over
their faces when I say I will speak about the iridoids…
about the [yet] not-so-widely recognized new merits of
them I know first I need to brush up all what they
learned at the university. So I always follow this
sequence: BCP (botany, chemisty, physiology)
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IRIDOIDS – A PHARMACISTS
PROSPECTIVE
Iridoids can be found in a lot of plants, which have
mostly well-known and time-proven beneficial
effects; they are real medicinal – ethno-, and
folk medicinal plants.
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IRIDOIDS – A PHARMACISTS
PROSPECTIVE
Iridoids are secondary metabolites of different
plants* – they are not basically necessary for
the plant. Sometimes they are strong insect-
deterrents and they are often intermediers in the
process of alkaloid synthesis.
*and they can be found also in some animals
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IRIDOIDS – A PHARMACISTS
PROSPECTIVE
We find iridoids mostly in the following plant
families (I will speak only about some of them)
Ericaceae
Gentianacae
Lamiaceae
Loganiaceae
Menyanthaceae
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IRIDOIDS – A PHARMACISTS
PROSPECTIVE
(contd)
Oleaceae
Plantaginaceae
Rubiaceae
Scrophulariaceae
Valerianaceae
Verbenaceae
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IRIDOIDS – A PHARMACISTS
PROSPECTIVE
This plants have some common properties:
• they are well-known by the local inhabitans
and have been used since many hundred /
thousand years
• usually they can tolerate harsh conditions
(mechanical impacts, droughts etc.)
• they have few side effects (if any)
• they are widespread and cheap
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IRIDOIDS – A PHARMACISTS
PROSPECTIVE
Ericaceae (Heat/heather family)
Vaccinium myrtillus (Huckleberry)
(German: Heidelbeere, Heubeere, Schwarzbeere, Wildbeere,
Waldbeere, Bickbeere, Zeckbeere, Moosbeere)
Just to begin with: there are very few fruits
which contain iridoids. Vaccinium species are
one of them.
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IRIDOIDS – A PHARMACISTS
PROSPECTIVE
A book which is considered as a modern and the best guide in pharmabotanics is Hungary…
Prof Dr. Bela Danos:
Farmakobotanics – medicinal plants Third edition, Budapest 2003 (2006)
…doesn’t mention any iridoid-containing fruits except Vaccinium sp.
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IRIDOIDS – A PHARMACISTS
PROSPECTIVE
Ericaceae: Two iridoids were detected in 2002
with MS and NMR in different Vaccinium
berries (cranberry, lingonberry, blueberry):
monotropein and 6,7-dihydromonotropein
Jensen HD et al:
(…) iridoid glycosides in the juice of American and European cranberries (…)
J Agric Food Chem. 2002 Nov 6;50(23):6871-4.
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IRIDOIDS – A PHARMACISTS
PROSPECTIVE
Ericaceae: Jensen HD et al: Iridoids in Vaccinium berries:
Cranberry Lingonberry Blueberry
Vaccinium macrocarpon Vaccinium vitis-idaea Vaccinium
corymbosum
amerikai tőzegáfonya
(HU)
vörös áfonya
(HU)
fürtös áfonya
(HU)
red red dark blue
monotropein monotropein
6,7-dihydromonotropein 6,7-dihydromonotropein
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IRIDOIDS – A PHARMACISTS
PROSPECTIVE
Ericaceae:
Vaccinium corymbosum
(wikipedia)
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IRIDOIDS – A PHARMACISTS
PROSPECTIVE
Ericaceae:
Vaccinium macrocarpon
(wikipedia)
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IRIDOIDS – A PHARMACISTS
PROSPECTIVE
Ericaceae: Vaccinium macrocarpon A newer article:
Turner A et al:
Coumaroyl iridoids and a depside from cranberry (Vaccinium macrocarpon) J Nat Prod. 2007 Feb;70(2):253-8. Epub 2007 Feb 2.
Depsides are two or more monocyclic aromatic units linked by an ester bond; they have antibiotic1, anti-HIV2, antioxidant1, and anti-proliferative3 activity, they are good NSAID’s4.
1 Reynertson KA et al, (2006) 2 Neamati N et al (1997) 3 Kumar KC et al: (1999) 4
Sankava U et al: (1982)
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IRIDOIDS – A PHARMACISTS
PROSPECTIVE
Ericaceae:
Vaccinium vitis-idea
(wikipedia)
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IRIDOIDS – A PHARMACISTS
PROSPECTIVE
Ericaceae: Vaccinium berries in folk medicine:
Cranberry juice is a traditional folk remedy as a cure for
urinary infections, but also against diarrhea and
bowel problems.
Sometimes the juice and also its jam was and are
consumed for a – purported – better night vision.
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IRIDOIDS – A PHARMACISTS
PROSPECTIVE
Gentianaceae (Gentian) (GER: Enzian) (HU: tárnics)
The Gentianaceae family is a real treasury of iridoids:
their members are known for millenia (their name
comes from the Illyrian – Dalmatian – king Gentius,
who recommended it 2200 years ago against diarrhea
and severe fatigue).
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IRIDOIDS – A PHARMACISTS
PROSPECTIVE
Gentianaceae
When I decided to study articles about iridoid research I
collected cca 1.200 articles; almost 10% of them are
dealing with some Gentianaceae, thus making them
to the most represented plant family in my survey.
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IRIDOIDS – A PHARMACISTS
PROSPECTIVE
Gentianaceae
This plant family contains about 1.500 species1, the most known are Gentiana lutea, G. kurroo, G. algida, G. macrophylla, G. pedicellata, G. mansurica, G. rhodantha, G. scabra etc. Many of them are used as a medicinal plant.
1Struwe L et al (editors)
Gentiananceae
Cambridge University Press 2002
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IRIDOIDS – A PHARMACISTS
PROSPECTIVE
Gentianaceae
Gentianaceae have a horribly strong bitter taste: amarogentin is
bitter even at 1:50.000.000 dilution. But this bitter taste works
sometimes wonders: all the world is producing different
alcoholic and non-alcoholic extracts.
Bitters have a tremendous popularity: little old ladies, who never
consider drinking rub their aching joints and use the ‘Bitter’ to
every thinkable complaints and ailments.
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IRIDOIDS – A PHARMACISTS
PROSPECTIVE
Gentianaceae There are about 5.000 major bitters
produced worldwide – some of them:
Angostura, Becherovka, Boonekamp's, Campari,
Cynar, Demänovka, Fernet Branca,
Jägermeister, Luxardo, Pelinkovac, Pimm's,
Ramazotti, Suze, Swedish bitters, Underberg,
Unicum…
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IRIDOIDS – A PHARMACISTS
PROSPECTIVE
Gentianaceae
Purported medicinal properties of bitters
Bitters are alleged to have restorative properties.
They were reported to be a remedy for hiccups, an
upset stomach -- but manufacturers were not very
faint-hearted…
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IRIDOIDS – A PHARMACISTS
PROSPECTIVE
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IRIDOIDS – A PHARMACISTS
PROSPECTIVE
Gentiana ssp. (wikipedia)
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IRIDOIDS – A PHARMACISTS
PROSPECTIVE
Gentiana ssp. (wikipedia)
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IRIDOIDS – A PHARMACISTS
PROSPECTIVE
Gentiana lutea (wikipedia)
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IRIDOIDS – A PHARMACISTS
PROSPECTIVE
The basic structure of the iridoids are simple: an
oxygen-containing heterocyclic ring and a
cyclopentane ring fused together.
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IRIDOIDS – A PHARMACISTS
PROSPECTIVE
Iridoids are monoterpenes; they are synthethised in
the plants and animals from isoprene and they
are often the intermediers in the synthesis of
alkaloids.
(Human body synthetises cholesterol and Q10
from isoprene, and natural rubber is made also
from isoprene).
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IRIDOIDS – A PHARMACISTS
PROSPECTIVE
Isoprene, C5H8, (2-metil-1,3-butadiene)
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IRIDOIDS – A PHARMACISTS
PROSPECTIVE
The name „iridoids” originates from the name of
an ant species (Iridomyrmex). It was discovered
it that insects.
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IRIDOIDS – A PHARMACISTS
PROSPECTIVE
Iridomyrmex humilis
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IRIDOIDS – A PHARMACISTS
PROSPECTIVE
These ants, Iridomyrmex humilis – (argentin ant) –
are producing iridoids. There was earlier a
hypothesis that they have it as deterrent against
their enemies.
It was discovered only two years ago (in 2009)
that iridoids are playing a greater role: maybe
they are one of the real „material of life”!
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IRIDOIDS – A PHARMACISTS
PROSPECTIVE
„Don’t bury me, I’m alive” that is the message of iridoids in the ants.
So iridoids are linked to a healthy life in a way that maybe we don’t even realise the extent and importance of it.
Ants can smell things very well. They detect the difference between their family and others. It is hardly to believe that they couldn’t smell the smell of decomposing tissues of a dead ant… But iridoids are so important that without it there is no life. At least no ant-life.
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IRIDOIDS – A PHARMACISTS
PROSPECTIVE
Two entomologists, Rust and Jocelyn Millar
worked together with a researcher in the field
of analitycal chemistry named Choe isolating
the „life signals” at the ants. They are
dolichodial and iridomyrmecin.
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IRIDOIDS – A PHARMACISTS
PROSPECTIVE
„These materials or their slightly modified forms
are common at many ant species. And these
ants all perform necroforesis” – says Choe.
„But at these ants necroforesis is triggered
through the absence of life signals, and not
the deteriorating effects of death itself.”
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IRIDOIDS – A PHARMACISTS
PROSPECTIVE
The researchers told that this two chief materials –
dolichodial és iridomyrmecin – or their
slightly modified versions are found at very
many other insects, too.
http://www.hirado.hu/Hirek/2009/05/07/09/Hogyan_ismerik_fel.aspx
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IRIDOIDS – A PHARMACISTS
PROSPECTIVE
This is dolichodial – the ‘material of life’ – the ants
are proving with this (and with iridomyrmecin) to their
fellow comrades that they are still alive.
Structure of dolichodial
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IRIDOIDS – A PHARMACISTS
PROSPECTIVE
Iridomyrmecin, C10H16O2
• molar weigh: 168,24
• CAS: 485-43-8
• can be found in Actinidia polygama
• and has antibiotic properties – like so many
other iridoids.
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41
IRIDOIDS – A PHARMACISTS
PROSPECTIVE
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42
IRIDOIDS – A PHARMACISTS
PROSPECTIVE
Google: ne temessetek el, még élek
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43
IRIDOIDS – A PHARMACISTS
PROSPECTIVE
Plant of Morinda citrifolia is used by ants (Oecophylla smaragdina)…
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44
IRIDOIDS – A PHARMACISTS
PROSPECTIVE
There are insects which are synthetising iridoids
de novo but mostly they consume ready
iridoids; they are caterpillars. And at some
species iridoids are ‘inherited’ to their
butterflies, too.
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45
IRIDOIDS – A PHARMACISTS
PROSPECTIVE
This is the „chequered Baltimore buttterfly”
(Euphydryas phaeton)
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46
IRIDOIDS – A PHARMACISTS
PROSPECTIVE
Euphydryas phaeton
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47
IRIDOIDS – A PHARMACISTS
PROSPECTIVE
And this is the caterpillar of Euphydryas phaeton
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48
IRIDOIDS – A PHARMACISTS
PROSPECTIVE
Its host plant is Aureolaria flava
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49
v IRIDOIDS – A PHARMACISTS
PROSPECTIVE
…which can be easily recognised as the
member of the family Scrofulariaceae.
This family has many well-known and widespread
medicinal plants, (e.g Linaria officinalis).
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IRIDOIDS – A PHARMACISTS
PROSPECTIVE
There is much research matter about the
iridoid-consuming habits of butterflies but
the real goal of this phenomenon is still
unclear. Surely the deterrent effect (bitter
taste!) is of one of them, but antibiotic effect
also can play an important role.
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IRIDOIDS – A PHARMACISTS
PROSPECTIVE
Butterfly Host plant
Euphydryas phaeton Aureolaria flava
Euphydryas phaeton Plantago lanceolata
E. chalcedona Scrophularia californica
E. anicia Besseya plantaginea
Poladryas arachne Penstemon virgatus
Junonia coenia Plantago lanceolata
Ptatyptila pica Castilleja sulphurea
Meris alticola Besseya plantaginea
Ceratomia catalpae Catalpa bignonioides
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52
IRIDOIDS – A PHARMACISTS
PROSPECTIVE
Members of the Rubiaceae family (relatives of
Morinda citrifolia) has iridoids in abundant
quantity.
So in Asperula odorata is asperuloside acid (AA).
Its deacetil compound is one of the most important
iridoids in TNBB (DAA)
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53
IRIDOIDS – A PHARMACISTS
PROSPECTIVE
Basic iridoid research is commenced by a pharmacist named
Prof. Emile Bourquelot (1851-1921)
who was researching and teaching at the Universiy of Paris. He was also a pioneer in the field of enzymology; therefore his students named him lovingly „professeur Bourquelase”.
He said often that iridoids are playing a very important role in the healing of different illnesses.
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IRIDOIDS – A PHARMACISTS
PROSPECTIVE
Structure identification of the iridoids started
also a half century ago – in the beginning of
the ’60es.
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IRIDOIDS – A PHARMACISTS
PROSPECTIVE
Research showed the exact structure of
iridoids – that is the structure of their
glycosid parts.
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IRIDOIDS – A PHARMACISTS
PROSPECTIVE
A typical iridoid is loganin, which is found in the
seeds of Strychnos nux-vomica relatively
abundantly (4-5% w/w). (The well-known
alkaloid of the same plant is strychnine).
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IRIDOIDS – A PHARMACISTS
PROSPECTIVE
Loganin,
C17 H26 O10
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58
IRIDOIDS – A PHARMACISTS
PROSPECTIVE
The structures of
plumericin (antimicrobial effects, from Plumeria multiflora)
and allamandin (antineoplastic effect, mainly by leukemia, from Allamanda cathartica)
are very similar, too.
This materials are well-researched and have a long history. Their structure was identified many decades ago (plumericin’s in 1951, allamandin’s in 1974) by Little JE et al, and Kupchan SM et al., respectively.
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IRIDOIDS – A PHARMACISTS
PROSPECTIVE
If the cyclopentane ring is popened than we get the
group of secoiridoids.
A very important and well-known secoiridoid is
secologanin which is common in the sweet-
smelling plant family of Caprifoliaceae.
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IRIDOIDS – A PHARMACISTS
PROSPECTIVE
Secologanin is the precursor of many alkaloids: about one quarter (25%) of all alkaloids are synthetised from it.
Among these alkaloids are such important ones which was (and sometimes still can) to be found in pharmacies, and which were used for healing for very long times. (Cinchona-, and
Ipecac-alkaloids). (kinin=fever and
emetin=cough).
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IRIDOIDS – A PHARMACISTS
PROSPECTIVE
Iridoids in folk medicine
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IRIDOIDS – A PHARMACISTS
PROSPECTIVE
Medicinal plants, containing iridoids and
secoiridoids are tresured remedies of the folk
medicine and are used mostly for very long
times.
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IRIDOIDS – A PHARMACISTS
PROSPECTIVE
Some time-, and research- proven iridoid effects are:
1. painkiller, antidoloricum (Verbena off.)
2. against inlammations, antiphlogisticum (Euphrasia off., Verbena off.)
3. against cramps, antispasticum (Valeriana)
4. against cancer, antineoplasticum (Morinda citrifolia, Allamanda catarthica),
5. antibacterial (Plantago lanceolata)
6. booster of the immune system (Harpagophyton)
7. lowering the level of blood sugar (Morinda citrifolia)
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IRIDOIDS – A PHARMACISTS
PROSPECTIVE: PHYSIOLOGY
Eyebright ((Euphrasia officinalis; Augentrost in
German) is very good against all kind of eye
inflammations and has a mild laxative and
fiuretic effect, too. It contains eufroside,
aucubin and catalpol.
It’s interesting that aucubin is active only in its
aglycon form (in the presence of the enzyme ß-
glucozidase).
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IRIDOIDS – A PHARMACISTS
PROSPECTIVE
Eyebright (Euphrasia officinalis)
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IRIDOIDS – A PHARMACISTS
PROSPECTIVE
Valerian (Baldrian in German), Valeriana
officinalis contains the iridoid valepotriate
which is a potent tranquillant. The name of this
plant in hungarian is „cats’ root”.
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IRIDOIDS – A PHARMACISTS
PROSPECTIVE
Valeriana officinalis
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IRIDOIDS – A PHARMACISTS
PROSPECTIVE
Valeriana officinalis is a good exemple to show
the complex and synergistic effects of plants;
beside its good iridoid content
its valerenic acids are inhibiting the enzyme which
disintegrates GABA (Gamma Amino Butyric Acid,
an important neurotransmitter in the brain with
tranquilizing effect) so there remains more GABA
and the extract of Valeriana, (Tinctura valerianae
in the pharmacy) contains also GABA, too.
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IRIDOIDS – A PHARMACISTS
PROSPECTIVE
But Tinctura valerianae (either the aetherea or
spirituosa) has a horrible taste and an
unpleasant odor – some would name it pungent
stench; they are right, believe me…
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IRIDOIDS – A PHARMACISTS
PROSPECTIVE
…but cats have an opposite opinion.
Cats become delirious when they encounter with
Valeriana (remember the hungarian name cats’
root!) – if they can they try to get the plant’s
root, they chew it, but they like notoriously the
similar Nepeta cataria also.
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IRIDOIDS – A PHARMACISTS
PROSPECTIVE
Nepeta cataria
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IRIDOIDS – A PHARMACISTS
PROSPECTIVE
Nepeta cataria has several iridoids:
nepetalacton is good against fever
(febrifugium) against cramps
(antispasticum) and has antimicrobial
effect and is a good and mild
tranquillant.
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IRIDOIDS – A PHARMACISTS
PROSPECTIVE
Different iridoids are the key of the
beneficial effects of many medicinal
plants.
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IRIDOIDS – A PHARMACISTS
PROSPECTIVE
Simple iridoids: (C9 – C10) Boschniakia rossica
Teucrium marum
Myoporum ssp.
Actinidia polygama
Nepeta cataria
![Page 75: IRIDOIDS A PHARMACISTS PROSPECTIVE...Coumaroyl iridoids and a depside from cranberry (Vaccinium macrocarpon) J Nat Prod. 2007 Feb;70(2):253-8. Epub 2007 Feb 2. Depsides are two or](https://reader033.vdocument.in/reader033/viewer/2022060916/60a9b95be2e6fd2525109d3f/html5/thumbnails/75.jpg)
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IRIDOIDS – A PHARMACISTS
PROSPECTIVE
Secoiridoid glycosids: (C16 – C29) Gentiana lutea
Olea europaea
Lonicera,Vinca rosea
Swertia japonica
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IRIDOIDS – A PHARMACISTS
PROSPECTIVE
Iridoid glycosids I. (C15 – C22) Vitex agnius-castus
Antirrhinum majus
Asperula odorata
Aucuba japonica
Catalpa, Plantago
Catalpa speciosa
Strychnos, Menyanthes
Glandifora ssp.
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IRIDOIDS – A PHARMACISTS
PROSPECTIVE
Iridoid glycosids II. (C15 – C22) Gardenia, Cornus
Harpagophytum procumbens
Strychnos nux-vomica
Monotropa, Pyrola sp.
Paederia scandens
Plumeria acutifolia
Gardenia sp.
Verbena officinalis
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IRIDOIDS – A PHARMACISTS
PROSPECTIVE
Nonglycosid iridoids: (C11 – C22) Allamanda cathartica
Valeriana, Centranthus
Plumeria ssp.
Genipa americana
Plumeria multiflora
Valeriana, Centrarthus
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IRIDOIDS – A PHARMACISTS
PROSPECTIVE
Summarised: the iridoids
are found in dozens of medicinal plants,
are deeply rooted and effectively used in the
folk medicine
and their research is continued during 50-60, but
sometimes more than 100 years.
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IRIDOIDS – A PHARMACISTS
PROSPECTIVE
But it’s not a simple task to apply evenly and
effectively green and dry plant materials to the
human body – I mean poor adsorption because
poor gut flora, the problems of equal doses etc.
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And besides, as it was mentioned, iridoids are very
bitter – that’s why they are in the plants.
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Amarogentin it’s the etalon
of bitterness
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So we should have a fruit, with good, at least with tolerable taste… from which we could make a liquid form: easy application, good bioavailability, and maybe more iridoids
than in the modest cranberries (2).
We should develop a DESIGNER FRUIT, right?!
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Maybe with 5 or 6 iridoids? Much more
than any other known fruit? A new
champion?
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Me, as a pharmacist of decades,
continuosly learning and working
cannot hide my joy, wondering – and
kind of embarrasment – that a Great
Designer already made this fruit and
that I can be the part of this emerging
miracle.
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Morinda citrifolia has twelve iridoids
(maybe more…). I can’t explain such
difference between ordinary fruits and
noni.
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But for the healthcare professionals who
are now getting acquinted with Tahitian
Noni® Bioactives surely iridoids are the
most interesting…
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…because iridoids
have long and rock-solid research,
TNBB has lot of them
and their bioavailibility is exceptionally
good.
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Good bioavailibility in the human body is
greatly determined by two important
factors: solubility and physical /
chemical stability.
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Iridoids in noni have
1) good solubility so they are easily
adsorbed
2) they are very resistent to chemical
degradation during manufacturing and shelf-
life (but flavonoids aren’t!)
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So TNBB is the world’s first – and still
the only – fruit-based bioactive drink.
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For a pharmacist it is very important that
Tahitian Noni Bioactive BeverageTM
has a very profound quality insurance and
quality checking system (GMP, GAP, GHP)
was already researched in 14 human clinical
trial
and that its’s iridoid content is declared,
constant and can be every time verified.
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Tahitian Noni Bioactive Beverage® has an
innovative, modern design…
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…and tartes sooo good! (It’s a subjective
and a personal opinion).
Thank you for your attention!