04. Herbs and raw stuff that contain iridoids

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Transcript 04. Herbs and raw stuff that contain iridoids

Herbs and raw stuff
that contain iridoids.
phenol compounds,
simple phenols and
their glycosides
The terpenoids sometimes called
isoprenoids, are a large and diverse class
of naturally occurring organic chemicals
similar to terpens, derived from five-carbon
isoprene units assembled and modified in
thousands of ways.
Terpenoids are extraordinarily diverse but they all
originate through the condensation of the
universal phosphorylated derivative of
hemiterpene, isopentenyl diphosphate (IPP) and
dimethylallyl diphosphate (DMAPP) giving geranyl
pyrophosphate (GPP).
In higher plants, IPP is derived from the classic
mevalonic acid pathway in the cytosol but from the
methylerythritol phosphate pathway in plastids. It
is generally accepted that the cytosolic pool of IPP
serves as a precursor of sesquiterpenes,
triterpenes, sterols and polyterpenes whereas the
plastid pool of IPP provides the precursors of
mono-, di- and tetraterpenes
A rational classification of the terpenes has been
established based upon the number of isoprene
(or isopentane) units incorporated in the basic
molecular skeleton:
Importance of terpenoids
 Plant terpenoids are used extensively for their
aromatic qualities. They play a role in traditional
herbal remedies and are under investigation for
antibacterial, antineoplastic, and other pharmaceutical
 Iridoids are a class of secondary
metabolites found in a wide variety of
plants and in some animals. They are
monoterpenes biosynthesized from
isoprene and they are often
intermediates in the biosynthesis of
Chemically, the iridoids usually consist of a
cyclopentane pyran ring. The chemical structure is
exemplified by iridomyrmecin, a defensive
chemical produced by the iridomyrmee genus, for
which iridoids are named.
Bioactivities of iridoids
 Iridoids are found in many medicinal plants and
may be responsible for some of their
pharmaceutical activities. Iridoids exhibit a wide
range of bioactivities including stimulation of
secretions in the gastrointestinal tract, choleretic,
antimicrobial, cardiovascular and sedative
(valeopotriates), antihepatotoxic, diuretic
(catalpol), hypoglycemic, analgesic, antiinflammatory, antimutagenic, antispasmodic,
antitumor (valtrate), antiviral, immunomodulator,
and purgative activities.
 1. Cyclopentan C8,C9,C10 and C14 types
(Loganin, aucubin).
 2. Secoiridoids. Cleavage of bound in
thecyclopentane ring gives rise to secoiridiids.
(Secologanin, gentiopicroside, oleuropine)
 3. Iridoids of plant from family Valerianaceae
Bicyclic monoterpens or valepotriates
(‘Valeriana – Epoxy – triester’) Valtrate,
 4. Iridoids-alcaloids – complex of indole
alcaloids containing as non-amine part iridoid
Simple iridoids and their glycoside
Iridoids with opening pentane cycle
Acyl derivatives
Valepotriates (nonglycosides compounds)
2. Iridoid’s glycosides with С7-С8 double
Iridoid-alkaloids – the complex indolic alkaloids,
which nonaminic part is iridoid.
Menyanthes trifoliata LBogbean
BAS: Leaves contain bitter
amorphous glycoside of meniantin, at a
hydrolysis fissioning on glucose and
meniantol; alkaloid of gencianin,
flavonoids of rutins and giperozid,
ascorbic acid, and also tannic matters
to 3%. Roots contain glycoside is a
meliatin, tannic matters, inulin, pectin
matters and tracks of alkaloids.
Pharmacological activity: natural physiological
stimulant of secretion of saliva, gastric juice, bile and digestive enzymes; anti sclerotic; the
presence of organic compounds of iodine in the leaves of witch hinders to the accumulation of
cholesterol in an organism
Dosage forms: Water extract. Enters in the complement of appetizing,
sedative collections.
Centaurium erythraea Raft (С. minus, C.
BAS:. A plant contains 0,6-1% alkaloids,
among them basic gencianin (eritricin):
glycosides (genciopikrin, eritrocentaurin,
eritritaurin); flavonoid, xantons, oleanolic
and ascorbic acids, essential oil, resins
Pharmacological activity: Preparations of centaury as bitter taste is excited
appetite, strengthen the secretion of digestive glands, strengthen
zhelcheotdelenie, possess poslablyayuschimi and by protivoglistnymi
properties (genciopikrin).
Dosage forms: A grass of centaury is in packs. Extract. Collections
appetizing and stomach.
Pharmacological properties
Combination remedy of the nature origin, that has diuretic, spasmolytic ,
antiinflammatory, antimicrobial activity.
It’s used in the complex therapy at chronic bladder infection
(cystitis) and kidney (pyelonephritis), uninfected chronic inflammation of
kidney (glomerulonephritis), as an agent that prevents the formation of
kidney stones (also after the removal of stones)
BAS: gentiopicrin, gentisin, The root
also contains from 12 to 15 per cent.
of glucose (gentianose), but is
remarkable in that it contains no
starch, calcium oxalate, or tannin.
Preparation of Gentisic Acid : The alcoholic extract is washed with water, then with ether.
The residue dissolved in alcohol yields the acid on evaporation.
ACTION AND USES.—Simple bitter tonic, long known and very valuable.
Dose: 5 to 30 gr. (0.3 to 2 Gm.).
The dried bark of Viburnum opulus
BAS: A brown resin, a bitter principle
(viburnin), valerianic acid, tannic acid,
oxalic, malic, and citric acids,
sulphates, and chlorides, opulus iridoid
ACTION AND USES: Diuretic, and a tonic and
sedative to the uterine and ovarian nerve centers; used in threatened abortion.
Dose: 30 to 60 gr. (2 to 4 Gm.). Claimed to be antispasmodic, hence the name
cramp bark. Dose: 30 gr. to 2 dr. (2 to 8 Gm.).
Valerian root, EuPh P. 3174
Valeriana officinalis
BAS: Besides the common vegetable
principles, it contains a terpene,
isovaleric acid, and a volatile oil of
complex constitution, consisting mainly of
an alcohol, borneol; its ether, and its
formic, acetic, and valerianic acid
esters, which are gradually decomposed
on exposure, liberating the acids.
This oil (Oleum Valerian.,)
ACTION AND USES.—Gentle nerve stimulant and
antispasmodic, employed in hysterical disorders.
Dose: 15 to 60 gr. (1 to 4 Gm.).
Dried, whole or fragmented underground parts of Valeriana
officinalis L. s.l., including the rhizome surrounded by the
roots and stolons.
Content :
— whole or fragmented drug:
— essential oil : minimum 4 ml/kg (dried drug) ;
— sesquiterpenic acids : minimum 0.17 per cent m/m,
expressed as valerenic acid (C15H22O2 ; Mr 234.3) (dried
— cut drug:
— essential oil : minimum 3 ml/kg (dried drug) ;
— sesquiterpenic acids : minimum 0.10 per cent m/m
expressed as valerenic acid (C15H22O2 ; Mr 234.3) (dried
A. The rhizome is yellowish-grey or pale brownish-grey, obconical to cylindrical, up to
about 50 mm long and 30 mm in diameter ; the base is elongated or compressed,
usually entirely covered by numerous roots. The apex usually exhibits a cup-shaped
scar from the aerial parts; stem bases are rarely present. When cut longitudinally, the
pith exhibits a central cavity transversed by septa. The roots are numerous, almost
cylindrical, of the same colour as the rhizome, 1-3 mm in diameter and sometimes more
than 100 mm long. A few filiform fragile secondary roots are present. The fracture is
short. The stolons show prominent nodes separated by longitudinally striated internodes,
each 20-50 mm long, with a fibrous fracture.
B. The powder shows the following diagnostic characters : cells containing a pale brown
resin or droplets of essential oil; groups of small, rectangular sclereids with thick walls
and a narrow, channelled branched lumen; occasional groups of larger, thinner-walled
sclereids from the stem bases; lignified, reticulately-thickened vessels, singly or in small
groups; thin-walled, elongated cells of the piliferous layer, some with root hairs ;
occasional fragments of cork. Examine under a microscope using a 50 per cent V/V
solution of glycerol R. The powder shows abundant starch granules, mainly compound
with up to 4-6 components but frequently separated to form single granules, rounded to
irregular and up to about 15 μm in diameter ; most of the granules show a rather
indistinct cleft or radiate hilum.
C. Thin-layer chromatography.
Reference solution. Dissolve 5 mg of acetoxyvalerenic acid R and 5 mg of valerenic acid
R in 20 ml of methanol R.
Foreign matter (2.8.2): maximum 5 per cent of stem bases
and maximum 2 per cent of other foreign matter.
Loss on drying (2.2.32) : maximum 12.0 per cent, determined
on 1.000 g of well homogenised powdered drug by drying in an oven at 105 °C for 2 h.
Total ash (2.4.16) : maximum 12.0 per cent.
Ash insoluble in hydrochloric acid (2.8.1) : maximum 5.0 per cent.
Essential oil (2.8.12). Use 40.0 g of freshly powdered drug, a 2000 ml flask, 500 ml
of water R as the distillation liquid and 0.50 ml of xylene R in the graduated tube. Distil at
a rate of 3-4 ml/min for 4 h.
Sesquiterpenic acids. Liquid chromatography (2.2.29)
Pharmacotherapeutic group. Combined cardiac remedies.
At the functional cardio-vessel disorders Cardiophyt acts as cardiotonic,
antiarrhythmic and mild hypotension agent. In the combination therapy Cardiophyt
optimizes the action of the antianginal, antihypertensive and antiarrhythmic drugs.
Cardiophyt has a mild sedative effect, reduces the manifestation of diencephalic
disorders, improves the general condition of patients, exercise tolerance, promoting
optimal activity of patient. KARDIOFIT day the application does not cause
drowsiness and general flabbiness The drug has a mild sedative effect, reduces the
expression diencephalic disorders, improves the general condition of patients, exercise
tolerance, promoting optimal performance. The ingestion of Cardiophyt in the day
does not cause drowsiness and general flabbiness
CARDIOVALEN is applied at the neurocirculatory dystonia in complex therapy
of chronic hart failure.
Treating the cardiovascular
neurosis, accompanied by
Taraxaci Radices
Taraxacum officinale- Dandelion
BAS: Taraxacin (a bitter principle),
taraxacerin,resin, inulin, sugar, and
mucilaginous substances. Recent investigations
have shown the existence of an alkaloid.
Preparation of Taraxacin.—Treat decoction with
animal charcoal, wash the latter with water, and
dissolve out bitter principle with boiling alcohol;
evaporate. It has not been proven that this is
crystalline. Composition uncertain.
ACTION AND USES.—Deobstruent, tonic. As a remedial agent
dandelion root has not been properly appreciated, possibly because it is
such a common weed. It is worthy of more study on the part
of pharmaceutical chemists and clinicians. The liquid extract and
extract are used in hepatic disorders.