herbs and raw stuff that contain iridoids. phenol compounds, simple phenols and their glycosides

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Herbs and raw stuff that contain iridoids. phenol compounds, simple phenols and their glycosides

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Page 1: Herbs and raw stuff that contain iridoids. phenol compounds, simple phenols and their glycosides

Herbs and raw stuff that contain iridoids. phenol compounds, simple phenols and their glycosides

Page 2: 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.

Page 3: Herbs and raw stuff that contain iridoids. phenol compounds, simple phenols and their glycosides

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).

Page 4: Herbs and raw stuff that contain iridoids. phenol compounds, simple phenols and their glycosides
Page 5: Herbs and raw stuff that contain iridoids. phenol compounds, simple phenols and their glycosides

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

Page 6: Herbs and raw stuff that contain iridoids. phenol compounds, simple phenols and their glycosides

A rational classification of the terpenes has been established based upon the number of isoprene (or isopentane) units incorporated in the basic

molecular skeleton:

Page 7: Herbs and raw stuff that contain iridoids. phenol compounds, simple phenols and their glycosides

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 functions.

Page 8: Herbs and raw stuff that contain iridoids. phenol compounds, simple phenols and their glycosides

Iridoids

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 alkaloids.

Page 9: Herbs and raw stuff that contain iridoids. phenol compounds, simple phenols and their glycosides
Page 10: Herbs and raw stuff that contain iridoids. phenol compounds, simple phenols and their glycosides

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.

Page 11: Herbs and raw stuff that contain iridoids. phenol compounds, simple phenols and their glycosides

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, anti-inflammatory, antimutagenic, antispasmodic, antitumor (valtrate), antiviral, immunomodulator, and purgative activities.

Page 12: Herbs and raw stuff that contain iridoids. phenol compounds, simple phenols and their glycosides

Classification

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, dihydrovaltrate.

4. Iridoids-alcaloids – complex of indole alcaloids containing as non-amine part iridoid

Page 13: Herbs and raw stuff that contain iridoids. phenol compounds, simple phenols and their glycosides

Irydodiall

Dialdehyde form

Enolsemiacetic form

Page 14: Herbs and raw stuff that contain iridoids. phenol compounds, simple phenols and their glycosides

Simple iridoids and their glycoside

Aucubin Loganin

Page 15: Herbs and raw stuff that contain iridoids. phenol compounds, simple phenols and their glycosides

Iridoids with opening pentane cycle

Secologanin

Page 16: Herbs and raw stuff that contain iridoids. phenol compounds, simple phenols and their glycosides

Acyl derivatives

1. Valepotriates (nonglycosides compounds)

Valtrat Dihydrovaltrat

Page 17: Herbs and raw stuff that contain iridoids. phenol compounds, simple phenols and their glycosides

2. Iridoid’s glycosides with С7-С8 double bond

Iridoid-alkaloids – the complex indolic alkaloids, which nonaminic part is iridoid.

Asperuloside

Page 18: Herbs and raw stuff that contain iridoids. phenol compounds, simple phenols and their glycosides
Page 19: Herbs and raw stuff that contain iridoids. phenol compounds, simple phenols and their glycosides

BASBAS:: 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.

MENYANTHIDISMENYANTHIDIS FOLIA FOLIA Menyanthes trifoliata L- BogbeanMenyanthaceae

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 Water extract. Enters in the complement of appetizing, sedative collections.appetizing, sedative collections.

Page 20: Herbs and raw stuff that contain iridoids. phenol compounds, simple phenols and their glycosides

CENTAURII HERBA Centaurium erythraea Raft (С. minus, C. umbellatum)CentauryGentianaceae

BASBAS::. 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.

Page 21: Herbs and raw stuff that contain iridoids. phenol compounds, simple phenols and their glycosides

Pharmacological propertiesCombination remedy of the nature origin, that has diuretic, spasmolytic ,

antiinflammatory, antimicrobial activity. Prescription

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)

Page 22: Herbs and raw stuff that contain iridoids. phenol compounds, simple phenols and their glycosides

GENTIANAEGENTIANAE RADICES RADICES GENTIANA LUTEAGENTIANA LUTEA GENTIANACEAE GENTIANACEAE

BASBAS:: 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.).

Page 23: Herbs and raw stuff that contain iridoids. phenol compounds, simple phenols and their glycosides

VIBURNIVIBURNI CORTEX CORTEX VIBURNUM OPULUS—CRAMP BARKThe dried bark of Viburnum opulus

BASBAS:: 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.).

Page 24: Herbs and raw stuff that contain iridoids. phenol compounds, simple phenols and their glycosides

VALERIANAEVALERIANAE RADICES – RADICES – Valerian root, EuPh P. 3174Valerian root, EuPh P. 3174

Valeriana officinalisVALERIANACEAE

BASBAS:: 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.).

Page 25: Herbs and raw stuff that contain iridoids. phenol compounds, simple phenols and their glycosides

DEFINITIONDried, whole or fragmented underground parts of Valerianaofficinalis L. s.l., including the rhizome surrounded by theroots 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) (drieddrug);— cut drug:— essential oil : minimum 3 ml/kg (dried drug) ;— sesquiterpenic acids : minimum 0.10 per cent m/mexpressed as valerenic acid (C15H22O2 ; Mr 234.3) (drieddrug).

Page 26: Herbs and raw stuff that contain iridoids. phenol compounds, simple phenols and their glycosides

IDENTIFICATIONA. 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.

Page 27: Herbs and raw stuff that contain iridoids. phenol compounds, simple phenols and their glycosides

TESTSForeign matter (2.8.2): maximum 5 per cent of stem basesand maximum 2 per cent of other foreign matter.Loss on drying (2.2.32) : maximum 12.0 per cent, determinedon 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.

ASSAYEssential 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)

Page 28: Herbs and raw stuff that contain iridoids. phenol compounds, simple phenols and their glycosides
Page 29: Herbs and raw stuff that contain iridoids. phenol compounds, simple phenols and their glycosides

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

Page 30: Herbs and raw stuff that contain iridoids. phenol compounds, simple phenols and their glycosides

CARDIOVALEN is applied at the neuro-circulatory dystonia in complex therapy of chronic hart failure.

Treating the cardiovascular neurosis, accompanied by bradycardia.

Page 31: Herbs and raw stuff that contain iridoids. phenol compounds, simple phenols and their glycosides

Taraxaci Radices Taraxacum officinale- DandelionAsteraceae

BASBAS:: 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.

Page 32: Herbs and raw stuff that contain iridoids. phenol compounds, simple phenols and their glycosides