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

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Presentation on theme: "Herbs and raw stuff that contain iridoids. phenol compounds, simple phenols and their glycosides."— Presentation transcript:

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

2 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.

3 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).

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5 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

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

7 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.

8 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.

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10 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.

11 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.

12 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

13 Irydodial l Dialdehyde form Enolsemiacetic form

14 Simple iridoids and their glycoside Aucubin Loganin

15 Iridoids with opening pentane cycle Secologanin

16 Acyl derivatives 1. Valepotriates (nonglycosides compounds ) ValtratDihydrovaltrat

17 2. Iridoid’s glycosides with С7-С8 double bond Iridoid-alkaloids – the complex indolic alkaloids, which nonaminic part is iridoid. Asperuloside

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19 BAS: 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. MENYANTHIDIS FOLIA Menyanthes trifoliata L- Bogbean Menyanthaceae 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 : Water extract. Enters in the complement of appetizing, sedative collections. Dosage forms: Water extract. Enters in the complement of appetizing, sedative collections.

20 CENTAURII HERBA Centaurium erythraea Raft (С. minus, C. umbellatum) Centaury Gentianaceae BAS: 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.

21 Pharmacological properties Combination 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)

22 GENTIANAE RADICES GENTIANA LUTEA GENTIANACEAE BAS: 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.).

23 VIBURNI CORTEX VIBURNI CORTEX VIBURNUM OPULUS—CRAMP BARK The dried bark of Viburnum opulus BAS: 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.).

24 VALERIANAE RADICES – Valerian root, EuPh P. 3174 VALERIANAE RADICES – Valerian root, EuPh P. 3174 Valeriana officinalis VALERIANACEAE BAS: 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.).

25 DEFINITION 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 drug); — 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 drug).

26 IDENTIFICATION 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.

27 TESTS 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. ASSAY 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)

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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

30 CARDIOVALEN is applied at the neuro- circulatory dystonia in complex therapy of chronic hart failure. Treating the cardiovascular neurosis, accompanied by bradycardia.

31 Taraxaci Radices Taraxacum officinale- Dandelion Asteraceae BAS: 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.

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