mp and mpm containing steroidal saponins

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MP and MPM containing MP and MPM containing steroidal saponins steroidal saponins

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Page 1: MP  and MPM containing steroidal  saponins

MP and MPM MP and MPM containing steroidal containing steroidal

saponinssaponins

Page 2: MP  and MPM containing steroidal  saponins

SaponinsSaponins (Latin sapo, soap) are (Latin sapo, soap) are characterized by their property of characterized by their property of

producing a frothing aqueous producing a frothing aqueous solution, possessing a high solution, possessing a high

surface activity. They also have surface activity. They also have haemolytic properties, and then haemolytic properties, and then

injected into the blood stream are injected into the blood stream are highly toxic. They can cause the highly toxic. They can cause the death of cold blooded animals death of cold blooded animals such as frogs, worms and fish such as frogs, worms and fish

even in 1:1000000 dilution. Their even in 1:1000000 dilution. Their molecule consists of the aglycone molecule consists of the aglycone

called sapogenin and called sapogenin and

carbohydrates (sugars).carbohydrates (sugars).

Page 3: MP  and MPM containing steroidal  saponins

According to the structure of According to the structure of aglycone two kinds of saponins aglycone two kinds of saponins are recognised- the steroidal ( Care recognised- the steroidal ( C2727 commonly tetracyclic commonly tetracyclic triterpenoids - neutral) and the triterpenoids - neutral) and the pentacyclic triterpenoids types pentacyclic triterpenoids types (C(C30, 30, acidic propertiesacidic properties ). Both of ). Both of these have a glycosidal linkage at these have a glycosidal linkage at CC33 and have a common biogenetic and have a common biogenetic origin via mevalonic acid and origin via mevalonic acid and isoprenoid units.isoprenoid units.

Page 4: MP  and MPM containing steroidal  saponins

cyclopentane perhydro phenanthrene

Steroidal saponins

Normal line monodesmoside

Iso-line mono-desmoside

Page 5: MP  and MPM containing steroidal  saponins

Steroidal saponinsSteroidal saponins Steroidal saponins are less widely distributed in nature Steroidal saponins are less widely distributed in nature

than the pentacyclic triterpenoid type. Sapogenins are than the pentacyclic triterpenoid type. Sapogenins are derivatives of cyclopentanperhydropenantrene. Some derivatives of cyclopentanperhydropenantrene. Some species of Strophantus and Digitalis contain both species of Strophantus and Digitalis contain both steroidal saponins and cardiac glycosides.steroidal saponins and cardiac glycosides.

Steroidal saponins are found in plants of such families Steroidal saponins are found in plants of such families as: Liliaceae, Amaryllidaceae, Dioscoreaceae, as: Liliaceae, Amaryllidaceae, Dioscoreaceae, Schrophulariaceae, Zygophyllaceae etc. Schrophulariaceae, Zygophyllaceae etc.

Steroidal saponins are of great pharmaceutical Steroidal saponins are of great pharmaceutical importance because of their relationship to compounds importance because of their relationship to compounds such as the sex hormones, cortisone, diuretic steroids, such as the sex hormones, cortisone, diuretic steroids, vitamin D and the cardiac glycosides. Some are used vitamin D and the cardiac glycosides. Some are used as starting materials for the synthesis of these as starting materials for the synthesis of these compounds.compounds.

Page 6: MP  and MPM containing steroidal  saponins

Triterpenoid saponinsTriterpenoid saponins

In many triterpenoid saponins In many triterpenoid saponins oleanolic acid is sapogenin. They are oleanolic acid is sapogenin. They are abundant in many dicotyledonous abundant in many dicotyledonous families, particularly the families, particularly the Caryophyllaceae, Sapindaceae, Caryophyllaceae, Sapindaceae, Polygalaceae and Sapotaceae, Polygalaceae and Sapotaceae, Ranunculaceae, Papaveraceae, Ranunculaceae, Papaveraceae, Araliaceae, Rubiaceae and Araliaceae, Rubiaceae and Compositeae. Altogether some 70 Compositeae. Altogether some 70 families are involved.families are involved.

Page 7: MP  and MPM containing steroidal  saponins

Triterpenoidal SaponinsTriterpenoidal Saponins1.1. Saponins, whose aglycones are Saponins, whose aglycones are

represented by pentacyclic compounds represented by pentacyclic compounds

α-amyrin

α-amyrin lupeol hopan

Page 8: MP  and MPM containing steroidal  saponins

Saponins may be containing from 1 to 11 monosaccharides and their derivatives. D-glucose, D-galactose, D-xylose, L-rhamnose, D-glucoronic and D-galacturonic acids are the most common. They form linear or branched chains, and may join by means of hydroxyl and carboxyl groups to aglycones in various position.

Page 9: MP  and MPM containing steroidal  saponins

Methods of obtainingMethods of obtaining

For obtaining of saponins from For obtaining of saponins from MPM water or diluted alcohols MPM water or diluted alcohols are used. Aglycones are well are used. Aglycones are well soluble in organic solvents.soluble in organic solvents.

Page 10: MP  and MPM containing steroidal  saponins

Biological actionBiological action

Saponins stimulate secretion of bronchial Saponins stimulate secretion of bronchial glands, enhance cough center and thus glands, enhance cough center and thus are widely used as expectorants. Also they are widely used as expectorants. Also they are used as adaptogenic drugs (ginseng, are used as adaptogenic drugs (ginseng, aralia), regulate water-mineral balance aralia), regulate water-mineral balance (glycyrrhiza), have anti-inflammatory, (glycyrrhiza), have anti-inflammatory, diuretic and laxative properties. Steroidal diuretic and laxative properties. Steroidal saponins are source for production of saponins are source for production of corticosteroids (cortisone hormones) and corticosteroids (cortisone hormones) and in treatment of atherosclerosis. in treatment of atherosclerosis.

Page 11: MP  and MPM containing steroidal  saponins

Dioscoreae rhizomata cum radicibus Dioscoreae rhizomata cum radicibus Wild Yam rhizome with rootWild Yam rhizome with rootDioscorea nipponicaDioscorea nipponicaWild Yam, Makino, China root, Devil’s Wild Yam, Makino, China root, Devil’s BonesBonesDioscoreaceaeDioscoreaceae Constituents. Constituents. An An

acrid resin, steroid acrid resin, steroid saponin dioscin, saponin dioscin, starch, calcium starch, calcium oxalate, etc.oxalate, etc.

Uses. Uses. Represents Represents rich source of the rich source of the principles used as principles used as a cortisone a cortisone precursors.precursors.

Page 12: MP  and MPM containing steroidal  saponins

Folia AgavaeFolia AgavaeAgava Americana- Century plantAgava Americana- Century plantAgavaceaeAgavaceae Constituents. Constituents.

Leaves contain Leaves contain steroidal saponins-steroidal saponins- gecogenin, gecogenin, manogenin, manogenin, gitogenin. gitogenin.

Uses. Uses. Leaves are Leaves are used for the used for the production of production of steroidal hormones.steroidal hormones.

Page 13: MP  and MPM containing steroidal  saponins

Herba Tribuli terrestrisHerba Tribuli terrestrisTribulus terrestris- cathead, caltrop Tribulus terrestris- cathead, caltrop ZygophyllaceaeZygophyllaceae

Constituents. Constituents. Herb contains Herb contains steroidal glycosides (2%) and steroidal glycosides (2%) and dioscine, tihogenin, hecogenin dioscine, tihogenin, hecogenin and gracyllin are among them; and gracyllin are among them; flavonoid glycosides, tannins, flavonoid glycosides, tannins, ascorbic acid.ascorbic acid.

Uses. Uses. Liquid extractLiquid extract has has diuretic, antisclerotic and diuretic, antisclerotic and hypotensive effects, stimulates hypotensive effects, stimulates secretion of gastric juice. secretion of gastric juice. TribusponinTribusponin is used for is used for prevention and treatment of prevention and treatment of atherosclerosis. Drugs also have atherosclerosis. Drugs also have anabolic properties (anabolic properties (tribestantribestan).).

Page 14: MP  and MPM containing steroidal  saponins
Page 15: MP  and MPM containing steroidal  saponins

Foenugraeci semina Foenugraeci semina Fenugreek seedFenugreek seedTrigonella foenum-graecum-Trigonella foenum-graecum-Fenugreek (Greek Hay Seed, Bird’s Foot)Fenugreek (Greek Hay Seed, Bird’s Foot)FabaceaeFabaceae

Constituents. Constituents. Mucilage Mucilage (galactomannan - about 28 (galactomannan - about 28 %.), %.), trigonelline, trigonelline, choline, an choline, an odorous oil and proteins (aboutodorous oil and proteins (about

22 %.), steroid saponin, that have 22 %.), steroid saponin, that have diosgenin as aglicon.diosgenin as aglicon.

Uses. Uses. Main application is for the Main application is for the production of steroidal hormones. production of steroidal hormones. ExtractExtract is part of is part of Phytolysin.Phytolysin. The The ground drug is employed in ground drug is employed in domestic medicine for the domestic medicine for the preparation of poultices,preparation of poultices, enemata, enemata, and plasters; in veterinary cattle and plasters; in veterinary cattle and condition powders.and condition powders.