Glycosides Pt. 2 PDF

PCOG | GLYCOSIDES PT. 2 LECTURE | SIR ABEL AMATONG 3 SAPONIN GLYCOSIDES Foams upon shaking Steroidal in natre (CPPP) Sternutatory Aglycone portion: Sapogenin...

PCOG | GLYCOSIDES PT. 2 LECTURE | SIR ABEL AMATONG 3 SAPONIN GLYCOSIDES Foams upon shaking Steroidal in natre (CPPP) Sternutatory Aglycone portion: Sapogenin Origin Active Constituent Uses Dioscorea Species species of Dioscorea botogenin - rich sources of cortisone precursors; Tubers of many of the dioscoreas (yams) diosgenin - D. floribunda - considered by U.S. Department of Agriculture as Various species of Dioscorea known as Mexican yams (obtained from the root of Dioscorea spiculiflora) the best source of steroids Sisal Agave sisalana hecogenin ○ (obtained commercially as the acetate in about 0.01% yield from sisal leaves) Sarsaparilla Root Species of Smilax smilagenin - diosgenin Former uses: Vera Cruz - S. aristochiaefolia sarsasapogenin - yamogenin ○ Tx of syphillis Brown - S regelii ○ rheumatism Guayaquil - S febrifuga ○ certain skin diseases Costa rica/Jamaican BHP (1960) ○ Tx of psoriasis and eczema ○ rheumatism ○ rheumatoid arthritis Sarsaparilla - widely used as a vehicle ○ Large quantities is employed in the manufacture of non-alcoholic drinks Black Cohosh, Cimicifuga BHP 1983 Aceta racemosa Triterpenoid saponins, treatment of menopausal and other female disorders Cimicifuga racemosa ○ e.g., actein various rheumatic conditions; (fam: Ranunculaceae) endocrine activity; noted hepatotoxicity in the 1990s Butcher’s Broom Ruscus aculeatus The BP/EP drug consists of the dried, whole or broken roots and alcoholic extract of the roots Plant family: Liliaceae rhizomes of the plant. ○ anti-inflammatory activity ruscogenin ( 1ßhydroxydiosgenin) ○ produce diminished capillary permeability ○ exert a vasoconstrictor effect in the peripheral blood vessels Siberian Ginseng (BP, EP/BHP) Eleutherococcus senticosus (Araliaceae) consists of the dried, whole or cut organs of Eleutherococcus Chinese medicine: senticosus (Acanthopanax senticosus) ○ treatment of rheumatoid complaints minimum content of 0.8% for the sum of: former USSR countries: adaptogen ○ eleutheroside B Europe: ○ eleutheroside E ○ tonic in states of fatigue Ginseng Panax ginseng [Asian Ginseng] (Araliaceae) Roots ○ White ginseng- products of: American Ginseng - panax quinquefolius sun drying of the root after removal of the outer layers ○ Red ginseng - products of: steaming the root followed by artificial drying then sun drying Liquorice Root Glycyrrhiza glabra and/or G. inflata and/or G. uralensis Liquorice owes most of its sweet taste to glycyrrhizin flavouring agent dried unpeeled or peeled, whole or cut root ○ (50x sweeter) demulcent and The Spanish and Italian drugs are derived from the ○ potassium and calcium salts of glycyrrhizinic mild expectorant. variety typica of G. glabra acid Glycyrrhetinic acid/Glycyrrhetic acid ○ for hypertension roots: |1  ○ 5-15% of sugars (glucose, sucrose); ○ about 1-2% of asparagine ○ 0.04-0.06% volatile compounds Primula Root Primula veris (COWSlip) BHM: traditionally used the leaves, flowers and roots of expectorant for the treatment of bronchial conditions P. elatior (OXlip) P. vulgaris (common primrose) dried rhizome and root triterpenoid saponins 5-10% Plant family: Primulaceae Quillaia Bark Quillaja saponaria (Rosaceae) quillaic acid emulsifying agent also known as: gypsogenin ○ Soap Bark, Quillaia contains about 10% of saponins ○ Panama Wood, ○ Quillaia Senega Root Polygala senega (Polygalaceae) triterpenoid saponins (6-12%); stimulant expectorant in chronic bronchitis dried root crown and root aglycone: bayogenin; P. tenuifolia is used in China and Japan as an cultivated in Japan: P. japonica and P. fallax expectorant, tonic and sedative ○ P. senega var. latifolia ○ contain polygalasaponins European Goldenrod Solidago virgaurea (Polygalaceae) used principally in traditional medicine for the treatment European Goldenrod BP/EP, Goldenrod BHP 1996 of whole or cut, dried flowering aerial parts ○ urinary tract infections ○ catarrh ○ whooping cough ○ externally for the treatment of insect bites, wounds, etc. Golden Rod BP/EP Solidago gigantea, S. canadensis/S. altissima European phytotherapy for much the same purposes as: whole or cut, dried, flowering parts ○ European goldenrod urolithiasis ○ cystitis ○ rheumatism ○ antiphlogistic Saikosaponins Bupleurum falcatum (Umbelliferae) Chinese medicine: roots ○ Tx of hepatobiliary disorders ○ Anti-inflammatory Horse Chestnut Seed Aesculus hippocastanum (Hippocastanaceae) Aescin - up to 20% in the dried seeds Extracts Seeds and the tree Traditionally employed for the treatment of peripheral vascular disorders including ○ Haemorrhoids ○ varicose veins ○ leg ulcers and bruises Centella Centella asiatica (family Umbelliferae) syn. Hydrocotyle asiaticoside BHP (1983): asiatica Other triterpenoid saponins: mild diuretic Indian pennywort ○ brahmoside anti-rheumatic gotu kola ○ brahminoside dermatological agent and peripheral vasodilator Indian water navelwort ○ centelloside topically as vulnerary. tiger grass ○ medecasside As such, it is used for rheumatic conditions skin tonic in wound healing. ○ Employed for indolent wounds it is also included in medicinal creams and some cosmetic preparations. Ivy Hedera helix (family Araliaceae) hederagenin Ivyleaf extracts - whole or cut aerial leaves bayogenin traditionally used as an expectorant for the treatment of oleanolic acid various chest conditions, such as: ○ bronchitis ○ whooping cough; ○ also for gout and rheumatic pains SAMMAN | 2  most saponins are toxic in excess causing: ○ diarrhea ○ vomiting ○ allergy 4 CYANOGENIC GLYCOSIDES Sources: 1830: ○ manihotoxin - Manihot utilissima (cassava) ○ amygdalin - bitter almonds ○ linamarin - linseed ○ phaseolunatin - Phaseolus lunatus (bean) Glycoside Source Family Amygdalin Prunus amygdalus Rosaceae Linamarin Linum usitatissimum Linaceae Prulaurasin Prunus laurocerasus Rosaceae Manihotoxin Manihot utilissima Euphorbiaceae Dhurrin Sorghum vulgare Gramineae Sambunigrin Sambucus nigra Caprifoliaceae Vicianin Vicia angustifolia Leguminosae Phaseolunatin Phaseolus lunatus Leguminosae Prunasin Prunus serotina Rosaceae Origin AC Uses Wild Cherry Bark dried bark of Bark contains prunasin and the enzyme prunase Syrups and Tinctures: 1. Prunus serotina (Rosaceae) Mainly used in cough preparations for irritable and Wild Black Cherry or Virginia Prune Bark; Prunus serotina amygdalin in the leaves of several Prunus spp., persistent coughs P serotina cultivar of P virginiana Cherry-laurel leaves Prunus laurocerasus (Rosaceae) when crushed Odor of benzaldehyde is evident cyanide content of small young leaves are reported rapidly dropping to about 0.4-1.0% as leaf size increase SAMMAN | 3  5 ISOTHIOCYANATE GLYCOSIDES Aka Glucosinolates or Mustard glycosides Examples: ○ sinigrin from black mustard ○ sinalbin from white mustard ○ gluconapin from rapeseed Origin AC Uses Black or Mustard dried, ripe seeds of Brassica nigra or B. juncea and their Principal constituent: Local irritant synonym: Sinapis nigra varieties sinigrin (potassium myronate) → allyl isothiocyanate emetic rubefacient vesicant White Mustard dried, ripe seeds of Brassica alba Principal constituent: Commercial use: condiments Synonym: Sinapis alba Sinalbin → acrinyl isothiocyanate ○ EXAMPLE: When hydrolyzed by the enzymes myrosin, they yield mustard oils B nigra - cultivated in England B junica - India Black Mustard White mustard Contains 30-35% volatile oils Contains 20-25% Fixed oils Crushed or powdered seed + water less volatile than allyl isothiocyante ○ _ → myrosin (hydrolysis of singrin) Sinalbin → acrinylisothiocyanate (para-hydroxybenzyl isothiocyanate) ○ Sinigrin (Glycoside) + Myrosin → Allyl isothiocyanate (Mustard oil) + Pot. Acid SO4 + Glucose acrinylisothiocyanate ○ pungent tasting, odorless) 6 FLAVONOL GLYCOSIDES Aglycone portion: flavonoid ○ Yellow pigments - rutin and quercetin ○ Citrus bioflavonoids - hesperidin, hesperitin, diosmin, naringen ○ Vitamin P (Permeability factor) - Rutin and Hesperidin Sources: ○ Elm (Ulmus spp.) - quercetin ○ Buckwheat plant (Fagopyrum esculentum) - Rutin ○ Milk thistle (Silybium marianum) - Silymarin (hepatoprotectant) ○ Ginkgo (G. biloba) - ginkgolides and bilolabides Origin AC Uses Agnus Castus Fruit BP/EP, BHP whole, ripe, dried fruit of Vitex agnus castus BP specifies a minimum content of 0.08% calculated as Synonyms: family Verbenacee casticin ○ Chaste tree Allied drug: Vitex negundo ○ Chaste berry ○ Monk's pepper Birch Leaf dried whole or broken leaves of not less than 1.5% of flavonoids calculated as hyperoside Birch bark - tx of skin diseases ○ Betula pendula (silver birch), and/or Preparations of the leaf: ○ B. pubescens (downy or white birch), and ○ irrigant of the urinary tract hybrids, ○ antirheumatic family Betulacea ○ astringent (in mouthwash) Calendula Flower EP and BP specify the whole or cut, dried, and fully flavonoid mixture involves quercetin internal: Derived from the opened flowers ○ alleviation of gastrointestinal disorders ○ marigold Calendula officinalis Calendula officinalis (Compositae) external: ○ fam. Compositae ○ ointment or lotion for the treatment of minor wounds and rashes Elder Flower dried flowers of Sambucus nigra Flavonoids (up to 3.0%) infusion or herbal tea Allied spp.: Sambucus ebulus (danewort) ○ rutin (main) ○ treatment of feverish conditions ○ small amounts of hyperoside ○ quercetin SAMMAN | 4 Horsetail dried sterile aerial parts of horsetail to the extent of 1.0%, the BP/EP requiring a Equisetum BHP 1996 ○ Equisetum arvense (common horsetail) content of at least 0.3% total flavonoids expressed as Horsetail BP/EP isoquercitroside. Java Tea BP/EP, BHP dried leaves and tops of stems of Flavonoids as represented by sinensetin Traditional uses: ○ Orthosiphon stamineus BP/EP requires a minimum content of 0.05% sinensetin ○ diuretic - treatment of urinary and kidney problems; ○ in S.E. Asia. It is used for the treatment of diabetes and hypertension. Lime Flower BP/EP dried inflorescences of The flavonoid constituents comprise treatment of catarrh and indigestion ○ Tilia cordata (small-leaved lime) ○ quercetin glycosides alleviation of headaches ○ T. platyphyllos (broad-leaved lime) (rutin, hyperoside, quercitrin, etc.) ○ kaempferol glycosides (tiliroside, astragalin). Motherwort BP/EP dried aerial parts of The BP/EP requires a minimum flavonoid content for the Leonurus BHP 1983 (Lion’s Tail) ○ Leonurus cardiaca drug of 0.2% expressed as hyperoside uterotonic family: Labiatae/Lamiaceae ○ for cardiovascular disorders Olive Leaves Olea europea Rutin and oleuropein are the principal components. Infusion for their tranquilising effect in nervous tension and for their antiseptic, astringent and febrifuge properties Passiflora dried aerial parts of The BP drug is required to contain not less than 1.5% Sedative actions Passion Flower ○ Passiflora incarnata total flavonoids calculated as vitexin Spiny Restharrow Root dried roots of roots are traditionally used for their ○ Ononis spinosa L., ○ diuretic family: Leguminosae/Papilio-naceae ○ antilithic ○ anti-inflammatory properties in the treatment of infections of the urinary tract and in removal of kidney and bladder stones. Buckwheat Herb dried aerial parts of Rutin - BP/EP requires a minimum content of 4.0% treatment of various circulatory disorders, including ○ Fagopyrum esculentum ○ varicose veins ○ chilblains ○ retinal bleeding Flavolignans extracts of plants like Silybin treatment of liver ailments ○ Silybum marianum / Carduus marianus silymarin Visnaga dried ripe fruits of Khellin It has been employed in the treatment of angina pectoris ○ Ammi visnaga (Umbelliferae) ○ potent coronary vaso-dilator. and bronchial asthma 7 ALCOHOL GLYCOSIDES Origin AC Uses Willow Bark Various species of Salix which include BP requires the dried drug to contain a minimum of 1.5% anti-inflammatory in the treatment of ○ S. purpurea L., (purple willow) total salicylic acid derivatives, calculated as salicin. rheumatism ○ S. daphnoides, The glycoside, populin (benzoyl salicin), is also arthritis ○ S. fragilis L. (crack willow) associated with salicin in the barks of the Salicaceae. muscular pains. ○ Poplar bark, Populus spp. SAMMAN | 5  8 ALDEHYDE GLYCOSIDES Origin AC Uses Vanilla/Vanilla Pods Vanilla fragrans /V. planifolia - Mexican or Bourbon Green vanilla contains glycosides, namely vanilla) ○ glucovanillin (vanilloside) V. tahitensis (Tahiti vanilla) ○ glucovanillic alcohol. fruits of other species, such as V. pompona (West Indian vanilla), are also used but to a Glucovanillic alcohol much more limited extent yields on hydrolysis glucose and vanillic alcohol; the latter compound is then by oxidation converted into vanillic aldehyde (vanillin). Glucovanillin yields on hydrolysis glucose and vanillin Vanilla Vanilla planifolia Vanillin Semi-synthesized from: Mexican or Vera Cruz Vanilla synthetically from other sources: ○ best-grade ○ (1) coniferin glycoside present in the cambium Bourbon Vanilla sap of pine trees; ○ blacker, with coumarin odor ○ (2) eugenol, a phenol present in clove oil; Tahiti and Hawaii Vanilla ○ (3) lignin, a by-product of the pulp industry. ○ red-brown, unpleasant odor, less suitable for Most of the vanillin in commerce is made from lignin. flavoring Green Vanilla (inactive form) ○ composed of glucovanillin (avenein) and glucovanillic alcohol, when hydrolyzed yields vanillin 9 PHENOL GLYCOSIDES Origin AC Uses Uva ursi or Bearberry dried leaf of The pharmacopoeial drug is required to contain at least mild diuretic (present in teas) and astringent ○ Arctostaphylos uva-ursi and its varieties 7.0% of as arbutin/ursin during excretion it exerts an antiseptic action on the coactylis or adenotricha urinary tract Poison Ivy and Oak Ivy - Rhus radicans Uroshiol Oak - R. toxicodendron 10 LACTONE GLYCOSIDES Origin AC Uses Coumarin Tonka beans (Dipteryx odorata) bishydroxycoumarin/dicoumarol Anticoagulant, precursor of Warfarin Fragrant odor Sweet vernal grass (Anthoxanthum odoratum) bitter aromatic and burning taste Sweet clover (Melilotus albus, M. officinalis) Sweet-scented bedstraw (Galium triflorum) Red clover (Trifolium pratense) Cantharides Cantharis vesicatoria - mature insects with green Cantharidin Preparation: insects are killed with fumes of hot vinegar, metallic luster NH3 or CHC13 Uses: ○ Irritant ○ Vesicant ○ Aphrodisiac ○ Wart-removal Psoralens Ammi majus (Bishop's flower) Methoxsalen/Xanthotoxin/8-methoxypsoralen - Photosensitizing furocoumarins repigmentation in vitiligo Trioxsalen - synthetic furocoumarin SAMMAN | 6