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Research Article [Kameshwari , 4(2): Feb., 2013] CODEN (USA): IJPLCP ISSN: 0976-7126

INTERNATIONAL JOURNAL OF PHARMACY & LIFE SCIENCES

Chemical constituents of wild onion Urginea indica Kunth Liliaceae M.N. Shiva Kameshwari Department of Botany, Bangalore University, Bangalore, (Karnataka) - India

Abstract Wild Onion Urginea indica provide health promoting phytochemicals, as well as nutrients. Onions are bitter to taste, they contains plenty of raphides in which acts as defensive mechanism. Wild onions are source of Vitamin E, C & K, potassium, dietary fibre & folic acid. They also contain calcium, iron & proteins, several healthy & commercial compounds, such as Bufadienolides, Quercetin, Allose, Mindererus spirit, Tartronic acid & Paraldehyde. These compounds have a variety of health functional properties, including anticancer and antimicrobial activities. They each have been shown to help neutralize the free radicals in the body, & protect the membranes of the body’s cell from damage.

Key-Words: Urginea india, Wild onion, Chemical constituents

Introduction Quercetin: - being strong antioxidant delay or slow the Squill attract moisture from the air, & then becomes oxidative damage to cells & tissue of the body. Studies pliable & spoiled, on account of which squill & well as have indicated that Quercetin helps to eliminate free their powder, should always be kept in well closed radicals in the body, to inhibit low density lipoprotein, vessels. oxidation an important reaction in the artheroselerosis Urginea indica Kunth. commonly called as Indian & coronary disease to protect & regenerate vitamin E-a squill, Scilla indica Roxb. Jesso. True powerful antioxidant. onion, Sea onion. Scilla the classic name of the , is Wild onions contain very little Quercetin, so people derived from a Greek word meaning to exite or disturb stick to cultivated onions which contain 22.40 mg & ; Scilla maritima was the name given by Linnaeus, but 51.82 mg per medium sized onion (100 gram) this was changed to Urginea an allusion to the Algerian Quercetin can withstand the heat of cooking as long as tribe Ben urgin, near Boma, where stein hill, in 1834 it is in low heat. examined this plant, removing its from the In the “Garuda Puran” the Sanskrit word palandu Scilla. But it now retains Scilla as its specific name. which means wild onion has been mentioned and great Urginea indica bulbs is used in Arthritis, rheumatism, sages like Maharshi Atreya & Lord Dhanvantri have tumors, cancer, Edema, gout, Male sterility, Psoriasis, described the use of wild onions in detail. There is also Chronic cough, Swellings, Pulmonary troubles, a description of Kandarpa Varishya Vati, in which Cardiac stimulant, Incutaneous, & subcutaneous onions along with nutmeg, mace, cinnamon, clove & parasitic infection.

cardamom are combined with the seeds of Mucuna Geographical sources Pruriens (Kauncha beeja), taken daily in the morning It is found growing in sandy places, especially, the and at bed time, it is good toner for the body as a seacoast in most of the Mediterranean districts, being whole. abundant in southern Spain, found in Portugal, The juice of the fresh is very acrid & vesicating & Morocco, Algeria, Corsica, Southern France, Italy, much milder by desiccation. The juice irritates the skin Malta, Dalmatia, Greece, Syria, Canary island & the when rubbed into it, & this is due to mechanical effect cape of good hope, India, Africa. viz. to the presence of hard crystals of calcium oxalate, It is often grown under fig trees in the Italian Riviera, sharp pointed at each end. Crystals attain a length of 1 & grown in many botanical gardens, & it is stated millimeter. recorded as cultivated plant in England in 1648 & in

* Corresponding Author oxford botanical gardens. E.mail: [email protected] It is a variable plant, bulb, leaves, differing greatly in size & color, which led to the formation of several Int. J. of Pharm. & Life Sci. (IJPLS), Vol. 4, Issue 2: February: 2013, 2414-2420 2414

Research Article [Kameshwari , 4(2): Feb., 2013] CODEN (USA): IJPLCP ISSN: 0976-7126 species, about twenty five species having been It forms a powerful stimulant of the urinary organs. (A described. Two varieties of squill, termed, white & red pill containing 1 grain each of squill, digitalis & squill identified by druggists. calomel is popularly known as iriemeyer’s pill) The Both varieties are mentioned by pling & other ancient extract of bulb also shows hypoglycaemic & anti writers: the white squill is mentioned in medieval cancer activity. literature, Red squill in the medical school of salerno. It also contains various flavonoids including Quercetin In its home it is frequently used fresh, in other & kaempferol polyglycosides, sinistrin, mucilage & countries, it is directed by pharmacopoeias to dry & calcium oxalate (Ghami, 2003) Fresh squill yields two use it. glycosides Scillaren-A Scillaren-B. Squill also contains When fresh the bulb abounds in a viscid, acrid juice dextrose, starch, albuminous bodies, volatile oil, which causes inflammation in the skin this is because mineral salts. of Raphides action & it shows high medicinal activity. The peculiar active principles of squill have been On drying, there is slight loss of medicinal activity. investigated by many chemists E. Merck by an When kept in a dry place, Squill retains its virtues for a unpublished process; obtained amorphous, brown long time, when powdered unless carefully preserved Scillitoxin insoluble in water & ether soluble in in a dried state its absorbs moisture & forms a hard alcohol, and crystalline yellow scillin, not easily mass & it has to be kept dry over quick lime. soluble in water. The chemical constituents of squill are imperfectly It is a glucosid, yielding upon hydrolysis dextrose known. Merck in 1879 separated the three bitter butyric acid & iso-propyl-alcohol. A glutinous glucosidal substances. Scillitoxin, Scillipcrin & Scillin. carbohydrate (C 6H10 O5) resembling dextrin-exists in The first two are amorphous & act upon the heart, squill in large quantity. It was called sinistrin by Scillin is crystalline & causes numbing & vomiting schmiedeberg (1879). It differes from dextrin in being other constitutes are mucilaginous & saccharine matter, laevo rotatory & upon hydrolysis yielding chiefly a peculiar carbohydrate named Sinistrin , an Inulin like laevulose & other sugars. substance which yields laevulose on being boiled with In large doses, squill is dangerous, it can not be safely dilute acid. The name Sinstrin in 1834 first proposed used in any doses, unless combined with opium. by Macguart for Inulin. In small doses it stimulates all of the secretory organs, Calcium oxalate is also present in bundles of long, relieve irritation of the Mucous surfaces & check acicular crystals which easily penetrate the skin when excessive secretions. It acts better in general & passive the bulbs are handled & cause intense irritation dropsies than in local dropsies & in those of asthemic sometimes eruption, if a piece of fresh squill is rubbed character. Dropsies of cardiac origin are relieved by it. on the skin. it may be used in all cases where no inflammation is The chemistry of squills is not worked out fully. Most present, & there is over action of the kidneys. of the glucosides described have only been prepared in It acts favourably where there is a dry harsh skin, an amorphous condition with uncertain chemical parched tongue, fevered lips & contraction of features. identity. In cardiac dropsy, when the hearts action is feeble & Medicinal uses the pulse is weak & rapid, 2 grains of squill may be Indian squill was valued as a medicine in early classic given in a fluid drachm of infusion of digitalis 3 times times, being official in all pharmacopoeias. Oxymell of a day. As an expectorant it will be found useful in squill, used for coughs was invented by Pythagoras chronic catarrh, humid asthma, pheumonia pthisis, who lived in 6 th century before birth of Christ. winter cough & other chronic bronchial ailments. Theophrastus in 3 rd century mentioned Indian squill, Dose of the powder as a diuretic & expectorant from 1 epimenides, a greek have made much use of it. to 3 grains as an Emetic, 6 to 12 grains of the syrup 1 Homer referred it as sea onion, pling & dioscorides or 2 fluid drachms tincture 1 to 20 drops. was acquainted with it & introduced the method of Wild onion Urginea indica are carminative, melt the making vinegar of squills, compounds of squill with phlegm & oil extracted from them is volatile. honey was administered by Arabian Physicians of the Onions has several medicinal uses described by various middle ages, introduced the drug into European authors as remedy or cure for different ailments. medicine which is still in use. It is largely used for its In rheumatism, asthma, as a deobustrbent, prescribed stimulating expectorant & diuretic properties & is also for dropsy, skin diseases, bronchitis, renal calculi, a cardiac tonic, it has also been given as an emetic in leprosy, scabies, headaches & disease of the nose whooping cough. (bulb) aids in removing any obstructions to secretion or excretion & expectorant, cardiac stimulant Int. J. of Pharm. & Life Sci. (IJPLS), Vol. 4, Issue 2: February: 2013, 2414-2420 2415

Research Article [Kameshwari , 4(2): Feb., 2013] CODEN (USA): IJPLCP ISSN: 0976-7126 emmenagogue (bulb) & cyanogentic (plant) rheumatism) by washing the whole body with a anthelmitic, alexiteric. solution prepared by soaking the finally chopped bulbs Wild Onion compound Quercetin linked to lower blood in water. pressure by an average of five millimeters of mercury, U. epigea known as lukhovu to the swati of Swaziland indicates new research led to significant reductions in who use it as a soap & for treating back ache (Dlamini, the blood pressure high intake of Quercetin & other 1981) to the north west in sekhukhuneland smoke from flavonoids from onion & other food has been shown to the smoldering bulbs of U. epigea is inhaled to relieve decrease risk of artherosclerosis in an epidemiologic headaches (Dyer, 1947). study in the united states. The most abundant anthocyanin found in the squill The chemistry of the squill & its constituents have been varieties examined, was cyanidine 3-monoglucoside, reviewed by Stoll (1937) & by Fieser & Fieser (1959). Tetraploids were found to contain Pelargonidin Earlier pharmacologists divided the components of glycoside. squill into scillaren A & Scillaren B. Scillaren A is Among the bulbs not exposed to light, the greatest composed of an aglycone rhamnose & glucose. content of anthocyanins was present in the tetraploids. Scillaren has a double bond in the glycone. Removal The hexaploids contained no appreciable anthocyanins. of the rhamnose & glucose from scillaren A produces Anthocyanins did not appear on the leaves in the aglycones. Scillaren B is a mixture of cardiac appreciable quantities, except in the grown in the glycosides was more effective in its diuretic & darkness, coinciding with the decrease in chlorophyll natriuretic action than digoxin. content. The sap of leaves & bulbs of Urginea species are Squill has been used from a very early period. The irritating to the skin ; some species produce such ancient Greek physicians prescribed it with vinegar & marked topical stinging & itching effects that they are honey almost in the same manner as it is used at used by young xhosa boys during pain – Eudurance present. The composition of the drug, first efficiently games, indicating the presence of bufadienolides. studied by Merck in 1878, is very complex. The chief Bufadienolides containing plants are used as constituent is Scillitoxin, bitter and intensely substance anthelmintics , for bronchial asthma, heart conditions, Scilliplain is also physiologically active. The bulb fevers & during pregnancy (Hutchings & Terblanche, contains plenty of Mucilage & a considerable quantity 1989). of an irritant resin. Ethnomedicinal plant traders in nelspruit sell U. Thirteen bufadienolides were isolated by means of lydenburgenesis under the name masi xabane & FAB-MS-H-NMR & 13C-NMR studies by Krenn et al isiklenama. Glycosides are usually compounds of plant 1987. The compounds were structurally elucidated as origin, they are made up of one or more sugars 1) Scillarenin combined with an alcohol, or a complex molecule such 2) Scilliphaeosidin as a steroid nucleus. Since these compounds occur in nature combined with 3) Scillarenin -3-O-a-L-rhamnoside various sugars they have been given the general term of 4) Scilliphaeosidin-3-o-a-L-rhamnoside cardiac glycosides. Lyon & Degraff (1967) estimate that more than 400 cardiac glycosides have been found 5) Gamabufotalin-3-o-d-L-rhamnoside in nature. It is of interest to speculate that in these 6) 11a-hydroxyscilliglaucosidin-3-o-a-L- many cardiac glycosides there may be one or more that are superior to digitalis. rhamnoside It is the purpose of the present review to focus attention 7) Scillarenin 3-o-a-L-21, 3 1-diacetyl- on one of these cardiac glycosides – squill & its chemical constituents. rhamnoside-41-β-D-glucoside There is very little clinical use of squill & its 1 β constituents in this country, although these preparations 8) Scillarenin -3-o-a-L-rhamnosido-4 - -D- are used abroad. The last description of the drug in the glucosido-311 -β-D-glucoside U.S. Pharmacopiea appeared in 1972 ; in the National 1 1 Formulary in 1960. New & Non official remedies 1952 9) Scillarenin-3-o-a-L-2 , 3 -diacetyl contains description of Scillaren, Scillaren A & B 1 and rhamnosideo-41-β-D-glucosido-311 -β-D- Urginin for internal use in treating asthma & itching of skin. A swazi traditional medical practitioner from glucoside nelspruit reportedly alleviated “body pains’ (possibly Int. J. of Pharm. & Life Sci. (IJPLS), Vol. 4, Issue 2: February: 2013, 2414-2420 2416

Research Article [Kameshwari , 4(2): Feb., 2013] CODEN (USA): IJPLCP ISSN: 0976-7126 1 1 10) Scillarenin-3-o-a-L-2 -3 -diacetyl (g) rhamnosido-41-β-D-glucosido-411 -β-D- Energy (K 301.32 - Cal) Kca/100 gm glucoside. Calcium 11) Scillarenin-3-o-a-L-21, 3 1-diacetyl 300.0 0.99%/80 mg (mg) 1 β 11 β rhamnosido-4 - -D-glucosido-4 - -D- Phosphorus 290.0 0.13% glucoside. (mg) 12) Scilliphaeosidin-3-o-a-L-rhamnosido-41-β-D- Iron (mg) 2.0 230 mg Carotene glucosido-311 -β-D-glucoside. - - (mg) 1 β 13) Scilliphaeosidin-3-o-d-L-rhamnosido-4 - -D- Vitamin C 147.0 - glucosido-411 -β1-D-glucoside (mg) Magnesium 0.12% / 22 Quantification of Bufadienolides in different cytotypes - (mg) mg of U. indica in both roots & bulbs were made by Sumitha Jha & Sen (1983). Sodium (mg) 40.0 65 mg Kopp et al 1996 isolated forty one bufadienolides from Potassium 1000 120 mg the bulbs of U. maritima from Egypt. Phytosterols identified in roots, bulbs & leaves of Copper (mg) - 0.16 mg diploid, triploid, tetraploid and hexaploid cytotypes of Manganese - 0.14 mg U. indica by gas liquid chromatography, such as (mg) stigmasterol, campesterol & sitosterol, Sumitha Jha and Molybdenum Sumitha Sen (1981). - - Isolation and Characterization of a 29KDa glycoprotein (mg) with antifungal activitiy from bulbs of urginea indica Zinc (mg) - 0.38 mg (Sandhya Shenoy et al 2006) and also anti-angiogenic Fibre content 6.4 12.30% and proapoptotic activitiy a novel glycoprotein from Calorific u.indica is mediated by NF-KB and caspase activated - 3503 cal / gm Dorase in ascites tumos model by Deepak et al 2003. value Acid value - 7.23 A detailed review on bio-systematics studies of Medicinal plant urginea indica has been made by Total ash - 6.61% Shiva Kameshwari Et al (2012). Ph (5% - 4.68 The Chemical composition of onion (Edible) is solution) compared with wild onion & given as under Mineral Contents in U. indica Nutritive value per 100 gm of onion Edible Silica 290 mg Non Edible (dehydrated) (dehydrated) Alumina 585 mg Particulars onion wild onion Iron 230 mg cultivated (%) (%) Calcium 80 mg Moisture 4.6 6.16% Magnesium 22 mg Protein (g) Sodium 65 mg (kjelda) 10.6 8.36% Potassium 120 mg Total protein Copper 0.16 mg Fat g 0.8 0.32% Manganese 0.14 mg Minerals (g) 3.5 - Zinc 0.38 mg Carbohydrate 74.1 66.25%

Int. J. of Pharm. & Life Sci. (IJPLS), Vol. 4, Issue 2: February: 2013, 2414-2420 2417

Research Article [Kameshwari , 4(2): Feb., 2013] CODEN (USA): IJPLCP ISSN: 0976-7126

Therapeutic uses furfurss ole Pentanoic acid, 4- Roots acid 1. Skin disorders. oxomethyl ester or 62.76% hydrolysed 2. Anti-inflammatory methyl levulinate 3. Worm infestation 2-Butanone, 3-Hydroxy or Acetoin 20.5% 4. Diaorrhea Volatile oil of 2.3-Butanediol (R –

bulbs (R,R)) - & Butane -2.3- 5. Ascites 25.4% diol or 2.3 –Dihydroxy 6. Cardiac disorders butane 7. Reduce inflammation, in cardiac disorders. Ammonium acetate ss 8. Chronic rhinitis Acetic acid, ammonium salts mindereru’s spirits Volatile oil of 9. Chronic cough (Dried slices) Acetic acid 47.23% roots 10. Chronic pulmonary disorders Ethylic Acid Methane Carboxylic acid, 11. Respiratory diseases Vinegar acid 12. Makes heart stronger Pentanoic acid, 4-oxy Acid methyl ester or Levulinic 32.01% 13. Renal failure hydrolysed acid, Methyl Ester 14. Chronic renal failure leaves (Gorur) D-Allose & Beta-D 34.09% Allose or Hexose 15. Amenorrhea Acid Pentanoic acid, 4-oxy 16. Dysmenorrhoea Hydrolysed methyl ester or 33.83% 17. Itching leaves Levulinate, Levulinic (shimoga) acid 18. Useful in cancer Pharmacology Formulations 1. It suppresses vatta, Kapha & pitta Used as syrup & tincture. 2. Used in worm infestation Dosage Choorna (powder) 3. Cardiac tonic 100 to 200 Milligrams 4. Anti inflammatory Panak – 30 to 60 drops 5. Cough expectorant Surasatav – 5 to 30 drops 6. Diuretic Ayurvedic Properties 7. Seductive 1. Guna (Properties) – Tikshan, Laghu 8. Anti-carcinogenic 2. Rasa (Taste) – Katu, Tikt Toxicology 3. Vipak (Metabolisum) – Katu The toxicity of squills has recently been ascribed to a 4. Virya (Potency) ushan single, bitter, non-nitrogenous glucoside, to which the 5. Prabhav (Impact) Hridya name scillitinis given causes vomiting & diaorrhea GC MS analysis in Urginea indica : [Petroleum when taken orally. Ether Extract] Active ingredients & its chemistry Parts used in Compound with highest % Area Name of the compound Formula Plant peak Sitosterol C29 H50 O 2 – Furancarboxaldehyde, 5- Stigmasterol C29 H48 O hydroxymethyl –ss 2- Campeterol C H O Bulbs Acid 28 48 Furaldehyde, 5- 28.88% hydrolysed Octacosanoic acid C28 H56 O2 Hydroxyethyl –ss 5- Hydroxy methyl furfural, Scillarenin C24 H32 O4 ss hydroxyl methyl 5-6-dimethyoxy – 3-4- C30 H36 O17 Int. J. of Pharm. & Life Sci. (IJPLS), Vol. 4, Issue 2: February: 2013, 2414-2420 2418

Research Article [Kameshwari , 4(2): Feb., 2013] CODEN (USA): IJPLCP ISSN: 0976-7126 dioxymethylene- 7-0- (6" - β- References D-glucopyranosyl - β-D- 1. Anthony J. Verbiscar, Jagjivanbhai Patel, glucopyranosyl) flavanone) Thomas F. Banigan and Robert A. Schatz. 1986. Scilliroside and other Scilla Compounds in Red 5-4-dihydroxy-3-0-x-L- squill. J. Agri. Food Chemistry. Vol. 34: No: 6. rhamnopyranosyl 2. Bentley and Trimen, Med. Plants 281. -6-glucopyranosyl -7-o- (6- C42 H46 O22 3. Benkeblia, N. 2004. Antimicrobial activity of para-coumaroyl-β-D- essential oil extracts of various onions Allium glucopyranosyl) cepa & Garlic (Allicea satium) lebeusmwiss-u- 5.4-dihydroxy-3-o-(2-β- Technol. 373. glucopyranosyl-x-L- 4. Chemical constituents of cultivated onion rhamnopy ranosyl) -6-C- Allium cepa Liliaceae. C H O glucopyranosyl-7-o-(6-para- 42 56 27 5. Deepak, A.V. Thippeswamy, G., Shiva coumaroyl-β-D- Kameshwari, M.N. and Salimath, B.P. 2003. glucopyranosyl) Isolation and Characterization of 29KDa glycoprotein with antifugal activity from bulbs Scillaren A C12 H21 O9 of Urginea indica. Biochemical and Biophysical Scillicyanosidin research communications, 311. 735-742. 6. Deepak, A.V. and Salimath, B.P. 2006. Hydenburgenin Antiangiogenic and Proapoptotic activity of a Bufadienolides - 6β-acetoxy- novel glycoprotein from U. indica is mediated 3β, 8 β, 14 β, trihydroxy -12- by NF-KB and Caspase activated Dorase in oxobufa-4, 20, 22- trizenolide ascites tumor model Biochemic, 88, 297-307. β 7. Dlamini, B. 1981. Swaziland flora. Their local Bufadienoldes-14 - names and uses, ministry of agriculture and co- hydroxybufa-3.5, 20, 22- operatives. Mbabane, Swaziland. tetraenolide 8. Dyer, R.A., 1947. Urginea epigea. The Bufadienolides – Riparianin flowering plants of South Africa, 26: t.1027. Purified petroleum ether extract is subjected to HPLC 9. Dictionary of Natural Products (DNP) on CD- & highest peak has been obtained at a retention time Rom. 2003. Chapman and Hall Electronic 15.05. Publishing divisions, London, version. 12:1. 10. Edward, C. Arnold, Neperville, Patrick J. Silady, Niles, United States Patent: 5, 620, 960. 11. Fieser, L.F., and Fieser, M., 1959. Steroids, New York Reinhold. 782. 12. Free dictionary.com. 13. Grieve, Squill A modern herbal. Botanical.com Home page. 14. Ghani, A. 2003. Medicinal Plants of Bangladesh with Chemical constituents and uses 2nd Edi: 423 Dehaka. Asiatic society of Bangaladesh. 15. Herbs 2000.com. 16. Hutchings, A., Terblanche, S.E. 1989. Observations on the use of some known and suspected toxic Lilliflorae in Zulu and Xhosa medicine, South African medical Journal 75: 62- 69. 17. Homer in the Odyssey (Book X). Oxymel of Squill. 18. Kopp, B., Krenn, L., Draxler, M., Hoyer, A., Terkola, R., Vallaster, P., Robein, W. 1996. Bufadienolides from Urginea maritima from Egypt. Phytochemistry. 42:513-522. Int. J. of Pharm. & Life Sci. (IJPLS), Vol. 4, Issue 2: February: 2013, 2414-2420 2419

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