Title of Invention

A process for the production of novel phyto-codysteroid.

Abstract

The invention relates to a process for the production of phytoecdysteroid designated as arunathalsterone, chemical name 2,3,8,20,21 hydroxy- cholest - 7-en-6-one. The compound is used in agroindustry, pharmaceutical industry. The process steps comprises of a) extracting the parts of the plants of Taxus baccata or Taxus var. Wallichiana with polar organic solvent, b) concentrating the extract by vaccum distallation to get residue, c) defatting the residue with non polar solvents, extracting defatted residue with chloroform and purifying the extract by conventional repeated chromatographic methods.

Full Text

This invention relates to process for the production of a novel phytoecdysteroids. This invention also relates to novel phyto-ecdysteroids. The present invention particularly relates to a process for the production of phytoecdysteroid designated as arunachalsterone, chemical name: 2,3,9,20,21 - pentahydroxy-cholest-7-en-6-one and its derivative formula 1 wherein R is OCH3. The novel phytoecdysteoids may be used in agroindustry and pharmaceutical industry. As the species Taxus baccata or Taxus baccata var.wallichiana, due to its occurrence in any other place except India and that to in the specific area of Assam, Manipur, Meghalaya, Nagaland and Arunachal Pradesh, was not chemically investigated earlier, no research work has been done to find out the presence of the arunachalsterone, chemical name: 2,3,9,20,2l-pentahydroxy-cholest-7-en-6-one of the formula 1. We have been working in the field of identifying and producing valuable compounds from naturally occurring plants in and around the state of Assam. During our continued effort in this direction we could identify the species of the plant Taxus baccata or Taxus baccata var.vallichiana from teh North eastern part of India and concentrated our research work to isolate the active ingradients from the parts of the plants Taxus baccata or Taxus baccata var.vallichiana. Accordingly we could observe and isolate a new phytoecdysteroid type compound designated as arunachalsterone, chemical name: 2,3,9,20,21-pentahydroxy-cholest-7-en-6-one with the formula 1 in this species viz. T. baccata or T. baccata var.vallichiana. In addition to this, we have developed an economical and environmentally friendly method for the isolation of the above said compound having formula 1 avoiding toxic chemical like benzene. The main object of the present invention is to provide novel phyto-ecdysteroid of formula 1 wherein R is H or or COCH3. Another object of the present invention, therefore, is to provide a process for the production of novel phytoecdysteroid, chemical name: 2,3,9,20,21-pentahydroxy-cholest-7-en-6-one of the formula 1 and its acetate derivative. Accordingly the present invention provides novel phyto-ecdysteriods of formula 1 wherein R is H or or COCH3. Accordingly the present invention provides a process for the production of phytoecdysteriods of formula 1, wherein R is H or COCH3. which comprises: (Formula Removed) Formula 1 a)extracting the parts such as herein described of the plants Taxus baccata or Taxus baccata var.wallichiana with a polar organic solvent such as herein described, b) concentrating the extract by distilling at reduced pressure at a temperature range of 40-50°C to give residue, c) defatting the above said residue by washing with non polar solvents such as herein described, extracting the defatted residue with chloroform, concentrating the chloroform extract by known methods such as herein described and purifying by conventional repeated chromatographic methods as herein described to give 2,3,9,20,21 -pentahydroxy-cholest-7-en-6-one of formula 1 wherein R is H, d) converting pentahydroxy compound to acetate derivative of formula 1 wherein R is COCH3 by conventional acetylation methods such as herein described. The present invention rovides a process for the isolation of new comound, a phytoecdysteroid designated as arunachalsterone, chemical name: 2,3,9,20,2 l-pentahydroxy-cholest-7-en-6-one of the formula 1 wherein R is H or COCH3 comprises: (a) Extracting the parts of the plants Taxus baccata or Taxus baccata var. wallichiana with an polar organic solvent such as Chloroform, methanol etc. (b) Concentrating the extract by distilling at reduced pressure, (c) Repeated choromatography over silica gel using acetone and chloroform as eluant. (d) Characterization of the compound by IR, NMR, EIMS, (+) FAB MS, of the compound of the structure 1, The plant materials of Taxus baccata or Taxus baccata var. wallichiana used may be preferably leaves of barks. The organic solvent used for the extraction may be any polar protic solvents preferably alcoholic solvents such as methanol, ethanol and the like or polyhalogenated polar solvent such as chloroform and the like. The solvent extract may be concentrated by distilling under vacuum at a temperature in the range of 40-50°C. Plant or animal Kingdoms are the source of many physiologically important secondary metabolites, many of which are used as life saving drugs. As part of our continued effort to investigate bountiful flora of Sub-Himalayan region of North East India, we have isolated an unusual secondery metabolites of the structure 1 from the leaves of a tropical plant, T. baccata or T. baccata var.wallichiana. The structure of this compound has been established on the basis of (+) Fast Atom bombardment mass spectroscopy, 'H-1H COSY45, 1H-13C COSY, DEPT and ROESY NMR spectroscopy. The plant is widely used in Indian Ayurvedic [Kapoor, L.D. in Handbook of Ayurvedic system of medicinal Plants, 1990, p 317, CRC Press Inc. Boca Raton FL.] and Unani system [Vohra, S.B. and Kumar, I. Planta Medica, 1971, 20, 100.] of medicines. The plant was used in this region as timber. The young shoots of the plant is also known to be used by the local people as the treatment of headache, giddiness, feeble and falling pulse, diarrhoea, severe biliousness, spasm, hysteria, epilepsy, nervousness and calculas complaint [Vohra, S.B. and Kumar, I. Planta Medica, 1971, 20, 100; Kirtikar, K.R. and Basu,B.D. Indian Medicinal Plants, Vol III, 2nd Ed., p2383, Lalit Mohan Basu, 49, Leader road, Allahabad, India, 1933.]. The non poisonous and fleshy aril is eaten by the tribals and is credited with expectorant, carminative and stomachic properties. Extracts of J. baccata or T. baccata var.wallichiana is also known to be used in hair-lotions, shaving creams and dentrifecing agents and the decoction of leaves are used as an abortifacient [The Wealth of India, Raw Materials, Vol. X, p132; Publication and Information Directorate, CSIR, New Delhi]. The phytoecdysteroids were found to have properties like antidiabetic, anti-hypercholesterolaemic, antihyperlipidaemic, anti-atherosclerotic [ Camp, F. Plant Ecdysteroids and their interaction with insects in Chapter 14 of Ecological Chemistry and Biochemistry of Plant Terpenoids; ed. Harbourne, J.B. and Tomas Barberan F.A.; Clarendon Press; Oxford; 1991, pp331-376.] and anti-ulcer activities [ Khim. Farm. Zh. 1989, 23(4), 441-445] STRUCTURE OF ARUNACHALSTERONE (CHEMICAL NAME: 2,3,9,20,21- PENTAHYDROXY-CHOLEST-7-EN-6-ONE) The concentrated methanolic extract of air dried and powdered, previously defatted plant material of Himalayan yew (Taxus baccata or Taxus baccata var.wallichiana) collected from Arunachal Pradesh (June, 1994) on repeated gradient flash chromatography (or column chromatography or Medium Pressure Liquid Chromatography or High Pressure Liquid Chromatography or thin layer chromatography) with hexane-ethyl acetate and chloroform-methanol gave an amorphous solid which on purification by preparative TLC (or flash chromatography or column chromatography or Medium Pressure Liquid Chromatography or High Pressure Liquid Chromatography) afforded a solid compound. This compound designated as arunachalsterone, chemical name: 2,3,9,20,2l-pentahydroxy-cholest-7-en-6-one, melting point, 220-225°C, was analyzed for C27H44O6 by elemental analysis, FABMS (+) giving [M+] at 464, DEPT and 'H-13C correlated COSY. Infra-red spectrum (KBr) of arunachalsterone, chemical name: 2,3,9,20,21-pentahydroxy-cholest-7-en-6-one showed strong absorption bands at 3420 and 1645 cm-1 indicative of several hydroxyl and an A E-unsaturated carbonyl group. The 'H NMR (300 MHz ) spectrum of 1 revealed that it contained an A E-unsaturated carbonyl group (r5.78 d, J=l Hz), three proton under hydroxyls (1~"3.95 ddd, J=l,1.5 & 2 Hz; 3.80 ddd, J=12.3, 1.5 & 1 Hz and 3.34 dd, J=9.3 & 2 Hz), five hydroxyl signals ( T3.90, 3.6, 3.58, 3.25 and 2.61, all broad singlet), one allylic proton ( T3.10 ddt, J=8.7,l &1 Hz ), three methyl singlets (F 1.18 s , 0.99s , 0.90 s ), two methyl doublets (r0.89 d, J=6.4 Hz and 0.81 d, J=6.3 Hz) and methylene and methine protons. The 13C NMR (75 MHz) spectrum of it showed the presence of an A E-unsaturated carbonyl group ( T 202.499 s, 164.338 s and 119.934 d), tertiary hydroxyls (r 82.53 s, 75.221 s) and three secondary hydroxyls ( T 74.975 d, 66.248 d and 66.122 d). DEPT experiments revealed the presence of five methyls, eight methylenes, eight methines and six quarternary carbons in it. The proton carbon connectivity was determined by combined use of DEPT and 1H-13C COSY NMR experiments. The proton proton coupling network was finally determined by 1H-1H COSY90 experiment at 300 MHz. Based on the above evidences the structure of arunachalsterone, chemical name: 2,3,9,20,21- pentahydroxy-cholest-7-en-6-one was settled as 2,3,9,20,22-pentahydroxy-cholest-7-en-6-one, 1.. The structure of this new 14-dehydroecdysteroid, 1_, was further confirmed by the fact that acetylation of it with acetic anhydride (Ac20) and pyridine at r.t. (24 h) gave a dihydroxy triacetate 2, C33H50O9 by elemental analysis, was supported by EIMS giving molecular ion at 590. Other major peaks in the mass spectrum are at 573, 554, 540, 526, 512, 494 and 484. The IR spectrum showed the significant reduction in intensity of the bands at 3300 cm-' and appearance of a new band at 1725 cm-'. The 'H NMR spectrum revealed one olefinic proton (T 5.88 d, J=l Hz, H-7), three proton under acetate (r 5.35 ddd, J=l,1.5 & 2 Hz; 5.06 ddd, J=12.3, 1.5 & 1 Hz and 4.83 dd, J=9.3 & 2 Hz), one allylic proton (r3.12 ddt, J=8.7,l & 1 Hz ), two tertiary hydroxyls (r2.37 br s), three acetate (r2.116 for 6H and d 2.012 for 3H), three tertiary methyls (r 1.248 s, 1.035 s and 0.858 s) and two methyl doublets (r 0.892 d, J=6.3 Hz and d 0.885 d, J=7.2 Hz). The proton proton connectivity network of this dihydroxytriacetate derivative of arunachalsterone, chemical name: 2,3,9,20,21-pentahydroxy-cholest-7-en-6-one,l was determined by a 'H-1H COSY90. The stereochemistry of arunachalsterone, chemical name: 2,3,9,20,21-pentahydroxy-cholest-7-en-6-one 1 was established by two dimensional ROESY spectrum of it. In the ROESY spectrum, the cross peaks between H-2 and H-3, H-3 and H-4a, H-7 and H-15a, H-7 and H-15b (low intensity), H-2a and H-4a, H-5b and H-19, H-21 and H-18, H-17 and H-16a, H-22 and H-21 and H-17 and H-12a revealed its stereochemistry as depicted in 1.. The absence of cross peaks in the ROESY spectrum between H-22 and H-21 indicates their trans relationship. The non-formation of cross-peaks between H-19 and H-2 and H-19 and H-3 (or between H-19 and the hydroxyls at C-2 and C-3) indicates that C-19 methyl is equatorial while C-3 and C-2 hydroxyl groups are axial and equatorial respectively. The low coupling with J2ax,3eq= 1 Hz between H-2 (r5.06) and H-3 (r5.35) also supported these observations. The stereochemistry of H-5 was assigned as E, since there is no cross peak in the ROESY spectrum between H-5 & H-2 and H-5 & H-3. The ROESY spectrum also enabled to assign unambiguously 'H NMR signals of arunachalsterone, chemical name: 2,3,9,20,2l-pentahydroxy-cholest-7-en-6-one, i, at T3.90 br s, 3.60 br s, 3.58 br s, 3.25 br s and 2.61 as due to the hydroxyls at C-9, C-2, C-20, C-3 and C-22 respectively. The details of the process disclosed in this invention have been described in the following specific examples which are provided to illustrate the invention only and therefore these examples should not be construed to limit the scope of the present invention. Example I: Extraction and isolation of arunachalsterone, chemical name: 2,3,9,20,21-pentahydroxy-cholest-7-en-6-one, 1: Air dried and powdered needles and small branches (2 Kg) were exhaustively extracted with methanol in a soxhlet extractor for 20 h. The extract was concentrated under reduced pressure. The concentrated extract was first washed with hexane (200 ml x 3) and then with chloroform (150 ml x 6). The dried ( anhydrous Na2S04) chloroform extract was then distilled under reduced pressure to get a crude which on repeated gradient flash chromatography (or column chromatography or Medium Pressure Liquid Chromatography or High Pressure Liquid Chromatography or thin layer chromatography) with hexane-ethyl acetate and CHCI3-CH3OH gave a polar fractions from which precipitate of white amorphous powder separates on standing. These precipitates on purification by TLC (CHCI3-CH3OH, 10:1 ) (or flash chromatography or column chromatography or Medium Pressure Liquid Chromatography or High Pressure Liquid Chromatography) gave a solid, 2,3,9,20,21-pentahydroxy-cholest-7-en-6-one, 300 mg, 0.015 %, melting point 220-225°C, IR (KBr) Qmax3420, 2957, 1645, 1590, 1375, 1350, 1200, 1100, 1060 and 895 cm.-' 1H NMR (300 MHz): T5.78 d (J=l Hz, H-7), 3.95 ddd (J=l,1.5 & 2 Hz, H-3a), 3.90 br s ( OH, C-9), 3.80 ddd (J=12.3, 1.5 & 1 Hz, H-2a), 3.6 br s (OH,C-2), 3.58 br s (OH, C-20), 3.34 dd (J=9.3 & 2 Hz, H-22a), 3.25 br s (OH, C-3), 3.10 ddt (J=8.7,l &1 Hz, H-14a), 2.68 br s (OH,C-21), 2.40 dd (J=14.4 & 4.5 Hz, H-5b), 2.35 m (H-17a), 2.14 m (H-16a), 1.95 m ( H-la), 1.95 m (H-12b), 1.87 m (H-15a), 1.85 m (H-16b), 1.84m(H-15b), 1.80m(H-4b), 1.75 m (H-lla), 1.72m(H-4a), 1.68 m (H-12a), 1.68 m (H-llb), 1.55m(H-23a), 1.40 m (H-24a), 1.42 m (H-24b), 1.35 m(H-25), 1.31 m (H-23b), 1.28 m (H-lb), 1.18 s (H-21), 0.99s (H-19), 0.90 s (H-18), 0.89 d (J=6.4 Hz, H-26) and 0.81 d (J=6.3 Hz, H-27). 13C NMR (75 MHz) : T 202.4988 s (C-6), 164.3381 s (C-8), 119.9343 d (C-7), 82.5324 s (C-20), 75.2214 s (C-9), 74.9753 d (C-3), 66.2476 d (C-22), 66.1216 d (C-2), 49.1717 d (C-5), 47.8796 d (C-17), 46.1233 s (C-10), 36.9495 s (C-13), 35.7316 t (C-23), 35.3577 t (C-l), 32.4550 d (C-14), 30.2800 t (C-ll), 30.0066 t (C-4), 29.7377 t (C-16), 28.2056 t (C-24), 26.8396 d (C-25), 22.8619 q (C-19), 21.9909 q (C-26), 21.2941 q (C-27), 19.6068 q (C-21), 19.3529 t (C-12), 19.2730 t (C-15), 16.2002 q (C-18). (+)-FABMS :m/z at 617 [M++m-nitrobenzyl alcohol], 603,467 [M++ 3H], 464 [M+], 447 [ M+-OH], 436 [M+-CO], 430 [ M+-20H], 411 [M+-CH(CH3)2], 397. (Found C: 69.77 % and H: 9.53 % ; C27H44O6 requires C: 69.78% and H: 9.55%). Acetylation of Arunachalsterone, chemical name: 2,3,9,20,21-pentahydroxy-cholest-7-en-6-one 1: To a solution of 25 mg of compound 1 in 0.5 ml of pyridine was added 1 ml of Ac2O and left overnight. Usual work up and purification by preparative TLC ( EtOAc:Petrol, 1:10) (or flash chromatography or column chromatography or Medium Pressure Liquid Chromatography or High Pressure Liquid Chromatography) gave 20 mg of compound 2 as gum. IR (KBr) (=W: 3300, 2895, 1724, 1645, 1590, 1465, 1375, 1275, 1145, 1065 and 900 cm-'. 1H NMR (300 MHz) : 5.88 d (J=l Hz, H-7), 5.35 ddd (J=l,1.5 & 2 Hz, H-3), 5.06 ddd (J=12.3, 1.5 & 1 Hz, H-2), 4.83 dd (J=9.3 & 2 Hz, H-22), 3.12 ddt (J=8.7,l &1 Hz, H-14), 2.38 dd (J=14.4 & 4.5 Hz, H-5), 2.37 m (H-17), 2.172 m (H-lla), 2.116 s (6H, two acetate), 2.012 s (3H, acetate), 1.924 m (H-la),1.907 m (H-12a),1.910 m (H-4a), 1.877 m (H-llb), 1.875 m (H-4b),1.823 m (H-15a),1.728 m (H-16a), 1.681 m (H-12b), 1.607 m (H-16b), 1.585 m (H-15b), 1.565 m (H-25), 1.542 m (H-lb), 1.520 m (H-23a), 1.458 dd (J= 12 & 7.5 Hz, H-23b), 1.248 s (H-21), 1.17 ddd (J= 14.7, 7.5 & 1 Hz, H-24), 1.035 s (H-19), 0.892 d (J=6.3 Hz, H-26), 0.885 d (J=7.2 Hz, H-27), 0.858 s (H- 18). EIMS m/z at 590 [M+], 573, 554, 540, 526, 512, 494, 484, 479, 480, 469, 451, 447, 442, 437, 442, 429, 423, 413, 410, 401, 395, 392, 385, 382, 377, 351, 349, 334, 327, 321, 311, 303, 291, 271, 253, 260, 231,225,215,213,201, 198,197, 183,171, 173, 161, 157, 145, 133, 119, 105,93. (Found C: 67.08 % and H: 8.52 % ; C33H50O9 requires C: 67.09 % and H: 8.53 %). Example II: Extraction and isolation of arunachalsterone, chemical name: 2,3,9,20,21-pentahydroxy-cholest-7-en- 6-one, 1 : Air dried and powdered needles and small branches (4 Kg) were exhaustively extracted with methanol in a soxhlet extractor for 20 h. The extract was concentrated under reduced pressure. The concentrated extract was first washed with hexane (400 ml x 3) and then with chloroform (200 ml x 6). The dried ( anhydrous Na2SO4) chloroform extract was then distilled under reduced pressure to get a crude which on repeated gradient flash chromatography (or column chromatography or Medium Pressure Liquid Chromatography or High Pressure Liquid Chromatography or thin layer chromatography) with hexane-ethyl acetate and CHC13-CH3OH gave a polar fractions from which precepitate of white amorphous powder separates on standing. These precipitates on purification by TLC (CHC13-CH3OH, 10:1 ) (or flash chromatography or column chromatography or Medium Pressure Liquid Chromatography or High Pressure Liquid Chromatography) gave a solid, 2,3,9,20,21-pentahydroxy-cholest-7-en-6-one, 600 mg, 0.015 %, melting point 220-225°C, IR (KBr) Qmax as given in example I. 'H NMR (300 MHz) : as given in example I. 13C NMR (75 MHz): as given in example I. (+)-FABMS : as given in example I. Acetylation of Arunachalsterone, chemical name: 2,3,9,20,21-pentahydroxy-cholest-7-en-6-one I: To a solution of 40 mg of compound 1, in 0.5 ml of pyridine was added 1 ml of Ac20 and left overnight. Usual work up and purification by preparative TLC ( EtOAc:petrol, 1:10) (or flash chromatography or column chromatography or Medium Pressure Liquid Chromatography or High Pressure Liquid Chromatography) gave 30 mg of compound 2 as gum. IR (KBr) Qmax as given in example I. 1H NMR (300 MHz): as given in example I. EIMS as given in example I. Example III: Extraction and isolation of arunachalsterone, chemical name: 2,3,9,20,21-pentahydroxy-choIest-7-en-6-one, 1,: Air dried and powdered needles and small branches (6 Kg) were exhaustively extracted with methanol in a soxhlet extractor for 20 h. The extract was concentrated under reduced pressure. The concentrated extract was first washed with hexane (400 ml x 6) and then with chloroform (400 ml x 6), The dried ( anhydrous Na2SO4) chloroform extract was then distilled under reduced pressure to get a crude which on repeated gradient flash chromatography (or column chromatography or Medium Pressure Liquid Chromatography or High Pressure Liquid Chromatography or thin layer chromatography) with hexane-ethyl acetate and CHCl3:CH3OH gave a polar fractions from which precepitate of white amorphous powder separates on standing. These precipitates on purification by TLC (CHC13:CH30H, 10:1 ) (or flash chromatography or column chromatography or Medium Pressure Liquid Chromatography or High Pressure Liquid Chromatography) gave a solid, 2,3,9,20,2 l-pentahydroxy-cholest-7-en-6-one, 900 mg, 0.015 %, melting point 220-225°C, IR (KBr) Qmax as given in example I. 'H NMR (300 MHz): as given in example I. 13C NMR (75 MHz): as given in example I. (+)-FABMS : as given in example I. Acetylation of Arunachalsterone, chemical name: 2,3,9,20,21-pentahydroxy-cholest-7-en-6-one 1: To a solution of 50 mg of compound 1 in 0.5 ml of pyridine was added 1 ml of Ac20 and left overnight. Usual work up and purification by preparative TLC ( EtOAc:petrol, 1:10) (or flash chromatography or column chromatography or Medium Pressure Liquid Chromatography or High Pressure Liquid Chromatography) gave 40 mg of compound 2 as gum. IR (KBr) Qmax as given in example I. 'H NMR (300 MHz): as given in example I. EIMS as given in example I. Example IV: Extraction and isolation of arunachalsterone, chemical name: 2,3,9,20,21-pen tahydroxy-cholest-7-en-6-one, 1: Air dried and powdered needles and small branches (5 Kg) were exhaustively extracted with methanol in a soxhlet extractor for 20 h. The extract was concentrated under reduced pressure. The concentrated extract was first washed with hexane (400 ml x 4) and then with chloroform (200 ml x 6). The dried ( anhydrous Na2SO4) chloroform extract was then distilled under reduced pressure to get a crude which on repeated gradient flash chromatography (or column chromatography or Medium Pressure Liquid Chromatography or High Pressure Liquid Chromatography or thin layer chromatography) with hexane-ethyl acetate and CHC13:CH30H gave a polar fractions from which precepitate of white amorphous powder separates on standing. These precipitates on purification by TLC (CHCl3:CH3OH, 10:1) (or flash chromatography or column chromatography or Medium Pressure Liquid Chromatography or High Pressure Liquid Chromatography) gave a solid, 2,3,9,20,2 l-pentahydroxy-cholest-7-en-6-one, 750 mg, 0.015 %, melting point 220-225°C, IR (KBr) Qmax as given in example I. 1H NMR (300 MHz) : as given in example I.13C NMR (75 MHz): as given in example I. (+)-FABMS : as given in example I. Acetylation of Arunachalsterone, chemical name: 2,3,9,20,21-pentahydroxy-cholest-7-en-6-one 1: To a solution of 75 mg of compound 1 in 1 ml of pyridine was added 1 ml of Ac2 O and left overnight. Usual work up and purification by preparative TLC ( EtOAc:petrol, 1:10) (or flash chromatography or column chromatography or Medium Pressure Liquid Chromatography or High Pressure Liquid Chromatography) gave 50 mg of compound 2 as gum. IR (KBr) Qmax: as given in example I. 'H NMR (300 MHz): as given in example I. EIMS as given in example I. Example V: Extraction and isolation of arunachalsterone, chemical name: 2,3,9,20,21-pentahydroxy-cholest-7-en- 6-one, i: Air dried and powdered needles and small branches (1.5 Kg) were exhaustively extracted with methanol in a soxhlet extractor for 20 h. The extract was concentrated under reduced pressure. The concentrated extract was first washed with hexane (200 ml x 3) and then with chloroform (200 ml x 4). The dried ( anhydrous Na2SO4) chloroform extract was men distilled under reduced pressure to get a crude which on repeated gradient flash chromatography (or column chromatography or Medium Pressure Liquid Chromatography or High Pressure Liquid Chromatography or thin layer chromatography) with hexane-ethyl acetate and CHCl3:CH3OH gave a polar fractions from which precepitate of white amorphous powder separates on standing. These precipitates on purification by TLC (CHC13:CH30H, 10:1 ) (or flash chromatography or column chromatography or Medium Pressure Liquid Chromatography or High Pressure Liquid Chromatography) gave a solid, 2,3,9,20,2 l-pentahydroxy-cholest-7-en-6-one, 200 mg, 0.015 %, melting point 220-225°C, IR (KBr) Qmax as given in example I. 'H NMR (300 MHz): as given in example I. '3C NMR (75 MHz): as given in example I. (+)-FABMS : as given in example I. Acetylation of Arunachalsterone, chemical name: 2,3,9,20,21-pentahydroxy-cholest-7-en-6-one 1 : To a solution of 20 mg of compound 1 in 0.5 ml of pyridine was added 1 ml of Ac2O and left overnight. Usual work up and purification by preparative TLC ( EtOAc:petrol, 1:10) ( or flash chromatography or column chromatography or Medium Pressure Liquid Chromatography or High Pressure Liquid Chromatography) gave 15 mg of compound 2 as gum. IR (KBr) Qmax: as given in example I. 1H NMR (300 MHz): as given in example I. EIMS as given in example I. We Claim: 1. A process for the production of novel phyto-ecdysteroid of formula 1 wherein R is H or COCH3 which comprises; (Formula Removed) Formula 1 a) extracting the parts such as herein described of the plants Taxus baccata or Taxus baccata var.wallichiana with a polar organic solvent such as herein described, b) concentrating the extract by distilling at reduced pressure at a temperature range of 40-50°C to give residue, c) defatting the above said residue by washing with non polar solvents such as herein described, extracting the defatted residue with chloroform, concentrating the chloroform extract by known methods such as herein described and purifying by conventional repeated chromatographic methods as herein described to give 2,3,9,20,21 -pentahydroxy-cholest-7-en-6-one of formula 1 wherein R is H, d) converting pentahydroxy compound to acetate derivative of formula 1 wherein R is COCH3 by conventional acetylation methods such as herein described. 2. A process as claimed in claim 1 wherein the plant materials of Taxus baccata or Taxus baccata var.wallichiana used is selected from seed kernels, leaves, barks, roots or any other parts of the plant. 3. A process as claimed in claims 1 to 2 wherein the polar organic solvent used for the extraction is selected from any polar protic solvents preferably alcohoic solvents such as methanol, ethanol, propanol. 4. A process as claimed in claim 1 to 3 wherein the defatting is carried out by non-polar solvent selected from pentane, hexane, petroleum ether. 5. A process as claimed in claims 1 to 4 wherein purification is carried out by thin layer chromatography, flash chromatography, high performance liquid chromatography using silica gel as adsorbent. 6. A process as claimed in claims 1 to 6 wherein the solvents used for chromatography are selected from hexane, chloroform, ethyl acetate, methanol and their mixtures. 7. A process as claimed in claims 1 to 6 wherein the acetylation is carried out by acetic anhydride in pyridine. 8. A process for the production of novel phytoecdysteriods substantially as herein described with reference to the examples.

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