8-(C-&bgr;-D-glucopyranosyl)-7, 3',...

Details 8-(C-&bgr;-D-glucopyranosyl)-7, 3',... 8-(C-&bgr;-D-glucopyranosyl)-7, 3',...

2002-03-28

2004-08-17

Wilson, James O. (Department: 1623)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Carbohydrate doai

C536S008000

Reexamination Certificate

active

06777392

ABSTRACT:

FIELD OF THE INVENTION
The present invention relates to a novel compound, 8-(C-&bgr;-D-glucopyranosyl)-7,3′,4′-trihydroxyflavone. The present invention also relates to a process for the isolation of said novel compound 8-(C-&bgr;-D-glucopyranosyl)-7,3′,4′-trihydroxyflavone from
Pterocarpus marsupium
. The present invention also relates to a pharmaceutical composition containing 8-(C-&bgr;-D-glucopyranosyl)-7,3′,4′-trihydroxyflavone and to method for the treatment of diabetes using said compound.
BACKGROUND OF THE INVENTION
Pterocarpus marsupium
Roxb (Legumtnosae) also known as Indian Kino tree or Bijasar, is common in the hilly regions of central and peninsular India [Jain, S. K., Medicinal Plants, National Book Trust, New Delhi, 1968, p. 116]. The extracts of leaves, flowers and gum of this tree have been used medicinally in the treatment of diarrhea, toothache, fever, urinary tract and skin infections. [Chopra, R. N., Chopra, I. C., Handa, K. L. and Kapur, L. D., Indigenous Drugs of India, 2nd Ed., Dhar. U. N. and Sons Private Limited, Calcutta, 1958, p. 522]. The extract of the bark has long been regarded as useful in the therapy of diabetes [Kirtikar, K. R. and Basu, B. D., Indian Medicinal Plants, 2nd Ed., edited by Blatter, E., Cailes, J. F. and Mhaskar, K. S., Singh and Singh, Delhi, India, 1975, p. 2135]. It is reported by Chakravarthy et al [Chakravarthy, B. K., Gupta, S and Gode, K. D., Lancet, 1982, 272 (and references cited therein)] that the active hypoglycemic principle of the bark is (−)-epicatechin and that its effect is due to the regeneration of pancreatic beta cells. However, this claim has been questioned by Kolb et al [Kolb, H., Kiesel, U., Grenlich, B. and Bosch, J. V. D., Lancet, 1982, 1303.] and Sheehan et al [Sheehan, E. W., Zemaitis, M. A., Slatkin, D. J. and Schiff, Jr., P. L., Journal of Natural Products, 1983, 46, 232]. It is now felt that further investigation is necessary before (−)-epicatechin can be considered a viable antidiabetic agent for use in human clinical studies.
Practitioners of the Indian System of Medicine are of the view that the heartwood rather than the bark of
Pterocarpus marsupium
is useful for treatment of diabetic patients and that older the plant more efficacious is its heartwood. It is also claimed that only heartwood that is distinctly red in colour and which imparts a red colouration with bluish green fluorescence to water in which it is kept soaked is suitable for used as an antidiabetic drug.
Hypoglycemic effects of aqueous or alcoholic extracts of heartwood of
Pterocarpus marsupium
have been verified by experimental [Shah, D. S.,
Indian Journal of Medical Research,
1967, 55, 166 and references cited therein; Gupta, S. S.,
Indian Journal of Medical Research,
1963, 51, 716] and clinical studies [Sepha, G. C. and Bose, S. N.,
J. Ind. Med. Assoc.,
1956, 27, 383; Ledar, P. and Chkrabarti, C. H.,
Maharastro Med. J.,
1981, 28, 165].
The heartwood of
Pterocarpus marsupium
is rich in phenolics Chemical investigation on heartwood of
P. marsupium
dates back to 1946 by early works [Bhargava, P. N.,
Proc. Ind. Acad. Sci.,
1946, 24A, 496] on this drug are fragmentary in nature. Previous reported studies on this plant disclose the following chemical constituents.
1. Ether extract of
P. marsupium
heartwood furnished isoflavonoid glycol 4,4′-dihydroxy-&agr;-methylhydrobenzoin designated Marsupial [Rao, A. V. S., Mathew, J.,
Phytochemistry,
1982, 21, 1837], a benzofurannone derivative, 2,4′,6-trihydroxy-4-methoxybenzo(b)furan-3(2H)-one designated carpusin [Mathew, J. and Rao, A. V. S.;
Phytochemistry,
1983, 22, 794], 2-propanol derivative, 1,3-bis (4-hydroxyphenyl)propan-2-ol, designated propterol [Kan, A. V. S., Mathew, J. and Shankaran, A. V. B.,
Phytochemistry,
1984, 23, 897], 1-(2,4-dihydroxyphenyl)-3-(4-hydroxyphenyl)propan-2-ol designated propterol B [Mathew, J., Rao, A. V. S. and Rambbav, S.
Current Science,
1984, 53, 576], 6-hydroxy-7-O-methyl-3-(3-hydroxy-4-O-methyl benzyl) chroman-4-one [Jain, S. C., Sharman, S. K., Kumar, R, Rajwansh, V. K. and Babu, V. R.,
Phytochemistry,
1997, 44, 765].
2. Hthylacetate soluble fraction of alcoholic extract of heartwood furnished pterosupin &bgr;, 2′,4,4′-tetrahydroxy-3′(C-&bgr;-D-glucopyranoside)dihydrochalcone [Adinarayana, D., Syamsundar, K. V., Seligmann, ( ), & Wagner, H., (Z. Naturforsch, 1982, 37C, 145)], Marsupinol [Trivedi, J. J.,
Indian J. Phys. Pharmacol,
1997, 15, 51], 5,4′-dimethoxy-8-methylisoflavone-7-O-&agr;-L-rhamnopyranoside, restusin-( )-&bgr;-D glucopyranoside and irisolidine 7-O-&agr;-L-rhamnopyranoside [Mitra, J. and Joshi, T.,
Phytochemistry,
1982, 21, 2429] and 5,7′-dihydroxy-6-methoxy-7-O-&agr;-L-rhamnopyranoside [Mitra, J. and Joshi, T.,
Phytochemistry,
1983, 22, 2326] obtained from ethylacetate soluble fraction of alcoholic extract of heartwood.
3. Benzofurannone derivative, 2,6-dihydroxy-2-(p-hydroxybenzyl)-4-methoxy-3(2H)-benzofurannone designated as marsupin [Maurya, R., Ray, A. B., Duah, F. K., Slatkin, D. J. & Schiff, P. L. Jr.,
Heterocycles,
1982, 19, 2103] & pterostilbin, (2S)-hydroxyflavone, isoliquiritigein, liquiritigenin, 7,4′-dihydroxyflavone, 5-denoxykaempferol & 3,7,4′-trihydroxyflavone [Maurya, R., Ray, A. B. Duah, F. K., Slatkin, D. J. & Schiff, P. L. Jr.,
J. Nat. Prod
1984, 47, 179], two C-glycoisdes, 8-C-&bgr;-D-glucopyranosyl-3,7,4′-trihydroxy & 3,7,3′,4′-tetrahydroxyflavone & 3′-C-&bgr;-D-glucopyranosyl-&agr;-hydroxy dihydrochalcone [Bezuidenhoudt, B. C. B., Brandt, E. V., and Ferreira, E. V.,
Phytochemistry,
1987, 26, 531] from ethylacetate extract of detatted heartwood.
4. The petrol extract of
P. marsupium
root afforded selin-4(15)-one-1&bgr;, 11-diol, &bgr;-eudesmol, erythrodiol-3-monoacetac and pterostilbene [Admarayana, D., and Syamasundar, K. V.,
Phytochemistry,
1982, 22, 1083]. Ethanolic extract of
P. marsupium
flowers furnished 4,6,4′-trihydroxyaurone 6-O-rhamnopyranoside and 4,6,4′-trihydroxy-1-methylantrone 4-O-rhamnopyranoside [Mohan, P., and Joshi, T.,
Phytochemistry,
1989, 28, 1287] and ethanolic extract of
P. marsupium
bark furnished (−)-epicatechin [Chakravarthy, B. K., and Gode, K. D.,
Planta Medica,
1985, 56].
However, the prior art does not provide any details about the biological activities associated with such chemical constituents. Also prior art discloses only preparation of ether extract, ethyl acetate extract and ethyl acetate soluble fraction of the alcoholic extract but does not disclose any method of preparing water extracts of heartwood of
Pterocarpus marsupium
and attempting to isolate any chemical constituents therefrom.
OBJECTS OF THE INVENTION
The main object of the invention is to accordingly prepare water extracts of the heartwood of
Pterocarpus marsupium
and to obtain chemical constituents therefrom.
It is another object of the invention to investigate the water extracts of heartwood of
Pterocarpus marsupium
to obtain bioactive fractions useful in the treatment of diabetes.
SUMMARY OF THE INVENTION
The above and other objects of the invention are achieved by preparing a n-butanol soluble water extract of investigate the water extract of heartwood of
Pterocarpus marsupium
and isolating a novel bioactive fraction therefrom. Accordingly, the present invention provides a novel compound 8-(C-&bgr;-D-glucopyranosyl)-7,3′,4′-trihydroxyflavone.
The present invention also provides a process for the isolation of 8-(C-&bgr;-D-glucopyranosyl)-7,3′,4′-trihydroxyflavone which comprises:
(a) powdering the heartwood of the plant
Pterocarpus marsupium,
(b) extracting the powdered plant material so prepared with a protic solvent,
(c) concentrating the extract to

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