Glucopyranoside, process for isolation thereof,...

Details Glucopyranoside, process for isolation thereof,... Glucopyranoside, process for isolation thereof,...

2002-03-29

2003-05-13

Barts, Samuel (Department: 1623)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Carbohydrate doai

C514S866000, C514S456000, C536S124000, C536S128000

Reexamination Certificate

active

06562791

ABSTRACT:

FIELD OF THE INVENTION
The present invention relates to a novel glucopyranoside, 6-hydroxy-2-p-hydroxybenzylbenzofuran-7-C-&bgr;-D-glucopyranoside of the formula 1
The present invention also relates to a process for the isolation of said novel glucopyranoside of formula 1 from
Pterocarpus marsupium.
More particularly, the present invention relates to a process of isolation of 6-hydroxy-2-p-hydroxybenzylbenzofuran-7-C-&bgr;-D-glucopyranoside of formula 1, from
Pterocarpus marsupium.
The present invention also relates to a pharmaceutical composition containing 6-hydroxy-2-p-hydroxybenzylbenzofuran-7-C-&bgr;-D-glucopyranoside of the formula 1 and to method for the treatment of diabetes using said compound of formula 1.
BACKGROUND OF THE INVENTION
Pterocarpus marsupium
Roxb (Leguminosae) 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, V. 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 use as an antidiabetic drug.
Hypoglycaemic 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; Kedar, P. and Chakrabarti, C. H.,
Maharashtra 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 but 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. The ether extract of
P. marsupium
heartwood furnished isoflavonoid glycol 4,4-dihydroxy-&agr;-methylhydrobenzoin designated Marsupol [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 [Rao, 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 Rambhav, S.
Current Science,
1984, 53, 576], 6-hydroxy-7-O-methyl-3-(3-hydroxy-4-O-methyl benzyl)chroman-4-one [Jain, S. C., Sharma, S. K., Kumar, R., Rajwansh, V. K. and Babu, V. R.,
Phytochemistry,
1997, 44, 765].
2. Ethyl acetate soluble fraction of alcoholic extract of the heartwood furnished pterosupin &bgr;,2′,4,4′-tetrahydroxy-3′(c-&bgr;-D-glucopyranoside)dihydrochalcone [Adinarayana, D., Syamsundar, K. V., Seligmann, O., and 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, retusin-O-&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 the ethyl acetate soluble fraction of alcoholic extract of the heartwood.
3. Novel benzofuranone derivative, 2,6-dihydroxy-2-(p-hydroxybenzyl)-4-methoxy-3(2H)-benzofuranone designated marsupin [Maurya, R., Ray, A. B., Duah, F. K., Slatkin, D. J. and Schiff, P. L. Jr.,
Heterocycles,
1982, 19, 2103], pterostilbin, (2S)-hydroxyflavone, isoliquiritigenin, liquiritigenin, 7,4′-dihydroxyflavone, 5-deoxykaempferol and 3,7,4′-trihydroxyflavone [Maurya, R., Ray, A. B. Duah, F. K., Slatkin, D. J. and Schiff, P. L. Jr.,
J. Nat. Prod.
1984, 47, 179], two C-glycosides, 8-C-&bgr;-D-glucopyranosyl-3,7,4′-trihydroxy and 3,7,3′,4′-tetrahydroxy flavone and 3′-C-&bgr;-D-glucopyranosyl-&agr;-hydroxy dihydrochalcone [Bezuidenhoudt, B. C. B., Brandt, E. V., and Ferreira, E. V.,
Phytochemistry,
1987, 26, 531] from ethyl acetate extract of defatted heartwood.
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 obtain novel bioactive fractions from water extracts of heartwood of
Pterocarpus marsupium
which are useful in treatment of diabetes.
SUMMARY OF THE INVENTION
The above and other objects of the invention are achieved by partitioning an aqueous extract of powdered heartwood of
Pterocarpus marsupium
with different organic solvents. The novel bioactive fraction, 6-hydroxy-2-p-hydroxybenzylbenzofuran-7-C-&bgr;-D-glucopyranoside is isolated from the polar fraction by choromatographic techniques and is found to show hypoglycaemic activity. There is no disclosure in the prior art of this compound since work had been done in the art on the ether extract, ethyl acetate extract and ethyl acetate soluble fraction of the alcoholic extract.
Accordingly, the present invention provides a novel glucopyranoside 6-hydroxy-2-p-hydroxybenzylbenzofuran-7-C-&bgr;-D-glucopyranoside of formula 1 where R is H or COCH
3
The present invention also provides a process for the isolation of 6hydroxy-2-p-hydroxybenzylbenzofuran-7-C-&bgr;-D-glucopyranoside of the formula 1 which comprises:
(a) powdering the heartwood of the plant
Pterocarpus marsupium,
(b) extracting the powdered plant material with a protic solvent,
(c) concentrating the extract to minimum volume

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