Water-soluble pentacyclic triterpene composition and method for

Details Water-soluble pentacyclic triterpene composition and method for Water-soluble pentacyclic triterpene composition and method for

1992-10-23

1994-05-24

Griffin, Ronald W.

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Carbohydrate doai

424 48, 424 49, 514529, 514557, 514835, 514886, 514894, 536103, A61K 716, C07C 6232, C07C 5150, A23L 103

Patent

active

053148770

DESCRIPTION:

BRIEF SUMMARY
TECHNICAL FIELD

This invention relates to water-soluble pentacyclic triterpene compositions which are made soluble in water while preserving the pharmacological function of pentacyclic triterpene compounds (hereinafter, referred to as triterpene), and a method for producing the same.


BACKGROUND ART

Triterpenes are classified into amylin, lupeol, nosterol and squalene groups. These are all compounds which are insoluble in water and soluble in oil, organic solvents or the like.
The triterpenes are widely distributed in throughout the plant kingdom in the form of a free radical and bound with sugar into saponin or with acid into ester. The amylin group of the triterpenes, which is represented by a chemical formula having an OH-radical at the third position and a COOH-radical at the seventeenth position is a compound as represented by the following formula [1]. The compounds thereof are typically oleanolic acid, ursolic acid and hederagenin as concretely shown in Table 1 below.
The oleanolic acid mentioned above is variously found in a beet in the form of saponin and in the leaves of an olive, a green perilla, a jujube, and a ground ivy, the peel of an apple, the germ of a clove and so on. The ursolic acid is obtained from not only fruit such as an apple and a cherry and waxy coat material of the leaf thereof, but also the leaves of the ground ivy, jujube tree and so on. Furthermore, hederagenin is found in hedera helix, the fruit of a soapberry and so on. ##STR1## wherein, R.sub.1 represents CH.sub.3 or CH.sub.2 OH, R.sub.2 represents H or OH, R.sub.3 represents H or CH.sub.3, R.sub.4 represents H or CH.sub.3, and R.sub.5 represents H or OH.


TABLE 1 ______________________________________ Compound R.sub.1 R.sub.2 R.sub.3 R.sub.4 R.sub.5 ______________________________________ Amylins Oleanolic acid CH.sub.3 H CH.sub.3 H H Ursolic acid CH.sub.3 H H CH.sub.3 H Pomolic acid CH.sub.3 H H CH.sub.3 OH Hederagenin CH.sub.2 OH H CH.sub.3 H H Echinocystic acid CH.sub.3 OH CH.sub.3 H H ______________________________________
On the other hand, there have been recently carried forward investigations as to substances having pharmacological functions in various plants including medicinal herbs by research laboratories of universities, public and private research institutions and nongovernmental laboratories. Then, it has been confirmed that the amylins of a triterpene group present in a plant, which is represented by a chemical formula having an OH-radical at the third position and a COOH-radical at the seventeenth position, shows pharmacological activity such as antibiosis relative to a tumor, hepatitis, inflammation and caries. Various types of amylin groups have been so far reported in academic societies and in literatures, reviewed in news papers and magazines and proposed by patents.
The inventors of the present invention have also conducted experiments on the pharmacological function of oleanolic acid obtained from a sugar beet and confirmed that the oleanolic acid has the effects of antibiosis to a tumor and hepatitis, cariostatic (insoluble glucanynthesis inhibition) and so on.
Further, as a use of oleanolic acid, there have been proposed compositions for use in the mouth on the basis of the pharmacological function of oleanolic acid (Japanese Patent Publication No. SHO 63-26083).
However, as these triterpenes are insoluble in water, the pharmacological experiments as mentioned above were conducted using specimens obtained by dissolving the triterpene into an organic solvent such as dimethyl sulfoxide (hereinafter referred as to DMSO), ethanol, propylene glycol, and butanediol so as to make the "in vitro" and "in vivo" tests no matter how coarse or fine the triterpene applied therefor is.
There are a good many cases of using particularly DMSO having the high boiling point and high solvent power as the organic solvent applied for the tests as noted above. However, the DMSO is not approved as an additive to foods, drinks or compositions for use in the mouth. Also, the oth

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