Mixtures derived from grains of eugenia jambolana lamarck, prepa

Drug – bio-affecting and body treating compositions – Antigen – epitope – or other immunospecific immunoeffector – Conjugate or complex

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A61K 31495, A61K 31195, A61K 3578, A01N 6500

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active

059723424

DESCRIPTION:

BRIEF SUMMARY
The present invention relates to mixtures which can be isolated from Eugenia Jambolana Lamarck seeds (Myrtaceae family), medicaments containing these mixtures or some of their constituents, the use of these mixtures and constituents for the preparation of an antidiabetic medicament and their preparations.
A plant extract prepared from Eugenia Jambolana seeds or bark containing a polyphenol and sterol mixed complex is described in patent FR 2,465,484.
New mixtures which can be isolated from Eugenia Jambolana Lamarck seeds, and which are free of polyphenol and sterol complex, as well as certain constituents of these mixtures endowed with hypoglycaemic properties, have now been found.
These mixtures are characterized in that they are free of polyphenol and sterol derivatives and can be isolated by grinding Eugenia Jambolana Lamarck seeds, maceration of the powder with a lower aliphatic alcohol with the use of heat, filtration, recovery of the insoluble part no longer containing polyphenol and sterol compounds, treatment of the insoluble part with an ammoniacal solution, treatment of the ammoniacal mixture with a lower aliphatic alcohol with the use of heat, filtration, recovery of the insoluble matter and drying this insoluble matter which constitutes the mixture I, then optionally treatment of the mixture I with a water-lower aliphatic alcohol solution, filtration, partial concentration of the filtrate, purification on nonpolar adsorbent resins, partial concentration, centrifugation, ultrafiltration and isolation of the mixture II.
From the mixture II, there may also be separated sodium oxamate and the compounds of formula: ##STR1## in which either R.sub.1 represents a hydrogen atom and R.sub.2 represents a chain of formula: ##STR2## or R.sub.1 represents a chain of formula (A) and R.sub.2 represents a hydrogen atom.
Sodium oxamate has already been described by TOUSSAINT, Ann., 120, 237 (1861).
The compounds of formula (I) have already been described by KUHN et al., Ann., 644, 122-127 (1961); TSUCHIDA et al., Agr. Biol. Chem., 39 (5), 1143-1148 (1975); TSUCHIDA et al., Agr. Biol. Chem., 40 (5), 921-925 (1976); TSUCHIDA et al., Nippon Shokuhin Kogyo Gakkaishi, 37, 154-161 (1990) and AVALOS et al., tetrahedron, 49, 2655-2675 (1993).
The present invention also relates to the process for preparing the mixture I from dried and finely ground Eugenia Jambolana Lamarck seeds.
The powder is screened, preferably with the aid of a normalized screen with holes 0.5 .mu.m in diameter and then subjected to the following treatment: temperature of between 40 and 70.degree. C., aliphatic alcohol at a temperature of between 40 and 70.degree. C., mainly the undesirable polyphenols and sterols, temperature of between 10 and 30.degree. C., alcohol solution, at a temperature of between 40 and 70.degree. C., filtration and removal of the alcoholic solution,
In step a, the procedure is generally carried out by means of 2 to 10 liters of a lower aliphatic alcohol such as methanol or ethanol per 1 kg of screened powder. Preferably, 5 liters of ethanol with a titre of 93-95.degree. Gay Lussac are used at 60.degree. C. for 1 hour.
The filtration of step b is preferably carried out under a vacuum of 40 kPa.
In step c, the procedure is generally carried out by means of 2 to 10 liters of a lower aliphatic alcohol such as methanol or ethanol per 1 kg of starting screened powder. Preferably, 4 liters of ethanol with a titre of 93-95.degree. Gay Lussac are used at a temperature of 60.degree. C. for 1 hour.
The filtration of step d is preferably carried out under a vacuum of 40 kPa.
In step e, per 1 kg of starting screened powder, 750 to 1250 ml of an aqueous ammoniacal solution preferably containing 350 ml of 28% ammonium hydroxide per 1000 ml are generally used. It is particularly advantageous to use 1 liter of the aqueous ammoniacal solution and to carry out the procedure for 10 to 30 hours and, preferably, 20 hours at a temperature close to 20.degree. C.
In step f, the wet ammoniacal mass obtained from 1 kg of starting screened powder is g

REFERENCES:
patent: 3660571 (1972-05-01), Kodama et al.
Derwent Abstract of FR 2 465 484, Mar. 27, 1981.
Derwent Abstract of DE 2 159 923, Jun. 14, 1973.
Derwent Abstract of FR 6114, Jun. 17, 1968.
Kitaoka et al., "2,5-Bis-D-Glucopyrazine," Chemical Abstracts, 74(25):142298e (1971).

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