Chemistry: molecular biology and microbiology – Enzyme – proenzyme; compositions thereof; process for... – Lyase
Reexamination Certificate
1999-04-19
2001-12-11
Lilling, Herbert J. (Department: 1651)
Chemistry: molecular biology and microbiology
Enzyme , proenzyme; compositions thereof; process for...
Lyase
C435S125000
Reexamination Certificate
active
06329189
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to the novel tartaric acid ether compounds useful as pharmaceuticals, functional foods and the like. More particularly, it relates to a novel enzyme producing tartaric acid ether compound which catalyzes a reaction of producing a tartaric acid ether compound in which the phenolic hydroxyl group(s) of flavonoids or the analogous compounds having phenolic hydroxyl group(s) is acted to an epoxy ring of an epoxysuccinic acid to form an ether linkage, an enzymatic process for producing the tartaric acid ether compounds using the said enzyme, and the novel tartaric acid ether compounds.
2. Description of the Related Prior Art
It is known that 2-hydroxy-3-[[3-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-7-yl]oxy]-butanedioic acid (see “Isoflavone derivative peak A” in JP-A-9-110857), 2-hydroxy-3-[[5-hydroxy-3-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-7-yl]oxy]-butanedioic acid (see “Isoflavone derivative peak B” in JP-A-9-110857) and 2-[[5,8-dihydroxy-3-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-7-yl]oxy]-3-hydroxy-butanedioic acid (see “Isoflavone derivative peak A” in JP-A-10-59956), which are the tartaric acid ether compounds and the isoflavone derivatives, show a prominent inhibitory action against histidine decarboxylase (HDC) which takes part in the biosynthesis of histamine causative of ulcers and allergic diseases, and thus are very useful for the preparation of pharmaceuticals and functional foods free from harmful side effects.
Hitherto, despite their manifold physiological activities such as antioxidant action, HDC inhibitory action, estrogen-like action and anti-ulcer action, many of the flavonoids or their analogous compounds have fallen short of exhibiting their potential efficacy in the living body, just because of their low solubility in water.
The glycosides of flavonoids or their analogues show high solubility in water but are unstable in their structure. In contrast, the tartaric acid ether compounds of flavonoids or their analogues are very stable structurally.
In view of the above, it is significantly important to provide the tartaric acid ether compounds with high water solubility and stable structure, for example, the tartaric acid ether compounds of flavonoids and their analogues. Hitherto, various methods, such as synthesis through substitution reaction, synthesis through addition reaction, synthesis through leaving reaction or condensation reaction, synthesis through oxidation reaction and synthesis through reduction reaction, have been proposed and used for producing the ether compounds, but any of these methods has recourse to a chemical reaction and involves complicate operations and steps in connection with the reaction conditions and reaction reagents, and also requires specific synthesizing equipment. On the other hand, these has not entirely been known the technique for producing the tartaric acid ether compounds at low cost and with ease according to the enzyme process.
SUMMARY OF THE INVENTION
The present invention has been made with the object of overcoming these prior art problems in the synthesis of the tartaric acid ether compounds, finding out a novel enzyme capable of producing the tartaric acid ether compounds useful for the pharmahydroxy-butanedioic ceuticals and functional foods, and providing a process for producing the tartaric acid ether compounds with high water solubility and stable structure at low cost and with high precision and ease by using the said enzyme, while also offering the novel tartaric acid ether compounds.
In the course of the studies for attaining the above object, the present inventors found that the microorganisms belonging to the genus Aspergillus are capable of yielding a novel enzyme which is productive of the tartaric acid ether compounds by letting the phenolic hydroxyl group(s) of a flavonoid or its analogous compound having at least one phenolic hydroxyl group react with the epoxy ring of an epoxysuccinic acid, and that use of such an enzyme enables easy enzymatic formation of various tartaric acid ether compounds. The present invention has been completed on the basis of the above finding.
Thus, the present invention provides a novel enzyme producing tartaric acid ether compound which catalyzes a reaction of forming a tartaric acid ether compound in which the phenolic hydroxyl group(s) of a flavonoid or its analogous compound having at least one phenolic hydroxyl group is(are) acted to the epoxy ring of an epoxysuccinic acid to form ether linkage of one or more tartaric acid residues. The present invention also provides a process for producing the tartaric acid ether compounds, which comprises acting the said novel enzyme producing tartaric acid ether compound in the presence of an epoxysuccinic acid and a flavonoid or its analogous compound having at least one phenolic hydroxyl group. It is also envisaged in the present invention to provide the novel tartaric acid ether compounds in which the phenolic hydroxyl group(s) of a flavonoid or its analogous compound having at least one phenolic hydroxyl group is reacted with the epoxy ring of an epoxysuccinic acid to form ether linkage of one or more tartaric acid residues.
REFERENCES:
patent: 9-110857 (1997-04-01), None
patent: 10-059956 (1998-03-01), None
Aishima Tetsuo
Kinoshita Emiko
Ozawa Yoshinori
Banner & Witcoff , Ltd.
Kikkoman Corporation
Lilling Herbert J.
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