Process for producing a cholesterol-reduced substance

Details Process for producing a cholesterol-reduced substance Process for producing a cholesterol-reduced substance

1994-02-10

1996-04-02

Lilling, Herbert J.

Chemistry: molecular biology and microbiology

Micro-organism, tissue cell culture or enzyme using process...

Preparing compound containing a...

435189, C12P 3300, C12N 902

Patent

active

055039880

DESCRIPTION:

BRIEF SUMMARY
TECHNICAL FIELD

The present invention relates to a process for producing a cholesterol-reduced substance; a novel cholesterol oxidase and a novel epicholesterol dehydrogenase to be used in the process; a process for producing these enzymes; and a process for producing epicholesterol with the use of the epicholesterol dehydrogenase.
It has been reported that excessive intake of foods having a high cholesterol content causes increase in a concentration of cholesterol in blood serum, and that a high concentration of serum cholesterol is an important risk factor for heart disease (Dairy Council Digest, 60 (2), 7, 1989). Thus, for the purpose of providing low-cholesterol foods and low-cholesterol feed, methods for the selectively reducing cholesterol level in foods and feed are in demand. In addition, simple and safe process for producing epicholesterol having a high purity are also in demand. Highly purified epicholesterol is useful in physiological researches.


PRIOR ART

It is known that cholesterol-reduced substances may be obtained by extracting cholesterol from foods with hexane or acetone (Japanese Published Examined Patent Application No. 42944/71 and Japanese Published Unexamined Patent Application No. 19062/72) and by supercritical carbon dioxide extraction (Japanese Published Unexamined Patent Application Nos. 135847/84, 167035/90 and 98541/91).
It is also known that cholesterol-reduced butter may be obtained by adsorbing cholesterol using polymer-supported digitonin J. Agric. Food Chem., 38 (9), 1839 (1990)!.
It is also known that cholesterol-reduced food may be obtained by adding .beta.-cyclodextrin to the egg yolk solutions or milk products, and then separating insoluble complexes of cholesterol and .beta.-cyclodextrin by centrifugation (Japanese Published Unexamined Patent Application Nos. 252259/89, 98553/91 and 49647/91).
In the above mentioned extraction and adsorption methods, lipids and flavor components are also extracted in addition to cholesterol, and thus the quality of foods is deteriorated.
On the other hand, a method of degrading cholesterol in foods with microorganisms Japanese Published Unexamined Patent Application No. 267231/88, J. of Food Science, 53 (2), 659 (1989)! and a method of converting cholesterol with cholesterol reductase to coprostanol (U.S. Pat. No. 4,921,710) are known.
Treatment with phospholipase (Japanese Published Unexamined Patent Application No. 49414/93) and treatment with protease or lipase (Japanese Published Unexamined Patent Application No. 76311/93) are known to promote the above-mentioned treatment with microorganisms or enzymes.
In addition, a cholesterol oxidase which oxidizes cholesterol to 4-cholesten-3-one (EC 1.1.3.6), a cholesterol oxidase produced by Basidiomycetes which oxidizes cholesterol to 5-cholesten-3-one (Japanese Published Unexamined Patent Application No. 48159/85), a cholesterol dehydrogenase which oxidizes cholesterol to cholestenone (Japanese Published Examined Patent Application No. 18064/90, Japanese Published Unexamined Patent Application No. 56090/78) and a 3-.alpha.-hydroxysteroid dehydrogenase which oxidizes the 3-.alpha.-hydroxyl group to cholic acid (EC 1.1.1.50) are known.
It is known that epicholesterol is scarcely absorbed through intestines Journal of Biological Chemistry, 206, 757 (1954)!. It is not known that cholesterol-reduced substances can be produced by converting cholesterol in foods into epicholesterol. Epicholesterol dehydrogenase which oxidizes epicholesterol to cholestenone in the presence of NAD(P) is not known. Furthermore, cholesterol oxidase which is produced by microorganisms belonging to the genus Botrytis, and which oxidizes cholesterol to 5-cholesten-3-one is not known. On the other hand, a chemical method for the conversion of cholesterol to epicholesterol is known Journal of Organic Chemistry 40 (9), 1361, (1975)!.


DISCLOSURE OF THE INVENTION

The present invention provides a novel process for producing a cholesterol-reduced substance. The present invention also provides a novel epicholesterol de

REFERENCES:
patent: 4181575 (1980-01-01), Gruber et al.
patent: 4921710 (1990-05-01), Beitz et al.
J. Agric. Food Chem., 38 (9), 1839 (1990) pp. 1839-1843; T. Micich.
J. of Food Science, 53 (2), 659 (1989), vol. 53, No. 2, pp. 659-660; Watanabe, et al.
Journal of Biological Chemistry, 206, 757, (1954), pp. 757-765; Hernandez, et al.
Journal of Organic Chemistry, 40 (9), 1361, (1975), vol. 40, No. 9, pp. 1361-1362; Y. Houminer.

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