JPH10139718A - Production of eicosapentaenoic acid - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain the subject compound useful for treatment of arteriosclerosis, etc., by producing eicosapentaenoic acid phloroglucinol from a brown alga of the family Dictyotaceae and hydrolyzing the compound in an alkali. SOLUTION: Eicosapentaenoic acid is produced by extracting a brown alga such as Distromium decumbens and Zonaria diesingiana with an organic solvent such as hexane or acetone, purifying the extract by chromatography to obtain eicosapentaenoic acid phloroglucinol and hydrolyzing the product in an alkali such as sodium hydroxide or potassium hydroxide while keeping the pH of the reaction liquid preferably to 12-14. The compound is useful as an agent for the treatment of hyperlipidemia, a nutritional supplementary food, a nutritional additive for the culture of fish and shell fish, etc.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

[0001] The present invention relates to a method for producing a highly unsaturated fatty acid eicosapentaenoic acid. Eicosapentaenoic acid is useful for treating arteriosclerosis, treating hyperlipidemia, dietary supplements, nutritional additives for cultured fish and shellfish, and the like.

[0002]

2. Description of the Related Art Eicosapentaenoic acid is currently mainly collected from sardine oil, and it is known that chlorella, specific filamentous fungi and bacteria have the ability to produce it. In addition, a method of collecting from a culture of Pasteurella bacteria (Japanese Patent Application Laid-Open No. 64-2587) and a method of introducing an eicosapentaenoic acid biosynthesis gene into cyanobacteria (Abstracts of the 1995 Annual Meeting of the Japanese Society for Agricultural Chemistry, 41 pages, Haruko Takeyama, Daisuke Takeda, Hideki Nakayama, Kazuyoshi Yazawa, Akiko Yamada, Makoto Matsunaga).

On the other hand, eicosapentaenoic acid is liable to be oxidized and causes problems such as formation of oxides and peroxides and incorporation of fatty acids other than eicosapentaenoic acid. Therefore, development of a new production method is desired. Was.

[0004]

SUMMARY OF THE INVENTION In view of the above circumstances, an object of the present invention is to search for a novel source of eicosapentaenoic acid from the natural world and to provide a method for producing eicosapentaenoic acid.

[0005]

Means for Solving the Problems The present inventors have made intensive studies to solve the above-mentioned problems, and as a result, have found that phloroglucinol eicosapentaenoic acid (eicosapentaenoic acid) contained in brown alga, Phalaenopsis or Ephedra, belonging to the family Aphididae.
ylphloroglucinol) was easily decomposed to eicosapentaenoic acid in an alkali, and the present invention was completed based on this finding.

That is, the present invention is a process for producing eicosapentaenoic acid, comprising obtaining eicosapentaenoic acid by obtaining phloroglucinol eicosapentaenoic acid from brown algae of the family Amidicidae, and hydrolyzing it in an alkali to obtain eicosapentaenoic acid. .

[0007]

DESCRIPTION OF THE PREFERRED EMBODIMENTS The present invention will be described below in detail.
According to the method for producing eicosapentaenoic acid of the present invention, eicosapentaenoic acid phloroglucinol is obtained from brown algae of the family Amidaceae, and hydrolyzed in an alkali to obtain eicosapentaenoic acid. Examples of the brown algae of the family Amidaceae include, but are not limited to, phlebium officinalis and magpie.

Means for obtaining phloroglucinol eicosapentaenoate from brown algae of the family Amidaceae is not particularly limited, and, for example, means for extracting alga bodies with an organic solvent and purifying them by chromatography can be applied. Examples of the organic solvent used here include hexane, benzene, chloroform, acetone, ether, ethyl acetate, ethanol, methanol and the like. As the chromatography, liquid chromatography using silica gel, chemically bonded silica gel, gel filtration agent or the like can be used. The extract may be subjected to the hydrolysis reaction described below without purification by chromatography.

As a means for obtaining eicosapentaenoic acid from phloroglucinol eicosapentaenoate, there may be mentioned a means for hydrolyzing eicosapentaenoic acid phloroglucinol in an alkali and purifying it by chromatography. Examples of the alkali include sodium hydroxide and potassium hydroxide. The pH in the reaction solution is preferably adjusted to 12 to 14 depending on these substances. The reaction solution may or may not be heated. In the case of heating, the temperature is preferably from 40 ° C to 80 ° C, and in this case, the reaction time is preferably from 30 minutes to 5 hours. On the other hand, when no heating is performed, the reaction time is preferably 2 hours to 24 hours.

[0010]

The present invention will be described below with reference to examples, but the present invention is not limited to these examples.

Example 1 100 g of a brown alga of the family Aphididae collected on the coast of Tokushima prefecture was extracted with 500 ml of acetone. After the acetone solution was concentrated, it was partitioned between ethyl acetate and distilled water. After concentrating the ethyl acetate fraction, it was fractionated with a silica gel column (manufactured by Merck, silica gel 60, chloroform: methanol, 9: 1) to obtain 172 mg of phloroglucinol eicosapentaenoate. 10 mg of phloroglucinol eicosapentaenoate and 14.7 mg of sodium hydroxide were dissolved in 1 ml of ethanol and 0.2 ml of distilled water, and left overnight in a dark place. The reaction mixture was added with 5 ml of hexane, washed 3 times with 5 ml of distilled water, concentrated, and purified by a silica gel column (manufactured by Merck, silica gel 60, chloroform: methanol, 9: 1) to a purity of 99% or more (gas 5 mg of eicosapentaenoic acid was obtained.

[Example 2] 100 g of brown algae of the family Amidaceae collected on the coast of Tokushima prefecture was extracted with 500 ml of acetone. After the acetone solution was concentrated, it was partitioned between ethyl acetate and distilled water. After concentrating the ethyl acetate fraction, it was fractionated with a silica gel column (manufactured by Merck, silica gel 60, chloroform: methanol, 9: 1) to obtain 134 mg of phloroglucinol eicosapentaenoate. 10 mg of phloroglucinol eicosapentaenoate and 14.7 mg of sodium hydroxide were dissolved in 1 ml of ethanol and 0.2 ml of distilled water, sealed, and heated at 70 ° C. for 3 hours. After allowing to cool, 5 ml of hexane was added to the reaction solution, washed and concentrated three times with 5 ml of distilled water, and then subjected to a silica gel column (manufactured by Merck, silica gel 60, chloroform: methanol,
9: 1) to obtain 5 mg of eicosapentaenoic acid having a purity of 99% or more (analysis using gas chromatography).

[0013]

According to the present invention, there is provided a novel method for producing eicosapentaenoic acid which is useful as a treatment for arteriosclerosis, a treatment for hyperlipidemia, a dietary supplement, a nutritional additive and the like.

Claims (2)

[Claims] 1. A process for producing eicosapentaenoic acid, comprising obtaining phloroglucinol eicosapentaenoic acid from a brown algae of the family Amidicaceae, and hydrolyzing it in an alkali to obtain eicosapentaenoic acid. 2. The brown algae of the family Amidaceae, comprising:
Or a method for producing eicosapentaenoic acid, which is a giant fork.