Dihomo-γ-linolenic acid-containing microbial oil and dihomo-γ-linolenic acid-containing microbial biomass

Patent metadata

Field	Value
Publication number	US-9820484-B2
Application number	US-201415101581-A
Country	US
Kind code	B2
Filing date	Dec 4, 2014
Priority date	Dec 4, 2013
Publication date	Nov 21, 2017
Grant date	Nov 21, 2017

Abstract

A microbial oil comprising dihomo-γ-linolenic acid as a constituent fatty acid of an oil, the microbial oil has a content, in terms of a weight ratio of arachidonic acid relative to dihomo-γ-linolenic acid (arachidonic acid/dihomo-γ-linolenic acid) of less than 1/13. Preferably, the microbial oil has a triglyceride content of greater than or equal to 70% by weight, and a saturated fatty acid content of less than or equal to 40% by weight. Moreover, a lower alcohol ester of dihomo-γ-linolenic acid or a free fatty acid of dihomo-γ-linolenic acid obtained from the microbial oil is provided.

First claim

The invention claimed is:

1. A microbial oil recovered from a cultured microbial biomass wherein said microbial oil comprises dihomo-γ-linolenic acid as a constituent fatty acid of the oil, the microbial oil having a weight ratio of arachidonic acid (ARA) relative to dihomo-γ-linolenic acid (DGLA) ARA:DGLA) of less than 1/20, wherein said microbial oil is obtained from a microbe grown in a culture medium containing a Δ5 desaturase inhibitor, or is obtained from a microbe that is mutated to have a reduced or lost Δ5 desaturase enzyme activity, or is obtained from the microbe that is mutated to have a reduced or lost Δ5 desaturase enzyme activity that is cultured in the presence of a Δ5 desaturase inhibitor.

2. The microbial oil according to claim 1 , wherein said weight ratio is less than or equal to 1/30.

3. The microbial oil according to claim 1 , wherein the microbial oil has a triglyceride content of greater than or equal to 70% by weight.

4. The microbial oil according to claim 3 having a triglyceride content of greater than or equal to 90% by weight.

5. The microbial oil according claim 3 , wherein the microbial oil is a crude oil, and wherein the triglyceride content is greater than or equal to 90% by weight and said weight ratio of arachidonic acid relative to dihomo-γ-linolenic acid is less than or equal to 1/20.

6. The microbial oil according to claim 3 , wherein the microbial oil is a refined oil, wherein the triglyceride content is greater than or equal to 90% by weight and said weight ratio of arachidonic acid relative to dihomo-γ-linotenic acid is less than or equal to 1/30.

7. The microbial oil according to claim 1 , containing phospholipid at from 0.1 to 10% by weight.

8. The microbial oil according to claim 1 , wherein the microbial oil has a saturated fatty acid content of less than or equal to 40% by weight.

9. A lower alcohol ester composition comprising dihomo-γ-linolenic acid ester, or a free fatty acid composition comprising dihomo-γ-linolenic acid, in which a weight ratio of arachidonic acid relative to dihomo-γ-linolenic acid (arachidonic acid/dihomo-γ-linolenic acid) is less than 1/20.
produced or obtainable by a method comprising subjecting a microbial oil according to claim 1 to an ester exchange reaction or hydrolysis reaction.

10. The lower alcohol ester composition or the free fatty acid composition according to claim 9 , wherein the arachidonic acid content is less than or equal to 7% by weight.

11. The lower alcohol ester composition or the free fatty acid composition according to claim 9 , wherein the composition is foodstuffs, dietary supplements, medicaments, cosmetics, or animal feed.

12. The microbial oil according to claim 1 , wherein the arachidonic acid content is less than or equal to 7% by weight.

13. The microbial oil according to claim 1 , wherein the composition is foodstuffs, dietary supplements, medicaments, cosmetics, or animal feed.

14. A microbial biomass containing the microbial oil according to claim 1 .

15. A liquid culture medium containing the microbial biomass according to claim 14 .

16. The liquid culture medium according to claim 15 , wherein a content of the microbial biomass is greater than or equal to 2.5 g/L, in terms of dry weight of the microbial biomass.

17. The liquid culture medium according to claim 15 , wherein the liquid culture medium contains the microbial oil at a content of 0.4 g/L or greater.

18. A lower alcohol ester composition derived from a microbial oil and comprising dihomo-γ-linolenic acid ester, or a free fatty acid composition derived from a microbial oil and comprising dihomo-γ-linolenic acid, in which a weight ratio of arachidonic acid relative to dihomo-γ-linolenic acid (arachidonic acid/dihomo-γ-linolenic acid) is less than 1/20 wherein said microbial oil is obtained from a microbe grown in a culture medium containing a Δ5 desaturase inhibitor, or is obtained from a microbe that is mutated to have a reduced or lost Δ5 desaturase enzyme activity, or is obtained from the microbe that is mutated to have a reduced or lost Δ5 desaturase enzyme activity that is cultured in the presence of a Δ5 desaturase inhibitor.

19. A method of producing a lower alcohol ester composition or free fatty acid composition according to claim 9 , from the microbial oil the method comprising:
(a) subjecting a microbial oil to an ester exchange reaction or a hydrolysis reaction, to obtain dihomo-γ-linolenic acid ester, or a free fatty acid composition comprising, dihomo-γ-linolenic acid, wherein said microbial oil comprises dihomo-γ-linolenic acid as a constituent fatty acid of the oil, the microbial oil having weight ratio of arachidonic acid relative to dihomo-γ-linolenic acid (arachidonic acid/dihomo-γ-linolenic acid) of less than 1/20;
(b) obtaining a mixture of free fatty acids or lower alcohol esters of fatty acids by hydrolysis or alcoholysis of the microbial oil, and
(c) rectifying the mixture of free fatty acids or lower alcohol esters to obtain a free fatty acid or lower alcohol ester composition in which the fatty acids have at least 20 carbon atoms.

20. The method of producing a lower alcohol dihomo-γ-linolenic acid ester or free dihomo-γ-linolenic acid comprising producing a lower alcohol ester composition or free fatty acid composition in accordance with according to claim 19 , further comprising:
(d) performing fractionation and purification of the lower alcohol ester of dihomo-γ-linolenic acid or of dihomo-γ-linolenic acid, by reverse phase distribution type column chromatography, from the free fatty acid or lower alcohol ester composition in which the fatty acids have at least 20 carbon atoms.

Assignees

• Nippon Suisan Kaisha Ltd

Inventors

• Sato Seizo
• Fukae Takuro
• Ohtsuka Naomi
• Yamaguchi Hideaki
• Ikeda Rie

Classifications

• A61P37/08

  Antiallergic agents (antiasthmatic agents A61P11/06; ophthalmic antiallergics A61P27/14) · CPC title

• A61P37/06

  Immunosuppressants, e.g. drugs for graft rejection · CPC title

• A61P39/00

  General protective or antinoxious agents · CPC title

• A61P29/00

  Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID] · CPC title

• A61P17/04

  Antipruritics · CPC title