IP Library › Granted Patent US 12,442,024
Granted Patent B2
US 12,442,024 · App. 17/359,948 · Granted Oct 14, 2025

Dihomo-gamma-linolenic acid-containing microbial oil/lipid with reduced arachidonic acid content

Inventors: Seizo Sato (Tokyo, JP); Takayoshi Sekiguchi (Tokyo, JP); Misaki Takahashi (Tokyo, JP)
Assignee: Nippon Suisan Kaisha, Ltd.
C12P7/6418A61K31/202A61K45/06C12N1/145C12N9/0071C12R2001/645C12Y114/19003
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 12,442,024
App. No.
17/359,948
Granted
Oct 14, 2025
Kind
B2
Abstract

The purpose of the present invention is to provide an oil/lipid that contains dihomo-γ-linolenic acid at a higher purity. Provided is a microbial oil/lipid that is specified by a high content of dihomo-γ-linolenic acid contained therein and/or a reduced content of undesirable constituting fatty acid(s).

Claims (38)

1. A microbial oil/lipid comprising dihomo-γ-linolenic acid and at least one of C24:0, C22:0, and C20:0 as constituent fatty acids, wherein the microbial oil/lipid comprises (i) dihomo-γ-linolenic acid in a content of greater than 30 wt. %, greater than 32 wt. %, or greater than 34 wt. %; (ii) C24:0, C22:0, and C20:0, in a total content of 12.0 wt. % or less, 11.0 wt. % or less, 10.0 wt. % or less, 9.0 wt. % or less, or 8.0 wt. % or less; and (iii) substantially no arachidonic acid or arachidonic acid in a content of 0.3 wt. % or less, 0.2 wt. % or less, 0.1 wt. % or less, 0.05 wt. % or less, 0.04 wt. % or less, 0.03 wt. % or less, or 0.01 wt. % or less, wherein the microbial oil/lipid comprises no Δ5 desaturase inhibitor.

2. The microbial oil/lipid according to claim 1 , wherein as the constituent fatty acid of the oil, a content of C24:0 is 8.5 wt. % or less, 7.0 wt. % or less, 6.0 wt. % or less, or 5.5 wt. % or less.

3. The microbial oil/lipid according to claim 1 , wherein as the constituent fatty acid of the oil, a total content of C24:0 and C22:0 is 11.0 wt. % or less, 10.0 wt. % or less, 9.0 wt. % or less, 8.0 wt. % or less, or 7.5 wt. % or less.

4. The microbial oil/lipid according to claim 1 , wherein a compositional ratio of arachidonic acid to the dihomo-γ-linolenic acid as the constituent fatty acid of the oil is 1/120 or less, 1/180 or less, 1/360 or less, 1/1000 or less, 1/2350 or less, or 1/3000 or less in terms of weight ratio.

5. The microbial oil/lipid according to claim 4 , wherein a compositional ratio of C24:0 to the dihomo-γ-linolenic acid as the constituent fatty acid of the oil is 1/4.1 or less, 1/5.0 or less, or 1/6.0 or less in terms of weight ratio.

6. The microbial oil/lipid according to claim 4 , wherein a compositional ratio of a total of C24:0 and C22:0 to the dihomo-γ-linolenic acid as the constituent fatty acid of the oil is 1/3.1 or less, 1/4.0 or less, or 1/5.0 or less in terms of weight ratio.

7. The microbial oil/lipid according to claim 4 , wherein a compositional ratio of a total of C24:0, C22:0, and C20:0 to the dihomo-γ-linolenic acid as the constituent fatty acid of the oil is 1/3.0 or less, 1/3.9 or less, or 1/4.8 or less in terms of weight ratio.

8. The microbial oil/lipid according to claim 1 , wherein a compositional ratio of C24:0 to the dihomo-γ-linolenic acid as the constituent fatty acid of the oil is 1/4.1 or less, 1/5.0 or less, or 1/6.0 or less in terms of weight ratio.

9. The microbial oil/lipid according to claim 8 , wherein a compositional ratio of a total of the C24:0 and C22:0 to the dihomo-γ-linolenic acid as the constituent fatty acid of the oil is 1/3.1 or less, 1/4.0 or less, or 1/5.0 or less in terms of weight ratio.

10. The microbial oil/lipid according to claim 8 , wherein a compositional ratio of a total of the C24:0, C22:0, and C20:0 to the dihomo-γ-linolenic acid as the constituent fatty acid of the oil is 1/3.0 or less, 1/3.9 or less, or 1/4.8 or less in terms of weight ratio.

11. The microbial oil/lipid according to claim 1 , wherein a compositional ratio of a total of C24:0 and C22:0 to the dihomo-γ-linolenic acid as the constituent fatty acid of the oil is 1/3.1 or less, 1/4.0 or less, or 1/5.0 or less in terms of weight ratio.

12. The microbial oil/lipid according to claim 11 , wherein a compositional ratio of a total of the C24:0, the C22:0, and C20:0 to the dihomo-γ-linolenic acid as the constituent fatty acid of the oil is 1/3.0 or less, 1/3.9 or less, or 1/4.8 or less in terms of weight ratio.

13. The microbial oil/lipid according to claim 1 , wherein a compositional ratio of a total of C24:0, C22:0, and C20:0 to the dihomo-γ-linolenic acid as the constituent fatty acid of the oil is 1/3.0 or less, 1/3.9 or less, or 1/4.8 or less in terms of weight ratio.

14. The microbial oil/lipid according claim 1 , wherein the microbial oil/lipid is an oil derived from a filamentous fungus.

15. The microbial oil/lipid according to claim 14 , wherein the filamentous fungus belongs to genus Mortierella.

16. A microbial oil/lipid comprising the microbial oil/lipid described in claim 1 , wherein the microbial oil/lipid is a crude oil.

17. A pharmaceutical composition comprising the microbial oil/lipid described in claim 1 .

18. An anti-allergic agent or an anti-inflammatory agent comprising the microbial oil/lipid described in claim 1 .

19. A lower alcohol ester composition or a free fatty acid composition comprising dihomo-γ-linolenic acid, obtained or obtainable by a method comprising providing the microbial oil/lipid described in claim 1 to an ester exchange reaction or a hydrolysis reaction.

20. The composition according to claim 19 , comprising the dihomo-γ-linolenic acid in a content of greater than 30 wt. %, greater than 32 wt. %, or greater than 34 wt. %.

21. The composition according to claim 19 , comprising substantially no arachidonic acid or comprising arachidonic acid in a content of 0.3 wt. % or less, 0.2 wt. % or less, 0.1 wt. % or less, 0.05 wt. % or less, 0.04 wt. % or less, 0.03 wt. % or less, or 0.01 wt. % or less.

22. The composition according to claim 19 , wherein a content of C24:0 is 8.5 wt. % or less, 7.0 wt. % or less, 6.0 wt. % or less, or 5.5 wt. % or less.

23. The composition according to claim 19 , wherein a total content of C24:0 and C22:0 is 11.0 wt. % or less, 10.0 wt. % or less, 9.0 wt. % or less, 8.0 wt. % or less, or 7.5 wt. % or less.

24. The composition according to claim 19 , wherein a total content of C24:0, C22:0, and C20:0 is 12.0 wt. % or less, 11.0 wt. % or less, 10.0 wt. % or less, 9.0 wt. % or less, or 8.0 wt. % or less.

25. The composition according to claim 19 , wherein a compositional ratio of arachidonic acid to the dihomo-γ-linolenic acid as a constituent fatty acid of an oil is 1/120 or less, 1/180 or less, 1/360 or less, 1/1000 or less, 1/2350 or less, or 1/3000 or less in terms of weight ratio.

26. The composition according to claim 19 , wherein a compositional ratio of C24:0 to the dihomo-γ-linolenic acid as a constituent fatty acid of an oil is 1/4.1 or less, 1/5.0 or less, or 1/6.0 or less in terms of weight ratio.

27. The composition according to claim 19 , wherein a compositional ratio of a total of C24:0 and C22:0 to the dihomo-γ-linolenic acid as a constituent fatty acid of an oil is 1/3.1 or less, 1/4.0 or less, or 1/5.0 or less in terms of weight ratio.

28. The composition according to claim 19 , wherein a compositional ratio of a total of C24:0, C22:0, and C20:0 to the dihomo-γ-linolenic acid as a constituent fatty acid of an oil is 1/3.0 or less, 1/3.9 or less, or 1/4.8 or less in terms of weight ratio.

29. A microbial biomass comprising the microbial oil/lipid described in claim 1 .

30. A foodstuff, a supplement, a medicament, a cosmetic, or an animal feed comprising the microbial biomass described in claim 29 .

31. A culture comprising the microbial biomass described in claim 29 .

32. The culture according to claim 31 , comprising the microbial oil/lipid in a content of 0.4 g/liter or greater.

33. A method of producing the microbial oil/lipid according to claim 1 , the method comprising culturing, in a culture medium, a microorganism strain having a mutation in a Δ5 desaturase gene to produce the dihomo-γ-linolenic acid-containing microbial oil/lipid.

34. The method according to claim 33 , wherein the microorganism strain has a gene mutation that results in an amino acid substitution of Y310C of SEQ ID NO: 3 of a Δ5 desaturase.

35. The method according to claim 33 , wherein the microorganism strain has a base deletion at positions from 2206 to 2234 of SEQ ID NO: 1 of the Δ5 desaturase gene.

36. The method according to claim 33 , wherein the microorganism strain belongs to genus Mortierella.

37. The method according to claim 33 , wherein the microorganism strain is a microorganism deposited under accession number NITE BP-02778.

38. A microorganism having deposited under accession number NITE BP-02778.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 13, 2021
From: SATO, SEIZO; SEKIGUCHI, TAKAYOSHI; TAKAHASHI, MISAKI
To: NIPPON SUISAN KAISHA, LTD.
Reel/Frame 056833/0492 →
Priority Claims (1)
JP 2018-248464 · Dec 28, 2018 · national
Continuity (2)
Continuation In Part PCTJP2019051565 · Dec 27, 2019
Related Publication 20210324433A1 · Oct 21, 2021
References Cited (28)
US 4782025A · Inoue · 1988 [cited by examiner]
US 6280982B1 · Kawashima et al. · 2001 [cited by applicant]
US 6805859B2 · Imada · 2004 [cited by examiner]
US 7094592B2 · Watanabe · 2006 [cited by examiner]
US 9820484B2 · Sato · 2017 [cited by examiner]
US 11491118B2 · Hetherington · 2022 [cited by examiner]
US 20080020124A1 · Kawashima et al. · 2008 [cited by applicant]
US 20080108699A1 · Tateishi et al. · 2008 [cited by applicant]
US 20100167359A1 · Katano et al. · 2010 [cited by applicant]
US 20160317592A1 · Yamaguchi et al. · 2016 [cited by applicant]
JP H0591887A · 1993 [cited by applicant]
JP 2017502114A · 2017 [cited by applicant]
WO WO2005083101A1 · 2005 [cited by applicant]
WO WO2006085687A1 · 2006 [cited by applicant]
WO WO2008087921A1 · 2008 [cited by applicant]
WO WO2009022323A1 · 2009 [cited by applicant]
WO WO2011154947A2 · 2011 [cited by applicant]
WO WO2015083806A1 · 2015 [cited by applicant]
WO WO2015083843A2 · 2015 [cited by applicant]
Extended European Search Report issued Aug. 31, 2022 in European Patent Application No. 19903896.9. [cited by applicant]
“Product specification sheet cis-8, 1 1,14-Eicosatrienoic acid= 99%”, Retrieved from the Internet: URL:https://www.sigmaaldrich.com/specification-sheets/395/818/E4504-BULK SIGMA .pdf [retrieved on Aug. 17, 2022]. [cited by applicant]
“Product specification sheet cis-, 1 1, 14-Eicosatrienoic acid methyl ester=99%”, Retrieved from the Internet: URL:https://www.sigmaaldrich.com/specification-sheets/1 15/574/E351 1-BULKSIGMA _.pdf [retrieved on Aug. 17,… [cited by applicant]
Abe et al., “Identification of Mutation Sites on Δ5 Desaturase Genes from [cited by applicant]
Jareonkitmongkol et al., “Fatty acid desaturation-defective mutants of an arachidonic-acid-producing fungus, [cited by applicant]
Kawashima et al., “Industrial Production of Dihomo-γ-linolenic Acid by a Δ5 Desaturase-defective Mutant of [cited by applicant]
Jareonkitmongkol et al., “A Novel Δ5-Desaturase-Defective Mutant of [cited by applicant]
Kikukawa et al., “Microbial production of dihomo-γ-linolenic acid by Δ5-desaturase gene-disruptants of [cited by applicant]
International Search Report mailed Apr. 7, 2020 in PCT/JP2019/051565. [cited by applicant]