IP Library Granted Patent US 11,623,911
Granted Patent B2
US 11,623,911 · App. 16/146,469 · Granted Apr 11, 2023

Lipid comprising docosapentaenoic acid

Inventors: James Robertson Petrie (Goulburn, AU); Surinder Pal Singh (Downer, AU); Pushkar Shrestha (Lawson, AU); Jason Timothy McAllister (Portarlington, AU); Robert Charles de Feyter (Monash, AU); Malcolm David Devine (Vernon, CA)
Assignees: COMMONWEALTH SCIENTIFIC AND INDUSTRIAL RESEARCH ORGANISATION; GRAINS RESEARCH AND DEVELOPMENT CORPORATION; NUSEED NUTRITIONAL AUSTRALIA PTY LTD.
C07C69/587A23D9/00A61K31/20A61K31/201A61K31/202A61K36/31C11B1/10C12N15/8247A61K2236/00A61K2236/333
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Quick Facts
Patent No.
US 11,623,911
App. No.
16/146,469
Granted
Apr 11, 2023
Kind
B2
Abstract

The present invention relates to extracted plant lipid or microbial lipid comprising docosapentaenoic acid, and processes for producing the extracted lipid.

Claims (50)

1. Brassica napus seedoil, comprising fatty acids in an esterified form, the fatty acids comprising oleic acid, palmitic acid, ω6 polyunsaturated fatty acids which comprise linoleic acid (LA), ω3 polyunsaturated fatty acids which comprise α-linolenic acid (ALA), eicosapentaenoic acid (EPA), docosapentaenoic acid (DPA), docosahexaenoic acid (DHA), stearidonic acid (SDA) and eicosatetraenoic acid (ETA), wherein the level of palmitic acid in the total fatty acid content of the seedoil is between 2% and 16% by weight, wherein myristic acid (C14:0) is either absent or is present in the seedoil at a level of less than 1% by weight of the total fatty acid content of the seedoil, and wherein the level of EPA in the total fatty acid content of the seedoil is between 4% and 15% by weight.

2. The seedoil of claim 1 , wherein a level of γ-linolenic acid (GLA) of less than 4% by weight is present in the total fatty acid content of the seedoil.

3. The seedoil of claim 2 , wherein at least 70% of the DPA esterified in the form of triacylglycerols (TAG) in the seedoil is in the sn-1 or sn-3 position of the TAG.

4. The seedoil of claim 2 , wherein at least 80% of the DPA esterified in the form of TAG in the seedoil is in the sn-1 or sn-3 position of the TAG.

5. The seedoil of claim 2 , wherein the level of docosahexaenoic acid (DHA) in the total fatty acid content of the seedoil is less than 0.5% by weight.

6. The seedoil of claim 2 , wherein the level of docosahexaenoic acid (DHA) in the total fatty acid content of the seedoil is less than 2% by weight.

7. The seedoil of claim 2 , wherein the level of docosahexaenoic acid (DHA) in the total fatty acid content of the seedoil is between 0.5% and 2.0% by weight.

8. The seedoil of claim 7 , wherein at least 70% of the DHA esterified in the form of triacylglycerols (TAG) in the seedoil is in the sn-1 or sn-3 position of the TAG.

9. The seedoil of claim 2 , wherein the level of docosapentaenoic acid (DPA) in the total fatty acid content of the seedoil is between 0.05% and 8% by weight.

10. The seedoil of claim 9 , wherein at least 70% of the DPA esterified in the form of triacylglycerols (TAG) in the seedoil is in the sn-1 or sn-3 position of the TAG.

11. The seedoil of claim 3 , which has the following features

i) the level of oleic acid in the total fatty acid content of the seedoil is between 1% and 60% by weight,

ii) the level of linoleic acid (LA) in the total fatty acid content of the seedoil is between 4% and 35% by weight,

iii) a level of γ-linolenic acid (GLA) of less than 4% by weight is present in the total fatty acid content of the seedoil, and

iv) a level of total saturated fatty acids of between 4% and 25% by weight is present in the total fatty acid content of the seedoil.

12. The seedoil of claim 10 , wherein the level of docosahexaenoic acid (DHA) in the total fatty acid content of the seedoil is between 0.5% and 2.0% by weight.

13. Brassica napus seedoil, comprising fatty acids in an esterified form, the fatty acids comprising oleic acid, palmitic acid, ω6 polyunsaturated fatty acids which comprise linoleic acid (LA), ω3 polyunsaturated fatty acids which comprise α-linolenic acid (ALA), eicosapentaenoic acid (EPA), docosapentaenoic acid (DPA), docosahexaenoic acid (DHA), stearidonic acid (SDA) and eicosatetraenoic acid (ETA), wherein the level of palmitic acid in the total fatty acid content of the seedoil is between 2% and 16% by weight, wherein the level of myristic acid (C14:0) is either absent or is present in the seedoil at a level of less than 1% by weight of the total fatty acid content of the seedoil, and wherein the level of DPA in the total fatty acid content of the seedoil is greater than the level of DHA.

14. The seedoil of claim 13 , wherein the level of DPA in the total fatty acid content of the seedoil is about 2.5% by weight.

15. The seedoil of claim 13 , wherein the level of DPA in the total fatty acid content of the seedoil is about 3.9% by weight and the level of DHA is about 1.2% by weight.

16. The seedoil of claim 13 , wherein the level of DPA in the total fatty acid content of the seedoil is about 3.0% by weight and the level of DHA is about 0.8% by weight.

17. The seedoil of claim 13 , wherein a level of γ-linolenic acid (GLA) of less than 4% by weight is present in the total fatty acid content of the seedoil.

18. The seedoil of claim 17 , wherein at least 70% of the DPA esterified in the form of triacylglycerols (TAG) in the seedoil is in the sn-1 or sn-3 position of the TAG.

19. The seedoil of claim 17 , wherein at least 80% of the DPA esterified in the form of TAG in the seedoil is in the sn-1 or sn-3 position of the TAG.

20. The seedoil of claim 17 , wherein the level of docosahexaenoic acid (DHA) in the total fatty acid content of the seedoil is less than 0.5% by weight.

21. The seedoil of claim 17 , wherein the level of docosahexaenoic acid (DHA) in the total fatty acid content of the seedoil is less than 2% by weight.

22. The seedoil of claim 17 , wherein the level of docosahexaenoic acid (DHA) in the total fatty acid content of the seedoil is between 0.5% and 2.0% by weight.

23. The seedoil of claim 22 , wherein at least 70% of the DHA esterified in the form of triacylglycerols (TAG) in the seedoil is in the sn-1 or sn-3 position of the TAG.

24. The seedoil of claim 17 , wherein the level of docosapentaenoic acid (DPA) in the total fatty acid content of the seedoil is between 0.05% and 8% by weight.

25. The seedoil of claim 24 , wherein at least 70% of the DPA esterified in the form of triacylglycerols (TAG) in the seedoil is in the sn-1 or sn-3 position of the TAG.

26. The seedoil of claim 18 , which has the following features

i) the level of oleic acid in the total fatty acid content of the seedoil is between 1% and 60% by weight,

ii) the level of linoleic acid (LA) in the total fatty acid content of the seedoil is between 4% and 35% by weight,

iii) a level of γ-linolenic acid (GLA) of less than 4% by weight is present in the total fatty acid content of the seedoil, and

iv) a level of total saturated fatty acids of between 4% and 25% by weight is present in the total fatty acid content of the seedoil.

27. The seedoil of claim 25 , wherein the level of docosahexaenoic acid (DHA) in the total fatty acid content of the seedoil is between 0.5% and 2.0% by weight.

28. Brassica napus seedoil, comprising a total fatty acid content which comprises fatty acids in an esterified polyunsaturated fatty acids which comprise linoleic acid (LA), ω3 polyunsaturated fatty acids which comprise α-linolenic acid (ALA), eicosapentaenoic acid (EPA), docosapentaenoic acid (DPA), docosahexaenoic acid (DHA), stearidonic acid (SDA) and eicosatetraenoic acid (ETA), wherein the level of palmitic acid in the total fatty acid content of the seedoil is between 2% and 16% by weight, wherein myristic acid (C14:0) is either absent or is present in the seedoil at a level of less than 1% by weight of the total fatty acid content of the seedoil, wherein at least 70% of the DPA esterified in the form of triacylglycerols (TAG) in the seedoil is in the sn-1 or sn-3 position of the TAG, and wherein ALA, SDA, ETA, EPA, DPA, DHA and eicosatrienoic acid (ETrA) are each present at a level in the total fatty acid content, each level being expressed as a percentage of the total fatty acid content, whereby the sum of the percentages for DPA and DHA divided by the sum of the percentages for ALA, SDA, ETA, EPA, DPA, DHA and ETrA, expressed as a percentage, is between 15.3% and 60.5%.

29. The seedoil of claim 28 , wherein the sum of the percentages for DPA and DHA divided by the sum of the percentages for ALA, SDA, ETA, EPA, DPA, DHA and ETrA, expressed as a percentage, is between 17% and 55%.

30. The seedoil of claim 28 , wherein the sum of the percentages for DPA and DHA divided by the sum of the percentages for ALA, SDA, ETA, EPA, DPA, DHA and ETrA, expressed as a percentage, is between 15.3% and 18.7%.

31. The seedoil of claim 28 , wherein a level of γ-linolenic acid (GLA) of less than 4% by weight is present in the total fatty acid content of the seedoil.

32. The seedoil of claim 28 , wherein at least 80% of the DPA esterified in the form of TAG in the seedoil is in the sn-1 or sn-3 position of the TAG.

33. The seedoil of claim 28 , which has the following features

i) the level of oleic acid in the total fatty acid content of the seedoil is between 1% and 60% by weight,

ii) the level of linoleic acid (LA) in the total fatty acid content of the seedoil is between 4% and 35% by weight,

iii) a level of γ-linolenic acid (GLA) of less than 4% by weight is present in the total fatty acid content of the seedoil, and

iv) a level of total saturated fatty acids of between 4% and 25% by weight is present in the total fatty acid content of the seedoil.

34. The seedoil of claim 28 , wherein the seedoil was obtained from Brassica napus seed harvested from a population of at least 1,000 Brassica napus plants grown in a field.

35. The seedoil of claim 28 , wherein the level of EPA in the total fatty acid content of the seedoil is between 0.05% and 10% by weight.

36. The seedoil of claim 28 , wherein the level of DPA in the total fatty acid content of the seedoil is about 2.5% by weight.

37. The seedoil of claim 28 , wherein the level of DPA in the total fatty acid content of the seedoil is about 3.9% by weight and the level of DHA is about 1.2% by weight.

38. The seedoil of claim 28 , wherein the level of DPA in the total fatty acid content of the seedoil is about 3.0% by weight and the level of DHA is about 0.8% by weight.

Assignments (8)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 29, 2021
From: NUSEED PROPRIETARY LIMITED
To: NUSEED NUTRITIONAL AUSTRALIA PTY LTD
Reel/Frame 057019/0923 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 2, 2020
From: COMMONWEALTH SCIENTIFIC AND INDUSTRIAL RESEARCH ORGANISATION
To: COMMONWEALTH SCIENTIFIC AND INDUSTRIAL RESEARCH ORGANISATION; NUSEED PTY LTD; GRAINS RESEARCH AND DEVELOPMENT CORPORATION
Reel/Frame 052295/0162 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 2, 2020
From: SHRESTHA, PUSHKAR; DE FEYTER, ROBERT CHARLES
To: COMMONWEALTH SCIENTIFIC AND INDUSTRIAL RESEARCH ORGANISATION
Reel/Frame 052295/0202 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 2, 2020
From: MCALLISTER, JASON TIMOTHY
To: NUSEED PTY LTD
Reel/Frame 052295/0271 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 2, 2020
From: PETRIE, JAMES ROBERTSON; SINGH, SURINDER PAL
To: COMMONWEALTH SCIENTIFIC AND INDUSTRIAL RESEARCH ORGANISATION
Reel/Frame 052294/0889 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 2, 2020
From: CROOKEDHOLM PARTNERS INC.
To: NUFARM AGRICULTURE INC.
Reel/Frame 052296/0390 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 2, 2020
From: NUFARM AGRICULTURE INC.
To: NUSEED PTY LTD
Reel/Frame 052296/0491 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 2, 2020
From: DEVINE, MALCOLM DAVID
To: CROOKEDHOLM PARTNERS INC.
Reel/Frame 052295/0298 →
Priority Claims (2)
AU 2014902471 · Jun 27, 2014 · national
AR 20140104761 · Dec 18, 2014 · national
Continuity (5)
Continuation 15617642 · Jun 8, 2017
Continuation 14743531 · Jun 18, 2015
Continuation In Part PCTAU2014050433 · Dec 18, 2014
Continuation In Part 14575756 · Dec 18, 2014
Related Publication 20190194572A1 · Jun 27, 2019
Cited By (1)
US 12,529,007