IP Library Granted Patent US 9,725,399
Granted Patent B2
US 9,725,399 · App. 14/575,756 · Granted Aug 8, 2017

Lipid comprising long chain polyunsaturated fatty acids

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; NUSEED PTY LTD; GRAINS RESEARCH AND DEVELOPMENT CORPORATION
C07C69/587A23D9/00A61K36/31C11B1/10A61K2236/00
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Quick Facts
Patent No.
US 9,725,399
App. No.
14/575,756
Granted
Aug 8, 2017
Kind
B2
Abstract

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

Claims (84)

1. Extracted plant lipid, comprising fatty acids in an esterified form, the fatty acids comprising oleic acid, palmitic acid, ω6 fatty acids which comprise linoleic acid (LA), ω3 fatty acids which comprise α-linolenic acid (ALA) and docosahexaenoic acid (DHA), and optionally one or more of stearidonic acid (SDA), eicosapentaenoic acid (EPA), docosapentaenoic acid (DPA) and eicosatetraenoic acid (ETA), wherein the level of palmitic acid in the total fatty acid content of the extracted lipid is between 2% and 16%, and wherein the level of myristic acid (C14:0) in the total fatty acid content of the extracted lipid, if present, is less than 1%, and wherein the level of DHA in the total fatty acid content of the extracted lipid is between 20.1% and 35%.

2. The extracted plant lipid of claim 1 which has one or more of the following features

i) the level of palmitic acid in the total fatty acid content of the extracted plant lipid is between 3% and 10%,

ii) the level of myristic acid (C14:0) in the total fatty acid content of the extracted plant lipid is about 0.1%,

iii) the level of oleic acid in the total fatty acid content of the extracted plant lipid is between 1% and 30%,

iv) the level of linoleic acid (LA) in the total fatty acid content of the extracted plant lipid is between 4% and 35%,

v) the level of α-linolenic acid (ALA) in the total fatty acid content of the extracted plant lipid is between 4% and 40%,

vi) the level of γ-linolenic acid (GLA) in the total fatty acid content of the extracted plant lipid is less than 4%,

vii) the level of stearidonic acid (SDA) in the total fatty acid content of the extracted plant lipid is less than 8%,

viii) the level of eicosatetraenoic acid (ETA) in the total fatty acid content of the extracted plant lipid is less than 4%,

ix) a level of eicosatrienoic acid (ETrA) in the total fatty acid content of the extracted plant lipid that is less than 4%,

x) the level of eicosapentaenoic acid (EPA) in the total fatty acid content of the extracted plant lipid is between 4% and 15%,

xi) the level of docosapentaenoic acid (DPA) in the total fatty acid content of the extracted plant lipid is less than 4%,

xii) the level of DHA in the total fatty acid content of the extracted plant lipid is between 21% and 30%,

xiii) the extracted plant lipid comprises ω6-docosapentaenoic acid (22:5 Δ4,7,10,13,16 ) in its fatty acid content,

xiv) the extracted plant lipid comprises less than 0.1% of ω6-docosapentaenoic acid (22:5 Δ4,7,10,13,16 ) in its fatty acid content,

xv) the extracted plant lipid comprises less than 0.1% of one or more or all of SDA, EPA and ETA in its fatty acid content,

xvi) the level of total saturated fatty acids in the total fatty acid content of the extracted plant lipid is between 4% and 25%,

xvii) the level of total monounsaturated fatty acids in the total fatty acid content of the extracted plant lipid is between 4% and 40%,

xviii) the ratio of total ω6 fatty acids:total ω3 fatty acids in the fatty acid content of the extracted plant lipid is between 1.0 and 3.0,

xix) the ratio of new ω6 fatty acids:new ω3 fatty acids in the fatty acid content of the extracted plant lipid is between 0.02 and 1,

xx) the fatty acid composition of the extracted plant lipid is based on an efficiency of conversion of ALA to DHA of at least 24%,

xxi) the total fatty acid in the extracted plant lipid has less than 1.5% C20:1,

xxii) the triacylglycerol (TAG) content of the extracted plant lipid is at least 80%,

xxiii) the extracted plant lipid comprises diacylglycerol (DAG), which DAG comprises DHA,

xxiv) the extracted plant lipid comprises less than 1% free (non-esterified) fatty acids and/or phospholipid,

xxv) at least 70% of the DHA esterified in the form of TAG is in the sn-1 or sn-3 position of the TAG,

xxvi) the most abundant DHA-containing TAG species in the extracted plant lipid is DHA/18:3/18:3 (TAG 58:12), and

xxvii) the lipid comprises tri-DHA TAG (TAG 66:18).

3. The extracted plant lipid of claim 1 , wherein the level of DHA in the total fatty acid content of the extracted plant lipid is between 20.1% and 30%.

4. The extracted plant lipid of claim 1 , wherein the level of oleic acid in the total fatty acid content of the extracted plant lipid is between 30% and 60%.

5. The extracted plant lipid of claim 1 , wherein the level of linoleic acid (LA) in the total fatty acid content of the extracted plant lipid is between 4% and 17%.

6. The extracted plant lipid of claim 1 , wherein the level of α-linolenic acid (ALA) in the total fatty acid content of the extracted plant lipid is between 7% and 40%.

7. The extracted plant lipid of claim 1 , wherein the level of eicosapentaenoic acid (EPA) in the total fatty acid content of the extracted plant lipid is less than 4%.

8. The extracted plant lipid of claim 1 , wherein the level of docosapentaenoic acid (DPA) in the total fatty acid content of the extracted plant lipid is less than 3%.

9. The extracted plant lipid of claim 1 , wherein the level of DHA in the total fatty acid content of the extracted plant lipid is between 20.1% and 25%.

10. The extracted plant lipid of claim 1 , wherein the level of total saturated fatty acids in the total fatty acid content of the extracted plant lipid is between 6% and 12%.

11. The extracted plant lipid of claim 1 , wherein the ratio of total ω6 fatty acids:total ω3 fatty acids in the fatty acid content of the extracted plant lipid is between 0.1 and 1.

12. The extracted plant lipid of claim 1 , wherein at least 80% of the DHA esterified in the form of TAG is in the sn-1 or sn-3 position of the TAG.

13. The extracted plant lipid of claim 1 , wherein

i) the level of oleic acid in the total fatty acid content of the extracted plant lipid is between 1% and 30%,

ii) the level of linoleic acid (LA) in the total fatty acid content of the extracted plant lipid is between 4% and 17%,

iii) the level of α-linolenic acid (ALA) in the total fatty acid content of the extracted plant lipid is between 7% and 40%,

iv) the level of eicosapentaenoic acid (EPA) in the total fatty acid content of the extracted plant lipid is less than 4%,

v) the level of docosapentaenoic acid (DPA) in the total fatty acid content of the extracted plant lipid is less than 3%,

vi) the level of total saturated fatty acids in the total fatty acid content of the extracted plant lipid is between 6% and 12%,

vii) the ratio of total ω6 fatty acids:total ω3 fatty acids in the fatty acid content of the extracted plant lipid is between 0.1 and 1, and

viii) at least 80% of the DHA esterified in the form of TAG is in the sn-1 or sn-3 position of the TAG.

14. The extracted plant lipid of claim 3 , wherein the level of oleic acid in the total fatty acid content of the extracted plant lipid is between 1% and 30%.

15. The extracted plant lipid of claim 3 , wherein the level of linoleic acid (LA) in the total fatty acid content of the extracted plant lipid is between 4% and 17%.

16. The extracted plant lipid of claim 3 , wherein the level of α-linolenic acid (ALA) in the total fatty acid content of the extracted plant lipid is between 7% and 40%.

17. The extracted plant lipid of claim 3 , wherein the level of eicosapentaenoic acid (EPA) in the total fatty acid content of the extracted plant lipid is less than 4%.

18. The extracted plant lipid of claim 3 , wherein the level of docosapentaenoic acid (DPA) in the total fatty acid content of the extracted plant lipid is less than 3%.

19. The extracted plant lipid of claim 3 , wherein the level of DHA in the total fatty acid content of the extracted plant lipid is between 20.1% and 25%.

20. The extracted plant lipid of claim 3 , wherein the level of total saturated fatty acids in the total fatty acid content of the extracted plant lipid is between 6% and 12%.

21. The extracted plant lipid of claim 3 , wherein the ratio of total ω6 fatty acids:total ω3 fatty acids in the fatty acid content of the extracted plant lipid is between 0.1 and 1.

22. The extracted plant lipid of claim 3 , wherein at least 80% of the DHA esterified in the form of TAG is in the sn-1 or sn-3 position of the TAG.

23. The extracted plant lipid of claim 3 , wherein

i) the level of oleic acid in the total fatty acid content of the extracted plant lipid is between 1% and 30%,

ii) the level of linoleic acid (LA) in the total fatty acid content of the extracted plant lipid is between 4% and 17%,

iii) the level of α-linolenic acid (ALA) in the total fatty acid content of the extracted plant lipid is between 7% and 40%,

iv) the level of eicosapentaenoic acid (EPA) in the total fatty acid content of the extracted plant lipid is less than 4%,

v) the level of docosapentaenoic acid (DPA) in the total fatty acid content of the extracted plant lipid is less than 3%,

vi) the level of total saturated fatty acids in the total fatty acid content of the extracted plant lipid is between 6% and 12%,

vii) the ratio of total ω6 fatty acids:total ω3 fatty acids in the fatty acid content of the extracted plant lipid is between 0.1 and 1, and

viii) at least 80% of the DHA esterified in the form of TAG is in the sn-1 or sn-3 position of the TAG.

24. The extracted plant lipid of claim 1 , wherein the level of DHA in the total fatty acid content of the extracted plant lipid is between 30.1% and 35%.

25. The extracted plant lipid of claim 24 , wherein the level of oleic acid in the total fatty acid content of the extracted plant lipid is between 1% and 30%.

26. The extracted plant lipid of claim 24 , wherein the level of linoleic acid (LA) in the total fatty acid content of the extracted plant lipid is between 4% and 17%.

27. The extracted plant lipid of claim 24 , wherein the level of α-linolenic acid (ALA) in the total fatty acid content of the extracted plant lipid is between 7% and 40%.

28. The extracted plant lipid of claim 24 , wherein the level of eicosapentaenoic acid (EPA) in the total fatty acid content of the extracted plant lipid is less than 4%.

29. The extracted plant lipid of claim 24 , wherein the level of docosapentaenoic acid (DPA) in the total fatty acid content of the extracted plant lipid is less than 3%.

30. The extracted plant lipid of claim 24 , wherein the level of total saturated fatty acids in the total fatty acid content of the extracted plant lipid is between 6% and 12%.

31. The extracted plant lipid of claim 24 , wherein the ratio of total ω6 fatty acids: total ω3 fatty acids in the fatty acid content of the extracted plant lipid is between 0.1 and 1.

32. The extracted plant lipid of claim 24 , wherein at least 80% of the DHA esterified in the form of TAG is in the sn-1 or sn-3 position of the TAG.

33. The extracted plant lipid of claim 24 , wherein

i) the level of oleic acid in the total fatty acid content of the extracted plant lipid is between 1% and 30%,

ii) the level of linoleic acid (LA) in the total fatty acid content of the extracted plant lipid is between 4% and 17%,

iii) the level of α-linolenic acid (ALA) in the total fatty acid content of the extracted plant lipid is between 7% and 40%,

iv) the level of eicosapentaenoic acid (EPA) in the total fatty acid content of the extracted plant lipid is less than 4%,

v) the level of docosapentaenoic acid (DPA) in the total fatty acid content of the extracted plant lipid is less than 3%,

vi) the level of total saturated fatty acids in the total fatty acid content of the extracted plant lipid is between 6% and 12%,

vii) the ratio of total ω6 fatty acids:total ω3 fatty acids in the fatty acid content of the extracted plant lipid is between 0.1 and 1, and

viii) at least 80% of the DHA esterified in the form of TAG is in the sn-1 or sn-3 position of the TAG.

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 26, 2017
From: SHESTRA, PUSHKAR; DE FEYTER, ROBERT CHARLES
To: COMMONWEALTH SCIENTIFIC AND INDUSTRIAL RESEARCH ORGANISATION
Reel/Frame 042144/0282 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 26, 2017
From: MCALLISTER, JASON TIMOTHY
To: NUSEED PTY LTD.
Reel/Frame 042144/0289 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 26, 2017
From: DEVINE, MALCOLM DAVID
To: CROOKEDHOLM PARTNERS INC.
Reel/Frame 042144/0292 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 26, 2017
From: CROOKEDHOLM PARTNERS INC.
To: NUFARM AGRICULTURE INC.
Reel/Frame 042144/0295 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 26, 2017
From: NUFARM AGRICULTURE INC.
To: NUSEED PTY LTD.
Reel/Frame 042341/0373 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 14, 2015
From: PETRIE, JAMES ROBERTSON; SINGH, SURINDER PAL
To: COMMONWEALTH SCIENTIFIC AND INDUSTRIAL RESEARCH ORGANISATION
Reel/Frame 036077/0669 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 14, 2015
From: COMMONWEALTH SCIENTIFIC AND INDUSTRIAL RESEARCH ORGANISATION
To: NUSEED PTY LTD; GRAINS RESEARCH AND DEVELOPMENT CORPORATION
Reel/Frame 036077/0722 →
Priority Claims (2)
AU 2013905033 · Dec 18, 2013 · national
AU 2014902471 · Jun 27, 2014 · national
Continuity (1)
Related Publication 20150166928A1 · Jun 18, 2015