IP Library Granted Patent US 9,550,718
Granted Patent B2
US 9,550,718 · App. 14/464,510 · Granted Jan 24, 2017

Lipid comprising polyunsaturated fatty acids

Inventors: James Robertson Petrie (Goulburn, AU); Surinder Pal Singh (Downer, AU); Robert Charles de Feyter (Monash, AU)
Assignees: COMMONWEALTH SCIENTIFIC AND INDUSTRIAL RESEARCH ORGANISATION; GRAINS RESEARCH AND DEVELOPMENT CORPORATION; NUSEED PTY LTD
C07C67/02A23L33/12C11B1/00C11B1/10C11C3/00C11C3/003C11C3/06
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Quick Facts
Patent No.
US 9,550,718
App. No.
14/464,510
Granted
Jan 24, 2017
Kind
B2
Abstract

The present invention relates to extracted plant lipid, comprising fatty acids in an esterified form.

Claims (78)

1. Extracted lipid from Brassica or Aradidopsis seeds, whose total fatty acid content comprises

(a) a total monounsaturated fatty acid content which comprises oleic acid,

(b) a total saturated fatty acid content which comprises palmitic acid and, if present, myristic acid (C14:0),

(c) a total ω6 fatty acid content which comprises linoleic acid (LA),

(d) a ω3 fatty acid content,

(e) less than 1% myristic acid (C14:0), and

(f) less than 4% eicosatrienoic acid (ETrA),

wherein

(i) a level of DHA between 7% and 20% is present in the total fatty acid content of the extracted lipid, wherein at least 70% of the DHA is esterified at the sn-1 or sn-3 position of triacylglycerol (TAG),

(ii) a level of palmitic acid between 2% and 16% is present in the total fatty acid content of the extracted lipid,

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

(iv) the total saturated fatty acid content of the extracted lipid is between 4% and 25% of the total fatty acid content,

(v) the ratio of the total ω6 fatty acid content to the ω3 fatty acid content in total of the extracted lipid is between 0.1 and 3.0, and

(vi) at least 70% of the total fatty acid content of the extracted lipid is esterified in the form of TAG.

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

i) a level of palmitic acid between 2% and 15% is present in the total fatty acid content of the extracted lipid,

ii) a level of eicosatrienoic acid (ETrA) between 0.05% and about 2% is present in the total fatty acid content of the extracted lipid,

iii) the extracted lipid has a level of SPA of less than about 0.1%, EPA of less than about 0.1%, and ETA of less than about 0.1% in its total fatty acid content,

iv) the total monounsaturated fatty acid content in the extracted lipid is between about 4% and about 35% of the total fatty acid content,

v) the extracted lipid comprises new ω6 fatty acids in the total ω6 fatty acid content, wherein the level of new ω6 fatty acids in the extracted lipid is less than about 10% of the total fatty acid content,

vi) the ω3 fatty acid content in total in the extracted lipid is between 36% and about 65% of the total fatty acid content,

vii) the ratio of the total ω6 fatty acid content to the ω3 fatty acid content in total in the extracted lipid is between about 0.1 and about 0.5,

viii) the extracted lipid comprises new ω3 fatty acids in the ω3 fatty acid content in total and new ω6 fatty acids in the total ω6 fatty acid content, wherein the ratio of the new ω6 fatty acids to the new ω3 fatty acids in the fatty acid content of the extracted lipid is between about 0.1 and about 1,

ix) the extracted lipid has a fatty acid composition based on an efficiency of conversion of oleic acid to DHA of at least about 10%,

x) the extracted lipid has a fatty acid composition based on an efficiency of conversion of LA to DHA of at least about 15%,

xi) the extracted lipid has a fatty acid composition based on an efficiency of conversion of ALA to DHA of at least about 17%,

xii) the total fatty acid content in the extracted lipid has less than 1% C20:1,

xiii) at least about 80% of the total fatty acid content of the extracted lipid is esterified in the form of TAG,

xiv) the extracted lipid comprises diacylglycerol (DAG), and

xv) the extracted lipid comprises less than about 10% free (non-esterified) fatty acids and/or phospholipid.

3. The extracted lipid of claim 1 which is in the form of an oil, wherein the oil comprises one or more sterols.

4. The extracted lipid of claim 3 , wherein the oil comprises less than 10 mg of sterols/g of oil.

5. The extracted lipid of claim 3 , wherein the oil comprises one or more or all of campesterol, Δ5-stigmasterol, eburicol, β-sitosterol, Δ5-avenasterol, Δ7-stigmasterol and Δ7-avenasterol.

6. The extracted lipid of claim 1 , which is from canola seed.

7. The extracted lipid of claim 1 , wherein a level of linoleic acid between 4% and about 20% is present in the total fatty acid content of the extracted lipid.

8. The extracted lipid of claim 1 , wherein a level of α-linolenic acid (ALA) between about 10% and about 35% is present in the total fatty acid content of the extracted lipid.

9. The extracted lipid of claim 1 , wherein a level of α-linolenic acid (ALA) between about 2% and about 16% is present in the total fatty acid content of the extracted lipid.

10. The extracted lipid of claim 1 , wherein a level of γ-linolenic acid (GLA) less than 4% is present in the total fatty acid content of the extracted lipid.

11. The extracted lipid of claim 1 , wherein a level of stearidonic acid (SDA) between 0.05% and about 7% is present in the total fatty acid content of the extracted lipid.

12. The extracted lipid of claim 1 , wherein a level of eicosatetraenoic acid (ETA) between 0.05% and about 4% is present in the total fatty acid content of the extracted lipid.

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

14. The extracted lipid of claim 1 , wherein a level of docosapentaenoic acid (DPA) between 0.05% and 8% is present in the total fatty acid content of the extracted lipid.

15. The extracted lipid of claim 1 , wherein a level of DHA between about 10% and 20% is present in the total fatty acid content of the extracted lipid.

16. The extracted lipid of claim 1 , wherein a level of DHA between about 11% and 20% is present in the total fatty acid content of the extracted lipid.

17. The extracted lipid of claim 1 , wherein the extracted lipid comprises less than about 0.1% ω6-docosapentaenoic acid (22:5 Δ4, 7, 10, 13, 16 ) in its total fatty acid content.

18. The extracted lipid of claim 1 , wherein the total saturated fatty acid content in the extracted lipid is between about 4% and about 20% of the total fatty acid content.

19. The extracted lipid of claim 1 , wherein the total monounsaturated fatty acid content in the extracted lipid is between about 4% and about 35% of the total fatty acid content.

20. The extracted lipid of claim 1 , wherein the extracted lipid comprises a total polyunsaturated fatty acid content comprising the total ω6 fatty acid content and the ω3 fatty acid content in total, wherein the total polyunsaturated fatty acid content in the extracted lipid is between about 20 and about 75% of the total fatty acid content.

21. The extracted lipid of claim 1 , wherein the extracted plant lipid comprises new ω3 fatty acids in the ω3 fatty acid content in total, wherein the level of new ω3 fatty acids in the extracted lipid is between 9% and about 33% of the total fatty acid content.

22. The extracted 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.

23. The extracted lipid of claim 1 , wherein the most abundant DHA-containing TAG species in the lipid is DNA/18:3/18:3 (TAG 58:12).

24. The extracted lipid of claim 1 , wherein the extracted lipid comprises tri-DHA TAG (TAG 66:18).

25. The extracted lipid of claim 1 , which comprises ω6-docosapentaenoic acid (22:5 Δ4, 7, 10, 13, 16 ) in its total fatty acid content.

26. The extracted lipid of claim 1 , wherein the total ω6 fatty acid content in the extracted lipid is less than 20% of the total fatty acid content.

27. The extracted lipid of claim 1 , wherein a level of about 1% C20:1 is present in the total fatty acid content in the extracted lipid.

28. Extracted lipid from Brassica seeds, whose total fatty acid content comprises

(a) a total monounsaturated fatty acid ent which comprises oleic acid,

(b) a total saturated fatty acid content which comprises palmitic acid and, if present, myristic acid (C14:0),

(c) a total ω6 fatty acid content which comprises linoleic acid (LA),

(d) a ω3 fatty acid content,

(e) less than 1% myristic acid (C14:0), and

(f) less than 4% eicosatrienoic acid (ETrA),

wherein

(i) a level of DHA of about 3%, about 4%, about 5% or about 6% is present in the total fatty acid content of the extracted lipid, wherein at least 70% of the DHA is esterified at the sn-1 or sn-3 position of triacylglycerol (TAG),

(ii) a level of palmitic acid between 2% and 16% is present in the total fatty acid content of the extracted lipid,

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

(iv) the total saturated fatty acid content of the extracted lipid is between 4% and 25% of the total fatty acid content,

(v) the ratio of the total ω6 fatty acid content to the ω3 fatty acid content in total of the extracted lipid is between 0.1 and 3.0, and

(vi) at least 70% of the tctal fatty acid content of the extracted lipid is esterified in the form of TAG.

29. The extracted lipid of claim 28 wherein a level of DHA of about 3% is present in the total fatty acid content of the extracted lipid.

30. The extracted lipid of claim 28 wherein a level of DHA of about 4% is present in the total fatty acid content of the extracted lipid

31. The extracted lipid of claim 28 wherein a level of DHA of about 5% is present in the total fatty acid content of the extracted lipid.

32. The extracted lipid of claim 28 wherein wherein a level of DHA of about 6% is present in the total fatty acid content of the extracted lipid.

33. The extracted lipid of claim 28 , which is from canola seed.

34. The extracted lipid of claim 33 wherein a level of DHA of about 3% is present in the total fatty acid content of the extracted lipid.

35. The extracted lipid of claim 33 wherein a level of DHA of about 4% is present in the total fatty acid content of the extracted lipid.

36. The extracted lipid of claim 33 wherein a level of DHA of about 5% is present in the total fatty acid content of the extracted lipid.

37. The extracted lipid of claim 33 wherein a level of DHA of about 6% is present in the total fatty acid content of the extracted lipid.

Assignments (4)
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 18, 2018
From: PETRIE, JAMES ROBERTSON; SINGH, SURINDER PAL; DE FEYTER, ROBERT CHARLES
To: COMMONWEALTH SCIENTIFIC AND INDUSTRIAL RESEARCH ORGANISATION
Reel/Frame 045570/0979 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 18, 2018
From: COMMONWEALTH SCIENTIFIC AND INDUSTRIAL RESEARCH ORGANISATION
To: COMMONWEALTH SCIENTIFIC AND INDUSTRIAL RESEARCH ORGANISATION; GRAINS RESEARCH AND DEVELOPMENT CORPORATION; NUSEED PTY. LTD.
Reel/Frame 045968/0891 →
35 USC 293 & 37 CFR 3.61 DESIGNATION OF DOMESTIC REPRESENTATIVE Recorded Dec 26, 2017
From: COMMONWEALTH SCIENTIFIC AND INDUSTRIAL RESEARCH ORGANISATION; GRAINS RESEARCH AND DEVELOPMENT CORPORATION; NUSEED PTY. LTD.
To: COMMONWEALTH SCIENTIFIC AND INDUSTRIAL RESEARCH ORGANISATION; GRAINS RESEARCH AND DEVELOPMENT CORPORATION; NUSEED PTY. LTD.
Reel/Frame 044977/0264 →
Continuity (6)
Continuation 13918399 · Jun 14, 2013
Provisional Application 61782680 · Mar 14, 2013
Provisional Application 61697676 · Sep 6, 2012
Provisional Application 61663344 · Jun 22, 2012
Provisional Application 61660392 · Jun 15, 2012
Related Publication 20150045569A1 · Feb 12, 2015