IP Library Granted Patent US 8,816,111
Granted Patent B2
US 8,816,111 · App. 13/918,399 · Granted Aug 26, 2014

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
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Quick Facts
Patent No.
US 8,816,111
App. No.
13/918,399
Granted
Aug 26, 2014
Kind
B2
Abstract

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

Claims (61)

1. Extracted plant lipid, 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 total ω3 fatty acid content which comprises α-linolenic acid (ALA), docosahexaenoic acid (DHA) and one or more of stearidonic acid (SDA), eicosapentaenoic acid (EPA), docosapentaenoic acid (DPA) and eicosatetraenoic acid (ETA),

(e) less than 6% 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 plant 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 plant lipid,

(iii) a level of oleic acid between 1% and 60% is present in the total fatty acid content of the extracted plant lipid,

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

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

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

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

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

2. The extracted plant 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 plant 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 plant lipid,

iii) the extracted plant lipid comprises ω6-docosapentaenoic acid (22:5 Δ 4,7,10,13,16 ) in its total fatty acid content,

iv) a level of SDA 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,

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

vi) the total ω6 fatty acid content in the extracted plant lipid is less than 20% of the total fatty acid content,

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

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

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

x) the extracted plant lipid comprises new ω3 fatty acids in the total ω3 fatty acid content 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 plant lipid is between about 0.1 and about 1,

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

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

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

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

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

xvi) the extracted plant lipid comprises diacylglycerol (DAG), and

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

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

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

5. The extracted plant 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 plant lipid of claim 3 , wherein the oil has a level of cholesterol of less than about 0.5% by weight.

7. The extracted plant lipid of claim 1 , wherein the lipid is in the form of an oil from an oilseed.

8. The extracted plant lipid of claim 7 , wherein the oilseed is a Brassica sp. oilseed or a Camelina sativa oilseed.

9. The extracted plant lipid of claim 7 , wherein the oilseed is canola seed.

10. The extracted plant lipid of claim 1 , wherein the total fatty acid content of the extracted plant lipid comprises less than 1% myristic acid (C14:0).

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

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

13. The extracted plant 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 plant lipid.

14. The extracted plant 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 plant lipid.

15. The extracted plant 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 plant lipid.

16. The extracted plant 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 plant lipid.

17. The extracted plant 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 plant lipid.

18. The extracted plant 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 plant lipid.

19. The extracted plant lipid of claim 1 , wherein a level of DHA between about 8% and 20% is present in the total fatty acid content of the extracted plant lipid.

20. The extracted plant 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 plant lipid.

21. The extracted plant 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 plant lipid.

22. The extracted plant lipid of claim 1 , wherein the extracted plant lipid comprises less than about 0.1% ω6-docosapentaenoic acid (22:5 Δ 4,7,10,13,16 ) in its total fatty acid content.

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

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

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

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

27. 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.

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

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

Assignments (3)
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 Feb 7, 2014
From: PETRIE, JAMES ROBERTSON; SINGH, SURINDER PAL; DE FEYTER, ROBERT CHARLES
To: COMMONWEALTH SCIENTIFIC AND INDUSTRIAL RESEARCH ORGANISATION
Reel/Frame 032170/0470 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 7, 2014
From: COMMONWEALTH SCIENTIFIC AND INDUSTRIAL RESEARCH ORGANISATION
To: COMMONWEALTH SCIENTIFIC AND INDUSTRIAL RESEARCH ORGANISATION; GRAINS RESEARCH AND DEVELOPMENT CORPORATION; NUSEED PTY LTD
Reel/Frame 032170/0509 →
Continuity (5)
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 20130338388A1 · Dec 19, 2013