Lipid comprising polyunsaturated fatty acids

• US 9,550,718 B2
• Filed: 08/20/2014
• Issued: 01/24/2017
• Est. Priority Date: 06/15/2012
• Status: Active Grant

• Current Assignee: Commonwealth Scientific & Industrial Research Organisation (Commonwealth Of Australia As Represented By Department Of Industry, Innovation, Climate Change, Science, Research And Tertiary Education), Grains Research & Development Corporation, Nuseed Nutritional Australia Pty Limited
• Original Assignee: Commonwealth Scientific & Industrial Research Organisation (Commonwealth Of Australia As Represented By Department Of Industry, Innovation, Climate Change, Science, Research And Tertiary Education), Grains Research & Development Corporation, Nuseed Pty. Ltd. (Nufarm Ltd.)
• Inventors: Petrie, James Robertson, Singh, Surinder Pal, de Feyter, Robert Charles
• Primary Examiner(s): Carr, Deborah D
• Application Number:
  US14/464,510
• Publication Number:
  US 20150045569A1
• Time in Patent Office: 888 Days
• Field of Search: 554/224
• US Class Current: 1/1
• CPC Class Codes: A01H 1/104 involving modified lipid metabolism, e.g. seed oil composition
• CPC Class Codes: A01H 5/10 Seeds
• CPC Class Codes: A01H 6/20 Brassicaceae, e.g. canola, broccoli or rucola
• CPC Class Codes: A23K 20/158 Fatty acids; Fats; Products containing oils or fats
• CPC Class Codes: A23L 33/12 Fatty acids or derivatives thereof
• CPC Class Codes: A23V 2002/00 Food compositions, function of food ingredients or processes for food or foodstuffs
• CPC Class Codes: A61K 2236/35 Extraction with lipophilic solvents, e.g. Hexane or petrol ether
• CPC Class Codes: A61K 31/231 having one or two double bonds
• CPC Class Codes: A61K 31/232 having three or more double bonds, e.g. etretinate
• CPC Class Codes: A61K 36/31 Brassicaceae or Cruciferae (Mustard family), e.g. broccoli, cabbage or kohlrabi
• CPC Class Codes: A61P 1/04 for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
• CPC Class Codes: A61P 11/00 Drugs for disorders of the respiratory system
• CPC Class Codes: A61P 11/06 Antiasthmatics
• CPC Class Codes: A61P 13/02 of urine or of the urinary tract, e.g. urine acidifiers
• CPC Class Codes: A61P 13/12 of the kidneys
• CPC Class Codes: A61P 15/00 Drugs for genital or sexual disorders for disorders of sex hormones A61P5/24; Contraceptives
• CPC Class Codes: A61P 17/06 Antipsoriatics
• CPC Class Codes: A61P 17/08 Antiseborrheics
• CPC Class Codes: A61P 19/10 for osteoporosis
• CPC Class Codes: A61P 25/00 Drugs for disorders of the nervous system
• CPC Class Codes: A61P 25/18 : Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
• CPC Class Codes: A61P 25/24 : Antidepressants
• CPC Class Codes: A61P 25/28 : for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
• CPC Class Codes: A61P 27/02 : Ophthalmic agents
• CPC Class Codes: A61P 29/00 : Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
• CPC Class Codes: A61P 3/02 : Nutrients, e.g. vitamins, minerals
• CPC Class Codes: A61P 3/04 : Anorexiants; Antiobesity agents
• CPC Class Codes: A61P 3/10 : for hyperglycaemia, e.g. antidiabetics
• CPC Class Codes: A61P 31/18 : for HIV
• CPC Class Codes: A61P 35/00 : Antineoplastic agents
• CPC Class Codes: A61P 7/02 : Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
• CPC Class Codes: A61P 9/00 : Drugs for disorders of the cardiovascular system
• CPC Class Codes: A61P 9/06 : Antiarrhythmics
• CPC Class Codes: A61P 9/10 : for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
• CPC Class Codes: A61P 9/12 : Antihypertensives
• CPC Class Codes: C07C 57/02 : with only carbon-to-carbon double bonds as unsaturation
• CPC Class Codes: C07C 57/03 : Monocarboxylic acids
• CPC Class Codes: C07C 67/02 : by interreacting ester groups, i.e. transesterification
• CPC Class Codes: C07K 14/415 : from plants
• CPC Class Codes: C11B 1/00 : Production of fats or fatty oils from raw materials
• CPC Class Codes: C11B 1/10 : by extracting
• CPC Class Codes: C11C 1/002 : Sources of fatty acids, e.g. natural glycerides, characterised by the nature, the quantities or the distribution of said acids
• CPC Class Codes: C11C 3/00 : Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom sulfonated fats or oils C07C309/62; factice C08H; drying oils C09F
• CPC Class Codes: C11C 3/003 : by esterification of fatty acids with alcohols C11C3/02 takes precedence
• CPC Class Codes: C11C 3/06 : with glycerol
• CPC Class Codes: C12N 15/8247 : involving modified lipid metabolism, e.g. seed oil composition
• CPC Class Codes: C12N 9/1025 : Acyltransferases (2.3)
• CPC Class Codes: C12Y 203/01 : transferring groups other than amino-acyl groups (2.3.1)
• CPC Class Codes: C12Y 203/01075 : Long-chain-alcohol O-fatty-acyltransferase (2.3.1.75)

Abstract

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

Claims

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 ω

6 fatty acid content which comprises linoleic acid (LA),

(d) a ω

3 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 ω

6 fatty acid content to the ω

3 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 ω

6 fatty acids in the total ω

6 fatty acid content, wherein the level of new ω

6 fatty acids in the extracted lipid is less than about 10% of the total fatty acid content,

vi) the ω

3 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 ω

6 fatty acid content to the ω

3 fatty acid content in total in the extracted lipid is between about 0.1 and about 0.5,

viii) the extracted lipid comprises new ω

3 fatty acids in the ω

3 fatty acid content in total and new ω

6 fatty acids in the total ω

6 fatty acid content, wherein the ratio of the new ω

6 fatty acids to the new ω

3 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, Δ

5-stigmasterol, eburicol, β

-sitosterol, Δ

5-avenasterol, Δ

7-stigmasterol and Δ

7-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% ω

6-docosapentaenoic acid (22;

5<sup>Δ

4, 7, 10, 13, 16</sup>) 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 ω

6 fatty acid content and the ω

3 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 ω

3 fatty acids in the ω

3 fatty acid content in total, wherein the level of new ω

3 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 ω

6-docosapentaenoic acid (22;

5<sup>Δ

4, 7, 10, 13, 16</sup>) in its total fatty acid content.

26. The extracted lipid of claim 1, wherein the total ω

6 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 ω

6 fatty acid content which comprises linoleic acid (LA),

(d) a ω

3 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 ω

6 fatty acid content to the ω

3 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.