Lipid compositions comprising triacylglycerol with long-chain polyunsaturated fatty acids

Patent metadata

Field	Value
Publication number	US-11718577-B2
Application number	US-202017063678-A
Country	US
Kind code	B2
Filing date	Oct 5, 2020
Priority date	Dec 18, 2013
Publication date	Aug 8, 2023
Grant date	Aug 8, 2023

Abstract

The present invention relates to lipid comprising docosapentaenoic acid and/or docosahexaenoic acid wherein the docosapentaenoic acid and/or docosahexaenoic acid may be preferentially esterified at the sn-2 position of triacylglycerol, and processes for producing and using the lipid.

First claim

The invention claimed is:

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), docosahexaenoic acid (DHA), 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% by weight, wherein myristic acid is either absent from the extracted lipid or present at a level of less than 1% by weight in the total fatty acid content of the extracted lipid and wherein the level of DHA in the total fatty acid content of the extracted lipid is between 20.1% and 35% by weight.

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% by weight,
ii) the level of myristic acid (C14:0) in the total fatty acid content of the extracted plant lipid is 0.1% by weight,
iii) the level of oleic acid in the total fatty acid content of the extracted plant lipid is between 1% and 30% by weight,
iv) the level of linoleic acid (LA) in the total fatty acid content of the extracted plant lipid is between 4% and 35% by weight,
v) the level of α-linolenic acid (ALA) in the total fatty acid content of the extracted plant lipid is between 4% and 40% by weight,
vi) the extracted plant lipid comprises a level of γ-linolenic acid (GLA) in the total fatty acid content of the extracted plant lipid of less than 4% by weight,
vii) the level of stearidonic acid (SDA) in the total fatty acid content of the extracted plant lipid is less than 10% by weight,
viii) the level of eicosatetraenoic acid (ETA) in the total fatty acid content of the extracted plant lipid is less than 6% by weight,
ix) the extracted plant lipid comprises a level of eicosatrienoic acid (ETrA) in the total fatty acid content of the extracted plant lipid of less than 4% by weight,
x) the level of eicosapentaenoic acid (EPA) in the total fatty acid content of the extracted plant lipid is less than 4% by weight,
xi) the level of docosapentaenoic acid (DPA) in the total fatty acid content of the extracted plant lipid is less than 4% by weight,
xii) the level of DHA in the total fatty acid content of the extracted plant lipid is between 21% and 35% by weight,
xiii) the level of total saturated fatty acids in the total fatty acid content of the extracted plant lipid is between 4% and 25% by weight,
xiv) the level of total monounsaturated fatty acids in the total fatty acid content of the extracted plant lipid is between 4% and 40% by weight,
xv) the level of total polyunsaturated fatty acids in the total fatty acid content of the extracted plant lipid is between 20% and 75% by weight,
xvi) the level of total ω6 fatty acids in the total fatty acid content of the extracted plant lipid is less than 20% by weight,
xvii) the extracted plant lipid comprises a level of new ω6 fatty acids in the total fatty acid content of the extracted plant lipid of less than 10% by weight,
xviii) the level of total ω3 fatty acids in the total fatty acid content of the extracted plant lipid is between 36% 70% by weight,
xix) the extracted plant lipid comprises a level of new ω3 fatty acids in the total fatty acid content of the extracted plant lipid of between 21% and 45% by weight,
xx) 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,
xxi) the extracted plant lipid comprises a ratio of new ω6 fatty acids: new ω3 fatty acids in the fatty acid content of the extracted plant lipid of less than 0.50,
xxii) the fatty acid composition of the extracted plant lipid is based on an efficiency of conversion of ALA to DHA of between 22% and 70%,
xxiii) the total fatty acid in the extracted plant lipid has less than 1.5% C20:1 by weight,
xxiv) the triacylglycerol (TAG) content of the extracted plant lipid is at least 90% by weight,
xxv) the extracted plant lipid comprises less than 10% by weight free (non-esterified) fatty acids and/or phospholipid,
xxvi) at least 70% of the DHA esterified in the form of TAG is in the sn-1 or sn-3 position of the TAG,
xxvii) the most abundant DHA-containing TAG species in the extracted plant lipid is DHA/18:3/18:3 (TAG 58:12), and
xxviii) 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% by weight.

4. The extracted plant lipid of claim 1 , wherein the level of DHA in the total fatty acid content of the lipid was increased after extraction from the plant by a treatment which comprises one or more of fractionation, distillation and transesterification.

5. The extracted plant lipid of claim 4 , wherein the lipid was extracted from Brassica sp. seed or Camelina sativa seed.

6. The extracted plant lipid of claim 1 , wherein the lipid was extracted from Brassica sp. seed.

7. The extracted plant lipid of claim 1 , wherein the lipid was extracted from Camelina sativa seed.

8. The extracted plant lipid of claim 1 , wherein the lipid was extracted from Brassica napus seed.

9. The extracted plant lipid of claim 6 , wherein the lipid comprises tri-DHA TAG.

10. The extracted plant lipid of claim 7 , wherein the lipid comprises tri-DHA TAG.

11. The extracted plant lipid of claim 8 , wherein the lipid comprises tri-DHA TAG.

12. The extracted plant lipid of claim 5 , wherein the lipid was extracted from Brassica sp. seed.

13. The extracted plant lipid of claim 5 , wherein the lipid was extracted from Camelina sativa seed.

14. The extracted plant lipid of claim 5 , wherein the lipid was extracted from Brassica napus seed.

Assignees

• Commw Scient Ind Res Org
• Grains Res & Dev Corp
• Nuseed Nutritional Australia Pty Ltd

Inventors

• Petrie James Robertson
• Singh Surinder Pal
• Shrestha Pushkar
• Mcallister Jason Timothy
• De Feyter Robert Charles
• Devine Malcolm David
• Zhou Xue-Rong

Classifications

• C07C69/587 Primary

  Monocarboxylic acid esters having at least two carbon-to-carbon double bonds · CPC title

• A01H5/00

  Angiosperms, i.e. flowering plants, characterised by their plant parts; Angiosperms characterised otherwise than by their botanic taxonomy · CPC title

• A23D9/00 Primary

  Other edible oils or fats, e.g. shortenings or cooking oils (preservation of other edible oils A23B20/30) · CPC title

• A61K31/20

  having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids · CPC title

• A61K31/201

  having one or two double bonds, e.g. oleic, linoleic acids · CPC title