IP Library › Granted Patent US 12,421,472
Granted Patent B2
US 12,421,472 · App. 17/709,128 · Granted Sep 23, 2025

Process for producing extracted lipid comprising docosahexaenoic acid

Inventors: James Robertson Petrie (Goulburn, AU); Surinder Pal Singh (Downer, AU); Robert Charles de Feyter (Monash, AU)
Assignees: COMMONWEALTH SCIENTIFIC INDUSTRIAL RESEARCH ORGANISATION -; GRAINS RESEARCH AND DEVELOPMENT CORPORATION - Barton, Australia
C11B1/10A01H1/104A01H5/10A01H6/20A61K36/31C07C57/02C07C57/03C07C67/02C11B1/00C11C1/002C11C3/00C11C3/003C11C3/06C12N9/1025C12N15/8247A23K20/158A23L33/12A23V2002/00A61K31/231A61K31/232A61K2236/35C07K14/415
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Quick Facts
Patent No.
US 12,421,472
App. No.
17/709,128
Granted
Sep 23, 2025
Kind
B2
Abstract

The present invention relates to a process for producing ethyl esters of polyunsaturated fatty acids, comprising transesterifying triacylglycerols in extracted plant lipid.

Claims (26)

1. A process for producing extracted plant lipid comprising the steps of:

i) obtaining Brassica napus seed or Camelina sativa seed from Brassica napus plants or Camelina sativa plants, respectively, wherein the plants are grown in a field as a population of at least 1,000 such plants, which seed comprise extractable lipid having a total fatty acid content comprising fatty acids in an esterified form, the fatty acids comprising oleic acid, palmitic acid, a total ω6 fatty acid content which comprises linoleic acid (LA) and γ-linolenic acid (GLA), and a total ω3 fatty acid content which comprises α-linolenic acid (ALA), stearidonic acid (SDA), docosapentaenoic acid (DPA), eicosapentaenoic acid (EPA) and eicosatetraenoic acid (ETA), wherein

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

b) myristic acid is either absent or is present in the extractable lipid at a level of less than 1% of the total fatty acid content,

c) oleic acid is present in the extractable lipid at a level of between 1% and 30% of the total fatty acid content,

d) LA is present in the extractable lipid at a level of between 4% and 35% of the total fatty acid content,

e) GLA is present in the extractable lipid at a level of less than 4% of the total fatty acid content,

f) ALA is present in the extractable lipid at a level of between 4% and 40% of the total fatty acid content,

g) the total saturated fatty acid content of the extractable lipid is between 4% and 25% of the total fatty acid content,

h) the ratio of the total ω6 fatty acid content to the total ω3 fatty acid content in the total fatty acid content is between 0.1 and 1, and

i) SDA, ETA, EPA and DPA are each present at a level in the total fatty acid content, each level being expressed as a percentage of the total fatty acid content, whereby the sum of the percentages for ETA, EPA and DPA divided by the sum of the percentages for SDA, ETA, EPA and DPA, expressed as a percentage, is at least 75%,

wherein each percentage is a percentage by weight,

and

ii) extracting lipid from the seed to thereby produce the extracted plant lipid.

2. The process of claim 1 , wherein the process comprises, prior to step (i), a step of cultivating the at least 1,000 Brassica napus plants or Camelina sativa plants in the field, and step (i) comprises harvesting Brassica napus seed or Camelina sativa seed from the at least 1,000 Brassica napus plants or Camelina sativa plants, respectively.

3. The process of claim 1 , further comprising a step of purifying the extracted lipid.

4. The process of claim 3 , further comprising a step of transesterifying the purified extracted lipid to thereby produce fatty acid esters.

5. The process of claim 4 , further comprising a step of fractionating the fatty acid esters.

6. The process of claim 1 , wherein the extracted lipid comprises C20:1 at a level of less than 1% by weight of the total fatty acid content.

7. The process of claim 1 , wherein the extracted lipid comprises a new ω3 fatty acid content in the total ω3 fatty acid content and a new ω6 fatty acid content in the total ω6 fatty acid content, wherein the ratio of the new ω6 fatty acid content to the new ω3 fatty acid content, each expressed as a percentage by weight of the total fatty acid content, is less than 0.20.

8. The process of claim 1 , wherein ALA, SDA, ETA, EPA and DPA are each present at a level in the total fatty acid content, each level being expressed as a percentage by weight of the total fatty acid content, and eicosatrienoic acid (ETrA) is either present or absent in the total fatty acid content, whereby the sum of the percentages for SDA, ETA, EPA, and DPA divided by the sum of the percentages for ALA, SDA, ETrA, ETA, EPA and DPA, expressed as a percentage, is at least 30%.

9. The process of claim 1 , wherein ETA, EPA and DPA are each present at a level in the total fatty acid content, each level being expressed as a percentage by weight of the total fatty acid content, whereby the sum of the percentages for EPA and DPA divided by the sum of the percentages for ETA, EPA and DPA, expressed as a percentage, is between 75% and 98%.

10. The process of claim 1 , wherein the seeds are transgenic for a polynucleotide encoding a Δ6 desaturase, wherein the Δ6 desaturase is Mantoniella squamata Δ6 desaturase, Ostreococcus tauri Δ6 desaturase or Micromonas pusilla Δ6 desaturase.

11. The process of claim 10 , wherein the seeds are transgenic for a polynucleotide encoding a Δ6 elongase, wherein the Δ6 elongase is Physcomitrella patens Δ6 elongase.

12. The process of claim 11 , further comprising a step of purifying the extracted lipid.

13. The process of claim 1 , wherein GLA is present in the extracted lipid at a level of less than 3% by weight of the total fatty acid content.

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 4, 2022
From: PETRIE, JAMES ROBERTSON; SINGH, SURINDER PAL; DE FEYTER, ROBERT CHARLES
To: COMMONWEALTH SCIENTIFIC AND INDUSTRIAL RESEARCH ORGANISATION
Reel/Frame 059487/0589 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 4, 2022
From: COMMONWEALTH SCIENTIFIC AND INDUSTRIAL RESEARCH ORGANISATION
To: COMMONWEALTH SCIENTIFIC AND INDUSTRIAL RESEARCH ORGANISATION; GRAINS RESEARCH AND DEVELOPMENT CORPORATION; NUSEED PTY LTD
Reel/Frame 059487/0639 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 4, 2022
From: NUSEED PROPRIETARY LIMITED
To: NUSEED NUTRITIONAL AUSTRALIA PTY LTD
Reel/Frame 059487/0700 →
Continuity (11)
Continuation 16868324 · May 6, 2020
Continuation 15961200 · Apr 24, 2018
Continuation 15678008 · Aug 15, 2017
Continuation 15400532 · Jan 6, 2017
Continuation 14600653 · Jan 20, 2015
Continuation 13918392 · 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 20220356414A1 · Nov 10, 2022
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