IP Library Granted Patent US 11,872,201
Granted Patent B2
US 11,872,201 · App. 17/253,596 · Granted Jan 16, 2024

DHA enriched polyunsaturated fatty acid compositions

Inventor: Stuart Littler (Clayton, AU)
Assignee: Nuseed Nutritional US Inc.
A61K31/202A61K31/232A61K36/185A61K36/28A61K36/286A61K36/31A61K36/48A61K36/55A61K36/81A61K36/889A61K36/899A61K2236/13A61K2236/53
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Quick Facts
Patent No.
US 11,872,201
App. No.
17/253,596
Granted
Jan 16, 2024
Kind
B2
Abstract

There is provided a vegetable-based lipid composition comprising very high levels of DHA, together with at least one other long-chain polyunsaturated fatty acid (typically as fatty acid esters). The composition typically contains low levels of EPA and palmitic acid. The composition is obtainable from a single source by conventional processing methods, and has improved stability properties.

Claims (42)

1. A vegetable-based lipid composition comprising:

(i) docosahexaenoic acid (22:6n-3) in an amount of at least 86% by weight of the total fatty acid content of the composition;

(ii) eicosatetraenoic acid (20:4n-3) in an amount of 3% to 12% by weight of the total fatty acid content of the composition, wherein the eicosatetraenoic acid is the second most abundant polyunsaturated fatty acid in the composition; and

(iii) α-linolenic acid (18:3n-3) in an amount of from 0.1% to 4% by weight of the total fatty acid content of the composition;

wherein the docosahexaenoic acid, the eicosatetraenoic acid and the α-linolenic acid are each independently provided in the form of a fatty acid, a fatty acid salt, a fatty acid ester or a salt of a fatty acid ester.

2. The lipid composition of claim 1 , wherein docosahexaenoic acid (22:6n-3) is present in an amount of about 87% to about 96% by weight of the total fatty acid content of the composition.

3. The lipid composition of claim 1 , wherein the weight ratio of docosahexaenoic acid to eicosapentaenoic acid in the composition is at least 50:1.

4. The lipid composition of claim 1 , wherein the docosahexaenoic acid, the eicosatetraenoic acid, and the α-linolenic acid are each independently provided in the form of a fatty acid ester or a salt of a fatty acid ester.

5. The lipid composition of claim 4 , wherein the docosahexaenoic acid, the eicosatetraenoic acid, and the α-linolenic acid are each independently provided in the form of a fatty acid ethyl ester or as part of a triglyceride.

6. The lipid composition of claim 1 , wherein the amount of palmitic acid in the composition is less than 0.5% by weight of the total fatty acid content of the composition.

7. The lipid composition of claim 1 , wherein the lipid composition is derived from a single source.

8. The lipid composition of claim 1 , wherein the lipid composition is derived from a plant.

9. The lipid composition of claim 8 , wherein the plant is an oilseed selected from Brassica sp., Gossypium hirsutum, Linum usitatissimum, Helianthus sp., Carthamus tinctorius, Glycine max, Zea mays, Arabidopsis thaliana, Sorghum bicolor, Sorghum vulgare, Avena sativa, Trifolium sp., Elaesis guineensis, Nicotiana benthamiana, Hordeum vulgare, Lupinus angustifolius, Oryza sativa, Oryza glaberrima, Camelina sativa , or Crambe abyssinica.

10. The lipid composition of claim 9 , wherein the lipid composition is obtained from a seed oil that has been degummed, refined, bleached and/or deodorised.

11. The lipid composition of claim 9 , wherein the plant is Brassica napus or Brassica juncea.

12. The lipid composition of claim 9 , wherein the plant has been genetically modified to enhance its ability to produce long chain polyunsaturated fatty acids.

13. The lipid composition of claim 1 , wherein the composition is provided in the form of a tablet, capsule, encapsulated gel, ingestible liquid or powder, emulsion, or a topical ointment or cream.

14. The lipid composition of claim 1 , further comprising one or more additional components selected from the group consisting of an antioxidant, a stabiliser and a surfactant.

15. The lipid composition of claim 1 for use in the treatment or prevention of cardiovascular disease, protection against death in patients with cardiovascular disease, reduction of overall serum cholesterol levels, reduction in high blood pressure, increase in HDL:LDL ratio, reduction of triglycerides, or reduction of apolipoprotein-B levels.

16. The lipid composition of claim 1 , wherein the composition comprises α-linolenic acid (18:3n-3) in an amount of from about 0.5% to about 2% by weight of the total fatty acid content of the composition.

17. The lipid composition of claim 1 , wherein the composition comprises up to 1% eicosapentaenoic acid (20:5n-3) by weight of the total fatty acid content of the composition.

18. A method for producing the lipid composition of claim 1 , comprising providing a mixture of fatty acid ethyl esters, and subjecting said mixture to a chromatographic separation process, optionally wherein the mixture of fatty acid ethyl esters is obtained by transesterification and distillation of a vegetable-based lipid oil.

19. A vegetable-based lipid composition comprising:

(i) docosahexaenoic acid (22:6n-3) in an amount of at least 86% by weight of the total fatty acid content of the composition;

(ii) eicosatetraenoic acid (20:4n-3) in an amount of 3% to 12% by weight of the total fatty acid content of the composition, wherein the eicosatetraenoic acid is the second most abundant polyunsaturated fatty acid in the composition; and

(iii) α-linolenic acid (18:3n-3) in an amount of from 0.1% to 4% by weight of the total fatty acid content of the composition;

wherein the vegetable-based lipid composition is obtained by providing a mixture of fatty acid ethyl esters and subjecting said mixture to a chromatographic separation process, optionally wherein the mixture of fatty acid ethyl esters is obtained by transesterification and distillation of a vegetable-based lipid oil; and

wherein the docosahexaenoic acid, the eicosatetraenoic acid and the α-linolenic acid are each independently provided in the form of a fatty acid, a fatty acid salt, a fatty acid ester or a salt of a fatty acid ester.

20. The lipid composition of claim 19 , wherein docosahexaenoic acid (22:6n-3) is present in an amount of about 87% to about 96% by weight of the total fatty acid content of the composition.

21. The lipid composition of claim 19 , wherein the docosahexaenoic acid, the eicosatetraenoic acid, and the α-linolenic acid are each independently provided in the form of a fatty acid ester or a salt of a fatty acid ester.

22. The lipid composition of claim 19 , wherein the amount of palmitic acid in the composition is less than 0.5% by weight of the total fatty acid content of the composition.

23. The lipid composition of claim 19 , wherein the composition is provided in the form of a tablet, capsule, encapsulated gel, ingestible liquid or powder, emulsion, or a topical ointment or cream.

24. A vegetable-based lipid composition comprising:

(i) docosahexaenoic acid (22:6n-3) in an amount of at least 86% by weight of the total fatty acid content of the composition;

(ii) eicosatetraenoic acid (20:4n-3) in an amount of 3% to 12% by weight of the total fatty acid content of the composition, wherein the eicosatetraenoic acid is the second most abundant polyunsaturated fatty acid in the composition; and

(iii) α-linolenic acid (18:3n-3) in an amount of from 0.1% to 4% by weight of the total fatty acid content of the composition;

wherein the docosahexaenoic acid, the eicosatetraenoic acid and the α-linolenic acid are each independently provided in the form of a fatty acid, a fatty acid salt, a fatty acid ester or a salt of a fatty acid ester; and

wherein the lipid composition is derived from an oilseed plant or a plant selected from Brassica sp., Gossypium hirsutum, Linum usitatissimum, Helianthus sp., Carthamus tinctorius, Glycine max, Zea mays, Arabidopsis thaliana, Sorghum bicolor, Sorghum vulgare, Avena sativa, Trifolium sp., Elaesis guineensis, Nicotiana benthamiana, Hordeum vulgare, Lupinus angustifolius, Oryza sativa, Oryza glaberrima, Camelina sativa , or Crambe abyssinica.

25. The lipid composition of claim 24 , wherein docosahexaenoic acid (22:6n-3) is present in an amount of about 87% to about 96% by weight of the total fatty acid content of the composition.

26. The lipid composition of claim 24 , wherein the docosahexaenoic acid, the eicosatetraenoic acid, and the α-linolenic acid are each independently provided in the form of a fatty acid ester or a salt of a fatty acid ester.

27. The lipid composition of claim 24 , wherein the amount of palmitic acid in the composition is less than 0.5% by weight of the total fatty acid content of the composition.

28. The lipid composition of claim 24 , wherein the composition is provided in the form of a tablet, capsule, encapsulated gel, ingestible liquid or powder, emulsion, or a topical ointment or cream.

Assignments (7)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 13, 2023
From: LITTLER, STUART
To: COMMONWEALTH SCIENTIFIC AND INDUSTRIAL RESEARCH ORGANISATION
Reel/Frame 062388/0961 →
SECURITY INTEREST Recorded Dec 5, 2022
From: NUFARM AMERICAS, INC.; NUSEED AMERICAS, INC.; NUSEED NUTRITIONAL US INC.
To: BANK OF AMERICA, N.A.
Reel/Frame 061972/0303 →
SECURITY INTEREST Recorded Dec 5, 2022
From: NUFARM AMERICAS, INC.; NUSEED AMERICAS, INC.; NUSEED NUTRITIONAL US INC.
To: ANZ FIDUCIARY SERVICES PTY LTD
Reel/Frame 061972/0332 →
SECURITY INTEREST Recorded Nov 22, 2022
From: NUFARM AMERICAS, INC.; NUSEED AMERICAS INC.; NUSEED NUTRITIONAL US INC.
To: ANZ FIDUCIARY SERVICES PTY LTD
Reel/Frame 061853/0142 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 9, 2021
From: COMMONWEALTH SCIENTIFIC AND INDUSTRIAL RESEARCH ORGANISATION
To: NUSEED PTY LTD.
Reel/Frame 057429/0511 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 28, 2021
From: NUSEED PTY LTD.
To: NUSEED AMERICAS INC.
Reel/Frame 056685/0888 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 28, 2021
From: NUSEED AMERICAS INC.
To: NUSEED NUTRITIONAL US INC.
Reel/Frame 056686/0116 →
Priority Claims (1)
EP 18179070 · Jun 21, 2018 · regional
Continuity (1)
Related Publication 20210251937A1 · Aug 19, 2021