IP Library Granted Patent US 8,278,351
Granted Patent B2
US 8,278,351 · App. 13/189,714 · Granted Oct 2, 2012

Natural marine source phospholipids comprising polyunsaturated fatty acids and their applications

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Quick Facts
Patent No.
US 8,278,351
App. No.
13/189,714
Granted
Oct 2, 2012
Kind
B2
Abstract

A phospholipid extract from a marine or aquatic biomass possesses therapeutic properties. The phospholipid extract comprises a variety of phospholipids, fatty acid, metals and a novel flavonoid.

Claims (886)

1. A krill extract comprising:

a phospholipid of the general formula (I),

wherein R1 and R2, each together with the respective carboxyl groups to which each is attached, each independently represents a docosahexaenoic acid (DHA) or an eicosapentanoic acid (EPA) residue, and X is —CH 2 CH 2 NH 3 , —CH 2 CH 2 N(CH 3 ) 3 , or

 and

wherein the extract is suitable for human consumption.

2. The extract according to claim 1 , wherein the extract has a total phospholipid concentration in an amount of about 40% w/w, wherein about represents ±10%.

3. The extract according to claim 1 , wherein the extract has a total phospholipid concentration in an amount of about 45% w/w, wherein about represents ±20%.

4. The extract according to claim 1 , further comprising an additional lipid, wherein the additional lipid is selected from the group consisting of monoglycerides, triglycerides, cholesterols, mixtures thereof, and free fatty acids.

5. The extract according to claim 1 , wherein the extract has a concentration of free fatty acids of about 5% w/w of the lipids in the extract.

6. The extract according to claim 1 , wherein the extract further comprises polyunsaturated fatty acids which comprise at least 15% w/w of the lipids in the extract.

7. The extract according to claim 1 , wherein the extract further comprises polyunsaturated fatty acids which comprise at least 40% w/w of the lipids in the extract.

8. The extract according to claim 1 , wherein the extract further comprises polyunsaturated fatty acids which comprise at least 45% w/w of the lipids in the extract.

9. The extract according to claims 6 , 7 , or 8 , wherein the polyunsaturated fatty acids are omega-3 fatty acids.

10. The extract according to claim 1 , wherein DHA and EPA comprise at least 32% w/w of the lipids in the extract.

11. The extract according to claim 1 , wherein DHA and EPA comprise at least 35% w/w of the lipids in the extract.

12. The extract according to claim 1 , further comprising a metal.

13. The extract according to claim 12 , wherein the metal is zinc, selenium or a mixture thereof.

14. The extract according to claim 13 , wherein the zinc comprises at least 0.005 mg/100 g of the extract and the selenium comprises less than 3 mg/100 g of the extract.

15. The extract according to claim 4 , wherein the fatty acid composition of the lipids in the extract is about:

Total

Phosphatidyl-

Phosphatidyl-

Phospholipid

choline

ethanolamine

Fatty Acids

Fatty Acid %

Fatty Acid %

Fatty Acid %

C14:0 MYRISTIC

2

2

0.7

C14:1 MYRISTOLEIC

1

C15:0 PENTADECANOIC

0.2

0.3

0.3

C16:0 PALMITIC

24

27

24

C16:1 PALMITOLEIC

2

2

0.7

C18:0 STEARIC

1

1

3

C18:1 OLEIC

9

12

24

C18:2n6 LINOLEIC

2

2

0.8

C18:3n6 GLA

1

0.3

C18:3n3 ALA

1

1

C18:4n3 OTA

2

2

0.3

C20:0 ARACHIDIC

C20:1 cis-11-EICOSENOIC

0.5

0.6

0.7

C20:2n6 EICOSADIENOIC

C20:3n6 METHYL ETA

0.2

C20:4n6 ARACHIDONIC

0.6

0.7

0.6

C20:3n3 Homo-γ-

LINOLENIC

C20:4n3

C20:5n3 EPA

27

32

13

C22:0 BEHENIC

C22:1 ERUCIC

1

1.5

C22:2n6

C22:4n6

C22:5n6 METHYL DPA

C22:5n3 DPA

1.00

C22:6n3 DHA

25

14

32

C24:0 LIGNOCERIC

C24:1 NERVONIC

Total

100.0

100

100;

wherein about represents ±10%.

16. The extract according to claim 15 , wherein the total fatty acid composition of all the lipids in the extract is:

Sample

%

Fatty Acid Composition

C14:0

≧3.00

C14:1

≧0.01

C15:0

≧0.3

C16:0

≧20.00

C16:1

≧3.25

C18:0

≧1.00

C18:1

≧10.00

C18:2n6

≧2.00

C18:3n6 GLA

≧0.04

C18:3n3 ALA

≧0.01

C18:4n3

≧1.50

C20:0

≧0.05

C20:1

≧1.00

C20:2n6

≧0.05

C20:3n6

≧0.05

C20:4n6

≧0.50

C20:3n3

≧0.01

C20:4n3

≧0.20

C20:5n3 EPA

≧25.00

C22:0

≧0.01

C22:1

≧1.50

C22:2n6

≧0.03

C22:4n6

≧0.01

C22:5n6

≧0.01

C22:5n3 DPA

≧0.50

C22:6n3 DHA

≧10.00

C24:0

≧0.01

C24:1

≧0.05.

17. The extract according to claim 16 , wherein the total fatty acid composition of all the lipids is:

Saturated (g/100 g lipid)

≧22.00

Monounsaturated (g/100 g lipid)

≧11.00

Polyunsaturated (g/100 g lipid)

≧35.00

Omega-3 (g/100 g lipid)

≧30.00

Omega-6 (g/100 g lipid)

≧1.00.

18. The extract according to claim 4 , comprising:

Monoglycerides (MG) (g/100 g sample)

≧0.7

Triglycerides (TG) (g/100 g sample)

≧3.00

Free Fatty Acids (FFA) (g/100 g sample)

≧5.00

Cholesterol (g/100 g sample)

≦2.00

Total Phospholipids (PL) (g/100 g sample)

≧40.00

Phosphatidyl Ethanolamine (PE) (g/100 g sample)

≧2.50

Phosphatidyl Inositol (PI) (g/100 g sample)

≧0.20

Phosphatidyl Serine (PS) (g/100 g sample)

≧0.20

Phosphatidyl Choline (PC) (g/100 g sample)

≧35.00

Sphingomyelin (g/100 g sample)

≧0.50

Vitamin A (μg/100 ml)

≧1,400

Vitamin E (μg/100 ml)

≧15

Beta-Carotene (μg/100 ml)

≧1,600

Astaxanthin (mg/100 ml)

≧10

Canthaxanthin (mg/100 ml)

≧10

Flavonoid (mg/100 ml)

≧7.0.

19. The extract of claim 1 , wherein one of R1 and R2 is EPA and the other is DHA.

20. The extract of claim 1 , wherein R1 and R2 is EPA.

21. The extract of claim 1 , wherein R1 and R2 is DHA.

22. The extract of claim 1 , further comprising an antioxidant.

23. The extract of claim 22 , wherein the antioxidant is selected from the group consisting of vitamin A, vitamin E, carotenoid, beta-carotene, astaxanthin, canthaxanthin, flavonoids, and mixtures thereof.

24. A capsule, tablet, solution, syrup, or suspension comprising a krill extract comprising:

a phospholipid of the formula (I),

wherein R1 and R2, each together with the respective carboxyl groups to which each is attached, each independently represents a docosahexaenoic acid (DHA) or an eicosapentaenoic acid (EPA) residue, and X is —CH 2 CH 2 NH 3 , —CH 2 CH 2 N(CH 3 ) 3 , or

 and wherein the extract is suitable for human consumption.

25. The extract according to claim 24 , wherein the extract has a total phospholipid concentration in an amount of about 40% w/w, wherein about represents ±10%.

26. The extract according to claim 24 , wherein the extract has a total phospholipid concentration in an amount of about 45% w/w, wherein about represents ±20%.

27. The formulation according to claim 24 , further comprising an additional lipid, wherein the additional lipid is selected from the group consisting of monoglycerides, triglycerides, cholesterols, mixtures thereof, and free fatty acids.

28. The formulation according to claim 24 , wherein the extract has a concentration of free fatty acids of about 5% w/w of the lipids in the extract.

29. The formulation according to claim 24 , wherein the extract further comprises polyunsaturated fatty acids which comprise at least 15% w/w of the lipids in the extract.

30. The formulation according to claim 24 , wherein the extract further comprises polyunsaturated fatty acids which comprise at least 40% w/w of the lipids in the extract.

31. The formulation according to claim 24 , wherein the extract further comprises polyunsaturated fatty acids which comprise at least 45% w/w of the lipids in the extract.

32. The formulation according to claim 29 , 30 , or 31 , wherein the polyunsaturated fatty acids are omega-3 fatty acids.

33. The formulation according to claim 24 , wherein DHA and EPA comprise at least 32% w/w of the lipids in the extract.

34. The formulation according to claim 24 , wherein DHA and EPA comprise at least 35% w/w of the lipids in the extract.

35. The formulation according to claim 24 , further comprising a metal.

36. The formulation according to claim 35 , wherein the metal is zinc, selenium or a mixture thereof

37. The formulation according to claim 36 , wherein the zinc comprises at least 0.005mg/100g of the extract and the selenium comprises less than 3 mg/100g of the extract.

38. The formulation according to claim 24 , wherein the fatty acid composition of the lipids in the extract is about:

Total

Phosphatidyl-

Phosphatidyl-

Phospholipid

choline

ethanolamine

Fatty Acids

Fatty Acid %

Fatty Acid %

Fatty Acid %

C14:0 MYRISTIC

2

2

0.7

C14:1 MYRISTOLEIC

1

C15:0

0.2

0.3

0.3

PENTADECANOIC

C16:0 PALMITIC

24

27

24

C16:1 PALMITOLEIC

2

2

0.7

C18:0 STEARIC

1

1

3

C18:1 OLEIC

9

12

24

C18:2n6 LINOLEIC

2

2

0.8

C18:3n6 GLA

1

0.3

C18:3n3 ALA

1

1

C18:4n3 OTA

2

2

0.3

C20:0 ARACHIDIC

C20:1 cis-11-

0.5

0.6

0.7

EICOSENOIC

C20:2n6

EICOSADIENOIC

C20:3n6 METHYL ETA

0.2

C20:4n6

0.6

0.7

0.6

ARACHIDONIC

C20:3n3 Homo-γ-

LINOLENIC

C20:4n3

C20:5n3 EPA

27

32

13

C22:0 BEHENIC

C22:1 ERUCIC

1

1.5

C22:2n6

C22:4n6

C22:5n6 METHYL DPA

C22:5n3 DPA

1.00

C22:6n3 DHA

25

14

32

C24:0 LIGNOCERIC

C24:1 NERVONIC

Total

100.0

100

100;

wherein about represents ±10%.

39. The formulation according to claim 38 , wherein the total fatty acid composition of all the lipids in the extract is:

Sample

%

Fatty Acid Composition

C14:0

≧3.00

C14:1

≧0.01

C15:0

≧0.3

C16:0

≧20.00

C16:1

≧3.25

C18:0

≧1.00

C18:1

≧10.00

C18:2n6

≧2.00

C18:3n6 GLA

≧0.04

C18:3n3 ALA

≧0.01

C18:4n3

≧1.50

C20:0

≧0.05

C20:1

≧1.00

C20:2n6

≧0.05

C20:3n6

≧0.05

C20:4n6

≧0.50

C20:3n3

≧0.01

C20:4n3

≧0.20

C20:5n3 EPA

≧25.00

C22:0

≧0.01

C22:1

≧1.50

C22:2n6

≧0.03

C22:4n6

≧0.01

C22:5n6

≧0.01

C22:5n3 DPA

≧0.50

C22:6n3 DHA

≧10.00

C24:0

≧0.01

C24:1

≧0.05.

40. The formulation according to claim 39 , wherein the total fatty acid composition of all the lipids is:

Saturated (g/100 g lipid)

≧22.00

Monounsaturated (g/100 g lipid)

≧11.00

Polyunsaturated (g/100 g lipid)

≧35.00

Omega-3 (g/100 g lipid)

≧30.00

Omega-6 (g/100 g lipid)

≧1.00.

41. The formulation according to claim 27 , comprising:

Monoglycerides (MG) (g/100 g sample)

≧0.7

Triglycerides (TG) (g/100 g sample)

≧3.00

Free Fatty Acids (FFA) (g/100 g sample)

≧5.00

Cholesterol (g/100 g sample)

≦2.00

Total Phospholipids (PL) (g/100 g sample)

≧40.00

Phosphatidyl Ethanolamine (PE) (g/100 g sample)

≧2.50

Phosphatidyl Inositol (PI) (g/100 g sample)

≧0.20

Phosphatidyl Serine (PS) (g/100 g sample)

≧0.20

Phosphatidyl Choline (PC) (g/100 g sample)

≧35.00

Sphingomyelin (g/100 g sample)

≧0.50

Vitamin A (μg/100 ml)

≧1,400

Vitamin E (μg/100 ml)

≧15

Beta-Carotene (μg/100 ml)

≧1,600

Astaxanthin (mg/100 ml)

≧10

Canthaxanthin (mg/100 ml)

≧10

Flavonoid (mg/100 ml)

≧7.0.

42. The formulation of claim 24 , wherein one of R1 and R2 is EPA and the other is DHA.

43. The formulation of claim 24 , wherein R1 and R2 is EPA.

44. The formulation of claim 24 , wherein R1 and R2 is DHA.

45. The formulation of claim 24 , further comprising an antioxidant.

46. The formulation of claim 45 , wherein the antioxidant is selected from the group consisting of vitamin A, vitamin E, carotenoid, beta-carotene, astaxanthin, canthaxanthin, flavonoids, and mixtures thereof.

47. A food, beverage, energy bar, or nutritional supplement comprising a krill extract comprising:

a phospholipid of the formula (I),

wherein R1 and R2, each together with the respective carboxyl groups to which each is attached, each independently represents a docosahexaenoic acid (DHA) or an eicosapentaenoic acid (EPA) residue, and X is —CH 2 CH 2 NH 3 , —CH 2 CH 2 N(CH 3 ) 3 , or

 and

wherein the extract is suitable for human consumption.

48. The extract according to claim 47 , wherein the extract has a total phospholipid concentration in an amount of about 40% w/w, wherein about represents ±10%.

49. The extract according to claim 47 , wherein the extract has a total phospholipid concentration in an amount of about 45% w/w, wherein about represents ±20%.

50. The nutraceutical composition of claim 47 , wherein the extract further comprises an additional lipid, wherein the additional lipid is selected from the group consisting of monoglycerides, triglycerides, cholesterols, mixtures thereof, and free fatty acids.

51. The nutraceutical composition of claim 47 , wherein the extract has a concentration of free fatty acids of about 5% w/w of the lipids in the extract.

52. The nutraceutical composition of claim 47 , wherein polyunsaturated fatty acids comprise at least 15% w/w of the lipids in the extract.

53. The nutraceutical composition of claim 47 , wherein the extract further comprises polyunsaturated fatty acids which comprise at least 40% w/w of the lipids in the extract.

54. The nutraceutical composition of claim 47 , wherein the extract further comprises polyunsaturated fatty acids which comprise at least 45% w/w of the lipids in the extract.

55. The nutraceutical composition of claim 52 , 53 , or 54 , wherein the polyunsaturated fatty acids are omega-3 fatty acids.

56. The nutraceutical composition of claim 47 , wherein DHA and EPA comprise at least 32% w/w of the lipids in the extract.

57. The nutraceutical composition of claim 47 , wherein DHA and EPA comprise at least 35% w/w of the lipids in the extract.

58. The nutraceutical composition of claim 47 , wherein the extract further comprises a metal.

59. The nutraceutical composition of claim 58 , wherein the metal is zinc, selenium or a mixture thereof.

60. The nutraceutical composition of claim 59 , wherein the zinc comprises at least 0.005 mg/100g of the extract and the selenium comprises less than 3 mg/100g of the extract.

61. The nutraceutical composition of claim 50 , wherein the fatty acid composition of the lipids in the extract is about:

Total

Phosphatidyl-

Phosphatidyl-

Phospholipid

choline

ethanolamine

Fatty Acids

Fatty Acid %

Fatty Acid %

Fatty Acid %

C14:0 MYRISTIC

2

2

0.7

C14:1 MYRISTOLEIC

1

C15:0

0.2

0.3

0.3

PENTADECANOIC

C16:0 PALMITIC

24

27

24

C16:1 PALMITOLEIC

2

2

0.7

C18:0 STEARIC

1

1

3

C18:1 OLEIC

9

12

24

C18:2n6 LINOLEIC

2

2

0.8

C18:3n6 GLA

1

0.3

C18:3n3 ALA

1

1

C18:4n3 OTA

2

2

0.3

C20:0 ARACHIDIC

C20:1 cis-11-

0.5

0.6

0.7

EICOSENOIC

C20:2n6

EICOSADIENOIC

C20:3n6 METHYL ETA

0.2

C20:4n6

0.6

0.7

0.6

ARACHIDONIC

C20:3n3 Homo-γ-

LINOLENIC

C20:4n3

C20:5n3 EPA

27

32

13

C22:0 BEHENIC

C22:1 ERUCIC

1

1.5

C22:2n6

C22:4n6

C22:5n6 METHYL DPA

C22:5n3 DPA

1.00

C22:6n3 DHA

25

14

32

C24:0 LIGNOCERIC

C24:1 NERVONIC

Total

100.0

100

100;

wherein about represents ±10%.

62. The nutraceutical composition of claim 61 , wherein the total fatty acid composition of all the lipids in the extract is:

Sample

%

Fatty Acid Composition

C14:0

≧3.00

C14:1

≧0.01

C15:0

≧0.3

C16:0

≧20.00

C16:1

≧3.25

C18:0

≧1.00

C18:1

≧10.00

C18:2n6

≧2.00

C18:3n6 GLA

≧0.04

C18:3n3 ALA

≧0.01

C18:4n3

≧1.50

C20:0

≧0.05

C20:1

≧1.00

C20:2n6

≧0.05

C20:3n6

≧0.05

C20:4n6

≧0.50

C20:3n3

≧0.01

C20:4n3

≧0.20

C20:5n3 EPA

≧25.00

C22:0

≧0.01

C22:1

≧1.50

C22:2n6

≧0.03

C22:4n6

≧0.01

C22:5n6

≧0.01

C22:5n3 DPA

≧0.50

C22:6n3 DHA

≧10.00

C24:0

≧0.01

C24:1

≧0.05.

63. The nutraceutical composition of claim 62 , wherein the total fatty acid composition of all the lipids is:

Saturated (g/100 g lipid)

≧22.00

Monounsaturated (g/100 g lipid)

≧11.00

Polyunsaturated (g/100 g lipid)

≧35.00

Omega-3 (g/100 g lipid)

≧30.00

Omega-6 (g/100 g lipid)

≧1.00.

64. The nutraceutical composition of claim 50 , comprising:

Monoglycerides (MG) (g/100 g sample)

≧0.7

Triglycerides (TG) (g/100 g sample)

≧3.00

Free Fatty Acids (FFA) (g/100 g sample)

≧5.00

Cholesterol (g/100 g sample)

≦2.00

Total Phospholipids (PL) (g/100 g sample)

≧40.00

Phosphatidyl Ethanolamine (PE) (g/100 g sample)

≧2.50

Phosphatidyl Inositol (PI) (g/100 g sample)

≧0.20

Phosphatidyl Serine (PS) (g/100 g sample)

≧0.20

Phosphatidyl Choline (PC) (g/100 g sample)

≧35.00

Sphingomyelin (g/100 g sample)

≧0.50

Vitamin A (μg/100 ml)

≧1,400

Vitamin E (μg/100 ml)

≧15

Beta-Carotene (μg/100 ml)

≧1,600

Astaxanthin (mg/100 ml)

≧10

Canthaxanthin (mg/100 ml)

≧10

Flavonoid (mg/100 ml)

≧7.0.

65. The nutraceutical composition of claim 47 , wherein one of R1 and R2 is EPA and the other is DHA.

66. The nutraceutical composition of claim 47 , wherein R1 and R2 is EPA.

67. The nutraceutical composition of claim 47 , wherein R1 and R2 is DHA.

68. The nutraceutical composition of claim 47 , wherein the extract further comprises an antioxidant.

69. The nutraceutical composition of claim 68 , wherein the antioxidant is selected from the group consisting of vitamin A, vitamin E, carotenoid, beta-carotene, astaxanthin, canthaxanthin, flavonoids, and mixtures thereof.

70. A cosmetic preparation comprising a krill extract comprising: a phospholipid of the formula (I),

wherein R1 and R2, each together with the respective carboxyl groups to which each is attached, each independently represents a docosahexaenoic acid (DHA) or an eicosapentaenoic acid (EPA) residue, and X is —CH 2 CH 2 NH 3 , —CH 2 CH 2 N(CH 3 ) 3 , or

 and

wherein the extract is suitable for human consumption.

71. The cosmetic preparation of claim 70 , wherein the topical cosmetic product is one or more of a moisturizing cream and a sun-block product.

72. The extract according to claim 70 , wherein the extract has a total phospholipid concentration in an amount of about 40% w/w, wherein about represents ±10%.

73. The extract according to claim 70 , wherein the extract has a total phospholipid concentration in an amount of about 45% w/w, wherein about represents ±20%.

74. The cosmetic preparation of claim 70 , wherein the extract further comprises an additional lipid, wherein the additional lipid is selected from the group consisting of monoglycerides, triglycerides, cholesterols, mixtures thereof, and free fatty acids.

75. The cosmetic preparation of claim 70 , wherein the extract has a concentration of free fatty acids of about 5% w/w of the lipids in the extract.

76. The cosmetic preparation of claim 70 , wherein the extract further comprises polyunsaturated fatty acids which comprise at least 15% w/w of the lipids in the extract.

77. The cosmetic preparation of claim 70 , wherein the extract further comprises polyunsaturated fatty acids which comprise at least 40% w/w of the lipids in the extract.

78. The cosmetic preparation of claim 70 , wherein the extract further comprises polyunsaturated fatty acids which comprise at least 45% w/w of the lipids in the extract.

79. The cosmetic preparation of claim 76 , 77 , or 78 , wherein the polyunsaturated fatty acids are omega-3 fatty acids.

80. The cosmetic preparation of claim 70 , wherein DHA and EPA comprise at least 32% w/w of the lipids in the extract.

81. The cosmetic preparation of claim 70 , wherein DHA and EPA comprise at least 35% w/w of the lipids in the extract.

82. The cosmetic preparation of claim 70 , wherein the extract further comprises a metal.

83. The cosmetic preparation of claim 82 , wherein the metal is zinc, selenium or a mixture thereof

84. The cosmetic preparation of claim 83 , wherein the zinc comprises at least 0.005mg/100g of the extract and the selenium comprises less than 3 mg/100g of the extract.

85. The cosmetic preparation of claim 74 , wherein the fatty acid composition of the lipids in the extract is about:

Total

Phosphatidyl-

Phosphatidyl-

Phospholipid

choline

ethanolamine

Fatty Acids

Fatty Acid %

Fatty Acid %

Fatty Acid %

C14:0 MYRISTIC

2

2

0.7

C14:1 MYRISTOLEIC

1

C15:0

0.2

0.3

0.3

PENTADECANOIC

C16:0 PALMITIC

24

27

24

C16:1 PALMITOLEIC

2

2

0.7

C18:0 STEARIC

1

1

3

C18:1 OLEIC

9

12

24

C18:2n6 LINOLEIC

2

2

0.8

C18:3n6 GLA

1

0.3

C18:3n3 ALA

1

1

C18:4n3 OTA

2

2

0.3

C20:0 ARACHIDIC

C20:1 cis-11-

0.5

0.6

0.7

EICOSENOIC

C20:2n6

EICOSADIENOIC

C20:3n6 METHYL ETA

0.2

C20:4n6 ARACHIDONIC

0.6

0.7

0.6

C20:3n3 Homo-γ-

LINOLENIC

C20:4n3

C20:5n3 EPA

27

32

13

C22:0 BEHENIC

C22:1 ERUCIC

1

1.5

C22:2n6

C22:4n6

C22:5n6 METHYL DPA

C22:5n3 DPA

1.00

C22:6n3 DHA

25

14

32

C24:0 LIGNOCERIC

C24:1 NERVONIC

Total

100.0

100

100;

wherein about represents ±10%.

86. The cosmetic preparation of claim 85 , wherein the total fatty acid composition of all the lipids in the extract is:

Sample

%

Fatty Acid Composition

C14:0

≧3.00

C14:1

≧0.01

C15:0

≧0.3

C16:0

≧20.00

C16:1

≧3.25

C18:0

≧1.00

C18:1

≧10.00

C18:2n6

≧2.00

C18:3n6 GLA

≧0.04

C18:3n3 ALA

≧0.01

C18:4n3

≧1.50

C20:0

≧0.05

C20:1

≧1.00

C20:2n6

≧0.05

C20:3n6

≧0.05

C20:4n6

≧0.50

C20:3n3

≧0.01

C20:4n3

≧0.20

C20:5n3 EPA

≧25.00

C22:0

≧0.01

C22:1

≧1.50

C22:2n6

≧0.03

C22:4n6

≧0.01

C22:5n6

≧0.01

C22:5n3 DPA

≧0.50

C22:6n3 DHA

≧10.00

C24:0

≧0.01

C24:1

≧0.05.

87. The cosmetic preparation of claim 86 , wherein the total fatty acid composition of all the lipids is:

Saturated (g/100 g lipid)

≧22.00

Monounsaturated (g/100 g lipid)

≧11.00

Polyunsaturated (g/100 g lipid)

≧35.00

Omega-3 (g/100 g lipid)

≧30.00

Omega-6 (g/100 g lipid)

≧1.00.

88. The nutraceutical composition of claim 74 , comprising:

Monoglycerides (MG) (g/100 g sample)

≧0.7

Triglycerides (TG) (g/100 g sample)

≧3.00

Free Fatty Acids (FFA) (g/100 g sample)

≧5.00

Cholesterol (g/100 g sample)

≦2.00

Total Phospholipids (PL) (g/100 g sample)

≧40.00

Phosphatidyl Ethanolamine (PE) (g/100 g sample)

≧2.50

Phosphatidyl Inositol (PI) (g/100 g sample)

≧0.20

Phosphatidyl Serine (PS) (g/100 g sample)

≧0.20

Phosphatidyl Choline (PC) (g/100 g sample)

≧35.00

Sphingomyelin (g/100 g sample)

≧0.50

Vitamin A (μg/100 ml)

≧1,400

Vitamin E (μg/100 ml)

≧15

Beta-Carotene (μg/100 ml)

≧1,600

Astaxanthin (mg/100 ml)

≧10

Canthaxanthin (mg/100 ml)

≧10

Flavonoid (mg/100 ml)

≧7.0.

89. The cosmetic preparation of claim 70 , wherein one of R1 and R2 is EPA and the other is DHA.

90. The cosmetic preparation of claim 70 , wherein R1 and R2 is EPA.

91. The cosmetic preparation of claim 70 , wherein R1 and R2 is DHA.

92. The cosmetic preparation of claim 70 , wherein the extract further comprises an antioxidant.

93. The cosmetic preparation of claim 92 , wherein the antioxidant is selected from the group consisting of vitamin A, vitamin E, carotenoid, beta-carotene, astaxanthin, canthaxanthin, flavonoids, and mixtures thereof.

94. An Antarctic krill oil extract comprising: a phospholipid of the formula (I),

wherein:

R1 and R2, each together with the respective carboxyl groups to which each is attached, each independently represents a docosahexaenoic acid (DHA) or an eicosapentaenoic acid (EPA) residue, and X is —CH 2 CH 2 NH 3 , —CH 2 CH 2 N(CH 3 ) 3 , or

the extract is extracted under conditions suitable for preserving an effective amount of a phospholipid having two independently selected fatty acid chains within the same molecule selected from EPA and DHA;

the extract comprises phospholipids in an amount of at least 40% w/w;

the extract comprises omega-3 fatty acids in an amount of at least 15% w/w;

the extract comprises astaxanthin and

the extract is suitable for human consumption.

Assignments (4)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 7, 2017
From: NEPTUNE TECHNOLOGIES & BIORESSOURCES, INC.
To: AKER BIOMARINE ANTARCTIC AS
Reel/Frame 043525/0925 →
RELEASE OF SECURITY INTEREST Recorded Aug 24, 2017
From: BANK AND CLIENTS PLC
To: NEPTUNE TECHNOLOGIES & BIORESSOURCES INC.
Reel/Frame 043389/0273 →
MORTGAGE Recorded Apr 19, 2016
From: NEPTUNE TECHNOLOGIES & BIORESSOURCES INC.
To: BANK AND CLIENTS PLC
Reel/Frame 038463/0304 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 11, 2011
From: SAMPALIS, FOTINI
To: NEPTUNE TECHNOLOGIES & BIORESSOURCES, INC.
Reel/Frame 027041/0266 →