Methods for producing bioeffective krill oil compositions

• US 9,375,453 B2
• Filed: 09/06/2013
• Issued: 06/28/2016
• Est. Priority Date: 03/28/2007
• Status: Active Grant

• Current Assignee: Aker BioMarine Antarctic AS (Aker BioMarine ASA)
• Original Assignee: Aker BioMarine Antarctic AS (Aker BioMarine ASA)
• Inventors: Bruheim, Inge, Tilseth, Snorre, Mancinelli, Daniele
• Primary Examiner(s): Ware, Debbie K
• Application Number:
  US14/020,162
• Publication Number:
  US 20140005421A1
• Time in Patent Office: 1,026 Days
• US Class Current: 1/1
• CPC Class Codes: A23L 33/115 Fatty acids or derivatives thereof; Fats or oils
• CPC Class Codes: A23V 2002/00 Food compositions, function of food ingredients or processes for food or foodstuffs
• CPC Class Codes: A61K 2300/00 Mixtures or combinations of active ingredients, wherein at least one active ingredient is fully defined in groups A61K31/00 - A61K41/00
• CPC Class Codes: A61K 31/122 having the oxygen directly attached to a ring, e.g. quinones, vitamin K1, anthralin
• CPC Class Codes: A61K 31/20 having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids
• CPC Class Codes: A61K 31/202 having three or more double bonds, e.g. linolenic eicosanoids, e.g. leukotrienes A61K31/557
• CPC Class Codes: A61K 31/215 of carboxylic acids
• CPC Class Codes: A61K 31/23 of acids having a carboxyl group bound to a chain of seven or more carbon atoms
• CPC Class Codes: A61K 31/235 having an aromatic ring attached to a carboxyl group
• CPC Class Codes: A61K 31/575 substituted in position 17 beta by a chain of three or more carbon atoms, e.g. cholane, cholestane, ergosterol, sitosterol
• CPC Class Codes: A61K 31/683 Diesters of a phosphorus acid with two hydroxy compounds, e.g. phosphatidylinositols
• CPC Class Codes: A61K 31/685 one of the hydroxy compounds having nitrogen atoms, e.g. phosphatidylserine, lecithin
• CPC Class Codes: A61K 35/612 Crustaceans, e.g. crabs, lobsters, shrimps, krill or crayfish; Barnacles
• CPC Class Codes: A61K 45/06 Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
• CPC Class Codes: A61K 9/0053 Mouth and digestive tract, i.e. intraoral and peroral administration rectal administration A61K9/0031
• CPC Class Codes: A61K 9/48 Preparations in capsules, e.g. of gelatin, of chocolate A61K9/0004 takes precedence; bite capsules A61K9/0056
• CPC Class Codes: A61K 9/4825 Proteins, e.g. gelatin gelatin capsule shells with substantial amounts of other macromolecular substances A61K9/4816
• CPC Class Codes: A61K 9/4858 Organic compounds
• CPC Class Codes: A61P 3/02 Nutrients, e.g. vitamins, minerals
• CPC Class Codes: C11B 3/006 by extraction

Abstract

New krill oil compositions are disclosed as having high amounts of phospholipids, astaxanthin esters and/or omega-3 contents. The krill oils are obtained from krill meal using supercritical fluid extraction in a two stage process. Stage 1 removes the neutral lipid by extracting with neat supercritical CO₂ or CO₂ plus approximately 5% of a co-solvent. Stage 2 extracts the actual krill oils by using supercritical CO₂ in combination with approximately 20% ethanol. The krill oil materials obatined are compared with commercially available krill oil and found to be more bioeffective in a number of areas such as anti-inflammation, anti-oxidant effects, improving insulin resistances and improving blood lipid profile.

Claims

1. A method of production of polar krill oil from Euphausia superba comprising:

a) treating the Euphausia superba to denature lipases and phospholipases to provide a denatured krill product;

b) contacting the denatured krill product with a polar solvent to extract a polar krill oil comprising phospholipids, said polar krill oil comprises greater than about 3% ether phospholipids w/w of said polar krill oil;

from about 27% to 50% non-ether phospholipids w/w of said polar krill oil so that the amount of total phospholipids is from about 30% to 60% w/w of said polar krill oil;

from about 20% to 50% triglycerides w/w of said polar krill oil, and astaxanthin esters in amount of greater than about 100 mg/kg of said polar krill oil; and

c) formulating said polar krill oil with a carrier for oral consumption.

2. The method of claim 1, wherein said polar krill oil comprises greater than about 40% phosphatidylcholine w/w of said polar krill oil.

3. The method of claim 1, wherein said polar krill oil comprises greater than about 45% phosphatidylcholine w/w of said polar krill oil.

4. The method of claim 1, wherein said polar krill oil comprises at least 36% omega-3 fatty acids as a percentage of total fatty acids in said polar krill oil.

5. The method of claim 1, wherein said method further comprises formulating said polar krill oil for oral consumption by a human.

6. The method of claim 5, wherein said formulating comprises encapsulating said polar krill oil in a capsule.

7. The method of claim 1, wherein said polar krill oil contains greater than about 200 mg/kg astaxanthin esters.

8. The method of claim 1, wherein said polar krill oil contains greater than about 300 mg/kg astaxanthin esters.

9. The method of claim 1, wherein said polar krill oil contains greater than about 400 mg/kg astaxanthin esters.

10. The method of claim 1, wherein said polar krill oil comprises from about 20% to 35% omega-3 fatty acids as a percentage of total fatty acids in said composition polar krill oil.

11. The method of claim 10, wherein from about 70% to 95% of said omega-3 fatty acids are attached to said phospholipids.

12. The method of claim 6, wherein said polar krill oil is encapsulated in a soft gel capsule.

13. The method of claim 1, further comprising combining said polar krill oil with a plant phytonutrient.

14. The method of claim 1, wherein said polar krill oil comprises greater than about 4% w/w ether phospholipids.

15. The method of claim 14, wherein said polar krill oil comprises greater than about 200 mg/kg astaxanthin esters.

16. The method of claim 14, wherein said polar krill oil comprises greater than about 300 mg/kg astaxanthin esters.

17. The method of claim 15, wherein said polar krill oil comprises from about 20% to 35% omega-3 fatty acids as a percentage of total fatty acids in said polar krill oil.

18. The method of claim 17, wherein from about 70% to 95% of said omega-3 fatty acids are attached to said phospholipids.

19. The method of claim 14, wherein said polar krill oil comprises greater than about 400 mg/kg astaxanthin esters.

20. The method of claim 19, wherein said polar krill oil comprises from about 20% to 35% omega-3 fatty acids as a percentage of total fatty acids in said polar krill oil.

21. The method of claim 20, wherein from about 70% to 95% of said omega-3 fatty acids are attached to said phospholipids.

22. The method of claim 16, further comprising combining said polar krill oil with a plant phytonutrient.

23. The method of claim 1, wherein said polar krill oil comprises greater than about 5% w/w ether phospholipids.

24. The method of claim 23, wherein said polar krill oil comprises greater than about 200 mg/kg astaxanthin esters.

25. The method of claim 23, wherein said polar krill oil comprises greater than about 300 mg/kg astaxanthin esters.

26. The method of claim 24, wherein said polar krill oil comprises from about 20% to 35% omega-3 fatty acids as a percentage of total fatty acids in said polar krill oil.

27. The method of claim 26, wherein from about 70% to 95% of said omega-3 fatty acids are attached to said phospholipids.

28. The method of claim 23, wherein said polar krill oil comprises greater than about 400 mg/kg astaxanthin esters.

29. The method of claim 24, further comprising combining said polar krill oil with a plant phytonutrient.

30. The method of claim 1, wherein the treating step occurs on a ship.

31. The method of claim 1, wherein said Euphausia superba is freshly caught.

32. The method of claim 1, wherein said treating is a heat treatment.

33. A method of production of polar krill oil from Euphausia superba comprising:

a) treating the Euphausia superba to denature lipases and phospholipases to provide a denatured krill product;

b) contacting the denatured krill product with a polar solvent to extract a polar krill oil comprising phospholipids, and said polar krill oil comprises greater than about 3% ether phospholipids w/w of said polar krill oil;

from about 27% to 50% non-ether phospholipids w/w of said polar krill oil so that the amount of total phospholipids is from about 30% to 60% w/w of said polar krill oil, from about 20% to 50% triglycerides w/w of said polar krill oil, and astaxanthin esters in amount of greater than about 100 mg/kg of said polar krill oil; and

c) encapsulating said polar krill oil in a soft gel capsule.

34. The method of claim 33, wherein said Euphausia superba is freshly caught.

35. The method of claim 33, wherein said treating is a heat treatment.

36. The method of claim 33, wherein the treating step occurs on a ship.

37. The method of claim 33, wherein said polar krill oil comprises greater than about 40% phosphatidylcholine w/w of said polar krill oil.

38. The method of claim 33, wherein said polar krill oil comprises greater than about 45% phosphatidylcholine w/w of said polar krill oil.

39. The method of claim 33, wherein said polar krill oil comprises at least 36% omega-3 fatty acids as a percentage of total fatty acids in said polar krill oil.

40. The method of claim 33, wherein said polar krill oil contains greater than about 200 mg/kg astaxanthin esters.

41. The method of claim 33, wherein said polar krill oil contains greater than about 300 mg/kg astaxanthin esters.

42. The method of claim 33, wherein said polar krill oil contains greater than about 400 mg/kg astaxanthin esters.

43. The method of claim 33, wherein said polar krill oil comprises from about 20% to 35% omega-3 fatty acids as a percentage of total fatty acids in said polar krill oil.

44. The method of claim 43, wherein from about 70% to 95% of said omega-3 fatty acids are attached to said phospholipids.

45. The method of claim 33, further comprising combining said polar krill oil with a plant phytonutrient.

46. The method of claim 33, wherein said polar krill oil comprises greater than about 4% w/w ether phospholipids.

47. The method of claim 46, wherein said polar krill oil comprises greater than about 200 mg/kg astaxanthin esters.

48. The method of claim 46, wherein said polar krill oil comprises greater than about 300 mg/kg astaxanthin esters.

49. The method of claim 46, wherein said polar krill oil comprises from about 20% to 35% omega-3 fatty acids as a percentage of total fatty acids in said polar krill oil.

50. The method of claim 49, wherein from about 70% to 95% of said omega-3 fatty acids are attached to said phospholipids.

51. The method of claim 46, wherein said polar krill oil comprises greater than about 400 mg/kg astaxanthin esters.

52. The method of claim 51, wherein said polar krill oil comprises from about 20% to 35% omega-3 fatty acids as a percentage of total fatty acids in said polar krill oil.

53. The method of claim 52, wherein from about 70% to 95% of said omega-3 fatty acids are attached to said phospholipids.

54. The method of claim 46, further comprising combining said polar krill oil with a plant phytonutrient.

55. The method of claim 33, wherein said polar krill oil comprises greater than about 5% w/w ether phospholipids.

56. The method of claim 55, wherein said polar krill oil comprises greater than about 200 mg/kg astaxanthin esters.

57. The method of claim 55, wherein said polar krill oil comprises greater than about 300 mg/kg astaxanthin esters.

58. The method of claim 56, wherein said polar krill oil comprises from about 20% to 35% omega-3 fatty acids as a percentage of total fatty acids in said polar krill oil.

59. The method of claim 58, wherein from about 70% to 95% of said omega-3 fatty acids are attached to said phospholipids.

60. The method of claim 55, wherein said polar krill oil comprises greater than about 400 mg/kg astaxanthin esters.

61. The method of claim 55, further comprising combining said polar krill oil with a plant phytonutrient.