Phospholipid compositions and their preparation

Patent metadata

Field	Value
Publication number	US-2016339062-A1
Application number	US-201515110554-A
Country	US
Kind code	A1
Filing date	Jan 9, 2015
Priority date	Jan 10, 2014
Publication date	Nov 24, 2016
Grant date	—

Abstract

The invention provides improved processes for extracting and preparing polar lipids (in particular, desirable phospholipids) from krill and other biological sources. The inventors have discovered processes through which it is possible to extract phospholipids to give high phospholipid content and a reduction of undesired components.

First claim

1 . A composition comprising a mixture of phospholipid compounds of formula (I):

wherein:
R 1 and R 2 are each independently selected from a fatty acid moiety of formula —COC n H m , a fatty acid moiety of formula —CH 2 C n H m , and —H;
R 1 and R 2 include omega-3 fatty acid moieties, such that at least 30% by weight of the phospholipid compounds is composed of omega-3 fatty acid moieties;
at least 90% by weight of total omega-3 fatty acid moieties are at position R 2 ;
R 1 and R 2 are not both —H in a phospholipid compound, and R 1 or R 2 is —H in less than 3% by weight of the compounds of formula (I);
R 3 is selected from —H, a choline moiety, an ethanolamine moiety, a N-acetylethanolamine moiety, an inositol moiety, and a serine moiety; and
R 3 is a choline moiety in at least 85% by number of the compounds of formula (I).

and wherein the composition also has one or more of the following properties:
(a) at least 85% by weight of the composition consists of phospholipid compounds of formula (I), optionally wherein the composition is substantially free from acetone;
(b) the weight ratio of C16:0/C14:0 fatty acid moieties in the mixture is between 10:1 and 18:1 and/or the weight ratio of C18:4 n-3/C18:3 n-3 fatty acid moieties is between 1:1 and 3:2;
(c) the composition includes less than 300 μg astaxanthins per gram of phospholipid;
(d) the composition comprises less than 0.01% by weight trimethylamine N-oxide;
(e) the composition comprises less than 0.01% by weight homarine;
(f) the composition includes less than 5% by weight water;
(g) the composition has less than about 0.03% by weight PUFA polymers
(h) the mixture includes both phospholipids where R 1 is a fatty acid moiety of formula —COC n H m and phospholipids where R 1 is a fatty acid moiety of formula —CH 2 C n H m ;
(i) the mixture includes both phospholipids where R 1 is an omega-3 fatty acid moiety and phospholipids where R 2 is an omega-3 fatty acid moiety;
(j) the composition includes less than 5% by weight sphingomyelin;
(k) the composition is free from chloroform and hexane; and/or
(l) less than 0.9% by weight of phospholipids in the composition is formed of compounds where R 1 or R 2 is —H, or more than 1.1% by weight of phospholipids in the composition is formed of compounds where R 1 or R 2 is —H.

2 . The composition of claim 1 , wherein at least 85% by weight of the composition consists of phospholipid compounds of formula (I) and the composition is substantially free from acetone.

3 . The composition of claim 1 , having 2 or more of properties (a) to (l).

4 . The composition of claim 3 , having 3 or more of properties (a) to (l).

5 . The composition of claim 1 , wherein less than 0.9% by weight of phospholipids in the composition is formed of compounds where R 1 or R 2 is —H.

6 . The composition of claim 1 , having at least properties (h) and (i).

7 . The composition of claim 6 , having at least properties (a), (c), (d), (e), (g) and (j).

8 . The composition of claim 7 , having at least properties (a), (b), (c), (d), (e), (g) and (j).

9 . The composition of claim 6 , having at least properties (a), (c), (d), (e), (f), (h), (j), and (k).

10 . The composition of claim 9 , having properties (a), (b) (c), (d), (e), (f), (h), (j), and (k), and wherein: with reference to property (h) fatty acid moieties of formula —CH 2 C n C m are either saturated or mono-unsaturated, and not polyunsaturated; the compounds of formula (I) include C16:0, C14:0, C18:4 n-3 and C18:3 n-3 fatty acid moieties at R 1 and/or R 2 ; the amount of water is less than 2% by weight; the composition has less than 1% by weight free fatty acids; the composition has less than 0.005% by weight trimethylamine; the composition is free from canthaxanthin and flavonoid; and, optionally, wherein the phospholipids of formula (I) include EPA and DHA moieties in a molar ratio (EPA:DHA) from 1.8:1 to 2.2:1.

11 . (canceled)

12 . A composition comprising ( 1 ) a pharmaceutically-acceptable solvent and (2) a mixture of phospholipid compounds of formula (I), as defined in claim 1 , and further having one or more of properties (b) to (l) as defined in claim 1 , wherein the phospholipid compounds of formula (I) are dissolved, suspended or emulsified in the pharmaceutically-acceptable solvent, and wherein the composition is liquid when at 20° C.

13 - 26 . (canceled)

Assignees

• Aker Biomarine Antarctic As

Inventors

• Myhren Finn
• Hoem Nils
• Thøgersen Hâvard

Classifications

• A61K31/575

  substituted in position 17 beta by a chain of three or more carbon atoms, e.g. cholane, cholestane, ergosterol, sitosterol · CPC title

• A61K31/201

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

• A61K31/685

  one of the hydroxy compounds having nitrogen atoms, e.g. phosphatidylserine, lecithin · CPC title

• A61K31/122

  having the oxygen directly attached to a ring, e.g. quinones, vitamin K1, anthralin · CPC title

• A61K35/612 Primary

  Crustaceans, e.g. crabs, lobsters, shrimps, krill or crayfish; Barnacles · CPC title