Conjugated fatty acids and related compounds

• US 20010023259A1
• Filed: 12/18/2000
• Published: 09/20/2001
• Est. Priority Date: 12/18/1999
• Status: Abandoned Application

• Current Assignee: Natural Asa
• Original Assignee: Natural Asa
• Inventors: Slabas, Antoni Ryszard, Christie, William Walker, Simon, Josiah William
• Application Number:
  US09/740,145
• Publication Number:
  US 20010023259A1
• Time in Patent Office: Days
• US Class Current: 514/560
• CPC Class Codes: A23D 9/007 characterised by ingredients other than fatty acid triglycerides
• CPC Class Codes: A61K 31/202 having three or more double bonds, e.g. linolenic eicosanoids, e.g. leukotrienes A61K31/557
• CPC Class Codes: A61P 3/02 Nutrients, e.g. vitamins, minerals
• CPC Class Codes: A61P 9/10 for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
• CPC Class Codes: C12P 7/6427 Polyunsaturated fatty acids [PUFA], i.e. having two or more double bonds in their backbone
• CPC Class Codes: C12P 7/6431 Linoleic acids [18:2[n-6]]
• CPC Class Codes: C12P 7/6436 Fatty acid esters
• CPC Class Codes: C12P 7/6458 by transesterification, e.g. interesterification, ester interchange, alcoholysis or acidolysis
• CPC Class Codes: C12P 7/6472 containing polyunsaturated fatty acid [PUFA] residues, i.e. having two or more double bonds in their backbone

Abstract

It has been demonstrated that conjugated linoleic acid isomers with the first double bond in position 9 (cis) or 10 (trans), added exogenously, can be desaturated in position 6 by the cyanobacterium Spirulina platensis. The metabolites, 6-cis, 9-cis, 11-trans-octadecatrienoic and 6-cis,10-trans,12-cis-octadecatrienoic acids, which have not previously been characterized, were isolated by a combination of chromatographic techniques and the structures were confirmed by gas chromatography-mass spectrometry in the form of picolinyl ester and dimethyloxazoline derivatives.

Claims

1. A composition comprising a conjugated octadecatrienoic acid moiety, wherein said conjugated octadecatrienoic acid moiety is desaturated at position 6.

2. The composition of

claim 1

, wherein said conjugated octadecatrienoic acid moiety is selected from the group consisting of c-6, c-9, t-11 octadecatrienoic acid, c-6, c-9, c-1 octadecatrienoic acid, c-6, t-9, t-11 octadecatrienoic acid, c-6, t-9, c-11 octadecatrienoic acid, c-6, t-10, c-12, octadecatrienoic acid, c-6, c-10, t-12, octadecatrienoic acid, c-6, t-10, t-12, octadecatrienoic acid, and c-6, c-10, c-12, octadecatrienoic acid.

3. The composition of

claim 1

, wherein said conjugated octadecatrienoic acid moiety is a free fatty acid.

4. The composition of

claim 1

, wherein said conjugated octadecatrienoic acid moiety is an ester.

5. The composition of

claim 4

, wherein said ester is selected from the group consisting of methyl and ethyl esters.

6. The composition of

claim 1

, wherein said moiety is covalently attached to a glycerol.

7. The composition of

claim 1

, further comprising an antioxidant.

8. The composition of

claim 1

, further comprising a food product.

9. A pharmaceutical composition comprising an excipient and a conjugated octadecatrienoic acid moiety, wherein said conjugated octadecatrienoic acid moiety is desaturated at position 6.

10. The composition of

claim 9

, wherein said conjugated octadecatrienoic acid moiety is selected from the group consisting of c-6, c-9, t-11 octadecatrienoic acid, c-6, c-9, c-11 octadecatrienoic acid, c-6, t-9, t-11 octadecatrienoic acid, c-6, t-9, c-11 octadecatrienoic acid, c-6, t-10, c-12, octadecatrienoic acid, c-6, c-10, t-12, octadecatrienoic acid, c-6, t-10, t-12, octadecatrienoic acid, and c-6, c-10, c-12, octadecatrienoic acid.

11. The composition of

claim 9

, wherein said conjugated octadecatrienoic acid moiety is a free fatty acid.

12. The composition of

claim 9

, wherein said conjugated octadecatrienoic acid moiety is an ester.

13. The composition of

claim 12

, wherein said ester is selected from the group consisting of methyl and ethyl esters.

14. The composition of

claim 9

, wherein said moiety is covalently attached to glycerol.

15. The composition of

claim 9

, further comprising an antioxidant.

16. A composition comprising a conjugated octadecatrienoic acid moiety made by the process comprising:

a) providing a conjugated octadecadienoic acid and a delta-6 desaturase; and

b) exposing said conjugated octadecadienoic acid to said delta-6 desaturase under conditions such that a conjugated octadecatrienoic moiety desaturated at position 6 is produced.

17. A method for preparing a conjugated octadecatrienoic acid moiety comprising:

a) providing a conjugated octadecadienoic acid and a delta-6 desaturase; and

b) exposing said conjugated octadecadienoic acid to said delta-6 desaturase under conditions such that a conjugated octadecatrienoic moiety desaturated at position 6 is produced.

18. The method of

claim 17

, wherein said conjugated octadecadienoic acid is selected from the group consisting of c9,t11-, t9,c11-, t9,t11-, c9,c11-, t10,c12-, c10,t12-c10,c12-, and t10,t12-octadecadienoic acids.

19. The method of

claim 17

, wherein said delta-6 desaturase is derived from Spirlina platensis.

20. The method of

claim 17

, wherein said exposing step further comprises incubating said octadecadienoic acid with a culture of Spirlina platensis.

21. The method of

claim 20

, wherein said Spirulina platensis is a strain selected from the group consisting of PCC8005, PCC6313, PCC7345, and PCC7939.

22. The method of

claim 17

, further comprising step

c) purifying said conjugated octadecatrienoic moiety.

23. A composition comprising a delta-6 desaturase, octadecadienoic acid, and an octadecatrienoic moiety.

24. The composition of

claim 23

, further comprising a culture of Spirlina platensis.

25. A method of altering arachidonic acid metabolism in a subject comprising:

a) providing a subject and a conjugated octadecatrienoic acid moiety, wherein said conjugated octadecatrienoic acid moiety is desaturated at position 6; and

b) administering said conjugated octadecatrienoic acid moiety to said subject under conditions such that an arachidonic acid analog is formed.

26. The method of

claim 25

, wherein said conjugated octadecatrienoic acid moiety is selected from the group consisting of c-6, c-9, t-11 octadecatrienoic acid, c-6, c-9, c-11 octadecatrienoic acid, c-6, t-9, t-11 octadecatrienoic acid, c-6, t-9, c-11 octadecatrienoic acid, c-6, t-10, c-12, octadecatrienoic acid, c-6, c-10, t-12, octadecatrienoic acid, c-6, t-10, t-12, octadecatrienoic acid, and c-6, c-10, c-12, octadecatrienoic acid.

27. The method of

claim 25

, wherein said arachidonic acid analog is selected from the group consisting of c-5, c-8, c-11, t-13 eicosatetraenoic acid and c-5, c-8, t-12, c-14 eicosatetraenoic acid.

28. The method of

claim 25

, wherein said conjugated octadecatrienoic moiety is provided at a dose of about 10 mg to 10 g per day.

29. The method of

claim 25

, wherein said conjugated octadecatrienoic moiety is provided as an acylglycerol.

30. The method of

claim 25

, wherein said conjugated octadecatrienoic moiety is provided as an alkyl ester.

31. The method of

claim 25

, wherein said conjugated octadecatrienoic moiety is provided as a salt.

32. A compound

R₁—

O—

R₂

wherein R₁ is selected from the group consisting of c-6, c-9, t-11 octadecatrienoyl, c-6, c-9, c-11 octadecatrienoyl, c-6, t-9, t-11 octadecatrienoyl, c-6, t-9, c-11 octadecatrienoyl, c-6, t-10, c-12, octadecatrienoyl, c-6, c-10, t-12, octadecatrienoyl, c-6, t-10, t-12, octadecatrienoyl, and c-6, c-10, c-12, octadecatrienoyl and

R₂ is selected from the group consisting of hydrogen, alkyl, glycerol, and phosphoglycerol.

33. The compound of

claim 32

, wherein said alkyl is selected from the group consisting of methyl, ethyl and propyl.

34. A method of producing conjugated octadecatrienoic acid comprising

a) providing gamma-linoleic acid and a catalyst;

and

b) reacting said gamma-linolenic acid with said catalyst under conditions such that c6, t10, c12 octadecatrienoic acid is produced.

35. The method of

claim 34

, wherein said gamma-linolenic acid is provided in borage oil.