Phospholipid compositions enriched for palmitoleic, myristoleic or lauroleic acid, their preparation and their use in treating metabolic and cardiovascular disease

1. A phospholipid composition comprising one or more compounds of Formula

wherein R 1 and R 2 are each independently selected from —COOH or an acyl radical of any fatty acid, wherein at least one of R 1 and R 2 is palmitoleoyl, myristoleoyl or lauroleoyl; and R 3 is selected from the group consisting of H, —CH 2 CH 2 NH 3 , —CH 2 CH 2 N(CH 3 ) 3 , CH 2 CHNH 3 CO 2 H, and (CHOH) 6 , characterized in that palmitoleic acid, myristoleic acid or lauroleic acid constitutes at least 15% weight percentage based on the total fatty acid content of the total phospholipid fraction of the composition.

2. The composition of claim 1 wherein at least one of R 1 and R 2 are palmitoleoyl.

3. The composition of claim 1 , wherein R 1 and R 2 are each palmitoleoyl.

4. The composition of claim 2 , wherein at least one palmitoleoyl is in the cis configuration.

5. The composition of claim 2 , wherein at least one palmitoleoyl is in the trans configuration.

6. The composition of claim 1 , wherein at least one of R 1 and R 2 are myristoleoyl.

7. The composition of claim 1 , wherein at least one of R 1 and R 2 are lauroleoyl.

8. The composition of claim 1 , wherein R 3 is —CH 2 CH 2 N(CH 3 ) 3 .

9. The composition of claim 1 , wherein palmitoleic acid, myristoleic acid or lauroleic acid constitutes at least 20%, at least 25%, at least 30%, at least 40% or even at least 50% weight percentage based on the total fatty acid content of the total phospholipid fraction of the composition.

10. The composition of claim 9 , wherein palmitoleic acid, myristoleic acid or lauroleic acid constitutes between 30% and 60% weight percentage based on the total fatty acid content of the total phospholipid fraction of the composition.

11. The composition of claim 1 , wherein the bioavailability of palmitoleic acid, myristoleic acid or lauroleic acid is increased as compared to purified triglycerides having substantially the same weight percentage of palmitoleic acid, myristoleic acid or lauroleic acid.

12. A method for producing a composition of claim 1 comprising:

(a) providing oil obtained from a palmitoleic acid-, myristoleic acid- or lauroleic acid rich source

(b) esterifying said oil with ethanol to form ethyl esters and

(c) incubating said ethyl esters in the presence of a phospholipid, a 1,3-regiospecific lipase having phospholipase activity and/or phospholipase A2 (PLA2) under conditions suitable to catalyze acidolysis between the ethyl esters and the phospholipid to produce a palmitoleic acid-, myristoleic acid- or lauroleic acid-enriched phospholipid composition.

13. The method of claim 12 wherein the 1,3-regiospecific lipase is selected from the group consisting of: Rhizomucor miehei lipase, Thermomyces lanuginose lipase, Rhizopus delemar lipase, Mucor javanicus lipase, Rhizopus orizae lipase, and Candida cylindracea lipase.

14. The method of claim 12 wherein the oil is obtained from a palmitoleic acid-rich source and a palmitoleic acid-enriched phospholipid composition is produced.

15. A pharmaceutical composition comprising a composition according to claim 1 and a pharmaceutically acceptable carrier.

16. A method for treating a disease or disorder comprising administering an effective amount of a composition according to claim 15 to a subject in need thereof, wherein the disease or disorder is selected from the group consisting of: cardiovascular disease, low HDL levels, high LDL levels, hypertriglyceridemia, hypercholesterolemia, atherosclerosis, obesity, prostate cancer, and type 2 diabetes.

17. The method of claim 16 , wherein the subject is a human.

18. The method of claim 17 , wherein the human is a male.

19. The method of claim 17 , wherein the human is a female.