IP Library › Patent Application 15935913

Patent Application

App. No. 15/935,913

OILS WITH ANTI-INFLAMMATORY ACTIVITY CONTAINING NATURAL SPECIALIZED PRORESOLVING MEDIATORS AND THEIR PRECURSORS

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Patent No.: US None
App. No.: 15/935,913

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Abstract

The present invention encompasses oils that have anti-inflammatory or resolution-stimulating activity that contain or are enriched with Specialized Proresolving Mediators (SPM) or SPM precursors, which originate from an oil obtained from organisms containing long chain omega-3 polyunsaturated fatty acids, such as fish, crustaceae, algae, and mollusks. The invention also encompasses a method for the production of these oils, and the utilization of the oils for nutritional supplements, pharmaceutical formulations, and cosmetic formulations, which can be employed for treating an inflammatory condition.

Claims (155)

1 . A method of producing a remodeled triglyceride having a glycerol backbone and three fatty acids chemically bound thereto, the method comprising: (a) providing an oil containing SPMs and/or SPM precursors including at least one of 18-HEPE, 17-HDHA, or 14-HDHA, (b) esterifying at least a portion of the SPMs and/or SPM precursors in the oil to form esterified SPMs and/or SPM precursors including one or more of 18-HEPE ethyl ester, 17-HDHA ethyl ester, or 14-HDHA ethyl ester, (c) purifying the oil to increase a relative amount of 18-HEPE ethyl ester, 17-HDHA ethyl ester, or 14-HDHA ethyl ester present in the oil, and (d) transesterfying the esterified SPMs and/or SPM precursors to form the remodeled triglyceride, wherein at least one of the fatty acids of the remodeled triglyceride comprises 18-HEPE, 17-HDHA, or 14-HDHA.

2 . The method of claim 1 wherein at least one of the fatty acids of the remodeled triglyceride is comprised of a long chain omega-3 polyunsaturated fatty acid.

3 . The method of claim 2 wherein the long chain omega-3 polyunsaturated fatty acid comprises EPA and/or DHA.

4 . The method of claim 1 wherein at least one of the fatty acids of the remodeled triglyceride is comprised of a SPM and/or an esterified SPM further selected from the group consisting of:

resolvin E1 (RvE1; 5S,12R,18R-trihydroxy-eicosa-6Z,8E,10E,14Z,16E-pentaenoic acid),

18S-resolvin E1 (18S-RvE1; 5S,12R,18S-trihydroxy-eicosa-6Z,8E,10E,14Z,16E-pentaenoic acid),

20-hydroxy-RvE 1 (5S,12R,18R,20-tetrahydroxy-eicosa-6Z,8E,10E,14Z,16E-pentaenoic acid),

resolvin E2 (RvE2; 5S,18-dihydroxy-eicosa-6E,8Z,11Z,14Z,16E-pentaenoic acid),

resolvin E3 (RvE3; 17,18R-dihydroxy-eicosa-5Z,8Z,11Z,13E,15E-pentaenoic acid),

18S-resolvin E3 (18S-RvE3; 17,18S-dihydroxy-eicosa-5Z,8Z,11Z,13E,15E-pentaenoic acid),

17,18-epoxy-eicosa-5Z,8Z,11Z,13E,15E-pentaenoic acid,

lipoxin A5 (LXA 5 ; 5S,6R,15S-trihydroxy-eicosa-7E,9E,11Z,13E,17Z-pentaenoic acid), 15-epi-lipoxin A5 (LXA 5 ; 5S,6R,15R-trihydroxy-eicosa-7E,9E,11Z,13E,17Z-pentaenoic acid),

maresin 1 (MaR1; 7R,14S-docosa-4Z,8E,10E,12Z,16Z,19Z-hexaenoic acid),

7S-maresin 1 (7S-MaR1; 7S,14S-docosa-4Z,8E,10E,12Z,16Z,19Z-hexaenoic acid),

7S,14S-diHDHA (7S,14S-dihydroxy-docosa-4Z,8E,10Z,12E,16Z,19Z-hexaenoic acid),

protectin D1 (PD1; 10R,17S-dihydroxy-docosa-4Z,7Z,11E,13E,15Z,19Z-hexaenoic acid),

10S,17S-HDHA (10S,17S-dihydroxy-docosa-4Z,7Z,11E,13Z,15E,19Z-hexaenoic acid),

14S,21S-diHDHA (14S,21S-dihydroxy-docosa-4Z,7Z,10Z,12E,16Z,19Z-hexaenoic acid), 14S,21R-diHDHA (14S,21R-dihydroxy-docosa-4Z,7Z,10Z,12E,16Z,19Z-hexaenoic acid),

14R,21S-diHDHA (14R,21S-dihydroxy-docosa-4Z,7Z,10Z,12E,16Z,19Z-hexaenoic acid),

14R,21R-diHDHA (14R,21R-dihydroxy-docosa-4Z,7Z,10Z,12E,16Z,19Z-hexaenoic acid),

13S,14S-epoxy-DHA (13S,14S-epoxy-docosa-4Z,7Z,9E,11E,16Z,19Z-hexaenoic acid),

16,17S-diHDHA (16,17S-dihydroxy-docosa-4Z,7Z,10Z,12E,14E,19Z-hexaenoic acid),

16,17-epoxy-DHA (16,17-epoxy-docosa-4Z,7Z,10Z,12E,14E,19Z-hexaenoic acid),

resolvin D1 (RvD1; 7S,8R,17S-trihydroxy-docosa-4Z,9E,11E,13Z,15E,19Z-hexaenoic acid),

resolvin D2 (RvD2; 7S,16R,17S-trihydroxy-docosa-4Z,8E,10Z,12E,14E,19Z-hexaenoic acid),

resolvin D3 (RvD3; 4S,11R,17S-trihydroxy-docosa-5Z,7E,9E,13Z,15E,19Z-hexaenoic acid),

resolvin D4 (RvD4; 4S,5,17S-trihydroxy-docosa-6E,8E,10Z,13Z,15E,19Z-hexaenoic acid),

resolvin D5 (RvD5; 7S,17S-dihydroxy-docosa-5Z,8E,10Z,13Z,15E,19Z-hexaenoic acid),

resolvin D6 (RvD6; 4S,17S-dihydroxy-docosa-5E,7Z,10Z,14Z,16E,19Z-hexaenoic acid),

aspirin-triggered resolvin D1 (AT-RvD1; 7S,8R,17R-trihydroxy-docosa-4Z,9E,11E,13Z,15E,19Z-hexaenoic acid),

aspirin-triggered resolvin D2 (AT-RvD2; 7S,16R,17R-trihydroxy-docosa 4Z,8E,10Z,12E,14E,19Z-hexaenoic acid),

aspirin-triggered resolvin D3 (AT-RvD3; 4S,11,17R-trihydroxy-docosa-5Z,7E,9E,13Z,15E,19Z-hexaenoic acid),

aspirin-triggered resolvin D4 (AT-RvD4; 4S,5,17R-trihydroxy-docosa-6E,8E,10Z,13Z,15E,19Z-hexaenoic acid),

aspirin-triggered resolvin D5 (AT-RvD5; 7S,17R-dihydroxy-docosa-5Z,8E,10Z,13Z,15E,19Z-hexaenoic acid),

aspirin-triggered resolvin D6 (AT-RvD6; 4S,17R-dihydroxy-docosa-5E,7Z,10Z,14Z,16E,19Z-hexaenoic acid),

7S,17S-diHDPA n-3 (7S,17S-dihydroxy-docosa-8E,10Z,13Z,15Z,19Z-pentaenoic acid (o)-3)),

lipoxin A 4 (LXA 4 ; 5S,6R,15S-trihydroxy-eicosa-7E,9E,11Z,13E-tetraenoic acid),

15-epi-lipoxin A 4 (15-epi-LXA 4 ; 5S,6R,15R-trihydroxy-eicosa-7E,9E,11Z,13E-tetraenoic acid),

delta12-prostaglandin J 2 (delta12-PGJ 2 ; 11-oxo-15S-hydroxy-prosta-5Z,9,12E-trienoic acid),

15-deoxy-delta12,14-prostaglandin J 2 (15-deoxy-delta12,14-PGJ 2 ; 11-oxo-prosta-5Z,9,12E,14E-tetraenoic acid),

11(12)-epoxy-eicosatetraenoic acid (11(12)-EpETE; 11(12)-epoxy-eicosa-5Z,8Z,14Z,17Z-tetraenoic acid),

17(18)-epoxy-eicosatetraenoic acid (17(18)-EpETE; 17(18-epoxy-eicosa-5Z,8Z,11Z,14Z-tetraenoic acid),

19(20)-epoxy-docosapentaenoic acid (19(20)-EpDPE; 19(20)-epoxy-docosa 4Z,7Z,10Z,13Z,16Z-pentaenoic acid),

10S,17S-HDPA n-6 (10S,17S-dihydroxy-docosa-4Z,7Z,11E,13Z,15E-pentaenoic acid),

7,17-HDPA n-6 (7,17-dihydroxy-docosa-4Z,8E,10Z,13Z,15E-pentaenoic acid),

7,14-HDPA n-6 (7,14-dihydroxy-docosa-4Z,8E,10Z,12Z,16Z-pentaenoic acid),

10S,17S-HDPA n-6 (10S,17S-dihydroxy-docosa-7Z,11E,13Z,15E,19Z-pentaenoic acid), and/or

7,17-HDPA n-6 (7,17-dihydroxy-docosa-8E,10Z,13Z,15E,19Z-pentaenoic acid).

5 . The method of claim 1 wherein at least one of the fatty acids of the remodeled triglyceride is comprised of a SPM precursor and/or an esterified SPM precursor further selected from the group consisting of:

5S-HEPE (5S-hydroxy-eicosa-6E,8Z,11Z,14Z,17Z-pentaenoic acid),

11S-HEPE (11S-hydroxy-eicosa-5Z,8Z,12E,14Z,17Z-pentaenoic acid),

12S-HEPE (12S-hydroxy-eicosa-5Z,8Z,10E,14Z,7Z-pentaenoic acid),

12R-HEPE (12R-hydroxy-eicosa-5Z,8Z,10E,14Z,17Z-pentaenoic acid),

15S-HEPE (15S-hydroxy-eicosa-5Z,8Z,11Z,13E,17Z-pentaenoic acid),

4S-HDHA (4S-hydroxy-docosa-5E,7Z,10Z,13Z,16Z,19Z-hexaenoic acid),

7S-HDHA (7S-hydroxy-docosa-4Z,8E,10Z,13Z,6Z,19Z-hexaenoic acid),

10S-HDHA (10S-hydroxy-docosa-4Z,7Z,11E,13Z,16Z,19Z-hexaenoic acid),

11S-HDHA (11S-hydroxy-docosa-4Z,7Z,9E,13Z,16Z,19Z-hexaenoic acid),

14S-HDHA (14S-hydroxy-docosa-4Z,7Z,10Z,12E,16Z,19Z-hexaenoic acid),

14R-HDHA (14R-hydroxy-docosa-4Z,7Z,10Z,12E,16Z,19Z-hexaenoic acid),

20S-HDHA (20S-hydroxy-docosa-4Z,7Z,10Z,13Z,16Z,19Z-hexaenoic acid),

17S-HDPAn-6 (17S-hydroxy-docosa-4Z,7Z,10Z,13Z,15E-pentaenoic acid),

14S-HDPAn-6 (14S-hydroxy-docosa-4Z,7Z,10Z,12E,16Z-pentaenoic acid),

10S-HDPAn-6 (10S-hydroxy-docosa-4Z,7Z,11E,13Z,16Z-pentaenoic acid),

17S-HDPAn-3 (17S-hydroxy-docosa-7Z,10Z,13Z,15E,19Z-pentaenoic acid),

14S-HDPAn-3 (14S-hydroxy-docosa-7Z,10Z,12E,16Z,19Z-pentaenoic acid),

10S-HDPAn-6 (10S-hydroxy-docosa-7Z,11E,13Z,16Z,19Z-pentaenoic acid),

15S-HETE (15S-hydroxy-eicosa-5Z,8Z,11Z,13E-tetraenoic acid),

17S-HDHA (17S-hydroxy-docosa-4Z,7Z,10Z,13Z,15E,19Z-hexaenoic acid),

17R-HDHA (17R-hydroxy-docosa-4Z,7Z,10Z,13Z,15E,19Z-hexaenoic acid),

18S-HEPE (18S-hydroxy-eicosa-5Z,8Z,11Z,14Z,16E-pentaenoic acid), and/or

18R-HEPE (18R-hydroxy-eicosa-5Z,8Z,11Z,14Z,16E-pentaenoic acid).

6 . The method of claim 1 wherein the remodeled triglyceride is formed from an enzymatic or a chemical transesterification of the esterified SPMs and/or SPM precursors.

7 . The method of claim 1 wherein the remodeled triglyceride has anti-inflammatory or resolution stimulating activity.

8 . An oil comprising remodeled triglycerides prepared according to claim 1

9 . A remodeled triglyceride having a glycerol backbone and three fatty acids chemical bound thereto, wherein at least one of the fatty acids of the remodeled triglyceride comprises 18-HEPE, 17-HDHA, or 14-HDHA.

10 . The remodeled triglyceride of claim 9 wherein the fatty acids are further comprised of a long chain omega-3 polyunsaturated fatty acids.

11 . The remodeled triglyceride of claim 10 wherein the long chain omega-3 polyunsaturated fatty acids comprise EPA and/or DHA.

12 . The remodeled triglyceride of claim 9 wherein at least one of the fatty acids of the remodeled triglyceride is further selected from the group consisting of: