Oxylipins From Long Chain Polyunsaturated Fatty Acids and Methods of Making and Using the Same

Abstract

Disclosed are novel oxylipins, referred to herein as docosanoids, that are derived from C22 polyunsaturated fatty acids, and method of making and using such oxylipins. Also disclosed is the use of docosapentaenoic acid (C22:5n-6) (DPAn-6), docosapentaenoic acid (C22:5n-3) (DPAn-3), and docosatetraenoic acid (DTAn-6: C22:4n-6) as substrates for the production of novel oxylipins, and to the oxylipins produced thereby. Also disclosed is the use of DPAn-6, DPAn-3, DTAn-6, and/or the oxylipins derived therefrom, and/or novel docosanoids derived from the structures of C22 fatty acids, in therapeutic and nutritional or cosmetic applications, and particularly as anti-inflammatory or anti-neurodegenerative compounds. The invention also relates to novel ways of producing long chain polyunsaturated acid (LCPUFA)-rich oils and compositions that contain enhanced and effective amounts of LCPUFA-derived oxylipins, and particularly, docosanoids.

1 . (canceled) 
     
     
         2 . An isolated docosanoid that is an R- or S-epimer of a docosanoid selected from the group consisting of: monohydroxy derivatives of DPAn-6, dihydroxy derivatives of DPAn-6, and tri-hydroxy derivatives of DPAn-6. 
     
     
         3 . The isolated docosanoid of  claim 1 , wherein the docosanoid is an R- or S-epimer of a docosanoid selected from the group consisting of: 7-hydroxy DPAn-6; 8-hydroxy DPAn-6; 10-hydroxy DPAn-6; 11-hydroxy DPAn-6; 13-hydroxy DPAn-6; 14-hydroxy DPAn-6; 17-hydroxy DPAn-6; 7,17-dihydroxy DPAn-6; 10,17-dihydroxy DPAn-6; 13,17-dihydroxy DPAn-6; 7,14-dihydroxy DPAn-6; 8,14-dihydroxy DPAn-6; 16,17-dihdroxy DPAn-6; 4,5-dihydroxy DPAn-6; 7,16,17-trihydroxy DPAn-6; and 4,5,17-trihydroxy DPAn-6. 
     
     
         4 . (canceled) 
     
     
         5 . A composition comprising at least one docosanoid of  claim 2 , wherein the composition is a therapeutic composition, a nutritional composition, or a cosmetic composition. 
     
     
         6 - 42 . (canceled) 
     
     
         43 . A method to prevent or reduce at least one symptom of inflammation or neurodegeneration in an individual, comprising administering to an individual at risk of, diagnosed with, or suspected of having inflammation or neurodegeneration or a condition or disease related thereto, an agent selected from the group consisting of: DPAn-6, and an oxylipin derivative of DPAn-6, to reduce at least one symptom of inflammation or neurodegeneration in the individual. 
     
     
         44 - 54 . (canceled) 
     
     
         55 . The method of  claim 43 , wherein the oxylipin derivative is an R- or S-epimer of a docosanoid selected from the group consisting of: 7-hydroxy DPAn-6; 8-hydroxy DPAn-6; 10-hydroxy DPAn-6; 11-hydroxy DPAn-6; 13-hydroxy DPAn-6; 14-hydroxy DPAn-6; 17-hydroxy DPAn-6; 7,17-dihydroxy DPAn-6; 10,17-dihydroxy DPAn-6; 13,17-dihydroxy DPAn-6; 7,14-dihydroxy DPAn-6; 8,14-dihydroxy DPAn-6; 16,17-dihdroxy DPAn-6; 4,5-dihydroxy DPAn-6; 7,16,17-trihydroxy DPAn-6; and 4,5,17-trihydroxy DPAn-6. 
     
     
         56 . (canceled) 
     
     
         57 . The method of  claim 43 , wherein the agent is selected from the group consisting of 17-hydroxy DPAn-6 and 10,17-dihydroxy DPAn-6. 
     
     
         58 . The method of  claim 43 , wherein the agent is 17-hydroxy DPAn-6. 
     
     
         59 . The method of  claim 43 , wherein the agent is 10,17-dihydroxy DPAn-6. 
     
     
         60 . The method of  claim 43 , wherein the agent is DPAn-6. 
     
     
         61 . (canceled) 
     
     
         62 . The method of  claim 43 , further comprising administering aspirin to the individual. 
     
     
         63 . The method of  claim 43 , further comprising administering at least one agent selected from the group consisting of a statin, a non-steroidal anti-inflammatory agent, an antioxidant, and a neuroprotective agent, to the individual. 
     
     
         64 - 122 . (canceled)