Oxylipins from stearidonic acid and gamma-linolenic acid and methods of making and using same

Abstract

Disclosed are novel oxylipins that are derived from γ-linolenic acid (GLA; 18:3n-6) and stearidonic acid (STA or SDA; 18:4n-3), and methods of making and using such oxylipins. Also disclosed is the use of such oxylipins in therapeutic and nutritional or cosmetic applications, and particularly as anti-inflammatory or anti-neurodegenerative compounds. Also disclosed are The invention novel ways of producing long chain polyunsaturated acid (LCPUFA)-rich oils and compositions that contain enhanced and effective amounts of SDA- and/or GLA-derived oxylipins.

1 . An isolated dihydroxy oxylipin of stearidonic acid (SDA). 
     
     
         2 . (canceled) 
     
     
         3 . (canceled) 
     
     
         4 . A composition comprising at least one oxylipin of  claim 1 . 
     
     
         5 . (canceled) 
     
     
         6 . An isolated dihydroxy or trihydroxy oxylipin of γ-linolenic acid (GLA). 
     
     
         7 . The isolated oxylipin of  claim 6 , wherein the oxylipin is an R- or S-epimer or an R/S epimer of 6,13-dihydroxy GLA, or an analog, derivative or salt thereof. 
     
     
         8 . An isolated monohydroxy oxylipin of y-linolenic acid (GLA), wherein the oxylipin is an R- or S-epimer of an oxylipin selected from the group consisting of: 7-hydroxy GLA, and 12-hydroxy GLA, or an analog, derivative or salt thereof. 
     
     
         9 . A composition comprising at least one oxylipin of any one of  claims 6  to  8 . 
     
     
         10 - 32 . (canceled) 
     
     
         33 . 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: an oxylipin derivative of SDA and an oxylipin derivative of GLA, to reduce at least one symptom of inflammation or neurodegeneration in the individual. 
     
     
         34 . The method of  claim 33 , wherein the agent is effective to reduce the production of tumor necrosis factor-α (TNF-α) by T lymphocytes. 
     
     
         35 . The method of  claim 33 , wherein the agent is effective to reduce the migration of neutrophils and macrophages into a site of inflammation. 
     
     
         36 . The method of  claim 33 , wherein the agent is effective to reduce interleukin-1β (IL-1β) production in the individual. 
     
     
         37 . The method of  claim 33 , wherein the agent is effective to reduce macrophage chemotactic protein-1 (MCP-1) in the individual. 
     
     
         38 . The method of  claim 33 , further comprising administering at least one long chain fatty acid and/or at least one oxylipin derivative thereof to the individual. 
     
     
         39 . The method of  claim 38 , wherein the long chain fatty acid is selected from the group consisting of GLA, SDA. 
     
     
         40 . The method of  claim 38 , wherein the long chain fatty acid is provided in one of the following forms: as triglyceride containing the long chain fatty acid, as a phospholipid containing the long chain fatty acid, as a free fatty acid, or as an ethyl or methyl ester of the long chain fatty acid. 
     
     
         41 - 43 . (canceled) 
     
     
         44 . The method of  claim 33 , wherein the oxylipin derivative is selected from the group consisting of: R-epimers of the monohydroxy products of SDA, S-epimers of the monohydroxy product of SDA, R-epimers of the monohydroxy products of GLA, S-epimers of the monohydroxy product of GLA, R-epimers of the dihydroxy products of SDA, S-epimers of dihydroxy products of SDA, R-epimers of the dihydroxy products of GLA, S-epimers of dihydroxy products of GLA, R-epimers of the trihydroxy products of SDA, S-epimers of the trihydroxy products of SDA, R-epimers of the trihydroxy products of GLA, and S-epimers of the trihydroxy products of GLA. 
     
     
         45 . The method of  claim 33 , wherein the oxylipin derivative is an R- or S-epimer of an oxylipin selected from the group consisting of: 6-hydroxy SDA; 7-hydroxy SDA; 9-hydroxy SDA; 10-hydroxy SDA; 12-hydroxy SDA;; 15-hydroxy SDA; 16-hydroxy SDA; 6,13-dihydroxy SDA; 6,16-dihydroxy SDA; 6-hydroxy GLA; 7-hydroxy GLA; 9-hydroxy GLA; 12-hydroxy GLA; 13-hydroxy GLA; and 6,13-dihydroxy GLA; or an analog, derivative or salt thereof. 
     
     
         46 - 100 . (canceled)