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. Author manuscript; available in PMC: 2019 Aug 7.
Published in final edited form as: Prostaglandins Other Lipid Mediat. 2019 May 11;143:106337. doi: 10.1016/j.prostaglandins.2019.106337

Figure 2. Oxidation of Omega-3 endocannabinoids (DHA-EA and EPA-EA) by the LOX and CYP450 pathway.

Figure 2.

(A) For the LOX pathway, oxidation can occur once and metabolites formed can undergo additionally oxidation or reduction to form seven DHA-EA-LOX metabolites; 17-hydroperoxydocosahexaenoyl ethanolamide (17-HpDHA-EA), 17-hydroxy-4Z,7Z,10Z,13Z,15E,19Z-docosahexaenoylethanolamide (17-HDHA-EA), 10,17-dihydroxydocosahexaenoyl ethanolamide (10,17-diHDHA-EA), 7,17-dihydroxydocosahexaenoyl ethanolamide (7,17-diHDHA-EA), 4,17-dihydroxydocosahexaenoyl ethanolamide (4,17-diHDHA-EA), 13-hydroxy-16(17)-epoxy-docosapentaenyolethanolamide (13-HEDPEA) and 15-hydroxy-16(17)-epoxy-docosapentaenyolethanolamide (15-HEDPEA). (B) The CYP450 pathway oxidizes DHA-EA and EPA-EA into six epoxydocosapentaenoic acid-ethanolamide (EDP-EA) and five epoxyeicosatetraenoic acid-ethanolamide (EEQ-EA) regioisomers, respectively.