(±)5hepe

(±)5-HEPE is produced by non-enzymatic oxidation of EPA. It contains equal amounts of 5(S)-HEPE and 5(R)-HEPE. The biological activity of (±)5-HEPE is likely mediated by one of the individual isomers, most commonly the 5(S) isomer in mammalian systems. EPA can be metabolized to 5-HEPE in human and bovine neutrophils, and human eosinophils, which is further metabolized to 5-oxoEPE and LTB5. The 5-series metabolites of EPA, namely 5-HEPE, 5-oxoEPE, and LTB5, have significantly decreased biological effects compared to the arachidonic acid-derived metabolites.

5(S)-HEPE, an active metabolite of eicosapentaenoic acid (EPA), is produced via the action of 5-lipoxygenase (5-LO). This compound functions as an agonist for G protein-coupled receptor 119 (GPR119), promoting cAMP accumulation in CHO-K1 cells expressing human GPR119 at 10 µM concentration. Additionally, 5(S)-HEPE enhances glucose-stimulated insulin secretion from MING6 insulinoma pancreatic islets and glucagon-like peptide 1 (GLP-1) secretion from HuTu 80 adenocarcinoma cells at the same concentration. Notably, serum levels of 5(S)-HEPE are increased in hyperlipidemia patients.