(±)14hdha

(±)14-HDHA is an autoxidation product of docosahexaenoic acid (DHA) in vitro. It is also produced from incubations of DHA in rat liver, brain, and intestinal microsomes. DHA is metabolized to 14(S)-HDHA by human platelets along with 11(S)-HDHA. 14(S)-HDoHE is also produced by salmon gills upon stimulation with calcium ionophore. 14(S)-HDHA was shown to be an inhibitor of U-46619-induced human platelet aggregation and rabbit and rat aortic smooth muscle contraction with IC50 values of about 70, 3.6, and 5.3 μM, respectively. (±)14-HDHA is a potential marker of oxidative stress in brain and retina where DHA is an abundant polyunsaturated fatty acid.

Docosahexaenoic acid is a nutritionally-derived ω-3 fatty acid that is abundant in the brain and the retina and is thought to be important in early development and for therapeutic approaches to inflammatory disorders and cancer. 14(S)-HDHA is an oxygenation product of DHA that serves as a precursor to maresin 1 , an anti-inflammatory, pro-resolving mediator that prevents polymorphonuclear neutrophil (PMN) infiltration and stimulates macrophage phagocytosis. At doses as low as 0.2 ng/mouse 14(S)-HDHA administration resulted in reduced infiltration of PMNs into sites of inflammation.