(±)8hdha

(±)8-HDHA is an autoxidation product of docosahexaenoic acid (DHA) in vitro and is produced from incubations of DHA in rat liver, brain, and intestinal microsomes. It is a potential marker of oxidative stress in the brain and retina, where DHA is an abundant polyunsaturated fatty acid.

(±)17-HDHA is an autoxidation product of docosahexaenoic acid in vitro. It is also produced from incubations of DHA in rat liver, brain, and intestinal microsomes. 17(S)-HDHA could be produced by enzymatic oxidation of DHA using soybean lipoxygenase (LO) and is the putative product of mammalian 15-LOs. 17(S)-HDHA was shown to be an inhibitor of U-46619 -induced rabbit and rat aortic smooth muscle contraction with IC50 values of 4.9 and 7.2 μM, respectively. (±)17-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.

Resolvins are a group of polyhydroxylated metabolites of docosahexaenoic acid (DHA) found in the inflammatory exudates of aspirin-treated experimental animals. 17(R)-HDHA is the primary oxygenation product of DHA when exposed to aspirin-inhibited cyclooxygenase-2. 17(R)-HDHA serves as a precursor to resolvins and has intrinsic biological activity, such as the inhibition of TNFα-induced IL-1β expression in human glioma cells.

(±)7-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. Enzymatic transformation of DHA by RBL-1 cells and human neutrophils also produces 7-HDHA. However, the enzymatic product is most likely the S-isomer. (±)7-HDHA is a potential marker of oxidative stress in brain and retina where DHA is an abundant polyunsaturated fatty acid.

17(S)-HDHA is a primary mono-oxygenation product of docosahexaenoic acid in human whole blood, human leukocytes, and mouse brain. 17(S)-HDHA serves as a precursor to 17(S)-resolvins and has intrinsic biological activity, such as the inhibition of TNF-α-induced interleukin-1β expression in human glioma cells and inhibition of TNF-α-induced leukocyte trafficking to the mouse air pouch.

(±)4-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. Enzymatic transformation of DHA by RBL-1 cells also produces 4-HDHA. However, the enzymatic product is most likely the S-isomer. (±)4-HDHA is a potential marker of oxidative stress in brain and retina where DHA is an abundant polyunsaturated fatty acid.