(+/-) 14-HDOHE

Description

(±)14-HDHA is an autoxidation product of docosahexaenoic acid (DHA) in vitro.^1,2 It is also produced from incubations of DHA in rat liver, brain, and intestinal microsomes.^3,4,5 DHA is metabolized to 14(S)-HDHA by human platelets along with 11(S)-HDHA.^6,7,5 14(S)-HDoHE is also produced by salmon gills upon stimulation with calcium ionophore.⁸ 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.^7,9 (±)14-HDHA is a potential marker of oxidative stress in brain and retina where DHA is an abundant polyunsaturated fatty acid.

Definition

ChEBI: 14-HDoHE is a hydroxydocosahexaenoic acid that consists of (4Z,7Z,10Z,12E,16Z,19Z)-docosahexaenoic acid bearing an additional 14-hydroxy substituent. It has a role as a human xenobiotic metabolite. It is a hydroxydocosahexaenoic acid and a secondary allylic alcohol. It is a conjugate acid of a 14-HDoHE(1-).

References

1. VanRollins, M., and Murphy, R.C. Autooxidation of docosahexaenoic acid: Analysis of ten isomers of hydroxydocosahexaenoate J. Lipid Res. 25(5),507-517(1984).
2. Reynaud, D., Thickitt, C.P., and Pace-Asciak, C.R. Facile preparation and structural determination of monohydroxy derivatives of docosahexaenoic acid (HDoHE) by α-tocopherol-directed autoxidation Anal. Biochem. 214(1),165-170(1993).
3. VanRollins, M., Baker, R.C., Sprecher, H., et al. Oxidation of docosahexaenoic acid by rat liver microsomes J. Biol. Chem. 259(9),5776-5783(1984).
4. Yamane, M., Abe, A., and Yamane, S. High-performance liquid chromatography-thermospray mass spectrometry of epoxy polyunsaturated fatty acids and epoxyhydroxy polyunsaturated fatty acids from an incubation mixture of rat tissue homogenate J. Chromatogr. 652(2),123-136(1994).
5. Kim, H.Y., Karanian, J.W., Shingu, T., et al. Sterochemical analysis of hydroxylated docosahexaenoates produced by human platelets and rat brain homogenate Prostaglandins 40(5),473-490(1990).
6. Avelda?o, M.I., and Sprecher, H. Synthesis of hydroxy fatty acids from 4,7,10,13,16,19-[1-¹⁴C] docosahexaenoic acid by human platelets J. Biol. Chem. 258(15),9339-9343(1983).
7. Lagarde, M., Croset, M., Guichardant, M., et al. Role of lipoxygenase products in platelet function: Relation to fatty acid modified phospholipids Adv. Exp. Med. Biol. 192,327-335(1985).
8. Bell, J.G., Dick, J.R., and Sargent, J.R. Effect of diets rich in linoleic or α-linoleic acid on phospholipid fatty acid composition and eicosanoid production in Atlantic Salmon (Salmo salar) Lipids 28,819-826(1993).
9. Karanian, J.W., Kim, H.Y., and Salem, N., Jr. Inhibitory effects of n-6 and n-3 hydroxy fatty acids on thromboxane (U46619)-induced smooth muscle contraction J. Pharmacol. Exp. Ther. 270(3),1105-1109(1994).