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(±)11-HDoHE 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 11(S)-HDoHE by human platelets and canine retina.6,7,8,5 In addition to 11(S)-HDoHE, 14(S)-HDoHE is also produced by platelets.6,8,5 11(S)-HDoHE 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 50, 4.7, and 7.5 µM, respectively.8,9 (±)11-HDoHE is a potential marker of oxidative stress in brain and retina where DHA is an abundant polyunsaturated fatty acid.
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1
VanRollins, M., Murphy, R.C. Autooxidation of docosahexaenoic acid: Analysis of ten isomers of hydroxydocosahexaenoate. J Lipid Res 25 507-517 (1984).
2
Reynaud, D., Thickitt, C.P., Pace-Asciak, C.R. Facile preparation and structural determination of monohydroxy derivatives of docosahexaenoic acid (HDoHE) by α-tocopherol-directed autoxidation. Anal Biochem 214 165-170 (1993).
3
VanRollins, M., Baker, R.C., Sprecher, H., et al. Oxidation of docosahexaenoic acid by rat liver microsomes. J Biol Chem 259 5776-5783 (1984).
4
Yamane, M., Abe, A., 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. Journal of Chromatography B 652 123-136 (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 40 473-490 (1990).
6
Aveldaño, M.I., 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 9339-9343 (1983).
7
Bazan, N.G., Birkle, D.L., Reddy, T.S. Docosahexaenoic acid (22:6, n-3) is metabolized to lipoxygenase reaction products in the retina. Biochem Biophys Res Commun 125 741-747 (1984).
8
Lagarde, M., Croset, M., Guichardant, M., et al. Role of lipoxygenase products in platelet function: Relation to fatty acid modified phospholipids. Adv Exp Med Bio 192 327-335 (1985).
9
Karanian, J.W., Kim, H.Y., Salem, N. Inhibitory effects of n-6 and n-3 hydroxy fatty acids on thromboxane (U46619)-induced smooth muscle contraction. J Pharmacol Exp Ther 270 1105-1109 (1994).
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