(±)14-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 14(S)-HDoHE by human platelets along with 11(S)-HDoHE.^6,7,5 14(S)-HDoHE is also produced by salmon gills upon stimulation with calcium ionophore.⁸ 14(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 70, 3.6, and 5.3 µM, respectively.^7,9 (±)14-HDoHE is a potential marker of oxidative stress in brain and retina where DHA is an abundant polyunsaturated fatty acid.

1 VanRollins, M., and 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., and Pace-Asciak, C.R. Facile preparation and structural determination of monohydroxy derivatives of docosahexaenoic acid (HDoHE) by α-tocopherol-directed autoxidation. Anal Biochem 214 165-170 (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., 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 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., 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 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 a-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. 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).

VanRollins, M., and Murphy, R.C. Autooxidation of docosahexaenoic acid: Analysis of ten isomers of hydroxydocosahexaenoate. J Lipid Res 25 507-517 (1984).

VanRollins, M., Baker, R.C., Sprecher, H., et al. Oxidation of docosahexaenoic acid by rat liver microsomes. J Biol Chem 259 5776-5783 (1984).

Karanian, J.W., Kim, H.Y., and 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).

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).

Sprecher, H., and Careaga, M.M. Metabolism of (n-6) and (n-3) polyunsaturated fatty acids by human platelets. Prostaglandins Leukot Med 23 129-134 (1986).

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 B 652 123-136 (1994).

Bell, J.G., Dick, J.R., and Sargent, J.R. Effect of diets rich in linoleic or a-linoleic acid on phospholipid fatty acid composition and eicosanoid production in Atlantic Salmon (Salmo salar). Lipids 28 819-826 (1993).

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).

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 214 165-170 (1993).

Hatmi, M., Lussiana, J.P., Junien, J.L., et al. Interference of eicosapentaenoic and docosahexaenoic acids with arachidonate-and U46619-induced platelet activation and desensitization. Biochem Pharmacol 37 481-489 (1988).

Fischer, S., Schacky, C.V., Siess, W., et al. Uptake, release and metabolism of docosahexaenoic acid (DHA, C₂₂:6ω3) in human platelets and neutrophils. Biochem Biophys Res Commun 120 907-918 (1984).

Aveldaño, 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 9339-9343 (1983).

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