Description
(±)11-
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 11(S)-
HDHA by human platelets and canine retina.
6,7,8,5 In addition to 11(S)-
HDHA, 14(S)-
HDHA is also produced by platelets.
6,8,5 11(S)-
HDHA was shown to be an inhibitor of U-
46619-
induced human platelet aggregation and rabbit and rat aortic smooth muscle contraction with IC
50 values of about 50, 4.7, and 7.5 μM, respectively.
8,9 (±)11-
HDHA is a potential marker of oxidative stress in brain and retina where DHA is an abundant polyunsaturated fatty acid.
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. Bazan, N.G., Birkle, D.L., and Reddy, T.S. Docosahexaenoic acid (22:6, n-3) is metabolized to lipoxygenase reaction products in the retina Biochem. Biophys. Res. Commun. 125(2),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. Biol. 192,327-335(1985).
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).
