11(R),12(S),15(S)-trihydroxyeicosa-5(Z),8(Z),13(E)-trienoic acid: an endothelium-derived 15-lipoxygenase metabolite that relaxes rabbit aorta

American Journal of Physiology. Heart and Circulatory Physiology
Kathryn M GauthierWilliam B Campbell

Abstract

Previous studies indicate that 11,12,15-trihydroxyeicosatrienoic acid (11,12,15-THETA), an endothelium-derived hyperpolarizing factor in the rabbit aorta, mediates a portion of the relaxation response to acetylcholine by sequential metabolism of arachidonic acid by 15-lipoxygenase, hydroperoxide isomerase, and epoxide hydrolase. To determine the stereochemical configuration of the endothelial 11,12,15-THETA, its activity and chromatographic migration were compared with activity and migration of eight chemically synthesized stereoisomers of 11,12,15(S)-THETA. Of the eight isomers, only 11(R),12(S),15(S)-trihydroxyeicosa-5(Z),8(Z),13(E)-trienoic acid comigrated with the biological 11,12,15-THETA on reverse- and normal-phase HPLC and gas chromatography. The same THETA isomer (10(-7)-10(-4) M) relaxed the rabbit aorta in a concentration-related manner (maximum relaxation = 69 +/- 5%). These relaxations were blocked by apamin (10(-7) M), an inhibitor of small-conductance Ca2+-activated K+ channels. In comparison, 11(S),12(R),15(S),5(Z),8(Z),13(E)-THETA (10(-4) M) relaxed the aorta by 22%. The other six stereoisomers were inactive in this assay. With use of the whole cell patch-clamp technique, it was shown that 10(-4) M 11(R),12(S),...Continue Reading

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Citations

Jul 23, 2013·Prostaglandins & Other Lipid Mediators·Tamas KriskaWilliam B Campbell
Jun 16, 2009·American Journal of Physiology. Heart and Circulatory Physiology·Yuttana ChawengsubWilliam B Campbell
Oct 2, 2012·American Journal of Physiology. Heart and Circulatory Physiology·Arjun MenonJohn F LaDisa
Jan 5, 2011·American Journal of Physiology. Heart and Circulatory Physiology·Kathryn M GauthierWilliam B Campbell
Apr 3, 2012·American Journal of Physiology. Heart and Circulatory Physiology·Tamas KriskaWilliam B Campbell
Sep 23, 2014·Biochimica Et Biophysica Acta·Cecil R Pace-Asciak
Sep 8, 2011·Annals of Medicine·Michel FélétouPaul M Vanhoutte
Sep 9, 2016·Physiological Reviews·Anita AyerRoland Stocker
Dec 20, 2012·Journal of Cardiovascular Pharmacology·William B Campbell, Kathryn M Gauthier
Feb 4, 2009·British Journal of Pharmacology·Michel Félétou
Jan 15, 2008·American Journal of Physiology. Heart and Circulatory Physiology·Yuttana ChawengsubWilliam B Campbell

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