Identification of 15-hydroxy-11,12-epoxyeicosatrienoic acid as a vasoactive 15-lipoxygenase metabolite in rabbit aorta

American Journal of Physiology. Heart and Circulatory Physiology
Yuttana ChawengsubW B Campbell

Abstract

Arachidonic acid (AA) causes endothelium-dependent smooth muscle hyperpolarizations and relaxations that are mediated by a 15-lipoxygenase-I (15-LO-I) metabolite, 11,12,15-trihydroxyeicosatrienoic acid (11,12,15-THETA). We propose that AA is metabolized sequentially by 15-LO-I and hydroperoxide isomerase to an unidentified hydroxyepoxyeicosatrienoic acid (HEETA), which is hydrolyzed by a soluble epoxide hydrolase (sEH) to 11,12,15-THETA. After incubation of aorta with 14C-labeled AA, metabolites were extracted and the HEETAs were resolved by performing HPLC. Mass spectrometric analyses identified 15-Hydroxy-11,12-epoxyeicosatrienoic acid (15-H-11,12-EETA). Incubation of aortic incubates with methanol and acetic acid trapped the acid-sensitive 15-H-11,12-EETA as methoxydihydroxyeicosatrienoic acids (MDHEs) (367 m/z, M-H). Pretreatment of the aortic tissue with the sEH inhibitor 12-(3-adamantan-1-yl-ureido)-dodecanoic acid (AUDA; 10(-6) M) increased the formation of 15-H-11,12-EETA, measured as MDHEs. Thus 15-H-11,12-EETA is an acid- and sEH-sensitive precursor of 11,12,15-THETA. Aortic homogenates and endothelial cells contain a 57-kDa protein corresponding to the rabbit sEH. In preconstricted aortic rings, AA (10(-7)-10(-4) M) ...Continue Reading

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Citations

Apr 25, 2012·Journal of Cardiovascular Pharmacology·Ahmet B InceogluSaul Schaefer
Jun 16, 2009·American Journal of Physiology. Heart and Circulatory Physiology·Yuttana ChawengsubWilliam B Campbell
Dec 4, 2012·American Journal of Physiology. Heart and Circulatory Physiology·Lawan SiangjongWilliam B Campbell
Jan 5, 2011·American Journal of Physiology. Heart and Circulatory Physiology·Kathryn M GauthierWilliam B Campbell
Jun 3, 2016·Pulmonary Circulation·Nadine Al-NaamaniIoana R Preston
May 11, 2013·Pulmonary Circulation·Kristen D SaglianiIoana R Preston
Oct 4, 2008·Arteriosclerosis, Thrombosis, and Vascular Biology·Nitin T AggarwalWilliam B Campbell
Dec 30, 2008·American Journal of Physiology. Heart and Circulatory Physiology·Nitin T AggarwalWilliam B Campbell
Dec 20, 2012·Journal of Cardiovascular Pharmacology·William B Campbell, Kathryn M Gauthier
Nov 10, 2015·Acta Physiologica·S W S Leung, P M Vanhoutte
Nov 16, 2010·The Journal of Thoracic and Cardiovascular Surgery·Sandra PfisterElizabeth R Jacobs

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