NDLI: Lipoxygenase-catalyzed transformation of epoxy fatty acids to hydroxy-endoperoxides: a potential P450 and lipoxygenase interaction.

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	Teder, Tarvi Boeglin, William E. Brash, Alan R.
Description	Country affiliation: Estonia Author Affiliation: Teder T ( Department of Pharmacology and the Vanderbilt Institute of Chemical Biology, Vanderbilt University, Nashville, TN 37232 Department of Chemistry, Tallinn University of Technology, 12618 Tallinn, Estonia.); Boeglin WE ( Department of Pharmacology and the Vanderbilt Institute of Chemical Biology, Vanderbilt University, Nashville, TN 37232.); Brash AR ( Department of Pharmacology and the Vanderbilt Institute of Chemical Biology, Vanderbilt University, Nashville, TN 37232.)
Abstract	Herein, we characterize a generally applicable transformation of fatty acid epoxides by lipoxygenase (LOX) enzymes that results in the formation of a five-membered endoperoxide ring in the end product. We demonstrated this transformation using soybean LOX-1 in the metabolism of 15,16-epoxy- -linolenic acid, and murine platelet-type 12-LOX and human 15-LOX-1 in the metabolism of 14,15-epoxyeicosatrienoic acid (14,15-EET). A detailed examination of the transformation of the two enantiomers of 15,16-epoxy- -linolenic acid by soybean LOX-1 revealed that the expected primary product, a 13S-hydroperoxy-15,16-epoxide, underwent a nonenzymatic transformation in buffer into a new derivative that was purified by HPLC and identified by UV, LC-MS, and ¹H-NMR as a 13,15-endoperoxy-16-hydroxy-octadeca-9,11-dienoic acid. The configuration of the endoperoxide (cis or trans side chains) depended on the steric relationship of the new hydroperoxy moiety to the enantiomeric configuration of the fatty acid epoxide. The reaction mechanism involves intramolecular nucleophilic substitution (SNi) between the hydroperoxy (nucleophile) and epoxy group (electrophile). Equivalent transformations were documented in metabolism of the enantiomers of 14,15-EET by the two mammalian LOX enzymes, 15-LOX-1 and platelet-type 12-LOX. We conclude that this type of transformation could occur naturally with the co-occurrence of LOX and cytochrome P450 or peroxygenase enzymes, and it could also contribute to the complexity of products formed in the autoxidation reactions of polyunsaturated fatty acids.
File Format	HTM / HTML
ISSN	00222275
e-ISSN	15397262
DOI	10.1194/jlr.M054072
Journal	The Journal of Lipid Research
Issue Number	12
Volume Number	55
Language	English
Publisher	American Society for Biochemistry and Molecular Biology
Publisher Date	2014-12-01
Publisher Place	United States
Access Restriction	Open
Subject Keyword	Discipline Biochemistry Arachidonate 12-lipoxygenase Metabolism Arachidonate 15-lipoxygenase Eicosanoids Linolenic Acids Lipid Peroxides Lipoxygenase Soybean Proteins 8,11,14-eicosatrienoic Acid Analogs & Derivatives Chemistry Animals Genetics Biocatalysis Blood Platelets Enzymology Chromatography, High Pressure Liquid Epoxy Compounds Gas Chromatography-mass Spectrometry Hydroxylation Mice Molecular Structure Nuclear Magnetic Resonance, Biomolecular Oxidation-reduction Recombinant Proteins Spectrometry, Mass, Electrospray Ionization Stereoisomerism Comparative Study Research Support, N.i.h., Extramural Research Support, Non-u.s. Gov't
Content Type	Text
Resource Type	Article
Subject	Cell Biology Biochemistry Endocrinology

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Lipoxygenase-catalyzed transformation of epoxy fatty acids to hydroxy-endoperoxides: a potential P450 and lipoxygenase interaction[S]

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Lipoxygenase-catalyzed transformation of epoxy fatty acids to hydroxy-endoperoxides: a potential P450 and lipoxygenase interaction.

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