Characterization of the enzymatic and nonenzymatic reaction of 13-oxooctadecadienoic acid with glutathione

Chemical Research in Toxicology
M L BlackburnA W Bull

Abstract

The enzymatic oxygenation of linoleic acid leads to the production of 13-hydroxyoctadecadienoic acid (13-HODE). Subsequent dehydrogenation of 13-HODE by the NAD(+)-dependent 13-HODE dehydrogenase results in the formation of the 2,4-dienone 13-oxooctadecadienoic acid (13-OXO). These oxidized derivatives of linoleic acid have been shown to be involved in several cellular regulatory processes. In the present study, we have examined the enzymatic and nonenzymatic reaction of 13-OXO with glutathione (GSH) and N-acetylcysteine (N-AcCySH). Nonenzymatic reaction rates were determined spectrophotometrically and exhibited a pH optimum of 9.0 which is consistent with attack of a thiolate anion. Product formation was evaluated by reverse-phase HPLC which showed formation of one major product upon reaction with either GSH or N-AcCySH. The HPLC-purified products were examined by FAB MS as well as one- and two-dimensional NMR. The products, with either GSH or N-AcCySH, were found to consist of an equal mixture of two diastereomers arising from addition of a thiolate to the 9 position of 13-OXO. Using GSH as the thiol, the reaction was also shown to be catalyzed by rat glutathione transferase 8-8. In the case of the enzymatic reaction there is...Continue Reading

Citations

Nov 16, 2002·Prostaglandins & Other Lipid Mediators·Robert C Murphy, Simona Zarini
Jun 13, 2009·The Journal of Biological Chemistry·David P Dixon, Robert Edwards
Oct 7, 2009·Proceedings of the National Academy of Sciences of the United States of America·Paulina DabrowskaWilhelm Boland
Aug 5, 2000·The Journal of Biological Chemistry·R C BowersR C Murphy
Sep 10, 2019·Chemical Research in Toxicology·Adriano B Chaves-FilhoSayuri Miyamoto
Sep 26, 2007·Journal of Agricultural and Food Chemistry·Shengbao FengDejian Huang

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