Oxidative metabolism of a fatty acid amide hydrolase-regulated lipid, arachidonoyltaurine.

Turman MV, Kingsley PJ, Rouzer CA, Cravatt BF, Marnett LJ
Biochemistry. 2008 47 (12): 3917-25

PMID: 18311922 · PMCID: PMC2760074 · DOI:10.1021/bi702530z

A novel class of lipids, N-acyltaurines, was recently discovered in fatty acid amide hydrolase knockout mice. In some peripheral tissues, such as liver and kidney, N-acyltaurines with long, polyunsaturated acyl chains are most prevalent. Polyunsaturated fatty acids are converted to a variety of signaling molecules by cyclooxygenases (COXs) and lipoxygenases (LOXs). The ability of COXs and LOXs to oxygenate arachidonoyltaurine was evaluated to gain insight into the potential metabolic fate of N-acyltaurines. Although arachidonoyltaurine was a poor substrate for COXs, mammalian 12 S- and 15 S-LOXs oxygenated arachidonoyltaurine with similar or better efficiency than arachidonic acid. Products of arachidonoyltaurine oxygenation were characterized by liquid chromatography-tandem mass spectrometry (LC-MS/MS). The positional specificity of single oxygenation was retained for 15 S-LOXs. However, platelet-type 12 S-LOX produced 12- and 15-hydroxyeicosatetraenoyltaurines (HETE-Ts). Furthermore, LOXs generated dihydroxyeicosatetraenoyltaurines (diHETE-Ts). Metabolism of arachidonoyltaurine by murine resident peritoneal macrophages (RPMs) was also profiled. Arachidonoyltaurine was rapidly taken up and converted primarily to 12-HETE-T. Over prolonged incubations, RPMs also generated small amounts of diHETE-T. Oxidative metabolism of polyunsaturated N-acyltaurines may represent a pathway for the generation or termination of novel signaling molecules.

MeSH Terms (15)

Amidohydrolases Animals Arachidonate 12-Lipoxygenase Arachidonate 15-Lipoxygenase Arachidonic Acids Chromatography, Liquid Cyclooxygenase 2 Female Humans Kinetics Macrophages, Peritoneal Mass Spectrometry Mice Oxidation-Reduction Taurine

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