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

Academic Article
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Overview

authors

  • Turman, M. V.
  • Kingsley, P. J.
  • Rouzer, C. A.
  • Cravatt, Benjamin
  • Marnett, L. J.

publication date

  • March 2008

journal

  • Biochemistry  Journal

abstract

  • 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.

subject areas

  • 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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Identity

PubMed Central ID

  • PMC2760074

International Standard Serial Number (ISSN)

  • 0006-2960

Digital Object Identifier (DOI)

  • 10.1021/bi702530z

PubMed ID

  • 18311922
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Additional Document Info

start page

  • 3917

end page

  • 3925

volume

  • 47

issue

  • 12

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