The possible role of 9(S)-hydroperoxyoctadecatrienoic acid as a suicide substrate of soybean lipoxygenase

Biochem Biophys Res Commun. 1989 Aug 15;162(3):1357-62. doi: 10.1016/0006-291x(89)90823-1.

Abstract

While incubation of soybean lipoxygenase with alpha-linolenic acid resulted in the gradual decrease of lipoxygenase activity, the incubation with linoleic acid had no change. The inactivation of soybean lipoxygenase during incubation with alpha-linolenic acid was markedly observed at pH 6.5, but not at pH 9.0. Among the lipoxygenation products of alpha-linolenic acid, only 9(S)-hydroperoxyoctadecatrienoic acid caused the inactivation of lipoxygenase. 9(S)-Hydroxyoctadecatrienoic acid, 13(S)-hydroperoxyoctadecatrienoic acid or 9,16-dihydroperoxy conjugated trienoic acid was without effect. Accordingly, it is suggested that the epoxide intermediate, one conversion product of 9(S)-hydroperoxyoctadecatrienoic acid, might be involved in the direct inactivation of lipoxygenase.

MeSH terms

  • Epoxy Compounds
  • Glycine max / enzymology*
  • Kinetics
  • Linolenic Acids / metabolism
  • Lipid Peroxides / metabolism*
  • Lipid Peroxides / pharmacology
  • Lipoxygenase / metabolism*
  • Lipoxygenase Inhibitors
  • Mass Spectrometry
  • Oxidation-Reduction
  • alpha-Linolenic Acid

Substances

  • Epoxy Compounds
  • Linolenic Acids
  • Lipid Peroxides
  • Lipoxygenase Inhibitors
  • alpha-Linolenic Acid
  • 9-hydroperoxy-10,12,15-octadecatrienoic acid
  • Lipoxygenase