The possible role of 9(S)-hydroperoxyoctadecatrienoic acid as a suicide substrate of soybean lipoxygenase.
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.
Sok
D E
DE
Department of Food and Nutrition, Chungnam National University, Daejeon, Korea.
Kim
M R
MR
D004852:Epoxy Compounds; D007700:Kinetics; D008042:Linolenic Acids / Q000378:metabolism; D008054:Lipid Peroxides / Q000378:metabolism* / Q000494:pharmacology; D008084:Lipoxygenase / Q000378:metabolism*; D016859:Lipoxygenase Inhibitors; D013058:Mass Spectrometry; D010084:Oxidation-Reduction; D013025:Glycine max / Q000201:enzymology*; D017962:alpha-Linolenic Acid
D004852:Epoxy Compounds; D008042:Linolenic Acids; D008054:Lipid Peroxides; D016859:Lipoxygenase Inhibitors; D017962:alpha-Linolenic Acid; C060746:9-hydroperoxy-10,12,15-octadecatrienoic acid; D008084:Lipoxygenase