Formation of octadecadienoate dimers by soybean lipoxygenases

L.M. Van der Heijdt, F. Van der Lecq, A. Lachmansingh, K. Versluis, A.V.D. Kerk-van Hoof, G.A. Veldink, J.F.G. Vliegenthart

    Research output: Contribution to journalArticleAcademicpeer-review


    The aim of this investigation was to determine whether the regioselectivity found for lipoxygenases in the formation of fatty acid hydroperoxides from linoleic acid is reflected in the formation of dimeric products in secondary reactions involving linoleic acid, product hydroperoxide and lipoxygenase. A method was therefore developed for the separation and identification of dimers formed by fusion of two linoleic acid radicals or a linoleic acid radical and linoleate. The method includes solid- phase extraction, preparative separation of products by thin-layer chromatography, derivatization to the corresponding fully hydrogenated methyl esters and capillary gas chromatography (GC) coupled with electron impact mass spectrometry. We present evidence that the formation of octadecadienoate dimers, during the secondary reaction of soybean lipoxygenase-1 or lipoxygenase-3, is a nonenzymic process that can be envisaged by nonspecific association of intermediate fatty acid radicals (L*) that have dissociated from the enzyme. We could show that the relative amounts of different octadecadienoate dimers formed remain unaltered, regardless of pH and type of soybean isoenzyme used. Quantitative analysis by GC showed that under the reaction conditions used, the formation of dimers branching at the 13- position is preferred.
    Original languageEnglish
    Pages (from-to)779-782
    Number of pages4
    Issue number9
    Publication statusPublished - 12 Jul 1993


    • dimer
    • hydroperoxide
    • isoenzyme
    • linoleic acid
    • lipoxygenase
    • long chain fatty acid
    • radical
    • article
    • controlled study
    • dimerization
    • enzyme specificity
    • fatty acid metabolism
    • gas chromatography
    • human
    • mass spectrometry
    • pH
    • priority journal
    • soybean
    • thin layer chromatography


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