With anandamide as substrate plant 5-lipoxygenases behave like 11-lipoxygenases

G van Zadelhoff, GA Veldink*, JFG Vliegenthart

*Corresponding author for this work

    Research output: Contribution to journalArticleAcademicpeer-review

    Abstract

    Anandamide, an endogenous ligand for cannabinoid receptors CB1 and CB2, was incubated with purified Ei-lipoxygenases from barley and tomato. This yielded 11S-hydroperoxy-5,8,12,14-eicosatetraenoylethanolamide (11S-HPANA) as major product (about 70%), This is in contrast with the dioxygenation of arachidonic acid, where 5S-HPETE is the major product. This observation implies that the regiospecificity of the dioxygenation, catalyzed by nonmammalian B-lipoxygenases, is altered by a modification at the carboxylic end of the substrate. Soybean 15-lipoxygenase forms 15S-HPANA (95%) and 11S-HPANA (5%), and in the second dioxygenation 5,15-diHPANA (45%) and 8,15-diHPANA (55%) are formed. Apparently, the regiospecificity of the soybean 15-lipoxygenase reaction is only slightly affected using anandamide as substrate. (C) 1998 Academic Press.

    Original languageEnglish
    Pages (from-to)33-38
    Number of pages6
    JournalBiochemical and Biophysical Research Communications
    Volume248
    Issue number1
    Publication statusPublished - 9 Jul 1998

    Keywords

    • CANNABINOID RECEPTOR
    • SOYBEAN LIPOXYGENASE-1

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