With anandamide as substrate plant 5-lipoxygenases behave like 11-lipoxygenases.
Anandamide, an endogenous ligand for cannabinoid receptors CB1 and CB2, was incubated with purified 5-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 5-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.
Bijvoet Center for Biomolecular Research, Department of Bio-organic Chemistry, Utrecht University, The Netherlands.
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van Zadelhoff
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Veldink
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Vliegenthart
D001094:Arachidonate 5-Lipoxygenase / Q000378:metabolism*; D001091:Arachidonate Lipoxygenases / Q000378:metabolism*; D016718:Arachidonic Acid / Q000378:metabolism; D001095:Arachidonic Acids / Q000378:metabolism*; D063388:Endocannabinoids; D004983:Ethanolamines / Q000378:metabolism; D005231:Fatty Acids, Unsaturated / Q000378:metabolism; D001467:Hordeum / Q000201:enzymology; D015289:Leukotrienes / Q000378:metabolism; D018551:Solanum lycopersicum / Q000201:enzymology; D010944:Plants / Q000201:enzymology*; D053284:Polyunsaturated Alkamides; D013025:Glycine max / Q000201:enzymology; D013379:Substrate Specificity
C113478:11-hydroperoxy-5,8,12,14-eicosatetraenoylethanolamide; D001095:Arachidonic Acids; D063388:Endocannabinoids; D004983:Ethanolamines; D005231:Fatty Acids, Unsaturated; D015289:Leukotrienes; D053284:Polyunsaturated Alkamides; D016718:Arachidonic Acid; C025348:arachidonic acid 5-hydroperoxide; C052641:11-lipoxygenase; D001091:Arachidonate Lipoxygenases; D001094:Arachidonate 5-Lipoxygenase; C078814:anandamide