title: Oxygenation of Anandamide by Lipoxygenases.
abstract: The endocannabinoids anandamide and 2-arachidonoylglycerol are not only metabolized by serine hydrolases, such as fatty acid amide hydrolase, monoacylglycerol lipase, and α,β-hydrolases 6 and 12, but they also serve as substrates for cyclooxygenases and lipoxygenases. These enzymes oxygenate the 1Z,4Z-pentadiene system of the arachidonic acid backbone of endocannabinoids, thereby giving rise to an entirely new array of bioactive lipids. Hereby, a protocol is provided for the enzymatic synthesis, purification, and characterization of various oxygenated metabolites of anandamide generated by lipoxygenases, which enables the biological study and detection of these metabolites.
authors.affiliation: Cellular Protein Chemistry, Faculty of Science, Utrecht University, Padualaan 8, 3584 CH, Utrecht, The Netherlands.
authors.forename: Guus
authors.initials: G
authors.lastname: van Zadelhoff
authors.affiliation: Department Molecular Physiology, Leiden Institute of Chemistry, Leiden University, Einsteinweg 55, 2333 CC, Leiden, The Netherlands. m.van.der.stelt@chem.leidenuniv.nl.
authors.forename: Mario
authors.initials: M
authors.lastname: van der Stelt
mesh_terms: D001095:Arachidonic Acids / Q000378:metabolism*; D063388:Endocannabinoids / Q000378:metabolism*; D008401:Gas Chromatography-Mass Spectrometry; D005989:Glycerides / Q000378:metabolism; D058945:Lipoxygenases / Q000378:metabolism*; D010084:Oxidation-Reduction; D053284:Polyunsaturated Alkamides / Q000378:metabolism*; D066244:Proton Magnetic Resonance Spectroscopy; D013025:Glycine max / Q000201:enzymology
chemical_list: D001095:Arachidonic Acids; D063388:Endocannabinoids; D005989:Glycerides; D053284:Polyunsaturated Alkamides; C094503:glyceryl 2-arachidonate; D058945:Lipoxygenases; C078814:anandamide
keywords: 2-Arachidonoylglycerol; Anandamide; Endocannabinoid; Lipoxygenase; Oxygenated metabolite