title: Lauroylethanolamide is a potent competitive inhibitor of lipoxygenase activity.
abstract: The lipoxygenase (LOX) pathway was proposed to compete with hydrolysis and be partly responsible for the metabolism of polyunsaturated N-acylethanolamines (PU-NAEs). Treatment of Arabidopsis seedlings with lauroylethanolamide (NAE 12:0) resulted in elevated levels of PU-NAE species, and this was most pronounced in plants with reduced NAE hydrolase activity. Enzyme activity assays revealed that NAE 12:0 inhibited LOX-mediated oxidation of PU lipid substrates in a dose-dependent and competitive manner. NAE 12:0 was 10-20 times more potent an inhibitor of LOX activities than lauric acid (FFA 12:0). Furthermore, treatment of intact Arabidopsis seedlings with NAE 12:0 (but not FFA 12:0) substantially blocked the wound-induced formation of jasmonic acid (JA), suggesting that NAE 12:0 may be used in planta to manipulate oxylipin metabolism.
authors.affiliation: University of North Texas, Center for Plant Lipid Research, Department of Biological Sciences, Denton, TX 76203, USA.
authors.forename: Jantana
authors.initials: J
authors.lastname: Keereetaweep
authors.forename: Aruna
authors.initials: A
authors.lastname: Kilaru
authors.forename: Ivo
authors.initials: I
authors.lastname: Feussner
authors.forename: Barney J
authors.initials: BJ
authors.lastname: Venables
authors.forename: Kent D
authors.initials: KD
authors.lastname: Chapman
mesh_terms: D017360:Arabidopsis / Q000201:enzymology / Q000378:metabolism; D003517:Cyclopentanes; D057075:Enzyme Assays; D004983:Ethanolamines; D006868:Hydrolysis; D007850:Lauric Acids; D008055:Lipids; D008084:Lipoxygenase / Q000378:metabolism*; D054883:Oxylipins; D010944:Plants / Q000201:enzymology / Q000378:metabolism; D036226:Seedlings / Q000201:enzymology / Q000378:metabolism
chemical_list: D003517:Cyclopentanes; D004983:Ethanolamines; D007850:Lauric Acids; D008055:Lipids; C022203:N-acylethanolamines; D054883:Oxylipins; C030358:lauric acid; C011006:jasmonic acid; D008084:Lipoxygenase