title: Optimized synthesis and characterization of N-acylethanolamines and O-acylethanolamines, important family of lipid-signalling molecules.
abstract: The endocannabinoid anandamide (N-arachidonoylethanolamine, AEA), a physiologically occurring bioactive compound on CB1 and CB2 receptors, has multiple physiological functions. Since the discovery of AEA additional non-cannabinoid endogenous compounds such as N-palmitoylethanolamine (PEA), and N-oleoylethanolamine (OEA) have been identified from mammalian tissues. Virodhamine (O-arachidonoylethanolamine, VA) is the only identified new member of the endocannabinoid family that is characterised by an ester linkage between acylic acid and ethanolamine instead of the amide linkage found in AEA and others non-cannabinoid N-acylethanolamines. It has been reported, as a cautionary note for lipid analyses, that VA can be produced nonenzymatically from AEA (and vice versa) as consequence of O,N-acyl migrations. O,N-acyl migrations are well documented in synthetic organic chemistry literature, but are not well described or recognized with regard to methods in lipid isolation or lipid enzyme studies. We here report an economical and effective protocol for large scale synthesis and characterization of some N- and O-acylethanolamines that could be useful as reference standards in order to investigate their possible formation in biological membranes, with potentially interesting biological properties.
authors: Dipartimento di Scienze Biomediche e Cliniche Luigi Sacco, Università degli Studi di Milano, via G. B. Grassi, 74-20157 Milano, Italy.
authors: Roberta
authors: R
authors: Ottria
authors: Silvana
authors: S
authors: Casati
authors: Pierangela
authors: P
authors: Ciuffreda
mesh_terms: D001095:Arachidonic Acids; D063386:Cannabinoid Receptor Agonists / Q000737:chemistry; D063388:Endocannabinoids / Q000737:chemistry / Q000502:physiology; D004983:Ethanolamines / Q000138:chemical synthesis* / Q000737:chemistry; D008055:Lipids / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D053284:Polyunsaturated Alkamides; D012015:Reference Standards
chemical_list: D001095:Arachidonic Acids; D063386:Cannabinoid Receptor Agonists; D063388:Endocannabinoids; D004983:Ethanolamines; D008055:Lipids; C022203:N-acylethanolamines; D053284:Polyunsaturated Alkamides; C078814:anandamide