title: Mooreamide A: a cannabinomimetic lipid from the marine cyanobacterium Moorea bouillonii.
abstract: Bioassay-guided fractionation of a collection of Moorea bouillonii from Papua New Guinea led to the isolation of a new alkyl amide, mooreamide A (1), along with the cytotoxic apratoxins A-C and E. The planar structure of 1 was elucidated by NMR spectroscopy and mass spectrometry analysis. Structural homology between mooreamide A and the endogenous cannabinoid ligands, anandamide, and 2-arachidonoyl glycerol inspired its evaluation against the neuroreceptors CB(1) and CB(2). Mooreamide A was found to possess relatively potent and selective ligand binding activity to CB(1) (K(1) = 0.47 µM) versus CB(2) (K(1) > 25 µM). This represents the most potent marine-derived CB(1) ligand described to date and adds to the growing family of marine metabolites that exhibit cannabinomimetic activity.
authors.affiliation: Center for Marine Biotechnology and Biomedicine, Scripps Institution of Oceanography, University of California San Diego, La Jolla, CA, 92093, USA.
authors.forename: Emily
authors.initials: E
authors.lastname: Mevers
authors.forename: Teatulohi
authors.initials: T
authors.lastname: Matainaho
authors.forename: Marco
authors.initials: M
authors.lastname: Allara'
authors.forename: Vincenzo
authors.initials: V
authors.lastname: Di Marzo
authors.forename: William H
authors.initials: WH
authors.lastname: Gerwick
mesh_terms: D001095:Arachidonic Acids / Q000032:analysis* / Q000737:chemistry / Q000378:metabolism; D001667:Binding, Competitive; D000458:Cyanobacteria / Q000737:chemistry*; D063388:Endocannabinoids / Q000032:analysis* / Q000737:chemistry / Q000378:metabolism; D057809:HEK293 Cells; D006801:Humans; D008055:Lipids / Q000032:analysis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D053284:Polyunsaturated Alkamides / Q000032:analysis* / Q000737:chemistry / Q000378:metabolism; D011869:Radioligand Assay; D043884:Receptor, Cannabinoid, CB1 / Q000378:metabolism; D043885:Receptor, Cannabinoid, CB2 / Q000378:metabolism; D012623:Seawater / Q000382:microbiology
chemical_list: D001095:Arachidonic Acids; D063388:Endocannabinoids; D008055:Lipids; D053284:Polyunsaturated Alkamides; D043884:Receptor, Cannabinoid, CB1; D043885:Receptor, Cannabinoid, CB2; C078814:anandamide