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Mooreamide A: A cannabinomimetic lipid from the marine cyanobacterium Moorea bouillonii

TitleMooreamide A: A cannabinomimetic lipid from the marine cyanobacterium Moorea bouillonii
Publication TypeJournal Article
Year of Publication2014
AuthorsMevers E., Matainaho T., Allara M., Di Marzo V., Gerwick WH
Date Published2014/11
Type of ArticleArticle
ISBN Number0024-4201
Accession NumberWOS:000344151800005
KeywordsAcyl; amide; Cannabinoid; collection; cyanobacteria; drug discovery; evolution; fatty-acid amides; HPLC; lyngbya-majuscula; Marine natural product; metabolites; Mooreamide; natural-products; neurobiology; nmr; potent; receptors

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 CB1 and CB2. Mooreamide A was found to possess relatively potent and selective ligand binding activity to CB1 (K (1) = 0.47 A mu M) versus CB2 (K (1) > 25 A mu M). This represents the most potent marine-derived CB1 ligand described to date and adds to the growing family of marine metabolites that exhibit cannabinomimetic activity.

Short TitleLipids
Student Publication: 
Research Topics: