Journal
LIPIDS
Volume 49, Issue 11, Pages 1127-1132Publisher
WILEY
DOI: 10.1007/s11745-014-3949-9
Keywords
Marine natural product; Mooreamide; Cyanobacteria; Cannabinoid; Acyl amide; HPLC; NMR
Funding
- Growth Regulation & Oncogenesis Training Grant NIH/NCI [T32A009523-24]
- NIH [CA100851, NS053398]
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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.
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