Semiplenamides A-G, fatty acid amides from a Papua New Guinea collection of the marine cyanobacterium Lyngbya semiplena

Abstract

Semiplenamides A (1) to G (7), a series of new anandamide-like fatty acid amides, were isolated from a 1997 Papua New Guinea collection of the marine cyanobacterium Lyngbya semiplena. The planar structures of these lipids were determined using standard 1D and 2D NMR methods. The relative stereochemistry of the aliphatic portion of the new metabolites was deduced from 1D NOE data and (1)H-decoupling experiments, while the absolute stereochemistry of the amino alcohol moieties was assigned by chemical derivatization and chiral GC-MS methods. All of these new metabolites displayed toxicity in the brine shrimp model system, while semiplenamides A, B, and G showed weak affinity for the rat cannabinoid CB(1) receptor and semiplenamide A was a moderate inhibitor (IC(50) = 18.1 muM) of the anandamide membrane transporter (AMT).