np030242n_si_002.pdf (18.66 kB)
Semiplenamides A−G, Fatty Acid Amides from a Papua New Guinea Collection of the Marine Cyanobacterium Lyngbya semiplena
journal contribution
posted on 2003-10-24, 00:00 authored by Bingnan Han, Kerry L. McPhail, Alessia Ligresti, Vincenzo Di Marzo, William H. GerwickSemiplenamides 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
1H-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 CB1 receptor and semiplenamide A was a moderate inhibitor (IC50 = 18.1 μM) of the
anandamide membrane transporter (AMT).
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alcohol moietiesMarine Cyanobacterium Lyngbyaaffinitychemical derivatizationAmideGCrat cannabinoid CB 1 receptormetaboliteAMTseriesaliphatic portion1997 Papua New Guinea collectionexperimentlipidbrine shrimp model systemanandamide membrane transporterchiraltoxicitymarine cyanobacterium Lyngbya semiplena2 D NMR methods1 D NOE dataacid amides1 DinhibitorIC 50FattyPapua New Guinea Collectionstereochemistrysemiplenamideemiplena Semiplenamides18.1 μ M
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