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

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 stereochemi...

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Bibliographic Details
Published in:Journal of natural products (Washington, D.C.) D.C.), 2003-10, Vol.66 (10), p.1364-1368
Main Authors: BINGNAN HAN, MCPHAIL, Kerry L, LIGRESTI, Alessia, DI MARZO, Vincenzo, GERWICK, William H
Format: Article
Language:English
Subjects:
Amides - chemistry
Amides - isolation & purification
Amides - pharmacology
Animals
Antibiotics, microbial producers, chemotherapic agents, antiseptics, disinfecting agents
Applied microbiology
Arachidonic Acids
Artemia
Artemia - drug effects
Biological and medical sciences
Chemotherapic agents
Cyanobacteria - chemistry
Cyanophyta
Disease Models, Animal
Endocannabinoids
Fatty Acids, Unsaturated - chemistry
Fatty Acids, Unsaturated - isolation & purification
Fatty Acids, Unsaturated - pharmacology
Fundamental and applied biological sciences. Psychology
Inhibitory Concentration 50
Lyngbya semiplena
Marine
Membrane Transport Modulators
Membrane Transport Proteins - antagonists & inhibitors
Microbiology
Molecular Structure
natural products
Nuclear Magnetic Resonance, Biomolecular
Papua New Guinea
Polyunsaturated Alkamides
Rats
Receptor, Cannabinoid, CB1 - drug effects
semiplenamides
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Summary: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).
ISSN:0163-3864
1520-6025
DOI:10.1021/np030242n