RESUMO
NMR-guided fractionation of two independent collections of the marine cyanobacteria Lyngbya majuscula obtained from Papua New Guinea and Oscillatoria sp. collected in Panama led to the isolation of the new lipids serinolamide A (3) and propenediester (4). Their structures were determined by NMR and MS data analysis. Serinolamide A (3) exhibited a moderate agonist effect and selectivity for the CB1 cannabinoid receptor (Ki=1.3 µM, >5-fold) and represents the newest addition to the known cannabinomimetic natural products of marine origin.
Assuntos
Cianobactérias/química , Lipídeos/isolamento & purificação , Relação Dose-Resposta a Droga , Humanos , Lipídeos/química , Lipídeos/farmacologia , Biologia Marinha , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Panamá , Papua Nova Guiné , Receptor CB1 de Canabinoide/agonistasRESUMO
[reaction: see text] A new method for the synthesis of 1,5-diynes, from the reaction of 1,3-dilithiopropyne and propargyl chlorides, was developed. This new methodology was used to prepare (4E,6Z,10Z)-4,6,10-hexadecatrien-1-ol, one of the pheromone components of the cocoa pod borer moth Conopomorpha cramerella, in 51% overall yield.