RESUMEN
Two new pyrrolinone-containing lipopeptides, ypaoamides B (1) and C (2), were isolated from an Okeania sp. marine cyanobacterium collected in Okinawa. Their structures were determined by spectroscopic analysis and Marfey's analysis of acid hydrolysates. Ypaoamides B (1) and C (2) stimulated glucose uptake in cultured rat L6 myotubes. In particular, ypaoamide B (1) showed potent activity and activated AMP-activated protein kinase.
Asunto(s)
Organismos Acuáticos/química , Cianobacterias/química , Lipopéptidos/química , Pirrolidinas/química , Animales , Línea Celular , Ensayos de Selección de Medicamentos Antitumorales/métodos , Ratas , Relación Estructura-ActividadRESUMEN
Three new compounds of the malyngamide series, 6,8-di-O-acetylmalyngamide 2 (1), 6-O-acetylmalyngamide 2 (2), and N-demethyl-isomalyngamide I (3), were isolated from the marine cyanobacterium Moorea producens. Their structures were determined by spectroscopic analysis and chemical derivatization and degradation. These compounds stimulated glucose uptake in cultured L6 myotubes. In particular, 6,8-di-O-acetylmalyngamide 2 (1) showed potent activity and activated adenosine monophosphate-activated protein kinase (AMPK).
Asunto(s)
Amidas/química , Organismos Acuáticos , Cianobacterias/química , Lipopéptidos/química , Pirroles/química , Amidas/farmacología , Animales , Glucemia/efectos de los fármacos , Lipopéptidos/farmacología , Espectroscopía de Resonancia Magnética , Estructura Molecular , Pirroles/farmacología , Relación Estructura-ActividadRESUMEN
Odoamide is a novel cyclic depsipeptide with highly potent cytotoxic activity isolated from the Okinawan marine cyanobacterium Okeania sp. It contains a 26-membered macrocycle composed of a fatty acid moiety, a peptide segment and isoleucic acid. Four possible stereoisomers of the odoamide polyketide substructure were synthesised using a chiral pool approach. The first total synthesis of odoamide was also successfully achieved. The structure of synthetic odoamide was verified by comparing its NMR spectra with those of the natural product.
Asunto(s)
Antineoplásicos/síntesis química , Cianobacterias/química , Depsipéptidos/síntesis química , Policétidos/síntesis química , Células A549 , Antineoplásicos/química , Antineoplásicos/farmacología , Proliferación Celular/efectos de los fármacos , Depsipéptidos/química , Depsipéptidos/farmacología , Ensayos de Selección de Medicamentos Antitumorales , Humanos , Neoplasias/tratamiento farmacológico , Policétidos/química , Policétidos/farmacología , EstereoisomerismoRESUMEN
Kanamienamide, an enamide with an enol ether, was isolated from the marine cyanobacterium Moorea bouillonii. The gross structure was established by spectroscopic analyses, and the relative stereochemistry was elucidated on the basis of the analyses of NOESY correlations and 1H-1H coupling constants. The absolute configuration was determined on the basis of the chiral HPLC analysis of the N-Me-Leu derived from kanamienamide. This is the first report of a natural product that possesses an N-Me-enamide adjacent to an enol ether. Kanamienamide showed growth-inhibitory activity toward HeLa cells with an IC50 value of 2.5 µM and induced apoptosis-like cell death.