RESUMEN
Novel proanthocyanidin fractions from grape stem extracts were purified using Amberlite XAD-1180N, Sephadex-LH-20, Toyopearl HW40F and reverse phase high-performance liquid chromatography. Two key compounds were estimated as epigallocatechin-(epicatechin)7 gallate using electron-spray ionization time-of-flight mass spectrometry. Epigallocatechin-(epicatechin)7 gallate (compound 1) showed significant anti-cancer activity in PC-3 prostate cancer cells. In particular, compound 1 suppressed the gene expression of fatty acid-binding protein 5 (FABP5), which is involved in promoting cell proliferation and metastasis in prostate cancer cells.
Asunto(s)
Antineoplásicos Fitogénicos/química , Extractos Vegetales/química , Tallos de la Planta/química , Polímeros , Proantocianidinas/química , Vitis/química , Antineoplásicos Fitogénicos/aislamiento & purificación , Puntos de Control del Ciclo Celular/efectos de los fármacos , Línea Celular Tumoral , Proliferación Celular/efectos de los fármacos , Cromatografía Líquida de Alta Presión , Proteínas de Unión a Ácidos Grasos/genética , Regulación Neoplásica de la Expresión Génica/efectos de los fármacos , Humanos , Espectroscopía de Resonancia Magnética , Extractos Vegetales/aislamiento & purificación , Proantocianidinas/aislamiento & purificaciónRESUMEN
Synthesis of arrecatannin A1 (1) was accomplished from dimeric epicatechin electrophile, which was prepared by Zn(OTf)2 mediated self-condensation, and monomeric catechin nucleophile. The condensation was successfully worked using Yb(OTf)3 as a Lewis acid in good yield.