RESUMEN
Seven new guaiane-type sesquiterpene dimers vieloplains A-G, connecting patterns through three different direct CC bonds compounds 1-5 (C-3 to C-3', C-4 to C-1'), compound 6 (C-2 to C-3', C-4 to C-2') and compound 7 (C-2 to C-1', C-4 to C-2') were isolated from the roots of Xylopia vielana. Their absolute configurations were established by NOESY analysis, the Cu Kα X-ray crystallographic the experiment circular dichroism (ECD) and the calculated ECD. Among them, only compound 6 showed a considerable cytotoxicity against DU145 cells with IC50 values of 9.5⯵M. Flow cytometry analysis confirmed that 6 caused death of DU145 cells via apoptosis induction.
Asunto(s)
Antineoplásicos/farmacología , Sesquiterpenos de Guayano/farmacología , Xylopia/química , Antineoplásicos/química , Antineoplásicos/aislamiento & purificación , Apoptosis/efectos de los fármacos , Línea Celular Tumoral , Puntos de Control de la Fase G2 del Ciclo Celular/efectos de los fármacos , Humanos , Pruebas de Sensibilidad Microbiana , Estructura Molecular , Raíces de Plantas/química , Sesquiterpenos de Guayano/química , Sesquiterpenos de Guayano/aislamiento & purificación , EstereoisomerismoRESUMEN
Six rare guaiane-type sesquiterpene dimers xylopins A-F, having three different connecting modes through two direct C-C bonds, were isolated from the roots of Xylopia vielana. Their absolute configurations were established by NOESY analysis, Cu Kα X-ray crystallography, and experimental and calculated electronic circular dichroism spectra. Flow cytometry demonstrated the fact that compound 6 arrested the cell cycle at G2 phase and concentration-dependently induced apoptosis of DU145 cells. Furthermore, the EPT2-TGC cell model, zebrafish study and western blot analysis illustrated compound 6 could induce apoptosis by efficiently inhibiting the Wnt/ß-catenin signaling pathway via decreasing the expression of ß-catenin.
