RESUMEN
A chemical investigation of the fibrous roots of Anemarrhena asphodeloides Bge. led to the isolation of four benzophenones, including one new compound (1) and three known ones (2-4). Comprehensive 1D, 2D NMR and HRESIMS data established the structures of the isolated compounds. The absolute configurations were determined by comparison of the calculated optical rotation (OR) with experimental data. All the isolates were evaluated for their cytotoxicities on hepatocellular carcinoma cell lines (HepG2 and Hep3B). Compound 1 showed strong cytotoxicity against HepG2 and Hep3B cells, with IC50 values at 153.1 and 180.6 nM. Through MTT assay, flow cytometry and Western blot analysis, compound 1 demonstrated the ability to stimulate apoptosis via the NF-κB signaling pathway in HepG2 cells. These benzophenones are potential lead compounds for the development of better treatments for hepatocellular carcinoma.
Asunto(s)
Anemarrhena/química , Antineoplásicos Fitogénicos/farmacología , Benzofenonas/farmacología , Extractos Vegetales/farmacología , Antineoplásicos Fitogénicos/química , Apoptosis/efectos de los fármacos , Benzofenonas/química , Supervivencia Celular/efectos de los fármacos , Células Hep G2 , Humanos , Espectroscopía de Resonancia Magnética , Estructura Molecular , FN-kappa B/metabolismo , Extractos Vegetales/química , Raíces de Plantas/química , Transducción de Señal/efectos de los fármacos , Relación Estructura-ActividadRESUMEN
Five compounds were isolated from the fibrous roots of Anemarrhena asphodeloides by silica gel, Sephadex LH-20 and semi-HPLC column chromatography. On the basis of physic-chemical properties and spectroscopic data analysis, these compounds were identified as methyl 2-[2,4-dihydroxy-3-(4-hydroxybenzoyl)-6-methoxyphenyl]acetate(1), 4-[formyl-5-(methoxymethyl)-1H-pyrrol-1-yl]butanoate(2), perlolyrine(3),syringaresinol-4'-O-ß-D-glucoside(4) and 4',6-dihydroxy-4-methoxybenzophenone-2-O-(2â³),3-C-(1â³)-1â³-desoxy-α-L-fructofuranoside(5). Among them, 1 was a new benzophenone. Compounds 2-5 were isolated from this plant for the first time. Compound 1 was tested for neuroprotective effects against H_2O_2-induced damage in SH-SY5 Y cells.
Asunto(s)
Anemarrhena/química , Benzofenonas/farmacología , Fármacos Neuroprotectores/farmacología , Raíces de Plantas/química , Benzofenonas/aislamiento & purificación , Línea Celular , Cromatografía Líquida de Alta Presión , Humanos , Fármacos Neuroprotectores/aislamiento & purificación , Fitoquímicos/aislamiento & purificación , Fitoquímicos/farmacologíaRESUMEN
One new benzophenone (1) and one new 1,3-diphenylpropane (2) were obtained from the fibrous roots of Anemarrhena asphodeloides Bge. Their structures were determined by comprehensive 1D, 2D NMR and HRESIMS data. By comparing the calculated ECD curves and OR with the experimental data the absolute configurations were determined. The antitumor activity of all isolates was evaluated against two human hepatoma carcinoma cells (HepG2 and Hep3B) in vitro. The results demonstrated that compound 1 and 2 showed potent cytotoxicity against HepG2 and Hep3B cells.