Biologically active xanthones from Codonopsis ovata

Abstract

Five new xanthones, named coxanthones A–E (1–5), together with 21 known secondary metabolites (6–26) that include seven xanthones, five flavonoids, two steroids and seven triterpenoids were isolated from the chemically unexplored whole plant Codonopsis ovata. The structures of new metabolites were elucidated by HRMS, interpretation of NMR spectra and other spectroscopic techniques. The absolute configuration of the stereogenic centre of coxanthone B (2) was determined by electronic circular dichroism (ECD) spectroscopy. This is the first report of xanthones from the genus Codonopsis. All isolated metabolites were evaluated for cytotoxic activity by SRB assay against six human cancer cell lines A549 (lung), PC-3 (prostate), HCT-116 (colon), MCF-7 (breast), SF-295 (CNS), and MDAMB-435 (melanoma). Among the new compounds, coxanthone B (2) exhibited significant inhibitory activity against SF-295 and MDAMB-435 with IC50 values of 7.0 and 15.0 μM, respectively. Coxanthone A (1) displayed cytotoxicity against A549 cell line at IC50 value of 22.5 μM. Cytotoxic activity of 1-hydroxy-3,5-dimethoxyxanthone (7), swertiperenine (9) and 1,7,8-trihydroxy-3-methoxyxanthone (10) are reported here first time that exhibited the IC50 values of 3.0, 5.0 and 21.0 μM against A549, MDAMB-435, and A549 cell lines, respectively. Kaempferol (13) showed most potent cytotoxic activity with an IC50 values in the 1.0–2.3 μM range against all tested cancer cell lines.