Synthesis and biological evaluation of the glycoside (25R)-3β,16β-diacetoxy-22-oxocholest-5-en-26-yl β-d-glucopyranoside: A selective anticancer agent in cervicouterine cell lines

The synthesis and biological evaluation of the new cholestane glycoside (25R)-3β,16β-diacetoxy-22-oxocholest-5-en-26-yl β-d-glucopyranoside starting from diosgenin is described. This compound showed selective antiproliferative activity against CaSki, ViBo, and HeLa cervicouterine cancer cells. Its effect on the cell-cycle was determined. The cytotoxic effects of the title compound on cervicouterine cancer cell lines and human lymphocytes indicate that the main cell death process is not necrosis; hence it is not cytotoxic. The title compound induced apoptosis in cervicouterine cancer cells. Importantly, the antiproliferative activity on tumor cells did not affect the proliferative potential of peripheral blood lymphocytes. The title compound showed selective antitumor activity and greater antiproliferative activity than its aglycon, and therefore serves as a promising lead candidate for further optimization.

Graphical abstractThe synthesis and biological evaluation of a new cholestane glycoside starting from diosgenin is described. This compound shows selective antitumor activity, and induces apoptosis against cervicouterine cancer cells.Figure optionsDownload full-size imageDownload as PowerPoint slideHighlights► A new cholestane glycoside was synthesized starting from diosgenin. ► Antiproliferative activity against CaSki, HeLa and ViBo cells is described. ► Proliferative potential on lymphocytes was not negatively affected. ► Cell-cycle and apoptosis assays were determined to establish anticancer activity. ► Cytotoxicity was tested in tumoral and healthy cells to demonstrate selectivity.