New derivatives of a natural nordentatin

Abstract

New derivatives were obtained from natural nordentatin (1) previously isolated from the methanol fraction of Clausena excavata by an acylation method. Herein, we report ten new pyranocoumarin derivatives 1a–1j. Their structures were elucidated based on UV-vis, FT-IR, NMR, and DART-MS data. The α-glucosidase inhibition and anticancer activities of nordentatin (1) and its derivatives were also evaluated. The α-glucosidase inhibition assay exhibited that the derivatives 1b, 1d, 1e, 1f, 1h, 1i, and 1j possess higher inhibitory activity for α-glucosidase with IC50 values of 1.54, 9.05, 4.87, 20.25, 12.34, 5.67, and 2.43 mM, whereas acarbose was used as the positive control, IC50 = 7.57 mM. All derivatives exhibited a weak cytotoxicity against a cervical cancer (HeLa) cell line with the IC50 between 0.25 and 1.25 mM. They also showed moderate to low growth inhibition of a breast cancer (T47D) cell line with IC50 values between 0.043 and 1.5 mM, but their activity was lower than that of the parent compound, nordentatin (1) (IC50 = 0.041 mM).

Keywords

• clausena excavata
• pyranocoumarin derivatives
• nordentatin
• yeast α-glucosidase inhibition
• cytotoxicity
• cervical cancer
• breast cancer