Antiplasmodial prenylated flavanonols from Tephrosia subtriflora

Abstract

The CH2Cl2/MeOH (1:1) extract of the aerial parts of Tephrosia subtriflora afforded a new flavanonol, named subtriflavanonol (1), along with the known flavanone spinoflavanone B, and the known flavanonols MS-II (2) and mundulinol. The structures were elucidated by the use of NMR spectroscopy and mass spectrometry. The absolute configuration of the flavanonols was determined based on quantum chemical ECD calculations. In the antiplasmodial assay, compound 2 showed the highest activity against chloroquine-sensitive Plasmodium falciparum reference clones (D6 and 3D7), artemisinin-sensitive isolate (F32-TEM) as well as field isolate (KSM 009) with IC50 values 1.4–4.6 μM without significant cytotoxicity against Vero and HEp2 cell lines (IC50 > 100 μM). The new compound (1) showed weak antiplasmodial activity, IC50 12.5–24.2 μM, but also showed selective anticancer activity against HEp2 cell line (CC50 16.9 μM).