Anti-plasmodial activities and X-ray crystal structures of rotenoids from Millettia usaramensis subspecies usaramensis

Abstract

The dichloromethane extract of the stem bark of Millettia usaramensis subspecies usaramensis showed anti-plasmodial activity against the chloroquine sensitive (D6) and chloroquine resistant (W2) strains of Plasmodium falciparum. Chromatographic separation of the extract led to the identification of a new rotenoid, (6aR,12aS)-2,3-methylenedioxy-9-methoxy-8-(3,3-dimethylallyl)-12a-hydroxyrotenoid (trivial name, usararotenoid C) along with known flavonoids (usararotenoid A, 12a-epimillettosin, 6a,12a-dehydromillettone, barbigerone and 4′-O-geranylisoliquiritigenin) as the anti-plasmodial principles. The structures were determined by spectroscopic analyses. CD and X-ray analyses established absolute configurations. A new anti-plasmodial rotenoid, 1, along with known flavonoids were isolated from the stem bark of Millettia usaramensis subspecies usaramensis. The structures were determined on the basis of spectroscopic evidence. CD and X-ray analysis established absolute configurations.