Anti-plasmodial activities and X-ray crystal structures of rotenoids from Millettia usaramensis subspecies usaramensis.
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.
D000818:Animals; D000962:Antimalarials / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D002738:Chloroquine / Q000494:pharmacology; D018360:Crystallography, X-Ray; D004351:Drug Resistance; D005419:Flavonoids / Q000737:chemistry / Q000302:isolation & purification; D020128:Inhibitory Concentration 50; D009682:Magnetic Resonance Spectroscopy; D033641:Millettia / Q000737:chemistry*; D015394:Molecular Structure; D024301:Plant Bark / Q000737:chemistry; D018547:Plant Stems / Q000737:chemistry; D010963:Plasmodium falciparum / Q000187:drug effects / Q000235:genetics; D012402:Rotenone / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*
D000962:Antimalarials; D005419:Flavonoids; D012402:Rotenone; D002738:Chloroquine