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Rotenoids, Flavonoids, and Chalcones from the Root Bark of Millettia usaramensis

Deyou, Tsegaye, Gumula, Ivan, Pang, Fangfang, Gruhonjic, Amra, Mumo, Michael, Holleran, John, Duffy, Sandra, Fitzpatrick, Paul A., Heydenreich, Matthias, Landberg, Göran, Derese, Solomon, Avery, Vicky, Rissanen, Kari, Erdélyi, Máté, Yenesew, Abiy
Journal of natural products 2015 v.78 no.12 pp. 2932-2939
Millettia, Plasmodium falciparum, X-ray diffraction, antiparasitic properties, bark, breast neoplasms, chalcones, chromatography, cytotoxicity, humans, hydroxyl radicals, inhibitory concentration 50, metabolites, nuclear magnetic resonance spectroscopy, rotenoids
Five new compounds, 4-O-geranylisoliquiritigenin (1), 12-dihydrousararotenoid B (2), 12-dihydrousararotenoid C (3), 4′-O-geranyl-7-hydroxyflavanone (4), and 4′-O-geranyl-7-hydroxydihydroflavanol (5), along with 12 known natural products (6–17) were isolated from the CH₂Cl₂/MeOH (1:1) extract of the root bark of Millettia usaramensis ssp. usaramensis by chromatographic separation. The purified metabolites were identified by NMR spectroscopic and mass spectrometric analyses, whereas their absolute configurations were established on the basis of chiroptical data and in some cases also by X-ray crystallography. The crude extract was moderately active (IC₅₀ = 11.63 μg/mL) against the ER-negative MDB-MB-231 human breast cancer cell line, and accordingly compounds 6, 8, 9, 10, 12, and 16 also showed moderate to low cytotoxic activities (IC₅₀ 25.7–207.2 μM). The new natural product 1 exhibited antiplasmodial activity with IC₅₀ values of 3.7 and 5.3 μM against the chloroquine-sensitive 3D7 and the chloroquine-resistant Dd2 Plasmodium falciparum strains, respectively, and was also cytotoxic to the HEK293 cell line.