title: Rotenoids, Flavonoids, and Chalcones from the Root Bark of Millettia usaramensis.
abstract: 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.
authors.affiliation: Department of Chemistry, University of Nairobi , P.O. Box 30197-00100, Nairobi, Kenya.
authors.forename: Tsegaye
authors.initials: T
authors.lastname: Deyou
authors.affiliation: Department of Chemistry, University of Nairobi , P.O. Box 30197-00100, Nairobi, Kenya.
authors.forename: Ivan
authors.initials: I
authors.lastname: Gumula
authors.affiliation: Department of Chemistry, Nanoscience Center, University of Jyvaskyla , P.O. Box. 35, FI-40014 Jyvaskyla, Finland.
authors.forename: Fangfang
authors.initials: F
authors.lastname: Pang
authors.forename: Amra
authors.initials: A
authors.lastname: Gruhonjic
authors.affiliation: Department of Chemistry, University of Nairobi , P.O. Box 30197-00100, Nairobi, Kenya.
authors.forename: Michael
authors.initials: M
authors.lastname: Mumo
authors.affiliation: Discovery Biology, Eskitis Institute for Drug Discovery, Griffith University , Nathan Qld 4111 Australia.
authors.forename: John
authors.initials: J
authors.lastname: Holleran
authors.affiliation: Discovery Biology, Eskitis Institute for Drug Discovery, Griffith University , Nathan Qld 4111 Australia.
authors.forename: Sandra
authors.initials: S
authors.lastname: Duffy
authors.forename: Paul A
authors.initials: PA
authors.lastname: Fitzpatrick
authors.affiliation: Institut für Chemie, Universität Potsdam , Karl-Liebknecht-Straße 24-25, D-1146, Potsdam, Germany.
authors.forename: Matthias
authors.initials: M
authors.lastname: Heydenreich
authors.forename: Göran
authors.initials: G
authors.lastname: Landberg
authors.affiliation: Department of Chemistry, University of Nairobi , P.O. Box 30197-00100, Nairobi, Kenya.
authors.forename: Solomon
authors.initials: S
authors.lastname: Derese
authors.affiliation: Discovery Biology, Eskitis Institute for Drug Discovery, Griffith University , Nathan Qld 4111 Australia.
authors.forename: Vicky
authors.initials: V
authors.lastname: Avery
authors.affiliation: Department of Chemistry, Nanoscience Center, University of Jyvaskyla , P.O. Box. 35, FI-40014 Jyvaskyla, Finland.
authors.forename: Kari
authors.initials: K
authors.lastname: Rissanen
authors.forename: Máté
authors.initials: M
authors.lastname: Erdélyi
authors.affiliation: Department of Chemistry, University of Nairobi , P.O. Box 30197-00100, Nairobi, Kenya.
authors.forename: Abiy
authors.initials: A
authors.lastname: Yenesew
mesh_terms: D000962:Antimalarials / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D047188:Chalcones / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D002738:Chloroquine / Q000494:pharmacology; D018360:Crystallography, X-Ray; D044950:Flavanones; D005419:Flavonoids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D057809:HEK293 Cells; D006801:Humans; D033641:Millettia / Q000737:chemistry*; D008968:Molecular Conformation; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D024301:Plant Bark / Q000737:chemistry; D010936:Plant Extracts / Q000737:chemistry; D010963:Plasmodium falciparum / Q000187:drug effects
chemical_list: D000962:Antimalarials; D047188:Chalcones; D044950:Flavanones; D005419:Flavonoids; D010936:Plant Extracts; C059353:7-hydroxyflavanone; D002738:Chloroquine