Rotenoids, Flavonoids, and Chalcones from the Root Bark of Millettia usaramensis
| Autor: | Máté Erdélyi, Sandra Duffy, Fangfang Pang, Abiy Yenesew, Vicky M. Avery, Ivan Gumula, Matthias Heydenreich, Michael Mumo, Göran Landberg, Solomon Derese, Paul A. Fitzpatrick, Kari Rissanen, Amra Gruhonjic, John P. Holleran, Tsegaye Deyou |
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| Rok vydání: | 2015 |
| Předmět: |
Stereochemistry
Plasmodium falciparum Molecular Conformation Pharmaceutical Science root bark Crystallography X-Ray 01 natural sciences Millettia Analytical Chemistry Millettia usaramensis chemistry.chemical_compound Antimalarials Chalcones Drug Discovery Plant Bark Humans ta116 IC50 Nuclear Magnetic Resonance Biomolecular ta317 metabolites Pharmacology Flavonoids Chromatography Natural product biology Molecular Structure 010405 organic chemistry Chemistry Plant Extracts Organic Chemistry Chloroquine biology.organism_classification 0104 chemical sciences 010404 medicinal & biomolecular chemistry Chromatographic separation HEK293 Cells Complementary and alternative medicine visual_art Flavanones visual_art.visual_art_medium Molecular Medicine Bark rotenoids |
| Zdroj: | Journal of natural products. 78(12) |
| ISSN: | 1520-6025 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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