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Three Chalconoids and a Pterocarpene from the Roots of Tephrosia aequilata

Journal article
Authors Y. Atilaw
S. Duffy
M. Heydenreich
L. Muiva-Mutisya
V. M. Avery
Mate Erdelyi
A. Yenesew
Published in Molecules
Volume 22
Issue 2
ISSN 1420-3049
Publication year 2017
Published at Swedish NMR Centre at Göteborg University
Department of Chemistry and Molecular Biology
Language en
Keywords Tephrosia aequilata, chalcone, retrochalcone, aequichalcone A, aequichalcone B, aequichalcone C, natural-products, flavonoids, retrochalcone, candida, bark, seed, Chemistry
Subject categories Chemical Sciences, Organic Chemistry, Pharmacognosy, Pharmaceutical Sciences, Pharmaceutical chemistry, Medicinal Chemistry


In our search for new antiplasmodial agents, the CH2Cl2/CH3OH (1:1) extract of the roots of Tephrosia aequilata was investigated, and observed to cause 100% mortality of the chloroquine-sensitive (3D7) strain of Plasmodium falciparum at a 10 mg/mL concentration. From this extract three new chalconoids, E-2,6-dimethoxy-3,4-(2,2-dimethyl)pyranoretrochalcone (1, aequichalcone A), Z-2,6-dimethoxy-3,4-(2,2-dimethyl)pyranoretrochalcone (2, aequichalcone B), 4-ethoxy-3-hydroxypraecansone B (3, aequichalcone C) and a new pterocarpene, 3,4:8,9-dimethylenedioxy-6a,11a-pterocarpene (4), along with seven known compounds were isolated. The purified compounds were characterized by NMR spectroscopic and mass spectrometric analyses. Compound 1 slowly converts into 2 in solution, and thus the latter may have been enriched, or formed, during the extraction and separation process. The isomeric compounds 1 and 2 were both observed in the crude extract. Some of the isolated constituents showed good to moderate antiplasmodial activity against the chloroquine-sensitive (3D7) strain of Plasmodium falciparum.

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