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Open AccessArticle

Three Chalconoids and a Pterocarpene from the Roots of Tephrosia aequilata

1
Department of Chemistry, University of Nairobi, P.O. Box 30197, 00100 Nairobi, Kenya
2
Discovery Biology, Griffith Institute for Drug Discovery, Griffith University, Nathan, QLD 4111, Australia
3
Institut für Chemie, Universität Potsdam, Karl-Liebknecht-Str. 24-25, D-14476 Potsdam, Germany
4
Department of Chemistry and Molecular Biology, University of Gothenburg, SE-412 96 Gothenburg, Sweden
5
Swedish NMR Centre, University of Gothenburg, SE-405 30 Gothenburg, Sweden
*
Authors to whom correspondence should be addressed.
Academic Editor: Derek J. McPhee
Molecules 2017, 22(2), 318; https://doi.org/10.3390/molecules22020318
Received: 7 January 2017 / Revised: 1 February 2017 / Accepted: 14 February 2017 / Published: 20 February 2017
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. View Full-Text
Keywords: Tephrosia aequilata; chalcone; retrochalcone; aequichalcone A; aequichalcone B; aequichalcone C; pterocarpene; antiplasmodial Tephrosia aequilata; chalcone; retrochalcone; aequichalcone A; aequichalcone B; aequichalcone C; pterocarpene; antiplasmodial
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MDPI and ACS Style

Atilaw, Y.; Duffy, S.; Heydenreich, M.; Muiva-Mutisya, L.; Avery, V.M.; Erdélyi, M.; Yenesew, A. Three Chalconoids and a Pterocarpene from the Roots of Tephrosia aequilata. Molecules 2017, 22, 318.

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