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Molecules 2017, 22(2), 318; doi:10.3390/molecules22020318

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
Received: 7 January 2017 / Revised: 1 February 2017 / Accepted: 14 February 2017 / Published: 20 February 2017
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Abstract

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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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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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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