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Three Chalconoids and a Pterocarpene from the Roots of Tephrosia aequilata.

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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