Antiplasmodial β-hydroxydihydrochalcone from seedpods of Tephrosia elata

Phytochemistry Letters
2009.0

Abstract

In East Africa Tephrosia species (Leguminosae) are used in traditional medicinal practice to treat infectious diseases and are rich in flavonoids and isoflavonoids including rotenoids. Previous phytochemical investigation of the roots of T. elata yielded flavanones, a flavone, pterocarpans and rotenoids. Using the new non-radioactive SYBR Green 1 malaria drug assay technique, we analyzed the seedpods of T. elata and report the isolation and identification of a new antiplasmodial b-hydroxydihydrochalcone, named elatadihydrochalcone (1), along with known flavonoids. The structures were determined on the basis of spectroscopic evidence. The crude extract and the flavonoids obtained from the seedpods showed antiplasmodial activities against chloroquine-sensitive Sierra Leone I (D6) and chloroquine-resistant Indochina I (W2) strains of Plasmodium falciparum. The new compound (1) exhibited good antiplasmodial activity with IC50 values of 2.8 - 0.3 and 5.5 - 0.3 mg/ml against D6 and W2 strains, respectively. We also reviewed literature NMR data on b-hydroxydihydrochalcones and questioned the identity of some compounds assigned b-hydroxydihydrochalcone skeleton, suggesting they could be flavanones rather than b-hydroxydihydrochalcone derivatives and recommending re-examination by modern spectroscopic techniques.

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