Prenylated flavones from some IndonesianArtocarpusand their antimalarial properties

Abstract

Artocarpus, locally known as “nangka-nangkaan”, is one of the important genera of family Moraceae. The plants belong to this genus grow endemically and also cultivated throughout Indonesian region. In this study, a phytochemical study on three species of Artocarpus, namely A. heterophyllus, A. elasticus and A. lanceifolius, has been carried out, and the biological effects of the isolated compounds against Plasmodium palcifarum strain K1 and 3D7 have been evaluated. The phytochemical investigation of these plants resulted, three new prenylated flavones, trivially named artoindonesianin E-1 (1), artoindonesianin Z-4 (2) and artoindonesianin Z-5 (3), beside seventeen known prenylated flavones. Antimalarial effect of some selected isolated flavone derivatives showed that artonin E exhibited very strong inhibition (IC50 0.1 mg/mL) against K1 strain in comparison against 3D7 strain of Plasmodium falciparum (IC50 0.3 mg/mL). A related prenylated flavone, namely 12-hydroxyartonin E, exhibited strong inhibition (IC50 0.9 mg/mL) against K1 strain, but weak inhibition (IC50 14.3 mg/mL) against 3D7 strain. Those two compounds were the member of 3-prenylflavone type. In addition, the other isolated flavone derivatives showed moderate inhibition with IC50 respectively 2.1, 1.6, 3.6, 1.3, 6.7 and 2.1 mg/mL against both the strain of P. falciparum, except for flavanone-3-ol derivative (dihydromorin), which had no inhibition.