Bioactive compounds from Stuhlmannia moavi from the Madagascar dry forest

Abstract

Bioassay-directed fractionation of the leaf and root extracts of the antiproliferative Madagascar plant Stuhlmannia moavi afforded 6-acetyl-5,8-dihydroxy-2-methoxy-7-methyl-1,4-naphthoquinone (stuhlmoavin, 1) as the most active compound, with an IC50 value of 8.1 μM against the A2780 human ovarian cancer cell line, as well as the known homoisoflavonoid bonducellin (2) and the stilbenoids 3,4,5'-trihydroxy-3'-methoxy-trans-stilbene (3), piceatannol (4), resveratrol (5), rhapontigenin (6), and isorhapontigenin (7). The structure elucidation of all compounds was based on NMR and mass spectroscopic data, and the structure of 1 was confirmed by a single crystal X-ray analysis. Compounds 2-5 showed weak A2780 activities, with IC50 values of 10.6, 54.0, 41.0, and 74.0 μM, respectively. Compounds 1-3 also showed weak antimalarial activity against Plasmodium falciparum with IC50 values of 23, 26, and 27 μM, respectively.

Keywords: 1,4-Naphthoquinone; ANNNBEZJTNCXHY-NSCUHMNNSA-N; AOMAYOSPRMTXRK-NSCUHMNNSA-N; Antimalarial activity; Antiproliferative activity; CDRPUGZCRXZLFL-OWOJBTEDSA-N; DLQSYZMPSWHYMW-XYOKQWHBSA-N; Homoisoflavonoid; Leguminosae; PHMHDRYYFAYWEG-NSCUHMNNSA-N; PHRQNTXVBVJWJE-UHFFFAOYSA-N; QNVSXXGDAPORNA-SNAWJCMRSA-N; X-ray crystallography.