RESUMEN

Bioassay-guided fractionation of an EtOAc extract of the leaves of Melampodium camphoratum using an assay for inhibitors of the degradation of hemin resulted in the isolation of six new eudesmane sesquiterpenes (1-6) and the known 6-epi-beta-verbesinol coumarate (7). The structures of compounds 1-6 were established as 6alpha-(4'-O-methyl-7'E-coumaryloxy)eudesm-4(14)-ene (1), 6alpha-({4'-O-stearyl}-7'E-coumaryloxy)eudesm-4(14)-ene (2), 6alpha-({4'-O-palmityl}-7'E-coumaryloxy)eudesm-4(14)-ene (3), 6alpha-({4'-O-[9' 'Z-hexadecenoyl]}-7'E-coumaryloxy)eudesm-4(14)-ene (4), 6alpha-(7'Z-coumaryloxy)eudesm-4(14)-ene (5), and 6alpha-({4'-acetoxy}-7'Z-coumaryloxy)eudesm-4(14)-ene (6). Compounds 1-4 showed weak activity in the hemin degradation assay, while compounds 5-7 were inactive.

Asunto(s)

Antimaláricos/aislamiento & purificación , Asteraceae/química , Hemina/metabolismo , Plantas Medicinales/química , Sesquiterpenos de Eudesmano/aislamiento & purificación , Animales , Antimaláricos/química , Antimaláricos/farmacología , Concentración 50 Inhibidora , Estructura Molecular , Hojas de la Planta/química , Plasmodium falciparum/efectos de los fármacos , Sesquiterpenos de Eudesmano/química , Sesquiterpenos de Eudesmano/farmacología , Estereoisomerismo , Suriname