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New Eudesmane Derivatives from Melampodium camphoratum from the Suriname Rainforest

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posted on 28.12.2004, 00:00 authored by V. S. Prakash Chaturvedula, Afgan Farooq, Jennifer K. Schilling, S. Malone, Iwan Derveld, Marga C. M. Werkhoven, Jan H. Wisse, Michel Ratsimbason, David G. I. Kingston
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 (16) and the known 6-epi-β-verbesinol coumarate (7). The structures of compounds 16 were established as 6α-(4‘-O-methyl-7‘E-coumaryloxy)eudesm-4(14)-ene (1), 6α-({4‘-O-stearyl}-7‘E-coumaryloxy)eudesm-4(14)-ene (2), 6α-({4‘-O-palmityl}-7‘E-coumaryloxy)eudesm-4(14)-ene (3), 6α-({4‘-O-[9‘ ‘Z-hexadecenoyl]}-7‘E-coumaryloxy)eudesm-4(14)-ene (4), 6α-(7‘Z-coumaryloxy)eudesm-4(14)-ene (5), and 6α-({4‘-acetoxy}-7‘Z-coumaryloxy)eudesm-4(14)-ene (6). Compounds 14 showed weak activity in the hemin degradation assay, while compounds 57 were inactive.