title: New eudesmane derivatives from Melampodium camphoratum from the Suriname rainforest.
abstract: 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.
authors.affiliation: Department of Chemistry, M/C 0212, Virginia Polytechnic Institute and State University, Blacksburg, Virginia 24061, USA.
authors.forename: V S Prakash
authors.initials: VS
authors.lastname: Chaturvedula
authors.forename: Afgan
authors.initials: A
authors.lastname: Farooq
authors.forename: Jennifer K
authors.initials: JK
authors.lastname: Schilling
authors.forename: S
authors.initials: S
authors.lastname: Malone
authors.forename: Iwan
authors.initials: I
authors.lastname: Derveld
authors.forename: Marga C M
authors.initials: MC
authors.lastname: Werkhoven
authors.forename: Jan H
authors.initials: JH
authors.lastname: Wisse
authors.forename: Michel
authors.initials: M
authors.lastname: Ratsimbason
authors.forename: David G I
authors.initials: DG
authors.lastname: Kingston
mesh_terms: D000818:Animals; D000962:Antimalarials / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D019659:Asteraceae / Q000737:chemistry*; D006427:Hemin / Q000378:metabolism*; D020128:Inhibitory Concentration 50; D015394:Molecular Structure; D018515:Plant Leaves / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry*; D010963:Plasmodium falciparum / Q000187:drug effects; D045787:Sesquiterpenes, Eudesmane / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D013237:Stereoisomerism; D013532:Suriname
chemical_list: D000962:Antimalarials; D045787:Sesquiterpenes, Eudesmane; D006427:Hemin