Wedelolides A and B: novel sesquiterpene delta-lactones, (9R)-eudesman-9,12-olides, from Wedelia trilobata.
Two new sesquiterpene lactones, wedelolides A (1) and B (2), were isolated by bioassay-guided fractionation from the leaves of Wedelia trilobata, together with known trilobolides 6-O-isobutyrate (3) and 6-O-methacrylate (4). The compounds 1 and 2 were the first examples of an unprecedented framework: a novel sesquiterpene delta-lactone, (9R)-eudesman-9,12-olide. The structures of the antimalarial wedelolides A (1) and B (2) were determined on the basis of MS and 2D NMR spectral analysis. The absolute configuration of eight carbon stereocenters of compounds 1 and 2 was determined to be 1S,4S,5S,6R,7S,8S,9R,10S by mean of auxiliary chiral MTPA derivatives.
That
Quang Ton
QT
Laboratoire de Chimie et Biochimie des Substances Naturelles, UMR 5154 Centre National de la Recherche Scientifique, USM 502, Muséum National d'Histoire Naturelle, 63 rue Buffon, 75005 Paris, France.
Jossang
Jean
J
Jossang
Akino
A
Kim
Phi Phung Nguyen
PP
Jaureguiberry
Ginette
G
D000818:Animals; D000962:Antimalarials / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D007783:Lactones / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D019906:Nuclear Magnetic Resonance, Biomolecular; D010963:Plasmodium falciparum / Q000187:drug effects; D045787:Sesquiterpenes, Eudesmane / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D031209:Wedelia / Q000737:chemistry*
D000962:Antimalarials; D007783:Lactones; D045787:Sesquiterpenes, Eudesmane; C015872:eudesmane