title: A Synthetic Butenolide Diterpene is now a Natural Product Isolated from Metaporana sericosepala, a Plant from the Madagascar Dry Forest.
abstract: Antiproliferative bioassay-guided fractionation of the ethanolic extract of the endemic Madagascan plant Metaporana sericosepala led to the first natural product isolation of a butenolide diterpene, which was synthesized during an anti-inflammatory study in 1988. The structure of the compound was elucidated as 3-homofarnesyl-4-hydroxybutenolide (1) by analysis of its spectroscopic data, including 1D- and 2D-NMR data and chemical evidence. The once synthetic compound can now also be considered as a natural product. Compound 1 had modest antiproliferative activity towards the A2780 ovarian cancer cell line,with an IC50 value of 8 µM.
authors.forename: Christopher C
authors.initials: CC
authors.lastname: Presley
authors.forename: L Harinantenaina
authors.initials: LH
authors.lastname: Rakotondraibe
authors.forename: Peggy J
authors.initials: PJ
authors.lastname: Brodie
authors.forename: Martin W
authors.initials: MW
authors.lastname: Callmander
authors.forename: Richard
authors.initials: R
authors.lastname: Randrianaivo
authors.forename: Vincent E
authors.initials: VE
authors.lastname: Rasamison
authors.forename: Etienne
authors.initials: E
authors.lastname: Rakotobe
authors.forename: David G I
authors.initials: DG
authors.lastname: Kingston
mesh_terms: D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000737:chemistry; D001688:Biological Products / Q000737:chemistry*; D002980:Climate; D027722:Convolvulaceae / Q000737:chemistry*; D004224:Diterpenes / Q000737:chemistry*; D065928:Forests; D008270:Madagascar; D015394:Molecular Structure
chemical_list: D001688:Biological Products; D004224:Diterpenes; C004511:butenolide; D015107:4-Butyrolactone