title: Transformations of manool. tri- and tetracyclic norditerpenoids with in vitro activity against Plasmodium falciparum.
abstract: The known 17-norisopimar-15-ene-8beta,13beta-diol (5) and five new semisynthetic norditerpenoids, ethyl 17-norabiet-13(15)-E-en-8beta-ol-16-oate (6), ethyl 17-norabiet-13(15)-Z-en-8beta-ol-16-oate (7), 17-norpimaran-13alpha-ethoxy-8,16-olactone (8), 17-norisopimarane-8beta,15-diol (9), and 17-norarabiet-13(15)-ene-8beta,16-diol (10), were prepared from manool (11). Standard spectroscopic data including X-ray crystal analysis were used to determine the structures of 5-10. All five compounds exhibited in vitro antiplasmodial activity against the malarial parasite Plasmodium falciparum at varying microg mL(-1) concentrations.
authors.affiliation: Department of Chemistry, Rhodes University, Grahamstown, South Africa.
authors.forename: Albert W W
authors.initials: AW
authors.lastname: van Wyk
authors.forename: Kevin A
authors.initials: KA
authors.lastname: Lobb
authors.forename: Mino R
authors.initials: MR
authors.lastname: Caira
authors.forename: Heinrich C
authors.initials: HC
authors.lastname: Hoppe
authors.forename: Michael T
authors.initials: MT
authors.lastname: Davies-Coleman
mesh_terms: D000818:Animals; D000962:Antimalarials / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D018360:Crystallography, X-Ray; D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D004912:Erythrocytes / Q000378:metabolism; D006801:Humans; D008968:Molecular Conformation; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010963:Plasmodium falciparum / Q000187:drug effects*
chemical_list: D000962:Antimalarials; D004224:Diterpenes; C482828:manool