Transformations of manool. tri- and tetracyclic norditerpenoids with in vitro activity against Plasmodium falciparum.
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.
van Wyk
Albert W W
AW
Department of Chemistry, Rhodes University, Grahamstown, South Africa.
Lobb
Kevin A
KA
Caira
Mino R
MR
Hoppe
Heinrich C
HC
Davies-Coleman
Michael T
MT
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*
D000962:Antimalarials; D004224:Diterpenes; C482828:manool