Isolation of bioactive and other oxoaporphine alkaloids from two annonaceous plants, Xylopia aethiopica and Miliusa cf. banacea.
The oxoaporphine alkaloids oxophoebine [1] and liriodenine [2] have been isolated from Xylopia aethiopica (Annonaceae). Both showed selective toxicity against DNA repair and recombination deficient mutants of the yeast Saccharomyces cerevisae. Three related but inactive compounds, oxoglaucine [3], O-methylmoschatoline [4], and lysicamine [5], were also isolated from this plant. Selective toxicity was also observed for 10-methoxyliriodenine (lauterine) [6] and 10-hydroxyliriodenine [7], two oxoaporphine alkaloids isolated from Miliusa cf. banacea (Annonaceae). The structure of 10-hydroxyliriodenine [7], a novel oxoaporphine, was determined by spectroscopic methods and chemical conversion to compound 6. The role of the bioactive oxoaporphine alkaloids as DNA topoisomerase inhibitors is discussed.
Harrigan
G G
GG
Department of Chemistry, Virginia Polytechnic Institute and State University, Blacksburg, 24061-0212.
Gunatilaka
A A
AA
Kingston
D G
DG
Chan
G W
GW
Johnson
R K
RK
D000972:Antineoplastic Agents, Phytogenic / Q000302:isolation & purification* / Q000494:pharmacology; D001060:Aporphines / Q000302:isolation & purification* / Q000494:pharmacology; D001315:Australia; D004260:DNA Repair / Q000187:drug effects; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D007214:Indonesia; D007624:KB Cells / Q000187:drug effects; D009682:Magnetic Resonance Spectroscopy; D009154:Mutation; D010936:Plant Extracts / Q000494:pharmacology; D010944:Plants / Q000737:chemistry*; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet; D059004:Topoisomerase I Inhibitors; D015003:Yeasts / Q000187:drug effects / Q000235:genetics
D000972:Antineoplastic Agents, Phytogenic; D001060:Aporphines; D010936:Plant Extracts; D059004:Topoisomerase I Inhibitors; C086774:oxophoebine; C026980:liriodenine