Gigantetronenin and gigantrionenin: novel cytotoxic acetogenins from Goniothalamus giganteus.
Gigantetronenin [1] and gigantrionenin [6], two new monotetrahydrofuran Annonaceous acetogenins each possessing a double bond along the hydrocarbon chain, have been isolated from the bark of Goniothalamus giganteus by the use of brine shrimp lethality for bioactivity-directed fractionation. The structures were elucidated based on spectroscopic and chemical methods. Compounds 1 and 6 both show selective and potent cytotoxicities to human tumor cells in culture as well as toxicity to brine shrimp. A known cytotoxic acetogenin, annomontacin [11], was also isolated from this plant. The biogenetic pathway of the acetogenins from G. giganteus is discussed.
Fang
X P
XP
Department of Medicinal Chemistry and Pharmacognosy, Purdue University, West Lafayette, Indiana 47907.
Anderson
J E
JE
Smith
D L
DL
McLaughlin
J L
JL
Wood
K V
KV
D000818:Animals; D000972:Antineoplastic Agents, Phytogenic / Q000138:chemical synthesis* / Q000494:pharmacology / Q000633:toxicity; D001156:Artemia; D005663:Furans / Q000138:chemical synthesis* / Q000494:pharmacology / Q000633:toxicity; D006801:Humans; D007783:Lactones / Q000138:chemical synthesis* / Q000494:pharmacology / Q000633:toxicity; D010946:Plants, Medicinal / Q000737:chemistry*; D014407:Tumor Cells, Cultured
D000972:Antineoplastic Agents, Phytogenic; D005663:Furans; D007783:Lactones; C079193:gigantetronenin