Bullatacin, bullatacinone, and squamone, a new bioactive acetogenin, from the bark of Annona squamosa.
Activity-directed fractionation of the stem bark of Annona squamosa, monitoring with brine shrimp lethality, led to the isolation of the highly bioactive acetogenins bullatacin [1] and bullatacinone [2], thus demonstrating a new abundant plant source for these potent compounds. A new keto-monotetrahydrofuran acetogenin with a ketolactone terminus, as first seen in bullatacinone [2], was also isolated, characterized by spectral analyses, and named squamone [3]. The cytotoxicities of 3 were increased significantly by reduction of the two keto groups to hydroxyls, and the tetrahydrosquamone [7] and bullatacinone [2] both showed selective cytotoxicities to MCF-7 human breast carcinoma. Liriodenine and (-)-kaur-16-en-19-oic acid were also isolated.
Li
X H
XH
Department of Medicinal Chemistry and Pharmacognosy, School of Pharmacy and Pharmacal Sciences, Purdue University, West Lafayette, Indiana 47907.
Hui
Y H
YH
Rupprecht
J K
JK
Liu
Y M
YM
Wood
K V
KV
Smith
D L
DL
Chang
C J
CJ
McLaughlin
J L
JL
D000972:Antineoplastic Agents, Phytogenic / Q000302:isolation & purification*; D004354:Drug Screening Assays, Antitumor; D005663:Furans / Q000302:isolation & purification / Q000494:pharmacology*; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D014407:Tumor Cells, Cultured
D000972:Antineoplastic Agents, Phytogenic; D005663:Furans; C061022:bullatacin; C061021:bullatacinone; C064336:squamone