Squamotacin: an annonaceous acetogenin with cytotoxic selectivity for the human prostate tumor cell line (PC-3).
The bark extracts of Annona squamosa yielded a new bioactive acetogenin, squamotacin (1), and the known compound, molvizarin (2), which is new to this species. Compound 1 is identical to the potent acetogenin, bullatacin (3), except that the adjacent bistetrahydrofuran (THF) rings and their flanking hydroxyls are shifted two carbons toward the gamma-lactone ring. Compound 1 showed cytotoxic selectively for the human prostate tumor cell line (PC-3), with a potency of over 100 million times that of Adriamycin.
Hopp
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Department of Medicinal Chemistry and Pharmacognosy, Purdue University, West Lafayette, Indiana 47907-1333, USA.
Zeng
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Gu
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McLaughlin
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JL
D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000302:isolation & purification / Q000494:pharmacology; D000818:Animals; D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D001156:Artemia / Q000187:drug effects; D001943:Breast Neoplasms / Q000188:drug therapy; D003110:Colonic Neoplasms / Q000188:drug therapy; D006801:Humans; D007680:Kidney Neoplasms / Q000188:drug therapy; D008175:Lung Neoplasms / Q000188:drug therapy; D008297:Male; D010190:Pancreatic Neoplasms / Q000188:drug therapy; D010946:Plants, Medicinal / Q000737:chemistry*; D011471:Prostatic Neoplasms / Q000188:drug therapy; D014407:Tumor Cells, Cultured
D000972:Antineoplastic Agents, Phytogenic; C102771:squamotacin; D015107:4-Butyrolactone