title: Goniothalamicin and annonacin: bioactive acetogenins from Goniothalamus giganteus (Annonaceae).
abstract: Using brine shrimp lethality for activity-directed fractionation, goniothalamicin (I), a new tetrahydroxy-mono-tetrahydrofuran fatty acid gamma-lactone (acetogenin), has been isolated from ethanolic extracts of the stem bark of Goniothalamus giganteus Hook. f., Thomas (Annonaceae). This novel compound was found to be cytotoxic and insecticidal and inhibited the formation of crown gall tumors on potato discs. Annonacin (II), the only other reported mono-tetrahydrofuran acetogenin, was also isolated; the previously reported 9ASK (astrocytoma reversal) activity of II was confirmed, and II is now also found to be weakly active against 3PS murine leukemia.
authors.affiliation: Department of Medicinal Chemistry and Pharmacognosy, School of Pharmacy and Pharmacal Sciences, Purdue University, West Lafayette, Indiana 47907.
authors.forename: A
authors.initials: A
authors.lastname: Alkofahi
authors.forename: J K
authors.initials: JK
authors.lastname: Rupprecht
authors.forename: D L
authors.initials: DL
authors.lastname: Smith
authors.forename: C J
authors.initials: CJ
authors.lastname: Chang
authors.forename: J L
authors.initials: JL
authors.lastname: McLaughlin
mesh_terms: D000818:Animals; D001156:Artemia / Q000187:drug effects; D055598:Chemical Phenomena; D002621:Chemistry; D004175:Diptera; D005663:Furans / Q000302:isolation & purification / Q000494:pharmacology* / Q000627:therapeutic use; D007306:Insecticides; D007783:Lactones / Q000302:isolation & purification / Q000494:pharmacology* / Q000627:therapeutic use; D007945:Leukemia, Lymphoid / Q000188:drug therapy; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D051379:Mice; D009303:Nasopharyngeal Neoplasms / Q000188:drug therapy; D010941:Plant Tumors; D010944:Plants / Q000032:analysis*
chemical_list: D005663:Furans; D007306:Insecticides; D007783:Lactones; C055449:goniothalamicin; C053442:annonacin