title: Three new bioactive bis-adjacent THF-ring acetogenins from the bark of Annona squamosa.
abstract: Continuing work on the bioactivity-directed fractionation of the bark of Annona squamosa has resulted in the discovery of three new Annonaceous acetogenins, (2,4-cis and trans)-squamolinone (1), (2,4-cis and trans)-9-oxoasimicinone (2), and bullacin B (3). Compounds 1-3 are all adjacent bis-THF ring acetogenins with 2 representing the first bis-ring acetogenin to contain a carbonyl along its aliphatic chain. Compound 3 was selectively cytotoxic in a panel of six human tumor cell lines with a potency of nearly a million times that of adriamycin against the MCF-7 (human breast adenocarcinoma) cell line.
authors.affiliation: Department of Medicinal Chemistry and Molecular Pharmacology, Purdue University, West Lafayette, IN 47907-1333, USA.
authors.forename: D C
authors.initials: DC
authors.lastname: Hopp
authors.forename: F Q
authors.initials: FQ
authors.lastname: Alali
authors.forename: Z M
authors.initials: ZM
authors.lastname: Gu
authors.forename: J L
authors.initials: JL
authors.lastname: McLaughlin
mesh_terms: D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D005663:Furans / Q000737:chemistry / Q000494:pharmacology*; D006801:Humans; D007783:Lactones / Q000737:chemistry / Q000494:pharmacology*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D013056:Spectrophotometry, Ultraviolet; D014197:Trees / Q000737:chemistry*; D014407:Tumor Cells, Cultured
chemical_list: D000972:Antineoplastic Agents, Phytogenic; D005663:Furans; D007783:Lactones; C112079:isomurisolenin