title: New bioactive monotetrahydrofuran Annonaceous acetogenins, annomuricin C and muricatocin C, from the leaves of Annona muricata.
abstract: The leaves of Annona muricata have yielded two additional monotetrahydrofuran Annonaceous acetogenins, annomuricin C [1] and muricatocin C [2]. Compounds 1 and 2 each possess five hydroxyl groups; two hydroxyl groups are at the C-10/C-11 and C-10/C-12 positions in 1 and 2, respectively. The absolute configurations of 1 and 2, except for positions C-10 and C-11 or C-12, were determined by Mosher ester methodology. The C-10/C-11 and C-10/C-12 acetonides (1c, 2c) suggested relative stereochemistry and significantly enhanced the cytotoxicities against the A-549 human lung and the MCF-7 human beast solid tumor cell lines. One known monotetrahydrofuran acetogenin, gigantetronenin, not described previously from this plant, was also found.
authors.affiliation: Department of Medicinal Chemistry and Pharmacognosy, School of Pharmacy and Pharmacal Sciences, Purdue University, West Lafayette, Indiana 47907, USA.
authors.forename: F E
authors.initials: FE
authors.lastname: Wu
authors.forename: L
authors.initials: L
authors.lastname: Zeng
authors.forename: Z M
authors.initials: ZM
authors.lastname: Gu
authors.forename: G X
authors.initials: GX
authors.lastname: Zhao
authors.forename: Y
authors.initials: Y
authors.lastname: Zhang
authors.forename: J T
authors.initials: JT
authors.lastname: Schwedler
authors.forename: J L
authors.initials: JL
authors.lastname: McLaughlin
authors.forename: S
authors.initials: S
authors.lastname: Sastrodihardjo
mesh_terms: D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000032:analysis / Q000302:isolation & purification / Q000494:pharmacology; D000972:Antineoplastic Agents, Phytogenic / Q000032:analysis / Q000302:isolation & purification* / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D005663:Furans / Q000032:analysis / Q000302:isolation & purification* / Q000494:pharmacology; D006801:Humans; D007214:Indonesia; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008968:Molecular Conformation; D010946:Plants, Medicinal / Q000737:chemistry*; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet; D014407:Tumor Cells, Cultured
chemical_list: D000972:Antineoplastic Agents, Phytogenic; D005663:Furans; C095611:annomuricin A; C095614:muricatocin A; D015107:4-Butyrolactone