title: 4-deoxyannomontacin and (2,4-cis and trans)-annomontacinone, new bioactive mono-tetrahydrofuran annonaceous acetogenins from Goniothalamus giganteus.
abstract: 4-Deoxyannomontacin (1) and a mixture of (2,4-cis and trans)-annomontacinone (2), new bioactive mono-tetrahydrofuran (THF) gamma-lactone and keto-lactone acetogenins, respectively, as well as five known mono-THF acetogenins [xylomaticin, longifolicin, longicoricin, (2,4-cis and trans)-gigantetrocinone, and (2,4-cis and trans)-gigantetroneninone], were isolated from the bark of Goniothalamus giganteus (Annonaceae) by activity-directed fractionation using the brine shrimp lethality test (BST). The structures were elucidated based on spectroscopic and chemical methods. The absolute stereochemistries of 1 and 2 were determined by the advanced Mosher ester method and by circular dichroism (CD). Determination of the absolute stereochemistry at C-10 as R for 1 is the first example of the direct determination of the absolute stereochemistry of a carbinol position isolated from other functional groups in the annonaceous acetogenins. 1 and 2 showed selective and potent cytotoxicities to certain human tumor cell lines and were comparable to the activity of rotenone against yellow fever mosquito larvae.
authors.affiliation: Department of Medicinal Chemistry and Molecular Pharmacology, School of Pharmacy and Pharmacal Sciences, Purdue University, West Lafayette, IN 47907, USA.
authors.forename: F
authors.initials: F
authors.lastname: Alali
authors.forename: L
authors.initials: L
authors.lastname: Zeng
authors.forename: Y
authors.initials: Y
authors.lastname: Zhang
authors.forename: Q
authors.initials: Q
authors.lastname: Ye
authors.forename: D C
authors.initials: DC
authors.lastname: Hopp
authors.forename: J T
authors.initials: JT
authors.lastname: Schwedler
authors.forename: J L
authors.initials: JL
authors.lastname: McLaughlin
mesh_terms: D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000737:chemistry / Q000494:pharmacology; D000818:Animals; D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry* / Q000494:pharmacology; D001156:Artemia; D002942:Circular Dichroism; D009033:Culicidae; D005663:Furans / Q000737:chemistry* / Q000494:pharmacology; D008401:Gas Chromatography-Mass Spectrometry; D006801:Humans; D007783:Lactones / Q000737:chemistry* / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D051379:Mice; D014197:Trees / Q000737:chemistry*; D014407:Tumor Cells, Cultured
chemical_list: C107229:4-deoxyannomontacin; D000972:Antineoplastic Agents, Phytogenic; D005663:Furans; D007783:Lactones; C073066:annomontacin; D015107:4-Butyrolactone