title: Withanolide artifacts formed in methanol.
abstract: Methanol solutions of the main withanolides (6-8) naturally present in Physalis longifolia yielded five artificial withanolides (1-5), including three new compounds (1-3). Withanolides 1 and 2 were identified as intramolecular Michael addition derivatives, while withanolides 3-5 were the result of intermolecular Michael addition. A comprehensive literature investigation was conducted to identify potential withanolide Michael addition artifacts isolated from Solanaceous species to date.
authors.affiliation: Department of Medicinal Chemistry, University of Kansas , Lawrence, Kansas 66045, United States.
authors.forename: Cong-Mei
authors.initials: CM
authors.lastname: Cao
authors.forename: Huaping
authors.initials: H
authors.lastname: Zhang
authors.forename: Robert J
authors.initials: RJ
authors.lastname: Gallagher
authors.forename: Barbara N
authors.initials: BN
authors.lastname: Timmermann
mesh_terms: D004875:Ergosterol / Q000031:analogs & derivatives; D000432:Methanol / Q000737:chemistry*; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D032321:Physalis / Q000737:chemistry*; D054358:Withanolides / Q000737:chemistry* / Q000302:isolation & purification
chemical_list: C433551:3-rhamnopyranosyl(1-4)-glucopyranosyl-12-diacetoxy-20-hydroxywitha-5,24-dienolide; D054358:Withanolides; C493689:withanolide-5; D000432:Methanol; D004875:Ergosterol