title: Cytotoxic withanolide constituents of Physalis longifolia.
abstract: Fourteen new withanolides, 1-14, named withalongolides A-N, respectively, were isolated from the aerial parts of Physalis longifolia together with eight known compounds (15-22). The structures of compounds 1-14 were elucidated through spectroscopic techniques and chemical methods. In addition, the structures of withanolides 1, 2, 3, and 6 were confirmed by X-ray crystallographic analysis. Using a MTS viability assay, eight withanolides (1, 2, 3, 7, 8, 15, 16, and 19) and four acetylated derivatives (1a, 1b, 2a, and 2b) showed potent cytotoxicity against human head and neck squamous cell carcinoma (JMAR and MDA-1986), melanoma (B16F10 and SKMEL-28), and normal fetal fibroblast (MRC-5) cells with IC₅₀ values in the range between 0.067 and 9.3 μM.
authors.affiliation: Department of Medicinal Chemistry, School of Pharmacy, University of Kansas, Lawrence, Kansas 66045, USA.
authors.forename: Huaping
authors.initials: H
authors.lastname: Zhang
authors.forename: Abbas K
authors.initials: AK
authors.lastname: Samadi
authors.forename: Robert J
authors.initials: RJ
authors.lastname: Gallagher
authors.forename: Juan J
authors.initials: JJ
authors.lastname: Araya
authors.forename: Xiaoqin
authors.initials: X
authors.lastname: Tong
authors.forename: Victor W
authors.initials: VW
authors.lastname: Day
authors.forename: Mark S
authors.initials: MS
authors.lastname: Cohen
authors.forename: Kelly
authors.initials: K
authors.lastname: Kindscher
authors.forename: Rao
authors.initials: R
authors.lastname: Gollapudi
authors.forename: Barbara N
authors.initials: BN
authors.lastname: Timmermann
mesh_terms: D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D002294:Carcinoma, Squamous Cell; D018360:Crystallography, X-Ray; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D020128:Inhibitory Concentration 50; D007615:Kansas; D008968:Molecular Conformation; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D032321:Physalis / Q000737:chemistry*; D054358:Withanolides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*
chemical_list: C433551:3-rhamnopyranosyl(1-4)-glucopyranosyl-12-diacetoxy-20-hydroxywitha-5,24-dienolide; D000972:Antineoplastic Agents, Phytogenic; D054358:Withanolides
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