title: Withanolides from leaves of cultivated Acnistus arborescens.
abstract: Seven withanolides, including four previously unknown, were isolated from the acetone and ethanol extracts of cultivated specimens of Acnistus arborescens. These four compounds were identified as rel-(18R,22R)-5β,6β:18β,20-diepoxy-3β,18α-dimethoxy-4β-hydroxy-1-oxowith-24-enolide, rel-(20R,22R)-5β,6β-epoxy-4β,16α,20-trihydroxy-1-oxowitha-2,24dienolide, rel-(20R,22R)-16α-acetoxy-6α-chloro-4β,5β,20-trihydroxy-1-oxowitha-2,24-dienolide and rel-(20R,22R)-16α-acetoxy-20-hydroxy-1-oxowitha-2,5,24-trienolide. Their structures were elucidated by interpretation of spectroscopic data (1D and 2D NMR), HRESIMS experiments and comparison with published data for similar compounds. Cytotoxicity of the isolated compounds was evaluated against a panel of four tumor cell lines (HL-60, HCT-116, SF-268 and PANC-1). Withanolide D was the most active, with an IC50 value in the range of 0.3-1.7 μM, rel-(18R,22R)-5β,6β:18β,20-diepoxy-3β,18α-dimethoxy-4β-hydroxy-1-oxowith-24-enolide and rel-(20R,22R)-5β,6β-epoxy-4β,16α,20-trihydroxy-1-oxowitha-2,24dienolide were moderately active, while all the others were non-cytotoxic.
authors: Departamento de Química Orgânica e Inorgânica, Centro de Ciências, Universidade Federal do Ceará, 60021-970, Fortaleza, CE, Brazil.
authors: Pedro Henrique J
authors: PH
authors: Batista
authors: Departamento de Química Orgânica e Inorgânica, Centro de Ciências, Universidade Federal do Ceará, 60021-970, Fortaleza, CE, Brazil.
authors: Karísia Sousa B
authors: KS
authors: de Lima
authors: Departamento de Química Orgânica e Inorgânica, Centro de Ciências, Universidade Federal do Ceará, 60021-970, Fortaleza, CE, Brazil.
authors: Francisco das Chagas L
authors: Fd
authors: Pinto
authors: Departamento de Química Orgânica e Inorgânica, Centro de Ciências, Universidade Federal do Ceará, 60021-970, Fortaleza, CE, Brazil.
authors: Juliane L
authors: JL
authors: Tavares
authors: Departamento de Química Orgânica e Inorgânica, Centro de Ciências, Universidade Federal do Ceará, 60021-970, Fortaleza, CE, Brazil.
authors: Daniel E
authors: DE
authors: de A Uchoa
authors: Departamento de Farmacologia, Universidade de São Paulo, 05508-900, São Paulo, SP, Brazil.
authors: Letícia V
authors: LV
authors: Costa-Lotufo
authors: Departamento de Fisiologia e Farmacologia, Universidade Federal do Ceará, 60165-081, Fortaleza, CE, Brazil.
authors: Danilo D
authors: DD
authors: Rocha
authors: Departamento de Química Orgânica e Inorgânica, Centro de Ciências, Universidade Federal do Ceará, 60021-970, Fortaleza, CE, Brazil.
authors: Edilberto R
authors: ER
authors: Silveira
authors: Núcleo de Estudos e Pesquisa em Agricultura Urbana, Departamento de Fitotecnia, Centro de Ciências Agrárias, Universidade Federal do Ceará, 60356-000, Fortaleza, CE, Brazil.
authors: Antonio Marcos E
authors: AM
authors: Bezerra
authors: Embrapa Tropical Agroindustry, R. Dra. Sara Mesquita, 2270, 60511-110, Fortaleza, CE, Brazil.
authors: Kirley M
authors: KM
authors: Canuto
authors: Departamento de Química Orgânica e Inorgânica, Centro de Ciências, Universidade Federal do Ceará, 60021-970, Fortaleza, CE, Brazil. Electronic address: opessoa@ufc.br.
authors: Otília Deusdenia L
authors: OD
authors: Pessoa
mesh_terms: D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D004354:Drug Screening Assays, Antitumor; D004875:Ergosterol / Q000737:chemistry; D045325:HCT116 Cells; D018922:HL-60 Cells; D006801:Humans; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D018515:Plant Leaves / Q000737:chemistry; D019657:Solanaceae / Q000737:chemistry*; D013237:Stereoisomerism; D054358:Withanolides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology
chemical_list: D000972:Antineoplastic Agents, Phytogenic; D054358:Withanolides; D004875:Ergosterol
keywords: Acnistus arborescens; Cytotoxic activity; Solanaceae; Withanolides; Withaphysalins