Withanolides from leaves of cultivated Acnistus arborescens.
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.
['Batista|Pedro Henrique J|PH|', 'de Lima|Karísia Sousa B|KS|', 'Pinto|Francisco das Chagas L|Fd|', 'Tavares|Juliane L|JL|', 'de A Uchoa|Daniel E|DE|', 'Costa-Lotufo|Letícia V|LV|', 'Rocha|Danilo D|DD|', 'Silveira|Edilberto R|ER|', 'Bezerra|Antonio Marcos E|AM|', 'Canuto|Kirley M|KM|', 'Pessoa|Otília Deusdenia L|OD|']
D000972:Antineoplastic Agents, Phytogenic D004354:Drug Screening Assays, Antitumor D004875:Ergosterol D045325:HCT116 Cells D018922:HL-60 Cells D006801:Humans D015394:Molecular Structure D019906:Nuclear Magnetic Resonance, Biomolecular D018515:Plant Leaves D019657:Solanaceae D013237:Stereoisomerism D054358:Withanolides
Withanolides Acnistus arborescens Cytotoxic activity Solanaceae Withaphysalins