Isolation, Structures, and Structure-Cytotoxic Activity Relationships of Withanolides and Physalins from Physalis angulata

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• 作者：Amooru G. Damu ; Ping-Chung Kuo ; Chung-Ren Su ; Tsung-Hsiao Kuo ; Tzu-Hsuan Chen ; Kenneth F. Bastow ; Kuo-Hsiung Lee ; Tian-Shung Wu
• 刊名：Journal of Natural Products
• 出版年：2007
• 出版时间：July 2007
• 年：2007
• 卷：70
• 期：7
• 页码：1146 - 1152
• 全文大小：88K
• 年卷期：v.70,no.7(July 2007)
• ISSN：1520-6025

文摘

Phytochemical investigation of Physalis angulata was initiated following primary biological screening. Fractionationof CHCl₃ and n-BuOH solubles of the MeOH extract from the whole plant was guided by in vitro cytotoxic activityassay using cultured HONE-1 and NUGC cells and led to the isolation of seven new withanolides, withangulatins B-H(1-7), and a new minor physalin, physalin W (8), along with 14 known compounds, including physaprun A,withaphysanolide, dihydrowithanolide E, physanolide A, withaphysalin A, and physalins B, D, F, G, I, J, T, U, and V.New compounds (1-8) were fully characterized by a combination of spectroscopic methods (1D and 2D NMR andMS) and the relative stereochemical assignments based on NOESY correlations and analysis of coupling constants.Biological evaluation of these compounds against a panel of human cancer cell lines showed broad cytotoxic activity.Withangulatin B (1) and physalins D (10) and F (11) displayed potent cytotoxic activity against a panel of humancancer cell lines with EC₅₀ values ranging from 0.2 to 1.6 g/mL. Structure-activity relationship analysis indicatedthat withanolides and physalins with 4ta2.gif" BORDER=0 ALIGN="middle">-hydroxy-2-en-1-one and 5ta2.gif" BORDER=0 ALIGN="middle">,6ta2.gif" BORDER=0 ALIGN="middle">-epoxy moieties are potential cytotoxic agents.