Isolation, structures, and structure-cytotoxic activity relationships of withanolides and physalins from Physalis angulata

Amooru G. Damu, Ping Chung Kuo, Chung Ren Su, Tsung Hsiao Kuo, Tzu Hsuan Chen, Kenneth F. Bastow, Kuo Hsiung Lee, Tian Shung Wu

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98 Citations (Scopus)

Abstract

Phytochemical investigation of Physalis angulata was initiated following primary biological screening. Fractionation of CHCl3 and n-BuOH solubles of the MeOH extract from the whole plant was guided by in vitro cytotoxic activity assay 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 and MS) 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 human cancer cell lines with EC50 values ranging from 0.2 to 1.6 μg/mL. Structure-activity relationship analysis indicated that withanolides and physalins with 4β-hydroxy-2-en-1-one and 5β,6β-epoxy moieties are potential cytotoxic agents.

Original languageEnglish
Pages (from-to)1146-1152
Number of pages7
JournalJournal of Natural Products
Volume70
Issue number7
DOIs
Publication statusPublished - 2007 Jul

All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Molecular Medicine
  • Pharmacology
  • Pharmaceutical Science
  • Drug Discovery
  • Complementary and alternative medicine
  • Organic Chemistry

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