Induction of quinone reductase by withanolides

J Nat Prod. 2002 May;65(5):677-80. doi: 10.1021/np0106337.

Abstract

Thirty-seven naturally occurring withanolides (1-37), previously isolated in our laboratories, were evaluated for their potential to induce quinone reductase with cultured murine hepatoma cells (Hepa 1c1c7). Spiranoid (29, 32) and 18-functionalized withanolides (2-5, 7-9, 24) were found to be potent inducers of the enzyme, while 5alpha-substituted derivatives exhibited weak activity. Preliminary studies were performed with compound 29 to evaluate enzyme-inducing capacity in multiple organ sites of BALB/c mice. Significant induction was observed in liver and colon, but not in lung, stomach, or mammary gland.

Publication types

  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Animals
  • Brassicaceae / chemistry*
  • Breast / enzymology
  • Carcinoma, Hepatocellular / enzymology*
  • Colon / enzymology
  • Enzyme Induction / drug effects
  • Inhibitory Concentration 50
  • Liver / enzymology
  • Lung / enzymology
  • Mice
  • Mice, Inbred BALB C
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Plants, Medicinal / chemistry*
  • Quinone Reductases / biosynthesis*
  • Solanaceae / chemistry*
  • Stereoisomerism
  • Steroids / chemistry*
  • Steroids / isolation & purification
  • Steroids / pharmacology
  • Stilbenes / pharmacology*
  • Stomach / enzymology
  • Tumor Cells, Cultured / drug effects

Substances

  • Steroids
  • Stilbenes
  • Quinone Reductases