Activity-guided isolation of novel norwithanolides from depreasubtriflora with potential cancer chemopreventive activity

J Org Chem. 2003 Mar 21;68(6):2350-61. doi: 10.1021/jo020542u.

Abstract

Activity-monitored fractionation of a CHCl(3)-soluble extract of Deprea subtriflora using a quinone reductase induction assay led to the purification of subtrifloralactones A-J (1-10), 10 novel C-18 norwithanolides based on a new C(27) skeleton. These compounds were characterized by spectroscopic and chemical studies, and single-crystal X-ray diffraction analysis was used to confirm the structures of 1 and 4. Compounds 1-10 were evaluated for their cancer chemopreventive activity in terms of their ability to induce quinone reductase activity with cultured murine hepatoma cells, and compounds 1 and 6 were found to be highly effective.

Publication types

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

MeSH terms

  • Animals
  • Anticarcinogenic Agents
  • Carcinoma, Hepatocellular
  • Crystallography, X-Ray
  • Drug Screening Assays, Antitumor
  • Lactones / chemistry
  • Lactones / isolation & purification*
  • Lactones / pharmacology
  • Mice
  • Molecular Conformation
  • Molecular Structure
  • NAD(P)H Dehydrogenase (Quinone) / metabolism
  • Nuclear Magnetic Resonance, Biomolecular
  • Peru
  • Plants, Medicinal / chemistry*
  • Solanaceae / chemistry*
  • Tumor Cells, Cultured / drug effects

Substances

  • Anticarcinogenic Agents
  • Lactones
  • NAD(P)H Dehydrogenase (Quinone)