Constituents of the twigs of Hernandia ovigera that inhibit the transformation of JB6 murine epidermal cells

J Nat Prod. 2002 Jul;65(7):1065-8. doi: 10.1021/np020042w.

Abstract

Activity-guided fractionation of an ethyl acetate extract of the twigs of Hernandia ovigera, using a soft agar assay with JB6 murine epidermal cells, led to the isolation of two new naturally occurring aryltetralin lignans, (7R,8S,7'R,8'R)-(+)-7'-acetyl-5'-methoxypicropodophyllin (1) and (7R,8S,7'R,8'R)-(+)-7'-acetylpicropodophyllin (2), of which 2 was previously identified as a synthetic product, along with eight known compounds, epiyangambin (3), caruilignan C, diasesartemin, (+)-epimagnolin A, N-methylcorydaldine, (-)-5'-methoxyyatein, (+)-syringaresinol dimethyl ether, and (-)-yatein. The structures and stereochemistry of 1 and 2 were determined using spectroscopic methods. Compounds 2 and 3 exhibited significant inhibition of the transformation of murine epidermal JB6 cells, with IC50 values of 0.15 and 0.4 microg/mL, respectively, while the other isolates were regarded as inactive (IC50 >4 microg/mL).

Publication types

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

MeSH terms

  • Animals
  • Anticarcinogenic Agents / chemistry
  • Anticarcinogenic Agents / isolation & purification*
  • Anticarcinogenic Agents / pharmacology
  • Cells, Cultured / drug effects
  • Epidermis / drug effects
  • Indonesia
  • Inhibitory Concentration 50
  • Lignans / chemistry
  • Lignans / isolation & purification*
  • Lignans / pharmacology
  • Mice
  • Molecular Conformation
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Plants, Medicinal / chemistry*
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • 7'-acetyl-5'-methoxypicropodophyllin
  • 7'-acetylpicropodophyllin
  • Anticarcinogenic Agents
  • Lignans