Diterpenes from the roots of Euphorbia kansui and their in vitro effects on the cell division of Xenopus

J Nat Prod. 2002 Sep;65(9):1246-51. doi: 10.1021/np0200921.

Abstract

Twelve polycyclic diterpenes have been isolated from the roots of Euphorbia kansui. Nine were assigned with an ingenol skeleton, 20-O-(2'E,4'E-decadienoyl)ingenol (1), 20-O-(2'E,4'Z-decadienoyl)ingenol (2), 3-O-(2'E,4'Z-decadienoyl)ingenol (3), 3-O-(2'E,4'E-decadienoyl)ingenol (4), 3-O-(2'E,4'Z-decadienoyl)-5-O-acetylingenol (5), 3-O-(2'E,4'Z-decadienoyl)-20-O-acetylingenol (6), 3-O-(2'E,4'E-decadienoyl)-20-O-acetylingenol (7), 20-O-(decanoyl)ingenol (8), and 5-O-(2'E,4'E-decadienoyl)ingenol (9), and three with a jatrophane skeleton, kansuinins A (12), B (11), and C (10). Compounds 1, 2, 5, 9, and 12 are new compounds, while 4 and 7 were assigned with new geometric configurations. Their structures were elucidated by spectroscopic and chemical analysis. In vitro treatment of cultured individual Xenopus cells at the blastular stage with 1-9 arrested cleavage significantly (0.5 microg/mL of each compound resulted in >75% cleavage arrest). Of the three jatrophane diterpenes (10-12), only kansuinin B (11) showed any activity, resulting in 87% cleavage arrest at 50 microg/mL.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Cell Division / drug effects
  • Cells, Cultured / drug effects
  • Chromatography, High Pressure Liquid
  • Diterpenes / chemistry
  • Diterpenes / isolation & purification*
  • Diterpenes / pharmacology
  • Euphorbia / chemistry*
  • In Vitro Techniques
  • Medicine, Chinese Traditional
  • Molecular Conformation
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Plant Roots / chemistry
  • Plants, Medicinal / chemistry*
  • Receptors, Fc / biosynthesis*
  • Stereoisomerism
  • Up-Regulation
  • Xenopus / embryology
  • Xenopus / growth & development

Substances

  • Diterpenes
  • Receptors, Fc