Astersedifolioside A-C, three new oleane-type saponins with antiproliferative activity

Bioorg Med Chem. 2004 Sep 15;12(18):4909-15. doi: 10.1016/j.bmc.2004.06.042.

Abstract

A phytochemical analysis of Aster sedifolius has led to the isolation of three novel triterpenoid saponins, based on an oleane-type skeleton and named astersedifolioside A (1), B (2) and C (3). On the basis of chemical, and 2D NMR and mass spectrometry data, the structures of the new compounds were elucidated as 3-O-[alpha-L-rhamnopyranosyl (1-->2)-beta-D-glucopyranosyl] echinocystic acid 28-[O-alpha-L-rhamnopyranosyl (1-->2)-alpha-L-arabinopyranoside] (1), 3-O-[alpha-L-rhamnopyranosyl (1-->2)-beta-D-glucopyranosyl] echinocystic acid 28-[O-beta-D-xylopyranosyl (1-->4)-O-alpha-L-rhamnopyranosyl (1-->2)-alpha-L-arabinopyranoside] (2) and 3-O-[alpha-L-rhamnopyranosyl (1-->2)-beta-D-glucopyranosyl (1-->2)-beta-D-glucopyranosyl] echinocystic acid 28-[O-beta-D-xylopyranosyl (1-->4)-O-alpha-L-rhamnopyranosyl (1-->2)-alpha-L-arabinopyranoside] (3). The isolated compounds showed antiproliferative effect in KiMol, a transformed thyroid cell line.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Asteraceae*
  • Cell Line
  • Growth Inhibitors / chemistry
  • Growth Inhibitors / isolation & purification
  • Growth Inhibitors / pharmacology*
  • Oleanolic Acid / chemistry
  • Oleanolic Acid / isolation & purification
  • Oleanolic Acid / pharmacology*
  • Plant Components, Aerial
  • Plant Extracts / chemistry
  • Plant Extracts / isolation & purification
  • Plant Extracts / pharmacology
  • Rats
  • Saponins / chemistry
  • Saponins / isolation & purification
  • Saponins / pharmacology*

Substances

  • Growth Inhibitors
  • Plant Extracts
  • Saponins
  • Oleanolic Acid