Anti-inflammatory triterpenoid saponins from the stem bark of Kalopanax pictus

J Nat Prod. 2011 Sep 23;74(9):1908-15. doi: 10.1021/np200382s. Epub 2011 Aug 26.

Abstract

Five new compounds, 16,23,29-trihydroxy-3-oxo-olean-12-en-28-oic acid (1), 4,23,29-trihydroxy-3,4-seco-olean-12-en-3-oate-28-oic acid (2), 3β,6β,23-trihydroxyolean-12-en-28-oic acid 28-O-β-D-glucopyranoside (3), 3-O-[2,3-di-O-acetyl-α-L-arabinopyranosyl]hederagenin 28-O-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-β-D-glucopyranoside (4), and 3-O-[3,4-di-O-acetyl-α-L-arabinopyranosyl]hederagenin 28-O-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-β-D-glucopyranoside (5), as well as 10 known compounds (6-15), were isolated from the stem bark of Kalopanax pictus. Compounds 1-5 and 7-14 inhibited TNFα-induced NF-κB transcriptional activity in HepG2 cells in a dose-dependent manner, with IC50 values ranging from 0.6 to 16.4 μM. Furthermore, the transcriptional inhibitory function of these compounds was confirmed on the basis of decreases in COX-2 and iNOS gene expression in HepG2 cells. The structure-activity relationship of the compounds with respect to anti-inflammatory activity is also discussed.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Inflammatory Agents / chemistry
  • Anti-Inflammatory Agents / isolation & purification*
  • Anti-Inflammatory Agents / pharmacology*
  • Base Sequence
  • Cyclooxygenase 2 Inhibitors / chemistry
  • Cyclooxygenase 2 Inhibitors / isolation & purification
  • Cyclooxygenase 2 Inhibitors / pharmacology
  • Hep G2 Cells
  • Humans
  • Kalopanax / chemistry*
  • Korea
  • Molecular Structure
  • NF-kappa B / drug effects
  • Nitric Oxide Synthase Type II / antagonists & inhibitors
  • Plant Bark / chemistry
  • Saponins / chemistry
  • Saponins / isolation & purification*
  • Saponins / pharmacology*
  • Structure-Activity Relationship
  • Triterpenes / chemistry
  • Triterpenes / isolation & purification*
  • Triterpenes / pharmacology*

Substances

  • Anti-Inflammatory Agents
  • Cyclooxygenase 2 Inhibitors
  • NF-kappa B
  • Saponins
  • Triterpenes
  • Nitric Oxide Synthase Type II