Triterpene glycosides from red ginseng marc and their anti-inflammatory activities

Bioorg Med Chem Lett. 2014 Sep 1;24(17):4203-8. doi: 10.1016/j.bmcl.2014.07.042. Epub 2014 Jul 22.

Abstract

Three new triterpene glycosides ursan-3β,19α,22β-triol-3-O-β-D-glucopyranosyl (2'→1″)-β-D-glucopyranoside (1), ursan-3α,11β-diol-3-O-α-D-glucopyranosyl-(6'→1″)-α-D-glucopyranosyl-(6″→1‴)-α-D-glucopyranosyl-(6‴→1‴')-α-D-glucopyranoside (2) and lanost-5,24-dien-3β-ol-3-O-β-D-glucopyranosyl-(6'→1″)-β-D-glucopyranosyl-(6″→1‴)-β-D-glucopyranoside (3), together with one known compound were isolated and identified from the marc of red ginseng. Their structures were elucidated by spectroscopic data analysis. Compounds (1-3) were investigated for anti-inflammatory effects using the RAW 264.7 macrophage cell line. In the cell proliferation assay, lipopolysaccharide stimulation decreased cell proliferation of RAW 264.7 macrophage cells, but the suppression of cell proliferation was significantly protected by treatment with compounds 2 and 3. Compounds 2 and 3 had a suppressive effect on the production of nitric oxide (NO), and they inhibited mRNA expression of proinflammatory mediators such as inducible nitric oxide synthase, and cyclooxygenase-2, and proinflammatory cytokines such as two interleukins and tumor necrosis factor-α. These findings suggest that compounds 2 and 3 have potential anti-inflammatory activities.

Keywords: Antiinflammatory activity; Araliaceae; Panax ginseng; Triterpene glycosides.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anti-Inflammatory Agents / chemistry
  • Anti-Inflammatory Agents / isolation & purification
  • Anti-Inflammatory Agents / pharmacology*
  • Cell Survival / drug effects
  • Cyclooxygenase 2 / metabolism
  • Cytokines / antagonists & inhibitors
  • Cytokines / immunology
  • Cytokines / metabolism
  • Dose-Response Relationship, Drug
  • Glycosides / chemistry
  • Glycosides / isolation & purification
  • Glycosides / pharmacology*
  • Lipopolysaccharides / antagonists & inhibitors
  • Lipopolysaccharides / pharmacology
  • Macrophages / drug effects*
  • Macrophages / immunology
  • Macrophages / metabolism
  • Mice
  • Molecular Conformation
  • Nitric Oxide / antagonists & inhibitors
  • Nitric Oxide / biosynthesis
  • Nitric Oxide Synthase Type II / antagonists & inhibitors
  • Nitric Oxide Synthase Type II / metabolism
  • Panax / chemistry*
  • Structure-Activity Relationship
  • Triterpenes / chemistry
  • Triterpenes / isolation & purification
  • Triterpenes / pharmacology*

Substances

  • Anti-Inflammatory Agents
  • Cytokines
  • Glycosides
  • Lipopolysaccharides
  • Triterpenes
  • Nitric Oxide
  • Nitric Oxide Synthase Type II
  • Cyclooxygenase 2