Taraxasterane-type triterpene and neolignans from Geum japonicum Thunb. var. chinense F. Bolle

Planta Med. 2011 Dec;77(18):2061-5. doi: 10.1055/s-0031-1280091. Epub 2011 Jul 28.

Abstract

The phytochemical investigation of the ethanolic extract of the whole plants of Geum japonicum Thunb. var. chinense F. Bolle yielded four new compounds: 20 β,28-epoxy-28-hydroxytaraxasteran-3 β-ol (1), (7R,8R)-4-hydroxy-9'-O-(α-L-rhamnopyranosyl)-3,3',5'-trimethoxy-8-O-4'-neolignan (2), (7R,8S)-4-hydroxy-9'-O-(α-L-rhamnopyranosyl)-3,3',5'-trimethoxy-8-O-4'-neolignan (3), and (7S,8S)-5-methoxycupressoside A (4), as well as 40 other known compounds. Structures were elucidated by physical, chemical, and spectroscopic methods, including 1D and 2D NMR, HRESIMS, and CD experiments. The taraxasterane-type triterpene (1) and lignans (2- 6) are reported for the first time from the GEUM genus. Moreover, all compounds were evaluated for anti-inflammatory activities against NO production in RAW264.7 macrophages, and only moderate activities were detected.

Publication types

  • Letter
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acids / chemistry
  • Animals
  • Anti-Inflammatory Agents / chemistry
  • Anti-Inflammatory Agents / isolation & purification
  • Anti-Inflammatory Agents / pharmacology
  • Cell Line
  • Circular Dichroism
  • Ethanol / chemistry
  • Geum / chemistry*
  • Hydrolysis
  • Lignans / chemistry
  • Lignans / isolation & purification*
  • Lignans / pharmacology
  • Lipopolysaccharides / adverse effects
  • Macrophages / drug effects
  • Magnetic Resonance Spectroscopy
  • Mice
  • Molecular Structure
  • Nitric Oxide / chemistry
  • Triterpenes / chemistry
  • Triterpenes / isolation & purification*
  • Triterpenes / pharmacology

Substances

  • Acids
  • Anti-Inflammatory Agents
  • Lignans
  • Lipopolysaccharides
  • Triterpenes
  • Nitric Oxide
  • Ethanol