Ulmosides A and B: flavonoid 6-C-glycosides from Ulmus wallichiana, stimulating osteoblast differentiation assessed by alkaline phosphatase

Bioorg Med Chem Lett. 2009 Aug 15;19(16):4684-7. doi: 10.1016/j.bmcl.2009.06.074. Epub 2009 Jun 25.

Abstract

Chemical investigation of Ulmus wallichiana stem bark resulted in isolation and identification of three new compounds (2S,3S)-(+)-3',4',5,7-tetrahydroxydihydroflavonol-6-C-beta-D-glucopyranoside (1), (2S,3S)-(+)-4',5,7-trihydroxydihydroflavonol-6-C-beta-D-glucopyranoside (3) and 3-C-beta-D-glucopyranoside-2,4,6-trihydroxymethylbenzoate (8), together with five known flavonoid-6-C-glucosides (2, 4-7). Their structures were elucidated using 1D and 2D NMR spectroscopic analysis. The absolute stereochemistry in compounds 1 and 3 were established with the help of CD data analysis and comparison with the literature data analysis. All the isolated compounds (1-8) were assessed for promoting the osteoblast differentiation using primary culture of rat osteoblast as an in vitro system. Compounds 1-3 and 5 significantly increased osteoblast differentiation as assessed by alkaline phosphatase activity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaline Phosphatase / metabolism*
  • Animals
  • Cell Differentiation
  • Flavonoids / chemistry*
  • Flavonoids / isolation & purification
  • Flavonoids / pharmacology
  • Glycosides / chemistry*
  • Glycosides / isolation & purification
  • Glycosides / pharmacology
  • Osteoblasts / drug effects*
  • Plant Bark / chemistry
  • Plant Stems / chemistry
  • Rats
  • Stereoisomerism
  • Ulmus / chemistry*

Substances

  • Flavonoids
  • Glycosides
  • ulmoside A
  • ulmoside B
  • Alkaline Phosphatase