Flavanone glycosides from viscum coloratum and their inhibitory effects on osteoclast formation

Chem Biodivers. 2011 Sep;8(9):1682-8. doi: 10.1002/cbdv.201000289.

Abstract

Two novel flavanone glycosides, homoeriodictyol 7-O-β-D-[6-(3-hydroxybutanoyl)glucopyranoside] (viscumneoside IX; 1) and homoeriodictyol 7-O-β-D-[6-(3-hydroxybutanoyl)glucopyranosyl](1→2)-β-D-glucopyranoside (viscumneoside X; 2), together with four known flavanoids, 2-homoeriodictyol 7-O-β-D-glucopyranoside (3), viscumneoside I (4), viscumneoside III (5), and 4',5-dihydroxy-3'-methoxy-7-(2-O-α-L-rhamnopyranosyl-β-D-glucopyranosyloxy)flavanone (6) were isolated from stems and leaves of Viscum coloratum. Their structures were elucidated on the basis of their NMR spectra, HR-FAB-MS data, and acid hydrolysis. Inhibitory effects of the four compounds 1-4 on the formation of osteoclast-like multinucleated cells were investigated. As a result, all the four flavanoids showed significant inhibitory effects on the formation of osteoclast-like multinuclear cells even at a low concentration of 2 μg/ml. The activities of 1-4 at such a concentration exceeded or approximated to that of elcitonin, the positive control drug at a concentration of 2 U/ml, suggesting that they may be of interest for the development of new anti-osteoporosis drugs.

MeSH terms

  • Animals
  • Cells, Cultured
  • Flavonoids / chemistry*
  • Flavonoids / isolation & purification
  • Flavonoids / pharmacology
  • Glucosides / chemistry*
  • Glucosides / isolation & purification
  • Glucosides / pharmacology
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Mice
  • Molecular Conformation
  • Osteoclasts / cytology
  • Osteoclasts / drug effects*
  • Plant Leaves / chemistry
  • Plant Stems / chemistry
  • Viscum / chemistry*

Substances

  • Flavonoids
  • Glucosides
  • viscumneoside IX
  • viscumneoside X