Anti-osteoclastogenic effects of isoquinoline alkaloids from the rhizome extract of Sinomenium acutum

Arch Pharm Res. 2016 May;39(5):713-20. doi: 10.1007/s12272-016-0734-8. Epub 2016 Mar 18.

Abstract

A phytochemical investigation for the rhizome extract from Sinomenium acutum (Menispermaceae) resulted in the isolation of several active principles responsible for the anti-osteoclastogenic property of the extract, together with related isoquinoline alkaloids (1-13) including two new compounds, 1 and 2. Among isolated compounds, salutaridine (7), dauricumine (10), cheilanthifoline (12), and dauriporphine (13) were observed to give significant inhibitions on receptor activator of nuclear factor-κB ligand-induced differentiation of mouse bone marrow-derived macrophages into multinucleated osteoclasts, respectively. The chemical structures of two newly isolated compounds, 1 and 2 were established as 8-demethoxycephatonine (1) and 7(R)-7,8-dihydrosinomenine (2), by spectroscopic analyses including 2D NMR experiments.

Keywords: Anti-osteoclastogenic effect; Isoquinoline alkaloids; Menispermaceae; Sinomenium acutum.

MeSH terms

  • Alkaloids / isolation & purification*
  • Alkaloids / pharmacology
  • Animals
  • Cell Differentiation / drug effects*
  • Cell Differentiation / immunology
  • Cell Survival / drug effects
  • Cells, Cultured
  • Isoquinolines / isolation & purification*
  • Isoquinolines / pharmacology
  • Macrophages / cytology
  • Macrophages / drug effects
  • Macrophages / immunology
  • Male
  • Mice, Inbred ICR
  • Molecular Structure
  • Osteoclasts / cytology
  • Osteoclasts / drug effects*
  • Osteoclasts / immunology
  • Osteogenesis / drug effects*
  • RANK Ligand / antagonists & inhibitors
  • Receptor Activator of Nuclear Factor-kappa B / antagonists & inhibitors
  • Rhizome / chemistry*
  • Sinomenium / chemistry*

Substances

  • Alkaloids
  • Isoquinolines
  • RANK Ligand
  • Receptor Activator of Nuclear Factor-kappa B