A novel caryophyllene type sesquiterpene lactone from Asparagus falcatus (Linn.); structure elucidation and anti-angiogenic activity on HUVECs

Eur J Med Chem. 2012 Jan;47(1):601-7. doi: 10.1016/j.ejmech.2011.10.037. Epub 2011 Oct 25.

Abstract

In this study the novel caryophyllene type sesquiterpene lactone (aspfalcolide) has been isolated from the leaves of Asparagus falcatus (Linn.) and characterized by IR, 1D NMR, 2D NMR, EI-MS, HR-ESI-MS and X-ray single crystal diffraction analysis. The aspfalcolide crystallizes in the orthorhombic space group P2(1)2(1)2(1) with a = 6.37360(10), b = 7.6890(2), c = 27.3281(6) Å, α = β = γ = 90(°) and Z = 4. One intermolecular O-H⋯O hydrogen bond enforces these natural molecules to form infinite chains through the crystal. Aspfalcolide was screened for its anti-angiogenic activity in human umbilical vein endothelial cells (HUVECs) and the result showed the remarkable inhibitory effect of aspfalcolide on the proliferation (IC(50) 1.82 μM), migration and tube formation of HUVECs.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Angiogenesis Inhibitors / chemistry*
  • Angiogenesis Inhibitors / isolation & purification
  • Angiogenesis Inhibitors / pharmacology*
  • Asparagus Plant / chemistry*
  • Cell Movement / drug effects
  • Cell Proliferation / drug effects
  • Human Umbilical Vein Endothelial Cells / cytology
  • Human Umbilical Vein Endothelial Cells / drug effects*
  • Humans
  • Lactones / chemistry*
  • Lactones / isolation & purification
  • Lactones / pharmacology*
  • Models, Molecular
  • Molecular Conformation
  • Polycyclic Sesquiterpenes
  • Sesquiterpenes / chemistry*
  • Vascular Endothelial Growth Factor A / pharmacology

Substances

  • Angiogenesis Inhibitors
  • Lactones
  • Polycyclic Sesquiterpenes
  • Sesquiterpenes
  • Vascular Endothelial Growth Factor A
  • caryophyllene