Optimization of xanthatin extraction from Xanthium spinosum L. and its cytotoxic, anti-angiogenesis and antiviral properties

Eur J Med Chem. 2015 Jan 27:90:491-6. doi: 10.1016/j.ejmech.2014.11.060. Epub 2014 Dec 1.

Abstract

The aqueous extraction of the sesquiterpene lactone xanthatin from Xanthium spinosum L. favours the conversion of xanthinin (1) to xanthatin (2) via the loss of acetic acid. The cytotoxic (Hep-G2 and L1210 human cell lines) and antiviral activities of isolated xanthatin are established. This natural compound shows significant cytotoxicity against the Hep-G2 cell line and our experimental results reveal its strong anti-angiogenesis capacity in vitro. The structure of xanthatin is determined by spectroscopic methods and for the first time confirmed by X-ray diffraction.

Keywords: Anti-angiogenesis; Antitumor activity; Antiviral activity; Sesquiterpene lactones; Xanthatin; Xanthium spinosum L.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Angiogenesis Inhibitors / chemistry
  • Angiogenesis Inhibitors / isolation & purification
  • Angiogenesis Inhibitors / pharmacology*
  • Animals
  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / isolation & purification
  • Antineoplastic Agents, Phytogenic / pharmacology*
  • Antiviral Agents / chemistry
  • Antiviral Agents / isolation & purification
  • Antiviral Agents / pharmacology*
  • Cell Proliferation / drug effects
  • Dose-Response Relationship, Drug
  • Drug Screening Assays, Antitumor
  • Furans / chemistry
  • Furans / isolation & purification
  • Furans / pharmacology*
  • Hep G2 Cells
  • Humans
  • Mice
  • Microbial Sensitivity Tests
  • Molecular Conformation
  • Neovascularization, Pathologic / drug therapy*
  • Rats
  • Structure-Activity Relationship
  • Tumor Cells, Cultured
  • Viruses / drug effects*
  • Xanthium / chemistry*

Substances

  • Angiogenesis Inhibitors
  • Antineoplastic Agents, Phytogenic
  • Antiviral Agents
  • Furans
  • xanthatin