Preparative isolation of swainsonine from locoweed: extraction and purification procedures

Phytochem Anal. 2003 Jul-Aug;14(4):259-66. doi: 10.1002/pca.713.

Abstract

The trihydroxy indolizidine alkaloid swainsonine, a plant toxin with potent alpha-mannosidase-inhibitory activity and chemotherapeutic potential, was isolated in gram quantities from locoweed (Astragalus lentiginosus). The key isolation and purification step was a continuous liquid/liquid extraction procedure using dichloromethane to extract a basified aqueous methanol solution obtained after isolation of the polar base fraction by ion-exchange. The concentration of swainsonine was increased from ca. 7% in the polar base material to 68% using the liquid/liquid extraction procedure. Pure swainsonine was then obtained by recrystallisation from ammonia-saturated chloroform or by sublimation. Small samples of swainsonine were also purified by formation of the chloroform-soluble methylboronate derivative, from which the alkaloid could be regenerated easily by hydrolysis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / analysis
  • Astragalus Plant / chemistry*
  • Gas Chromatography-Mass Spectrometry
  • Indolizines / analysis
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Plant Extracts / chemistry
  • Plant Extracts / isolation & purification
  • Spectrum Analysis
  • Swainsonine / analysis*
  • Swainsonine / isolation & purification

Substances

  • Alkaloids
  • Indolizines
  • Plant Extracts
  • 2-epilentiginosine
  • Swainsonine