Unusual secondary metabolites from Astragalus halicacabus LAM

Chem Biodivers. 2013 Jul;10(7):1328-34. doi: 10.1002/cbdv.201200436.

Abstract

From the whole plant of Astragalus halicacabus (Sect. Halicacabus), a new cycloartane-type glycoside, (20R,24S)-3-O-[α-L-arabinopyranosyl-(1→2)-β-D-xylopyranosyl]-20,24-epoxy-16-O-β-D-glucopyranosyl-3β,6α,16β,25-tetrahydroxycycloartane, and a new glycoside, 3-O-[β-D-apiofuranosyl-(1→2)-β-D-glucopyranosyl]maltol were isolated together with seven known cycloartane-type glycosides, i.e., cyclocanthoside D, askendosides D, F, and G, cyclosieversioside G, cyclostipuloside A, elongatoside, and a known maltol glucoside, 3-O-β-D-glucopyranosylmaltol. The structures were elucidated by means of high-resolution mass spectrometry, and extensive 1D- and 2D-NMR spectroscopic analysis. This is the first phytochemical work on A. halicacabus, and a maltol glycoside was encountered for the first time in the Leguminosae family.

Keywords: Astragalus halicacabus; Cycloartanes; Glycosides; Maltol glycosides.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Astragalus Plant / chemistry
  • Astragalus Plant / metabolism*
  • Cyclohexanones / chemistry*
  • Cyclohexanones / isolation & purification
  • Disaccharides / chemistry*
  • Disaccharides / isolation & purification
  • Glycosides / chemistry*
  • Glycosides / isolation & purification
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Molecular Conformation
  • Triterpenes / chemistry

Substances

  • Cyclohexanones
  • Disaccharides
  • Glycosides
  • Triterpenes
  • cycloartane