Isolation and structural determination of triterpenoid glycosides from the aerial parts of alsike clover (Trifolium hybridum L.)

J Agric Food Chem. 2013 Mar 20;61(11):2631-7. doi: 10.1021/jf305541e. Epub 2013 Mar 4.

Abstract

Five azukisapogenol glycosides (1-5) have been isolated from the aerial parts of alsike clover (Trifolium hybridum L.), and their structures were elucidated by combined spectroscopic, spectrometric (1D and 2D NMR; HRESIMS, ESI-MS/MS), and chemical methods. Three of them are new compounds and were identified as 3-O-[-α-L-arabinopyranosyl(1→2)]-β-D-glucuronopyranosyl azukisapogenol (1), 3-O-[-β-D-glucuronopyranosyl(1→2)-β-D-glucuronopyranosyl]-29-O-β-D-glucopyranosyl azukisapogenol (2), and 3-O-[-α-L-arabinopyranosyl(1→2)-β-D-glucuronopyranosyl]-29-O-β-D-glucopyranosyl azukisapogenol (3). The remaining two (4, 5) are known compounds but have not been previously described as saponins constituents of the genus Trifolium . Also, azukisapogenol is reported here as a triterpenoid aglycone for the first time in this genus. Finally, the main chemotaxonomic features that may be recognized as specific of Trifolium species were discussed.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Glycosides / chemistry*
  • Glycosides / isolation & purification
  • Molecular Structure
  • Plant Components, Aerial / chemistry*
  • Plant Extracts / chemistry*
  • Plant Extracts / isolation & purification
  • Trifolium / chemistry*
  • Triterpenes / chemistry*
  • Triterpenes / isolation & purification

Substances

  • Glycosides
  • Plant Extracts
  • Triterpenes