Chemistry and biological activity of triterpenoid glycosides from Medicago sativa

Adv Exp Med Biol. 1996:405:171-82. doi: 10.1007/978-1-4613-0413-5_14.

Abstract

Ten triterpenoid glycosides have been isolated from the roots of Medicago sativa L. (Leguminosae) including eight new glycosides and two previously known, medicagenic acid 3-O-beta-D-glucopyranoside and hederagenin 3-O-[beta-D-glucopyranosyl(1-->2)-alpha-L-arabinopyranoside]. Four new saponins were identified as glycosides of medicagenic acid, four from hederagenin. Their structures were elucidated by a combination of chemical and spectroscopic techniques (IR, EI/MS, NMR 1H and 13C). In some cases we used fast atom bombardment mass spectra (FAB/MS), NMR 1H difference spectra (homonuclear double resonance, Overhauser effect), NMR 13C partially decoupled spectra (off resonance), and two-dimensional 1H-1H correlating spectra (COSY 1H-1H). The inhibitory effects of these glycosides on growth and seed germinations and on some phytopathogenic bacteria have also been tested.

Publication types

  • Review

MeSH terms

  • Bacteria / drug effects
  • Fungi / drug effects
  • Medicago sativa / chemistry*
  • Molecular Structure
  • Oleanolic Acid / analogs & derivatives
  • Oleanolic Acid / chemistry
  • Oleanolic Acid / pharmacology
  • Plant Development
  • Plants / drug effects
  • Saponins / chemistry*
  • Saponins / pharmacology*
  • Triterpenes / chemistry*
  • Triterpenes / pharmacology*

Substances

  • Saponins
  • Triterpenes
  • Oleanolic Acid
  • medicagenic acid
  • hederagenin