Three new oleanene glycosides from Sophora flavescens

Chem Pharm Bull (Tokyo). 1992 Nov;40(11):2990-4. doi: 10.1248/cpb.40.2990.

Abstract

Three new oleanene glycosides, sophoraflavosides II-IV (2-4) were isolated together with sophoraflavoside I (1) as the corresponding methyl ester forms from Sophorae Radix, the fresh roots of Sophora flavescens AITON (Leguminosae). Their structures have been elucidated as oxytrogenin 3-O-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-galactopyranosyl-(1-->2)-beta -D- glucuronopyranoside (2), 3-O-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-galactopyranosyl-(1-->2)-beta -D-glucuronopyranosyl oxytrogenin 22-O-alpha-L-arabinopyranoside (3) and 3-O-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-galactopyranosyl-(1-->2)-beta -D-glucuronopyranosyl oxytrogenin 22-O-beta-D-glucopyranosyl-(1-->2)-alpha-L-arabinopyranoside (4), along with unambiguous characterization as 3 beta,22 beta,24-trihydroxyolean-12-en-29-oic acid for their sapogenol, named oxytrogenin (5) on the bases of chemical reactions and spectral analyses.

MeSH terms

  • Carbohydrate Sequence
  • Chromatography, Gas
  • Glycosides / chemistry
  • Glycosides / isolation & purification*
  • Hydrolysis
  • Magnetic Resonance Spectroscopy
  • Molecular Sequence Data
  • Oleanolic Acid / analogs & derivatives*
  • Oleanolic Acid / chemistry
  • Oleanolic Acid / isolation & purification
  • Plants / chemistry*
  • Structure-Activity Relationship

Substances

  • Glycosides
  • sophoraflavoside II
  • sophoraflavoside III
  • sophoraflavoside IV
  • Oleanolic Acid