Characterization of three new triterpenoid saponins from Ardisia japonica

J Nat Prod. 1993 Oct;56(10):1669-75. doi: 10.1021/np50100a002.

Abstract

The isolation and characterization of three novel triterpene glycosides 1-3 from the medicinal plant Ardisia japonica (Myrsinaceae) are described. The compounds are characterized by a branched oligosaccharide chain, composed of four sugar units. The oligosaccharide structures were determined by 1H-1H correlation spectroscopy (COSY, HOHAHA, ROESY) and 1H-13C heteronuclear correlation (HETCOR) nmr experiments. The aglycone moieties are the oleane-type triterpenes cyclamiretin A for 1 and the new 13,28-epoxy-30,30-dimethoxyolean-3 beta, 16 alpha-diol and 3 beta, 16 alpha-dihydroxy-13,28-epoxyolean-29-oic acid for 2 and 3, respectively.

MeSH terms

  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Medicine, Chinese Traditional
  • Molecular Conformation
  • Oleanolic Acid* / analogs & derivatives*
  • Optical Rotation
  • Plant Extracts / analysis
  • Plants, Medicinal / chemistry*
  • Saponins / chemistry*
  • Triterpenes / chemistry*

Substances

  • Plant Extracts
  • Saponins
  • Triterpenes
  • cyclamiretin A 3-O-rhamnopyranosyl-1-4-glucopyranosyl-1-2-(glucopyranosyl-1-4)-arabinopyranoside
  • 3-O-(L-rhamnopyranosyl-1-4-glucopyranosyl-1-2-(glucopyranosyl-1-4)-arabinopyranoside)-16-hydroxy-13,28-epoxy-30,30-dimethoxy-oleane
  • 3-O-(rhamnopyranosyl-1-4-glucopyranosyl-1-2-(glucopyranosyl-1-4)-arabinopyranoside)-16-hydroxy-13,28-epoxy-olean-29-oic acid
  • Oleanolic Acid