Structure elucidation and NMR spectral assignments of three new lignan glycosides from Akebia trifoliata

Magn Reson Chem. 2008 Feb;46(2):186-90. doi: 10.1002/mrc.2152.

Abstract

Three new lignan glycosides (1-3) were isolated from the stems of Akebia trifoliata. Their structures were elucidated as (7R,8R,7'R,8'R)3,3',5,5'tetramethoxy-4,4'dihydroxy-7,9':7',9-diepoxylignan-4-O-beta-D-glucopyranoside (1), (7S,8S,8'R)-4,4',9-trihydroxy-3,3',5,5'-tetramethoxy-7,9'-epoxylignan-7'-one 9-O-beta-D-glucopyranoside (2), (7R,8R,8'S)-4,4',9-trihydroxy3,3',5,5'-tetramethoxy-7,9'-epoxylignan-7'-one 9-O-beta-D-glucopyranoside (3) by spectral analyses, primarily NMR, MS and CD. The NMR assignments for the compounds were carried out using 1H, 13C, DEPT, COSY, HSQC, HMBC and ROESY NMR experiments.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Drugs, Chinese Herbal / chemistry*
  • Drugs, Chinese Herbal / isolation & purification
  • Glucosides / chemical synthesis*
  • Glucosides / chemistry*
  • Glucosides / isolation & purification
  • Glycosides / chemistry*
  • Glycosides / isolation & purification
  • Lignans / chemical synthesis
  • Lignans / chemistry*
  • Lignans / isolation & purification
  • Models, Molecular
  • Molecular Conformation
  • Nuclear Magnetic Resonance, Biomolecular*
  • Plant Stems / chemistry
  • Ranunculaceae / chemistry*

Substances

  • 3,3',5,5'-tetramethoxy-4,4'-dihydroxy-7,9'-7',9-diepoxylignan-4-O-glucopyranoside
  • 4,4',9-trihydroxy-3,3',5,5'-tetramethoxy-4,4'-dihydroxy-7,9'-epoxylignan-7'-one 9-O-glucopyranoside
  • Drugs, Chinese Herbal
  • Glucosides
  • Glycosides
  • Lignans