Diastereomeric stilbene glucoside dimers from the bark of Norway spruce (Picea abies)

Phytochemistry. 2008 Feb;69(3):772-82. doi: 10.1016/j.phytochem.2007.08.033. Epub 2007 Oct 29.

Abstract

As part of a long-term study of the chemical defenses of Norway spruce (Picea abies) against herbivores and pathogens, a phytochemical survey of the phenolics in the bark was carried out. Eight stilbene glucoside dimers, designated as piceasides A-H (1a-4b), were isolated as four 1:1 mixtures of inseparable diastereomers. Their structures were determined by extensive spectroscopic means including 1D (1H and 13C) and 2D NMR (1H-1H COSY, HSQC, HMBC, ROESY) spectra, and were supported by enzymatic hydrolysis and computational analysis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cellulase / chemistry
  • Computer Simulation
  • Dimerization
  • Glucosides / chemistry*
  • Glucosides / isolation & purification
  • Hydrolysis
  • Magnetic Resonance Spectroscopy / methods
  • Magnetic Resonance Spectroscopy / standards
  • Molecular Conformation
  • Norway
  • Picea / chemistry*
  • Plant Bark
  • Reference Standards
  • Stereoisomerism
  • Stilbenes / chemistry*
  • Stilbenes / isolation & purification

Substances

  • Glucosides
  • Stilbenes
  • Cellulase