Diastereomeric stilbene glucoside dimers from the bark of Norway spruce (Picea abies).
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.
Li
Sheng-Hong
SH
Max Planck Institute for Chemical Ecology, Beutenberg Campus, Hans-Knöll-Strabe 8, D-07745 Jena, Germany.
Niu
Xue-Mei
XM
Zahn
Stefan
S
Gershenzon
Jonathan
J
Weston
Jennie
J
Schneider
Bernd
B
D002480:Cellulase / Q000737:chemistry; D003198:Computer Simulation; D019281:Dimerization; D005960:Glucosides / Q000737:chemistry* / Q000302:isolation & purification; D006868:Hydrolysis; D009682:Magnetic Resonance Spectroscopy / Q000379:methods / Q000592:standards; D008968:Molecular Conformation; D009664:Norway; D028222:Picea / Q000737:chemistry*; D024301:Plant Bark; D012015:Reference Standards; D013237:Stereoisomerism; D013267:Stilbenes / Q000737:chemistry* / Q000302:isolation & purification
D005960:Glucosides; D013267:Stilbenes; D002480:Cellulase