Unambiguous assignments for free dimeric proanthocyanidin phenols from 2D NMR

被引:31
作者
DeBruyne, T
Pieters, LAC
Dommisse, RA
Kolodziej, H
Wray, V
Domke, T
Vlietnick, AJ
机构
[1] UNIV ANTWERP,RIJKSUNIV CTR ANTWERP,ORGAN CHEM LAB,B-2020 ANTWERP,BELGIUM
[2] INST PHARMAZEUT BIOL,FACHBEREICH PHARM,D-14195 BERLIN,GERMANY
[3] GESELL BIOTECHNOL FORSCH MBH,D-38124 BRAUNSCHWEIG,GERMANY
关键词
2D NMR; H-1; NMR; C-13; proanthocyanidins; procyanidin dimers; free phenols;
D O I
10.1016/0031-9422(96)00210-5
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Characterization of proanthocyanidin oligomers proceeds commonly through investigation of NMR data of their peracetates or methyl ether acetates, in conjunction with FAB-mass spectrometry and circular dichroism. Since such an approach is unsuitable in bioassay-guided isolations, we applied two-dimensional NMR techniques for the identification of dimeric proanthocyanidins. This afforded not only a powerful probe for distinction between the different procyanidin isomers, but also allowed full assignments, even for both major rotameric forms, whenever present, without the need for derivatisation. Moreover, discrimination between the crucial 6- and 8-protons and carbons was achieved after addition of traces of cadmium nitrate, resulting in the separation of the broad phenolic signals into sharp singlets. As an example of the general strategy followed in the assignment and combination of data of the different spectra available, complete analysis of underivatised procyanidin B3 or catechin-(4 alpha-->8)-catechin is discussed for the first time. Copyright (C) 1996 Published by Elsevier Science Ltd
引用
收藏
页码:265 / 272
页数:8
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