On-line liquid-chromatography-nuclear magnetic resonance spectroscopy-mass spectrometry coupling for the separation and characterization of secoisolariciresinol diglucoside isomers in flaxseed

被引:34
作者
Fritsche, J [1 ]
Angoelal, R [1 ]
Dachtler, M [1 ]
机构
[1] Unilever Res Labs, NL-3133 AT Vlaardingen, Netherlands
关键词
flaxseed; functional food; liquid chromatography-NMR spectroscopy mass spectrometry; nuclear magnetic resonance spectroscopy; secoisolariciresinol diglucoside;
D O I
10.1016/S0021-9673(02)01110-X
中图分类号
Q5 [生物化学];
学科分类号
071010 ; 081704 ;
摘要
Two secoisolariciresinol diglucoside (SDG) diastereomers were extracted from flaxseed and liberated through alkaline hydrolysis. Anion-exchange and reversed-phase chromatography were successfully employed to purify the hydrolyzed flaxseed extract. On-line LC-NMR-MS analyses revealed the structure of the isolated and purified SDG diastereomers, [2R,2'R]-2,3-bis[(4-hydroxy-3-methoxyphenyl)-methyl]-1,4-butanediyl-bis-beta-glucopyranoside the predominant flaxseed lignan and [2R,2'S]-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]-1,4-butanediyl-bis-beta-glucopyranoside, a previously incompletely characterized minor flaxseed lignan. Circular dichroism (CD) analyses confirmed the presence of two distinguished optically active compounds present in the flaxseed extract. (C) 2002 Elsevier Science B.V. All rights reserved.
引用
收藏
页码:195 / 203
页数:9
相关论文
共 30 条
[11]   Occurrence of hormonally active compounds in food: a review [J].
Fritsche, S ;
Steinhart, H .
EUROPEAN FOOD RESEARCH AND TECHNOLOGY, 1999, 209 (3-4) :153-179
[12]   High-performance liquid chromatography on-line coupled to high-field NMR and mass spectrometry for structure elucidation of constituents of Hypericum perforatum L. [J].
Hansen, SH ;
Jensen, AG ;
Cornett, C ;
Bjornsdottir, I ;
Taylor, S ;
Wright, B ;
Wilson, ID .
ANALYTICAL CHEMISTRY, 1999, 71 (22) :5235-5241
[13]  
HARRIS RK, 1993, CEREAL FOOD WORLD, V38, P147
[14]   HPLC method for analysis of secoisolariciresinol diglucoside in flaxseeds [J].
Johnsson, P ;
Kamal-Eldin, A ;
Lundgren, LN ;
Åman, P .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2000, 48 (11) :5216-5219
[15]   Direct coupling of chromatographic separations to NMR spectroscopy [J].
Lindon, JC ;
Nicholson, JK ;
Wilson, ID .
PROGRESS IN NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY, 1996, 29 :1-49
[16]   Application of directly coupled HPLC-NMR-MS to the identification and confirmation of quercetin glycosides and phloretin glycosides in apple peel [J].
Lommen, A ;
Godejohann, M ;
Venema, DP ;
Hollman, PCH ;
Spraul, M .
ANALYTICAL CHEMISTRY, 2000, 72 (08) :1793-1797
[17]   Isolation and characterization of the lignans, isolariciresinol and pinoresinol, in flaxseed meal [J].
Meagher, LP ;
Beecher, GR ;
Flanagan, VP ;
Li, BW .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1999, 47 (08) :3173-3180
[18]   Quantitation of the lignan secoisolariciresinol diglucoside in baked goods containing flax seed or flax meal [J].
Muir, AD ;
Westcott, ND .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2000, 48 (09) :4048-4052
[19]  
Niessen W.M. A., 1992, LIQUID CHROMATOGRAPH
[20]  
OBERMEYER WR, 1995, P SOC EXP BIOL MED, V208, P6, DOI 10.3181/00379727-208-43824