Identification of dehydro-ferulic acid-tyrosine in rye and wheat: Evidence for a covalent cross-link between arabinoxylans and proteins

被引:104
作者
Piber, M [1 ]
Koehler, P [1 ]
机构
[1] Deutsch Forsch Anstalt Lebensmittelchem, D-85748 Garching, Germany
关键词
arabinoxylans; pentosans; ferulic acid; tyrosine; cross-link; bread; wheat; rye;
D O I
10.1021/jf050395b
中图分类号
S [农业科学];
学科分类号
09 ;
摘要
To monitor chemical reactions between ferulate and proteins during breadmaking, 8-C-14-(E)-ferulic acid-(D-galactopyranose-6'-yl)ester was synthesized as a radiotracer and added to wheat and rye flour prior to breadmaking. Breads were lyophilized, extracted by means of a modified Osborne fractionation, and the radioactivity of the fractions was determined by scintillation analysis. The major portion of the radioactivity remained in the water-soluble fraction. However, a significant enrichment of the tracer was also detected in the prolamin and glutelin fractions in comparison to the control experiment. Separation of the prolamin fraction by RP-HPLC and scintillation measurement of the fractions gave evidence for a chemical modification of the tracer. To determine the structure of the reaction product, the prolamin fractions were completely hydrolyzed to free amino acids by means of an enzyme cocktail, and the digests were studied by LC-MS. In one fraction, a newly formed compound was detected. Comparison of its chromatographic and mass spectrometric behavior with a synthetic reference compound gave evidence that the newly identified compound was a dehydroferulic acid-tyrosine cross-link. It is likely that this cross-link represented a covalent linkage between arabinoxylans and cereal proteins. The newly identified cross-link was also identified in wheat and rye flour doughs, which had been prepared without addition of the ferulate tracer. The relative concentration of the dehydroferulic acid-tyrosine cross-link increased during wheat dough preparation.
引用
收藏
页码:5276 / 5284
页数:9
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