Structure determination of a novel 3(6H)-pyranone chromophore and clarification of its formation from carbohydrates and primary amino acids

被引:8
作者
Frank, O [1 ]
Heuberger, S [1 ]
Hofmann, T [1 ]
机构
[1] Deutsch Forsch Anstalt Lebensmittelchem, D-85748 Garching, Germany
关键词
nonenzymatic browning; Maillard reaction; stable isotope labeling; color precursor; 3-deoxyosone;
D O I
10.1021/jf000199z
中图分类号
S [农业科学];
学科分类号
09 ;
摘要
An intensely orange compound, which has recently been evaluated as one of the main colored compounds formed in Maillard reactions of hexoses, could be unequivocally identified as (Z)-2-[(2-furyl)methylidene] -5,6-di(2-furyl)-6H-pyran-3-one (1) by application of several NMR and LC-MS experiments. To clarify its formation, the effectiveness of certain carbohydrate degradation products as precursors of 1 was studied in a quantitative experiment demonstrating hydroxy-2-propanone, furan-2-aldehyde, and 3-deoxy-2-hexosulose as precursors of the colorant. Site-specific labeling experiments with D-1-[C-13]glucose and D-6-[C-13]glucose, respectively, were performed to elucidate the formation pathway of 1 involving a cleavage of the hexose skeleton between carbon atoms C(5) and C(6). In addition, pentoses could be shown to generate 1 via a similar formation pathway involving the 3-deoxy-2-pentosulose.
引用
收藏
页码:1595 / 1600
页数:6
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