Formation of discrete molecular size domains of melanoidins depending on the involvement of several α-dicarbonyl compounds:: Part 2

被引:27
作者
Fiedler, Thorsten [1 ]
Kroh, Lothar W. [1 ]
机构
[1] Tech Univ Berlin, Inst Food Technol & Food Chem, Dept Food Anal, D-13355 Berlin, Germany
关键词
Maillard reaction; melanoidins; size exclusion chromatography; 3-deoxyhexosulose; methylglyoxal; D-glucosone;
D O I
10.1007/s00217-006-0442-6
中图分类号
TS2 [食品工业];
学科分类号
0832 ;
摘要
The correlation of several alpha-dicarbonyl compounds with the melanoidin formation and their molecular size distribution was investigated. The results point out that alpha-dicarbonyl compounds, which were formed during the Maillard reaction, are not only the most important intermediates but also the direct precursors for carbohydrate-based melanoidins. Discrete molecular size domains are detected by size exclusion chromatography (SEC-DAD/ RI), which were formed depending on the involvement of several alpha-dicarbonyls by thermal treatment of sucrose Maillard reaction solutions. By investigating sucrose Maillard reaction solutions spiked with methylglyoxal and 3-deoxyhexosulose carried on with direct melanoidin formation in aqueous solutions with alpha-dicarbonyls, molecular size domains of melanoidins could be connected for the first time with the reaction of several involved alpha-dicarbonyl compounds. High molecular size domains formed on the basis of methylglyoxal, whereas 3-deoxyhexosulose and D-glucosone promote lower molecular size domains. Concerning colour measurement methylglyoxal shows the highest browning activity followed by 3-deoxyhexosulose and D-glucosone. The reactivity of alpha-dicarbonyls and a correlated colour formation increase with rising alkaline pH-value. At a pH 5 the degradation and colour formation of alpha-dicarbonyl compounds is suppressed. The results provide new knowledge about colour formation in sucrose solutions.
引用
收藏
页码:473 / 481
页数:9
相关论文
共 15 条
[1]   Intact carbohydrate structures as part of the melanoidin skeleton [J].
Cämmerer, B ;
Jalyschko, W ;
Kroh, LW .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2002, 50 (07) :2083-2087
[2]   Nonenzymatic browning reactions of retro-aldol degradation products of carbohydrates [J].
Cammerer, B ;
Wedzicha, BL ;
Kroh, LW .
EUROPEAN FOOD RESEARCH AND TECHNOLOGY, 1999, 209 (3-4) :261-265
[3]  
FIEDLER T, 2005, EUR FOOD RES TECHNOL
[4]  
HEYNS K, 1970, LIEBIGS ANN CHEM, V733, P159
[5]   4-alkylidene-2-imino-5-[4-alkylidene-5-oxo-1,3-imidazol-2-inyl]azamethylidene-1,3-imidazolidine - A novel colored substructure in melanoidins formed by Maillard reactions of bound arginine with glyoxal and furan-2-carboxaldehyde [J].
Hofmann, T .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1998, 46 (10) :3896-3901
[6]   Degradation of oligosaccharides in nonenzymatic browning by formation of α-dicarbonyl compounds via a "peeling off" mechanism [J].
Hollnagel, A ;
Kroh, LW .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2000, 48 (12) :6219-6226
[7]  
KATO H, 1981, PROG FOOD NUTR SCI, V5, P147
[8]  
KHADEM HE, 1970, CARBOHYD RES, V13, P317
[9]  
Ledl F., 1990, Angew. Chem., V102, P597
[10]   Kinetics of the glucose/glycine Maillard reaction pathways: influences of pH and reactant initial concentrations [J].
Martins, SIFS ;
Van Boekel, MAJS .
FOOD CHEMISTRY, 2005, 92 (03) :437-448