Detection of α-Dicarbonyl Compounds in Maillard Reaction Systems and in Vivo

Abstract

alpha-Dicarbonyl compounds are of major interest in food chemistry and biochemistry as important precursors of, for example, protein modifications and flavor. Due to their high reactivity most of the published structures were identified and quantitated as stable derivatives after reaction with trapping reagents. However, the present study showed for the first time that the trapping reagents are of dramatic impact on the final qualitative and quantitative alpha-dicarbonyl spectrum. As important representatives, aminoguanidine and o-phenylenediamine were used to compare trapping characteristics and to monitor the dicarbonyl structures arising from the degradation of an Amadori compound. Dicarbonyl structures with a reductone moiety could not be or were only insufficiently detected by slow-reacting reagents such as aminoguanidine. On the other hand, fast-reacting chemicals such as o-phenylenediamine imposed high oxidative stress on the investigated system and led to enhanced or false positive formation of dicarbonyl compounds generated by oxidative pathways.

Oral Glycotoxins Determine the Effects of Calorie Restriction on Oxidant Stress, Age-Related Diseases, and Lifespan

“…These data, although not proving a causal relationship, provide the first indication that oxidant homeostasis in mice may depend on the maintenance of a positive balance between AGER1 and RAGE/OS. AGE levels in vivo correlate with AGEs in foods 19,21,37 and with the cellular effects elicited by synthetic MG and CML. 17,23,37,45 This study validates these correlations by showing that specific AGEs in the food contribute directly to serum AGEs and to AGE-induced in vivo responses.…”

“…AGE levels in vivo correlate with AGEs in foods 19,21,37 and with the cellular effects elicited by synthetic MG and CML. 17,23,37,45 This study validates these correlations by showing that specific AGEs in the food contribute directly to serum AGEs and to AGE-induced in vivo responses. It also demonstrates the importance of AGEs contained in the diet, although other oxidants may also contribute to the findings of the current study.…”

Extending the Spectrum of α-Dicarbonyl Compounds in Vivo

“…for GO from 220 to 1150 pmol/ml, for MGO from 120 to 650 pmol/ml, and for DHA from 550 to 6800 pmol/ml (mean values)). Glomb and Tschirnich compared common derivatization approaches (36). According to them, the use of aromatic o-diamines (e.g.…”

Vitamin C Degradation Products and Pathways in the Human Lens

“…OPD). Although there is always a possibility of enhanced formation or false positive formation of dicarbonyls during incubation (26), special care was taken during incubation conditions. All incubations were done in a relatively short time and under slightly acid conditions to prevent hydrolysis of DHA (1) into 2,3-DKG (2) and overestimation of 3-deoxythreosone (3).…”