Evolution of Complex Maillard Chemical Reactions, Resolved in Time

Abstract

In this study, we monitored the thermal formation of early ribose-glycine Maillard reaction products over time by ion cyclotron resonance mass spectrometry. Here, we considered sugar decomposition (caramelization) apart from compounds that could only be produced in the presence of the amino acid. More than 300 intermediates as a result of the two initial reactants were found after ten hours (100 °C) to participate in the interplay of the Maillard reaction cascade. Despite the large numerical variety the majority of intermediates follow simple and repetitive reaction patterns. Dehydration, carbonyl cleavage, and redox reactions turned out to have a large impact on the diversity the Maillard reaction causes. Although the Amadori breakdown is considered as the main Maillard reaction pathway, other reactive intermediates, often of higher molecular weight than the Amadori rearrangement product, contribute to a large extent to the multitude of intermediates we observed.

Electrochemical triggering of the Chardonnay wine metabolome

“…"Cell on" (1000 mV) samples were characterized by 1120 masses, which were significantly higher in signal intensities when compared to the wine samples prior to electro-oxidation (cell off) (ANOVA test, p-values ≤ 0.01). A large number of sulfur containing compounds (CHOS and CHONS) showed variation of intensity after the electrochemical oxidation and were found in areas corresponding to peptides, amino acids, and Maillard reaction products (Hemmler et al, 2017), suggesting the onset of a diversity of chemical reactions, which may include for instance Strecker degradation or Michael addition of amino acids/peptides to quinones (Bittner, 2006), when polyphenols are consumed ( Supplementary Table 3). In agreement with on-line experiments above (Figure 2), discriminant masses for oxidized samples (cell on in Figure 3B) were characterized by a higher number of sulfur containing compounds (46 CHOS compounds, in green) and nitrogen and sulfur containing compounds (133 CHNOS compounds, in red).…”

Usage of FT-ICR-MS Metabolomics for Characterizing the Chemical Signatures of Barrel-Aged Whisky

“…Van Krevelen diagrams revealed the specific distributions of elemental composition that are present in both distillate but in significantly higher intensity in whisky or in rum (Figure 5E ). The specificity of whisky is characterized in particular by the presence of CHO compounds especially in the fatty acid and high alcohol area whereas rum is characterized by CHO elemental formulas in the carbohydrate area and Maillard reaction area of van Krevelen diagrams (Figure 5E ; Hemmler et al, 2017 ).…”

Reading From the Crystal Ball: The Laws of Moore and Kurzweil Applied to Mass Spectrometry in Food Analysis

“…For an estimation of the most probable metabolites generally to be expected in foods, it is straightforward to exclude, in a first approximation, all xenobiotica. Moreover, from recent studies on non-enzymatic browning during thermal processing of foods, also termed Maillard reaction, it became obvious that this reaction network results to several tens of thousands of additional metabolites that have started from only a few reactive compounds (11)(12)(13)(14). Apart from these, many further reactions of food metabolites like thermolysis, hydrolysis, or the plethora of lipid peroxidation reactions can be assumed to increase the number of metabolites tremendously.…”