In situ generation of efficient carbonyl trapping agents from amino acids during food processing can be considered a useful approach to control the accumulation of harmful Maillard reaction products in food. Tryptophan is one such amino acid that can be used to generate carbonyl trapping agents. Indole, the main thermal degradation product of tryptophan, is known to react with simple aldehydes through electrophilic aromatic substitution type reactions mainly at carbon positions 2 and 3 in addition to the ring nitrogen. The ability of indole to scavenge three moles of reactive aldehydes per mole of indole such as formaldehyde, methylglyoxal, and phenylacetaldehyde was investigated using model systems containing tryptophan or indole. The model systems were either (a) heated in an aqueous solution in stainless steel reactors at specified time and temperatures and analyzed by qTOF-MS/MS or (b) directly pyrolyzed and analyzed by GC/MS using isotope labeling technique. Unlike the other aldehydes, the initial alcohol formed with phenylacetaldehyde was able to dehydrate and form an stable conjugated system with the indole. In general, indole was able to capture three moles of paraformaldehyde, three moles of methylglyoxal and three moles of phenylacetaldehyde and suppress the formation of 2-amino-1-methyl-6-phenylimidazo­(4,5-b)­pyridine (PhIP) generated in a model system.

Sugar derived reactive 1,2-dicarbonyl intermediates are considered important precursors for the formation of Maillard reaction products. Efficient strategies are needed to modulate their formation in food. Indole a major thermal degradation product of tryptophan, has been shown to scavenge such 1,2-dicarbonyls at high temperatures. In this study, the trapping of methylglyoxal by indole was monitored at various temperatures either by (a) ATR-FTIR spectroscopy or (b) in-solution using qTOF/MS/MS analysis. Information obtained through these studies have indicated that even at room temperature indole can quickly react with methylglyoxal forming an adduct as confirmed by the emergence of a new peak at 1729 cm −1 and by qTOF/MS/MS analysis. On the open surface of the ATR crystal this adduct underwent a fast oxidization into carboxylic acid as evidenced by the disappearance of the band at 1729 cm −1 and the formation of a new band at 1712 cm −1 and its subsequent conversion into a carboxylate band under basic conditions.

No abstract

No abstract