Feasibility Study of Amadori Rearrangement Products of Glycine, Diglycine, Triglycine, and Glucose as Potential Food Additives for Production, Stability, and Flavor Formation

Abstract

Amadori rearrangement products (ARPs), as intermediates of the Maillard reaction (MR), are potential natural flavor additives but there is a lack of investigation especially in oligopeptide-ARPs. This study for the first time conducted a systematic analysis in comparing ARPs of glycine, diglycine, triglycine, and glucose to corresponding classic MR systems, including production, stability, and flavor analysis. The ARPs were effectively produced by prelyophilization with heating at 70 °C for 60 min and purified to 96% by a two-step purification method. Correlated with the stability order of amino compounds (glycine > diglycine > triglycine), the stability order of ARPs was Gly-ARP > Digly-ARP ≈ Trigly-ARP. In a negative correlation with heating temperature and time, ARPs were less stable than original amino compounds at high temperatures (100, 130, and 160 °C). ARPs exhibited better flavor formation ability in pyrazines and furans than MR systems, with similar flavor compositions but different preferences. Diglycine-and triglycine-ARPs exhibited better flavor formation efficiency than glycine-ARP. Heating temperature and time, initial pH, and carbon chain length were found to be the parameters that affect the stability and flavor formation of ARPs. This study suggested that ARPs, especially peptide-ARPs, have great potential for usage as food flavor additives in the future.

Formation of Volatile Pyrazinones in Amadori Rearrangement Products and Maillard Reaction Systems and the Major Formation Pathways

“…The pyrazinones formed at 180 °C for triglycine-ARP and glycine-ARP were from 0.03 to 0.20 and from 0.00 to 0.08 mg/L, respectively. A possible reason would be that a greater portion of α-dicarbonyls in ARPs were involved in the formation of other flavor compounds such as pyrazines and furans compared to the MR system . Aside from the lower contents, the formation of pyrazinones in ARPs was similar to that in MR systems and obeyed all the aforementioned rules, including the preference for the formation of dimethylpyrazinones at high temperatures.…”

“…Interestingly, Digly-ARP samples did not show any toxicity on HepG2 growth at all three concentrations. These results might be explained by the α-dicarbonyl composition in the ARP samples generated during thermal treatment . By comparison of three ARPs heated at different temperatures at pH 7, Gly-ARP contained the highest yield of α-dicarbonyls, reaching 17.89% at 130 °C and 16.84% at 160 °C.…”

“…It was over two times the amount of α-dicarbonyls generated in Digly-ARP and Trigly-ARP samples under the same temperature. From their profiles, when temperature changed from 130 to 160 °C, a decrease of glucosone and an increase of 3-deoxyglucosone (3-DG), GO, and MGO were measured in all three ARP samples . α-Dicarbonyl compounds have been elucidated to show a negative impact on human health and wellness.…”

“…DMSO was purchased from Pharmco by Greenfield Global (WI, USA). ARPs were prepared in our lab, as mentioned previously …”

“…Amino acid-ARPs were more investigated in the past, but recent research suggests that peptide-ARPs have better flavor generation performance . Diglycine-ARP and triglycine-ARP have better efficacy in pyrazines and furans formation than glycine-ARP.…”