Vacuum Dehydration: An Excellent Method to Promote the Formation of Amadori Compounds (ACs, <i>N</i>-(1-Deoxy-<scp>d</scp>-fructos-1-yl)-amino Acid) in Aqueous Models and Tomato Sauce

The structure of the prepared Amadori rearrangement product of xylose−glycylglycine (XGG-ARP) and a crosslinking product (XGG-CP) was first characterized by liquid chromatography−mass spectrometry (LC−MS)/MS and NMR analysis, respectively. The dependences were then studied for the formation of XGG-ARP and XGG-CP in an aqueous Maillard reaction of a xylose−glycylglycine model system. The influence factors were the reaction temperature, pH, molar ratio of reactants, and the reaction time. It was found that XGG-ARP would acquire the highest yield of 73.8% when the thermal reaction was carried out at 70 °C and pH 8.0 for 10 min. A higher temperature and a lower pH might enhance the yield of the formation of XGG-CP. Combining the low-temperature dehydration reaction with the high-temperature aqueous-phase Maillard reaction increased the XGG-CP yield to 43.54%. The efficient and selective preparation of XGG-ARP and XGG-CP was controllable through the adjustment of reaction conditions. Moreover, the pathway of XGG-CP formation from XGG-ARP and Gly-Gly by the aldimine condensation reaction was also proposed. The high stability of an XGG-CP molecule enhanced by its p−π−p conjugated structure inhibited the occurrence of the Amadori rearrangement and led to a non-keto structure, blocking the further Maillard reaction of XGG-CP.

Section: Resultssupporting

confidence: 93%

Section: Resultsmentioning

confidence: 93%

Dependence and Conversion Mechanism for Selective Preparation of a Xylose–Diglycine Amadori Compound and a Cross-linking Product in an Aqueous Maillard Reaction

Cui

Wang

Hayat

et al. 2021

“…Subsequently, the MG-ARP was eluted with 0.2 mol/L ammonium hydroxide, and the eluent was collected. The fractions of the MG-ARP were freeze-dried to light-yellow powders which were subsequently detected by UPLC-Q-TOF/MS of 96% purity according to Zhou et al…”

Section: Methodsmentioning

confidence: 99%

Effect of Methionine on the Thermal Degradation of N-(1-Deoxy-d-fructos-1-yl)-methionine Affecting Browning Formation

Deng

Cui

Hayat

et al. 2021

The effect of additional dl-methionine (Met) on the thermal degradation of a methionine–glucose-derived Amadori rearrangement product (MG-ARP) was investigated under different reaction conditions. The resulting color formation and changes in the concentrations of MG-ARP, Met, and α-dicarbonyl compounds were investigated. Additional Met did not affect the degradation rate of MG-ARP but got involved in subsequent reactions and resulted in a decrease in the contents of C6-α-dicarbonyl compounds. During MG-ARP degradation, the formation of glyoxal (GO) and methylglyoxal (MGO) was facilitated by additional Met, through retro-aldolization reaction of C6-α-dicarbonyl compounds. This effect of Met addition was dependent on the reaction temperature, and the consistent conclusion could be made in a buffer system. The improvement of GO and MGO formation as color precursors caused by the additional Met contributed to the acceleration of browning formation.

“…Based on our previous work, the yield of Fru-His can be increased to 90.73 mol % in the aqueous simulation system by vacuum dehydration; thus, we obtained a sufficiently pure substance for further functional and mechanism analysis. The purpose of the present study is to verify the ACE inhibitory activity and digestive stability of Fru-His and to obtain information about the molecular interactions.…”

Section: Introductionmentioning

confidence: 92%

“…Therefore, in industrial processing, the formation of Fru-His is inevitable through the Maillard reaction. We even used vacuum dehydration to increase the Fru-His content in tomato sauce to 1237.26 mg/kg in a previous study . Unlike many advanced glycation end products (AGEs) that are detrimental, Fru-His’ beneficial physiological activities have been verified several times, such as it was considered to be an excellent antioxidant in tomato powder and its content was positively correlated with many functional activities of foods, including ACE inhibition. , Yu et al investigated the inhibitory activities of eight kinds of ACs against ACE, among which Fru-His was one of the most effective ones.…”

Section: Introductionmentioning

confidence: 99%

Angiotensin-Converting Enzyme (ACE) Inhibitory Activity and Mechanism Analysis of N-(1-Deoxy-d-fructos-1-yl)-histidine (Fru-His), a Food-Derived Amadori Compound

Zhou

Yang

Xie³

et al. 2022

Self Cite

N-(1-Deoxy-d-fructos-1-yl)-histidine (Fru-His), one of the Amadori compounds, widely presents in processed foods, and its potential functional activities have attracted extensive attention in recent years. In this work, the angiotensin-converting enzyme (ACE) inhibitory activity and mechanism of Fru-His were investigated. The IC50 value of Fru-His was 0.150 ± 0.019 mM, and there was no obvious degradation of Fru-His after digestion simulation, showing that Fru-His has good ACE inhibition and digestive stability. Fru-His was a competitive inhibitor according to the enzyme inhibition kinetic analysis. The interaction between ACE and Fru-His occurred spontaneously mainly through hydrogen bonding, and the process was accompanied by fluorescence quenching and the alteration of the secondary structure of ACE. The molecular docking data supported the above results. Fru-His was attached to ACE’s S1 active pocket through hydrogen bonds and interacted with zinc ions in active sites. The present study demonstrates that food-derived Fru-His has the potential to relieve hypertension.