Maillard Browning Inhibition by Ellagic Acid via Its Adduct Formation with the Amadori Rearrangement Product

Abstract

The Maillard reaction performed under a stepwise increase of temperature was applied for researching the inhibition of Maillard browning caused by ellagic acid. Ellagic acid was found effective for the inhibition of melanoidin formation in the xylose− glycine Maillard reaction but depended on its dosage and the point of time it was added in the reaction system. The lightest color of the Maillard reaction products was observed when ellagic acid was added at the 90th min, which was the point of time when the Amadori rearrangement product (ARP) developed the most. LC-ESI-MS/MS analysis results showed a significant tendency of the ellagic acid hydrolysis product to react with the predominant intermediate ARP to yield an adduct. The adduct stabilized the ARP and delayed its decomposition and inhibited the downstream reactions toward browning. After the ARP was depleted, ellagic acid also showed an effect on scavenging some short-chain dicarbonyls which contributed to the inhibition of Maillard browning.

Temperature-Dependent Catalysis of Glycylglycine on Its Amadori Compound Degradation to Deoxyosone

“…This result could probably be attributed to the tendency of XGG-ARP toward 1,2-enolization at an acidic pH and also the higher reactivity of the reductone structure of 1deoxyosone than that of 3-deoxyosone. 3,21 Figure 2 illustrates the changes in the concentration of 3deoxyxylosone generated during the heat treatment of the XGG-ARP model with or without glycylglycine addition. The results shown in Figure 2 indicated much lower maximum yields of 3-deoxyxylosone derived from the XGG-ARP with additional glycylglycine involvement than that without glycylglycine addition.…”

“…The analytical conditions were similar to those described previously. 20,21 Analysis of Volatile Compounds in Maillard Reaction Products through Gas Chromatography−MS. Gas chromatography (GC)/mass spectrometer (Finnigan Trace GC/MS, Finnigan, CA, USA) was employed to identify the volatile compounds in the XGG-ARP thermal reaction and the thermal reaction of solutions with different ratios of ARP to glycylglycine.…”

“…The 1-deoxyosone, 3-deoxyosone, glyoxal and methylglyoxal derived from ARP during thermal treatment were analyzed through HPLC–diode array detection (DAD). The analytical conditions were similar to those described previously. , …”

Glycine-Xylose Amadori Compound Formation Tracing through Maillard Browning Inhibition by 2-Threityl-thiazolidine-4-carboxylic Acid Formation from Deoxyosone and Exogenous Cysteine

“…To figure out the optimal time point of cysteine addition at the first mild step of the Maillard reaction that led to the lightest browning of the final products of the Maillard reaction performed under the stepwise increase in temperature, the experiment was based on the stepwise increase in temperature for the Maillard reaction referred to the research of Wang . For the first step, a solution of xylose (0.2 mol/L) and glycine (0.1 mol/L) at pH 7.0 was prepared with deionized water, and the samples were transferred to a water bath at 80 °C.…”

“…To figure out the optimal time point of cysteine addition at the first mild step of the Maillard reaction that led to the lightest browning of the final products of the Maillard reaction performed under the stepwise increase in temperature, the experiment was based on the stepwise increase in temperature for the Maillard reaction referred to the research of Wang. 18 For the first step, a solution of xylose (0.2 mol/L) and glycine (0.1 mol/L) at pH 7.0 was prepared with deionized water, and the samples were transferred to a water bath at 80 °C. After the Maillard reaction at 80 °C for the different durations (20,40,50,60,70,80,90,100,120,140, and 160 min), the solution was then cooled immediately in ice water and used for the next step of the reaction and analysis of the content of GX-ARP by UPLC-ESI-MS according to the method described below.…”