No abstract

Flavonoids (dihydromyricetin, dihydroquercetin, epicatechin, and epigallocatechin) were applied to indicate the critical formation condition of the Amadori rearrangement product (ARP) in Maillard reaction performed under a two-step temperature rising process in the threonine−xylose model system. Threonine-ARP (Thr-ARP) was mixed with dihydromyricetin (DM), dihydroquercetin (DQ), epicatechin (EC), and epigallocatechin (EGC) before the heat treatment; then, the mixture was tested by liquid chromatography−mass spectrometry (LC−MS). The results showed that these flavonoids trapped the ARP and generated adducts. The A-ring of flavonoids (the meta-polyhydroxylated benzene ring) was the functional group to capture the Thr-ARP. The relative contents of the adducts of DM-Thr-ARP, DQ-Thr-ARP, EC-Thr-ARP, and EGC-Thr-ARP were compared with each other, and it was found that the structure of the C-ring of the flavonoids (the carbonyl group on C-4) significantly impeded the formation of adducts with Thr-ARP, while the number of hydroxyl groups on the B-ring had little influence. The formation of adducts delayed the degradation of Thr-ARP, decreased the production of α-dicarbonyl compounds, and suppressed Maillard browning. In this way, the flavonoids might trace the critical formation conditions of ARP during the two-step temperature rising process.

An Amadori rearrangement product (ARP) derived from ribose (Rib) and glutathione (GSH) was prepared and identified as N-(1-deoxy-D-ribulos-1-yl)-glutathione by ultraperformance liquid chromatography−tandem mass spectrometry and NMR. Thermal treatment of the ARP aqueous solution was conducted, and a relatively high temperature was found to accelerate the degradation of the ARP. The concentration of furans formed at 120 °C was more than 6.39 times that at 100 °C, and especially, the high temperature favored the formation of furfural and 4-hydroxy-5-methyl-3(2H)-furanone through deoxyosone dehydration. The promoting role of extra-added GSH or its constituent amino acids was investigated in the volatile formation during thermal processing of the ARP. Both, the added GSH and its constituent amino acids, could timely capture glyoxal (GO) and methylglyoxal (MGO) to facilitate Strecker degradation, which improved pyrazine formation. Compared with glycine and glutamic acid, cysteine was the most effective extra-added amino acid to react with GO and MGO to produce pyrazine and methylpyrazine. More importantly, the cysteine degraded from extra-added GSH effectively accelerated the generation of sulfur-containing volatile compounds through the reaction of cysteine degradation products with furans and shorter-chain α-dicarbonyl compounds.