Effect of the C-Ring Structure of Flavonoids on the Yield of Adducts Formed by the Linkage of the Active Site at the A-Ring and Amadori Rearrangement Products during the Maillard Intermediate Preparation

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.

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

“…After the reaction, the mixture was transferred into ice water to stop the reaction. The absorbance at 420 nm of the solution, which indicated the occurrence of browning, was measured by a UV–Vis spectrophotometer (UV-1800; Shimadzu Co., Shanghai, China), which represented the browning degree of the final products …”

“…The absorbance at 420 nm of the solution, which indicated the occurrence of browning, was measured by a UV−Vis spectrophotometer (UV-1800; Shimadzu Co., Shanghai, China), which represented the browning degree of the final products. 19 Synthesis of GX-ARP and Purification. GX-ARP was synthesized based on the method of Cui et al 20 A solution of 0.2 mol/L xylose and 0.1 mol/L glycine at pH 7.0 ± 0.1 was prepared with 100 mL of ultrapure water.…”

α‐Dicarbonyl compounds in food products: Comprehensively understanding their occurrence, analysis, and control

“…At the initial stage of the Maillard reaction, Amadori compounds are generated by the Amadori rearrangement, and these compounds undergo enolization to form α‐DCs. The adducts generated when flavonoids trap Amadori rearrangement products have been shown to decrease the production of α‐DCs (Chen, Cui, et al., 2022). Phenolic compounds also act as antioxidants that prevent the oxidation of sugars, proteins, and lipids, which decrease the generation of α‐DCs (Khan et al., 2020).…”

Phenolische Verbindungen in nicht‐enzymatischen Bräunungsreaktionen

“…B. Acrylamid [10], advanced-glycation end-products (AGEs) [11] und heterocyclischen aromatischen Aminen [12], wird generell als hemmend auf die gesamte Maillard-Reaktion interpretiert. [13,14] A n a l y t i k zugrundeliegenden Strukturen sowie deren Bildungsmechanismen sind daher nahezu unbekannt. [15] Dieses Wissen ist jedoch notwendig, um auf Grundlage von Struktur-Wirkungsbeziehungen sowohl ernährungsphysiologische, technofunktionelle als auch toxikologische Eigenschaften ableiten zu können, da besonders phenolhaltige Melanoidine aus Kaffee in der westlichen Ernährung mit einer Aufnahme von etwa zwei Gramm pro Tag eine wichtige Rolle spielen.…”