A Debittered Complex of Glucose-Phenylalanine Amadori Rearrangement Products with β-Cyclodextrin: Structure, Molecular Docking and Thermal Degradation Kinetic Study

Abstract

Non-volatile flavor precursors could be used to overcome the flavor loss problems of volatile flavor enhancers during long-term storage. Glu- and Phe-derived Amadori rearrangement products (ARPs) produce pleasant aroma tones thermally but are bitter. We used β-cyclodextrin (β-CD) for debittering Glu-Phe ARPs. ITC analysis indicated that CD-ARP complexes with 1:1 stoichiometry were obtained. NMR analysis indicated that the aromatic ring of Glu-Phe ARPs was embedded in the β-CD cavity. Molecular docking simulations of the bitter taste receptor hT2R1 showed that CD-ARP complex was inactive compared to Glu-Phe ARPs. Complexation with β-CD resulted in the thermal stabilization of Glu-Phe ARPs and a decrease in the degradation rate constant. Compared to Glu-Phe ARPs, the CD-ARP complex in the thermally treated food system slowed down the formation of browning compounds but didn’t inhibit flavor compound formation. The CD-ARP complex is a promising flavor enhancer for applications in flavored and heated foods.