Mechanism of Dihydromyricetin-Induced Reduction of Furfural Derived from the Amadori Compound: Formation of Adducts between Dihydromyricetin and Furfural or Its Precursors

Abstract

Dihydromyricetin (DMY) was employed to reduce the yield of furfural derived from the Amadori rearrangement product of L-threonine and D-xylose (Thr-ARP) by trapping Thr-ARP, 3-deoxyxyosone (3-DX), and furfural to form adducts. The effect of different concentrations of DMY at different pH values and temperatures on the reduction of furfural production was studied, and the results showed that DMY could significantly reduce furfural production at higher pH (pH 5−7) and lower temperature (110 °C). Through the surface electrostatic potential analysis by Gaussian, a significant enhancement of the C 6 nucleophilic ability at higher pH (pH ≥ 5) was observed on DMY with hydrogen-dissociated phenol hydroxyl. The nucleophilic ability of DMY led to its trapping of Thr-ARP, 3-DX, and furfural with the generation of the adducts DMY−Thr-ARP, DMY−3-DX, and DMY−furfural. The formation of the DMY−Thr-ARP adduct slowed the degradation of Thr-ARP, caused the decrease of the 3-DX yield, and thereby inhibited the conversion of 3-DX to furfural. Therefore, DMY−Thr-ARP was purified, and the structure was identified by nuclear magnetic resonance (NMR). The results confirmed that C 6 or C 8 of DMY and carbonyl carbon in Thr-ARP underwent a nucleophilic addition reaction to form the DMY−Thr-ARP adduct. In combination with the analysis results of Gaussian, most of the DMY−Thr-ARP adducts were calculated to be C 6 −DMY−Thr-ARP. Furthermore, the formation of DMY− furfural caused furfural consumption. The formation of the adducts also shunted the pathway of both Thr-ARP and 3-DX conversion to furfural, resulting in a decrease in the level of furfural production.