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This work presents a comparative analysis of the tyrosinase inhibitory effects of five citrus flavonoids, namely hesperetin, hesperidin, neohesperidin, naringenin and naringin. Visbile, fluorescence, and fourier transform infrared (FITR) spectroscopies, and molecular dynamic methods were employed to compare the anti-tyrosinase mechanisms of each flavonoid. Hesperetin, neohesperidin, naringenin and naringin exhibited potent inhibitory activities with IC50 values of 0.74 ± 0.05, 2.19 ± 0.03, 7.50 ± 9.82 and 24.94 ± 8.43 μmol/ml, respectively, all of which were higher than that of kojic acid (0.04 ± 0.02 μmol/ml). The enzymatic kinetics results suggested that hesperetin and naringenin were reversible inhibitors on tyrosinase in the mixed-type manner. H-bond and hydrophobic interactions were found to drive the binding of tyrosinase with hesperetin or naringenin, which subsequently changed the FTIR spectroscopy results by decreasing the α-helix ratio and increasing the β-turn, β-sheet and random coil ratio in tyrosinase. Molecular dynamics simulation not only verified some of the experimental results, but also suggested that the binding of hesperetin and naringenin to tyrosinase was spontaneous. The findings of this study indicate that citrus flavonoids are a promising dietary resource for tyrosinase inhibition. PRACTICAL APPLICATIONS: Hesperetin, hesperidin, neohesperidin, naringenin and naringin were typical citrus flavonoids that have anti-obesity, anti-oxidation, anti-inflammation and anti-diabetes activities. Current study suggested that hesperetin and naringenin were effective reversible inhibitors on tyrosinase in the mixed-type manner. Hesperetin and naringenin might serve as nutritional and chemical agents for regulating the tyrosinase activity to control melanin level in vivo., (© 2022 Wiley Periodicals LLC.)

Background: Zein is commonly used to construct food flavonoid delivery systems. This study investigated the effect and mechanism of zein on the digestive stability of five citrus flavonoids, namely hesperetin (HET), hesperidin (HED), neohesperidin (NHD), naringenin (NEN), and naringin (NIN)., Results: Zein enhanced the digestive stability of the five citrus flavonoids, especially that of HET and NEN, during digestion in the stomach and small intestine. Fluorescence spectroscopy results suggested that citrus flavonoids spontaneously quenched the endogenous fluorescence of zein in static quenching mode. The binding of HET, HED and NHD to zein was driven respectively by electrostatic, hydrophobic and electrostatic interaction. However, Van der Waals' force and hydrogen (H)-bond interaction represented the primary driving force for binding NEN, and NIN to zein to form complexes. The binding of the five citrus flavonoids to zein also caused a diverse bathochromic shift in ultraviolet absorbance. Analysis using Fourier-transform infrared and Raman spectroscopy revealed that the binding behavior of the five citrus flavonoids had different effects on changes in the secondary structures, disulfide bonds, and tyrosine exposure of zein. The results were also partially verified by molecular dynamic simulation., Conclusions: Zein enhanced the digestive stability of the five citrus flavonoids via different binding interactions that was due to the difference in molecular structure of citrus flavonoids. © 2022 Society of Chemical Industry., (© 2022 Society of Chemical Industry.)