Anti-browning and antibacterial dual functions of novel hydroxypyranone-thiosemicarbazone derivatives as shrimp preservative agents: Synthesis, bio-evaluation, mechanism, and application.

To develop new shrimp preservative agents with dual functions of anti-browning and antibacterial, thirteen hydroxypyranone-thiosemicarbazone derivatives were prepared according to molecular hybridization. Thereinto, compound 7j (IC50 = 1.99 ± 0.19 μM) shown the strongest anti-tyrosinase activity and was about twenty-three folds stronger than kojic acid (45.73 ± 4.03 μM). The anti-tyrosinase mechanism of 7j was illustrated through enzyme kinetic, copper ion chelating ability, fluorescence quenching, ultraviolet spectrum, AFM analysis, and molecular docking study. On the other hand, antibacterial assay and time-kill kinetics analysis confirmed that 7j also had good antibacterial activity against V. parahaemolyticus (MIC = 0.13 mM). PI uptake test, SDS-PAGE, and fluorescence spectrometry analysis proved that 7j can affect the bacterial cell membrane. Finally, the shrimp preservation and safety study indicated that 7j has dual effects of inhibiting bacterial growth and preventing enzyme browning, and can be applied to the preservation of fresh shrimp.