Anti-browning and antibacterial dual functions of novel hydroxypyranone-thiosemicarbazone derivatives as shrimp preservative agents: Synthesis, bio-evaluation, mechanism, and application. (1st September 2023)

• Record Type: Journal Article
• Authors: Peng, Zhiyun; Wang, Guangcheng; Wang, Jing Jing; Zhao, Yong
• Is Part Of: Food chemistry. Volume 419(2023)
• Publication Date: 2023-09-01
• Subjects: Anti-browning -- Antibacterial -- Tyrosinase -- Shrimp; Food -- Analysis -- Periodicals; Food -- Composition -- Periodicals; 664
• DOI: 10.1016/j.foodchem.2023.136106
• Languages: English
• ISSNs: 0308-8146

Abstract

Graphical abstract: Highlights: A novel series of hydroxypyranone-thiosemicarbazone derivatives were prepared. Compound 7j exhibited potent anti-tyrosinase and antibacterial activity. The anti-tyrosinase and antibacterial mechanism of 7j were studied. Compound 7j has a preservation effect on shrimp. Compound 7j showed low toxicity. Abstract: 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.