Anti-tyrosinase, antioxidant and antibacterial activities of gallic acid-benzylidenehydrazine hybrids and their application in preservation of fresh-cut apples and shrimps

Food Chem. 2022 Jun 1:378:132127. doi: 10.1016/j.foodchem.2022.132127. Epub 2022 Jan 10.


A series of gallic acid-benzylidenehydrazine hybrids were synthesized and evaluated for their tyrosinase inhibitory activity. Thereinto, compounds 5d and 5f potently inhibited tyrosinase with IC50 of 15.3 and 3.3 μM, compared to kojic acid (44.4 μM). The inhibition mechanism suggested that 5d and 5f not only chelated with Cu2+, but also reduced Cu2+ to Cu1+ in the tyrosinase active site. Additionally, 5d and 5f exhibited strong DPPH scavenging and antibacterial activities against Vibrio parahaemolyticu and Staphylococcus aureus, which can be attributed to the function of gallic acid and hydrazone moiety. These compounds also exhibited capacity to preserve fresh-cut apples and shrimps. Finally, 5d and 5f exhibited low cytotoxic activity in a human cell line (HEK293). Therefore, these compounds possess anti-tyrosinase, antioxidant, and antibacterial activities, and can be used in the development of novel food preservatives.

Keywords: Anti-tyrosinase; Antibacterial; Antibrowning; Antioxidant; Gallic acid.

MeSH terms

  • Anti-Bacterial Agents / pharmacology
  • Antioxidants / pharmacology
  • Enzyme Inhibitors
  • Gallic Acid / pharmacology
  • HEK293 Cells
  • Humans
  • Malus*
  • Monophenol Monooxygenase*


  • Anti-Bacterial Agents
  • Antioxidants
  • Enzyme Inhibitors
  • Gallic Acid
  • Monophenol Monooxygenase