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

[Display omitted] •Design and synthesis of gallic acid-benzylidenehydrazine hybrids (5a-5j).•Compounds 5d and 5f possessed anti-tyrosinase, antioxidant and antibacterial activities.•Compounds 5d and 5f exhibited capacity to preserving fresh-cut apples and shrimps.•Compounds 5d and 5f exhibited low cytotoxic activity in a human cell line. 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.