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

Zhiyun Peng; Yufeng Li; Lijun Tan; Lu Chen; Qiandai Shi; Qiao-Hui Zeng; Haiquan Liu; Jing Jing Wang; Yong Zhao

doi:10.1016/j.foodchem.2022.132127

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.

Authors

Zhiyun Peng¹, Yufeng Li¹, Lijun Tan¹, Lu Chen¹, Qiandai Shi¹, Qiao-Hui Zeng², Haiquan Liu³, Jing Jing Wang⁴, Yong Zhao⁵

Affiliations

¹ College of Food Science and Technology, Shanghai Ocean University, Shanghai 201306, China.
² Department of Food Science, Foshan University, Foshan 528000, China.
³ College of Food Science and Technology, Shanghai Ocean University, Shanghai 201306, China; Laboratory of Quality & Safety Risk Assessment for Aquatic Products on Storage and Preservation (Shanghai), Ministry of Agriculture, Shanghai 201306, China; Shanghai Engineering Research Center of Aquatic-Product Processing & Preservation, Shanghai 201306, China.
⁴ College of Food Science and Technology, Shanghai Ocean University, Shanghai 201306, China; Department of Food Science, Foshan University, Foshan 528000, China. Electronic address: w_j2010@126.com.
⁵ College of Food Science and Technology, Shanghai Ocean University, Shanghai 201306, China; Laboratory of Quality & Safety Risk Assessment for Aquatic Products on Storage and Preservation (Shanghai), Ministry of Agriculture, Shanghai 201306, China; Shanghai Engineering Research Center of Aquatic-Product Processing & Preservation, Shanghai 201306, China. Electronic address: yzhao@shou.edu.cn.

PMID: 35033723
DOI: 10.1016/j.foodchem.2022.132127

Abstract

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*

Substances

Anti-Bacterial Agents
Antioxidants
Enzyme Inhibitors
Gallic Acid
Monophenol Monooxygenase