6,7-Bis-(2-methoxyethoxy)-4(3H)-quinazolinone as a novel inhibitor of tyrosinase and potential anti-browning agent of fresh-cut apples

6,7-Bis-(2-methoxyethoxy)-4(3H)-quinazolinone (BMEQ) was selected from quinazolinones for its strong tyrosinase inhibitory activity (IC50 = 160 ± 6 μM). It suppressed tyrosinase activity in a competitive way and quenched the fluorescence of the enzyme through a static mechanism. The binding of BMEQ...

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Bibliographic Details
Published in:Journal of bioscience and bioengineering 2024-03, Vol.137 (3), p.165-172
Main Authors: Chai, Wei-Ming, Bai, Qiuhan, Pan, Qiuxia, Wang, Linjun, Zhu, Du
Format: Article
Language:English
Subjects:
Antibrowning agent
antibrowning agents
catechol oxidase
energy transfer
flavonoids
fluorescence
Fruit
hydrogen
hydrophobicity
Inhibitory mechanism
Malus
Molecular dynamics
Monophenol Monooxygenase
oxidation
peroxidase
phenolic compounds
Quinazolinone
Quinazolinones - pharmacology
Tyrosinase
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Summary:6,7-Bis-(2-methoxyethoxy)-4(3H)-quinazolinone (BMEQ) was selected from quinazolinones for its strong tyrosinase inhibitory activity (IC50 = 160 ± 6 μM). It suppressed tyrosinase activity in a competitive way and quenched the fluorescence of the enzyme through a static mechanism. The binding of BMEQ to tyrosinase increased the hydrophobicity of the latter and facilitated non-radiative energy transfer between them. The formation of BMEQ–tyrosinase complex was driven by hydrogen bonds and hydrophobic interactions, and it loosened the basic framework structure of tyrosinase, affecting the conformation of the enzyme, and leading to a decrease in tyrosinase activity. In addition, the BMEQ postponed the oxidation of phenolics and flavonoids by inhibiting polyphenol oxidase (PPO) and peroxidase (POD), which resulted in the inhibition of the browning of fresh-cut apples. This study identified a novel tyrosinase inhibitor BMEQ and verified its potential application for improving the preservation of postharvest fruits. [Display omitted]
ISSN:1389-1723
1347-4421
DOI:10.1016/j.jbiosc.2023.12.006