Wei-Ming Chai , Qiuhan Bai , Qiuxia Pan , Linjun Wang , Du Zhu
{"title":"6,7-Bis-(2-methoxyethoxy)-4(3H)-quinazolinone as a novel inhibitor of tyrosinase and potential anti-browning agent of fresh-cut apples","authors":"Wei-Ming Chai , Qiuhan Bai , Qiuxia Pan , Linjun Wang , Du Zhu","doi":"10.1016/j.jbiosc.2023.12.006","DOIUrl":null,"url":null,"abstract":"<div><p>6,7-Bis-(2-methoxyethoxy)-4(3<em>H</em><span>)-quinazolinone (BMEQ) was selected from quinazolinones for its strong tyrosinase inhibitory activity (</span><em>IC</em><sub><em>50</em></sub><span> = 160 ± 6 μM). It suppressed tyrosinase activity in a competitive way and quenched the fluorescence of the enzyme<span><span> through a static mechanism. The binding of BMEQ to tyrosinase increased the hydrophobicity<span> 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 </span></span>oxidation<span><span> of phenolics and flavonoids<span> by inhibiting polyphenol oxidase (PPO) and </span></span>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.</span></span></span></p></div>","PeriodicalId":15199,"journal":{"name":"Journal of bioscience and bioengineering","volume":null,"pages":null},"PeriodicalIF":2.3000,"publicationDate":"2024-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of bioscience and bioengineering","FirstCategoryId":"5","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S1389172323003699","RegionNum":4,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"BIOTECHNOLOGY & APPLIED MICROBIOLOGY","Score":null,"Total":0}
引用次数: 0
Abstract
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.
期刊介绍:
The Journal of Bioscience and Bioengineering is a research journal publishing original full-length research papers, reviews, and Letters to the Editor. The Journal is devoted to the advancement and dissemination of knowledge concerning fermentation technology, biochemical engineering, food technology and microbiology.