The evaluation of catechins reducing heterocyclic aromatic amine formation: Structure-activity relationship and mechanism speculation

IF 6.2 2区 农林科学 Q1 FOOD SCIENCE & TECHNOLOGY
Ruiwei Xie , Haolin Zhang , Xiaomei Lv , Qiuyi Lin , Bing-Huei Chen , Yu-Wen Lai , Lei Chen , Hui Teng , Hui Cao
{"title":"The evaluation of catechins reducing heterocyclic aromatic amine formation: Structure-activity relationship and mechanism speculation","authors":"Ruiwei Xie ,&nbsp;Haolin Zhang ,&nbsp;Xiaomei Lv ,&nbsp;Qiuyi Lin ,&nbsp;Bing-Huei Chen ,&nbsp;Yu-Wen Lai ,&nbsp;Lei Chen ,&nbsp;Hui Teng ,&nbsp;Hui Cao","doi":"10.1016/j.crfs.2024.100727","DOIUrl":null,"url":null,"abstract":"<div><p>The favorable inhibitory effect of tea polyphenols on heterocyclic aromatic amines (HAAs) has been confirmed in many past studies. The objective of this study was to investigate the structure-activity relationship of catechins that act as inhibitors of HAA formation in chemical models. Two kinds of quantitative structure-activity relationship models for catechin-inhibiting-HAA were established. We chose two kinds of HAAs including 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) and 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline (MeIQx), and five catechins including epigallocatechin gallate (EGCG), epicatechin gallate (ECG), epigallocatechin (EGC), epicatechin (EC), and catechin (C). The inhibitory effect of five catechins were in the following order: EGCG &gt; ECG &gt; EGC &gt; C &gt; EC. Thereinto, EGCG and ECG showed dramatically better inhibition on the formation of PhIP and MeIQx, especially EGCG. Further, the mechanisms of catechin-inhibiting-HAA were speculated by correlation analysis. The free radical-scavenging ability was predicted to be the most relevant to the inhibitory effect of ECG, EGC, EC and C on HAAs. Differently, the phenylacetaldehyde-trapping ability might be the more important mechanism of EGCG inhibiting PhIP in chemical model system. This study may bring a broader idea for controlling the formation of HAAs according to the structure of catechins.</p></div>","PeriodicalId":10939,"journal":{"name":"Current Research in Food Science","volume":null,"pages":null},"PeriodicalIF":6.2000,"publicationDate":"2024-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.sciencedirect.com/science/article/pii/S2665927124000534/pdfft?md5=4db1cbad1bc43e269e68f565df1141b8&pid=1-s2.0-S2665927124000534-main.pdf","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Current Research in Food Science","FirstCategoryId":"97","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S2665927124000534","RegionNum":2,"RegionCategory":"农林科学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"FOOD SCIENCE & TECHNOLOGY","Score":null,"Total":0}
引用次数: 0

Abstract

The favorable inhibitory effect of tea polyphenols on heterocyclic aromatic amines (HAAs) has been confirmed in many past studies. The objective of this study was to investigate the structure-activity relationship of catechins that act as inhibitors of HAA formation in chemical models. Two kinds of quantitative structure-activity relationship models for catechin-inhibiting-HAA were established. We chose two kinds of HAAs including 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) and 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline (MeIQx), and five catechins including epigallocatechin gallate (EGCG), epicatechin gallate (ECG), epigallocatechin (EGC), epicatechin (EC), and catechin (C). The inhibitory effect of five catechins were in the following order: EGCG > ECG > EGC > C > EC. Thereinto, EGCG and ECG showed dramatically better inhibition on the formation of PhIP and MeIQx, especially EGCG. Further, the mechanisms of catechin-inhibiting-HAA were speculated by correlation analysis. The free radical-scavenging ability was predicted to be the most relevant to the inhibitory effect of ECG, EGC, EC and C on HAAs. Differently, the phenylacetaldehyde-trapping ability might be the more important mechanism of EGCG inhibiting PhIP in chemical model system. This study may bring a broader idea for controlling the formation of HAAs according to the structure of catechins.

Abstract Image

评估儿茶素对杂环芳香胺形成的抑制作用:结构-活性关系和机理推测
茶多酚对杂环芳香胺(HAAs)的良好抑制作用已在过去的许多研究中得到证实。本研究的目的是在化学模型中研究作为 HAA 形成抑制剂的儿茶素的结构-活性关系。我们建立了两种儿茶素抑制 HAA 的定量结构-活性关系模型。我们选择了两种HAAs,包括2-氨基-1-甲基-6-苯基咪唑并[4,5-b]吡啶(PhIP)和2-氨基-3,8-二甲基咪唑并[4,5-f]喹喔啉(MeIQx),以及五种儿茶素,包括表没食子儿茶素没食子酸酯(EGCG)、表儿茶素没食子酸酯(ECG)、表没食子儿茶素(EGC)、表儿茶素(EC)和儿茶素(C)。五种儿茶素的抑制作用依次为EGCG > ECG > EGC > C > EC。其中,EGCG 和 ECG 对 PhIP 和 MeIQx 生成的抑制作用明显更强,尤其是 EGCG。此外,还通过相关分析推测了儿茶素抑制 HAA 的机制。据预测,儿茶素清除自由基的能力与 ECG、EGC、EC 和 C 对 HAAs 的抑制作用最为相关。不同的是,在化学模型系统中,苯乙醛捕获能力可能是 EGCG 抑制 PhIP 的更重要机制。这项研究为根据儿茶素的结构控制 HAAs 的形成提供了更广阔的思路。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
求助全文
约1分钟内获得全文 求助全文
来源期刊
Current Research in Food Science
Current Research in Food Science Agricultural and Biological Sciences-Food Science
CiteScore
7.40
自引率
3.20%
发文量
232
审稿时长
84 days
期刊介绍: Current Research in Food Science is an international peer-reviewed journal dedicated to advancing the breadth of knowledge in the field of food science. It serves as a platform for publishing original research articles and short communications that encompass a wide array of topics, including food chemistry, physics, microbiology, nutrition, nutraceuticals, process and package engineering, materials science, food sustainability, and food security. By covering these diverse areas, the journal aims to provide a comprehensive source of the latest scientific findings and technological advancements that are shaping the future of the food industry. The journal's scope is designed to address the multidisciplinary nature of food science, reflecting its commitment to promoting innovation and ensuring the safety and quality of the food supply.
文献相关原料
公司名称 产品信息 采购帮参考价格
百灵威 L-threonine
¥19.00~¥21546.00
百灵威 creatinine
¥24.00~¥13614.18
百灵威 L-phenylalanine
×
引用
GB/T 7714-2015
复制
MLA
复制
APA
复制
导出至
BibTeX EndNote RefMan NoteFirst NoteExpress
×
提示
您的信息不完整,为了账户安全,请先补充。
现在去补充
×
提示
您因"违规操作"
具体请查看互助需知
我知道了
×
提示
确定
请完成安全验证×
copy
已复制链接
快去分享给好友吧!
我知道了
右上角分享
点击右上角分享
0
联系我们:info@booksci.cn Book学术提供免费学术资源搜索服务,方便国内外学者检索中英文文献。致力于提供最便捷和优质的服务体验。 Copyright © 2023 布克学术 All rights reserved.
京ICP备2023020795号-1
ghs 京公网安备 11010802042870号
Book学术文献互助
Book学术文献互助群
群 号:481959085
Book学术官方微信