Comparing the effect of benzoic acid and cinnamic acid hydroxyl derivatives on polyphenol oxidase: activity, action mechanism, and molecular docking
文献类型： 外文期刊
第一作者： Sun, Yuefang
作者： Sun, Yuefang;Zhou, Lei;Liao, Tao;Liu, Junping;Yu, Kaibo;Zou, Liqiang;Liu, Wei;Zhou, Wei
作者机构：
关键词： polyphenol oxidase; cinnamic acid; benzoic acid; hydroxyl derivative; interaction; activity inhibition
期刊名称：JOURNAL OF THE SCIENCE OF FOOD AND AGRICULTURE （ 影响因子：4.125； 五年影响因子：4.096 ）
ISSN： 0022-5142
年卷期： 2022 年 102 卷 9 期
页码：
收录情况： SCI
摘要： BACKGROUND Polyphenol oxidase (PPO) is considered to have a key role in the food industry because it initiates enzymatic browning in the processing and storage of fruit and vegetables. Increasing numbers of benzoic and cinnamic acid derivatives have been found to be efficient inhibitors of polyphenol oxidase, but a comparison study on activity and action mechanism is lacking. In this study, 18 benzoic acid and cinnamic acid hydroxy derivatives were selected and investigated. RESULTS Three substrates, four activators and 11 inhibitors were identified from benzoic and cinnamic acid derivatives. 2,4-Dihydroxycinnamic acid and benzoic acid showed the strongest inhibitory effect on PPO, with IC50 of 0.092 and1.425 mmol L-1, respectively. Benzoic acid reversibly inhibited PPO in a competitive manner, while 2,4-dihydroxycinnamic acid showed a mixed-type inhibition. Both of them showed that static-type fluorescence quenching and electrostatic interaction were the main driving force in the bonding process. Compared with benzoic acid, 2,4-dihydroxycinnamic acid more easily formed hydrogen bonds in the active site of PPO, making the interaction more stable. CONCLUSION Comparative analysis showed that the inhibition effect of cinnamic acid hydroxyl derivatives on PPO was stronger than that of benzoic acid derivatives. Benzoic acid and 2,4-dihydroxycinnamic acid were the strongest inhibitors. PPO inhibitors identified from benzoic and cinnamic acid derivatives are expected to be promising inhibitors for controlling fruit and vegetable browning. (c) 2021 Society of Chemical Industry.
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