State Key Laboratory of Food Science and Technology, Nanchang University, Nanchang, China.
Key Laboratory of Tropical Crop Products Processing of Ministry of Agriculture and Rural Affairs, Agricultural Products Processing Research Institute of Chinese Academy of Tropical Agricultural Sciences, Haikou, China.
J Sci Food Agric. 2022 Jul;102(9):3771-3780. doi: 10.1002/jsfa.11725. Epub 2022 Jan 4.
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.
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 IC of 0.092 and1.425 mmol L , 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.
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. © 2021 Society of Chemical Industry.
多酚氧化酶(PPO)被认为在食品工业中具有关键作用,因为它在水果和蔬菜的加工和储存过程中引发酶促褐变。越来越多的苯甲酸和肉桂酸衍生物被发现是多酚氧化酶的有效抑制剂,但缺乏对其活性和作用机制的比较研究。在本研究中,选择并研究了 18 种苯甲酸和肉桂酸羟基衍生物。
从苯甲酸和肉桂酸衍生物中鉴定出三种底物、四种激活剂和 11 种抑制剂。2,4-二羟基肉桂酸和苯甲酸对 PPO 的抑制作用最强,IC 分别为 0.092 和 1.425mmol/L。苯甲酸以竞争性方式可逆地抑制 PPO,而 2,4-二羟基肉桂酸则表现出混合型抑制。两者均表明静态型荧光猝灭和静电相互作用是结合过程中的主要驱动力。与苯甲酸相比,2,4-二羟基肉桂酸在 PPO 的活性部位更容易形成氢键,使相互作用更加稳定。
比较分析表明,肉桂酸羟基衍生物对 PPO 的抑制作用强于苯甲酸衍生物。苯甲酸和 2,4-二羟基肉桂酸是最强的抑制剂。从苯甲酸和肉桂酸衍生物中鉴定出的 PPO 抑制剂有望成为控制水果和蔬菜褐变的有前途的抑制剂。 © 2021 英国化学学会。