Abstract
Acrolein, known as one of the most common reactive carbonyl species, is a toxic small molecule affecting human health in daily life. This study is focused on the scavenging abilities and mechanism of ferulic acid and some other phenolic acids against acrolein. Among the 13 phenolic compounds investigated, ferulic acid was found to have the highest efficiency in scavenging acrolein under physiological conditions. Ferulic acid remained at (3.04±1.89)% and acrolein remained at (29.51±4.44)% after being incubated with each other for 24 h. The molecular mechanism of the detoxifying process was also studied. Detoxifying products, namely 2-methoxy-4-vinylphenol (product 21) and 5-(4-hydroxy-3-methoxyphenyl)pent-4-enal (product 22), were identified though nuclear magnetic resonance (NMR) and gas chromatography-mass spectrometry (GC-MS), after the scavenging process. Ferulic acid showed significant activity in scavenging acrolein under physiological conditions. This study indicates a new method for inhibiting damage from acrolein.
概要
目 的
寻找一种方便、 快捷且有效的清除丙烯醛的天然试剂并研究其反应机理。
创新点
发现了常见的天然酚酸阿魏酸具有有效清除丙烯醛的活性, 且其反应位点与其他具有丙烯醛清除活性的酚酸类化合物不同。 研究了该反应的过程, 推测了其反应机理, 并考察了该反应的构效关系。
方 法
(1) 通过相同时间内阿魏酸对丙烯醛、 谷胱甘肽的影响考察其清除活性; (2) 运用气相色谱-质谱联用技术(GC-MS)、 核磁共振技术 (NMR) 等技术鉴定产物结构; (3) 通过研究阿魏酸、 丙烯醛和反应产物之间的互相转化关系, 推断该反应的过程。
结 论
(1) 阿魏酸可以有效抑制丙烯醛对细胞抗氧化系统的破坏; (2)该反应的过程是由阿魏酸在丙烯醛作用下脱羧, 得到脱羧产物, 再与丙烯醛进行迈克尔加成, 得到最终加合产物; (3)苯环 4 号位的羟基对于脱羧过程是必需的; (4) 苯环 3 号位的甲氧基可以大幅度提高加合产物的产率; (5)阿魏酸及其类似物的酯与丙烯醛不发生反应。
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Zhi-hao TAO performed the experimental research and data analysis, wrote and edited the manuscript. Chang LI contributed to the study design, data analysis, writing and editing of the manuscript. Xiao-fei XU contributed to the study design and data analysis of the manuscript. Yuan-jiang PAN contributed to the study design, writing and editing of the manuscript. All authors read and approved the final manuscript and, therefore, had full access to all the data in the study and take responsibility for the integrity and security of the data.
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Zhi-hao TAO, Chang LI, Xiao-fei XU, and Yuan-jiang PAN declare that they have no conflict of interest.
This article does not contain any studies with human or animal subjects performed by any of the authors.
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Project supported by the National Natural Science Foundation of China (Nos. 21327010 and 21372199)
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Tao, Zh., Li, C., Xu, Xf. et al. Scavenging activity and mechanism study of ferulic acid against reactive carbonyl species acrolein. J. Zhejiang Univ. Sci. B 20, 868–876 (2019). https://doi.org/10.1631/jzus.B1900211
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DOI: https://doi.org/10.1631/jzus.B1900211