动力学研究 4-甲基苯醌对 Nε-(羧甲基)赖氨酸的捕获：控制食品中 Nε-(羧甲基)赖氨酸水平的新机制。
Kinetic investigation of the trapping of Nε-(carboxymethyl)lysine by 4-methylbenzoquinone: A new mechanism to control Nε-(carboxymethyl)lysine levels in foods.
机构信息
School of Food Science and Technology, South China University of Technology, Guangzhou 510640, China; School of Chemical Engineering and Energy Technology, Dongguan University of Technology, Dongguan 523808, China.
School of Food Science and Technology, South China University of Technology, Guangzhou 510640, China; School of Chemical Engineering and Energy Technology, Dongguan University of Technology, Dongguan 523808, China; Guangdong Province Key Laboratory for Green Processing of Natural Products and Product Safety, Guangzhou 510640, China.
出版信息
Food Chem. 2018 Apr 1;244:25-28. doi: 10.1016/j.foodchem.2017.09.144. Epub 2017 Sep 29.
o-Benzoquinones, formed during oxidation of polyphenols, react with amines through a Michael addition. In the present study, the ability of 4-methylbenzoquinone (4MBQ) to trap Nε-(carboxymethyl)lysine (CML) through a Michael addition with the amine groups on CML was investigated at different pH values. Apparent second order rate constants (k) for the reaction of 4MBQ with CML were determined by stopped-flow spectrophotometry at 25 °C to be ∼0.0 M s at pH 5, 9.5 M s at pH 7, and 164.5 M s at pH 8 based on the loss of 4MBQ at 401 nm. The reaction between 4MBQ and CML generated coloured CML-quinone compounds via colourless CML-phenol species as identified by LC-ESI-MS/MS. These data provide evidence that CML formed during food production can be trapped by o-benzoquinones, which is a new mechanism by which polyphenols may be used to control CML levels in foods.
邻苯醌在多酚氧化过程中形成，通过迈克尔加成反应与胺类物质反应。在本研究中，研究了 4-甲基苯醌（4MBQ）在不同 pH 值下通过与 CML 上的胺基发生迈克尔加成反应来捕获 Nε-（羧甲基）赖氨酸（CML）的能力。在 25°C 下通过停流分光光度法确定了 4MBQ 与 CML 的反应的表观二级速率常数（k），在 pH 5 时约为 0.0 M s，在 pH 7 时约为 9.5 M s，在 pH 8 时约为 164.5 M s，基于 401 nm 处 4MBQ 的损失。4MBQ 和 CML 之间的反应通过无色的 CML-酚类物质生成有色的 CML-醌类化合物，这通过 LC-ESI-MS/MS 进行了鉴定。这些数据提供了证据表明，食品生产过程中形成的 CML 可以被邻苯醌捕获，这是多酚类物质可能用于控制食品中 CML 水平的新机制。
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