Insight on a Competitive Nucleophilic Addition Reaction of Nε-(Carboxymethyl) Lysine or Different Amino Acids with 4-Methylbenzoquinone
Zhenhui Zhang,
Lin Li,
Yuting Li,
Yi Wu,
Xia Zhang,
Haiping Qi,
Bing Li
Affiliations
Zhenhui Zhang
Guangdong Province Key Laboratory for Green Processing of Natural Products and Product Safety, Engineering Research Center of Starch and Plant Protein Deep Processing, Ministry of Education, School of Food Science and Engineering, South China University of Technology, 381 Wushan Road, Guangzhou 510640, China
Lin Li
Guangdong Province Key Laboratory for Green Processing of Natural Products and Product Safety, Engineering Research Center of Starch and Plant Protein Deep Processing, Ministry of Education, School of Food Science and Engineering, South China University of Technology, 381 Wushan Road, Guangzhou 510640, China
Yuting Li
School of Chemical Engineering and Energy Technology, Dongguan University of Technology, College Road 1, Dongguan 523808, China
Yi Wu
Guangdong Province Key Laboratory for Green Processing of Natural Products and Product Safety, Engineering Research Center of Starch and Plant Protein Deep Processing, Ministry of Education, School of Food Science and Engineering, South China University of Technology, 381 Wushan Road, Guangzhou 510640, China
Xia Zhang
Guangdong Province Key Laboratory for Green Processing of Natural Products and Product Safety, Engineering Research Center of Starch and Plant Protein Deep Processing, Ministry of Education, School of Food Science and Engineering, South China University of Technology, 381 Wushan Road, Guangzhou 510640, China
Haiping Qi
Guangdong Province Key Laboratory for Green Processing of Natural Products and Product Safety, Engineering Research Center of Starch and Plant Protein Deep Processing, Ministry of Education, School of Food Science and Engineering, South China University of Technology, 381 Wushan Road, Guangzhou 510640, China
Bing Li
Guangdong Province Key Laboratory for Green Processing of Natural Products and Product Safety, Engineering Research Center of Starch and Plant Protein Deep Processing, Ministry of Education, School of Food Science and Engineering, South China University of Technology, 381 Wushan Road, Guangzhou 510640, China
ο-benzoquinone is a common intermediate which is mostly formed by the oxidation of phenolics or polyphenols containing catechol structure. ο-benzoquinone has an outstanding nucleophilic ability, while advanced glycation end products (AGEs) are nucleophilic and can undergo a nucleophilic addition reaction with ο-benzoquinone to mitigate the harmful effects of AGEs on the body. As common nucleophilic substances, amino acids existing in large quantities in food processing and in vivo may bind competitively with ο-benzoquinone, thus influencing the trapping of ο-benzoquinone with AGEs. In this study, cyclic voltammetry and coexistence experiments were used to compare the reactivities of Nε-(carboxymethyl) lysine (CML) and amino acids with 4-methylbenzoquinone (4-MBQ). The results showed that CML is more reactive with ο-benzoquinone than most amino acids, and even in complex systems, ο-benzoquinone still captured CML. Moreover, almost all adducts were identified by UPLC-QTOF-MS/MS, and their chemical formulas were deduced. Quantum chemistry accurately predicts the efficiency and site of reactions of ο-benzoquinone and nucleophiles to a certain extent, and found that a secondary amine has a greater reactivity with 4-MBQ than a primary amine in a similar molecular structure. In general, ο-benzoquinone could capture AGEs, thereby showing potential to reduce the harmfulness of AGEs.
