Chen Cuyu, Jiao Ye, Zeng Maomao, He Zhiyong, Shen Qingwu, Chen Jie, Quan Wei
College of Food Science and Technology, Hunan Agricultural University, Changsha, China.
School of Chemistry and Food Engineering, Changsha University of Science and Technology, Changsha, China.
Front Nutr. 2022 Mar 9;9:852717. doi: 10.3389/fnut.2022.852717. eCollection 2022.
This study investigated the effect of multiple precursor amino acids on the simultaneous formation of acrylamide, β-carbolines (i. e., harmane and norharmane), and advanced glycation end products (AGEs) [i.e., N-(carboxymethyl)lysine and N-(carboxyethyl)lysine] via a chemical model system. This model system was established with single or multiple precursor amino acids, including lysine-glucose (Lys/Glu), asparagine-glucose (Asn/Glu), tryptophan-glucose (Trp/Glu), and a combination of these amino acids (Com/Glu). Kinetic parameters were calculated by multiresponse non-linear regression models. We found that the values of the AGEs and of acrylamide decreased, while those of harmane increased in the Com/Glu model when heated to 170 and 200°C. Our results indicated that the precursor amino acid of acrylamide and AGEs compete for α-dicarbonyl compounds, leading to a decrease in the formation of AGEs and acrylamide. Moreover, compared with asparagine, the precursor amino acid of β-carbolines was more likely to react with acetaldehyde by Pictet-Spengler condensation, which increased the formation of harmane and decreased the formation of acrylamide via the acrolein pathway.
本研究通过化学模型系统，研究了多种前体氨基酸对丙烯酰胺、β-咔啉（即哈尔满和去甲哈尔满）以及晚期糖基化终产物（AGEs，即N-（羧甲基）赖氨酸和N-（羧乙基）赖氨酸）同时形成的影响。该模型系统由单一或多种前体氨基酸构建而成，包括赖氨酸-葡萄糖（Lys/Glu）、天冬酰胺-葡萄糖（Asn/Glu）、色氨酸-葡萄糖（Trp/Glu）以及这些氨基酸的组合（Com/Glu）。通过多响应非线性回归模型计算动力学参数。我们发现，在Com/Glu模型中加热至170℃和200℃时，AGEs和丙烯酰胺的值降低，而哈尔满的值升高。我们的结果表明，丙烯酰胺和AGEs的前体氨基酸竞争α-二羰基化合物，导致AGEs和丙烯酰胺的形成减少。此外，与天冬酰胺相比，β-咔啉的前体氨基酸更易通过Pictet-Spengler缩合反应与乙醛发生反应，这增加了哈尔满的形成，并通过丙烯醛途径减少了丙烯酰胺的形成。
