The Simultaneous Formation of Acrylamide, β-carbolines, and Advanced Glycation End Products in a Chemical Model System: Effect of Multiple Precursor Amino Acids
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., Nε-(carboxymethyl)lysine and Nε-(carboxyethyl)lysine] via a chemical model system. This mo...
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| Format: | Article |
| Language: | English |
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Frontiers Media S.A.
2022-03-01
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| Series: | Frontiers in Nutrition |
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| Online Access: | https://www.frontiersin.org/articles/10.3389/fnut.2022.852717/full |
| _version_ | 1818487684189913088 |
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| author | Cuyu Chen Ye Jiao Maomao Zeng Zhiyong He Qingwu Shen Jie Chen Jie Chen Wei Quan Wei Quan |
| author_facet | Cuyu Chen Ye Jiao Maomao Zeng Zhiyong He Qingwu Shen Jie Chen Jie Chen Wei Quan Wei Quan |
| author_sort | Cuyu Chen |
| collection | DOAJ |
| description | 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., Nε-(carboxymethyl)lysine and Nε-(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 k 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. |
| first_indexed | 2024-12-10T16:41:25Z |
| format | Article |
| id | doaj.art-a67c4af3eda4487f91193ec7c21fa707 |
| institution | Directory Open Access Journal |
| issn | 2296-861X |
| language | English |
| last_indexed | 2024-12-10T16:41:25Z |
| publishDate | 2022-03-01 |
| publisher | Frontiers Media S.A. |
| record_format | Article |
| series | Frontiers in Nutrition |
| spelling | doaj.art-a67c4af3eda4487f91193ec7c21fa7072022-12-22T01:41:14ZengFrontiers Media S.A.Frontiers in Nutrition2296-861X2022-03-01910.3389/fnut.2022.852717852717The Simultaneous Formation of Acrylamide, β-carbolines, and Advanced Glycation End Products in a Chemical Model System: Effect of Multiple Precursor Amino AcidsCuyu Chen0Ye Jiao1Maomao Zeng2Zhiyong He3Qingwu Shen4Jie Chen5Jie Chen6Wei Quan7Wei Quan8College of Food Science and Technology, Hunan Agricultural University, Changsha, ChinaSchool of Chemistry and Food Engineering, Changsha University of Science and Technology, Changsha, ChinaState Key Laboratory of Food Science and Technology, Jiangnan University, Wuxi, ChinaState Key Laboratory of Food Science and Technology, Jiangnan University, Wuxi, ChinaCollege of Food Science and Technology, Hunan Agricultural University, Changsha, ChinaState Key Laboratory of Food Science and Technology, Jiangnan University, Wuxi, ChinaInternational Joint Laboratory on Food Safety, Jiangnan University, Wuxi, ChinaCollege of Food Science and Technology, Hunan Agricultural University, Changsha, ChinaState Key Laboratory of Food Science and Technology, Jiangnan University, Wuxi, ChinaThis 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., Nε-(carboxymethyl)lysine and Nε-(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 k 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.https://www.frontiersin.org/articles/10.3389/fnut.2022.852717/fullprecursor amino acidsacrylamideNε-(carboxymethyl)lysineNε-(carboxyethyl)lysineβ-carboline heterocyclic amines |
| spellingShingle | Cuyu Chen Ye Jiao Maomao Zeng Zhiyong He Qingwu Shen Jie Chen Jie Chen Wei Quan Wei Quan The Simultaneous Formation of Acrylamide, β-carbolines, and Advanced Glycation End Products in a Chemical Model System: Effect of Multiple Precursor Amino Acids Frontiers in Nutrition precursor amino acids acrylamide Nε-(carboxymethyl)lysine Nε-(carboxyethyl)lysine β-carboline heterocyclic amines |
| title | The Simultaneous Formation of Acrylamide, β-carbolines, and Advanced Glycation End Products in a Chemical Model System: Effect of Multiple Precursor Amino Acids |
| title_full | The Simultaneous Formation of Acrylamide, β-carbolines, and Advanced Glycation End Products in a Chemical Model System: Effect of Multiple Precursor Amino Acids |
| title_fullStr | The Simultaneous Formation of Acrylamide, β-carbolines, and Advanced Glycation End Products in a Chemical Model System: Effect of Multiple Precursor Amino Acids |
| title_full_unstemmed | The Simultaneous Formation of Acrylamide, β-carbolines, and Advanced Glycation End Products in a Chemical Model System: Effect of Multiple Precursor Amino Acids |
| title_short | The Simultaneous Formation of Acrylamide, β-carbolines, and Advanced Glycation End Products in a Chemical Model System: Effect of Multiple Precursor Amino Acids |
| title_sort | simultaneous formation of acrylamide β carbolines and advanced glycation end products in a chemical model system effect of multiple precursor amino acids |
| topic | precursor amino acids acrylamide Nε-(carboxymethyl)lysine Nε-(carboxyethyl)lysine β-carboline heterocyclic amines |
| url | https://www.frontiersin.org/articles/10.3389/fnut.2022.852717/full |
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