Carbonyl Chemistry and the Formation of Heterocyclic Aromatic Amines with the Structure of Aminoimidazoazaarene

被引:34
作者
Hidalgo, Francisco J. [1 ]
Zamora, Rosario [1 ]
机构
[1] CSIC, Inst Grasa, Seville 41013, Spain
关键词
carbonyl-amine reactions; carbonyl-phenol reactions; lipid oxidation; heterocyclic aromatic amines; Maillard reaction; reactive carbonyls; MITIGATION STRATEGIES; STRECKER DEGRADATION; PHIP;
D O I
10.1021/acs.jafc.1c06842
中图分类号
S [农业科学];
学科分类号
09 ;
摘要
Recent studies have shown that the formation of heterocyclic aromatic amines (HAAs) with the structure of aminoimidazoazaarene is produced by reaction of specific reactive carbonyls with ammonia and creatin(in)e. These carbonyl compounds, which are usually the limiting reagents, have multiple origins. Therefore, HAA formation cannot be considered to be produced as a consequence of a single process, such as the Maillard reaction, but of any process that generates the involved reactive carbonyls. In addition, inhibition of HAA formation should be related to the control of these reactive carbonyls: inhibiting their formation, using conditions that limit their reactivity, and promoting their trapping.
引用
收藏
页码:79 / 86
页数:8
相关论文
共 30 条
[1]  
[Anonymous], 1993, IARC Monogr Eval Carcinog Risks Hum, V56, P445
[2]  
[Anonymous], 2018, Red Meat and Processed Meat, IARC Monographs on the Evaluation of Carcinogenic Risks to Humans Volume, V114
[3]   Antagonism between lipid-derived reactive carbonyls and phenolic compounds in the Strecker degradation of amino acids [J].
Delgado, Rosa M. ;
Hidalgo, Francisco J. ;
Zamora, Rosario .
FOOD CHEMISTRY, 2016, 194 :1143-1148
[4]   Identification of acrolein as the reactive carbonyl responsible for the formation of 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline (MeIQx) [J].
Hidalgo, Francisco J. ;
Lavado-Tena, Cristina M. ;
Zamora, Rosario .
FOOD CHEMISTRY, 2021, 343
[5]   Formation of phenylacetic acid and benzaldehyde by degradation of phenylalanine in the presence of lipid hydroperoxides: New routes in the amino acid degradation pathways initiated by lipid oxidation products [J].
Hidalgo, Francisco J. ;
Zamora, Rosario .
FOOD CHEMISTRY-X, 2019, 2
[6]   Structure-Activity Relationship (SAR) of Phenolics for 2-Amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) Formation in Phenylalanine/Creatinine Reaction Mixtures Including (or Not) Oxygen and Lipid Hydroperoxides [J].
Hidalgo, Francisco J. ;
Navarro, Jose L. ;
Zamora, Rosario .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2018, 66 (01) :255-264
[7]   Amino Acid Degradations Produced by Lipid Oxidation Products [J].
Hidalgo, Francisco J. ;
Zamora, Rosario .
CRITICAL REVIEWS IN FOOD SCIENCE AND NUTRITION, 2016, 56 (08) :1242-1252
[8]   Reactive Carbonyl-Scavenging Ability of 2-Aminoimidazoles: 2-Amino-1-methylbenzimidazole and 2-Amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) [J].
Hidalgo, Francisco J. ;
Alcon, Esmeralda ;
Zamora, Rosario .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2014, 62 (49) :12045-12051
[9]   RELATIVE REACTIVITIES OF AMINO-ACIDS IN PYRAZINE FORMATION [J].
HWANG, HI ;
HARTMAN, TG ;
HO, CT .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1995, 43 (01) :179-184
[10]   Amino acids effects on heterocyclic amines formation and physicochemical properties in pan-fried beef patties [J].
Linghu Ziyi ;
Karim, Faris ;
Taghvaei, Mostafa ;
Albashabsheh, Zaher ;
Houser, Terry A. ;
Smith, J. Scott .
JOURNAL OF FOOD SCIENCE, 2020, 85 (04) :1361-1370