Simultaneous generation of acrylamide, β-carboline heterocyclic amines and advanced glycation ends products in an aqueous Maillard reaction model system

• Published in: Food chemistry 2020-12, Vol.332, p.127387-127387, Article 127387
• Main Authors: Quan, Wei, Li, Yong, Jiao, Ye, Xue, Chaoyi, Liu, Guoping, Wang, Zhaojun, He, Zhiyong, Qin, Fang, Zeng, Maomao, Chen, Jie
• Format: Article
• Language: English
• Subjects: Acrylamide; Harmane; Multiresponse kinetic models; Norharmane; Nε-(carboxyethyl)lysine; Nε-(carboxymethyl)lysine
• ISSN: 0308-8146; 1873-7072
• DOI: 10.1016/j.foodchem.2020.127387

•CML and CEL were formed in a model system heated to 100 °C.•Asn and Trp competed with Lys for GO and MGO when heated to 100 °C.•Harmane formed via Pictet–Spengler condensation between Trp and acetaldehyde.•Asn competed with Lys for glucose, GO and MGO when heated at 130 °C.•Trp inhibited the formation of acrylamide via the acrolein oxidation pathway. The simultaneous formation of acrylamide; β-carboline heterocyclic amines (HAs): harmane and norharmane; and advanced glycation end products (AGEs) (Nε-(carboxymethyl)lysine (CML) and Nε-(carboxyethyl)lysine (CEL)) was analyzed based on an aqueous model system. The model systems included lysine–glucose (Lys/Glu), asparagine–glucose (Asn/Glu), tryptophan–glucose (Trp/Glu), and a mixture of these amino acids (Mix/Glu). Only AGEs were generated when heated at 100 °C, Asn and Trp competed with Lys for glucose and methylglyoxal (MGO), and glyoxal (GO) decreased AGE content. The k value of CML, CEL, and acrylamide decreased when heated at 130 °C, whereas that of harmane increased in the Mix/Glu, owing to the competition between Lys and Asn for glucose, GO, and MGO. Harmane preferably formed via the Pictet–Spengler condensation between Trp and acetaldehyde, which further reduced acrylamide formation via the acrolein pathway.