Comparison of pyrazines formation in methionine/glucose and corresponding Amadori rearrangement product model

Shibin Deng; Heping Cui; Khizar Hayat; Yun Zhai; Qiang Zhang; Xiaoming Zhang; Chi-Tang Ho

doi:10.1016/j.foodchem.2022.132500

Comparison of pyrazines formation in methionine/glucose and corresponding Amadori rearrangement product model

Food Chem. 2022 Jul 15:382:132500. doi: 10.1016/j.foodchem.2022.132500. Epub 2022 Feb 19.

Authors

Shibin Deng¹, Heping Cui², Khizar Hayat³, Yun Zhai⁴, Qiang Zhang⁵, Xiaoming Zhang⁶, Chi-Tang Ho⁷

Affiliations

¹ State Key Laboratory of Food Science and Technology, School of Food Science and Technology, Collaborative Innovation Center of Food Safety and Quality Control in Jiangsu Province, Jiangnan University, 1800 Lihu Avenue, Wuxi 214122, Jiangsu, PR China; Fujian Provincial Key Laboratory of Ecology-Toxicological Effects & Control for Emerging Contaminants, College of Environmental and Biological Engineering, Putian University, Putian 351100, Fujian, PR China; Key Laboratory of Ecological Environment and Information Atlas (Putian University) Fujian Provincial University, College of Environmental and Biological Engineering, Putian University, Putian 351100, Fujian, PR China. Electronic address: sbindeng@126.com.
² State Key Laboratory of Food Science and Technology, School of Food Science and Technology, Collaborative Innovation Center of Food Safety and Quality Control in Jiangsu Province, Jiangnan University, 1800 Lihu Avenue, Wuxi 214122, Jiangsu, PR China. Electronic address: cuihepingdavid@126.com.
³ Department of Kinesiology, Nutrition, and Health, Miami University, Oxford, OH 45056, USA. Electronic address: hayatk@miamioh.edu.
⁴ State Key Laboratory of Food Science and Technology, School of Food Science and Technology, Collaborative Innovation Center of Food Safety and Quality Control in Jiangsu Province, Jiangnan University, 1800 Lihu Avenue, Wuxi 214122, Jiangsu, PR China. Electronic address: 18352538819@126.com.
⁵ Anhui Province Key Laboratory of Functional Compound Seasoning, Anhui Qiangwang Flavouring Food Co., LTD, No. 1 Shengli Road, Jieshou, Anhui 236500, PR China. Electronic address: laomuji888@163.com.
⁶ State Key Laboratory of Food Science and Technology, School of Food Science and Technology, Collaborative Innovation Center of Food Safety and Quality Control in Jiangsu Province, Jiangnan University, 1800 Lihu Avenue, Wuxi 214122, Jiangsu, PR China. Electronic address: xmzhang@jiangnan.edu.cn.
⁷ Department of Food Science, Rutgers University, 65 Dudley Road, New Brunswick, NJ 08901, USA. Electronic address: ctho@sebs.rutgers.edu.

PMID: 35245757
DOI: 10.1016/j.foodchem.2022.132500

Abstract

The generation of pyrazines in a binary methionine/glucose (Met/Glc) mixture and corresponding methionine/glucose-derived Amadori rearrangement product (MG-ARP) was studied. Quantitative analyses of pyrazines and methional revealed that MG-ARP generated more methional compared to Met/Glc, whereas lower content and fewer species of pyrazines were observed in the MG-ARP model. Comparing the availability of α-dicarbonyl compounds generated from the Met/Glc model, methylglyoxal (MGO) was a considerably effective α-dicarbonyl compound for the formation of pyrazines during MG-ARP degradation, but glyoxal (GO) produced from MG-ARP did not effectively participate in the corresponding formation of pyrazines due to the asynchrony on the formation of GO and recovered Met. Diacetyl (DA) content was not high enough to form corresponding pyrazines in the MG-ARP model. The insufficient interaction of precursors and rapid drops in pH limited the formation of pyrazines during MG-ARP degradation. Increasing reaction temperature could reduce the negative inhibitory effect by promoting the content of precursors.

Keywords: 2,3-Diethylpyrazine (PubChem CID27458); 2,3-Dimethylpyrazine (PubChem CID22201); 2,5-Dimethylpyrazine (PubChem CID31252); 2,6-Dimethylpyrazine (PubChem CID7938); 2-Ethyl-3,5-dimethylpyrazine (PubChem CID26334); 2-Ethyl-5-methylpyrazine (PubChem CID25915); Acetylpyrazine (PubChem CID30914); Amadori rearrangement product; Ethylpyrazine (PubChem CID26331); Methional; Methional (PubChem CID18635); Methionine; Methylpyrazine (PubChem CID7976); Pyrazine (PubChem CID9261); Pyrazines; Trimethylpyrazine (PubChem CID26808); Vinylpyrazine (PubChem CID77840); d-Glucose (PubChem CID5793); dl-methionine (PubChem CID876); α-Dicarbonyl compounds.

MeSH terms

Glucose
Glyoxal
Maillard Reaction*
Methionine*
Pyrazines / chemistry

Substances

Pyrazines
Glyoxal
Methionine
Glucose