Kinetic study on the generation of furosine and pyrraline in a Maillard reaction model system of d-glucose and l-lysine. (1st July 2020)

• Record Type: Journal Article
• Authors: Yu, Hang; Zhong, Qili; Xie, Yunfei; Guo, Yahui; Cheng, Yuliang; Yao, Weirong
• Is Part Of: Food chemistry. Volume 317(2020)
• Publication Date: 2020-07-01
• Subjects: MR Maillard reaction -- MRPs Maillard reaction products -- AGEs advanced glycation end-products -- DFG N-(1-deoxy-d-fructose-1-yl)-glycine -- MFL monofructosyl-l-lysine -- DFL difructosyl-l-lysine -- 1-DG 1-deoxyglucosone -- 3-DG 3-deoxyglucosone -- MG methylglyoxal -- GO glyoxal -- CML NƐ-(carboxymethyl)lysine -- CEL NƐ-(hydroxyethyl) lysine -- HPLC high-pressure liquid chromatography -- OPD o-phenylenediamine -- PDA photo-diode array detector -- RMSE relative mean square error; Kinetic study -- Maillard reaction -- d-Glucose -- l-Lysine -- Furosine -- Pyrraline -- 3-Deoxyglucosone -- Methylglyoxal; Food -- Analysis -- Periodicals; Food -- Composition -- Periodicals; 664
• DOI: 10.1016/j.foodchem.2020.126458
• Languages: English
• ISSNs: 0308-8146

Abstract

Highlights: A Maillard reaction (MR) model system of d -glucose and l -lysine was investigated. Generation mechanisms of furosine and pyrraline were revealed in the MR model system. Furosine is preferred to undergo the reaction between methylglyoxal and l -lysine. Pyrraline is preferentially started from 3-deoxyglucosone through Pyrrole reaction. Abstract: A kinetic model for Maillard reaction (MR) model system of d -glucose and l -lysine was established; activation energy ( Ea ) of each step was calculated. Potential generation pathways of furosine and pyrraline were a combination of either 3-deoxyglucosone (3-DG) or methylglyoxal (MG) with l -lysine. Ea value for furosine generated through 3-DG pathway was 81.70 ± 14.01 kJ mol −1, which was significantly higher than that through MG pathway (52.08 ± 4.48 kJ mol −1 ). As for pyrraline, Ea for the 3-DG pathway (53.45 ± 4.02 kJ mol −1 ) was significantly lower than that through the MG pathway (110.22 ± 18.77 kJ mol −1 ). Results of the kinetic study indicated that furosine was preferred to be generated through the MG pathway since MG is more likely to react with each other and form a furan ring as a precursor of furosine. Pyrraline was more easily to be generated from the 3-DG pathway through cyclization of 1, 4-dicarbonyl compounds to pyrrole.