Effect of pH on the reaction between naringenin and methylglyoxal: a kinetic study

Research output: Contribution to journalJournal articlepeer-review

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Effect of pH on the reaction between naringenin and methylglyoxal : a kinetic study. / Zhu, Hongkai; Poojary, Mahesha M.; Andersen, Mogens L.; Lund, Marianne N.

In: Food Chemistry, Vol. 298, 125086, 2019.

Research output: Contribution to journalJournal articlepeer-review

Harvard

Zhu, H, Poojary, MM, Andersen, ML & Lund, MN 2019, 'Effect of pH on the reaction between naringenin and methylglyoxal: a kinetic study', Food Chemistry, vol. 298, 125086. https://doi.org/10.1016/j.foodchem.2019.125086

APA

Zhu, H., Poojary, M. M., Andersen, M. L., & Lund, M. N. (2019). Effect of pH on the reaction between naringenin and methylglyoxal: a kinetic study. Food Chemistry, 298, [125086]. https://doi.org/10.1016/j.foodchem.2019.125086

Vancouver

Zhu H, Poojary MM, Andersen ML, Lund MN. Effect of pH on the reaction between naringenin and methylglyoxal: a kinetic study. Food Chemistry. 2019;298. 125086. https://doi.org/10.1016/j.foodchem.2019.125086

Author

Zhu, Hongkai ; Poojary, Mahesha M. ; Andersen, Mogens L. ; Lund, Marianne N. / Effect of pH on the reaction between naringenin and methylglyoxal : a kinetic study. In: Food Chemistry. 2019 ; Vol. 298.

Bibtex

@article{3661dd42375e4f4bb81a9cc1d977c68c,
title = "Effect of pH on the reaction between naringenin and methylglyoxal: a kinetic study",
abstract = "Methylglyoxal (MGO) is a highly reactive alpha-dicarbonyl compound that may adversely impact food quality and human health by modifying proteins. The kinetics of the reaction of naringenin with MGO was studied at pH 6-8 and 37 degrees C by UV-Vis spectrophotometry and reaction products were characterized by liquid chromatography-mass spectrometry (LC-MS/MS). The apparent second order rate constant (k(2)) increased at pH above the lowest pKa value of naringenin, indicating deprotonated naringenin as the main reactant. A Lederer-Manasse type reaction mechanism is suggested, with dehydration of the MGO-dihydrate as a rate determining step. The quantitative data obtained in the present study was used to simulate the competitive reaction between MGO and nucleophilic amino acid residues (Lys, Arg and Cys) and naringenin in milk. It is predicted that naringenin will be able to efficiently trap MGO during storage of milk, although the reversible trapping of MGO by Cys residues is initially kinetically favourable.",
keywords = "Methylglyoxal, alpha-Dicarbonyls, Maillard reactions, Naringenin, Kinetics, pH, Simulation, UHT milk",
author = "Hongkai Zhu and Poojary, {Mahesha M.} and Andersen, {Mogens L.} and Lund, {Marianne N.}",
year = "2019",
doi = "10.1016/j.foodchem.2019.125086",
language = "English",
volume = "298",
journal = "Food Chemistry",
issn = "0308-8146",
publisher = "Elsevier",

}

RIS

TY - JOUR

T1 - Effect of pH on the reaction between naringenin and methylglyoxal

T2 - a kinetic study

AU - Zhu, Hongkai

AU - Poojary, Mahesha M.

AU - Andersen, Mogens L.

AU - Lund, Marianne N.

PY - 2019

Y1 - 2019

N2 - Methylglyoxal (MGO) is a highly reactive alpha-dicarbonyl compound that may adversely impact food quality and human health by modifying proteins. The kinetics of the reaction of naringenin with MGO was studied at pH 6-8 and 37 degrees C by UV-Vis spectrophotometry and reaction products were characterized by liquid chromatography-mass spectrometry (LC-MS/MS). The apparent second order rate constant (k(2)) increased at pH above the lowest pKa value of naringenin, indicating deprotonated naringenin as the main reactant. A Lederer-Manasse type reaction mechanism is suggested, with dehydration of the MGO-dihydrate as a rate determining step. The quantitative data obtained in the present study was used to simulate the competitive reaction between MGO and nucleophilic amino acid residues (Lys, Arg and Cys) and naringenin in milk. It is predicted that naringenin will be able to efficiently trap MGO during storage of milk, although the reversible trapping of MGO by Cys residues is initially kinetically favourable.

AB - Methylglyoxal (MGO) is a highly reactive alpha-dicarbonyl compound that may adversely impact food quality and human health by modifying proteins. The kinetics of the reaction of naringenin with MGO was studied at pH 6-8 and 37 degrees C by UV-Vis spectrophotometry and reaction products were characterized by liquid chromatography-mass spectrometry (LC-MS/MS). The apparent second order rate constant (k(2)) increased at pH above the lowest pKa value of naringenin, indicating deprotonated naringenin as the main reactant. A Lederer-Manasse type reaction mechanism is suggested, with dehydration of the MGO-dihydrate as a rate determining step. The quantitative data obtained in the present study was used to simulate the competitive reaction between MGO and nucleophilic amino acid residues (Lys, Arg and Cys) and naringenin in milk. It is predicted that naringenin will be able to efficiently trap MGO during storage of milk, although the reversible trapping of MGO by Cys residues is initially kinetically favourable.

KW - Methylglyoxal

KW - alpha-Dicarbonyls

KW - Maillard reactions

KW - Naringenin

KW - Kinetics

KW - pH

KW - Simulation

KW - UHT milk

U2 - 10.1016/j.foodchem.2019.125086

DO - 10.1016/j.foodchem.2019.125086

M3 - Journal article

C2 - 31272050

VL - 298

JO - Food Chemistry

JF - Food Chemistry

SN - 0308-8146

M1 - 125086

ER -

ID: 225664240