Effect of pH on the reaction between naringenin and methylglyoxal: a kinetic study
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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.
I: Food Chemistry, Bind 298, 125086, 2019.Publikation: Bidrag til tidsskrift › Tidsskriftartikel › Forskning › fagfællebedømt
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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