The effect of molecular structure of polyphenols on the kinetics of the trapping reactions with methylglyoxal
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The effect of molecular structure of polyphenols on the kinetics of the trapping reactions with methylglyoxal. / Zhu, Hongkai; Poojary, Mahesha M.; Andersen, Mogens L.; Lund, Marianne N.
In: Food Chemistry, Vol. 319, 126500, 2020.Research output: Contribution to journal › Journal article › peer-review
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TY - JOUR
T1 - The effect of molecular structure of polyphenols on the kinetics of the trapping reactions with methylglyoxal
AU - Zhu, Hongkai
AU - Poojary, Mahesha M.
AU - Andersen, Mogens L.
AU - Lund, Marianne N.
PY - 2020
Y1 - 2020
N2 - Reaction kinetics for the reactions between four polyphenols (trans-resveratrol, apigenin, kaempferol and fisetin) and methylglyoxal (MGO) were determined at pH 7.4 and 37 °C, and the effect of functional groups of polyphenols on MGO trapping ability was examined. Reaction products of polyphenols with MGO were characterized by HPLC-MS/MS. The apparent second order rate constants for the reaction of MGO with trans-resveratrol, apigenin, kaempferol and fisetin were (2.7 ± 0.2) × 10−2 M−1 s−1, (4.4 ± 0.4) × 10−3 M−1 s−1, (6.3 ± 0.2) × 10−2 M−1 s−1, and (3.6 ± 0.1) × 10−3 M−1 s−1, respectively. The rate constants were used to evaluate the possible competition between MGO with nucleophilic sites on proteins and polyphenols at concentrations relevant to UHT milk. Combining this information with solubility and flavour of the polyphenols, it was concluded that kaempferol could effectively trap MGO and hereby inhibit Maillard reactions in UHT milk.
AB - Reaction kinetics for the reactions between four polyphenols (trans-resveratrol, apigenin, kaempferol and fisetin) and methylglyoxal (MGO) were determined at pH 7.4 and 37 °C, and the effect of functional groups of polyphenols on MGO trapping ability was examined. Reaction products of polyphenols with MGO were characterized by HPLC-MS/MS. The apparent second order rate constants for the reaction of MGO with trans-resveratrol, apigenin, kaempferol and fisetin were (2.7 ± 0.2) × 10−2 M−1 s−1, (4.4 ± 0.4) × 10−3 M−1 s−1, (6.3 ± 0.2) × 10−2 M−1 s−1, and (3.6 ± 0.1) × 10−3 M−1 s−1, respectively. The rate constants were used to evaluate the possible competition between MGO with nucleophilic sites on proteins and polyphenols at concentrations relevant to UHT milk. Combining this information with solubility and flavour of the polyphenols, it was concluded that kaempferol could effectively trap MGO and hereby inhibit Maillard reactions in UHT milk.
KW - Kinetic simulation
KW - Maillard reaction
KW - Methylglyoxal
KW - Molecular structure
KW - Polyphenols
KW - Reaction kinetics
KW - UHT milk
KW - α-Dicarbonyls
U2 - 10.1016/j.foodchem.2020.126500
DO - 10.1016/j.foodchem.2020.126500
M3 - Journal article
C2 - 32146288
AN - SCOPUS:85080955157
VL - 319
JO - Food Chemistry
JF - Food Chemistry
SN - 0308-8146
M1 - 126500
ER -
ID: 238743482