Epicatechin and epigallocatechin gallate inhit formation of intermediary radicals during heating of lysine and glucose

Jie Yin; Rikke Susanne Vingborg Hedegaard; Leif Horsfelt Skibsted; Mogens Larsen Andersen

doi:10.1016/j.foodchem.2013.09.032

Epicatechin and epigallocatechin gallate inhit formation of intermediary radicals during heating of lysine and glucose

Jie Yin, Rikke Susanne Vingborg Hedegaard, Leif Horsfelt Skibsted, Mogens Larsen Andersen

Food Chemistry

28 Citations (Scopus)

Abstract

High concentrations of the tea catechins epicatechin (EC) or epigallocatechin gallate (EGCG) inhibited formation of highly reactive intermediary radicals appearing during the Maillard reactions (MR), that take place during heating glucose and lysine at 70 C in EtOH/HEPES buffer at pH 7.0 and pH 8.0. Radicals were trapped by ethanol, which subsequently were converted into spin adducts of the spin trap α(4-pyridyl N-oxide)-N-tert- butylnitrone (POBN). EGCG was found to be more efficient than EC as inhibitor of intermediary radicals during the MR. Based on UV/Vis-spectroscopy, measurement of oxygen consumption and LC-MS detection of intermediates, it is suggested that the quinone form of autoxidised EC reacts with lysine through either a Michael type addition or a "Strecker like" reaction and thereby influences the formation of intermediary MR products as well as radicals.

Original language	English
Journal	Food Chemistry
Volume	146
Pages (from-to)	48-55
Number of pages	8
ISSN	0308-8146
DOIs	https://doi.org/10.1016/j.foodchem.2013.09.032
Publication status	Published - 2014

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10.1016/j.foodchem.2013.09.032

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title = "Epicatechin and epigallocatechin gallate inhit formation of intermediary radicals during heating of lysine and glucose",

abstract = "High concentrations of the tea catechins epicatechin (EC) or epigallocatechin gallate (EGCG) inhibited formation of highly reactive intermediary radicals appearing during the Maillard reactions (MR), that take place during heating glucose and lysine at 70 C in EtOH/HEPES buffer at pH 7.0 and pH 8.0. Radicals were trapped by ethanol, which subsequently were converted into spin adducts of the spin trap α(4-pyridyl N-oxide)-N-tert- butylnitrone (POBN). EGCG was found to be more efficient than EC as inhibitor of intermediary radicals during the MR. Based on UV/Vis-spectroscopy, measurement of oxygen consumption and LC-MS detection of intermediates, it is suggested that the quinone form of autoxidised EC reacts with lysine through either a Michael type addition or a {"}Strecker like{"} reaction and thereby influences the formation of intermediary MR products as well as radicals.",

author = "Jie Yin and Hedegaard, {Rikke Susanne Vingborg} and Skibsted, {Leif Horsfelt} and Andersen, {Mogens Larsen}",

year = "2014",

doi = "10.1016/j.foodchem.2013.09.032",

language = "English",

volume = "146",

pages = "48--55",

journal = "Food Chemistry",

issn = "0308-8146",

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TY - JOUR

T1 - Epicatechin and epigallocatechin gallate inhit formation of intermediary radicals during heating of lysine and glucose

AU - Yin, Jie

AU - Hedegaard, Rikke Susanne Vingborg

AU - Skibsted, Leif Horsfelt

AU - Andersen, Mogens Larsen

PY - 2014

Y1 - 2014

N2 - High concentrations of the tea catechins epicatechin (EC) or epigallocatechin gallate (EGCG) inhibited formation of highly reactive intermediary radicals appearing during the Maillard reactions (MR), that take place during heating glucose and lysine at 70 C in EtOH/HEPES buffer at pH 7.0 and pH 8.0. Radicals were trapped by ethanol, which subsequently were converted into spin adducts of the spin trap α(4-pyridyl N-oxide)-N-tert- butylnitrone (POBN). EGCG was found to be more efficient than EC as inhibitor of intermediary radicals during the MR. Based on UV/Vis-spectroscopy, measurement of oxygen consumption and LC-MS detection of intermediates, it is suggested that the quinone form of autoxidised EC reacts with lysine through either a Michael type addition or a "Strecker like" reaction and thereby influences the formation of intermediary MR products as well as radicals.

AB - High concentrations of the tea catechins epicatechin (EC) or epigallocatechin gallate (EGCG) inhibited formation of highly reactive intermediary radicals appearing during the Maillard reactions (MR), that take place during heating glucose and lysine at 70 C in EtOH/HEPES buffer at pH 7.0 and pH 8.0. Radicals were trapped by ethanol, which subsequently were converted into spin adducts of the spin trap α(4-pyridyl N-oxide)-N-tert- butylnitrone (POBN). EGCG was found to be more efficient than EC as inhibitor of intermediary radicals during the MR. Based on UV/Vis-spectroscopy, measurement of oxygen consumption and LC-MS detection of intermediates, it is suggested that the quinone form of autoxidised EC reacts with lysine through either a Michael type addition or a "Strecker like" reaction and thereby influences the formation of intermediary MR products as well as radicals.

U2 - 10.1016/j.foodchem.2013.09.032

DO - 10.1016/j.foodchem.2013.09.032

M3 - Journal article

C2 - 24176312

SN - 0308-8146

VL - 146

SP - 48

EP - 55

JO - Food Chemistry

JF - Food Chemistry

ER -

Epicatechin and epigallocatechin gallate inhit formation of intermediary radicals during heating of lysine and glucose

Abstract

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