Characterization of covalent addition products of chlorogenic acid quinone with amino acid derivatives in model systems and apple juice by high-performance liquid chromatography/electrospray ionization tandem mass spectrometry

Rapid Communications in Mass Spectrometry : RCM
Susanne SchillingAndreas Schieber

Abstract

High-performance liquid chromatography (HPLC) coupled to electrospray ionization tandem mass spectrometry (ESI-MS(n)) was used to study the covalent interactions between chlorogenic acid (CQA) quinone and two amino acid derivatives, tert-butyloxycarbonyl-L-lysine and N-acetyl-L-cysteine. In a model system at pH 7.0, the formation of covalent addition products was demonstrated for both derivatives. The addition product of CQA dimer and tert-butyloxycarbonyl-L-lysine was characterized by LC/MS(n) as a benzacridine structure. For N-acetyl-L-cysteine, mono- and diaddition products at the thiol group with CQA quinone were found. In apple juice at pH 3.6, covalent interactions of CQA quinone were observed only with N-acetyl-L-cysteine. Taking together these results and those reported by other groups it can be concluded that covalent interactions of amino side chains with phenolic compounds could contribute to the reduction of the allergenic potential of certain food proteins.

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Citations

Mar 16, 2012·Journal of Agricultural and Food Chemistry·Tomas F M KuijpersHarry Gruppen
Nov 1, 2012·Journal of Agricultural and Food Chemistry·Mostafa AliHarshadrai Rawel
Jan 31, 2013·Journal of Agricultural and Food Chemistry·Carlos-Eduardo Narváez-CuencaHarry Gruppen
Jun 25, 2013·Journal of Agricultural and Food Chemistry·Mostafa AliHarshadrai Rawel
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Jan 20, 2016·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Verena BongartzAndreas Schieber
Oct 17, 2015·Food Chemistry·Annika ReinkensmeierHashadrai M Rawel
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Feb 14, 2017·Langmuir : the ACS Journal of Surfaces and Colloids·Mariagrazia IacominoMarco d'Ischia
Feb 6, 2017·Current Pharmaceutical Design·Maria Rosa Perez-Gregorio, Jesus Simal-Gandara
Sep 1, 2016·Comprehensive Reviews in Food Science and Food Safety·Sabrina R WildermuthLilian M Were
Apr 2, 2021·Critical Reviews in Food Science and Nutrition·Büşra Gültekin SubaşıMohammad Amin Mohammadifar
Nov 27, 2018·Journal of Agricultural and Food Chemistry·Andreas Schieber
Feb 1, 2019·Journal of Agricultural and Food Chemistry·Nils MertensMarcus A Glomb

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