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.
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.
Schilling
Susanne
S
Hohenheim University, Institute of Food Science and Biotechnology, Section Plant Foodstuff Technology, August-von-Hartmann-Strasse 3, 70599 Stuttgart, Germany.
Sigolotto
Constance-Isabelle
CI
Carle
Reinhold
R
Schieber
Andreas
A
D000596:Amino Acids / Q000737:chemistry*; D016227:Benzoquinones / Q000737:chemistry*; D001628:Beverages / Q000032:analysis*; D002726:Chlorogenic Acid / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D005638:Fruit / Q000737:chemistry; D027845:Malus / Q000737:chemistry*; D010936:Plant Extracts / Q000737:chemistry*; D015203:Reproducibility of Results; D012680:Sensitivity and Specificity; D021241:Spectrometry, Mass, Electrospray Ionization / Q000379:methods*
D000596:Amino Acids; D016227:Benzoquinones; D010936:Plant Extracts; D002726:Chlorogenic Acid; C004532:quinone