Formation of strecker aldehydes from polyphenol-derived quinones and alpha-amino acids in a nonenzymic model system

Journal of Agricultural and Food Chemistry
George P Rizzi

Abstract

Fruits and vegetables contain naturally occurring polyphenolic compounds that can undergo enzyme-catalyzed oxidation during food preparation. Many of these compounds contain catechol (1,2-dihydroxybenzene) moieties that may be transformed into o-quinone derivatives by polyphenoloxidases and molecular oxygen. Secondary reactions of the o-quinones include the Strecker degradation of ambient amino acids to form flavor-important volatile aldehydes. The purpose of this work was to investigate the mechanism of the polyphenol/o-quinone/Strecker degradation sequence in a nonenzymic model system. By using ferricyanide ion as the oxidant in pH 7.17 phosphate buffer at 22 degrees C, caffeic acid, chlorogenic acid, (+) catechin, and (-) epicatechin were caused to react with methionine and phenylalanine to produce Strecker aldehydes methional and phenylacetaldehyde in 0.032-0.42% molar yields (0.7-10 ppm in reaction mixtures). Also, by employing l-proline methyl ester in a reaction with 4-methylcatechol, a key reaction intermediate, 4-(2'-carbomethoxy-1'-pyrrolidinyl)-5-methyl-1,2-benzoquinone (7), was isolated and tentatively identified.

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Citations

Aug 7, 2012·Journal of Agricultural and Food Chemistry·Maria Nikolantonaki, Andrew L Waterhouse
Jun 4, 2013·Journal of Agricultural and Food Chemistry·Maurizio Ugliano
Feb 18, 2010·International Journal of Molecular Sciences·Takashi TanakaIsao Kouno
Sep 1, 2012·Journal of the Science of Food and Agriculture·Ola Lasekan
Dec 30, 2014·Journal of Agricultural and Food Chemistry·Rosa M DelgadoFrancisco J Hidalgo
Dec 4, 2013·Food Additives & Contaminants. Part A, Chemistry, Analysis, Control, Exposure & Risk Assessment·Antonio Higinio SánchezAlfredo Montaño
Jun 11, 2016·Food Chemistry·Carla M OliveiraArtur M S Silva
Oct 7, 2014·Journal of Agricultural and Food Chemistry·Vicente FerreiraPurificación Fernández-Zurbano
Oct 11, 2016·Journal of Agricultural and Food Chemistry·Philip C WietstockFrank-Jürgen Methner
Feb 28, 2017·Journal of Agricultural and Food Chemistry·Ana Rita MonforteAntonio C Silva Ferreira
May 24, 2017·Journal of Agricultural and Food Chemistry·Marianne N Lund, Colin A Ray
Feb 17, 2018·Critical Reviews in Food Science and Nutrition·Gal Y KreitmanGavin L Sacks
Mar 2, 2018·Frontiers in Chemistry·Mónica BuenoVicente Ferreira
Sep 27, 2019·Food Research International·Antonio López-LópezAlfredo Montaño
Jul 1, 2016·Comprehensive Reviews in Food Science and Food Safety·Paulo R A B ToledoAline T Toci
Jan 1, 2017·Comprehensive Reviews in Food Science and Food Safety·Javier García-Lomillo, María Luisa González-SanJosé
Jul 6, 2019·Journal of Agricultural and Food Chemistry·A R MonforteA C Silva Ferreira
Nov 27, 2018·Journal of Agricultural and Food Chemistry·Andreas Schieber

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