Adducts Derived from (-)-Epigallocatechin gallate-Amadori Rearrangement Product in Aqueous Reaction System: Characterization, Formation and Thermolysis.

The interaction mechanism of (-)-epigallocatechin gallate (EGCG) with Amadori compound (Amadori rearrangement product, ARP) in xylose-alanine model reaction systems was investigated. The adducts between ARP and EGCG were identified as two ARP-EGCG isomers, two ARP-EGCG-H2O isomers, and multiple ARP-deoxypentosone (DP)-EGCG isomers. The structure of an isolated and purified ARP-EGCG adduct was analyzed by means of Fourier transform infrared spectroscopy, ultraviolet/visible spectroscopy, liquid chromatography-Timt-of-Flight (TOF)-mass spectrometry (LC-TOF-MS), and NMR. Using the two-dimensional NMR analyses, the structure of ARP-EGCG adduct was clarified to consist of a covalent linkage between the C12 position of the ARP and the C8 position of the A-ring of EGCG, presumably generated by the nucleophilic nature of the EGCG or aromatic substitution reactions. Results showed that slightly alkaline pH and the higher temperature could facilitate this reaction. Additionally, the thermal stability of ARP-EGCG and its degradation products revealed that the decomposition pathways of this adduct altered the classic decomposition pathway of ARP, resulting in a lower browning rate and blocking the subsequent Maillard reaction.

[1]  Chi-Tang Ho,et al.  Interaction of (-)-Epigallocatechin Gallate and deoxyosones blocking subsequent Maillard reaction and improving the yield of N-(1-deoxy-D-xylulos-1-yl)-alanine. , 2020, Journal of agricultural and food chemistry.

[2]  Chi-Tang Ho,et al.  Timely Addition of Glutathione for Its Interaction with Deoxypentosone To Inhibit the Aqueous Maillard Reaction and Browning of Glycylglycine-Arabinose System. , 2019, Journal of agricultural and food chemistry.

[3]  Chi-Tang Ho,et al.  Effective Mechanism of (-)-Epigallocatechin Gallate Indicating the Critical Formation Conditions of Amadori Compound during an Aqueous Maillard Reaction. , 2019, Journal of agricultural and food chemistry.

[4]  Chi-Tang Ho,et al.  Importance of the Nucleophilic Property of Tea Polyphenols. , 2018, Journal of agricultural and food chemistry.

[5]  Li Wang,et al.  Epicatechin Adducting with 5-Hydroxymethylfurfural as an Inhibitory Mechanism against Acrylamide Formation in Maillard Reactions. , 2018, Journal of agricultural and food chemistry.

[6]  T. Davidek,et al.  Preparation of activated flavor precursor DFG, N-(1-deoxy-1-fructosylglycine) by combination of vacuum evaporation and closed system heating steps. , 2018, Food chemistry.

[7]  T. Hofmann,et al.  Food-Grade Synthesis of Maillard-Type Taste Enhancers Using Natural Deep Eutectic Solvents (NADES) , 2018, Molecules.

[8]  A. Barrett,et al.  The Inhibition of Maillard Browning by Different Concentrations of Rosmarinic Acid and Epigallocatechin-3-Gallate in Model, Bakery, and Fruit Systems. , 2015, Journal of food science.

[9]  D. Peterson,et al.  Identification of bitter modulating maillard-catechin reaction products. , 2014, Journal of agricultural and food chemistry.

[10]  R. Elias,et al.  Influence of phenolic compounds on the mechanisms of pyrazinium radical generation in the Maillard reaction. , 2012, Journal of agricultural and food chemistry.

[11]  Chi-Tang Ho,et al.  Apple polyphenols, phloretin and phloridzin: new trapping agents of reactive dicarbonyl species. , 2008, Chemical research in toxicology.

[12]  Chi-Tang Ho,et al.  Tea polyphenol (-)-epigallocatechin-3-gallate: a new trapping agent of reactive dicarbonyl species. , 2007, Chemical research in toxicology.

[13]  D. Peterson,et al.  Influence of epicatechin reactions on the mechanisms of Maillard product formation in low moisture model systems. , 2007, Journal of agricultural and food chemistry.

[14]  D. Peterson,et al.  Epicatechin carbonyl-trapping reactions in aqueous maillard systems: Identification and structural elucidation. , 2006, Journal of agricultural and food chemistry.

[15]  Takashi Tanaka,et al.  A novel black tea pigment and two new oxidation products of epigallocatechin-3-O-gallate. , 2005, Journal of agricultural and food chemistry.

[16]  D. Peterson,et al.  Reactivity of epicatechin in aqueous glycine and glucose maillard reaction models: quenching of C2, C3, and C4 sugar fragments. , 2005, Journal of agricultural and food chemistry.

[17]  L. Fay,et al.  Study on the Formation and Decomposition of the Amadori Compound N-(1-Deoxy-D-Fructos-1-yl)-Glycine in Maillard Model Systems , 2005 .

[18]  T. Davidek,et al.  Degradation of the Amadori compound N-(1-deoxy-D-fructos-1-yl)glycine in aqueous model systems. , 2002, Journal of agricultural and food chemistry.

[19]  T. Hofmann,et al.  Studies on radical intermediates in the early stage of the nonenzymatic browning reaction of carbohydrates and amino acids. , 1999, Journal of agricultural and food chemistry.

[20]  T. Hofmann.  Identification of Novel Colored Compounds Containing Pyrrole and Pyrrolinone Structures Formed by Maillard Reactions of Pentoses and Primary Amino Acids , 1998 .

[21]  Yu Huang,et al.  Stability of Green Tea Catechins , 1997 .

[22]  A. Davis,et al.  1H and 13C NMR Assignments of Some Green Tea Polyphenols , 1996 .

[23]  M. Feather,et al.  Chemistry of Amadori rearrangement products: analysis, synthesis, kinetics, reactions, and spectroscopic properties. , 1994, Critical reviews in food science and nutrition.

[24]  J. Hodge,et al.  Amadori compounds as nonvolatile flavor precursors in processed foods , 1969 .

[25]  J. Hodge,et al.  The Amadori rearrangement. , 1955, Advances in carbohydrate chemistry.

[26]  J. Hodge.  Dehydrated Foods, Chemistry of Browning Reactions in Model Systems , 1953 .

[27]  J. Hodge,et al.  The Amadori Rearrangement under New Conditions and its Significance for Non-enzymatic Browning Reactions2 , 1953 .