Covalent Binding of Tea Catechins to Protein Thiols: The Relationship between Stability and Electrophilic Reactivity

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  • MORI Taiki
    Department of Food and Nutritional Sciences, and Global Center of Excellence (COE) Program, University of Shizuoka
  • ISHII Takeshi
    Department of Food and Nutritional Sciences, and Global Center of Excellence (COE) Program, University of Shizuoka
  • AKAGAWA Mitsugu
    Department of Biological Chemistry, Division of Applied Life Science, Graduate School of Life and Environmental Sciences, Osaka Prefecture University
  • NAKAMURA Yoshimasa
    Department of Biofunctional Chemistry, Division of Bioscience, Graduate School of Natural Science and Technology, Okayama University
  • NAKAYAMA Tsutomu
    Department of Food and Nutritional Sciences, and Global Center of Excellence (COE) Program, University of Shizuoka

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In this study, we investigated the relationship between the stability of catechins and their electrophilic reactivity with proteins. The stability of catechins was evaluated by HPLC analysis. Catechol-type catechins were stable in a neutral buffer, but pyrogallol-type catechins, such as (−)-epigallocatechin gallate (EGCg), were unstable. The electrophilic reactivity of catechins with thiol groups in a model peptide and a protein was confirmed by both mass spectrometry and electrophoresis/blotting with redox-cycling staining. In a comparison of several catechins, pyrogallol-type catechins had higher reactivity with protein thiols than catechol-type catechins. The instability and reactivity of EGCg were enhanced in an alkaline pH buffer. The reactivity of EGCg was reduced by antioxidants due to their ability to prevent EGCg autoxidation. These results indicate that the instability against oxidation of catechins is profoundly related to their electrophilic reactivity. Consequently, the difference in these properties of tea catechins can contribute to the magnitude of their biological activities.

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