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[Computational study on antioxidation mechanism of catechins].

M Kurihara1, K Kondo, K Fukuhara

  • 1masaaki@nihs.go.jp

Kokuritsu Iyakuhin Shokuhin Eisei Kenkyujo Hokoku = Bulletin of National Institute of Health Sciences
|August 12, 2000
PubMed
Summary

The antioxidative activity of catechins is linked to the low bond dissociation enthalpies of benzyl hydrogens. This finding highlights the critical role of benzyl hydrogen abstraction in the antioxidant mechanism of catechins.

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Area of Science:

  • Computational Chemistry
  • Biochemistry
  • Antioxidant Research

Background:

  • Catechins are known for their potent antioxidant properties.
  • The precise molecular mechanisms underlying their antioxidant activity require further elucidation.

Purpose of the Study:

  • To calculate the bond dissociation enthalpies (BDEs) of C-H and O-H bonds in catechins.
  • To identify the key reactive sites responsible for the antioxidant activity of catechins.

Main Methods:

  • Semi-empirical molecular orbital calculations using the SPARTAN program.
  • Analysis of reaction intermediates using Liquid Chromatography-Mass Spectrometry (LC/MS) and spectrophotometric methods.

Main Results:

  • Calculations revealed significantly low BDEs for benzyl hydrogens at the C-2 position in catechins.

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  • Experimental data corroborated the theoretical findings, supporting the role of benzyl hydrogen abstraction.

    • Conclusions:

    • The low BDE of benzyl hydrogens is crucial for the antioxidative activity of catechins.
    • Benzyl hydrogen abstraction is a key step in the antioxidant mechanism of catechins.