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Comprehensive Investigation of the Antioxidant and Pro-oxidant Effects of Phenolic Compounds: A Double-Edged Sword in the Context of Oxidative Stress? | LitMetric

Comprehensive Investigation of the Antioxidant and Pro-oxidant Effects of Phenolic Compounds: A Double-Edged Sword in the Context of Oxidative Stress?

J Phys Chem B

Departamento de Química , Universidad Autónoma Metropolitana-Iztapalapa , San Rafael Atlixco 186 , Col. Vicentina, Iztapalapa , C.P. 09340 México City , México.

Published: June 2018

AI Article Synopsis

  • * The study highlights that factors like redox metals, pH levels, and the transformation of PhCs into benzoquinones significantly influence whether they behave as antioxidants or pro-oxidants.
  • * Despite the potential risks associated with PhCs acting as pro-oxidants, their benefits as antioxidants typically outweigh these risks, suggesting the need for careful considerations when using them in strategies against OS.

Article Abstract

Oxidative stress (OS) is a health-threatening process that is involved, at least partially, in the development of several diseases. Although antioxidants can be used as a chemical defense against OS, they might also exhibit pro-oxidant effects, depending on environmental conditions. In this work, such a dual behavior was investigated for phenolic compounds (PhCs) within the framework of the density functional theory and based on kinetic data. Multiple reaction mechanisms were considered in both cases. The presence of redox metals, the pH, and the possibility that PhCs might be transformed into benzoquinones were identified as key aspects in the antioxidant versus pro-oxidant effects of these compounds. The main virtues of PhCs as antioxidants are their radical trapping activity, their regeneration under physiological conditions, and their behavior as OH-inactivating ligands. The main risks of PhCs as pro-oxidants are predicted to be the role of phenolate ions in the reduction of metal ions, which can promote Fenton-like reactions, and the formation of benzoquinones that might cause protein arylation at cysteine sites. Although the benefits seem to overcome the hazards, to properly design chemical strategies against OS using PhCs, it is highly recommended to carefully explore their duality in this context.

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Source
http://dx.doi.org/10.1021/acs.jpcb.8b03500DOI Listing

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