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

The Journal of Physical Chemistry. B
Romina Castañeda-ArriagaAnnia Galano

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 PhC...Continue Reading

References

Mar 1, 1997·Experimental Physiology·H Sies
Jan 8, 1998·Nutrition Reviews·E A Decker
Sep 6, 2000·European Journal of Biochemistry·B Moosmann, C Behl
Jun 4, 2002·DNA and Cell Biology·Aubrey D N J De Grey
Dec 7, 2007·Chemical Research in Toxicology·Lawrence M SayreMark A Smith
Aug 1, 2008·Accounts of Chemical Research·Jean CadetJean-Luc Ravanat
Feb 3, 2009·Free Radical Biology & Medicine·Anastasia S DomazouJanusz M Gebicki
Jul 28, 2009·Journal of the American Chemical Society·Zachary I Watts, Christopher J Easton
Aug 7, 2009·The Journal of Physical Chemistry. a·Vyacheslav S BryantsevWilliam A Goddard
Aug 12, 2009·Journal of Molecular Modeling·Thekinneydath Rajan Heera, Louis Cindrella
Apr 8, 2010·The Journal of Physical Chemistry. a·Hoang Q DoanJoseph S Francisco
Jun 10, 2010·Amino Acids·Janusz M GebickiWillem H Koppenol
May 24, 2011·Toxicology in Vitro : an International Journal Published in Association with BIBRA·Yusuke IwasakiHiroyuki Nakazawa
Jul 15, 2011·Journal of Pineal Research·Annia GalanoRussel J Reiter
Aug 31, 2011·The Journal of Physical Chemistry. B·Raphael F RibeiroDonald G Truhlar
Sep 29, 2011·Journal of the American Chemical Society·Robert J O'ReillyLeo Radom
Mar 9, 2012·Physical Chemistry Chemical Physics : PCCP·Monika DargiewiczVincenzo Barone
Jun 16, 2012·Oxidative Medicine and Cellular Longevity·Catarina PimentelRegina A Menezes
Jun 20, 2012·Biochemistry·Gözde Eskici, Paul H Axelsen
Oct 16, 2012·The Journal of Organic Chemistry·Bun ChanLeo Radom
Oct 19, 2012·Journal of Alzheimer's Disease : JAD·Natividad LópezJordi Alom
Dec 4, 2012·Free Radical Biology & Medicine·Michael H YanXiongwei Zhu
Mar 29, 2013·Chemistry : a European Journal·J I MujikaJ M Matxain
Apr 10, 2013·Current Pharmaceutical Design·Corina Şerban, Simona Drăgan
Apr 13, 2013·Environmental Science & Technology·Mohammednoor Altarawneh, Bogdan Z Dlugogorski
Jun 26, 2013·Free Radical Biology & Medicine·Anna ZampetakiManuel Mayr
Jul 10, 2013·Current Medicinal Chemistry·Betul Tekiner-GulbasSibel Suzen
Sep 13, 2013·Reviews in Endocrine & Metabolic Disorders·Morihiro Matsuda, Iichiro Shimomura
Sep 26, 2013·Current Medicinal Chemistry·Miroslav Pohanka
Sep 26, 2013·The Journal of Physical Chemistry. B·Ruslán Álvarez-DidukArben Merkoçi

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Citations

Sep 14, 2019·International Journal of Molecular Sciences·Yang-Hsiang Lin
May 28, 2019·Journal of Computational Chemistry·Mirzam Carreon-GonzalezJuan Raul Alvarez-Idaboy
Aug 23, 2020·Antioxidants·Guillermo García-Díez, Nelaine Mora-Diez
Apr 30, 2020·Antioxidants·Isabella RomeoTiziana Marino
Dec 26, 2018·Food Chemistry·Jelena Tošović, Svetlana Marković
Sep 10, 2021·Cell Biochemistry and Function·Vinay Bharadwaj Tatipamula, Biljana Kukavica
Sep 15, 2021·The Journal of Organic Chemistry·Timofey D MoseevOleg N Chupakhin
Jan 8, 2022·Journal of Biomaterials Applications·Andrew Baldwin, Brian W Booth

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