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Exploring antioxidant reactivity and molecular structure of phenols by means of two coupled assays using fluorescence probe (2,3-diazabicyclo[2.2.2]oct-2-ene, DBO) and free radical (2,2-diphenyl-1-picrylhydrazyl, \(\hbox {DPPH}^{\cdot }\))

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Abstract

Phenolic compounds can be considered as the most important bioactive compounds in Mediterranean diet. However, many of the complex connections between phenols antioxidant reactivity and their molecular structure remain unsolved. To shine light on these issues, the antioxidant reactivity of 15 relevant phenolic compounds was studied. Two different analytical approaches were combined: (a) the well-established 2,2-diphenyl-1-picrylhydrazyl \((\hbox {DPPH}^{\cdot }\)) stable free radical assay, and (b) the 2,3-diazabicyclo[2.2.2]oct-2-ene (DBO) fluorescent probe assay. The results obtained confirm how certain structural features (i.e., hydroxyl and methoxy groups, alkyl and alkenyl chains) play a critical role in the singular antioxidant response exhibited by each phenolic compound. This knowledge provides decisive information to select a specific phenolic compound as an antioxidant additive or for the chemical design of new antioxidants.

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Synopsis (for Contents page): Interactions between DBO (fluorescence quenching) and DPPH (radical scavenging) with fifteen phenolic compounds, which are present in olive oil and wine, served as a measure of antioxidant activity of the phenols and correlated to the molecular structure.

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Acknowledgements

We are grateful to Prof. W. M. Naufrom Jaccobs University of Bremen (Germany) for kindly providing the DBO fluorophore used in this study, and to Prof. J. L. Espartero from University of Seville (Spain) for kindly providing the hydroxytyrosol. We are also indebted to Prof. M. A. Caraballo and Prof. P. Richter from University of Chile (Chile) and Prof. U. Pischel from University of Huelva (Spain) for helpful comments and discussions. This study was funded by the Environmental Council of the Andalusia Regional Government through project P10 FQM 6185 and by the Operative Program of Transborderline Cooperation Spain-Portugal through project 0434_I2TEP_5_E OLITRACE and by FONDECYT (Postdoctoral Grant 3150059).

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Authors and Affiliations

  1. Department of Chemistry and Material Sciences, Area of Analytical Chemistry, Faculty of Experimental Sciences, University of Huelva, Agrifood Campus of International Excellence, ceiA3. Avd. Tres de Marzo S/N, 21007, Huelva, Spain

    MERCEDES BECERRA-HERRERA, ANA SAYAGO & RAFAEL BELTRÁN

  2. Department of Inorganic and Analytical Chemistry, Faculty of Chemical and Pharmaceutical Sciences, University of Chile, P.O. Box 233, Santiago, Chile

    MERCEDES BECERRA-HERRERA

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  1. MERCEDES BECERRA-HERRERA
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Correspondence to MERCEDES BECERRA-HERRERA.

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BECERRA-HERRERA, M., SAYAGO, A. & BELTRÁN, R. Exploring antioxidant reactivity and molecular structure of phenols by means of two coupled assays using fluorescence probe (2,3-diazabicyclo[2.2.2]oct-2-ene, DBO) and free radical (2,2-diphenyl-1-picrylhydrazyl, \(\hbox {DPPH}^{\cdot }\)). J Chem Sci 129, 1381–1390 (2017). https://doi.org/10.1007/s12039-017-1331-1

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