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Selenium and sulphur derivatives of hydroxytyrosol: inhibition of lipid peroxidation in liver microsomes of vitamin E-deficient rats

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Abstract

Purpose

The objective of this study was to evaluate the capacity of modified phenols synthesized from hydroxytyrosol, a natural olive oil phenol, specifically those containing a selenium or sulphur group, to inhibit lipid peroxidation.

Methods

The compounds’ abilities to inhibit lipid peroxidation in liver microsomes obtained from vitamin E-deficient rats were compared to hydroxytyrosol.

Results

All synthetic compounds had a significant higher ability to inhibit lipid peroxidation than hydroxytyrosol. Selenium derivates displayed a higher antioxidant activity than sulphur derivatives. In addition, the antioxidant activity increased with a higher number of heteroatoms in the hydroxytyrosol molecular structure.

Conclusion

The study shows, for the first time, the ability of synthetic compounds, derived from the most active phenol present in olives in free form (hydroxytyrosol), and containing one or two atoms of sulphur or selenium, to inhibit the lipid peroxidation of vitamin E-deficient microsomes. The antioxidant activity of five thioureas, a disulfide, a thiol, three selenoureas, a diselenide, and a selenonium were evaluated and the results showed a higher inhibition of lipid peroxidation than the natural phenol. Selenium and sulphur derivatives of hydroxytyrosol are novel antioxidants with the potential to supplement the lack of vitamin E in the diet as natural alternatives for the prevention of diseases related to oxidative damage.

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Acknowledgements

The research of BDR and GD is funded by the Scottish Government’s Rural and Environment Science and Analytical Services (RESAS) division. This research was funded by the Spanish Ministry of Economy and Competitiveness and co-funded by the European Social Fund (ESF) (Project AGL2016-79088R). GRG wishes to thank the “Ramón y Cajal” Program (RYC-2012-10456 contract), co-funded by the ESF.

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Authors and Affiliations

  1. Food Phytochemistry Department, Instituto de la Grasa, Consejo Superior de Investigaciones Científicas (CSIC), Campus Universitario Pablo de Olavide, Edificio 46, Ctra. de Utrera, km. 1, 41013, Seville, Spain

    Guillermo Rodríguez-Gutiérrez, Fátima Rubio-Senent, Antonio Gómez-Carretero & Juan Fernández-Bolaños

  2. Departamento de Química Orgánica, Facultad de Química, Universidad de Sevilla, Apartado 1203, 41071, Seville, Spain

    Antonio Gómez-Carretero & Inés Maya

  3. Rowett Institute of Nutrition and Health, University of Aberdeen, Foresterhill, Aberdeen, AB25 2ZD, UK

    Garry G. Duthie & Baukje de Roos

Authors
  1. Guillermo Rodríguez-Gutiérrez
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  2. Fátima Rubio-Senent
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  3. Antonio Gómez-Carretero
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  4. Inés Maya
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  5. Juan Fernández-Bolaños
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  6. Garry G. Duthie
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  7. Baukje de Roos
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Corresponding author

Correspondence to Guillermo Rodríguez-Gutiérrez.

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Rodríguez-Gutiérrez, G., Rubio-Senent, F., Gómez-Carretero, A. et al. Selenium and sulphur derivatives of hydroxytyrosol: inhibition of lipid peroxidation in liver microsomes of vitamin E-deficient rats. Eur J Nutr 58, 1847–1851 (2019). https://doi.org/10.1007/s00394-018-1733-y

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  • DOI: https://doi.org/10.1007/s00394-018-1733-y

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