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

Guillermo Rodríguez-Gutiérrez; Fátima Rubio-Senent; Antonio Gómez-Carretero; Inés Maya; Juan Fernández-Bolaños; Garry G Duthie; Baukje de Roos

doi:10.1007/s00394-018-1733-y

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

Guillermo Rodríguez-Gutiérrez^* (Corresponding Author), Fátima Rubio-Senent, Antonio Gómez-Carretero, Inés Maya, Juan Fernández-Bolaños, Garry G Duthie, Baukje de Roos

^*Corresponding author for this work

The Rowett Institute of Nutrition and Health

Research output: Contribution to journal › Article › peer-review

6 Citations (Scopus)

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.

Original language	English
Pages (from-to)	1847-1851
Number of pages	5
Journal	European Journal of Nutrition
Volume	58
Issue number	5
Early online date	28 May 2018
DOIs	https://doi.org/10.1007/s00394-018-1733-y
Publication status	Published - Aug 2019

Bibliographical note

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.

Keywords

Journal Article
antioxidant
hydroxytyrosol
selenium
sulphur
lipid peroxidation
Vitamin E
Microsomes
Mediterranean diet

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10.1007/s00394-018-1733-yLicence: Unspecified

Baukje de Roos
- School of Medicine, Medical Sciences & Nutrition, The Rowett Institute of Nutrition and Health - Personal Chair
Person: Academic

Cite this

Selenium and sulphur derivatives of hydroxytyrosol: inhibition of lipid peroxidation in liver microsomes of vitamin E-deficient rats. / Rodríguez-Gutiérrez, Guillermo (Corresponding Author); Rubio-Senent, Fátima; Gómez-Carretero, Antonio et al.
In: European Journal of Nutrition, Vol. 58, No. 5, 08.2019, p. 1847-1851.

Research output: Contribution to journal › Article › peer-review

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

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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author = "Guillermo Rodr{\'i}guez-Guti{\'e}rrez and F{\'a}tima Rubio-Senent and Antonio G{\'o}mez-Carretero and In{\'e}s Maya and Juan Fern{\'a}ndez-Bola{\~n}os and Duthie, {Garry G} and {de Roos}, Baukje",

note = "Acknowledgements: The research of BDR and GD is funded by the Scottish Government{\textquoteright}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 “Ram{\'o}n y Cajal” Program (RYC-2012-10456 contract), co-funded by the ESF.",

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doi = "10.1007/s00394-018-1733-y",

language = "English",

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pages = "1847--1851",

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T1 - Selenium and sulphur derivatives of hydroxytyrosol

T2 - inhibition of lipid peroxidation in liver microsomes of vitamin E-deficient rats

AU - Rodríguez-Gutiérrez, Guillermo

AU - Rubio-Senent, Fátima

AU - Gómez-Carretero, Antonio

AU - Maya, Inés

AU - Fernández-Bolaños, Juan

AU - Duthie, Garry G

AU - de Roos, Baukje

N1 - 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.

PY - 2019/8

Y1 - 2019/8

N2 - 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.

AB - 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.

KW - Journal Article

KW - antioxidant

KW - hydroxytyrosol

KW - selenium

KW - sulphur

KW - lipid peroxidation

KW - Vitamin E

KW - Microsomes

KW - Mediterranean diet

U2 - 10.1007/s00394-018-1733-y

DO - 10.1007/s00394-018-1733-y

M3 - Article

C2 - 29808273

SN - 1436-6207

VL - 58

SP - 1847

EP - 1851

JO - European Journal of Nutrition

JF - European Journal of Nutrition

IS - 5

ER -

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

Abstract

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Keywords

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