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

Research output: Contribution to journalArticle

1 Citation (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 languageEnglish
Pages (from-to)1847-1851
Number of pages5
JournalEuropean Journal of Nutrition
Volume58
Issue number5
Early online date28 May 2018
DOIs
Publication statusE-pub ahead of print - 28 May 2018

Fingerprint

Liver Microsomes
Selenium
Vitamin E
Sulfur
Lipid Peroxidation
Antioxidants
Phenol
Thiourea
Phenols
Olea
Microsomes
Molecular Structure
Sulfhydryl Compounds
Disulfides
3,4-dihydroxyphenylethanol
Diet

Keywords

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

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; Maya, Inés; Fernández-Bolaños, Juan; Duthie, Garry G; de Roos, Baukje.

In: European Journal of Nutrition, Vol. 58, No. 5, 08.2019, p. 1847-1851.

Research output: Contribution to journalArticle

Rodríguez-Gutiérrez, Guillermo ; Rubio-Senent, Fátima ; Gómez-Carretero, Antonio ; Maya, Inés ; Fernández-Bolaños, Juan ; Duthie, Garry G ; de Roos, Baukje. / Selenium and sulphur derivatives of hydroxytyrosol : inhibition of lipid peroxidation in liver microsomes of vitamin E-deficient rats. In: European Journal of Nutrition. 2019 ; Vol. 58, No. 5. pp. 1847-1851.
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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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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 “Ram{\'o}n y Cajal” Program (RYC-2012-10456 contract), co-funded by the ESF.",
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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 - 2018/5/28

Y1 - 2018/5/28

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

VL - 58

SP - 1847

EP - 1851

JO - European Journal of Nutrition

JF - European Journal of Nutrition

SN - 1436-6207

IS - 5

ER -