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Hydroxytyrosol Acyl Esters: Biosynthesis and Activities

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Abstract

We previously reported the production of high yields of hydroxytyrosol through the bioconversion of tyrosol. In the present work, hydroxytyrosol was subjected to the lipase catalyzed acylation aiming for the recovery of more lipophilic esters that might be easily incorporated in cosmetic and food preparations. Hydroxytyrosyl acetate and hydroxytyrosyl oleate were produced with respective molar esterification yields of 98% and 78%. DPPH free radical quenching potency demonstrated that the acylation of hydroxytyrosol did not alter its antioxidant activity. The acylated esters were shown to be more effective than the natural antioxidant: caffeic acid and two synthetic ones as BHA and BHT. Antiproliferative activity on human cervical cells (HeLa) resulted in IC50 values of 0.46, 0.42 and 0.33 mM for hydroxytyrosol and its acetyl and oleyl esters, respectively. Additionally, when used at a non-cytotoxic concentration (100 μM), these compounds showed significant effectiveness in preventing iron-induced oxidative stress, resulting in a reduction of 30%, 36% and 38% in thiobarbituric acid-reactive substance production, respectively.

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Abbreviations

BHA:

Butylated hydroxyanisole

BHT:

Butylated hydroxytoluene

DPPH:

2,2-Diphenyl-1-picrylhydrazyl

MTT:

3-(4,5-Dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide

TBARS:

Thiobarbituric acid-reactive substances

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Acknowledgements

The authors would like to thank Dr. Tom C. Arnot for the manuscript revision, Mr. Adel Gargoubi for his assistance for the HPLC analyses and the purification of hydroxytyrosol esters and Mrs. Emna Debbebi for the NMR analysis.

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Authors and Affiliations

  1. Environnemental Bioprocesses Laboratory, Sfax Biotechnology Centre, P.O. Box 1177, 3038, Sfax, Tunisia

    Zouhaier Bouallagui, Mohamed Bouaziz & Sami Sayadi

  2. Unite de Biotechnologie et Pathologie, Higher Institute of Biotechnology of Sfax, University of Sfax, P.O. Box “261”, 3038, Sfax, Tunisia

    Salwa Lassoued

  3. Laboratoire d’ingénierie des biomolécules, ENSAIA-National Polytechnic Institute of Lorraine, 2, Av de la Forêt de Haye, 54500, Vandoeuvre, France

    Jean Marc Engasser & Mohamed Ghoul

Authors
  1. Zouhaier Bouallagui
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  2. Mohamed Bouaziz
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  3. Salwa Lassoued
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  4. Jean Marc Engasser
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  5. Mohamed Ghoul
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  6. Sami Sayadi
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Correspondence to Sami Sayadi.

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Bouallagui, Z., Bouaziz, M., Lassoued, S. et al. Hydroxytyrosol Acyl Esters: Biosynthesis and Activities. Appl Biochem Biotechnol 163, 592–599 (2011). https://doi.org/10.1007/s12010-010-9065-2

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  • DOI: https://doi.org/10.1007/s12010-010-9065-2

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