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A quantum chemical study on the free radical scavenging activity of tyrosol and hydroxytyrosol

Abstract

The free radical scavenging activity of hydroxytyrosol (HTyr) and tyrosol (Tyr) has been studied in aqueous and lipid solutions, using the density functional theory. Four mechanisms of reaction have been considered: single electron transfer (SET), sequential electron proton transfer (SEPT), hydrogen transfer (HT), and radical adduct formation. It was found that while SET and SEPT do not contribute to the overall reactivity of HTyr and Tyr toward ·OOH and ·OCH3 radicals, they can be important for their reactions with ·OH, ·OCCl3, and ·OOCCl3. The ·OOH-scavenging activity of HTyr and Tyr was found to take place exclusively by HT, and it is also predicted to be the main mechanism for their reactions with ·OCH3. HT is proposed as the main mechanism for the scavenging activity of HTyr and Tyr when reacting with other ·OR and ·OOR radicals, provided that R is an alkyl or an alkenyl group. The major products of reaction are predicted to be the phenoxyl radicals. In addition, Tyr was found to be less efficient than HTyr as free radical scavenger. Moreover, while HTyr is predicted to be a good peroxyl scavenger, Tyr is predicted to be only moderately for that purpose.

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Acknowledgments

We gratefully acknowledge the Laboratorio de Visualización y Cómputo Paralelo at Universidad Autónoma Metropolitana-Iztapalapa and Dirección General de Cómputo y de Tecnologías de Información y Comunicación (DGCTIC) at Universidad Nacional Autónoma de México. M. E. M. thanks CONACYT for postdoctoral fellowship No. 48363. This work was partially supported by a grant from the DGAPA UNAM (PAPIIT-IN209812), and projects SEP-CONACyT 167491 and 167430.

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Correspondence to Annia Galano or Juan Raúl Alvarez-Idaboy.

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Galano, A., Alvarez-Idaboy, J.R., Francisco-Márquez, M. et al. A quantum chemical study on the free radical scavenging activity of tyrosol and hydroxytyrosol. Theor Chem Acc 131, 1173 (2012). https://doi.org/10.1007/s00214-012-1173-3

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Keywords

  • Rate constant
  • Mechanism of reaction
  • Branching ratios
  • UV-vis spectra