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A DFT and PM6 study of free radical scavenging activity of ellagic acid

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Abstract

Reaction enthalpies related to mechanisms of free radical scavenging activity of ellagic acid and its phenoxide anions were calculated by density functional theory and the semiempirical PM6 method. In addition to the gas phase, calculations are performed for water and benzene as the solvents, which may represent biological liquids and the membrane lipids, i.e., a natural environment for antiradical action. The thermodynamically favored mechanism depends on the polarity of reaction media, deprotonation degree of ellagic acid as well as the properties of scavenging radicals. The most acidic 3-OH group of ellagic acid is the active site for radical inactivation. The ellagate monoanions and dianions possess progressively better scavenging potency than unionized ellagic acid. The sequential proton loss electron transfer mechanism is the preferred reaction pathway for the ellagate monoanion and dianion in water. In benzene, ellagic acid inactivates free radicals by the hydrogen atom transfer mechanism. In the gas phase the latter mechanism is favored for all ellagic acid species.

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Acknowledgments

This study is cofinanced by the Ministry of Science of the Republic of Serbia (Project No. 172015 and Serbia-Croatia Bilateral Agreement 2011-2012) as well as by the Ministry of Science, Education, and Sports of the Republic of Croatia (Projects Nos. 079-0000000-3211, 098-1770495-2919, and Croatia-Serbia Bilateral Agreement 2011-2012).

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Authors and Affiliations

  1. Department of Chemical-Technological Sciences, State University of Novi Pazar, Vuka Karadžića bb, 36300, Novi Pazar, Republic of Serbia

    Zoran Marković

  2. Bioengineering Research and Development Center, 34000, Kragujevac, Republic of Serbia

    Dejan Milenković & Jelena Đorović

  3. Faculty of Physical Chemistry, University of Belgrade, Studentski Trg 12-16, 11000, Belgrade, Republic of Serbia

    Jasmina M. Dimitrić Marković

  4. Faculty of Agriculture, The Josip Juraj Strossmayer University, P.O. Box 719, HR-31107, Osijek, Croatia

    Dragan Amić

  5. NMR Center, Rudjer Bošković Institute, P.O. Box 180, HR-10002, Zagreb, Croatia

    Bono Lučić

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  1. Zoran Marković
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  2. Dejan Milenković
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  3. Jelena Đorović
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  4. Jasmina M. Dimitrić Marković
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  5. Bono Lučić
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  6. Dragan Amić
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Correspondence to Zoran Marković or Dragan Amić.

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Marković, Z., Milenković, D., Đorović, J. et al. A DFT and PM6 study of free radical scavenging activity of ellagic acid. Monatsh Chem 144, 803–812 (2013). https://doi.org/10.1007/s00706-013-0949-z

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  • DOI: https://doi.org/10.1007/s00706-013-0949-z

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