Probing the antioxidant potential of phloretin and phlorizin through a computational investigation

  • Rodrigo A. Mendes
  • Bruno L. S. e Silva
  • Renata Takeara
  • Renato G. Freitas
  • Alex Brown
  • Gabriel L. C. de Souza
Original Paper
  • 95 Downloads

Abstract

The structures and energetics of two dihydrochalcones (phloretin and its glycoside phlorizin) were examined with density functional theory, using the B3LYP, M06-2X, and LC-ω PBE functionals with both the 6-311G(d,p) and 6-311 + G(d,p) basis sets. Properties connected to antioxidant activity, i.e., bond dissociation enthalpies (BDEs) for OH groups and ionization potentials (IPs), were computed in a variety of environments including the gas-phase, n-hexane, ethanol, methanol, and water. The smallest BDEs among the four OH groups for phloretin (three for phlorizin) were determined (using B3LYP/6-311 + G(d,p) in water) to be 79.36 kcal/mol for phloretin and 79.98 kcal/mol for phlorizin while the IPs (at the same level of theory) were obtained as 139.48 and 138.98 kcal/mol, respectively. By comparing with known antioxidants, these values for the BDEs indicate both phloretin and phlorizin show promise for antioxidant activity. In addition, the presence of the sugar moiety has a moderate (0-6 kcal/mol depending on functional) effect on the BDEs for all OH groups. Interestingly, the BDEs suggest that (depending on the functional chosen) the sugar moiety can lead to an increase, decrease, or no change in the antioxidant activity. Therefore, further experimental tests are encouraged to understand the substituent effect on the BDEs for phloretin and to help determine the most appropriate functional to probe BDEs for dihydrochalcones.

Keywords

Dihydrochalcones Phloretin Phlorizin Bond dissociation energy (BDE) Ionization potential (IP) Density functional theory (DFT) Antioxidant activity 

Notes

Acknowledgments

GLCS thanks Dr. Mariana Pantoja, MD from the Universidade do Estado do Amazonas for useful discussions. This work was partially funded by the Brazilian agency CNPq (Process number: 306266/2016-4). AB thanks the Natural Sciences and Engineering Research Council of Canada for funding (NSERC - Discovery Grant).

Supplementary material

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Authors and Affiliations

  1. 1.Departamento de QuímicaUniversidade Federal de Mato GrossoCuiabáBrazil
  2. 2.Instituto de Ciências Exatas e TecnologiaUniversidade Federal do AmazonasItacoatiaraBrazil
  3. 3.Department of ChemistryUniversity of AlbertaEdmontonCanada

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