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Antioxidant and antimalarial properties of butein and homobutein based on their ability to chelate iron (II and III) cations: a DFT study in vacuo and in solution

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Abstract

A theoretical study on the antioxidant and antimalarial properties of butein and homobutein has been performed by considering their Fe2+ and Fe3+ chelation ability. In order to elucidate the origin of the antioxidant and antimalarial properties of these compounds, the study attempts to investigate the nature of the complex structures, ligand···Fen+ stabilities and electronic properties of the Fe cations before and after complexation. The investigation considered the neutral and the deprotonated species of butein and homobutein interacting with the Fe cations as well as the deprotonated species of butein and homobutein interacting with micro-solvated Fe2+ or Fe3+ cation. The study has been performed using B3LYP/6-31+G(d,p) method. The LANL2DZ pseudo-potential was selected to describe the Fe cations. Final energies were obtained using the B3LYP/6-311+G(2d,p)//B3LYP/6-31+G(d,p) method. The binding energies depend on the media (it is higher in vacuo than in water solution), the nature of the cation (it is higher for Fe3+ than for Fe2+), the nature of the ligand and the Fen+ coordination site on the ligand (it is highest for the bidentate Fe coordination to O2′ and O9 atoms and lowest for the Fe coordination on the π system of the aromatic ring). The charge on Fen+ decreases on coordination to the ligand. AIM analysis suggests that the strong cation···ligand interactions are more likely covalent than ionic in vacuo and entirely ionic in solution. The ability of the ligands to reduce the Fe cation coupled with the strong iron-binding properties has significant implication on their antioxidant and antimalarial activities.

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Acknowledgments

Kemoabetswe R.N. Serobatse is grateful to Sasol Inzalo Foundation (South Africa) for financial assistance which has enabled her to take part in this work. The financial assistance of the South African National Research Foundation (NRF) towards this research, in support of K.R.N. Serobatse, is hereby acknowledged. Opinions expressed and conclusions arrived at are those of the authors and are not necessarily to be attributed to the NRF or Sasol Inzalo Foundation.

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  1. Department of Chemistry, Faculty of Agriculture, Science and Technology, School of Mathematical and Physical Science, North-West University (Mafikeng Campus), Private Bag X2046, Mmabatho, 2735, South Africa

    Kemoabetswe R. N. Serobatse & Mwadham M. Kabanda

  2. Material Science Innovation and Modelling (MaSIM) Research Focus Area, Faculty of Agriculture, Science and Technology, North-West University (Mafikeng Campus), Private Bag X2046, Mmabatho, 2735, South Africa

    Mwadham M. Kabanda

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Serobatse, K.R.N., Kabanda, M.M. Antioxidant and antimalarial properties of butein and homobutein based on their ability to chelate iron (II and III) cations: a DFT study in vacuo and in solution. Eur Food Res Technol 242, 71–90 (2016). https://doi.org/10.1007/s00217-015-2520-0

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