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Combined computational and experimental study on the inclusion complexes of β-cyclodextrin with selected food phenolic compounds

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Abstract

Phenolic compounds, such as caffeic acid, trans-ferulic, acid and p-coumaric acid that are commonly found in food products, are beneficial for human health. Cyclodextrins can form inclusion complexes with various organic compounds in which the physiochemical properties of the included organic molecules are changed. In this study, inclusion complexes of three phenolic compounds with β-cyclodextrin were investigated. The complexes were characterized by various analytical methods, including nuclear magnetic resonance (NMR) spectroscopy, Fourier IR (FT-IR) spectroscopy, mass spectrometry, differential scanning calorimetry, and scanning electron microscopy. Results showed that the phenolic compounds used in this study were able to form inclusion complexes in the hydrophobic cavity of β-cyclodextrin by non-covalent bonds. Their physicochemical properties were changed due to the complex formation. In addition, a computational study was performed to find factors that were responsible for binding forces between flavors and β-cyclodextrin. The quantum-mechanical calculations supported the results obtained from experimental studies. Thus, ΔHf for the complex of p-coumaric acid and β-cyclodextrin has been found as − 11.72 kcal/mol, which was about 3 kcal/mol more stable than for inclusion complexes of other flavors. Energies of frontier orbitals (higher occupied molecular orbital (HOMO) and lower unoccupied molecular orbital (LUMO)) were analyzed, and it was found that H-L gap for the complex of p-coumaric acid and β-cyclodextrin had the largest value (8.19 eV) in comparison to other complexes, which confirmed the experimental findings of the most stabile complex.

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Acknowledgments

Authors would like to thank Manfred Zähres, Dr. Angel Ugrinov, and Kristin Whitney for the technical assistance.

Funding

This work was also supported in part by the National Science Foundation through the ND EPSCoR Award #IIA-1355466 and by the State of North Dakota. Authors are also grateful for computer access and support provided by North Dakota State University, Center for Computationally Assisted Science and Technology (CCAST), and the Department of Energy through Grant No. DE-SC0001717.

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Authors and Affiliations

  1. Institute of Physical Chemistry, CENIDE, Duisburg-Essen University , Universitätsstr. 2, 45141, Essen, Germany

    Tuba Simsek & Christian Mayer

  2. Department of Plant Sciences, North Dakota State University, Fargo, ND, USA

    Tuba Simsek & Senay Simsek

  3. Department of Coatings and Polymeric Materials, North Dakota State University, Fargo, ND, USA

    Bakhtiyor Rasulev

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  1. Tuba Simsek
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  2. Senay Simsek
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  3. Christian Mayer
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Correspondence to Christian Mayer or Bakhtiyor Rasulev.

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Simsek, T., Simsek, S., Mayer, C. et al. Combined computational and experimental study on the inclusion complexes of β-cyclodextrin with selected food phenolic compounds. Struct Chem 30, 1395–1406 (2019). https://doi.org/10.1007/s11224-019-01347-4

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  • DOI: https://doi.org/10.1007/s11224-019-01347-4

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