Structural Chemistry

, Volume 30, Issue 4, pp 1395–1406 | Cite as

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

  • Tuba Simsek
  • Senay Simsek
  • Christian MayerEmail author
  • Bakhtiyor RasulevEmail author
Original Research


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.


Cyclodextrin Phenolic compounds Inclusion complex Modeling Quantum chemical properties Interaction 



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

Funding information

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.

Compliance with ethical standards

Conflict of interest

The authors declare that they have no conflict of interest.


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© Springer Science+Business Media, LLC, part of Springer Nature 2019

Authors and Affiliations

  1. 1.Institute of Physical Chemistry, CENIDEDuisburg-Essen University EssenGermany
  2. 2.Department of Plant SciencesNorth Dakota State UniversityFargoUSA
  3. 3.Department of Coatings and Polymeric MaterialsNorth Dakota State UniversityFargoUSA

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