Advertisement

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
  • 25 Downloads

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.

Keywords

Cyclodextrin Phenolic compounds Inclusion complex Modeling Quantum chemical properties Interaction 

Notes

Acknowledgments

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.

References

  1. 1.
    Dykes L, Rooney LW (2007) Phenolic compounds in cereal grains and their health benefits. Cereal Foods World 3:105–111Google Scholar
  2. 2.
    Pinho E, Grootveld M, Soares G, Henriques M (2013) Cyclodextrins as encapsulation agents for plant bioactive compounds. Carbohydr Polym 101:121–135CrossRefGoogle Scholar
  3. 3.
    Liu B, Zeng J, Chen C, Liu Y, Ma H, Mo H, Liang G (2015) Interaction of cinnamic acid derivates with β-cyclodextrin in water: experimental and molecular modeling studies. Food Chem 194:1156–1163CrossRefGoogle Scholar
  4. 4.
    Kikuzaki H, Hisamoto M, Hirose K, Akiyama K, Taniguchi H (2002) Antioxidant properties of ferulic acid and its related compounds. J Agric Food Chem 50(7):2161–2168CrossRefGoogle Scholar
  5. 5.
    Reis Giada ML (2013) Food phenolic compounds: main classes, sources and their antioxidant powder. Oxidative stress and chronic degenerative diseases. InTechOpen Ltd, London, pp 87–112Google Scholar
  6. 6.
    Binello A, Robaldo B, Barge A, Cavalli R, Cravotto G (2008) Synthesis of cyclodextrin-based polymers and their use as debittering agents. J Appl Polym Sci 107:2549–2557CrossRefGoogle Scholar
  7. 7.
    Villiers A (1891) Sur la fermentation de la feculepar l’action du ferment butyrique. CR Hebd Seances Acad Sci 112:536–538Google Scholar
  8. 8.
    Hedges RA (1998) Industrial applications of cyclodextrins. Chem Rev 98:2035–2044CrossRefGoogle Scholar
  9. 9.
    Dass CR, Jessup W, Apolipoprotiens AI (2000) Cyclodextrins and liposomes as potential drugs for the reversal of atherosclerosis. J Pharm Pharmacol 52:731–761CrossRefGoogle Scholar
  10. 10.
    Voncina B, Vivod V (2013) Cyclodextrins in textile finishing. Eco-friendly textile dyeing and finishing. InTechOpen Ltd, London, pp 53–75Google Scholar
  11. 11.
    Stella VJ, Rajewski RA (1997) Cyclodextrins: their future in drug formation and delivery. Pharm Res 14:556–567CrossRefGoogle Scholar
  12. 12.
    Szejtli J (1998) Introduction and general overview of cyclodextrin chemistry. Chem Rev 98(5):1743–1753CrossRefGoogle Scholar
  13. 13.
    Jambhekar S, Breen P (2016) Cyclodextrin in pharmaceutical formations I: structure and physicochemical properties, formation of complexes, and types of complex. Drug Discov Today 21:356–362CrossRefGoogle Scholar
  14. 14.
    Saenger W (1938) Stereochemistry of circularly closed oligosaccharides: cyclodextrins structure and function. Biochem Soc Trans 11:136–139CrossRefGoogle Scholar
  15. 15.
    Connors KA (1997) The stability of cyclodextrin complexes in solution. Chem Rev 97:325–1357CrossRefGoogle Scholar
  16. 16.
    Szejtli J (1982) Cyclodextrins and their inclusion complexes. Akadémiai Kiadó, BudapestGoogle Scholar
  17. 17.
    Hirayama F, Uekama K (1987) Methods of investigating and preparing inclusion compounds. In: Duchêne D (ed) Cyclodextrins and their industrial uses. Editions de Santé, Paris, pp 131–172Google Scholar
  18. 18.
    Chen G, Jiang M (2011) Cyclodextrin-based inclusion complexation bridging supramolecular chemistry and macromolecular self-assembly. Chem Soc Rev 40:2254–2266CrossRefGoogle Scholar
  19. 19.
    Nimse SB, Kim T (2013) Biological applications of functionalized calixarenes. Chem Soc Rev 42:366–386CrossRefGoogle Scholar
  20. 20.
    Muňoz-Botella S, Castillo B, Martyn MA (1995) Cyclodextrin properties and applications of inclusion complex formation. Ars Pharm 36:187–198Google Scholar
  21. 21.
    Scheidermann E, Stalcup AM (2000) Cyclodextrins: a versatile tool in separation science. J Chromatogr B 745:83–102CrossRefGoogle Scholar
  22. 22.
    Zhang J-Q, Wu D, Jiang K-M, Zhang D, Zheng X, Wan C-P, Zhu H-Y, Xie X-G, Jin Y, Lin J (2015) Preparation, spectroscopy and molecular modelling studies of the inclusion complex of cordycepin with cyclodextrins. Carbohydr Res 406:55e64CrossRefGoogle Scholar
  23. 23.
    Gannimani R, Perumal A, Ramesh M, Pillay K, Soliman ME, Govender P (2015) Antipyrine–gamma cyclodextrin inclusion complex: molecular modeling, preparation, characterization and cytotoxicity studies. J Mol Struct 1089:38–47CrossRefGoogle Scholar
  24. 24.
    Swiech O, Majdecki M, Debinski A, Krzak A, Stepkowski TM, Wojciuk G, Kruszewski M, Bilewicz R (2016). Nanoscale 8:16733CrossRefGoogle Scholar
  25. 25.
    Pinjari RV, Joshi KA, Gejji SP (2007). J Phys Chem A 111:13583–13589CrossRefGoogle Scholar
  26. 26.
    Zhao R, Sandström C, Zhang H, Tan T (2016) NMR study on the inclusion complexes of β-CD with isoflavones. Molecules 21:372CrossRefGoogle Scholar
  27. 27.
    Tonelli AEJ (2008) Cyclodextrins as a means to nanostructure and functionalize polymers. J Incl Phenom Macrocyl Chem 60:197–202CrossRefGoogle Scholar
  28. 28.
    Chen QR, Liu C, Liu FQ (2010) Applications of cyclodextrins in polymerization. Prog Chem 22:927–937Google Scholar
  29. 29.
    Steed JW, Atwood JL (2009) Molecular guests in solution, supramolecular chemistry, 2nd edn. Johns Wiley & Sons, Ltd, West Sussex, UK, Chapter 6, p 307Google Scholar
  30. 30.
    Singh J, Dartois A, Kaur L (2010) Starch digestibility in food matrix: a review. Trends Food Sci Technol 21:168–180CrossRefGoogle Scholar
  31. 31.
    Roux M, Perly B, Djedaini PF (2007) Self-assemblies of amphiphilic cyclodextrins. Eur Biophys J 36:861–867CrossRefGoogle Scholar
  32. 32.
    Avogadro: an open-source molecular builder and visualization tool. Version 1.20. http://avogadro.cc. Accessed 4 April 2018
  33. 33.
    Hanwell MD, Curtis DE, Lonie DC, Vandermeersch T, Zurek E, Hutchison GR (2012) Avogadro: an advanced semantic chemical editor, visualization, and analysis platform. J Cheminformatics 4:17CrossRefGoogle Scholar
  34. 34.
    MOPAC2012, James J. P. Stewart (2012) Stewart Computational Chemistry, Colorado Springs, CO, USA, http://OpenMOPAC.net. Accessed 5 Feb 2018
  35. 35.
    Puzyn T, Suzuki N, Haranczyk M, Rak J (2008) Calculation of quantum-mechanical descriptors for QSPR at the DFT level: is it necessary? J Chem Inf Model 48(6):1174–1180CrossRefGoogle Scholar
  36. 36.
    Turabekova MA, Rasulev BF (2004) A QSAR toxicity study of a series of alkaloids with the lycoctonine skeleton. Molecules 9(12):1194–1207CrossRefGoogle Scholar
  37. 37.
    Turabekova MA, Rasulev B, Dzhakhangirov FN, Salikhov SI (2008) Aconitum and Delphinium alkaloids: “Drug-likeness” descriptors related to toxic mode of action. Environ Toxicol Pharmacol 25(3):310–320CrossRefGoogle Scholar
  38. 38.
    Yilmaz H, Ahmed L, Rasulev B, Leszczynski J (2016) Application of ligand-and receptor-based approaches for prediction of the HIV-RT inhibitory activity of fullerene derivatives. J Nanopart Res 18(5):123CrossRefGoogle Scholar
  39. 39.
    Stewart JJP (2013) Optimization of parameters for semiempirical methods VI: more modifications to the NDDO approximations and re-optimization of parameters. J Mol Model 19:1–32CrossRefGoogle Scholar

Copyright information

© 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

Personalised recommendations