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A computational study of the interactions between anthocyans and cyclodextrins.

Raluca Pop1, Adina Căta2, Mariana Nela Ștefănuț2

  • 1Faculty of Pharmacy, University of Medicine and Pharmacy "Victor Babeş" Timisoara, Eftimie Murgu Square 2, 300041 Timişoara, Romania.

Zeitschrift Fur Naturforschung. C, Journal of Biosciences
|July 19, 2020
PubMed
Summary

Anthocyanins interact with cyclodextrins, forming inclusion complexes. Anthocyanidin-3-O-rutinosides show a preference for complexation, especially with beta- and gamma-cyclodextrins, due to hydrogen bonding.

Keywords:
anthocyanscyclodextrinsinclusion complexesmolecular docking

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Area of Science:

  • * Computational chemistry
  • * Supramolecular chemistry
  • * Natural product chemistry

Background:

  • * Anthocyanins are natural pigments with diverse structures and pH-dependent forms.
  • * Cyclodextrins are cyclic oligosaccharides known for their ability to form inclusion complexes.
  • * Understanding these interactions is crucial for applications in food, pharmaceuticals, and materials science.

Purpose of the Study:

  • * To computationally investigate the interactions between six anthocyanins and cyclodextrins.
  • * To analyze the influence of pH on anthocyanin structure and its impact on complexation.
  • * To identify optimal conditions and anthocyanin derivatives for stable inclusion complex formation.

Main Methods:

  • * Employed computational techniques to model interactions.
  • * Considered four pH-dependent structural forms of anthocyanins (flavylium cations, hemiketals, quinones).
  • * Evaluated the binding affinities and interaction mechanisms between anthocyanins and cyclodextrins (alpha, beta, gamma).

Main Results:

  • * Anthocyanidin-3-O-rutinosides demonstrated a higher propensity for forming inclusion complexes with cyclodextrins.
  • * The increased number of hydroxyl (OH) groups in anthocyanidin-3-O-rutinosides facilitated stronger hydrogen bonding interactions.
  • * Beta- and gamma-cyclodextrins showed the most favorable complexation results across all tested anthocyanin structures and pH conditions.

Conclusions:

  • * Anthocyanidin-3-O-rutinoside derivatives are promising candidates for developing stable cyclodextrin inclusion complexes.
  • * The choice of cyclodextrin (beta- or gamma-) significantly influences complexation efficiency.
  • * Computational modeling provides valuable insights into optimizing anthocyanin-cyclodextrin interactions for various applications.