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Oenin/Syringic Acid Copigmentation: Insights From a Theoretical Study.

Yunkui Li1,2, Mario Prejanò2, Marirosa Toscano2

  • 1College of Enology, Northwest A&F University, Yangling, China.

Frontiers in Chemistry
|September 5, 2019
PubMed
Summary

This study models oenin/syringic acid copigmentation using computational methods. Results show hydrogen bonding is key to anthocyanin-copigment interactions and complex formation.

Keywords:
anthocyanincopigmentationdensity functional theoryhydrogen bondingmalvidin-3-O-glucosideoeninred winesyringic acid

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Area of Science:

  • Computational chemistry
  • Molecular modeling
  • Food chemistry

Background:

  • Anthocyanins are natural pigments responsible for red, purple, and blue colors in plants.
  • Copigmentation, the interaction between anthocyanins and other molecules (copigments), enhances color stability and intensity.
  • Oenin and syringic acid are key compounds involved in grape and wine color.

Purpose of the Study:

  • To develop a computational model for oenin/syringic acid copigmentation.
  • To investigate the non-covalent interactions between anthocyanins and copigments.
  • To understand the structural basis of copigmentation complex formation.

Main Methods:

  • Dispersion-corrected density functional theory (DFT) calculations.
  • Implicit solvent model for simulating the environment.
  • Analysis of binding free energy and visible spectrum shifts.

Main Results:

  • The computational model accurately predicts binding free energy and spectral shifts, aligning with experimental data.
  • The model provides a detailed structural description of the oenin/syringic acid complex.
  • Intermolecular hydrogen bonding, particularly involving the sugar moiety of oenin, was identified as crucial.

Conclusions:

  • The proposed computational model is effective for studying anthocyanin-copigment interactions.
  • Hydrogen bonding is a primary determinant in the formation and characteristics of copigmentation complexes.
  • This research offers insights into the molecular mechanisms underlying color stabilization in natural products.