Skip to content
Research Article Open access CC BY 4.0

Comparative Study of Epicatechin–Phenylalanine and Epicatechin–Alanine Interactions Using Quantum Chemistry Methods

Adenidji Ganiyou, Essoh Akpa Eugene, N’Guessan Boka Robert, Kone Soleymane

Asian Journal of Chemical Sciences · pp. 1–15 · Published 8 Jan 2025

10.9734/ajocs/2025/v15i1344

Abstract

Aims: This research aims to analyze the interactions within Epicatechin…Phenylalanine complexes and compare them to those in Epicatechin…Alanine complexes through theoretical chemistry calculations. Methodology: The interactions between Epicatechin and Phenylalanine, an amino acid, are evaluated using theoretical chemistry methods. Calculations performed at the DFT/B3LYP/6-31+G(d,p) level are used to characterize the complexes and their individual monomers. Geometric, energetic, and spectroscopic parameters, along with QTAIM (Quantum Theory of Atoms in Molecules), NBO (Natural Bond Orbital), and NCI (Non-Covalent Interaction) topological analyses, provide insights into the nature and type of these interactions. Results: The interaction energies of Epicatechin-Phenylalanine complexes exceed those of Epicatechin-Alanine complexes. Unlike the Epicatechin-Alanine complexes, the formation of Epicatechin-Phenylalanine complexes is non-spontaneous. NBO analysis reveals that Epicatechin-Alanine complexes exhibit a greater number of interactions compared to Epicatechin-Phenylalanine complexes, including repulsive interactions attributed to the phenyl group. Moreover, the total stabilization energies of Epicatechin-Phenylalanine complexes are higher than those of their Catechin-Alanine and Epicatechin-Alanine counterparts. Conclusion: The non-covalent bonds formed in epicatechin-phenylalanine complexes are stronger and more numerous than those in catechin-alanine and epicatechin-alanine complexes.

Polyphenols epicatechin catechin DFT QTAIM NBO NCI

References (11)

  1. 1 A quantum theory of molecular structure and its applications [DOI]
  2. 2 Behavior of Ylides Containing N, O, and C Atoms as Hydrogen Bond Acceptors [DOI]
  3. 3 The Biological Relevance of Direct Antioxidant Effects of Polyphenols for Cardiovascular Health in Humans Is Not Established1–4 [DOI]
  4. 4 Cooperativity in Hydrogen-Bonded Interactions: Ab Initio and “Atoms in Molecules” Analyses [DOI]
  5. 5 Varietal Differences among the Polyphenol Profiles of Seven Table Grape Cultivars Studied by LC−DAD−MS−MS [DOI]
  6. 6 Spectroscopic analysis and DFT calculations of a food additive Carmoisine [DOI]
  7. 7 Intermolecular interaction in nucleobases and dimethyl sulfoxide/water molecules: A DFT, NBO, AIM and NCI analysis [DOI]
  8. 8 Confinement induced thermodynamic and kinetic facilitation of some Diels–Alder reactions inside a CB[7] cavitand [DOI]
  9. 9 Catechin and Epicatechin. What’s the More Reactive? [DOI]
  10. 10 Differences in Antioxidative Efficiency of Catechins in Various Metal-Induced Lipid Peroxidations in Cultured Hepatocytes. [DOI]
  11. 11 Basis Set Superposition Error: Effects of Atomic Basis Set Optimization on Value of Counterpoise Correction [DOI]

Cited by 0

No indexed citations yet.

Article metrics

Real usage data collected on this platform.

36

Page views

0

PDF downloads

4

Outbound clicks

0

Citations

Views over time

Views by country

Approximate, from request IP at view time — not citizenship or institution. Countries with fewer than 5 views are grouped as "Other".

Traffic sources

Referring site, by host.

Views and downloads exclude known bots/crawlers. Citations combines this platform's own DOI-resolved index with each external source's own reported total — see Cited by above for individually listed citing works. Last refreshed 0 seconds ago.