A theoretical exploration of the intermolecular interactions between resveratrol and water: a DFT and AIM analysis

• Published in: Journal of molecular modeling 2019-03, Vol.25 (3), p.56-11, Article 56
• Main Authors: Suvitha, A., Venkataramanan, N. S., Sahara, R., Kawazoe, Y.
• Format: Article
• Language: English
• Subjects: Blue shift; Bonding strength; Characterization and Evaluation of Materials; Chemical bonds; Chemistry; Chemistry and Materials Science; Complex formation; Computer Appl. in Life Sciences; Computer Applications in Chemistry; Density functional theory; Dispersion; Electron density; Hydrogen; Hydrogen bonding; Hydrogen bonds; Hydroxyl groups; Molecular Medicine; Nervous system; Original Paper; Theoretical and Computational Chemistry; Water chemistry
• ISSN: 1610-2940; 0948-5023
• DOI: 10.1007/s00894-019-3941-7

The polyphenolic compound resveratrol, classified under stilbenes, offers a broad range of health advantages, including neuroprotection and playing a role in autophagy in the nervous system. However, resveratrol has poor water solubility and is soluble in the gel phase in liposomal membranes. The main aim of this work was to understand the nature of the interactions between resveratrol and water molecules. In the present study, we used the dispersion corrected density functional theory (DFT) method to study hydrogen bonding interactions. Eight different geometries of resveratrol-water complexes were identified by optimizing the geometries by placing water at various locations. We observed the two lowest energy structures to be isoenergetic. In most complexes, water interaction occurs with phenolic hydrogen as all the phenolic hydroxyl groups have identical V s,max values. Energy decomposition analysis shows that the dispersion contribution was minimal in these complexes, while electrostatic and orbital contributions were larger. Complex formation between water and the resveratrol molecule results in a blue shift in the vibrational frequency, along with an increase in intensity due to the transfer of electron density. The hydrogen bonds in the resveratrol–water complexes have closed-shell interactions with a medium-to-strong bonding nature. Noncovalent index analysis of the complexes shows that, in addition to hydrogen bonding, electrostatic and van der Waal’s interactions play a key role in stabilizing the complexes. Graphical abstract Noncovalent index analysis showing that, in addition to hydrogen bonding, electrostatic and van der Waal’s interactions play a major role in stabilizing resveratrol-water complexes