Suvitha A, Venkataramanan N S, Sahara R, Kawazoe Y
Department of Chemistry, School of Chemical and Biotechnology (SCBT), SASTRA Deemed to be University, Thanjavur, 613 401, India.
Research Center for Structural Materials, National Institute for Materials Science (NIMS), 1-2-1 Sengen, Tsukuba, Ibaraki, 305-0047, Japan.
J Mol Model. 2019 Feb 8;25(3):56. 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 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.
多酚类化合物白藜芦醇属于芪类，具有广泛的健康益处，包括神经保护作用以及在神经系统自噬中发挥作用。然而，白藜芦醇的水溶性较差，可溶于脂质体膜的凝胶相中。这项工作的主要目的是了解白藜芦醇与水分子之间相互作用的本质。在本研究中，我们使用色散校正密度泛函理论（DFT）方法来研究氢键相互作用。通过将水放置在不同位置优化几何结构，确定了八种不同几何结构的白藜芦醇 - 水复合物。我们观察到两个能量最低的结构具有相同的能量。在大多数复合物中，水与酚羟基氢发生相互作用，因为所有酚羟基具有相同的V值。能量分解分析表明，在这些复合物中色散贡献最小，而静电和轨道贡献较大。水与白藜芦醇分子之间形成复合物会导致振动频率发生蓝移，同时由于电子密度转移强度增加。白藜芦醇 - 水复合物中的氢键具有中等至强键性质的闭壳相互作用。对复合物的非共价指数分析表明，除氢键外，静电和范德华相互作用在稳定复合物中起关键作用。图形摘要 非共价指数分析表明，除氢键外，静电和范德华相互作用在稳定白藜芦醇 - 水复合物中起主要作用。
