We found a match
Your institution may have access to this item. Find your institution then sign in to continue.
- Title
Investigation of quercetin molecule by quantum chemistry methods.
- Authors
Protsenko, I.
- Abstract
Background. Quercetin is a biologically active compound. It is widely used in medicine and pharmaceutics, in particular, for the prevention of cardiovascular diseases and some types of cancer [1]. Quercetin occurs in fruits such as apples, grapes, dark cherries and blueberries, and vegetables: onion, garlic, carrot, as well as in green tea and olive oil. Quercetin is also known as a good antioxidant [2]. Aim. In this paper, the author introduced a broad assumption about the use of quercetin. In particular, we can indicate that the presence of multifunctional bioactive compounds may owe to the formation of different conformations and strong intramolecular hydrogen bonds. Methods. Initial geometries of the quercetin molecule were fully optimized without any structural restrictions at the DFT B3LYP/6-311++G(d, p) theory level using Gaussian [3]. Taking 2 orientations for 5 hydroxyl groups along with 2 possible mutual orientations of hetero and modified phenyl rings one easily obtains a priori estimation of possible conformation number of 64. Results. The ab initio investigation has shown that the quercetin molecule can adopt any of 12 mirror symmetrical planar conformations. Electron energies were calculated at the MP2/6-311++G(d,p) theory level. To get a new conformation it is enough to change the torsion angles that contain hydroxyl groups and torsion angle between hetero and modified phenyl rings. To reveal intramolecular H-bonds in all the conformers, AIM method was used. To investigate the ways of quercetin molecule conformations [, the] interconversion suitable transition states were located by QST3 method. Conclusions. Comparing the data obtained for different conformations of the molecule quercetin, in a free state, can testify certain results: the value of energy corresponding to intramolecular H-bonds have the same order and are in a close range. Existence of strong intramolecular H-bonds in the quercetin molecule, the average energies of which are 3.46 – 5.82 kcal/mol, can, in particular, explain quercetin’s biological multifunctionality.
- Publication
Biopolymers & Cell, 2019, Vol 35, Issue 5, p395
- ISSN
0233-7657
- Publication type
Academic Journal