Quantum chemical treatment of beta-sitosterol molecule

Date

2010-06-10

Author

Kurban, Sevil
ERKOÇ, Figen
Erkoç, Şakir

Metadata

Show full item record

This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

Item Usage Stats

80
views

0
downloads

beta-Sitosterol is used as a dietary supplement for lowering plasma cholesterol, and has atherosclerosis preventive, anti-inflammatory, antimicrobial, antipyretic, induced apoptosis, and anticancer effects. In order to understand the effect of the molecule we have investigated the molecule theoretically. The structural, vibrational, and electronic properties of the beta-sitosterol molecule have been investigated theoretically by performing molecular mechanics (MM+ force field), semiempirical self-consistent-field molecular-orbital (PM3), and density functional theory (B3LYP) calculations. The geometry of the considered molecule has been optimized; the vibrational dynamics and the electronic properties have been calculated in its ground state in the gas phase. The optimized structure of the molecule is not planar, and its heat of formation is exothermic. The calculated infrared spectrum for beta-sitosterol agrees well qualitatively with the experimentally determined FTIR spectrum. The interfrontier molecular orbitals are localized mainly on the double C-C bond, and the energy difference of the corresponding orbitals is relatively small, which makes the molecule kinetically stable. According to the calculated dipole moment, beta-sitosterol is a polar molecule. The calculated results for the beta-sitosterol molecule in the present study will aid in elucidation of the mechanism of action and may further be used in lipid metabolism drug design studies.

Subject Keywords

Beta-Sitosterol, Density functional theory method, MM method, Semiempirical PM3 method

URI

https://hdl.handle.net/11511/57492

Journal

PHARMACEUTICAL BIOLOGY

DOI

https://doi.org/10.1080/13880200903229106

Collections

Department of Physics, Article

Suggestions

OpenMETU
Core

The effects of high cholesterol/high fat diet on endoplasmic reticulum stress and neuronal dysfunction in the hippocampus and cerebral cortex of APOE-/- MICE Mengi, Naz; Yanık, Tülin; Department of Molecular Biology and Genetics (2019) Hyperlipidemia is an obesity-associated lipid metabolism disorder with high serum total cholesterol (TC) levels and is known to be a risk factor for neurodegenerative diseases. High-fat diet (HFD) induced elevated inflammation levels accompanied by increased levels of apoptosis markers and decreased levels of synaptic proteins in the hippocampus points out a possible neuronal loss. Protein kinase RNA-like endoplasmic reticulum kinase (PERK) pathway is activated by endoplasmic reticulum (ER) stress. The acti...
Structural effects of simvastatin on liver rate tissue: Fourier transform infrared and Raman microspectroscopic studies Garip, Sebnem; Bayari, Sevgi Haman; Severcan, Mete; Abbas, Sherif; Lednev, Igor K.; Severcan, Feride (2016-02-01) Simvastatin is one of the most frequently prescribed statins because of its efficacy in the treatment of hypercholesterolemia, reducing cardiovascular risk and related mortality. Determination of its side effects on different tissues is mandatory to improve safe use of this drug. In the present study, the effects of simvastatin on molecular composition and structure of healthy rat livers were investigated by Fourier transform infrared and Raman imaging. Simvastatin-treated groups received 50 mg/kg/day simva...
Simple and Rapid Method for the Simultaneous Determination of Cholesterol and Retinol in Meat Using Normal-Phase HPLC Technique DOMINGUEZ, Ruben; BARBA, Francisco J.; CENTENO, Juan A.; PUTNIK, Predrag; Alpas, Hami; LORENZO, Jose M. (2018-02-01) A direct saponification and normal-phase high-performance liquid chromatography (NP-HPLC) procedure was developed for simultaneous determination of cholesterol and retinol in meat. A normal-phase silica column fitted with diode array detection at 208 nm for cholesterol and fluorescence detection (lambda-excitation 344 nm/lambda-emission 472 nm) for retinol, with mobile phase consisting of 2% (v/v) 2-propanol in n-hexane was used. Cholesterol was eluted at 10 min and retinol at 12.66 min. High linearity (R (...
Evaluation and discrimination of simvastatin-induced structural alterations in proteins of different rat tissues by FTIR spectroscopy and neural network analysis Garip, Sebnem; Yapici, Engin; Ozek, Nihal Simsek; Severcan, Mete; Severcan, Feride (Royal Society of Chemistry (RSC), 2010-01-01) Statins are commonly used to control hypercholesterolemia and to prevent cardiovascular diseases. Among the statins, Simvastatin is one of the most frequently prescribed statins because of its efficacy in reducing LDL lipoprotein cholesterol levels, its tolerability, and its reduction of cardiovascular risk and mortality. Conflicting results have been reported with regard to benefits (pleiotropic effects) as well as risks (adverse effects) of simvastatin on different soft and hard tissues. In the current st...
Investigation of the effect of sodium butyrate on the regulation of cyclooxygenase-2 in colon cancer cell lines Caco-2 and HT-29 Ülgen, Doğukan Hazar; Banerjee, Sreeparna; Department of Biology (2015) Sodium butyrate (NaBt) is a four-carbon short-chain fatty acid histone deacetylase inhibitor (HDACi) that is available in the colon through the commensal microbiota-mediated fermentation of dietary fibers. It is the main source of energy for colonocytes, and is regarded to have tumor suppressive effects, most prominently in colorectal cancer (CRC). Cyclooxygenase-2 (COX-2) is a gene important in the inflammatory response due to its ability to convert arachidonic acid to prostaglandins. Overexpression and ov...

Citation Formats

S. Kurban, F. ERKOÇ, and Ş. Erkoç, “Quantum chemical treatment of beta-sitosterol molecule,” PHARMACEUTICAL BIOLOGY, pp. 637–642, 2010, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/57492.