title: Quantum chemical treatment of beta-sitosterol molecule.
abstract: 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.
authors.affiliation: Department of Biochemistry, Meram Faculty of Medicine, Selçuk University, Konya, Turkey.
authors.forename: Sevil
authors.initials: S
authors.lastname: Kurban
authors.forename: Figen
authors.initials: F
authors.lastname: Erkoç
authors.forename: Sakir
authors.initials: S
authors.lastname: Erkoç
mesh_terms: D004581:Electronics; D000960:Hypolipidemic Agents / Q000737:chemistry; D008958:Models, Molecular; D011789:Quantum Theory; D012855:Sitosterols / Q000737:chemistry*; D013055:Spectrophotometry, Infrared; D017550:Spectroscopy, Fourier Transform Infrared; D014732:Vibration
chemical_list: D000960:Hypolipidemic Agents; D012855:Sitosterols; C025473:gamma-sitosterol