871
Views
7
CrossRef citations to date
0
Altmetric
Original Article

Quantum chemical treatment of β-sitosterol molecule

, &
Pages 637-642 | Received 24 Feb 2009, Accepted 13 Apr 2009, Published online: 30 Apr 2010

References

  • Allinger NL (1977): Conformational analysis 130. MM2. A hydrocarbon force field utilizingV1 and V2 torsional terms. J Am Chem Soc 99: 8127–8134.
  • Awad AB, Fink CS (2000): Phytosterols as anticancer dietary components: Evidence and mechanism of action. J Nutr 130: 2127–2130.
  • Awad AB, Barta SL, Fink CS, Bradford PG (2008): Beta-Sitosterol enhances tamoxifen effectiveness on breast cancer cells by affecting ceramide metabolism. Mol Nutr Food Res 52: 419–426.
  • Becke AD (1993): Density-functional thermochemistry. III. The role of exact exchange. J Chem Phys 98: 5648–5652.
  • Berge KE, Tian H, Graf GA, Yu L, Grishin NV, Schultz J, Kwiterovich P, Shan B, Barnes R, Hobbs HH (2000): Accumulation of dietary cholesterol in sitosterolemia caused by mutations in adjacent ABC transporters. Science 290: 1709–1711.
  • Bosner MS, Lange LG, Stenson WF, Ostlund RE Jr (1999): Percent cholesterol absorption in normal women and men quantified with dual stable isotopic tracers and negative ion mass spectrometry. J Lipid Res 40: 302–308.
  • Bouic PJ, Lamprecht JH (1999): Plant sterols and sterolins: A review of their immune-modulating properties. Alternat Med Rev 4: 170–177.
  • Burkert U, Allinger NL (1982): Molecular Mechanics. ACS Monograph 177. Washington, ACS.
  • Denis PA (2008): Theoretical investigation of nitrogen distributed corannulenes. J Mol Struct (Theochem) 865: 8–13.
  • Duester KC (2001): Avocado fruit is a rich source of beta-sitosterol. J Am Diet Assoc 101: 404–405.
  • Fernandez ML, Vega-López S (2005): Efficacy and safety of sitosterol in the management of blood cholesterol levels. Cardiovasc Drug Rev 23: 57–70.
  • Fletcher P (1990): Practical Methods of Optimization. Weinheim, Wiley-VCH.
  • Gaussian-03, Revision D.01. Wallingford, CT, Gaussian, Inc., 2004.
  • Gerber GS (2002):Phytotherapy for benign prostatic hyperplasia. Curr Urol Rep 3: 285–291.
  • Gylling H, Miettinen TA (2005): The effect of plant stanol- and sterol-enriched foods on lipid metabolism, serum lipids and coronary heart disease. Ann Clin Biochem 42: 254–263.
  • Hazard SE, Patel SB (2007): Sterolins ABCG5 and ABCG8: regulators of whole body dietary sterols. Pflügers Arch 453: 745–752.
  • Hehre WJ, Ditchfield R, Pople JA (1972): Self-consistent molecular orbital methods. XII. Further extensions of gaussian-type basis sets for use in molecular orbital studies of organic molecules. J Chem Phys 56: 2257–2261.
  • Heinemann T, Axtmann G, von Bergmann K (1993): Comparison of intestinal absorption of cholesterol with different plant sterols in man. Eur J Clin Invest 23: 827–831.
  • HyperChem, Release 7.5. Gainesville, FL, Hypercube, Inc., 2002.
  • Jansen PJ, Lütjohann D, Abildayeva K, Vanmierlo T, Plösch T, Plat J, von Bergmann K, Groen AJ, Ramaekers FC, Kuipers F, Mulder M (2006):Dietary plant sterols accumulate in the brain. Biochim Biophys Acta 1761: 445–453.
  • Jayaprakasha GK, Mandadi KK, Poulose SM, Jadegoud Y, Gowda GAN, Bhimanagouda S, Patila BS (2007): Inhibition of colon cancer cell growth and antioxidant activity of bioactive compounds from Poncirus trifoliata (L.) Raf. Bioorg Med Chem 15: 4923–4932.
  • Jourdain C, Tenca G, Deguercy A, Troplin P, Poelman D (2006): In-vitro effects of polyphenols from cocoa and beta-sitosterol on the growth of human prostate cancer and normal cells. Eur J Cancer Prev 15: 353–361.
  • Kidambi S, Patel SB (2008): Sitosterolaemia: Pathophysiology, clinical presentation and laboratory diagnosis. J Clin Pathol 61: 588–594.
  • Kohn W, Sham LJ (1965): Self-consistent equations including exchange and correlation effects. Phys Rev 140: A1133–A1138.
  • Lee C, Yang W, Parr RG (1988): Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Phys Rev B 37: 785–789.
  • Leitzmann C (2005): Vegetarian diets: what are the advantages? Forum Nutr 57: 147–156.
  • Ling WH, Jones PJ (1995): Dietary phytosterols: A review of metabolism, benefits and side effects. Life Sci 57: 195–206.
  • Moon DO, Lee KJ, Choi YH, Kim GY (2007): Beta-sitosterol-induced-apoptosis is mediated by the activation of ERK and the downregulation of Akt in MCA-102 murine fibrosarcoma cells. Int Immunopharmacol 7: 1044–1053.
  • Ovesná Z, Vachálková A, Horváthová K (2004): Taraxasterol and beta-sitosterol: New naturally compounds with chemoprotective/chemopreventive effects. Neoplasma 51: 407–414.
  • Patch CS, Tapsell LC, Williams PG, Gordon M (2006): Plant sterols as dietary adjuvants in the reduction of cardiovascular risk: Theory and evidence. Vasc Health Risk Manag 2: 157–162.
  • Pegel KH (1997) The importance of sitosterol and sitosterolin in human and animal nutrition. South Afr J Sci 93: 263–268.
  • Reynolds TM, Mardani A, Twomey PJ, Wierzbickid AS (2008): Targeted versus global approaches to the management of hypercholesterolaemia. J R Soc Promot Health 128: 248–254.
  • Roothaan CC (1951): New developments in molecular orbital theory. Rev Mod Phys 23: 69–89.
  • Rudkowska I (2008): Functional foods for cardiovascular disease in women. Menopause Int 14: 63–69.
  • Ryan E, Galvin K, O’Connor TP, Maguire AR, O’Brien NM (2007): Phytosterol, squalene, tocopherol content and fatty acid profile of selected seeds, grains, and legumes. Plant Foods Hum Nutr 62: 85–91.
  • Scott AP, Radom L (1996): Harmonic vibrational frequencies: an evaluation of Hartree-Fock, Moller-Plesset, quadratic configuration interaction, density functional theory, and semiempirical scale factors. J Phys Chem 100: 16502–16513.
  • Sigma Aldrich Co. (2009): Available at http://www.sigmaaldrich.com/spectra/ftir/ FTIR008804.pdf.
  • Stewart JJP (1989): Optimization of parameters for semiempirical methods. I. Method. J Comput Chem 10: 209–220.
  • Stewart JJP (1990): MOPAC: A semiempirical molecular orbital program. J Comput Aided Mol Design 4: 1–105.
  • Stone NJ, Van Horn L (2002): Therapeutic lifestyle change and Adult Treatment Panel III: Evidence then and now. Curr Atheroscler Rep 4: 433–443.
  • Tejero I, Eriksson LA, Gonzalez-Lafont Marquet AJ, Lluch JM (2004): Hydrogen abstraction by soybean lipoxygenase-1. Density functional theory study on active site models in terms of Gibbs free energies. J Phys Chem B 108: 13831–13838.
  • Vecka M, Zák A, Tvrzická E (2007): Phytosterols as a functional food. Cas Lek Cesk 146: 337–342.
  • Yoshida M, Aihara JI (1999): Validity of the weighted HOMO-LUMO energy separation as an index of kinetic stability for fullerenes with up to 120 carbon atoms. Phys Chem Chem Phys 1: 227–230.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.