Application of GC/EIMS in Combination with Semi-Empirical Calculations for Identification and Investigation of Some Volatile Components in Basil Essential Oil
Volatile components in the extracts of basil leaves (Ocimum basilicum L.) were identified by gas chromatography/mass spectrometry (GC/MS) with electron ionization (EI) mode. The major volatile components of basil under investigation are α-pinene, sabinene, β-pinene, d-limonene, eucalyptol, l-linalool and estragole. Electron ionization mass spectra of these compounds have been obtained and investigated. Furthermore, the semi-empirical MNDO [Modified Neglect of Diatomic Overlap] method was used to calculate the thermochemical data for the structural properties of these compounds.
References
[1]
Sajjadi, S.E. (2006) Analysis of the Essential Oils of Two Cultivated Basil (Ocimum basilicum L.) from Iran. DARU, 14, 128-130. http://daru.tums.ac.ir/index.php/daru/article/viewFile/278/278
[2]
Runyoro, D., Ngassapa, O., Vagionas, K., Aligiannis, N., Graikou, K. and Chinou, I. (2010) Chemical Composition and Antimicrobial Activity of the Essential Oils of Four Ocimum Species Growing in Tanzania. Food Chemistry, 119, 311-316. http://dx.doi.org/10.1016/j.foodchem.2009.06.028
[3]
Telci, I., Bayram, E., Yilmaz, G. and Avci, B. (2006) Variability in Essential Oil Composition of Turkish Basils (Ocimum basilicum L.). Biochemical Systematics and Ecology, 34, 489-497. http://dx.doi.org/10.1016/j.bse.2006.01.009
[4]
Anackov, G., Bozin, B., Zoric, L., Vukov, D., Mimica-Dukic, N., Merkulov, L., Ruzica Igic, Jovanovic, M. and Boza, P. (2009) Chemical Composition of Essential Oil and Leaf Anatomy of Salvia bertolonii Vis. and Salvia pratensis L. (Sect. Plethiosphace, Lamiaceae). Molecules, 14, 1-9. http://dx.doi.org/10.3390/molecules14010001
[5]
Wogiatzi, Ε., Papachatzis, Α., Kalorizou, Η., Chouliara, Α. and Chouliaras, Ν. (2011) Evaluation of Essential Oil Yield and Chemical Components of Selective Basil Cultivars. Journal of Biotechnology & Biotechnological Equipments, 25, 2525-2527. http://dx.doi.org/10.5504/BBEQ.2011.0067
[6]
Pripdeevech, P., Chumpolsri, W., Suttiarporn, P. and Wongpornchai, S. (2010) The Chemical Composition and Antioxidant Activities of Basil from Thailand Using Retention Indices and Comprehensive Two-dimensional Gas Chromatography. Journal of Serbian Chemical Society, 75, 1503-1513. http://dx.doi.org/10.2298/JSC100203125P
[7]
Ismail, M. (2006) Central Properties and Chemical Composition of Ocimum basilicum. Essential Oil. Pharmaceutical Biology, 44, 619. http://dx.doi.org/10.1080/13880200600897544
[8]
Lee, S., Umano, K., Shibamoto, T. and Lee, S. (2005) Identification of Volatile Components in Basil (L.) and Thyme Leaves (L.) and Their Antioxidant Properties. Food Chemistry, 91, 131-137.
http://dx.doi.org/10.1016/j.foodchem.2004.05.056
[9]
Klimánková, S., Holadová, K., Hajslová, J., Cajka, T., Poustka, J. and Koudela, M. (2007) Roma Profile of Five Basil (Ocimum basilicum L.) Cultivars Grown under Conventional and Organic Conditions. Food Chemistry, 107, 464-472.
http://dx.doi.org/10.1016/j.foodchem.2007.07.062
[10]
Cody, M., Laramee, J.A., Michael Nilles, J. and Dupont Durst, H. (2005) Direct Analysis in Real Time Mass Spectrometry. JEOL News, 40, No. 1.
https://www.chem.utoronto.ca/_shared/files/facilities/mass/DART_Mass_Spectrometry.pdf
[11]
Watson, J.J.T. and Sparkman, O.D. (2007) Introduction to Mass Spectrometry: Instrumentation, Applications, and Strategies for Data Interpretation. 4th Edition, John Wiley & Sons, Ltd., USA.
http://eu.wiley.com/WileyCDA/WileyTitle/productCd-0470516348.html
[12]
White, K.A.F. and Wood, M.G. (1986) Mass Spectrometry: Application in Science and Engineering. Wiley & Sons, Inc., USA. http://www.amazon.com/Mass-Spectrometry-Applications-Science-Engineering/dp/0471092363
[13]
Curtiss, L.A. and Raghavachari, K. (1969) “Computational Thermochemistry: Prediction and Estimation of Thermodynamics. American Chemical Society, Washington DC.
http://trove.nla.gov.au/work/7468809?selectedversion=NBD13645686
[14]
Dewar, M.J.S. (1969) The Molecular Orbital Theory of Organic Chemistry. McGraw-Hill, New York.
[15]
Pople, J.A. and Beveridge, D.L. (1970) Approximate Molecular Orbital Theory. McGraw-Hill, New York.
http://www.amazon.com/Approximate-Molecular-Orbital-Theory-Beveridge/dp/B004CFL4KY
[16]
Murrell, J.N. and Harget, A.J. (1972) Semiempirical Self-Consistent-Field Molecular Orbital Theory of Molecules. Wiley, New York.
http://www.amazon.com/Semi-empirical-Self-consistent-field-molecular-orbital-Theory-Molecules-Murrell/dp/0471626805
[17]
Segal, G.A., Ed. (1977) Modern Theoretical Chemistry. Springer, New York.
http://link.springer.com/bookseries/10920
Jug, K. (1980) Quantum Chemical Methods and Their Applications to Chemical Reactions. Theoretica Chimica Acta, 54, 263-300. http://dx.doi.org/10.1007/BF00552463
[20]
Dewar, M.J.S. (1985) Applications of Quantum Mechanical Molecular Models to Chemical Problems. Part 70. Quantum Mechanical Molecular Models. The Journal of Physical Chemistry, 89, 2145-2150.
http://dx.doi.org/10.1021/j100257a004
[21]
Thiel, W. (1988) Semiempirical Methods: Current Status and Perspectives. Tetrahedron, 44, 7393-7408.
http://dx.doi.org/10.1016/S0040-4020(01)86235-9
[22]
Stewart, J.J.P. (1990) MOPAC: A Semiempirical Molecular Orbital Program. Journal of Computer-Aided Molecular Design, 4, 1-103. http://dx.doi.org/10.1007/BF00128336
[23]
Stewart, J.J.P. (1991) Semiempirical Molecular Orbital Methods. In: Lipkowitz, K.B. and Boyd, D.B., Eds., Reviews in Computational Chemistry, Vol. 2, VCH Publishers, New York, 45-81.
http://onlinelibrary.wiley.com/book/10.1002/9780470125793
http://dx.doi.org/10.1002/9780470125793
[24]
Zamer, M.C. (1990) Semiempirical Molecular Orbital Methods. In: Lipkowitz, K.B. and Boyd, D.B., Eds., Reviews in Computational Chemistry, Vol. 1, VCH Publishers; New York, 313.
http://onlinelibrary.wiley.com/book/10.1002/9780470125786
http://dx.doi.org/10.1002/9780470125786
[25]
Thiel, W. (1996) Perspectives on Semiempirical Molecular Orbital Theory. Advances in Chemical Physics, 93, 703- 757. http://dx.doi.org/10.1002/9780470141526.ch10
[26]
Ribeiro da Silva, M.A.V. and Matos, M.A.R. (1997) Recent Work on the Thermochemistry of Some Nitrogen Heterocycles. Pure & Applied Chemistry, 69, 2295-2306. http://dx.doi.org/10.1351/pac199769112295
[27]
Elsherbiny, E.A., El-Khateeb, A.Y. and Azzaz, N.A. (2016) Chemical Composition and Fungicidal Effects of Ocimum basilicum Essential Oil on Bipolaris and Cochliobolus Species. Journal of Agricultural Science and Technology (Under Press).
[28]
Dewar, M.J.S. and Thiel, W. (1977) Ground States of Molecules, 38. The MNDO Method. Approximations and Parameters. Journal of American Chemical Society, 99, 4899-4907. http://dx.doi.org/10.1021/ja00457a004
[29]
Thiel, W. (2003) Handbook of Molecular Physics and Quantum Chemistry. Wilson, S. Ed., Vol.2, Wiley, 487-502.
[30]
HyperChemTM (2002) Release 7.5 Pro for Windows “Molecular Modeling System”. Hypercube Inc.
