The Essential Oils of Laurus nobilis L. and Molecular-Spectroscopic Analysis for 1,8-Cineole

Yıl 2021, Cilt: 25 Sayı: 3, 705 - 713, 30.06.2021

Ömer Elkıran Mustafa Karakaya

https://doi.org/10.16984/saufenbilder.867968

Öz

In the present study, the chemical composition of the essential oils obtained from leaves of Laurus nobilis naturally grown in Turkey were evaluated using by GC and GC-MS and chemical differences were depated in means of chemotaxonomy. The leaves of the plant samples were hydro-distilled. Twenty components were identified representing 99.3% of the oils, The main compounds in the essential oils were; 1,8-cineole (%48.47), β-pinene (%14.45), linalool (%8.15) and α-pinene (%5.97). In addition, the complexation energies, chemical shifts of the carbon and hydrogen atoms in the 1,8-cineole structures were calculated by ab initio theoretical approaches. The performances of the B3LYP and M06 functionals were tested on carbon and hydrogen complexation energies of the investigated compound. The electronegativity effect of oxygen and solvent effect on complexation energy of the carbons and hydrogens were evaluated with the results obtained.

Anahtar Kelimeler

Laurus nobilis, Essential oils, 1,8-cineole, GC-MS, Complexation energy, Density functional theory

Destekleyen Kurum

Sinop University

Proje Numarası

1901. 14-05, 2015.

Teşekkür

This work was supported by Sinop University Scientific Research Coordination Unit

Kaynakça

• [1] F. Comelli, S. Ottani, R. Francesconi, and C. Castellari, “Densities, viscosities, and refractive indices of binary mixtures containing n-hexane+ components of pine resins and essential oils at 298.15 K,” Journal of Chemical & Engineering Data, vol. 47, pp. 93-97, 2002.
• [2] E. J. L. Lana, K. A. da Silva Rocha, I. V. Kozhevnikov, and E. V. Gusevskaya, “Synthesis of 1, 8-cineole and 1, 4-cineole by isomerization of α-terpineol catalyzed by heteropoly acid,” Journal of Molecular Catalysis A: Chemical, vol. 259, pp. 99-102, 2006.
• [3] S. Pattnaik, V. R. Subramanyam, M. Bapaji, and C. R. Kole, “Antibacterial and antifungal activity of aromatic constituents of essential oils”, Microbios, vol. 89, pp. 39, 1997.
• [4] E. A. Laude, A. H. Morice, and T. J. Grattan, “The antitussive effects of menthol, camphor and cineole in conscious guinea-pigs. Pulmonary pharmacology,” vol. 7, pp. 179-184, 1994.
• [5] S. Gao, and J. Singh, “In vitro percutaneous absorption enhancement of a lipophilic drug tamoxifen by terpenes,” Journal of controlled release, vol. 51, pp. 193-199, 1998.
• [6] H. Moteki, H. Hibasami, Y. Yamada, H. Katsuzaki, K. Imai, and T. Komiya, “Specific induction of apoptosis by 1, 8-cineole in two human leukemia cell lines, but not a in human stomach cancer cell line,” Oncology reports, vol. 9, pp. 757-760, 2002.
• [7] S. Aparicio, R. Alcalde, M. J. Dávila, B. García, and J. M. Leal, “Properties of 1, 8-cineole: a thermophysical and theoretical study,” The Journal of Physical Chemistry B, vol. 111, pp. 3167-3177, 2007.
• [8] M. Baranska, H. Schulz, S. Reitzenstein, U. Uhlemann, M. A. Strehle, H. Krüger, ... and J. Popp, “Vibrational spectroscopic studies to acquire a quality control method of Eucalyptus essential oils,” Biopolymers: Original Research on Biomolecules, vol. 78, pp. 237-248, 2005.
• [9] K. R. Strehle, P. Rösch, D. Berg, H. Schulz, and J. Popp, “Quality control of commercially available essential oils by means of Raman spectroscopy,” Journal of agricultural and food chemistry, vol. 54, pp. 7020-7026, 2006.
• [10] L. Lawtrakul, K. Inthajak, and P. Toochinda, “Molecular calculations on β-cyclodextrin inclusion complexes with five essential oil compounds from Ocimum basilicum (sweet basil),” Science Asia, vol. 40, pp. 145-151, 2014.
• [11] P. Patel, J. Bhalodia, S. S. Sharma, and P. C. Jha, “Refractive index, speed of sound, FT-IR and computational study of intermolecular interaction between binary mixtures of 1, 8-cineole with o-, m-and pcresol at 303.15, 308.15 and 313.15 K,” Journal of Molecular Liquids, vol. 222, pp. 1192-1211, 2016.
• [12] S. Mandal, K. K. Maiti, A. Banerji, T. Prange, A. Neuman, and N. Acharjee, “Experimental and DFT studies for substituent effects on cycloadditions of C, N-disubstituted nitrones to cinnamoyl piperidine,” 2018.
• [13] S. Prabhakaran, and M. Jaffar, “Vibrational analysis, ab initio HF and DFT studies of 2, 4, 6-trimethyl phenol,” Indian Journal of Pure & Applied Physics, vol. 56, pp. 119-127, 2018.
• [14] R.N. Patel, “Crystal structure, configurational and DFT study of nickel (II) complexes with N 2 O-donor type Schiff base ligand,” Indian Journal of Chemistry-Section A (IJCA), vol. 57, pp. 44-51, 2020.
• [15] J. Andzelm, and E. Wimmer, “Density functional Gaussian‐type‐orbital approach to molecular geometries, vibrations, and reaction energies,” The Journal of chemical physics, vol. 96, pp. 1280-1303, 1992.
• [16] A.D. Becke, “Density-functional exchangeenergy approximation with correct asymptotic behavior,” Physical Review, vol. 38, pp. 3098. 1988.
• [17] C. Lee, W. Yang, and R. G. Parr, “Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density,” Physical review B, vol. 37, pp. 785, 1988.
• [18] Y. Zhao, and D. G. Truhlar, “A new local density functional for main-group thermochemistry, transition metal bonding, thermochemical kinetics, and noncovalent interactions,” The Journal of chemical physics, vol. 125, pp. 194101, 2006.
• [19] Y. Zhao, and D. G. Truhlar, “The M06 suite of density functionals for main group thermochemistry, thermochemical kinetics, noncovalent interactions, excited states, and transition elements: two new functionals and systematic testing of four M06-class functionals and 12 other functionals,” Theoretical Chemistry Accounts, vol. 120, pp. 215-241, 2008.
• [20] E. G. Hohenstein, S. T. Chill, and Sherrill, C. D., “Assessment of the performance of the M05− 2X and M06− 2X exchangecorrelation functionals for noncovalent interactions in biomolecules,” Journal of Chemical Theory and Computation, vol. 4, pp. 1996-2000, 2008.
• [21] A. D. McLean, and G. S. Chandler, “Contracted Gaussian basis sets for molecular calculations. I. Second rowatoms, Z= 11–18,” The Journal of Chemical Physics, vol. 72, 5639-5648, 1980.
• [22] R. Dennington, T. Keith, and J. Millam, “GaussView, Version 5.0.9, Semichem Inc. ,” Shawnee Mission, KS, 2009.
• [23] M. J. Frischa, G. W. Trucks, H. P. Schlegel, G. E. Scuseria, M. A. Robb, and J. R. “Cheesman, Gaussian’09, Gaussian. Inc.,” Wallingford CT, 2009.
• [24] S. F. Boys, and F. J. M. P. Bernardi, “The calculation of small molecular interactions by the differences of separate total energies. Some procedures with reduced errors,” Molecular Physics, vol. 19, pp. 553-566, 1970.
• [25] C. M. Rohlfing, L. C. Allen, and R. Ditchfield, “Proton and carbon-13 chemical shifts: comparison between theory and experiment,” Chemical physics, vol. 87, pp. 9-15, 1984.
• [26] O. Elkiran, and C. Avşar, “Chemical composition and biological activities of the essential oil from the leaves of Vaccinium myrtillus L.,’’ Bangladesh Journal of Botany, vol. 49, pp. 91-96, 2020.
• [27] V. I. Babushok, P. J. Linstrom, and I. G. Zenkevich, “Retention indices for frequently reported compounds of plant essential oils,’’ Journal of Physical and Chemical Reference Data, vol. 40, 043101-47, 2011.
• [28] M. Kürkçüoglu, A. Abdel-Megeed, and K. H. C. Başer, “The composition of Taif rose oil,’’ Journal of Essential Oil Research, vol. 25, pp. 364-367, 2013.
• [29] O. Elkiran, E. Akbaba, and E. Bagci, “Constituents of essential oils from leaves and seeds of Laurus nobilis L.: a chemotaxonomic approach,’’ Bangladesh Journal of Botany, vol. 47, pp. 893-901, 2018.
• [30] E. Bagci, O. Elkiran, and H. Evren, “Constituents of the essential oils of Helichrysum graveolens (Bieb.) Sweet from Turkey,’’ Asian Journal of Chemistry, vol. 25, pp. 7254-7256, 2013.
• [31] S. Jena, A. Ray, A. Sahoo, B. Kar, P. C. Panda, and S. Nayak, “Chemical constituents of leaf essential oil of Curcuma angustifolia Roxb. growing in eastern India,’’ Journal of Essential Oil Bearing Plants, vol. 19, pp. 1527-1531, 2016.
• [32] L. S. Pinheiro, A. A. de Oliveira Filho, and F. Q. S. Guerra, “Antifungal activity of the essential oil isolated from Laurus nobilis L. against Cryptococcus neoformans strains,” Journal of Applied Pharmaceutical Science, vol. 7, pp. 115-118, 2017.
• [33] M. Riaz, C. M. Ashraf, and F. M. Chaudhary, “Studies on the essential oil of the Pakistani Laurus nobilis Linn. İn different seasons,” Pakistan Journal of Scientific and Industrial Research, vol. 32, pp. 33-35, 1989.
• [34] R. M. Verdian, “Phenological variation of Laurus nobilis L. essential oil from Iran,” Electronic Journal of Environmental, Agricultural and Food Chemistry, vol. 7, pp. 3321-3325, 2008.
• [35] H. Marzouki, A. Piras, B. Marongiu, A. Rosa, and M. A. Dessì, “Extraction and separation of volatile and fixed oils from berries of Laurus nobilis L. by supercritical CO2,” Molecules, vol. 13, pp. 1702-1711, 2008.
• [36] H. Yalçın, M. Anık, M. A. Şanda, and A. Çakır, “Gas chromatography/massspectrometry analysis of Laurus nobilis essential oil composition of northern Cyprus,” Journal of medicinal food, vol. 10, pp. 715-719, 2007.
• [37] B. Yılmaz, and İ. Deniz, “The Effects of cultivation area and altitude variation on the composition of essential oil of Laurus nobilis L. grown in eastern, Western and Central Karadeniz Region,” International Journal of Secondary Metabolite, vol. 4, pp. 187-194, 2017.
• [38] L. Caputo, F. Nazzaro, L. F. Souza, L. Aliberti, L. De Martino, F. Fratianni,... and V. De Feo, “Laurus nobilis: Composition of essential oil and its biological activities,” Molecules, vol. 22, pp. 930, 2017.
• [39] C. Ramos, B. Teixeira, I. Batista, O. Matos, C. Serrano, N. R. Neng, J.M.F. Nogueira, M.L. Nunesand and A. Marques, “Antioxidant and antibacterial activity of essential oil and extracts of bay laurel Laurus nobilis Linnaeus (Lauraceae) from Portugal,” Natural Product Research, vol. 26, pp. 518-529, 2012.
• [40] K. K. Chahal, M. Kaur, U. Bhardwaj, N. Singla and A. Kaur, “A review on chemistry and biological activities of Laurus nobilis L. essential oil, ” Journal of Pharmacognosy and Phytochemistry, vol. 6, pp. 1153-1161, 2017.
• [41] L. R. Peixoto, P. L. Rosalen, G. L. S. Ferreira, I. A. Freires, F. G. de Carvalho, L. R. Castellano, and R. D. de Castro, “Antifungal activity, mode of action and anti-biofilm effects of Laurus nobilis Linnaeus essential oil against Candida spp,” Archives of oral biology, vol. 73, pp. 179-185, 2017.
• [42] A. C. Figueredo, J. G. Barroso, L. G. Pedro, and J. J. C. Scheffer, “Factors affecting secondary metabolite production in plants: volatile and essential oils,” Flavour and Fragrance Journal, vol. 23, pp. 213-226, 2008.
• [43] https://sdbs.db.aist.go.jp/sdbs/cgibin/cre_index.cgi
• [44] T. Sivaranjini, S. Periandy, M. Govindarajan, M. Karabacak, and A. M. Asiri, “Spectroscopic (FT-IR, FT-Raman and NMR) and computational studies on 3-methoxyaniline,” Journal of Molecular Structure, vol. 1056, pp. 176-188, 2014.
• [45] M. Karakaya, and F. Ucun, “H2-Anion Interactions and Energy Calculations for Imidazolium-based Ionic Liquids as Hydrogen Storage Materials,” International Journal of Engineering Technologies, vol. 2, pp. 1-7, 2016.