Araştırma Makalesi
BibTex RIS Kaynak Göster

Hypericin molekülünün Moleküler Yapısı ve Titreşim Frekanlarının Deneysel ve Teorik olarak İncelenmesi

Yıl 2017, , 759 - 769, 08.12.2017
https://doi.org/10.17776/csj.340497

Öz

Bu çalışmada hiperisin molekülünün titreşim
analizi FT-IR spektroskopisi ile deneysel olarak gerçekleştirildi. Aynı
zamanda, hiperisin molekülünün moleküler yapısı, geometrik parametreleri,
titreşim dalgaboyları, moleküler elektrostatik potansiyeli ile en yüksek ve en
düşük dolu orbital (HOMO-LUMO) analizleri Yoğunluk Fonksiyonel Teorisi ile
teorik olarak elde edildi. Titreşim dalgaboylarının literatür verileri ve
mevcut çalışmadan elde edilen deneysel sonuçlarla tutarlı olduğu gözlemlendi. 

Kaynakça

  • [1]. Kasper S., Caraci F., Forti B., Drago F., Aguglia E., Efficacy and tolerability of Hypericum extract for the treatment of mild to moderate depression. Eur Neuropsychopharmacol 2010; 20: 747-65.
  • [2]. Butterweck V., Mechanism of action of St John’s wort in depression: what is known? CNS Drugs 2003; 17(8): 539-62.
  • [3]. Bongiorno P., LoGiudice P., Hypericum for Depression. Nat Med J 2010; 2(12).
  • [4]. Mattace Raso G., Pacilio M., Di Carlo G., Esposito E., Pinto L., Meli R., In-vivo and in-vitro anti-inflammatory effect of Echinacea purpurea and Hypericum perforatum. J Pharm Pharmacol 2002; 54: 1379-83.
  • [5]. Sosa S., Pace R., Bornancin A., Morazzoni P., Riva A., Tubaro A., et al., Topical anti-inflammatory activity of extracts and compounds from Hypericum perforatum L. J Pharm Pharmacol 2007; 59: 703-9.
  • [6]. Galeotti N., Vivoli E., Bilia A.R., Bergonzi M.C., Bartolini A., Ghelardini C., A prolonged protein kinase C-mediated, opioid-related antinociceptive effect of St John's Wort in mice. J Pain 2010; 11: 149-59.
  • [7]. Galeotti N., Vivoli E., Bilia A.R., Vincieri F.F., Bartolini A., Ghelardini C., St John's Wort relieves neuropathic pain through a hypericin-mediated inhibition of the protein kinase C γ and ε activity. Biochem Pharmacol 2010; 79: 1327-36.
  • [8]. Lee J. Y., Duke R. K., Tran V. H., Hook J. M., Duke C. C., Hyperforin and its analogues inhibit CYP3A4 enzyme activity. Phytochemistry 2006; 67: 2550-60.
  • [9]. Siskos M. G., Choudhary M. I., Tzakos A. G., Gerothanassis I. P., 1H NМR chemical shift assignment, structure and conformational elucidation of hypericin with the use of DFT calculations - The challenge of accurate positions of labile hydrogens. Tetrahedron 2016; 72: 8287-93.
  • [10]. Öztürk N., Korkmaz S., Öztürk Y., Wound-healing activity of St. John’s Wort (Hypericum perforatum L.) on chicken embryonic fibroblasts. J Ethnopharmacol 2007; 111: 33-9.
  • [11]. Zhang W., Gong X., Cai Y., Zhang C., Yu X., Fan J., Diao Gu., Investigation of water-soluble inclusion complex of hypericin with β-cyclodextrin polymer. Carbohydrate Polymers 2013; 95: 366-70.
  • [12]. Arsić I., Preparation and Characterization of St. John's Wort Herb Extracts Using Olive, Sunflower and Palm Oils. Acta facultatis medicae Naissensis 2016;33(2): 119-26.
  • [13]. Gîtea D., Şipoş M., Mircea T., Paşca B., The analysis of alcoholic extracts of hypericum specıes by UV/VIS spectrophotometry. Analele Universităţii din Oradea - Fascicula Biologie Tom. 2010; 17 (1): 111-5.
  • [14]. Derun, E. Moroydor., Eslek, Z., Piskin, S., Extraction and Analysis of Hypericum perforatum L. from Turkey. Int J Chem, Mol, Nucl, Mater Metal Eng 2013; 7 (7).
  • [15]. Nikolic G. S., Zlatkovic S. Z., Assaying the variation in secondary metabolites of St.John’s wort for its better use as an antibiotic. J Med Plants Res 2010; 4(3): 211-24.
  • [16]. Hasanein P., Shahidi S., Effects of Hypericum perforatum Extract on Diabetes-induced Learning and Memory Impairment in Rats., Phytother. Res. 2011; 25: 544-9.
  • [17]. Schwob I., Bessiere J.M., Viaro J., Composition of the essential oils of Hypericum perforatum L. from southeastern Franca. C.R.Biologies 2002; 325: 781-5.
  • [18]. Orcic D. Z., Mimica-Dukic N. M., Franciskovic M. M., Petrovic S. S., Jovin E. D., Antioxidant activity relationship of phenolic compounds in Hypericum perforatum L. Chem Centr J 2011; 5: 34.
  • [19]. Andersen D. O., Weber N. D., Wood S. G., Hughes B. G., Murray B. K., North. J. A., In vitro virucidal activity of selected anthraquinones and anthraquinone derivatives. Antiviral Res 1991; 16(2): 185-96.
  • [20]. Barnard D. L., Huffman J. H., Morris J. L., Wood, S. G., Hughes B. G., Sidwell R. W., Evaluation of the antiviral activity of anthraquinones, anthrones and anthra quinone derivatives against human cytomegalovirus. Antiviral Res 1992; 17: 63-77.
  • [21]. Pavlovic M., Tzakou O., Petrakis P.V., Couladis M., The essential oil of Hypericum perforatum L., Hypericum tetrapterum Fries, Hypericumolympicum L. growing in Greece. Flav Fragr J 2006; 21: 84-7.
  • [22]. Wölfle U., Seelinger G., Schempp C. M., Topical Application of St. Johnʼs Wort (Hypericum perforatum). Planta Med 2014; 80: 109-20.
  • [23]. Becke A.D. Density‐functional thermochemistry. III. The role of exact exchange, J. Chem. Phys. 1993; 98: 5648-52.
  • [24]. Lee C., Yang W., Parr R.G. Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density, Phys Rev 1988; B 37: 785-9.
  • [25]. Frish A., Nielsen A. B., Holder A. J., Gauss View User Manual, Gaussian Inc., Pittsburg, PA, 2001.
  • [26]. Frisch M.J., Trucks G.W., Schlegel H.B., et al., Gaussian 09, Revision, A.1, Gaussian Inc., Wallingford CT, 2009.
  • [27]. Gaussian website, Visualizing Molecules&Reactions with Gaussview 5. Available at: http://www.gaussian.com/g_prod/gv5.htm. Retrieved August 10 2016.
  • [28]. Shankar R.Y.B., Prasad M.V.S., Udaya S.N., Veeraiah V. Vibrational (FT-IR, FT-Raman) and UV–Visible spectroscopic studies, HOMO–LUMO, NBO, NLO and MEP analysis of Benzyl (imino (1H-pyrazol-1-yl) methyl) carbamate using DFT calculaions, J Mol Str 2016; 1108: 567-82.
  • [29]. Keresztury G., Holly S., Besenyei G., Varga J., Wang A., Durig J.R. Vibrational spectra of monothiocarbamates-II. IR and Raman spectra, vibrational assignment, conformational analysis and ab initio calculations of S-methyl-N,N-dimethylthiocarbamate, Spectro Acta A 1993; 49: 2007-2017.
  • [30]. Keresztury G., in: Chalmers J.M., Griffith P.R. (Eds), Raman Spectroscopy: Theory in Hand book of Vibrational Spectroscopy, Vol. 1, New York: John Wiley & Sons Ltd., 2002.
  • [31]. Chocholousova J., Vladimir S.V. Hobza P., First local minimum of the formic acid dimer exhibits simultaneously red-shifted O–H⋯O and improper blue-shifted C–H⋯O hydrogen bonds, Chem Phys 2004; 6: 37-41.
  • [32]. Sundaraganesan N., Ilakiamani S., Saleem H., Wojciechowski P. M., Michalska D., Spectrochim. Acta A 2005; 61: 2995-3001.
  • [33]. Gökçe H., Öztürk, N., Taşan, M., Bingöl Alpaslan, Y., Alpaslan, G. Spectroscopic characterization and quantum chemical computations of the 5-(4-pyridyl)-1H-1,2,4-triazole-3-thiol molecule, Spectroscopy Letters 2016; 49, 167-179.
  • [34]. Patel U. H., Gandhi S.A., Patel B. D., Modh R.D., Patel R.H., Yadav J., Desai K. R., Synthesis, characterizations, molecular structure and DFT studies of 4-benzylidene-2-(2-chloro-phenyl)-5-methyl-2,4-dihydro-pyrazol-3-one. Ind J Pure & Appl Phys 2013; 51: 819-26.
  • [35]. Roeges N.P.G., A Guide to the Complete Interpretation of Infrared Spectra of Organic Structures, New York: Wiley, 1994.
  • [36]. Ambujakshan K.R., Madhavan V.S., Varghese H.T., Panicker C.Y., Temiz A. O., Tekiner G. B., Yildiz I., Spectrochim Acta 2008; 69A: 782.
  • [37]. Varsanyi G., Assignments for Vibrational Spectra of Seven Hundred Benzene Derivatives, Vol. I & II, Budapest: Academic Kiaclo, 1973.
  • [38]. Smith B., Infrared Spectral Interpretation-a Systematic Way, CRC press, New York, 1999.
  • [39]. Silverstein R. M., Webster F. X., Spectroscopic Identification of Organic Compound, John Willey & Sons, New York, 1998.
  • [40]. Silverstein R.M., Webster F.X., Spectroscopic Identification of Organic Compound, sixth ed., John Willey & Sons, New York, 1998.
  • [41]. Sudha S., Sundaraganesan N., Vanchinathan K., Muthu K., Meenakshisundaram S.P. Spectroscopic (FTIR, FT-Raman, NMR and UV) and molecular structure investigations of 1,5-diphenylpenta-1,4-dien-3-one: A combined experimental and theoretical study, J Mol Struct 2012; 1030: 191-203.
  • [42]. Showalter B. M., Datta, A., Chowdhury P. K., Park J., Bandyopadhyay P., Choudhury P. K., Kesavan S., Zeng Y., Kraus G. A., Gordon M. S., Toscano J. P., Petrich, J. W., Identification of a Vibrational Frequency Corresponding to H-atom Translocation in Hypericin, Photochem. And Photobio. 2001; 74(2): 157-163.
  • [43]. Fukui K. Role of frontier orbitals in chemical reactions, Science 1982; 218: 747-54.
  • [44]. Pearson R.G. Absolute electronegativity and hardness correlated with molecular orbital theory, Proceed Natl Acad Sci.USA 1986; 83: 8440-41.
  • [45]. Asadi Z., Esrafili M.D., Vessally E. Asnaashariisfahani M., Yahyaei S., Khani A., A structural study of fentanyl by DFT calculations, NMR and IR spectroscopy, J Mol Str 2017; 1128: 552-62.
  • [46]. Murray J. S., Sen K., Molecular Electrostatic Potentials Concepts and Applications, Elsevier Science B.V., Amsterdam, The Netherlands, 1996.
  • [47]. Scrocco E., Tomasi J. Electronic molecular structure, reactivity and intermolecular forces: an euristic interpretation by means of electrostatic molecular potentials, J. Adv. Quantum Chem 1978; 11: 115-193.
  • [48]. Luque F.J., Lopez J.M., Orozco M. Perspective on “Electrostatic interactions of a solute with a continuum. A direct utilization of ab initio molecular potentials for the prevision of solvent effects”, Theoret Chem Acc 2000; 103: 343-5.
  • [49]. Politzer P., Murray J. The fundamental nature and role of the electrostatic potential in atoms and molecules, Theor Chem Acc 2002; 108: 134-42.

Experimental and Theoretical Investigations of Molecular Structure and Vibrational Frequencies of Hypericin Molecule

Yıl 2017, , 759 - 769, 08.12.2017
https://doi.org/10.17776/csj.340497

Öz

In the present study, vibrational analysis of
hypericin molecule was experimentally performed using FT-IR spectroscopy. The
molecular structure, geometric parameters, vibrational wavenumbers, molecular
electrostatic potential and the highest and the lowest occupied molecular
orbital analyses of hypericin molecule were theoretically obtained with Density
Functional Theory. The vibrational wavenumbers were consistent with literature
and the experimental data obtained in the current study.
    

Kaynakça

  • [1]. Kasper S., Caraci F., Forti B., Drago F., Aguglia E., Efficacy and tolerability of Hypericum extract for the treatment of mild to moderate depression. Eur Neuropsychopharmacol 2010; 20: 747-65.
  • [2]. Butterweck V., Mechanism of action of St John’s wort in depression: what is known? CNS Drugs 2003; 17(8): 539-62.
  • [3]. Bongiorno P., LoGiudice P., Hypericum for Depression. Nat Med J 2010; 2(12).
  • [4]. Mattace Raso G., Pacilio M., Di Carlo G., Esposito E., Pinto L., Meli R., In-vivo and in-vitro anti-inflammatory effect of Echinacea purpurea and Hypericum perforatum. J Pharm Pharmacol 2002; 54: 1379-83.
  • [5]. Sosa S., Pace R., Bornancin A., Morazzoni P., Riva A., Tubaro A., et al., Topical anti-inflammatory activity of extracts and compounds from Hypericum perforatum L. J Pharm Pharmacol 2007; 59: 703-9.
  • [6]. Galeotti N., Vivoli E., Bilia A.R., Bergonzi M.C., Bartolini A., Ghelardini C., A prolonged protein kinase C-mediated, opioid-related antinociceptive effect of St John's Wort in mice. J Pain 2010; 11: 149-59.
  • [7]. Galeotti N., Vivoli E., Bilia A.R., Vincieri F.F., Bartolini A., Ghelardini C., St John's Wort relieves neuropathic pain through a hypericin-mediated inhibition of the protein kinase C γ and ε activity. Biochem Pharmacol 2010; 79: 1327-36.
  • [8]. Lee J. Y., Duke R. K., Tran V. H., Hook J. M., Duke C. C., Hyperforin and its analogues inhibit CYP3A4 enzyme activity. Phytochemistry 2006; 67: 2550-60.
  • [9]. Siskos M. G., Choudhary M. I., Tzakos A. G., Gerothanassis I. P., 1H NМR chemical shift assignment, structure and conformational elucidation of hypericin with the use of DFT calculations - The challenge of accurate positions of labile hydrogens. Tetrahedron 2016; 72: 8287-93.
  • [10]. Öztürk N., Korkmaz S., Öztürk Y., Wound-healing activity of St. John’s Wort (Hypericum perforatum L.) on chicken embryonic fibroblasts. J Ethnopharmacol 2007; 111: 33-9.
  • [11]. Zhang W., Gong X., Cai Y., Zhang C., Yu X., Fan J., Diao Gu., Investigation of water-soluble inclusion complex of hypericin with β-cyclodextrin polymer. Carbohydrate Polymers 2013; 95: 366-70.
  • [12]. Arsić I., Preparation and Characterization of St. John's Wort Herb Extracts Using Olive, Sunflower and Palm Oils. Acta facultatis medicae Naissensis 2016;33(2): 119-26.
  • [13]. Gîtea D., Şipoş M., Mircea T., Paşca B., The analysis of alcoholic extracts of hypericum specıes by UV/VIS spectrophotometry. Analele Universităţii din Oradea - Fascicula Biologie Tom. 2010; 17 (1): 111-5.
  • [14]. Derun, E. Moroydor., Eslek, Z., Piskin, S., Extraction and Analysis of Hypericum perforatum L. from Turkey. Int J Chem, Mol, Nucl, Mater Metal Eng 2013; 7 (7).
  • [15]. Nikolic G. S., Zlatkovic S. Z., Assaying the variation in secondary metabolites of St.John’s wort for its better use as an antibiotic. J Med Plants Res 2010; 4(3): 211-24.
  • [16]. Hasanein P., Shahidi S., Effects of Hypericum perforatum Extract on Diabetes-induced Learning and Memory Impairment in Rats., Phytother. Res. 2011; 25: 544-9.
  • [17]. Schwob I., Bessiere J.M., Viaro J., Composition of the essential oils of Hypericum perforatum L. from southeastern Franca. C.R.Biologies 2002; 325: 781-5.
  • [18]. Orcic D. Z., Mimica-Dukic N. M., Franciskovic M. M., Petrovic S. S., Jovin E. D., Antioxidant activity relationship of phenolic compounds in Hypericum perforatum L. Chem Centr J 2011; 5: 34.
  • [19]. Andersen D. O., Weber N. D., Wood S. G., Hughes B. G., Murray B. K., North. J. A., In vitro virucidal activity of selected anthraquinones and anthraquinone derivatives. Antiviral Res 1991; 16(2): 185-96.
  • [20]. Barnard D. L., Huffman J. H., Morris J. L., Wood, S. G., Hughes B. G., Sidwell R. W., Evaluation of the antiviral activity of anthraquinones, anthrones and anthra quinone derivatives against human cytomegalovirus. Antiviral Res 1992; 17: 63-77.
  • [21]. Pavlovic M., Tzakou O., Petrakis P.V., Couladis M., The essential oil of Hypericum perforatum L., Hypericum tetrapterum Fries, Hypericumolympicum L. growing in Greece. Flav Fragr J 2006; 21: 84-7.
  • [22]. Wölfle U., Seelinger G., Schempp C. M., Topical Application of St. Johnʼs Wort (Hypericum perforatum). Planta Med 2014; 80: 109-20.
  • [23]. Becke A.D. Density‐functional thermochemistry. III. The role of exact exchange, J. Chem. Phys. 1993; 98: 5648-52.
  • [24]. Lee C., Yang W., Parr R.G. Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density, Phys Rev 1988; B 37: 785-9.
  • [25]. Frish A., Nielsen A. B., Holder A. J., Gauss View User Manual, Gaussian Inc., Pittsburg, PA, 2001.
  • [26]. Frisch M.J., Trucks G.W., Schlegel H.B., et al., Gaussian 09, Revision, A.1, Gaussian Inc., Wallingford CT, 2009.
  • [27]. Gaussian website, Visualizing Molecules&Reactions with Gaussview 5. Available at: http://www.gaussian.com/g_prod/gv5.htm. Retrieved August 10 2016.
  • [28]. Shankar R.Y.B., Prasad M.V.S., Udaya S.N., Veeraiah V. Vibrational (FT-IR, FT-Raman) and UV–Visible spectroscopic studies, HOMO–LUMO, NBO, NLO and MEP analysis of Benzyl (imino (1H-pyrazol-1-yl) methyl) carbamate using DFT calculaions, J Mol Str 2016; 1108: 567-82.
  • [29]. Keresztury G., Holly S., Besenyei G., Varga J., Wang A., Durig J.R. Vibrational spectra of monothiocarbamates-II. IR and Raman spectra, vibrational assignment, conformational analysis and ab initio calculations of S-methyl-N,N-dimethylthiocarbamate, Spectro Acta A 1993; 49: 2007-2017.
  • [30]. Keresztury G., in: Chalmers J.M., Griffith P.R. (Eds), Raman Spectroscopy: Theory in Hand book of Vibrational Spectroscopy, Vol. 1, New York: John Wiley & Sons Ltd., 2002.
  • [31]. Chocholousova J., Vladimir S.V. Hobza P., First local minimum of the formic acid dimer exhibits simultaneously red-shifted O–H⋯O and improper blue-shifted C–H⋯O hydrogen bonds, Chem Phys 2004; 6: 37-41.
  • [32]. Sundaraganesan N., Ilakiamani S., Saleem H., Wojciechowski P. M., Michalska D., Spectrochim. Acta A 2005; 61: 2995-3001.
  • [33]. Gökçe H., Öztürk, N., Taşan, M., Bingöl Alpaslan, Y., Alpaslan, G. Spectroscopic characterization and quantum chemical computations of the 5-(4-pyridyl)-1H-1,2,4-triazole-3-thiol molecule, Spectroscopy Letters 2016; 49, 167-179.
  • [34]. Patel U. H., Gandhi S.A., Patel B. D., Modh R.D., Patel R.H., Yadav J., Desai K. R., Synthesis, characterizations, molecular structure and DFT studies of 4-benzylidene-2-(2-chloro-phenyl)-5-methyl-2,4-dihydro-pyrazol-3-one. Ind J Pure & Appl Phys 2013; 51: 819-26.
  • [35]. Roeges N.P.G., A Guide to the Complete Interpretation of Infrared Spectra of Organic Structures, New York: Wiley, 1994.
  • [36]. Ambujakshan K.R., Madhavan V.S., Varghese H.T., Panicker C.Y., Temiz A. O., Tekiner G. B., Yildiz I., Spectrochim Acta 2008; 69A: 782.
  • [37]. Varsanyi G., Assignments for Vibrational Spectra of Seven Hundred Benzene Derivatives, Vol. I & II, Budapest: Academic Kiaclo, 1973.
  • [38]. Smith B., Infrared Spectral Interpretation-a Systematic Way, CRC press, New York, 1999.
  • [39]. Silverstein R. M., Webster F. X., Spectroscopic Identification of Organic Compound, John Willey & Sons, New York, 1998.
  • [40]. Silverstein R.M., Webster F.X., Spectroscopic Identification of Organic Compound, sixth ed., John Willey & Sons, New York, 1998.
  • [41]. Sudha S., Sundaraganesan N., Vanchinathan K., Muthu K., Meenakshisundaram S.P. Spectroscopic (FTIR, FT-Raman, NMR and UV) and molecular structure investigations of 1,5-diphenylpenta-1,4-dien-3-one: A combined experimental and theoretical study, J Mol Struct 2012; 1030: 191-203.
  • [42]. Showalter B. M., Datta, A., Chowdhury P. K., Park J., Bandyopadhyay P., Choudhury P. K., Kesavan S., Zeng Y., Kraus G. A., Gordon M. S., Toscano J. P., Petrich, J. W., Identification of a Vibrational Frequency Corresponding to H-atom Translocation in Hypericin, Photochem. And Photobio. 2001; 74(2): 157-163.
  • [43]. Fukui K. Role of frontier orbitals in chemical reactions, Science 1982; 218: 747-54.
  • [44]. Pearson R.G. Absolute electronegativity and hardness correlated with molecular orbital theory, Proceed Natl Acad Sci.USA 1986; 83: 8440-41.
  • [45]. Asadi Z., Esrafili M.D., Vessally E. Asnaashariisfahani M., Yahyaei S., Khani A., A structural study of fentanyl by DFT calculations, NMR and IR spectroscopy, J Mol Str 2017; 1128: 552-62.
  • [46]. Murray J. S., Sen K., Molecular Electrostatic Potentials Concepts and Applications, Elsevier Science B.V., Amsterdam, The Netherlands, 1996.
  • [47]. Scrocco E., Tomasi J. Electronic molecular structure, reactivity and intermolecular forces: an euristic interpretation by means of electrostatic molecular potentials, J. Adv. Quantum Chem 1978; 11: 115-193.
  • [48]. Luque F.J., Lopez J.M., Orozco M. Perspective on “Electrostatic interactions of a solute with a continuum. A direct utilization of ab initio molecular potentials for the prevision of solvent effects”, Theoret Chem Acc 2000; 103: 343-5.
  • [49]. Politzer P., Murray J. The fundamental nature and role of the electrostatic potential in atoms and molecules, Theor Chem Acc 2002; 108: 134-42.
Toplam 49 adet kaynakça vardır.

Ayrıntılar

Bölüm Natural Sciences
Yazarlar

Tuba Özdemir

Halil Gökçe

Yayımlanma Tarihi 8 Aralık 2017
Gönderilme Tarihi 31 Ocak 2017
Kabul Tarihi 17 Temmuz 2017
Yayımlandığı Sayı Yıl 2017

Kaynak Göster

APA Özdemir, T., & Gökçe, H. (2017). Experimental and Theoretical Investigations of Molecular Structure and Vibrational Frequencies of Hypericin Molecule. Cumhuriyet Science Journal, 38(4), 759-769. https://doi.org/10.17776/csj.340497