Vibrational spectral analysis and theoretical ınvestıgatıon on the molecular structure of ACACETIN (5,7-dihydroxy-4'-methoxyflavone)

Year 2016, Volume: 20 Issue: 3, 543 - 558, 01.12.2016

Tevfik Raci Sertbakan , Ökkeş Gözdaş

https://doi.org/10.16984/saufenbilder.67441

Abstract

Acacetin (5,7-dihydroxy-4'-methoxyflavone) which is naturally a flavone compounds presents in plants, has anti-cancer and anti-inflammatory activities. Neuroinflammation is thought to be one of the major pathological mechanisms responsible for Parkinson's disease (PD), and has been a primary target in the development of treatment for PD. In this study, conformational search of the acacetin molecule has been performed. The FT-IR spectrum of this compound was recorded in the region 4000–400 cm-1. The FT-Raman spectrum was also recorded in the region 3500–50 cm-1. Vibrational frequencies of the title compound have been calculated by B3LYP with cc-pVDZ and cc-pVTZ basis sets. The calculations were performed at DFT levels by using Gaussian 09W program package, by invoking gradient geometry optimization. The calculated geometric parameters and vibrational frequencies were analyzed and compared with obtained experimental results.

Keywords

Acacetin, Flavone, FT-IR, FT-Raman, Density functional theory, Total energy distribution

ACACETIN’İN (5,7-dihydroxy-4'-methoxyflavone) moleküler yapisinda titreşimsel spektral analizler ve teorik inceleme

Abstract

Bitkilerde doğal olarak mevcut bir flavon bileşiğiolan Acacetin (5,7-dihydroxy-4'-methoxyflavone) anti-kanser ve anti-iltihap aktivitelere sahiptir. Nöroiltihabın Parkinson hastaları (PD) için güvenilir başlıca patolojik meknizmalardan biri olduğu düşünülmektedir ve PD için tedavi gelişiminde bir ana hedef olmuştur. Bu çalışmada, acacetinin molekülünün konformasyon araştırması yapılmıştır. Bu bileşiğin FT-IR spektrumu  4000–400 cm-1 bölgesinde kaydedilmiştir. FT-Raman spektrumu da 3500–50 cm-1 bölgesinde kaydedilmiştir. Başlık bileşiğinin titreşim frekansları B3LYP metodu cc-pVDZ ve cc-pVTZ temel setlerinde hesaplanmıştır. Bu hesaplamalar, gradyent geometri optimizasyonu yardımıyla Gaussian 09W paket programı kullanılarak DFT seviyelerinde gerçekleşmiştir. Titreşim frekanslarının ve geometrik parametrelerin hesaplamaları analiz edilmiş ve deneysel sonuçlar ile karşılaştırılmıştır.   

Keywords

Acacetin, flavon, FT-IR, FT-Raman, Yoğunluk fonksiyonu teorisi, Toplam enerji dağılımı

References

• REFERENCES
• P. J. A. Madeira, C. M. Borges and M. H. Florencio, Rapid Communic. Mass Spect., 24, 3432–3440, (2010).
• Y. S. Touil, A. Fellous, D. Scherman and G. G. Chabot, Nutrition and Cancer, 61 (3), 310–321, (2009).
• M. H. Pan, C. S. Lai, P. C. Hsu and Y. J. Wang, J. Agric. Food Chem., 53, 620–630, (2005).
• Shang-Tao Chien, Su-Shun Lin, Cheng-Kun Wang, Yuan-Bin Lee, Kun-Shiang Chen, Yao Fong,Yuan-Wei Shih, Mol Cell Biochem., 350, 135–148, (2011).
• Kim HG, Ju MS, Ha SK, Lee H, Lee H, Kim SY, Oh MS. , Biol Pharm Bull., 35(8), 1287–1294, (2012).
• Kun-Hung Shen, Shun-Hsing Hung , Li-Te Yin , Chun-Shui Huang , Chang-Hung Chao , Chein-Liang Liu , Yuan-Wei Shih, Mol Cell Biochem., 333, 279–291, (2010).
• T. Teslova, C. Corredor, R. Livingstone, T. Spataru, R. L. Birke, J. R. Lombardi, M. V. Canamares and M. Leona, J. Raman Spect., 38, 802, (2007).
• A. Vavra, R. Linder, K. Kleinermanns, Chem. Phys. Lett., 463, 349,(2008).
• A. Mantas, E. Deretey, F. H. Ferretti, M. Estrada, I. G. Csizmadia, J. Mol. Struct. (Theo.), 504, 77, (2000).
• L. Vrielynck, J. P. Cornard, J. C. Merlin and M. F. Lautie, Spectrochim. Acta A, 50, 2177, (1994).
• Y. Erdoğdu, O. Ünsalan and M. T. Güllüoğlu, Turk J. Phys., 33, 249–259, (2009).
• M. J. Frisch, et all., Gaussian 03, Revision C.02, Gaussian, Inc., Wallingford, CT, (2004).
• H. B. Schlegel, J. Comput. Chem., 3, 214–218, (1982).
• Ö. Dereli et al. , J.Mol.Struct., 1012, 168–176, (2012).
• M. P. Waller, D. E. Hibbs, J. Overgaard, J. R. Hanrahanand T. W. Hambley, Acta Crystallographica Section E, 59, 767, (2003).
• B. J. Hall, J. R. Hanrahan G. A. R. Johnston, T. W. Hambley and D. E. Hibbs, Acta Crystallographica Section E, 57, 592, (2001).
• Gauss View, Version 4.01, Dennington II, Roy, T. Keith, J. Millam, K. Eppinnett, W. L.Hovell, R. Gilliland, Semichem, Inc.,Shawnee Mission, KS, (2003).
• G. Rauhut, P. Pulay, J. Phys. Chem., 99, 3093, (1995).
• P. Pulay and F. Török, ActaChimica Acad. Sci. Hung., 47, 273, (1965).
• H. Saleem, Y. Erdoğdu, S. Subashchandrabose, Ö. Dereli, V. Thanikachalam and J. Jayabharathi, Spectrochimica Acta Part A, 86, 231–241, (2012).
• I. Fleming, Frontier Orbitals and Organic Chemical Reactions, John Wiley and Sons, New York, (1976).
• G.Gece, Theuse of quantum chemical methods in corrosion inhibitor studies. Corrosion Science., 50, 2981-2992, (2008).
• K.Fukui, Theory of Orientation and Stereo Selection. Springer-Verlag, Berlin, (1975).
• S.Muthu, E. Elamurugu Porchelvi, FTIR, FT-Raman, NMR, spectra, normal co-ordinate analysis, NBO, NLO and DFT calculation of N,N-diethyl-4-methyl-piperazine-1-carboxamide molecule, 115, 275-286, (2013).