Bazı Fenolik Bileşiklerin Yoğunluk Fonksiyonu Yöntemi ile Antioksidan Aktivitelerinin Tayin Edilmesi

Year 2019, Volume: 23 Issue: Special [en], 139 - 146, 01.03.2019

Vildan Enisoğlu Atalay , Hatice Ocak

https://doi.org/10.19113/sdufenbed.439631

Cited By: 1

Abstract

Oksidatif stresin başta kanser olmak üzere
ateroskleroz, hipertansiyon ve kardiyovasküler hastalıklar gibi pek çok
hastalığın patogenezinde rol oynadığı çeşitli araştırmalar sonucunda
görülmüştür. Fenolik bileşikler ise insan sağlığı bakımından antioksidan
fonksiyonları ile ön plana çıkan maddelerdir. Fenolik antioksidanların serbest
radikaller ile reaksiyona girme eğilimi antioksidan aktiviteyi tanımlamaktadır.
Bu çalışmada 10 adet fenolik bileşik gaz etanol ve su fazlarında Spartan 14 programı ile DFT//B3LYP metodu ve 6–31+G(d) temel seti ile HAT, SET-PT ve SPLET oksidasyon mekanizmaları gaz, su ve etanol
fazlarında modellenmiştir. Elde edilen verilere göre BDE, ETE, PA, IP, PDE ve
Δ(E_HOMO-E_LUMO) değerleri hesaplanarak antioksidan aktiviteleri sıralanmıştır. Yapılan hesaplamalardan elde edilen tüm sonuçlar değerlendirildiğinde bileşik 1
olarak tanımlanan 2-hexadecyl-2,5,7,8-tetramethylchroman-6-ol molekülünün
antioksidan aktivitesi çalışılan yöntem ve fazlarda en yüksek olarak
bulunmuştur.

Keywords

B3LYP, HAT, SET-PT, SPLET, Antioksidan aktivite, DFT

Determination of Antioxidant Activities by Density Function Method of Some Phenolic Compounds

Abstract

Oxidative
stress is implicated in various disease pathologies including cancer,
atherosclerosis, hypertension, and cardiovascular disease. Phenolic compounds
have antioxidant functions in terms of human health. The tendency of phenolic
antioxidants to react with free radicals identifies their antioxidant activity.
In this study, HAT, SET-PT and SPLET oxidation mechanisms were modeled in the
gas, water and ethanol phases with the DFT // B3LYP method and 6-31+G(d) basis
set with 10 phenolic compounds using Spartan 14. Antioxidant activities were
ranked by calculated BDE, ETE, PA, IP, PDE and Δ(E_HOMO-E_LUMO)
values ​​according to the obtained data. The antioxidant activity of
2-hexadecyl-2,5,7,8-tetramethylchroman-6-ol, identified as compound 1, was
found to be highest in the methods and phases studied when all the results
obtained from the calculations made were evaluated.

Keywords

B3LYP, Antioxidant activity, HAT, SET-PT, SPLET, DFT

References

• [1] Özcan, O., Erdal, H., Çakırca, G., Yönden, Z. 2015. Oksidatif Stres ve Hücre İçi Lipit, Protein ve DNA Yapıları Üzerine Etkileri. Journal of Clinical and Experimental Investigations, 6 (2015) 331-336.
• [2] Reed, D.J. 1995. Toxicity of Oxygen in Molecular And Cellular Mechanisms of Toxicity. CRC Press, 35–68, Boca Raton- USA.
• [3] Younes, M. 1999. Free Radicals and Reactive Oxygen Species, in Toxicology, ‘By H. Marguardt, Mechanisms of Antioxidant and Pro-Oxidant Effects of Lipoic Acid in the Diabetic and Nondiabetic Kidney’. Kidney International, 67 (1999), 1371 – 1380.
• [4] Berlett, B.S., Stadtman, ER. 1997. Protein Oxidation in Aging, Disease and Oxidative Stress. The Journal of Biological Chemistry, 272 (1997): 20313-6.
• [5] Şahin, D.Y., Elbasan, Z., Gür, M., Türkoğlu, C., Özaltun, B., Sümbül, Z., Çaylı, M. 2012. Relationship Between Oxidative Stress Markers and Cardiac Syndrome X. Journal of Clinical and Experimental Investigations, 3 (2012): 174-180.
• [6] Zhang, H.Y. 1999. Theoretical Elucidation of Structure-Activity Relationships of Flavonoid Antioxidants, Science in China (series B) 42 (1999), 106–112.
• [7] Shahidi, F., Naczk, M., 1995. Food Phenolics; Technomic Publishing:Lancaster, PA,
• [8] Zhang, H. Y. 1998. Selection of Theoretical Parameter Characterizing Scavenging Activity of Antioxidants on Free Radicals, J. Am. Oil Chem. Soc. 75 (1998), 1705–1709.
• [9] Lu, L., Qiang, M., Li, F., Zhang, H., Zhang, S., 2014. Theoretical Investigation on the Antioxidative Activity of Anthocyanidins: A DFT/B3LYP Study. Dyes And Pigments, 103(2014), 175–182.
• [10] Nenadis, N., Sigalas, M. P. 2011. A DFT Study on the Radical Scavenging Potential of Selected Natural 3′,4′-Dihydroxy Aurones. Food Research International, 44 (2011), 114-120.
• [11] Urbaniak, A., Molski, M., Szelag, M., 2012. Quantum-Chemical Calculations of the Antioxidant Properties of Trans-P-Coumaric Acid and Trans-Sinapinic Acid. Computational Methods in Science And Technology, 18 (2012), 117-128.
• [12] Stewart, J. J. P. 2008. Application of the PM6 method to modeling the solid state, J Mol Model. 14 (2008): 499–535
• [13] Stewart, J. J. P. 2009. Application of the PM6 method to modeling proteins, J Mol Model. 15, 7(2009), 765–805
• [14] Spartan 14v112 (2013) Wavefunction, Inc., Irvine.
• [15] Dennington R, Keith T, Millam J. GaussView, Version 5, Semichem Inc., Shawnee Mission KS, 2009.
• [16] Hehre, W. J. 2003. A Guide to Molecular Mechanics and Quantum Chemical Calculations, Wavefunction, Inc., Irvine, CA.
• [17] Frisch, M. J. “Gaussian 09”, Gaussian, Inc, 2009. Version 6.
• [18] Axel, D. B. 1993. A new mixing of Hartree–Fock and local density‐functional theories. The Journal of Chemical Physics 98(1993), 1372.
• [19] Petersson, G. A., Bennett, A., Tensfeldt, T. G., Al-Laham, M. A., Shirley, W. A., Mantzaris, J. 1988. A complete basis set model chemistry. I. The total energies of closed-shell atoms and hydrides of the first-row atoms, J. Chem. Phys., 89 (1988), 2193-218.
• [20] Zheng, Y.Z., Deng, G., Liang, Q., Chen, D.F., Guo, R., Lai, R.C. 2017. Antioxidant Activity of Quercetin and Its Glucosides From Propolis: A Theoretical Study. Scientific Reports, 7(2017), 7543.
• [21] Weirong, C., Yong, C., Liangliang, X., Hong, Z., Chunyuan, H. 2014. Characterization and density functional theory study of the antioxidant activity of quercetin and its sugar-containing analogues, Eur Food Res Technol, 238 (2014), 121–128.
• [22] Al-Majedy, Y. K., Al-Amiery, A. A., Kadhum, A. H., Mohamad, A. B. 2016. Antioxidant Activities of 4- Methylumbelliferone Derivatives, PLoS One. 11 (2016), 5.
• [23] Praveena, R., Sadasivam, K., Kumaresan, R., Deepha, V, Sivakumar R. 2013. Experimental and DFT studies on the antioxidant activity of a C-glycoside from Rhynchosia capitata, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 103 (2013), 442–452.
• [24] Praveena, R., Sadasivam, K., Kumaresan, R., Deepha, V, Sivakumar R., Zheng, Y. Z., Deng G., Liang, Q., Chen, D., Guo, R., Rong-Cai, L., 2013, Antioxidant Activity of Quercetin and Its Glucosides from Propolis: A Theoretical Study, Scientific Reports, 7(2013), 7543.