Naringenin’in Çözücü Ortamlardaki Yapısal-Spektroskopik Özellikleri ve Antioksidan Aktivite Çalışmaları

Abstract

Bu çalışmada, naringenin yapısal ve spektroskopik özellikleri üzerine çözücü etkileri araştırılmıştır. Naringenin’in geometrik parametreleri hesaplanmış ve deneysel X-ışını kristalografik verisi ile karşılaştırılmıştır. Ek olarak, çözücü ortamında optimize edilmiş yapılar elde edilerek, çözücülerin geometrik parametreler üzerindeki etkileri belirlendi. Vakumda ve çözücü ortamlarda elde edilen titreşim modları deneysel IR spektrumu ile karşılaştırıldı. Ayrıca, HOMO-LUMO enerjileri ve kimyasal reaktivite de belirlendi. Naringenin antioksidan aktivitesi, -OH gruplarından hidrojen atomu soyutlaması ile araştırıldı. Bağ ayrışma entalpileri hesaplandı ve bu sürecin naringenin antioksidan aktivitesinin ana mekanizması olması gerektiği belirlendi. Hesaplama sonuçlarına göre şaşırtıcı bir şekilde, DMSO'da naringenin BDE değerlerinin önemli ölçüde azaldığı ve dolayısıyla antioksidan aktivitenin diğer ortamlara göre arttığı belirlendi.

Keywords

• Naringenin,Çözücü Etkileri,YFT,Kimyasal reaktivite

Structural-Spectroscopic Properties and Antioxidant Activity Studies of Naringenin in Solvent Media

Abstract

In this study, solvent effects on the structural and spectroscopic properties of the naringenin have been investigated. Geometric parameters were calculated and were compared with the experimental X-ray crystallographic data. In addition, optimized structures were obtained in solvent media and the solvents effects on geometric parameters were determined. Vibrational modes obtained in the vacuum and in solvent environments were compared with the experimental IR spectrum. Furthermore, the HOMO-LUMO energies and chemical reactivity were also determined. Antioxidant activity of naringenin has been investigated with hydrogen atom abstraction from −OH groups. The bond dissociation enthalpies have been calculated and it is determined that this process should be the main mechanism for the antioxidant activity of naringenin. According to the calculation results, surprisingly, it has been found that in DMSO, BDE values of naringenin are significantly reduced and thus antioxidant activity is increased compared to other media.

Keywords

• Naringenin,Solvent effects,DFT,Chemical reactivity

References

1. Alam MA, Subhan N, Rahman MM, Uddin SJ, Reza HM, Sarker SD, 2014. Effect of Citrus Flavonoids, Naringin and Naringenin, on Metabolic Syndrome and Their Mechanisms of Action, Advances in Nutrition. 5: 404–417.
2. Bao L, Liu F, Guo HB, Li Y, Tan BB, Zhang WX, Peng Y, 2016. Naringenin inhibits proliferation, migration, and invasion as well as induces apoptosis of gastric cancer SGC7901 cell line by downregulation of AKT pathway. Tumor Biology. 37: 11365–11374.
3. Bilkan MT, Şahin O, Yurdakul Ş, 2017. Experimental and DFT studies of solvent effects on molecular structure and physical properties of Dipyridylamine pyridine based ligand, Journal of Molecular Structure. 1133: 580-590.
4. Cavia-Saiz M, Busto MD, Pilar-Izquierdo MC, Ortega N, Perez-Mateos M, Muñiz P, 2010. Antioxidant properties, radical scavenging activity and biomolecule protection capacity of flavonoid naringenin and its glycoside naringin: a comparative study. Journal of the Science of Food and Agriculture, 90: 1238-1244.
5. Choi C, Kertez M, Conformational information from vibrational spectra of styrene, trans-stilbene, and cis-stilbene, Journal of Physical Chemistry A, 101: 3823–3831.
6. Dennington RD, Keith TA, Millam JM, 2008. GaussView 5, Gaussian, Inc.
7. Frabasile S, Koishi AC, Kuczera D, Silveira GF, Verri Jr WA, dos Santos CND, Bordignon J, 2017. The citrus flavanone naringenin impairs dengue virus replication in human cells. Scientific Reports-Nature. 7:41864-41874.
8. Frisch MJ, Trucks GW, Schlegel HB, et al. 2004. Gaussian, Inc., Gaussian 03, Revision D.01. Wallingford CT.

9. Fuhr U, Klittich K, Horst Staib A, 1993. Inhibitory effect of grapefruit juice and its bitter principal, naringenin, on CYP1A2 dependent metabolism of caffeine in man. British Journal of Clinical Pharmacology. 35:431-436.
10. Ghofrani S, Joghataei MT, Mohseni S, Baluchnejadmojarad T, Bagheri M, Khamse S, Roghani M, 2015. Naringenin improves learning and memory in an Alzheimer's disease rat model: Insights into the underlying mechanisms. European Journal of Pharmacology. 5:195-201.
11. Gonzales GB, Smagghe G, Wittevrongel J, Huynh NT, Van Camp J, Raes K, 2016. Metabolism of Quercetin and Naringenin by Food-Grade Fungal Inoculum, Rhizopus azygosporus Yuan et Jong (ATCC 48108). Journal of Agricultural Food Chemistry 49: 9263-9267.
12. Jamróz MH, 2004. Vibrational energy distribution analysis. VEDA 4. Warsaw.
13. Lee SY, Boo BH, 1996. Molecular Structures and Vibrational Spectra of Pyrrole and Carbazole by Density Functional Theory and Conventional ab Initio Calculations, Journal of Physical Chemistry A. 100: 15073-15078.
14. Parr RG, Szentpa´Ly LV, Liu S, 1999. Electrophilicity Index, Journal of American Chemical Society, 121: 1922–1924.
15. Pauling L, 1960. The nature of the chemical bond, (Cornell University Press).
16. PC H, Saville DJ, 2001. Inhibition of human CYP3A4 activity by grapefruit flavonoids, furanocoumarins and related compounds. Journal of Pharmacy & Pharmaceutical Sciences. 4: 217-227.
17. Saqib M, Iqbal S, Mahmood A, Akram R, 2015. Theoretical Investigation for Exploring the Antioxidant Potential of Chlorogenic Acid: A Density Functional Theory Study, International Journal of Food Properties, 19: 745-751.
18. Shin W, Lah MS, 1986. Structure of (R,S)-naringenin, Acta. Crystallographica C, 42: 626-627.
19. Swanson BN, 1985. Medical use of dimethyl sulfoxide (DMSO).Reviews in Clinical & Basic Pharmacology. 5: 1-33.
20. Tomasi J, Mennucci B, Cammi R, 2005. Quantum mechanical continuum solvation models, Chemical Reviews. 105: 2999–3094.
21. Unsalan O, Erdogdu Y, Gulluoglu MT, 2009. FT-Raman and FT-IR spectral and quantum chemical studies on some flavonoid derivatives: Baicalein and Naringenin, Journal of Raman Spectroscopy. 40: 562–570.
22. Zhang L, Song L, Zhang P, Liu T, Zhou L, Yang G, Lin R, Zhang J, 2015. Solubilities of Naringin and Naringenin in Different Solvents and Dissociation Constants of Naringenin, Journal of Chemical & Engineering Data. 60: 932−940.
23. Zhang P, Lin R, Yang G, Zhang J, Zhou L, Liu T, 2013. Solubility of Naringenin in Ethanol and Water Mixtures, Journal of Chemical & Engineering Data. 58: 2402−2404.