Nurgül KARADAŞ, Zeynep KALAYCIOĞLU, Mehmet Emin ÇINAR, Sibel AYŞIL ÖZKAN, Durişehvar ÖZER ÜNAL, Ayşegül GÖLCÜ, Fatma Bedia BERKER

Electrochemical oxidation of curcuminoids: an experimental and computational investigation

Curcuminoids, reported to have important biological properties, such as antioxidant, anti-Alzheimer, andantidiabetic properties, comprise curcumin (CRM; 1,7-bis [4-hydroxy-3-methoxyphenyl]-1,6-heptadiene-3,5-dione) and its derivatives demethoxycurcumin (DMC; (E,6E)-1-(3,4-dimethoxy-cyclohexyl)-7-(3,4-dimethoxyphenyl)hepta-1,6-diene-3,5- dione) and bisdemethoxycurcumin (BDMC; 1,7-bis[4-hydroxyphenyl]-1,6-heptadiene-3,5-dione). Their electrochemical oxidations are thoroughly explored by applying cyclic and differential pulse voltammetric techniques. The dependence of current intensities and potentials on pH, concentration, scan rate, and nature of the buffer was investigated. The outcome is supported by density functional theory computations indicating the transfer of 4-e − /H + , 6-e − /H + , and 8-e − /H + couples involved in the oxidation mechanisms of CRM, DMC, and BDMC, respectively, leading to the formationof the same oxidized product.

PDF

___

1. Newman, D. J.; Cragg, G. M.; Snader, K. M. Nat. Prod. Rep. 2000, 17, 215-234.
2. Kalaycıoğlu, Z.; Gazioğlu, I.; Erim, F. B. Nat. Prod. Res. 2017, 31, 2914-2917.
3. Kalaycıoğlu, Z.; Torlak, E.; Akın-Evingür, G.; Özen, I.; Erim, F. B. Int. J. Biol. Macromol. 2017, 101, 882-888.
4. Wright, L. E.; Frye, J. B.; Gorti, B.; Timmermann, B. N.; Funk, J. L. Curr. Pharm. Design 2013, 34, 6218-6225.
5. Liang, G. S.; Zhou, Y.; Shao, H. L.; Huang, K.; Xiao, J.; Huang, Z.; Li, X. Eur. J. Med. Chem. 2009, 44, 915-919.
6. Kulyal, P.; Kuchibhatla, L. N.; Maheshwari, K. U.; Babu, K. N.; Tetali, S. D.; Raghavendra, A. S. Curr. Sci. 2016, 111, 1816-1824.
7. Peram, M. R.; Jalalpure, S. S.; Joshi, S. A.; Palkar, M. B.; Diwan, P. W. J. Liq. Chromatogr. R. T. 2017, 40, 487-498.
8. Anubala, S.; Sekar, R.; Nagaiah, K. Food Anal. Method. 2016, 9, 2567-2578.
9. Tripathi, S.; Patel, K. G.; Bafna, A. M. J. Food Sci. Tech. Mys. 2010, 47, 678-681.
10. Kalaycıoğlu, Z.; Hashemi, P.; Günaydın, K.; Erim, F. B. Electrophoresis 2015, 36, 2516-2521
11. Manaia, M. A. N.; Diculescu, V. C.; Souza Gil, E.; Oliveira-Brett, A. M. J. Electroanal. Chem. 2012, 682, 83-89.
12. Masek, A.; Chrzescijanska, E.; Zaborski, M. Electrochim. Acta 2013, 107, 441-447.
13. Li, K.; Li, Y.; Yang, L.; Wang, L.; Ye, B. Anal. Methods 2014, 6, 7801-7808.
14. Modi, G.; Pitre, K. Def. Sci. J. 2010, 60, 255-258.
15. Jha, N. S.; Mishra, S.; Jha, S. K.; Surolia, A. Electrochim. Acta 2015, 151, 574-583.
16. Ziyatdinova, G. K.; Nizamova, A. M.; Budnikov, H. C. J. Anal. Chem. 2012, 67, 591-594.
17. Zhang, D.; Ouyang, X.; Ma, J.; Li, L.; Zhang, Y. Electroanalysis 2016, 28, 749-756.
18. Dinesh, B.; Devi, K. S. S.; Kumar, A. S. J. Electroanal. Chem. 2017, 804, 116-127.
19. Arrue, L.; Barra, T.; Camarada, M. B.; Zarate, X.; Schott, E. Chem. Phys. Lett. 2017, 677, 35-40.
20. Lungu, A.; Sandu, I.; Boscornea, C.; Tomas, S.; Mihailciuc, C. Rev. Roum. Chim. 2010, 55, 109-115.
21. Bonab, M. I.; Sardroodi, J. J.; Ebrahimzadeh, A. R.; Mehrnejad, F. J. Iran Chem. Soc. 2017, 14, 357-364.
22. Çakır, S.; Biçer, E.; Arslan, E. Y. Croat. Chem. Acta 2015, 88, 105-112.
23. Zheng, L.; Song, J. Sens. Actuat. B-Chem. 2009, 135, 650-655.
24. Kiani, A.; Raoof, J. B.; Nematollahi, D.; Ojani, R. Electroanalysis 2005, 17, 1755-1760.
25. Zhang, D.; Peng, Y.; Qi, H.; Gao, Q.; Zhang, C. Sens. Actuat. B-Chem. 2009, 136, 113-121.
26. Nicholson, R. S.; Shain, I. Anal. Chem. 1964, 36, 706-723.
27. Bard, A. J.; Faulkner, L. R. Electrochemical Methods: Fundamentals and Applications, 2nd Ed.; Wiley: New York, NY, USA, 2001.
28. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A. et al. Gaussian 09, Revision D.01; Gaussian, Inc.: Wallingford, CT, USA, 2010.
29. Perdew, J.; Burke, K.; Ernzerhof, M. Phys. Rev. Lett. 1996, 77, 3865-3868.
30. Perdew, J.; Burke, K.; Ernzerhof, M. Phys. Rev. Lett. 1997, 78, 1396.
31. Adamo, C.; Barone, V. J. Chem. Phys. 1998, 108, 664-675.
32. Barone, V.; Cossi, M.; Tomasi, J. J. Chem. Phys. 1997, 107, 3210-3221.
33. Barone, V.; Cossi, M. J. Phys. Chem. A 1998, 102, 1995-2001.
34. Cossi, M.; Rega, N.; Scalmani, G.; Barone, V. J. Comp. Chem. 2003, 24, 669-681.
35. Ziyatdinova, G.; Ziganshina, E.; Budnikov, H. Anal. Methods 2013, 5, 4750-4756.