Electrochemical oxidation of curcuminoids: an experimental and computational investigation

Authors

ZEYNEP KALAYCIOĞLU
NURGÜL KARADAŞ
MEHMET EMİN ÇINAR
SİBEL AYŞIL ÖZKAN
DURİŞEHVAR ÖZER ÜNAL
AYŞEGÜL GÖLCÜ
FATMA BEDİA ERİM

DOI

10.3906/kim-1812-43

Abstract

Curcuminoids, reported to have important biological properties, such as antioxidant, anti-Alzheimer, and antidiabetic 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 formation of the same oxidized product.

Keywords

Cyclic voltammetry, curcuminoids, density functional theory, differential pulse voltammetry

First Page

834

Last Page

845

Recommended Citation

KALAYCIOĞLU, ZEYNEP; KARADAŞ, NURGÜL; ÇINAR, MEHMET EMİN; ÖZKAN, SİBEL AYŞIL; ÜNAL, DURİŞEHVAR ÖZER; GÖLCÜ, AYŞEGÜL; and ERİM, FATMA BEDİA (2019) "Electrochemical oxidation of curcuminoids: an experimental and computational investigation," Turkish Journal of Chemistry: Vol. 43: No. 3, Article 9. https://doi.org/10.3906/kim-1812-43
Available at: https://journals.tubitak.gov.tr/chem/vol43/iss3/9