Comparison of Physicochemical, Antioxidant, and Cytotoxic Properties of Caffeic Acid Conjugates.

Spectroscopic studies (FT-IR, Raman, 1 H, and 13 C NMR, UV-VIS) of caffeic acid (CFA) and its conjugates, i.e., caftaric acid (CTA), cichoric acid (CA), and cynarin (CY), were carried out. The antioxidant activity of these compounds was determined by a superoxide dismutase (SOD) activity assay and the hydroxyl radical (HO • ) inhibition assay. The cytotoxicity of these compounds was performed on DLD-1 cell lines. The molecules were theoretically modeled using the B3LYP-6-311++G(d,p) method. Aromaticity indexes (HOMA, I6, BAC, Aj), HOMO and LUMO orbital energies and reactivity descriptors, NBO electron charge distribution, EPS electrostatic potential maps, and theoretical IR and NMR spectra were calculated for the optimized model systems. The structural features of these compounds were discussed in terms of their biological activities.