Enhanced Antioxidant Activity of Ursolic Acid by Complexation with Copper (II): Experimental and Theoretical Study

摘要

The copper (II) complex of ursolic acid (Cu(II) UA) was synthesized and discussed in terms of its infrared, UV–visible spectra, quantum-chemical calculations at B3LYP/6-31G(d) level and antioxidant capacity. The copper (II) complex was stable in methanolic solution with the molar ratio metal:ligand 1:1. The data obtained by FT-IR confirmed the metal ion coordination through the carboxylate anion. The antioxidant properties of ursolic acid and its complex with Cu were discussed on the basis of energy of the highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) and values of chemical reactivity parameters. The antiradical properties of ursolic acid and the Cu (II) complex were examined against DPPH• and HO• radicals, and the ferric reducing antioxidant power (FRAP) was examined. The Cu(II) complex showed higher antioxidant activity than ursolic acid, i.e., in DPPH• assay, the EC50 for UA was 47.0 mM, whereas, for Cu(II), UA EC50 = 19.5 mM; the FRAP value for UA was 20.8 µMFe2+, and 35.4 µMFe2+ for Cu(II) UA (compound concentration 3 mM). Although there was no distinct difference in the antioxidant activity against HO• between these two chemicals, they were both better HO• scavengers than DPPH• and showed different kinetics in the reaction with DPPH•.