Systematic Derivatization of Curcumin and its Effect on Antioxidant Capacity and Action Mechanism. Cyclic Voltammetry and DFT as Tools of Analysis
| Autor: | Patricia Guadarrama, Estrella Ramos, J.C. Aguilar, Fernando Belmont-Bernal |
|---|---|
| Rok vydání: | 2016 |
| Předmět: |
Chemistry
Superoxide 010401 analytical chemistry Aromaticity 04 agricultural and veterinary sciences General Chemistry Photochemistry 040401 food science 01 natural sciences Medicinal chemistry 0104 chemical sciences chemistry.chemical_compound 0404 agricultural biotechnology Mass spectrum Phenol Molecular orbital Cyclic voltammetry Derivatization Voltammetry |
| Zdroj: | ChemistrySelect. 1:5091-5098 |
| ISSN: | 2365-6549 |
| DOI: | 10.1002/slct.201600992 |
| Popis: | Eight curcumin derivatives were synthesized by esterification of its phenol groups with first and second generation polyester dendrons (dendronization) or glutaric anhydride (glutarization), in a systematic scheme where mono and disubstitutions were carried out. The dendronization of curcumin (CUR) affects the fragmentation patterns in mass spectra, particularly for the disubstituted OH-terminated second generation derivative (labeled as 2C2), undergoing the cleavage of one of the aromatic rings. This fact may be related to the antioxidant capacity of 2C2, evaluated following its reaction with superoxide (O2•-) by cyclic voltammetry (CV). As opposed to CUR and the rest of its derivatives that react with O2•- via proton transfer reactions, 2C2 reacts with O2•- mainly by hydrogen atom transfer. 2C2 radical scavenging activity versus O2•- is higher than the one observed for CUR. From DFT calculations, independently of the substitution on CUR, the frontier molecular orbitals remain nearly unaltered as compared to CUR. On the other hand, when CUR is dendronized, the electric dipole moment notably changes as a function of the nature of the terminal groups. |
| Databáze: | OpenAIRE |
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