期刊
COMPUTATIONAL AND THEORETICAL CHEMISTRY
卷 1012, 期 -, 页码 33-40出版社
ELSEVIER
DOI: 10.1016/j.comptc.2013.02.018
关键词
cis-Ferulic acid; trans-Ferulic acid; Antioxidant properties; DFT; C-PCM model
资金
- Poznan Supercomputing and Networking Center (PCSS)
- Theoretical investigations of antioxidant activity of cinnamic acid's derivatives [85]
- Theoretical investigations of antioxidant activity of ferulic acid's derivatives [130]
In this paper, we present a summary of structure - antioxidant activity relation of ferulic acid's stereoisomers. We have analyzed four antioxidant mechanisms important in free radicals scavenging: hydrogen atom transfer (HAT), sequential proton loss electron transfer (SPLET), single electron transfer - proton transfer (SET-PT) and transition metal chelation (TMC) by calculation of antioxidant descriptors and other related parameters. All calculations have been performed with B3LYP/6-311++G(2d,2p) level of theory in vacuum and in ethanol, water and dimethyl sulfoxide media, based on conductor-like polarizable continuum solvation model. The results have shown that cis-ferulic acid and trans-ferulic acid (including less energetic rotamers) display similar reactivity and, in comparison to previously published results for phenols and polyphenols, may be considered as a good antioxidants. It has been determined that planar structure of ferulic acid (FA) supported by pi-electron delocalization positively influences the ability of this compound to neutralize free radicals. Moreover, we have shown that for FA HAT is the most preferable in gas-phase and SPLET is more preferable in all polar media studied. FA might be also considered as a potential transition metals chelating agent. (c) 2013 Elsevier B.V. All rights reserved.
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