首页|Identification of the DPPH radical scavenging reaction adducts of ferulic acid and sinapic acid and their structure-antioxidant activity relationship
Identification of the DPPH radical scavenging reaction adducts of ferulic acid and sinapic acid and their structure-antioxidant activity relationship
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NSTL
Elsevier
Phenolic acids may provide health benefits as antioxidants and have potential applications in food and pharmaceutical science. The antioxidant activity and mechanism of sinapic acid (SA), ferulic acid (FA), disinapic acids (DSA) and diferulic acids (DFA) were evaluated by experiments and theoretical calculation. DSA-1-3 and DFA-1-3 were synthesized and identified by HPLC-MS and nuclear magnetic resonance. DSA-1 and DFA-1 (8-8'dilactone dimers) were identified as adducts in the SA-/FA-DPPH system for the first time, which confirmed the mechanism of radical adduct formation. The orders of their antioxidant activities by DPPH and FRAP assays were consistent with theoretical calculation based on density functional theory, e.g., DSA-3 > DSA-2 > SA > DSA-1, DFA-3 > DFA-2 > FA > DFA-1, and SA group > FA group. These phenolic acids were more likely to occur the HAT mechanism in the gas phase, while occur SETPT and SPLET mechanisms in polar solvents. Moreover, the active phenolic hydroxyls of DSA-2 (4-OH) and DFA-2 (4'-OH) were opposite according to the bond dissociation energy and HOMO distribution. Methoxyl on the benzene rings may play a crucial role in the formation of DSA and DFA, as well as the antioxidant activity and phenolic hydroxyl active center.
NSTL
Elsevier
