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Title: | Theoretical study of the thermodynamics of the mechanisms underlying antiradical activity of cinnamic acid derivatives | Authors: | Amić, Ana Marković, Zoran Klein, Erik Dimitrić Marković, Jasmina Milenković, Dejan |
Keywords: | Caffeic acid (PubChem CID: 689043);Cinnamic acids isomers;Dienone lactone;Dihydrocaffeic acid (PubChem CID: 348154);Dihydroferulic acid (PubChem CID: 14340);Double HAT;Double SPLET;Ferullic acid (PubChem CID: 445858);Guaiacyl, catechol and carboxyl moiety;Radical scavenging | Issue Date: | 25-Apr-2018 | Journal: | Food chemistry | Abstract: | The role of antiradical moieties (catechol, guaiacyl and carboxyl group) and molecular conformation in antioxidative potency of dihydrocaffeic acid (DHCA) and dihydroferulic acid (DHFA) was investigated by density functional theory (DFT) method. The thermodynamic preference of different reaction paths of double (2H+/2e-) free radical scavenging mechanisms was estimated. Antiradical potency of DHCA and DHFA was compared with that exerted by their unsaturated analogs - caffeic acid (CA) and ferulic acid (FA). Cis/trans and anti-isomers of studied cinnamic acid derivatives may scavenge free radicals via double processes by involvement of catechol or guaiacyl moiety. Carboxyl group of syn-isomers may also participate in the inactivation of free radicals. Gibbs free energies of reactions with various free radicals indicate that syn-DHCA and syn-DHFA, colon catabolites that could be present in systemic circulation in low μM concentrations, have a potential to contribute to health benefits by direct free radical scavenging. |
URI: | https://dspace.ffh.bg.ac.rs/handle/123456789/963 | ISSN: | 0308-8146 | DOI: | 10.1016/j.foodchem.2017.11.100 |
Appears in Collections: | Journal Article |
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