Journal
FOOD CHEMISTRY
Volume 246, Issue -, Pages 481-489Publisher
ELSEVIER SCI LTD
DOI: 10.1016/j.foodchem.2017.11.100
Keywords
Cinnamic acids isomers; Radical scavenging; Guaiacyl, catechol and carboxyl moiety; Dienone lactone; Double HAT; Double SPLET
Funding
- Foundation of the Croatian Academy of Science and Arts [10-102/244-1-2016]
- Ministry of Science of the Republic of Serbia [172015, 174028]
- Slovak Grant Agency [VEGA 1/0594/16, 1/0416/17]
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The role of antiradical moieties (catechol, guaiacyl and carboxyl group) and molecular conformation in anti-oxidative 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 mu M concentrations, have a potential to contribute to health benefits by direct free radical scavenging.
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