Interaction and reactivity of urocanic acid towards peroxyl radicals

• Published in: Redox report : communications in free radical research Vol. 10; no. 4; pp. 227 - 234
• Main Authors: López-Alarcón, C., Aspée, A., Henríquez, C., Campos, A. M., Lissi, E. A.
• Format: Journal Article
• Language: English
• Published: England Taylor & Francis 01.08.2005
• Subjects: Amidines - chemistry; Arylsulfonates - pharmacology; Bacterial Proteins - metabolism; C-PHYCOCYANIN; Chromans - pharmacology; Copper - chemistry; Free Radicals; LDL; Lipoproteins, LDL - chemistry; Models, Chemical; Oxidative Stress; Oxygen - metabolism; Peroxides - chemistry; PEROXYL RADICALS; Phycocyanin - chemistry; Reactive Oxygen Species; Spirulina; UROCANIC ACID; Urocanic Acid - metabolism; Urocanic Acid - pharmacology
• ISSN: 1351-0002; 1743-2928
• DOI: 10.1179/135100005X70189

The capacity of urocanic acid to interact with peroxyl radicals has been evaluated in several systems: oxidation in the presence of a free radical source (2,2′-azobis(2-amidinopropane; AAPH), protection of phycocyanin bleaching elicited by peroxyl radicals, and Cu(II)- and AAPH-promoted LDL oxidation. The results indicate that both isomers (cis and trans) are mild peroxyl radical scavengers. For example, trans-urocanic acid is nearly 400 times less efficient than Trolox in the protection of the peroxyl radical promoted bleaching of phycocyanin. Regarding the removal of urocanic acid by peroxyl radicals, nearly 100 μM trans-urocanic acid is required to trap half of the produced radicals under the employed conditions (10 mM AAPH, 37°C). Competitive experiments show that the cis-isomer traps peroxyl radicals ~30% less efficiently than the trans-isomer. Given the high concentrations that trans-urocanic acid reaches in skin, its capacity to trap peroxyl radicals could contribute to the protection of the tissue towards ROS-mediated processes. Furthermore, both isomers, and particularly the cis-isomer, protect LDL from Cu(II)-induced oxidation.