3-Hydroxyanthranilic acid-derived compounds formed through electrochemical oxidation.
3-Hydroxyanthranilic acid (3-HAA)-derived oxidation products were analyzed using high-performance liquid chromatography with an electrochemical reactor and diode array detection and high-performance liquid chromatography with an electrochemical reactor and UV detection coupled with mass spectrometry. In addition to 3-HAA dimers such as cinnabarinic acid (CA), 6-amino-3-[(2-carboxy-6-hydroxyphenyl)amino]-2,5-dioxo-1,3-cyclohexadien e-1-carboxylic acid and 4,7-diamino-8-hydroxy-6H-dibenzo[a,d]pyran-6-one-3-carboxylic acid, a 3-HAA trimer and a 3-HAA tetramer were also detected and identified based on their electrospray ionization mass spectra and their UV-visible spectra. These five oxidation products were also detected on the elution profiles of high-performance liquid chromatography-diode array detection analyses for the reaction mixtures of the auto-oxidation of 3-HAA, of 3-HAA with potassium ferricyanide, of 3-HAA with horseradish peroxidase and hydrogen peroxide, and of 3-HAA with superoxide dismutase (SOD). 4,7-Diamino-8-hydroxy-6H-dibenzo[a,d]pyran-6-one-3-carboxylic acid was predominant in the auto-oxidation, in the reaction of 3-HAA with horseradish peroxidase and hydrogen peroxide, and in the electrochemical oxidation of 3-HAA at an applied potential of 0.0 V. On the other hand, CA, the 3-HAA trimer and the 3-HAA tetramer were predominant in the reaction of 3-HAA with K3[Fe(CN)6] and in the electrochemical oxidation of 3-HAA at an applied potential of 1.0 V.
Iwahashi
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Department of Chemistry, Wakayama Medical College, Japan.
D015095:3-Hydroxyanthranilic Acid / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D019281:Dimerization; D004563:Electrochemistry; D005292:Ferricyanides / Q000737:chemistry; D006735:Horseradish Peroxidase / Q000378:metabolism; D006861:Hydrogen Peroxide / Q000737:chemistry; D007700:Kinetics; D013058:Mass Spectrometry; D010078:Oxazines / Q000737:chemistry; D010084:Oxidation-Reduction; D013056:Spectrophotometry, Ultraviolet; D013482:Superoxide Dismutase / Q000378:metabolism
D005292:Ferricyanides; D010078:Oxazines; D015095:3-Hydroxyanthranilic Acid; C000483:cinnabarinic acid; D006861:Hydrogen Peroxide; D006735:Horseradish Peroxidase; D013482:Superoxide Dismutase; C028033:potassium ferricyanide