Iwahashi H
Department of Chemistry, Wakayama Medical College, Japan.
J Chromatogr B Biomed Sci Appl. 1999 Dec 24;736(1-2):237-45. doi: 10.1016/s0378-4347(99)00463-6.
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.
使用配备电化学反应器和二极管阵列检测的高效液相色谱法以及配备电化学反应器和紫外检测并结合质谱的高效液相色谱法，对3-羟基邻氨基苯甲酸（3-HAA）衍生的氧化产物进行了分析。除了3-HAA二聚体，如朱红酸（CA）、6-氨基-3-[(2-羧基-6-羟基苯基)氨基]-2,5-二氧代-1,3-环己二烯-1-羧酸和4,7-二氨基-8-羟基-6H-二苯并[a,d]吡喃-6-酮-3-羧酸外，还根据其电喷雾电离质谱和紫外可见光谱检测并鉴定出一种3-HAA三聚体和一种3-HAA四聚体。在3-HAA自氧化、3-HAA与铁氰化钾、3-HAA与辣根过氧化物酶和过氧化氢以及3-HAA与超氧化物歧化酶（SOD）反应混合物的高效液相色谱-二极管阵列检测分析的洗脱图谱上，也检测到了这五种氧化产物。在自氧化、3-HAA与辣根过氧化物酶和过氧化氢的反应以及3-HAA在0.0 V施加电位下的电化学氧化中，4,7-二氨基-8-羟基-6H-二苯并[a,d]吡喃-6-酮-3-羧酸占主导。另一方面，在3-HAA与K3[Fe(CN)6]的反应以及3-HAA在1.0 V施加电位下的电化学氧化中，CA、3-HAA三聚体和3-HAA四聚体占主导。
