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Quantitative analysis of oxidized vitamin B1 metabolites generated by hypochlorous acid.
Free Radical Biology and Medicine ( IF 7.1 ) Pub Date : 2020-03-19 , DOI: 10.1016/j.freeradbiomed.2020.03.010 Hitoshi Sasatsuki 1 , Atsuo Nakazaki 1 , Koji Uchida 2 , Takahiro Shibata 3
Free Radical Biology and Medicine ( IF 7.1 ) Pub Date : 2020-03-19 , DOI: 10.1016/j.freeradbiomed.2020.03.010 Hitoshi Sasatsuki 1 , Atsuo Nakazaki 1 , Koji Uchida 2 , Takahiro Shibata 3
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Thiamine, a water-soluble essential vitamin known as vitamin B1, acts as an important cofactor in various cellular processes, such as metabolism and energy production. Thiamine is also thought to have antioxidant effects as a singlet oxygen scavenger and a lipid peroxidation inhibitor. However, the oxidation mechanism and oxidized metabolites of thiamine are not completely established. In the present study, we investigated the oxidative reactivity of thiamine and found that three products were formed upon the reaction of thiamine with hypochlorous acid (HOCl). Based on the NMR and high resolution mass spectrometric analysis, the HOCl-oxidized metabolites of thiamine were identified as formylaminopyrimidine (FAP), thiamine sulfonic acid (TSA), and thiamine sulfinic ester (TSE). To evaluate the formation of these oxidized metabolites in vivo, we established a specific method for quantification of the oxidized thiamine metabolites using liquid chromatography-tandem mass spectrometry coupled with a stable isotope dilution method. Using this method, it was shown that the oxidized thiamine metabolites were generated in the culture media of phorbol-12-myristate-acetate-treated neutrophil-like cells in a myeloperoxidase-dependent manner. Moreover, significantly higher amounts of FAP and TSE were detected in the lung tissues of the lipopolysaccharide-treated mice compared to the controls. These findings provide not only insights into the oxidative metabolism of thiamine, but also the possibility that the oxidized thiamine metabolites may be potential biomarkers for HOCl-related oxidative stress.
中文翻译：
次氯酸生成的氧化的维生素B1代谢产物的定量分析。
硫胺素（一种称为维生素B1的水溶性必需维生素）在各种细胞过程（例如新陈代谢和能量产生）中起着重要的辅助因子的作用。硫胺素还被认为具有抗氧化作用，作为单线态氧清除剂和脂质过氧化抑制剂。然而，硫胺素的氧化机理和氧化代谢物尚未完全建立。在本研究中，我们研究了硫胺素的氧化反应性，发现硫胺素与次氯酸（HOCl）反应形成了三种产物。基于NMR和高分辨率质谱分析，硫胺的HOCl氧化代谢产物被鉴定为甲酰氨基嘧啶（FAP），硫胺磺酸（TSA）和硫胺亚磺酸酯（TSE）。为了评估体内这些氧化代谢产物的形成，我们建立了使用液相色谱-串联质谱和稳定同位素稀释法定量氧化硫胺素代谢物的特定方法。使用该方法表明，氧化的硫胺素代谢产物以髓过氧化物酶依赖性方式在佛波醇-12-肉豆蔻酸酯-乙酸酯处理的嗜中性粒细胞样细胞的培养基中产生。此外，与对照相比，在脂多糖治疗的小鼠的肺组织中检测到明显更高的FAP和TSE量。这些发现不仅提供了对硫胺素氧化代谢的见解，而且还提供了氧化的硫胺素代谢物可能是HOCl相关的氧化应激的潜在生物标志物的可能性。
更新日期：2020-03-19
中文翻译：
次氯酸生成的氧化的维生素B1代谢产物的定量分析。
硫胺素（一种称为维生素B1的水溶性必需维生素）在各种细胞过程（例如新陈代谢和能量产生）中起着重要的辅助因子的作用。硫胺素还被认为具有抗氧化作用，作为单线态氧清除剂和脂质过氧化抑制剂。然而，硫胺素的氧化机理和氧化代谢物尚未完全建立。在本研究中，我们研究了硫胺素的氧化反应性，发现硫胺素与次氯酸（HOCl）反应形成了三种产物。基于NMR和高分辨率质谱分析，硫胺的HOCl氧化代谢产物被鉴定为甲酰氨基嘧啶（FAP），硫胺磺酸（TSA）和硫胺亚磺酸酯（TSE）。为了评估体内这些氧化代谢产物的形成，我们建立了使用液相色谱-串联质谱和稳定同位素稀释法定量氧化硫胺素代谢物的特定方法。使用该方法表明，氧化的硫胺素代谢产物以髓过氧化物酶依赖性方式在佛波醇-12-肉豆蔻酸酯-乙酸酯处理的嗜中性粒细胞样细胞的培养基中产生。此外，与对照相比，在脂多糖治疗的小鼠的肺组织中检测到明显更高的FAP和TSE量。这些发现不仅提供了对硫胺素氧化代谢的见解，而且还提供了氧化的硫胺素代谢物可能是HOCl相关的氧化应激的潜在生物标志物的可能性。
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