Boron Isotope Tag-Assisted Ultrahigh-Performance Liquid Chromatography Coupled with High-Resolution Mass Spectrometry for Discovery and Annotation of cis-Diol-Containing Metabolites,Analytical Chemistry

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Boron Isotope Tag-Assisted Ultrahigh-Performance Liquid Chromatography Coupled with High-Resolution Mass Spectrometry for Discovery and Annotation of cis-Diol-Containing Metabolites
Analytical Chemistry ( IF 6.7 ) Pub Date : 2021-01-26 , DOI: 10.1021/acs.analchem.0c05037
Cai-Feng Xiong ₁ , Jun Ding ₁ , Quan-Fei Zhu ₁ , Ya-Li Bai ₁ , Xiao-Ming Yin ₁ , Tian-Tian Ye ₁ , Qiong-Wei Yu ₁ , Yu-Qi Feng _{1,

2}

Affiliation

cis-Diol-containing metabolites are widely distributed in living organisms, and they participate in the regulation of various important biological activities. The profiling of cis-diol-containing metabolites could help us in fully understanding their functions. In this work, based on the characteristic isotope pattern of boron, we employed a boronic acid reagent as the isotope tag to establish a sensitive and selective liquid chromatography–high-resolution mass spectrometry method for the screening and annotation of cis-diol-containing metabolites in biological samples. Boronic acid reagent 2-methyl-4-phenylaminomethylphenylboronic acid was used to label the cis-diol-containing metabolites in biological samples to improve the selectivity and MS sensitivity of cis-diol-containing metabolites. Based on the characteristic 0.996 Da mass difference of precursor ions and the peak intensity ratio of 1:4 originating from ¹⁰B and ¹¹B natural isotopes, the potential cis-diol-containing metabolites were rapidly screened from biological samples. Potential cis-diol-containing metabolites were annotated by database searching and analysis of fragmentation patterns obtained by multistage MS (MSⁿ) via collision-induced dissociation. Importantly, the cis-diol position could be readily resolved by the MS³ spectrum. With this method, a total of 45 cis-diol-containing metabolites were discovered in rice, including monoglycerides, polyhydroxy fatty acids, fatty alcohols, and so forth. Furthermore, the established method showed superiority in avoiding false-positive results in profiling cis-diol-containing metabolites.

中文翻译：

硼同位素标记辅助超高效液相色谱与高分辨率质谱联用用于发现和注释含顺式-二醇的代谢物

含顺式二元醇的代谢物广泛分布于活生物体中，它们参与各种重要生物活动的调节。含顺式-二醇代谢物的概况分析可以帮助我们充分了解其功能。在这项工作中，基于硼的特征同位素模式，我们使用硼酸试剂作为同位素标记，建立了灵敏且选择性的液相色谱-高分辨率质谱法，用于筛选和注释含顺式-二醇的代谢物在生物样品中。硼酸试剂2-甲基-4-苯基氨基甲基苯基硼酸用于标记顺式生物样品中的含α-二醇的代谢物，以提高含顺式-二醇的代谢物的选择性和MS灵敏度。基于前体离子的特征性0.996 Da质量差异和源自¹⁰ B和¹¹ B自然同位素的1：4峰强度比，可以从生物样品中快速筛选出潜在的含顺式-二醇代谢物。通过数据库搜索和通过碰撞诱导解离通过多级质谱（MS ⁿ）获得的片段化模式分析，注释了潜在的含顺式二醇代谢物。重要的是，MS ³可以轻松解决顺式-二醇位置光谱。通过这种方法，在水稻中总共发现了45种含顺式二醇的代谢物，包括甘油单酸酯，多羟基脂肪酸，脂肪醇等。此外，已建立的方法在分析含顺式-二醇的代谢物方面显示出避免假阳性结果的优势。

更新日期：2021-02-09

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