Stereoselective Reaction Enabling Simultaneous Analysis of Carbon–Carbon Double-Bond Configuration and the Position of Monounsaturated Fatty Acids through UHPLC-ESI-MRM-MS

IF 6.7 1区化学 Q1 CHEMISTRY, ANALYTICAL

Analytical Chemistry Pub Date : 2025-01-29 DOI:10.1021/acs.analchem.4c06262

Chunlin Yue, Lingyu Zhao, Zhenchao Long, Xuwei Song, Jinqi Yang, Yuan Cao, Yuanyuan Zhang, Yangyang Zhang, Zhenwen Zhao

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Abstract

Monounsaturated fatty acids (MUFA) are an important class of nutrients and are involved in lipid metabolism. The positions of the C=C bond and cis–trans isomerism have a significant influence on their physiological activity. However, simultaneously detecting these two structural properties has been challenging due to multiple isomers of MUFA. In this study, we developed a method that involved an N-aminophthalimide (PhthNH₂) derivatization of the C=C bond in MUFA, followed by analysis using ultrahigh-performance liquid chromatography-electrospray ionization-multiple reaction monitoring mass spectrometry (UHPLC-ESI-MRM-MS) technology to achieve analysis of cis–trans isomers and positional isomers of the C=C bond. The derivatives of cis–trans isomers of the C=C bond were well separated in UHPLC, and their corresponding C=C bond positions were deduced from characteristic fragment ions in tandem mass spectrometry. With our method, we found MUFA with different double-bond positions and cis–trans isomers in several samples, including mouse kidney, butter, etc., achieving qualitative analysis and relative quantitation. This method is expected to be applied by more researchers in lipidomics studies in the future.

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用UHPLC-ESI-MRM-MS同时分析碳-碳双键构型和单不饱和脂肪酸位置的立体选择反应

单不饱和脂肪酸（MUFA）是一类重要的营养物质，参与脂质代谢。C=C键的位置和顺反异构对其生理活性有显著影响。然而，由于MUFA有多种异构体，同时检测这两种结构性质一直具有挑战性。本研究采用n-氨基苯并酰亚胺（PhthNH2）衍生化MUFA中的C=C键，然后采用超高效液相色谱-电喷雾电离-多重反应监测质谱（UHPLC-ESI-MRM-MS）技术分析C=C键的顺反异构体和位置异构体。在UHPLC中，C=C键的顺反异构体衍生物得到了很好的分离，并在串联质谱中通过特征片段离子推导出了相应的C=C键位置。通过我们的方法，我们在包括小鼠肾脏、黄油等样品中发现了具有不同双键位置和顺反式异构体的MUFA，并进行了定性分析和相对定量。该方法有望在未来的脂质组学研究中得到更多的应用。

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来源期刊

Analytical Chemistry 化学-分析化学

CiteScore

12.10

自引率

12.20%

发文量

1949

审稿时长

1.4 months

期刊介绍： Analytical Chemistry, a peer-reviewed research journal, focuses on disseminating new and original knowledge across all branches of analytical chemistry. Fundamental articles may explore general principles of chemical measurement science and need not directly address existing or potential analytical methodology. They can be entirely theoretical or report experimental results. Contributions may cover various phases of analytical operations, including sampling, bioanalysis, electrochemistry, mass spectrometry, microscale and nanoscale systems, environmental analysis, separations, spectroscopy, chemical reactions and selectivity, instrumentation, imaging, surface analysis, and data processing. Papers discussing known analytical methods should present a significant, original application of the method, a notable improvement, or results on an important analyte.