Penta-deuterium-labeled 4E, 8Z-sphingadienine for rapid analysis in sphingolipidomics study

IF 3.4 3区生物学 Q2 BIOCHEMISTRY & MOLECULAR BIOLOGY

Chemistry and Physics of Lipids Pub Date : 2022-07-01 DOI:10.1016/j.chemphyslip.2022.105202

Yuta Murai , Kohei Yuyama , Daisuke Mikami , Yasuyuki Igarashi , Kenji Monde

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引用次数: 1

Abstract

The use of deuterium-incorporated bioactive compounds is an efficient method for tracing their metabolic fate and for quantitative analysis by mass spectrometry without complicated HPLC separation even if their amounts are extremely small. Plant sphingolipids and their metabolites, which have C4, 8-olefins on a common backbone as a sphingoid base, show unique and fascinating bioactivities compared to those of sphingolipids in mammals. However, the functional and metabolic mechanisms of exogenous plant sphingolipids have not been elucidated due to the difficulty in distinguishing exogenous sphingolipids from endogenous sphingolipids having the same polarity and same molecular weight by mass spectrometric analysis. Their roles might be elucidated by the use of deuterated probes with original biological and physicochemical properties. In this study, we designed (2S,3R,4E,8Z)-2-aminooctadeca-4,8-diene-17,17,18,18,18-d₅-1,3-diol (penta-deuterium-labeled 4E, 8Z-sphingadienine) as a tracer for exogenous metabolic studies. In addition, the sphingadienine was confirmed to be metabolized in HEK293 cells and showed distinct peaks in mass spectrometric analysis.

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五氘标记4E, 8z -鞘脂二嘌呤在鞘脂组学研究中的快速分析

使用氘结合的生物活性化合物是追踪其代谢命运和质谱定量分析的有效方法，无需复杂的HPLC分离，即使它们的量非常小。植物鞘脂及其代谢产物以C4, 8-烯烃为鞘碱，与哺乳动物鞘脂相比，具有独特而迷人的生物活性。然而，由于质谱分析难以区分具有相同极性和相同分子量的外源鞘脂和内源鞘脂，因此外源鞘脂的功能和代谢机制尚未阐明。它们的作用可以通过使用具有原始生物和物理化学性质的氘化探针来阐明。在本研究中，我们设计了(2S,3R,4E,8Z)-2-氨基十八烷-4,8-二烯-17,17,18,18,18-d5-1,3-二醇(五氘标记的4E,8Z -鞘脂二烯)作为外源性代谢研究的示踪剂。此外，鞘脂嘌呤在HEK293细胞中被代谢，并在质谱分析中显示出明显的峰。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Chemistry and Physics of Lipids 生物-生化与分子生物学

CiteScore

7.60

自引率

2.90%

发文量

审稿时长

40 days

期刊介绍： Chemistry and Physics of Lipids publishes research papers and review articles on chemical and physical aspects of lipids with primary emphasis on the relationship of these properties to biological functions and to biomedical applications. Accordingly, the journal covers: advances in synthetic and analytical lipid methodology; mass-spectrometry of lipids; chemical and physical characterisation of isolated structures; thermodynamics, phase behaviour, topology and dynamics of lipid assemblies; physicochemical studies into lipid-lipid and lipid-protein interactions in lipoproteins and in natural and model membranes; movement of lipids within, across and between membranes; intracellular lipid transfer; structure-function relationships and the nature of lipid-derived second messengers; chemical, physical and functional alterations of lipids induced by free radicals; enzymatic and non-enzymatic mechanisms of lipid peroxidation in cells, tissues, biofluids; oxidative lipidomics; and the role of lipids in the regulation of membrane-dependent biological processes.