Ascaroside Profiling of Caenorhabditis elegans Using Gas Chromatography–Electron Ionization Mass Spectrometry,Analytical Chemistry

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Ascaroside Profiling of Caenorhabditis elegans Using Gas Chromatography–Electron Ionization Mass Spectrometry
Analytical Chemistry ( IF 6.7 ) Pub Date : 2017-09-21 00:00:00 , DOI: 10.1021/acs.analchem.7b02803
Stephan H. von Reuss ₁ , Franziska Dolke ₁ , Chuanfu Dong ₁

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Nematodes such as the model organism Caenorhabditis elegans produce various homologous series of l-ascarylose-derived glycolipids called ascarosides, which include several highly potent signals in intra and interspecies communication as well as cross-kingdom interactions. Given their low concentrations and large number of structurally similar components, mass spectrometric screens based on high-performance liquid chromatography–electrospray ionization–tandem mass spectrometry (HPLC-ESI-MS/MS) are commonly employed for ascaroside detection and quantification. Here, we describe a complementary gas chromatography–electron ionization mass spectrometry (GC-EIMS) screen that utilizes an ascarylose-derived K1-fragment ion signal at m/z 130.1 [C₆H₁₄OSi]^+● to highlight known as well as yet unidentified ascaroside components in TMS-derivatized crude nematode exometabolome extracts. GC-EIMS-based ascaroside profiling of wild-type and mutant C. elegans facilitates the analysis of all basic ascarosides using the same ionization technique while providing excellent resolution for the complete homologous series with side chains ranging from 3 to 33 carbons. Combined screening for m/z 130.1 along with side chain-specific J1 [M − 173]⁺ and J2 [M − 291]⁺ fragment ions, as well as additional characteristic marker ions from α-cleavage, enables convenient structure assignment of ca. 200 components from wild-type and peroxisomal β-oxidation mutants including (ω − 1)-linked acyl, enoyl, β-hydroxyacyl, and 2-ketoalkyl ascarosides along with their (ω)-linked or α-methyl isomers and ethanolamide derivatives, as well as 2-hydroxyalkyl ascarosides. Given the widespread availability of GC-MS and its increasing popularity in metabolomics, this method will promote the identification of ascarosides in C. elegans and other nematodes.

中文翻译：

秀丽隐杆线虫的Ascaroside分析应用气相色谱-电子电离质谱

线虫，例如模型生物秀丽隐杆线虫（Caenorhabditis elegans），会产生各种同源系列的l -a糖衍生的糖脂，称为a虫苷，在种内和种间通讯以及跨国界的相互作用中包括多个高效信号。由于它们的低浓度和大量结构相似的成分，基于高效液相色谱-电喷雾电离-串联质谱（HPLC-ESI-MS / MS）的质谱筛通常用于commonly虫苷的检测和定量。在这里，我们描述了一种互补的气相色谱-电子电离质谱（GC-EIMS）屏幕，该屏幕利用了m / z上从天基糖衍生的K1碎片离子信号130.1 [C ₆ H ₁₄ OSi] ^+●突出了TMS衍生的粗线虫exometabolome提取物中已知的和尚未鉴定的a甙成分。基于GC-EIMS的野生型和突变型秀丽隐杆线虫的a螨苷谱分析，可使用相同的电离技术促进所有基本basic螨的分析，同时为侧链范围从3至33个碳原子的完整同源序列提供出色的分离度。对m / z 130.1以及侧链特异性J1 [M-173] ⁺和J2 [M-291] ^+的联合筛选碎片离子以及来自α裂解的其他特征性标记离子，使ca的结构方便分配。来自野生型和过氧化物酶体β-氧化突变体的200个成分，包括（ω-1）-连接的酰基，烯酰基，β-羟基酰基和2-酮烷基a糖苷以及它们的（ω）-连接的或α-甲基异构体和乙醇酰胺衍生物，以及2-羟烷基杀螨剂。鉴于GC-MS的广泛应用及其在代谢组学中的日益普及，该方法将促进秀丽隐杆线虫和其他线虫中的scar虫苷的鉴定。

更新日期：2017-09-21

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