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Ascaroside profiling of Caenorhabditis elegans using gas chromatography-electron ionization mass spectrometry

MPG-Autoren
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von Reuss,  Stephan H.
Department of Bioorganic Chemistry, Prof. Dr. W. Boland, MPI for Chemical Ecology, Max Planck Society;

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Dolke,  Franziska
Department of Bioorganic Chemistry, Prof. Dr. W. Boland, MPI for Chemical Ecology, Max Planck Society;

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Dong,  Chuan-Fu
Department of Bioorganic Chemistry, Prof. Dr. W. Boland, MPI for Chemical Ecology, Max Planck Society;

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Zitation

von Reuss, S. H., Dolke, F., & Dong, C.-F. (2017). Ascaroside profiling of Caenorhabditis elegans using gas chromatography-electron ionization mass spectrometry. Analytical Chemistry, 89(19), 10570-10577. doi:10.1021/acs.analchem.7b02803.


Zitierlink: https://hdl.handle.net/11858/00-001M-0000-002D-D9DD-3
Zusammenfassung
Nematodes such as the model organism Caenorhabditis elegans produce homologous series of L-ascarylose-derived glyco-lipids 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 HPLC-ESI-MS/MS are commonly employed for ascaroside detection and quantification. Here, we describe a complementary 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 exo-metabolome 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 sidechains ranging from 3 to 33 carbons. Combined screening for m/z 130.1 along with sidechain-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.