Comparative Ascaroside Profiling of Caenorhabditis Exometabolomes Reveals 
Species-Specific (ω) and (ω - 2)-Hydroxylation Downstream of Peroxisomal 
β-Oxidation

Dong, C; Reilly, DK; Bergame, C; Dolke, F; Srinivasan, J; von Reuss, SH

doi:10.1021/acs.joc.8b00094

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Comparative Ascaroside Profiling of Caenorhabditis Exometabolomes Reveals Species-Specific (ω) and (ω - 2)-Hydroxylation Downstream of Peroxisomal β-Oxidation

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Dong, C
Department Integrative Evolutionary Biology, Max Planck Institute for Developmental Biology, Max Planck Society;

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Citation

Dong, C., Reilly, D., Bergame, C., Dolke, F., Srinivasan, J., & von Reuss, S. (2018). Comparative Ascaroside Profiling of Caenorhabditis Exometabolomes Reveals Species-Specific (ω) and (ω - 2)-Hydroxylation Downstream of Peroxisomal β-Oxidation. The Journal of Organic Chemistry, 83(13), 7109-7120. doi:10.1021/acs.joc.8b00094.

Cite as: https://hdl.handle.net/21.11116/0000-000A-7672-1

Abstract

Chemical communication in nematodes such as the model organism Caenorhabditis elegans is modulated by a variety of glycosides based on the dideoxysugar l-ascarylose. Comparative ascaroside profiling of nematode exometabolome extracts using a GC-EIMS screen reveals that several basic components including ascr#1 (asc-C7), ascr#2 (asc-C6-MK), ascr#3 (asc-ΔC9), ascr#5 (asc-ωC3), and ascr#10 (asc-C9) are highly conserved among the Caenorhabditis. Three novel side chain hydroxylated ascaroside derivatives were exclusively detected in the distantly related C. nigoni and C. afra. Molecular structures of these species-specific putative signaling molecules were elucidated by NMR spectroscopy and confirmed by total synthesis and chemical correlations. Biological activities were evaluated using attraction assays. The identification of (ω)- and (ω - 2)-hydroxyacyl ascarosides demonstrates how GC-EIMS-based ascaroside profiling facilitates the detection of novel ascaroside components and exemplifies how species-specific hydroxylation of ascaroside aglycones downstream of peroxisomal β-oxidation increases the structural diversity of this highly conserved class of nematode signaling molecules.