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Schlagwörter:
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Zusammenfassung:
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-
DC9), 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 speciesspecific,
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.
