ArticleThe Journal of organic chemistry2018
Comparative Ascaroside Profiling of Caenorhabditis Exometabolomes Reveals Species-Specific (ω) and (ω - 2)-Hydroxylation Downstream of Peroxisomal β-Oxidation.
Article in The Journal of organic chemistry, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 12 papers.
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Who cites it
12 citing papers in PubMed, 25 citations in OpenAlex.
- Biosynthesis of modular signaling molecules requires functional diversification of carboxylesterases in Pristionchus pacificus.Communications biology · 2025Article
- Nematode Pheromones as Key Mediators of Behavior, Development, and Ecological Interactions.Biomolecules · 2025Review
- The Lipid Composition of the Exo-Metabolome fromMetabolites · 2025Article
- An acyl-CoA thioesterase is essential for the biosynthesis of a key dauer pheromone in C. elegans.Cell chemical biology · 2024Article
- Transcriptomic profiling of sex-specific olfactory neurons reveals subset-specific receptor expression in Caenorhabditis elegans.Genetics · 2023Article
- Advances in Microbial NMR Metabolomics.Advances in experimental medicine and biology · 2023Article
- Article
- Photoaffinity probes for nematode pheromone receptor identification.Organic & biomolecular chemistry · 2019Article
- Ascaroside Pheromones: Chemical Biology and Pleiotropic Neuronal Functions.International journal of molecular sciences · 2019Review
- A primer on pheromone signaling in Caenorhabditis elegans for systems biologists.Current opinion in systems biology · 2019Article
- Article
- Ascaroside#18 Promotes Plant Defence by Repressing Auxin Signalling.Physiologia plantarumArticle
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Authors and funding
6 authors at 4 institutions in 3 countries.
Funding
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.
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