Dimerization of conserved ascaroside building blocks generates species-specific male attractants in Caenorhabditis nematodes.

Org Biomol Chem

Department of Bioorganic Chemistry, Max Planck Institute for Chemical Ecology, Hans-Knöll Straße 8, D-07745 Jena, Germany and Laboratory for Bioanalytical Chemistry, Institute of Chemistry, University of Neuchâtel, Avenue de Bellevaux 51, CH-2000 Neuchâtel, Switzerland.

Published: July 2020

AI Article Synopsis

  • Researchers used advanced techniques like HPLC-ESI-MS/MS to analyze ascaroside compounds in Caenorhabditis nematodes and discovered unique ascaroside dimers specific to different species.
  • They identified the structures of these dimers through various spectrometric methods and confirmed their findings by synthesizing examples in the lab.
  • The study showed that certain male nematodes are attracted exclusively to ascaroside dimers from their own species, suggesting a new way species communicate using these specialized signaling molecules.

Article Abstract

Comparative ascaroside profiling of Caenorhabditis nematodes using HPLC-ESI-(-)-MS/MS precursor ion scanning revealed a class of highly species-specific ascaroside dimers. Their 2- and 4-isomeric, homo- and heterodimeric structures were identified using a combination of HPLC-ESI-(+)-HR-MS/MS spectrometry and high-resolution dqf-COSY NMR spectroscopy. Structure assignments were confirmed by total synthesis of representative examples. Functional characterization using holding assays indicated that males of Caenorhabditis remanei and Caenorhabditis nigoni are exclusively retained by their conspecific ascaroside dimers, demonstrating that dimerization of conserved monomeric building blocks represents a yet undescribed mechanism that generates species-specific signaling molecules in the Caenorhabditis genus.

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Source
http://dx.doi.org/10.1039/d0ob00799dDOI Listing

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