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

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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.

Graphical abstract: Dimerization of conserved ascaroside building blocks generates species-specific male attractants in Caenorhabditis nematodes

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Supplementary files

Article information


Submitted
17 Apr 2020
Accepted
23 Jun 2020
First published
24 Jun 2020

This article is Open Access

Org. Biomol. Chem., 2020, Advance Article
Article type
Paper

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

C. Dong, F. Dolke, S. Bandi, C. Paetz and S. H. von Reuß, Org. Biomol. Chem., 2020, Advance Article , DOI: 10.1039/D0OB00799D

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