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

Chuanfu Dong; Franziska Dolke; Siva Bandi; Christian Paetz; Stephan H. von Reuß

doi:10.1039/D0OB00799D

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

Chuanfu Dong,

‡§^a Franziska Dolke,‡^a Siva Bandi,

^b Christian Paetz

^c and Stephan H. von Reuß

*^ab

Author affiliations

* Corresponding authors

^a Department of Bioorganic Chemistry, Max Planck Institute for Chemical Ecology, Hans-Knöll Straße 8, D-07745 Jena, Germany

^b Laboratory for Bioanalytical Chemistry, Institute of Chemistry, University of Neuchâtel, Avenue de Bellevaux 51, CH-2000 Neuchâtel, Switzerland
E-mail: stephan.vonreuss@unine.ch

^c Research Group Biosynthesis/NMR, Max Planck Institute for Chemical Ecology, Hans-Knöll Straße 8, D-07745 Jena, Germany

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.

This article is part of the themed collection: Chemical Biology in OBC

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DOI: https://doi.org/10.1039/D0OB00799D
Article type: Paper
Submitted: 17 Apr 2020
Accepted: 23 Jun 2020
First published: 24 Jun 2020
This article is Open Access

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Org. Biomol. Chem., 2020,18, 5253-5263

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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, 18, 5253 DOI: 10.1039/D0OB00799D

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Organic & Biomolecular Chemistry

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

Abstract

Supplementary files

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

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