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Mar. Drugs 2019, 17(1), 20; https://doi.org/10.3390/md17010020

An Unprecedented Medium-Chain Diunsaturated N-acylhomoserine Lactone from Marine Roseobacter Group Bacteria

1
Institute of Organic Chemistry, Technische Universität Braunschweig, Hagenring 30, 38106 Braunschweig, Germany
2
Institute for Chemistry and Biology of the Marine Environment, University of Oldenburg, Carl-von-Ossietzky-Straße 9-11, 26111 Oldenburg, Germany
3
Helmholtz Centre for Infection Research, Department of Medical Microbiology, Group Microbial Communication, Inhoffenstr. 7, 38124 Braunschweig, Germany
*
Author to whom correspondence should be addressed.
Received: 7 December 2018 / Revised: 20 December 2018 / Accepted: 21 December 2018 / Published: 31 December 2018
(This article belongs to the Special Issue Bioprospecting of Marine Microorganisms)
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Abstract

N-acylhomoserine lactones (AHLs), bacterial signaling compounds involved in quorum-sensing, are a structurally diverse group of compounds. We describe here the identification, synthesis, occurrence and biological activity of a new AHL, N-((2E,5Z)-2,5-dodecadienoyl)homoserine lactone (11) and its isomer N-((3E,5Z)-3,5-dodecadienoyl)homoserine lactone (13), occurring in several Roseobacter group bacteria (Rhodobacteraceae). The analysis of 26 strains revealed the presence of 11 and 13 in six of them originating from the surface of the macroalgae Fucus spiralis or sediments from the North Sea. In addition, 18 other AHLs were detected in 12 strains. Compound identification was performed by GC/MS. Mass spectral analysis revealed a diunsaturated C12 homoserine lactone as structural element of the new AHL. Synthesis of three likely candidate compounds, 11, 13 and N-((2E,4E)-2,4-dodecadienoyl)homoserine lactone (5), revealed the former to be the natural AHLs. Bioactivity test with quorum-sensing reporter strains showed high activity of all three compounds. Therefore, the configuration and stereochemistry of the double bonds in the acyl chain seemed to be unimportant for the activity, although the chains have largely different shapes, solely the chain length determining activity. In combination with previous results with other Roseobacter group bacteria, we could show that there is wide variance between AHL composition within the strains. Furthermore, no association of certain AHLs with different habitats like macroalgal surfaces or sediment could be detected. View Full-Text
Keywords: quorum-sensing; structure elucidation; Rhodobacteraceae; autoinducers; bacterial signaling; Heck coupling; mass spectrometry; gas chromatography; sediment; AHL quorum-sensing; structure elucidation; Rhodobacteraceae; autoinducers; bacterial signaling; Heck coupling; mass spectrometry; gas chromatography; sediment; AHL
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Ziesche, L.; Wolter, L.; Wang, H.; Brinkhoff, T.; Pohlner, M.; Engelen, B.; Wagner-Döbler, I.; Schulz, S. An Unprecedented Medium-Chain Diunsaturated N-acylhomoserine Lactone from Marine Roseobacter Group Bacteria. Mar. Drugs 2019, 17, 20.

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