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dc.contributor.authorZiesche, Lisa
dc.contributor.authorWolter, Laura
dc.contributor.authorWang, Hui
dc.contributor.authorBrinkhoff, Thorsten
dc.contributor.authorPohlner, Marion
dc.contributor.authorEngelen, Bert
dc.contributor.authorWagner-Döbler, Irene
dc.contributor.authorSchulz, Stefan
dc.date.accessioned2019-01-30T10:34:41Z
dc.date.available2019-01-30T10:34:41Z
dc.date.issued2018-12-31
dc.identifier.issn1660-3397
dc.identifier.pmid30602652
dc.identifier.doi10.3390/md17010020
dc.identifier.urihttp://hdl.handle.net/10033/621673
dc.description.abstractN-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-Texten_US
dc.publisherMPDIen_US
dc.rightsAttribution-NonCommercial-ShareAlike 4.0 International*
dc.rights.urihttp://creativecommons.org/licenses/by-nc-sa/4.0/*
dc.subjectAHLen_US
dc.subjectHeck couplingen_US
dc.subjectRhodobacteraceaeen_US
dc.subjectautoinducersen_US
dc.subjectbacterial signalingen_US
dc.subjectgas chromatographyen_US
dc.subjectmass spectrometryen_US
dc.subjectquorum-sensingen_US
dc.subjectsedimenten_US
dc.subjectstructure elucidationen_US
dc.titleAn Unprecedented Medium-Chain Diunsaturated -acylhomoserine Lactone from Marine Group Bacteria.en_US
dc.typeArticleen_US
dc.contributor.departmentHZI,Helmholtz-Zentrum für Infektionsforschung GmbH, Inhoffenstr. 7,38124 Braunschweig, Germany.en_US
dc.identifier.journalMarine Drugsen_US
refterms.dateFOA2019-01-30T10:34:41Z
dc.source.journaltitleMarine drugs


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