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Applied and Environmental Microbiology, June 2007, p. 3587-3594, Vol. 73, No. 11
0099-2240/07/$08.00+0     doi:10.1128/AEM.02344-06
Copyright © 2007, American Society for Microbiology. All Rights Reserved.

A Marine Mesorhizobium sp. Produces Structurally Novel Long-Chain N-Acyl-L-Homoserine Lactones{triangledown}

Anja Krick,1 Stefan Kehraus,1 Leo Eberl,2 Kathrin Riedel,2 Heidrun Anke,3 Ines Kaesler,4 Ingeborg Graeber,4 Ulrich Szewzyk,4 and Gabriele M. König1*

Institute for Pharmaceutical Biology, University of Bonn, Nussallee 6, D-53115 Bonn, Germany,1 Department of Microbiology, Institute of Plant Biology, University of Zürich, Zollikerstr. 107, CH-8008 Zürich, Switzerland,2 Institute of Biotechnology and Drug Research, Erwin-Schroedinger-Str. 56, D-67663 Kaiserslautern, Germany,3 Environmental Microbiology Group, Berlin University of Technology, Franklinstrasse 29, Sekr. FR1-2, D-10587 Berlin, Germany4

Received 4 October 2006/ Accepted 24 March 2007

Our study focused on a Mesorhizobium sp. that is phylogenetically affiliated by 16S rRNA gene sequence to other marine and saline bacteria of this genus. Liquid chromatography-mass spectrometry investigations of the extract obtained from solid-phase extraction of cultures of this bacterium indicated the presence of several N-acyl homoserine lactones (AHLs), with chain lengths of C10 to C16. Chromatographic separation of the active bacterial extract yielded extraordinarily large amounts of two unprecedented acylated homoserine lactones, 5-cis-3-oxo-C12-homoserine lactone (5-cis-3-oxo-C12-HSL) (compound 1) and 5-cis-C12-HSL (compound 2). Quorum-sensing activity of compounds 1 and 2 was shown in two different biosensor systems [Escherichia coli MT102(pSB403) and Pseudomonas putida F117(pKR-C12)]. Furthermore, it was shown that both compounds can restore protease and pyoverdin production of an AHL-deficient Pseudomonas aeruginosa PAO1 lasI rhlI double mutant, suggesting that these signal molecules maybe used for intergenus signaling. In conclusion, these data indicate that the quorum-sensing activity of compounds 1 and 2 is modulated by the chain length and functional groups of the acyl moiety. Additionally, compound 1 showed antibacterial and cytotoxic activities.

* Corresponding author. Mailing address: Institute for Pharmaceutical Biology, University of Bonn, Nussallee 6, D-53115 Bonn, Germany. Phone: 49 228 733747. Fax: 49 228 733250. E-mail: g.koenig{at}uni-bonn.de

{triangledown} Published ahead of print on 30 March 2007.

Applied and Environmental Microbiology, June 2007, p. 3587-3594, Vol. 73, No. 11
0099-2240/07/$08.00+0     doi:10.1128/AEM.02344-06
Copyright © 2007, American Society for Microbiology. All Rights Reserved.





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