J. Bacteriol., 01 1996, 366-371, Vol 178, No. 2
Copyright © 1996, American Society for Microbiology

Bacteriocin small of Rhizobium leguminosarum belongs to the class of N- acyl-L-homoserine lactone molecules, known as autoinducers and as quorum sensing co-transcription factors

J Schripsema, KE de Rudder, TB van Vliet, PP Lankhorst, E de Vroom, JW Kijne and AA van Brussel
Division of Pharmacognosy, Gorlaeus Laboratories, Leiden, and Gist, The Netherlands.

Small bacteriocin was isolated from the culture broth of the gram- negative bacterium Rhizobium leguminosarum, which forms symbiotic nitrogen-fixing root nodules on a number of leguminous plants. The structure of the molecule was elucidated by spectroscopic methods and identified as N-(3R-hydroxy-7-cis-tetradecanoyl)-L-homoserine lactone. The absolute configuration of both asymmetric carbon atoms in the molecule was determined by the use of the chiral solvating agents S-(+)- and R-(-)-2,2,2-trifluoro-1-(9-anthryl)-ethanol. small bacteriocin is structurally related to the quorum sensing co-transcription factors for genes from other bacteria such as Vibrio fischeri, Pseudomonas aeruginosa, Erwinia carotovora, and Agrobacterium tumefaciens which are involved in animal-microbe or plant-microbe interactions. The mechanism of regulation of such interactions by this kind of co-transcription factors is still unknown in R. leguminosarum.

This article has been cited by other articles:

• Krick, A., Kehraus, S., Eberl, L., Riedel, K., Anke, H., Kaesler, I., Graeber, I., Szewzyk, U., Konig, G. M. (2007). A Marine Mesorhizobium sp. Produces Structurally Novel Long-Chain N-Acyl-L-Homoserine Lactones. Appl. Environ. Microbiol. 73: 3587-3594 [Abstract] [Full Text]  
• Gonzalez, J. E., Keshavan, N. D. (2006). Messing with Bacterial Quorum Sensing. Microbiol. Mol. Biol. Rev. 70: 859-875 [Abstract] [Full Text]  
• Wang, Y.-J., Leadbetter, J. R. (2005). Rapid Acyl-Homoserine Lactone Quorum Signal Biodegradation in Diverse Soils. Appl. Environ. Microbiol. 71: 1291-1299 [Abstract] [Full Text]  
• Ulrich, R. L. (2004). Quorum Quenching: Enzymatic Disruption of N-Acylhomoserine Lactone-Mediated Bacterial Communication in Burkholderia thailandensis. Appl. Environ. Microbiol. 70: 6173-6180 [Abstract] [Full Text]  
• Hoang, H. H., Becker, A., Gonzalez, J. E. (2004). The LuxR Homolog ExpR, in Combination with the Sin Quorum Sensing System, Plays a Central Role in Sinorhizobium meliloti Gene Expression. J. Bacteriol. 186: 5460-5472 [Abstract] [Full Text]  
• Gonzalez, J. E., Marketon, M. M. (2003). Quorum Sensing in Nitrogen-Fixing Rhizobia. Microbiol. Mol. Biol. Rev. 67: 574-592 [Abstract] [Full Text]  
• Luo, Z.-Q., Smyth, A. J., Gao, P., Qin, Y., Farrand, S. K. (2003). Mutational Analysis of TraR. CORRELATING FUNCTION WITH MOLECULAR STRUCTURE OF A QUORUM-SENSING TRANSCRIPTIONAL ACTIVATOR. J. Biol. Chem. 278: 13173-13182 [Abstract] [Full Text]  
• He, X., Chang, W., Pierce, D. L., Seib, L. O., Wagner, J., Fuqua, C. (2003). Quorum Sensing in Rhizobium sp. Strain NGR234 Regulates Conjugal Transfer (tra) Gene Expression and Influences Growth Rate. J. Bacteriol. 185: 809-822 [Abstract] [Full Text]  
• Loh, J., Carlson, R. W., York, W. S., Stacey, G. (2002). Bradyoxetin, a unique chemical signal involved in symbiotic gene regulation. Proc. Natl. Acad. Sci. USA 99: 14446-14451 [Abstract] [Full Text]  
• Marketon, M. M., Gronquist, M. R., Eberhard, A., Gonzalez, J. E. (2002). Characterization of the Sinorhizobium meliloti sinR/sinI Locus and the Production of Novel N-Acyl Homoserine Lactones. J. Bacteriol. 184: 5686-5695 [Abstract] [Full Text]  
• Wilkinson, A., Danino, V., Wisniewski-Dye, F., Lithgow, J. K., Downie, J. A. (2002). N-Acyl-Homoserine Lactone Inhibition of Rhizobial Growth Is Mediated by Two Quorum-Sensing Genes That Regulate Plasmid Transfer. J. Bacteriol. 184: 4510-4519 [Abstract] [Full Text]  
• Gram, L., Grossart, H.-P., Schlingloff, A., Kiorboe, T. (2002). Possible Quorum Sensing in Marine Snow Bacteria: Production of Acylated Homoserine Lactones by Roseobacter Strains Isolated from Marine Snow. Appl. Environ. Microbiol. 68: 4111-4116 [Abstract] [Full Text]  
• Marketon, M. M., Gonzalez, J. E. (2002). Identification of Two Quorum-Sensing Systems in Sinorhizobium meliloti. J. Bacteriol. 184: 3466-3475 [Abstract] [Full Text]  
• Daniels, R., De Vos, D. E., Desair, J., Raedschelders, G., Luyten, E., Rosemeyer, V., Verreth, C., Schoeters, E., Vanderleyden, J., Michiels, J. (2002). The cin Quorum Sensing Locus of Rhizobium etli CNPAF512 Affects Growth and Symbiotic Nitrogen Fixation. J. Biol. Chem. 277: 462-468 [Abstract] [Full Text]  
• Steidle, A., Sigl, K., Schuhegger, R., Ihring, A., Schmid, M., Gantner, S., Stoffels, M., Riedel, K., Givskov, M., Hartmann, A., Langebartels, C., Eberl, L. (2001). Visualization of N-Acylhomoserine Lactone-Mediated Cell-Cell Communication between Bacteria Colonizing the Tomato Rhizosphere. Appl. Environ. Microbiol. 67: 5761-5770 [Abstract] [Full Text]  
• Blosser-Middleton, R. S., Gray, K. M. (2001). Multiple N-Acyl Homoserine Lactone Signals of Rhizobium leguminosarum Are Synthesized in a Distinct Temporal Pattern. J. Bacteriol. 183: 6771-6777 [Abstract] [Full Text]  
• Laue, B. E., Jiang, Y., Chhabra, S. R., Jacob, S., Stewart, G. S. A. B., Hardman, A., Downie, J. A., O’Gara, F., Williams, P. (2000). The biocontrol strain Pseudomonas fluorescens F113 produces the Rhizobium small bacteriocin, N-(3-hydroxy-7-cis-tetradecenoyl)homoserine lactone, via HdtS, a putative novel N-acylhomoserine lactone synthase. Microbiology 146: 2469-2480 [Abstract] [Full Text]  
• de Kievit, T. R., Iglewski, B. H. (2000). Bacterial Quorum Sensing in Pathogenic Relationships. Infect. Immun. 68: 4839-4849 [Full Text]  
• Forsyth, M. H., Cover, T. L. (2000). Intercellular Communication in Helicobacter pylori: luxS Is Essential for the Production of an Extracellular Signaling Molecule. Infect. Immun. 68: 3193-3199 [Abstract] [Full Text]  
• Oresnik, I. J., Twelker, S., Hynes, M. F. (1999). Cloning and Characterization of a Rhizobium leguminosarum Gene Encoding a Bacteriocin with Similarities to RTX Toxins. Appl. Environ. Microbiol. 65: 2833-2840 [Abstract] [Full Text]  
• Rodelas, B., Lithgow, J. K., Wisniewski-Dye, F., Hardman, A., Wilkinson, A., Economou, A., Williams, P., Downie, J. A. (1999). Analysis of Quorum-Sensing-Dependent Control of Rhizosphere-Expressed (rhi) Genes in Rhizobium leguminosarum bv. viciae. J. Bacteriol. 181: 3816-3823 [Abstract] [Full Text]  
• Thorne, S. H., Williams, H. D. (1999). Cell Density-Dependent Starvation Survival of Rhizobium leguminosarum bv. phaseoli: Identification of the Role of an N-Acyl Homoserine Lactone in Adaptation to Stationary-Phase Survival. J. Bacteriol. 181: 981-990 [Abstract] [Full Text]  
• Zhu, J., Beaber, J. W., Moré, M. I., Fuqua, C., Eberhard, A., Winans, S. C. (1998). Analogs of the Autoinducer 3-Oxooctanoyl-Homoserine Lactone Strongly Inhibit Activity of the TraR Protein of Agrobacterium tumefaciens. J. Bacteriol. 180: 5398-5405 [Abstract] [Full Text]  
• Storey, D. G., Ujack, E. E., Rabin, H. R., Mitchell, I. (1998). Pseudomonas aeruginosa lasR Transcription Correlates with the Transcription of lasA, lasB, and toxA in Chronic Lung Infections Associated with Cystic Fibrosis. Infect. Immun. 66: 2521-2528 [Abstract] [Full Text]  
• Rosemeyer, V., Michiels, J., Verreth, C., Vanderleyden, J. (1998). luxI- and luxR-Homologous Genes of Rhizobium etli CNPAF512 Contribute to Synthesis of Autoinducer Molecules and Nodulation of Phaseolus vulgaris. J. Bacteriol. 180: 815-821 [Abstract] [Full Text]  
• Srinivasan, S., Östling, J., Charlton, T., Nys, R. d., Takayama, K., Kjelleberg, S. (1998). Extracellular Signal Molecule(s) Involved in the Carbon Starvation Response of Marine Vibrio sp. Strain S14. J. Bacteriol. 180: 201-209 [Abstract] [Full Text]