How Important Is the Absolute Configuration to Bacteria Quorum Sensing and Quorum Quenching?

  • Francisca Diana da Silva Araújo
  • Armando Mateus Pomini
  • Anita Jocelyne Marsaioli


Bacteria communicate with each other by producing and detecting small diffusible molecules in a process called quorum sensing (QS). This mechanism allows bacteria to coordinate their activities in response to their populations. For instance, QS regulates diverse phenotypes, such as virulence factors bioluminescence, biofilm formation, and antibiotic production, in various bacteria that survived in plants and mammals, only after reaching critical populations (Waters and Bassler 2005).


Quorum Sense Absolute Configuration Homoserine Lactone Enantiomeric Ratio Quorum Quenching 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.


  1. Ansaldi M, Marolt D, Stebe T, Mandic-Mulec I, Dubnau D (2002) Specific activation of the Bacillus quorum-sensing systems by isoprenylated pheromone variants. Mol Microbiol 44:1561–1573. doi: 10.1046/j.1365-2958.2002.02977.x PubMedCrossRefGoogle Scholar
  2. Araújo FDS, Esper LMR, Kuaye AY, Sircili MP, Marsaioli AJ (2012) N-acyl-homoserine lactones from Enterobacter sakazakii (Cronobacter spp.) and their degradation by Bacillus cereus enzymes. J Agric Food Chem 60:585–592. doi: 10.1021/jf203846f PubMedCrossRefGoogle Scholar
  3. Bainton NJ, Stead P, Chhabra SR, Bycroft BW, Salmond GP, Stewart GS, Williams PN (1992) N-(3-Oxohexanoyl)-L-homoserine lactone regulates carbapenem antibiotic production in Erwinia carotovora. Biochem J 288:997–1004PubMedPubMedCentralGoogle Scholar
  4. Buser HR, Arn H, Guerin P, Rauscher S (1983) Determination of double bond position in mono-unsaturated acetates by mass spectrometry of dimethyl disulfide adducts. Anal Chem 55:818–822. doi: 10.1021/ac00257a003 CrossRefGoogle Scholar
  5. Cao J, Meighen E (1993) Biosynthesis and stereochemistry of the autoinducer controlling luminescence in Vibrio harveyi. J Bacteriol 175:3856–3862. doi: 10.1002/cmdc.200900180 PubMedPubMedCentralGoogle Scholar
  6. Chen X, Schauder S, Potier N, Van Dorsselaer A, Pelczer I, Bassler BL, Hughson FM (2002) Structural identification of a bacterial quorum-sensing signal containing boron. Nature 415:545–549. doi: 10.1038/415545a PubMedCrossRefGoogle Scholar
  7. Chhabra SR, Stead P, Bainton NJ, Salmond GPC, Stewart GSAB, Williams PJ (1993) Autoregulation of carbapenem biosynthesis in Erwinia carotovora by analogues of N-(3-oxohexanoyl)-L-homoserine lactone. J Antibiot 46:441–454PubMedCrossRefGoogle Scholar
  8. Eberhard A, Burlingame AL, Eberhard C, Kenyon GL, Nealson KH, Oppenheimer NJ (1981) Structural identification of autoinducer of Photobacterium fischeri luciferase. Biochemistry 20:2444–2449. doi: 10.1021/bi00512a013 PubMedCrossRefGoogle Scholar
  9. Fuqua WC, Winans SC (1994) A LuxR-LuxI type regulatory system activates Agrobacterium Ti plasmid conjugal transfer in the presence of a plant tumor metabolite. J Bacteriol 176:2796–2806PubMedPubMedCentralGoogle Scholar
  10. Garcia-Aljaro C, Eberl L, Riedel K, Blanch AR (2008) Detection of quorum-sensing-related molecules in Vibrio scophthalmi. BMC Microbiol 8:138. doi: 10.1186/1471-2180-8-138 PubMedCrossRefPubMedCentralGoogle Scholar
  11. Higgins DA, Pomianek ME, Kraml CM, Taylor RK, Semmelhack MF, Bassler BL (2007) The major Vibrio cholerae autoinducer and its role in virulence factor production. Nature 450:883–886. doi: 10.1038/nature06284 PubMedCrossRefGoogle Scholar
  12. Ji G, Beavis RC, Novick RP (1995) Cell density control of staphylococcal virulence mediated by an octapeptide pheromone. Proc Natl Acad Sci U S A 92:12055–12059. doi: 10.1073/pnas.92.26.12055 PubMedCrossRefPubMedCentralGoogle Scholar
  13. Kai K, Kasamatsu K, Hayashi H (2012) (Z)-N-(4-Decenoyl)homoserine lactone, a new quorum-sensing molecule, produced by endobacteria associated with Mortierella alpina A-178. Tetrahedron Lett 53:5441–5444. doi: 10.1016/j.tetlet.2012.07.133 CrossRefGoogle Scholar
  14. Lindemann A, Pessi G, Schaefer AL, Mattmann ME, Christensen QH, Kessler A, Hennecke H, Blackwell HE, Greenberg EP, Harwood CS (2011) Isovaleryl-homoserine lactone, an unusual branched-chain quorum-sensing signal from the soybean symbiont Bradyrhizobium japonicum. Proc Natl Acad Sci U S A 108:16765–16770. doi: 10.1073/pnas.1114125108 PubMedCrossRefPubMedCentralGoogle Scholar
  15. Lithgow JK, Wilkinson A, Hardman A, Rodelas B, Wisniewski-Dyé F, Williams P, Downie JA (2000) The regulatory locus cinRI in Rhizobium leguminosarum controls a network of quorum-sensing loci. Mol Microbiol 37:81–97. doi: 10.1046/j.1365-2958.2000.01960.x PubMedCrossRefGoogle Scholar
  16. Meijler MM, Hom LG, Kaufmann GF, McKenzie KM, Sun C, Moss JA, Matsushita M, Janda KD (2004) Synthesis and biological validation of a ubiquitous quorum-sensing molecule. Angew Chem Int Ed Engl 43:2106–2108. doi: 10.1002/anie.200353150 PubMedCrossRefGoogle Scholar
  17. Miller DR, Borden JH, Slessor KNJ (1989) Inter- and intrapopulation variation of the pheromone, ipsdienol produced by male pine engravers, Ips pini (Say) (Coleoptera: Scolytidae). J Chem Ecol 15:233–247. doi: 10.1007/BF02027785 PubMedCrossRefGoogle Scholar
  18. Miller MB, Skorupski K, Lenz DH, Taylor RK, Bassler BL (2002) Parallel quorum sensing systems converge to regulate virulence in Vibrio cholerae. Cell 110:303–314. doi: 10.1016/S0092-8674(02)00829-2 PubMedCrossRefGoogle Scholar
  19. Miller ST, Xavier KB, Campagna SR, Taga ME, Semmelhack MF, Bassler BL, Hughson FM (2004) Salmonella typhimurium recognizes a chemically distinct form of the bacterial quorum-sensing signal AI-2. Mol Cell 15:677–687. doi: 10.1016/j.molcel.2004.07.020 PubMedCrossRefGoogle Scholar
  20. Perez LJ, Ng WL, Marano P, Brook K, Bassler BL, Semmelhack MF (2012) Role of the CAI-1 fatty acid tail in the Vibrio cholerae quorum sensing response. J Med Chem 55:9669–9681. doi: 10.1021/jm300908t PubMedCrossRefPubMedCentralGoogle Scholar
  21. Pomini AM, Marsaioli AJ (2008) Absolute configuration and antimicrobial activity of acylhomoserine lactones. J Nat Prod 71:1032–1036. doi: 10.1021/np800127b PubMedCrossRefGoogle Scholar
  22. Pomini AM, Araújo WL, Marsaioli AJ (2006) Structural elucidation and biological activity of acyl-homoserine lactones from the phytopathogen Pantoea ananatis Serrano 1928. J Chem Ecol 32:1769–1778. doi: 10.1007/s10886-006-9108-x PubMedCrossRefGoogle Scholar
  23. Pomini AM, Gai C, Cruz PR, Araujo WL, Marsaioli AJJ (2009) Long-chain acyl-homoserine lactones from Methylobacterium mesophilicum: synthesis and absolute configuration. J Nat Prod 72:2125–2129. doi: 10.1021/np900043j PubMedCrossRefGoogle Scholar
  24. Roche DM, Byers JT, Smith DS, Glansdorp FG, Spring DR, Welch M (2004) Communications blackout? Do N-acylhomoserine-lactone-degrading enzymes have any role in quorum sensing? Microbiology 150:2023–2028. doi: 10.1099/mic.0.26977-0 PubMedCrossRefGoogle Scholar
  25. Schaefer AL, Greenberg EP, Oliver CM, Oda Y, Huang JJ, Bittan-Banin G, Peres CM, Schmidt S, Juhaszova K, Sufrin JR, Harwood CS (2008) A new class of homoserine lactone quorum-sensing signals. Nature 454:595–599. doi: 10.1038/nature07088 PubMedCrossRefGoogle Scholar
  26. Schaeffer AL, Val DL, Hamzelka BL, Cronan JE, Greenberg EP (1996) Generation of cell-to-cell signals in quorum sensing: acyl homoserine lactone synthase activity of a purified Vibrio fischeri LuxI protein. Proc Natl Acad Sci U S A 93:9505–9509. doi: 10.1073/pnas.93.18.9505 CrossRefGoogle Scholar
  27. Schripsema J, deRudder K, vanVliet T, Lankhorst P, deVroom E, Kijne J, vanBrussel A (1996) 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 Bacteriol 178:366–371PubMedPubMedCentralGoogle Scholar
  28. Stacy D, Welsh MA, Rather PN, Blackwell HE (2012) Attenuation of quorum sensing in the pathogen Acinetobacter baumannii using non-native N-Acyl homoserine lactones. ACS Chem Biol 7:1719–1728. doi: 10.1021/cb300351x PubMedCrossRefPubMedCentralGoogle Scholar
  29. Thiel V, Kunze B, Verma P, Wagner-Döbler I, Schulz S (2009) New structural variants of homoserine lactones in bacteria. ChemBioChem 10:1861–1868. doi: 10.1002/cbic.200900126 PubMedCrossRefGoogle Scholar
  30. Waters CM, Bassler BL (2005) Quorum sensing: cell-to-cell communication in bacteria. Annu Rev Cell Dev Biol 21:319–346. doi: 10.1146/annurev.cellbio.21.012704.131001 PubMedCrossRefGoogle Scholar

Copyright information

© Springer India 2015

Authors and Affiliations

  • Francisca Diana da Silva Araújo
    • 1
  • Armando Mateus Pomini
    • 2
  • Anita Jocelyne Marsaioli
    • 1
  1. 1.Chemistry InstituteState University of Campinas, UNICAMPCampinasBrazil
  2. 2.Department of Chemistry, Center of Exact SciencesState University of MaringáMaringáBrazil

Personalised recommendations