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Identification of bacterial N-acylhomoserine lactones (AHLs) with a combination of ultra-performance liquid chromatography (UPLC), ultra-high-resolution mass spectrometry, and in-situ biosensors

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Abstract

N-Acylated homoserine lactones (AHLs) are produced by Gram-negative bacteria as communication signals and are frequently studied as mediators of the “quorum sensing” response of bacterial communities. Several reports have recently been published on the identification of AHLs from different species and attempts have been made to study their role in natural habitats, for example the surface of plant roots in the rhizosphere. In this article, different analytical methods, including bacterial biosensors and chromatographic techniques, are reviewed. A concept for assignment of the structures of AHLs is also presented. The retention behaviour of derivatives of AHLs containing β-keto or hydroxyl groups and/or double bonds has been evaluated in relation to the separation behaviour of AHLs with saturated and unsubstituted alkanoyl chains. Samples have also been analysed by high resolution mass spectrometry (Fourier-transform ion-cyclotron-resonance mass spectrometry, FTICR-MS), nano liquid chromatography–electrospray ionization ion trap mass spectrometry (nano-LC–MS) and by the aid of a biosensor. The results obtained from ultra performance liquid chromatography (UPLC), FTICR-MS, nano-LC–MS, and bioassays have been compared to attempt structural characterisation of AHL without chemical synthesis of analytical standards. The method was used to identify the major AHL compound produced by the rhizosphere bacterium Acidovorax sp. N35 as N-(3-hydroxydecanoyl)homoserine lactone.

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References

  1. Hall-Stoodley L, Costerton JW, Stoodley P (2004) Nat Rev Microbiol 2:95–108

    Article  CAS  Google Scholar 

  2. Kjelleberg S, Molin S (2002) Curr Opin Microbiol 5:254–258

    Article  CAS  Google Scholar 

  3. Loh J, Pierson EA, Pierson LS, 3rd, Stacey G, Chatterjee A (2002) Curr Opin Plant Biol 5:285–290

    Article  CAS  Google Scholar 

  4. Pierson LS 3rd, Wood DW, Pierson EA (1998) Annu Rev Phytopathol 36:207–225

    Article  CAS  Google Scholar 

  5. Riedel K, Hentzer M, Geisenberger O, Huber B, Steidle A, Wu H, Hoiby N, Givskov M, Molin S, Eberl L (2001) Microbiology 147:3249–3262

    CAS  Google Scholar 

  6. Mathesius U, Mulders S, Gao M, Teplitski M, Caetano-Anolles G, Rolfe BG, Bauer WD (2003) Proc Natl Acad Sci USA 100:1444–1449

    Article  CAS  Google Scholar 

  7. Joint I, Tait K, Callow ME, Callow JA, Milton D, Williams P, Camara M (2002) Science 298:1207

    Article  Google Scholar 

  8. Schuhegger R, Ihring A, Gantner S, Bahnweg G, Knappe C, Vogg G, Hutzler P, Schmid M, Van Breusegem F, Eberl L et al (2006) Plant Cell Environ 29:909–918

    Article  CAS  Google Scholar 

  9. Henke JM, Bassler BL (2004) Trends Cell Biol 14:648–656

    Article  CAS  Google Scholar 

  10. van Loon LC, Bakker PA, Pieterse CM (1998) Annu Rev Phytopathol 36:453–483

    Article  Google Scholar 

  11. Steidle A, Sigl K, Schuhegger R, Ihring A, Schmid M, Gantner S, Stoffels M, Riedel K, Givskov M, Hartmann A et al (2001) Appl Environ Microbiol 67:5761–5770

    Article  CAS  Google Scholar 

  12. Gantner S, Schmid M, Durr C, Schuhegger R, Steidle A, Hutzler P, Langebartels C, Eberl L, Hartmann A, Dazzo FB (2006) FEMS Microbiol Ecol 56:188–194

    Article  CAS  Google Scholar 

  13. Bassler BL (1999) Curr Opin Microbiol 2:582–587

    Article  CAS  Google Scholar 

  14. Redfield RJ (2002) Trends Microbiol 10:365–370

    Article  CAS  Google Scholar 

  15. Hense BA, Kuttler C, Müller J, Rothballer M, Hartmann A, Kreft J-U (2006) Nat Rev Microbiol, submitted for publication

  16. Müller J, Kuttler C, Hense BA, Rothballer M, Hartmann A (2006) J Math Biol, in press

  17. Harms H, Zehnder AJ (1994) Appl Environ Microbiol 60:2736–2745

    CAS  Google Scholar 

  18. Gould TA, Herman J, Krank J, Murphy RC, Churchill MEA (2006) J Bacteriol 188:773–783

    Article  CAS  Google Scholar 

  19. McClean KH, Winson MK, Fish L, Taylor A, Chhabra SR, Camara M, Daykin M, Lamb JH, Swift S, Bycroft BW et al (1997) Microbiology-Sgm 143:3703–3711

    Article  CAS  Google Scholar 

  20. Middleton B, Rodgers HC, Camara M, Knox AJ, Williams P, Hardman A (2002) Fems Microbiol Lett 207:1–7

    Article  CAS  Google Scholar 

  21. Chambers CE, Visser MB, Schwab U, Sokol PA (2005) Fems Microbiol Lett 244:297–304

    Article  CAS  Google Scholar 

  22. Taminiau B, Daykin M, Swift S, Boschiroli ML, Tibor A, Lestrate P, De Bolle X, O’Callaghan D, Williams P, Letesson JJ (2002) Infect Immunol 70:3004–3011

    Article  CAS  Google Scholar 

  23. Teplitski M, Eberhard A, Gronquist MR, Gao M, Robinson JB, Bauer WD (2003) Arch Microbiol 180:494–497

    Article  CAS  Google Scholar 

  24. Milton DL, Hardman A, Camara M, Chhabra SR, Bycroft BW, Stewart GSAB, Williams P (1997) J Bacteriol 179:3004–3012

    CAS  Google Scholar 

  25. Pomini AM, Manfio GP, Araujo WL, Marsaioli AJ (2005) J Agric Food Chem 53:6262–6265

    Article  CAS  Google Scholar 

  26. Jiang Y, Camara M, Chhabra SR, Hardie KR, Bycroft BW, Lazdunski A, Salmond GPC, Stewart GSAB, Williams P (1998) Mol Microbiol 28:193–203

    Article  CAS  Google Scholar 

  27. Schupp PJ, Charlton TS, Taylor MW, Kjelleberg S, Steinberg PD (2005) Anal Bioanal Chem 383:132–137

    Article  CAS  Google Scholar 

  28. Cataldi TRI, Bianco G, Frommberger M, Schmitt-Kopplin P (2004) Rapid Commun Mass Spectrom 18:1341–1344

    Article  CAS  Google Scholar 

  29. Wagner-Dobler I, Thiel V, Eberl L, Allgaier M, Bodor A, Meyer S, Ebner S, Hennig A, Pukall R, Schulz S (2005) ChemBioChem 6:2195–2206

    Article  CAS  Google Scholar 

  30. Charlton TS, de Nys R, Netting A, Kumar N, Hentzer M, Givskov M, Kjelleberg S (2000) Environ Microbiol 2:530–541

    Article  CAS  Google Scholar 

  31. Llamas I, Quesada E, Martinez-Canovas M, Gronquist M, Eberhard A, Gonzalez JE (2005) Extremophiles 9:333–341

    Article  CAS  Google Scholar 

  32. Morin D, Grasland B, Vallee-Rehel K, Dufau C, Haras D (2003) J Chromatogr A 1002:79–92

    Article  CAS  Google Scholar 

  33. Huang JJ, Han JI, Zhang LH, Leadbetter JR (2003) Appl Environ Microbiol 69:5941–5949

    Article  CAS  Google Scholar 

  34. Michels JJ, Allain EJ, Borchardt SA, Hu PF, McCoy WF (2000) J Chromatogr A 898:153–165

    Article  CAS  Google Scholar 

  35. Frommberger M, Schmitt-Kopplin P, Ping G, Frisch H, Schmid M, Zhang Y, Hartmann A, Kettrup A (2004) Anal Bioanal Chem 378:1014–1020

    Article  CAS  Google Scholar 

  36. Frommberger M, Schmitt-Kopplin P, Menzinger F, Albrecht V, Schmid M, Eberl L, Hartmann A, Kettrup A (2003) Electrophoresis 24:3067–3074

    Article  CAS  Google Scholar 

  37. Frommberger M, Hertkorn N, Englmann M, Jakoby S, Hartmann A, Kettrup A, Schmitt-Kopplin P (2005) Electrophoresis 26:1523–1532

    Article  CAS  Google Scholar 

  38. Sambrook J, Fritsch EF, Maniatis T (1989) Cold Spring Harbor Laboratory Press, Cold Spring Harbor, New York, USA

  39. Li X, Fekete A, Englmann M, Götz C, Rothballer M, Buddrus K, Cai C, Schröder P, Hartmann A, Chen G et al (2006) J Chromatogr A, in press

  40. Shaw PD, Ping G, Daly SL, Cha C, Cronan JE Jr, Rinehart KL, Farrand SK (1997) Proc Natl Acad Sci USA 94:6036–6041

    Article  CAS  Google Scholar 

  41. Winson MK, Swift S, Fish L, Throup JP, Jorgensen F, Chhabra SR, Bycroft BW, Williams P, Stewart GS (1998) FEMS Microbiol Lett 163:185–192

    Article  CAS  Google Scholar 

  42. Kind T, Fiehn O (2006) Bmc Bioinformatics 7:234

    Article  CAS  Google Scholar 

  43. Martin AJP (1949) Biochem Soc Symp 3:4

    Google Scholar 

  44. Andersen JB, Heydorn A, Hentzer M, Eberl L, Geisenberger O, Christensen BB, Molin S, Givskov M (2001) Appl Environ Microbiol 67:575–585

    Article  CAS  Google Scholar 

  45. Thomson NR, Crow MA, McGowan SJ, Cox A, Salmond GP (2000) Mol Microbiol 36:539–556

    Article  CAS  Google Scholar 

  46. Latifi A, Winson MK, Foglino M, Bycroft BW, Stewart GS, Lazdunski A, Williams P (1995) Mol Microbiol 17:333–343

    Article  CAS  Google Scholar 

  47. Milton DL, Chalker VJ, Kirke D, Hardman A, Camara M, Williams P (2001) J Bacteriol 183:3537–3547

    Article  CAS  Google Scholar 

  48. Flodgaard LR, Dalgaard P, Andersen JB, Nielsen KF, Givskov M, Gram L (2005) Appl Environ Microbiol 71:2113–2120

    Article  CAS  Google Scholar 

  49. Bruhn JB, Christensen AB, Flodgaard LR, Nielsen KF, Larsen TO, Givskov M, Gram L (2004) Appl Environ Microbiol 70:4293–4302

    Article  CAS  Google Scholar 

  50. Lin YH, Xu JL, Hu JY, Wang LH, Ong SL, Leadbetter JR, Zhang LH (2003) Mol Microbiol 47:849–860

    Article  Google Scholar 

  51. Delalande L, Faure D, Raffoux A, Uroz S, D’Angelo-Picard C, Elasri M, Carlier A, Berruyer R, Petit A, Williams P et al (2005) Fems Microbiol Ecol 52:13–20

    Article  CAS  Google Scholar 

  52. Moon HS (2004) Arch Pharmacol Res 27(1):25–30

    Article  CAS  Google Scholar 

  53. Rasch M, Andersen JB, Nielsen KF, Flodgaard LR, Christensen H, Givskov M, Gram L (2005) Appl Environ Microbiol 71:3321–3330

    Article  CAS  Google Scholar 

Download references

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Authors and Affiliations

  1. Institute of Ecological Chemistry, GSF - National Research Center for Environment and Health, Ingolstädter Landstraße 1, 85764, Neuherberg, Germany

    Agnes Fekete, Moritz Frommberger, Xiaojing Li, Matthias Englmann & Philippe Schmitt-Kopplin

  2. Department of Rhizosphere Biology, Institute of Soil Ecology, GSF - National Research Center for Environment and Health, Ingolstädter Landstraße 1, 85764, Neuherberg, Germany

    Michael Rothballer & Anton Hartmann

  3. Ministry of Education Key Laboratory of Analysis and Detection Technology for Food Safety and Department of Chemistry, Fuzhou University, Fuzhou, Fujian, 350002, China

    Xiaojing Li

  4. Department of General and Analytical Chemistry, Faculty of Chemical Engineering, Budapest University of Technology and Economics, Gellert ter, 1111, Budapest, Hungary

    Jenoe Fekete

  5. Department of Microbiology, University of Zürich, 8008, Zürich, Switzerland

    Leo Eberl

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  1. Agnes Fekete
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  2. Moritz Frommberger
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  3. Michael Rothballer
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  4. Xiaojing Li
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  5. Matthias Englmann
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  6. Jenoe Fekete
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  7. Anton Hartmann
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  9. Philippe Schmitt-Kopplin
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Correspondence to Philippe Schmitt-Kopplin.

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Fekete, A., Frommberger, M., Rothballer, M. et al. Identification of bacterial N-acylhomoserine lactones (AHLs) with a combination of ultra-performance liquid chromatography (UPLC), ultra-high-resolution mass spectrometry, and in-situ biosensors. Anal Bioanal Chem 387, 455–467 (2007). https://doi.org/10.1007/s00216-006-0970-8

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  • DOI: https://doi.org/10.1007/s00216-006-0970-8

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