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Determination of diketopiperazines of Burkholderia cepacia CF-66 by gas chromatography–mass spectrometry

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Abstract

Bacteria communicate with each other by a process termed “quorum sensing” (QS), and diffusible, low-molecular-weight chemicals, called signal molecules, are used as the communication languages. In cell-free Burkholderia cepacia CF-66 culture supernatants, five compounds suspected of being signal molecules were identified. The gene (cepI) related with AHLs synthesis were not detected by polymerase chain reaction (PCR) using specific primers. Gas chromatography–mass spectrometry (GC–MS) revealed that these compounds were not AHLs but the diketopiperazines (DKPs) cyclo(Pro–Phe), cyclo(Pro–Tyr), cyclo(Ala–Val), cyclo(Pro–Leu), and cyclo(Pro–Val), all of which were both d and l-type. Four kinds of DKPs had been isolated from other Gram-negative bacteria, but the other was a novel kind discovered in CF-66, and l-cyclo (Pro–Phe) was quantified by GC–MS. It was found that exogenous DKPs had a negative effect on the candidacidal activity of the culture supernatant extracts.

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Abbreviations

QS:

Quorum sensing

CF-66:

Burkholderia cepacia CF-66

GC–MS:

Gas chromatography-mass spectrometry

DKPs:

Diketopiperazines

AHL:

Acyl-homoserine lactone

References

  1. Nealson KH, Hastings JW (1979) Bacterial bioluminescence: its control and ecological significance. Microbiol Rev 43:496–518

    CAS  Google Scholar 

  2. Federle MJ, Bassler BL (2003) Interspecies communication in bacteria. J Clin Invest 112:1291–1299

    CAS  Google Scholar 

  3. Fuqua WC, Winans SC, Greenberg EP (1994) Quorum sensing in bacteria: the LuxR/LuxI family of cell density-responsive transcriptional regulators. J Bacteriol 176:269–275

    CAS  Google Scholar 

  4. Novick RP (2003) Autoinduction and signal transduction in the regulation of staphylococcal virulence. Mol Microbiol 48:1429–1449

    Article  CAS  Google Scholar 

  5. Schauder S, Shokat K, Surette MG, Bassler BL (2001) The LuxS family of bacterial autoinducers: biosynthesis of a novel quorum-sensing signal molecule. Mol Microbiol 41:463–476

    Article  CAS  Google Scholar 

  6. Reading NC, Sperandio V (2006) Quorum sensing: the many languages of bacteria. FEMS Microbiol Lett 254:1–11

    Article  CAS  Google Scholar 

  7. Gallagher LA, McKnight SL, Kuznetsova MS, Pesci EC, Manoil C (2002) Functions required for extracellular quinolone signaling by Pseudomonas aeruginosa. J Bacteriol 184:6472–6480

    Article  CAS  Google Scholar 

  8. Venturi V, Friscina A, Bertani I, Devescovi G, Aguilar C (2004) Quorum sensing in Burkholderi cepacia complex. Res Microbiol 155:238–244

    Article  CAS  Google Scholar 

  9. Williams P (2007) Quorum sensing, communication and cross-kingdom signaling in the bacterial world. Microbiology 153:3923–3938

    Article  CAS  Google Scholar 

  10. Shiner EK, Rumbaugh KP, Williams SC (2005) Interkingdom signaling: deciphering the language of acyl-homoserine lactones. FEMS Microbiol Rev 29:935–947

    Article  CAS  Google Scholar 

  11. Quan CS, Zheng W, Liu Q, Ohta Y, Fan SD (2006) Isolation and characterization of a novel Burkholderia cepacia with strong antifungal activity against Rhizoctonia solani. Appl Microbiol Biotech 72:1276–1284

    Article  CAS  Google Scholar 

  12. Li X, Quan CS, Fan SD (2007) Antifungal activity of a novel compound from Burkholderi cepacia against plant pathogenic fungi. Lett Appl Microbiol 45:508–514

    Article  CAS  Google Scholar 

  13. Holden MTG, Chhabra SR, Denys R, Stead P, Bainton NJ, Hill JP, Manefield M, Kumar N et al (1999) Quorum sensing cross talk: isolation and chemical characterization of cyclic dipeptides from Pseudomonas aeruginosa and other Gram-negative bacteria. Mol Microbiol 33:1254–1266

    Article  CAS  Google Scholar 

  14. Degrassi G, Aguilar C, Bosco M, Zahariev S, Pongor S, Ventui V (2002) Plant growth-promoting Pseudomonas putida WCS358 produces and secretes four cyclic dipeptides: cross-talk with quorum sensing bacteria sensors. Curr Microbiol 45:250–254

    Article  CAS  Google Scholar 

  15. Li X, Quan CS, Yu HY, Fan SD (2008) Multiple effects of a novel compound from Burkholderia cepacia against Candida albicans. FEMS Microbiol Lett 285:250–256

    Article  CAS  Google Scholar 

  16. Skwierczynski RD, Connors KA (1993) Demethylation kinetics of aspartame and l-phenylalanine methyl-ester in aqueous-solution. Pharm Res 10:1174–1180

    Article  CAS  Google Scholar 

  17. Steindle L, Venturi V (2007) Detection of quorum-sensing N -acyl homoserine lactone signal molecules by bacterial biosensors. FEMS Microbiol Lett 266:1–9

    Article  Google Scholar 

  18. Yang YH, Lee TH, Kim JH, Kim EJ, Joo HS, Lee CS, Kim BG (2006) High-throughput detection method of quorum-sensing molecules by colorimetry and its applications. Anal Biochem 356:297–299

    Article  CAS  Google Scholar 

  19. Shaw PD, Ping G, Daly SL, Cha C, Cronan JE, Rinehart KL, Farrand SK (1997) Detecting and characterizing N-acyl-homoserine lactone signal molecules by thin layer chromatography. Biochem J 94:6036–6041

    CAS  Google Scholar 

  20. Fekete A, Frommberger M, Rothballer M, Li XJ, Englmann M, Fekete J, Hartmann A, Eberl L et al (2007) 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

    Article  CAS  Google Scholar 

  21. Cataldi TRI, Bianco G, Palazzo L, Quaranta V (2007) Occurrence of N-acyl-l-homoserine lactones in extracts of some Gram-negative bacteria evaluated by gas chromatography–mass spectrometry. Anal Biochem 361:226–235

    Article  CAS  Google Scholar 

  22. Teplitski M, Eberhard A, Gronquist MR, Gao M, Robinson JB, Bauer WD (2003) Chemical identification of N-acyl homoserine lactone quorum-sensing signals produced by Sinorhizobium meliloti strains in defined medium. Arch Microbiol 180:494–497

    Article  CAS  Google Scholar 

  23. Barnard AML, Salmond GPC (2004) Quorum sensing: the complexities of chemical communication between bacteria. Complexus 5:87–101

    Article  Google Scholar 

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Acknowledgements

I would particularly like to acknowledge the support my advisor Chunshan Quan, Dr Xin Li, and MS Xiaohui Qi gave me. This work was supported by a grant from the Scientific Research Foundation for Returned Overseas Chinese Scholars, State Education Ministry (N.O. 20052101).

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Correspondence to Chun-Shan Quan.

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Wang, JH., Quan, CS., Qi, XH. et al. Determination of diketopiperazines of Burkholderia cepacia CF-66 by gas chromatography–mass spectrometry. Anal Bioanal Chem 396, 1773–1779 (2010). https://doi.org/10.1007/s00216-009-3379-3

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  • DOI: https://doi.org/10.1007/s00216-009-3379-3

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