Malyngolide from the cyanobacterium Lyngbya majuscula interferes with quorum sensing circuitry

Environmental Microbiology Reports

Volumn 2, Issue 6, 2010, Pages 739-744

  Dobretsov, Sergey ^a   Teplitski, Max ^b   Alagely, Ali ^b   Gunasekera, Sarath P ^c   Paul, Valerie J ^c  

^a SULTAN QABOOS UNIVERSITY   (Oman)

^b UNIVERSITY OF FLORIDA   (United States)

^c SMITHSONIAN MARINE STATION   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BACTERIA (MICROORGANISMS); CHROMOBACTERIUM VIOLACEUM; CYANOBACTERIA; LYNGBYA; LYNGBYA MAJUSCULA; PSEUDOMONAS AERUGINOSA;

EID: 78649690544     PISSN: None     EISSN: 17582229     Source Type: Journal    
DOI: 10.1111/j.1758-2229.2010.00169.x     Document Type: Article

References (33)

1. Alagely, A., Rajamani, S., and Teplitski, M. (2010) Luminescent reporters and their applications for the characterization of signals and signal-mimics that alter LasR-mediated quorum sensing. Methods Mol Biol (in press).
2. Babler, J.H., Invergo, B.J., and Sarussi, S.J. (1980) Lactone formation via oxidative cyclization of an unsaturated carboxylic acid - application to stereoselective synthesis of (+/-) malyngolide, an antibiotic from the marine blue green alga Lyngbya majuscula Gomont. J Org Chem 45: 4241- 4243.
3. Cardellina, J.H., Moore, R.E., Arnold, E.V., and Clardy, J. (1979) Structure and absolute configuration of malyngolide, an antibiotic from the marine blue-green alga Lyngbya majuscula Gomont. J Org Chem 44: 4039-4042.
4. Cha, C., Gao, P., Chen, Y.C., Shaw, P.D., and Farrand, S.K. (1998) Production of acyl-homoserine lactone quorumsensing signals by gram-negative plant-associated bacteria. Mol Plant Microbe Interact 11: 1119-1129.
5. Chernin, L.S., Winson, M.K., Thompson, J.M., Haran, S., Bycroft, B.W., Chet, I., et al. (1998) Chitinolytic activity in Chromobacterium violaceum: substrate analysis and regulation by quorum sensing. J Bacteriol 180: 4435-4441.
6. Clark, B.R., Engene, N., Teasdale, M.E., Rowley, D.C., Matainaho, T., Valeriote, F.A., and Gerwick, W.H. (2008) Natural products chemistry and taxonomy of the marine cyanobacterium Blennothrix cantharidosmum. J Nat Prod 71: 1530-1537.
7. Dobretsov, S., Teplitski, M., and Paul, V.J. (2009) Mini review: quorum sensing in the marine environment and its relationship to biofouling. Biofouling 25: 413-427.
8. Dong, Y.H., Gusti, A.R., Zhang, Q., Xu, J.L., and Zhang, L.H. (2002) Identification of quorum-quenching N-acyl homoserine lactonases from Bacillus species. Appl Environ Microbiol 68: 1754-1759.
9. Girard, G., and Bloemberg, G.V. (2008) Central role of quorum sensing in regulating the production of pathogenicity factors in Pseudomonas aeruginosa. Future Microbiol 3: 97-106.
10. Givskov, M., Eberl, L., and Molin, S. (1997) Control of exoenzyme production, motility and cell differentiation in Serratia liquefaciens. FEMS Microbiol Lett 148: 115-122.
11. Kjelleberg, S., Steinberg, P., Givskov, M., Gram, L., Manefield, M., and de Nys, R. (1997) So marine natural products interfere with prokaryotic AHL regulatory systems? Aquat Microb Ecol 13: 85-93.
12. Koch, B., Liljefors, T., Persson, T., Nielsen, J., Kjelleberg, S., and Givskov, M. (2005) The LuxR receptor: the sites of interaction with quorum-sensing signals and inhibitors. Microbiology 151: 3589-3602.
13. Lowery, C.A., Abe, T., Park, J., Eubanks, L.M., Sawada, D., Kaufmann, G.F., and Janda, K.D. (2009) Revisiting AI-2 quorum sensing inhibitors: direct comparison of alkyl-DPD analogues and a natural product fimbrolide. J Am Chem Soc 131: 15584-15585.
14. March, J.C., and Bentley, D.E. (2004) Quorum sensing and bacterial talk in biotechnology. Curr Opin Biotechnol 15: 495-502.
15. Martinelli, D., Grossmann, G., Sequin, U., Brandl, H., and Bachofen, R. (2004) Effects of natural and chemically synthesized furanones on quorum sensing in Chromobacterium violaceum. BMC Microbiol 4: 25-35.
16. Müh, U., Schuster, M., Heim, R., Singh, A., Olson, E.R., and Greenberg, E.P. (2006) Novel Pseudomonas aeruginosa quorum-sensing inhibitors identified in an ultra-highthroughput screen. Antimicrob Agents Chemother 50: 3674-3679.
17. Nagle, D.G., Camacho, F.T., and Paul, V.J. (1998) Dietary preferences of opistobranch mollusc Stylocheilus longicauda for secondary metabolites produced by the tropical cyanobacterium Lyngbya majuscula. Mar Biol 132: 267- 273.
18. Pearson, J.P., Pesci, E.C., and Iglewski, B.H. (1997) Roles of Pseudomonas aeruginosa las and rhl quorum sensing systems in control of elastase and rhamnolipid biosynthesis genes. J Bacteriol 179: 5756-5767.
19. Rajamani, S., Bauer, W.D., Robinson, J.B., Farrow, I.J.M., Pesci, E.C., Teplitski, M., et al. (2008) The vitamin riboflavin and its derivative lumichrome activate the LasR bacterial quorum-sensing receptor. Mol Plant Microbe Interact 21: 1184-1192.
20. Rampioni, G., Bertani, I., Zennaro, E., Polticelli, F., Venturi, V., and Leoni, L. (2006) The quorum-sensing negative regulator RsaL of Pseudomonas aeruginosa binds to the lasI promoter. J Bacteriol 188: 815-819.
21. Rasmussen, T.B., and Givskov, M. (2006a) Quorum sensing inhibitors: a bargain of effects. Microbiology 152: 895-904.
22. Rasmussen, T.B., and Givskov, M. (2006b) Quorum-sensing inhibitors as anti-pathogenic drugs. Int J Med Microbiol 296: 149-161.
23. Ren, D.C., Sims, J.J., and Wood, T.K. (2001) Inhibition of biofilm formation and swarming of Escherichia coli by (5Z)-4-bromo-5(bromomethylene)-3-butyl-2(5H)-furanone. Environ Microbiol 3: 731-736.
24. Romero, M., Diggle, S.P., Heeb, S., Cámara, M., and Otero, A. (2008) Quorum quenching activity in Anabaena sp. PCC 7120: identification of AiiC, a novel AHL-acylase. FEMS Microbiol Lett 280: 73-80.
25. Skindersoe, M.E., Ettinger-Epstein, P., Rasmussen, T.B., Bjarnsholt, T., De Nys, R., and Givskov, M. (2008a) Quorum sensing antagonism from marine organisms. Mar Biotechnol 10: 56-63.
26. Skindersoe, M.E., Alhede, M., Phipps, R., Yang, L., Jensen, P.O., Rasmussen, T.B., et al. (2008b) Effects of antibiotics on quorum sensing in Pseudomonas aeruginosa. Antimicrob Agents Chemother 52: 3648-3663.
27. Steinberg, P.D., and De Nys, R. (2002) Chemical mediation of colonization of seaweed surfaces. J Phycol 38: 621-629.
28. Thacker, R.W., Nagle, D.G., and Paul, V.J. (1997) Effect of repeated exposures to marine cyanobacterial secondary metabolites on feeding by juvenile rabbitfish and parrotfish. Mar Ecol Prog Ser 147: 21-29.
29. Waters, C.M., and Bassler, B.L. (2005) Quorum sensing: cell-to-cell communication in bacteria. Annu Rev Cell Dev Biol 21: 319-346.
30. Williams, P. (2007) Quorum sensing, communication and cross-kingdom signalling in the bacterial world. Microbiology 13: 3923-3938.
31. Williams, P., and Camara, M. (2009) Quorum sensing and environmental adaptation in Pseudomonas aeruginosa: a tale of regulatory networks and multifunctional signal molecules. Curr Opin Microbiol 12: 182-191.
32. Winson, M.K., Swift, S., Fish, L., Throup, J.P., Jørgensen, F., Chhabra, S.R., et al. (1998) Construction and analysis of luxCDABE-based plasmid sensors for investigating N-acyl homoserine lactone-mediated quorum sensing. FEMS Microbiol Lett 163: 185-192.
33. Zhang, L.H., and Dong, Y.H. (2004) Quorum sensing and signal interference: diverse implications. Mol Microbiol 53: 1563-1571.