All Title Author
Keywords Abstract


Piericidins, Novel Quorum-Sensing Inhibitors against Chromobacterium violaceum CV026, from Streptomyces sp. TOHO-Y209 and TOHO-O348

DOI: 10.4236/ojmc.2013.34012, PP. 93-99

Keywords: Piericidin A1, 3’-Rhamnopiericidin A1, Piericidin E, Quorum-Sensing Inhibitor, Chromobacterium violaceum CV026, N-Acylhomoserinlactone

Full-Text   Cite this paper   Add to My Lib

Abstract:

Piericidin A1, 3’-rhamnopiericidin A1, and a novel compound piericidin E, a new quorum-sensing (QS) inhibitor
against Chromobacterium violaceum CV026, were isolated from the culture broth of Streptomyces sp. QS is well
known as a microbial signaling system and controls certain types of gene expression resulting in bioluminescence,
biofilm formation, swarming motility, antibiotic biosynthesis, and virulence factor production. C. violaceum CV026 is
commonly used to determine qualitative and quantitative QS activity. The structures of piericidin derivatives were characterized,
and their QS activities were determined.

References

[1]  K. H. Nealson, “Autoinduction of Bacterial Luciferase. Occurrence, Mechanism and Significance,” Archives of Microbiology, Vol. 112, No. 1, 1977, pp. 73-79. http://dx.doi.org/10.1007/BF00446657
[2]  B. L. Bassler and R. Losick, “Bacterially Speaking,” Cell, Vol. 125, No. 2, 2006, pp. 237-246. http://dx.doi.org/10.1016/j.cell.2006.04.001
[3]  R. J. C. McLean, M. Whiteley, D. J. Stickler and W. C. Fuqua, “Evidence of Autoinducer Activity in Naturally Occurring Biofilms,” FEMS Microbiology Letters, Vol. 154, No. 2, 1997, pp. 259-263. http://dx.doi.org/10.1111/j.1574-6968.1997.tb12653.x
[4]  L. Eberl, M. K. Winson, C. Sternberg, G. S. Stewart, G. Christiansen, S. R. Chhabra, B. Bycroft, P. Williams, S. Molin and M. Givskov, “Involvement of N-acyl-L-homoserine Lactone Autoinducers in Controlling the Multi-cellular Behaviour of Serratialiquefaciens,” Molecular Microbiology, Vol. 20, No. 1, 1996, pp. 127-136. http://dx.doi.org/10.1111/j.1365-2958.1996.tb02495.x
[5]  H. Slater, M. Crow, L. Everson and G. P. Salmond, “Phosphate Availability Regulates Biosynthesis of Two Antibiotics, Prodigiosin and Carbapenem, in Serratia via both Quorum-Sensing-Dependent and -Independent Pathways,” Molecular Microbiology, Vol. 47, No. 2, 2003, pp. 303-320. http://dx.doi.org/10.1046/j.1365-2958.2003.03295.x
[6]  P. C. Fineran, H. Slater, L. Everson, K. Hughes and G. P. Salmond, “Biosynthesis of Tripyrrole and Beta-Lactam Secondary Metabolites in Serratia: Integration of Quorum Sensing with Multiple New Regulatory Components in the Control of Prodigiosin and Carbapenem Antibiotic Production,” Molecular Microbiology, Vol. 56, No. 6, 2005, pp. 1495-1517. http://dx.doi.org/10.1111/j.1365-2958.2005.04660.x
[7]  J. P. Falcao, F. Sharp and S. V. perandio, “Cell-to-Cell Signaling in Intestinal Pathogens,” Current Issues in Intestinal Microbiology, Vol. 5, No. 1, 2004, pp. 9-17.
[8]  L. C. Antunes, R. B. Ferreira, M. M. Buckner and B. B. Finlay, “Quorum Sensing in Bacterial Virulence,” Microbiology, Vol. 156, No. 8, 2010, pp. 2271-2282. http://dx.doi.org/10.1099/mic.0.038794-0
[9]  A. Baldwin, P. A. Sokol, J. Parkhill and E. Maherthiralingam, “The Burkholderiacepacia Epidemic Strain Marker Is Part of a Novel Genomic Island Encoding both Virulence and Metabolism-Associated Genes in Burkholderi- acenocepacia,” Infection and Immunity, Vol. 72, No. 3, 2004, pp. 1537-1547. http://dx.doi.org/10.1128/IAI.72.3.1537-1547.2004
[10]  E. Valade, F. M Thibault, Y. P. Gauthier, M. Palencia, Y. Popoff and D. R. Vidal, “The PmlI-PmlR Quorum-Sensing System in Burkholderiapseudomallei Plays a Key Role in Virulence and Modulates Production of the MprA Protease,” Journal of Bacteriology, Vol. 186, No. 8, 2004, pp. 2288-2294. http://dx.doi.org/10.1128/JB.186.8.2288-2294.2004
[11]  N. Towako, M. Hiroshi, K. Junichi, H. Tomayoshi, F. Takeshi, K. Misuzu, S. Ryo, Y. Katsunori, T. Kazunori, K. Takehiko and K. Shigeru, “Effect of Erythromycin on Chronic Respiratory Infection Caused by Pseudomonas aeruginosa with Biofilm Formation in an Experimental Murine Model,” Antimicrobial Agents and Chemotherapy, Vol. 48, No. 6, 2004, pp. 2251-2259. http://dx.doi.org/10.1128/AAC.48.6.2251-2259.2004
[12]  D. Martinelli, G. Grossmann, U. Séquin, H. Brandl and R. Bachofen, “Effects of Natural and Chemically Synthesized Furanones on Quorum Sensing in Chromobacteriumviolaceum,” BMC Microbiology, Vol. 4, 2004, p. 25. http://dx.doi.org/10.1186/1471-2180-4-25
[13]  K. H. McClean, M. K. Winson, L. Fish, A. Taylor, S. R. Chhabra, M. Camara, M. Daykin, J. H. Lamb, et al., “Quorum Sensing and Chromobacteriumviolaceum: Exploitation of Violacein Production and Inhibition for the Detection of N-Acylhomoserine Lactones,” Microbiology, Vol. 143, No. 12, 1997, pp. 3703-3711. http://dx.doi.org/10.1099/00221287-143-12-3703
[14]  E. B. Shiring and D. Gottlieb, “Methods for Characterization of Streptomyces Species,” International Journal of Systematic Bacteriology, Vol. 16, No. 3, 1966, pp. 313- 340. http://dx.doi.org/10.1099/00207713-16-3-313
[15]  S. A. Waksman, “Classification, Identification and Description of Genera and Specie,” Williams and Wilkins Co., Baltimore, 1961.
[16]  “Color Harmony Manual,” 4th Edition, Container Corporation of America, Chicago, 1958.
[17]  T. G. Pridham and D. Gottlieb, “The Utilization of Carbon Compounds by Some Actinomycetales as an Aid for Species Determination,” Journal of Bacteriology, Vol. 56, No. 1, 1948, pp. 107-114.
[18]  B. Becker, M. P. Lechevalier and H. A. Lechevalier, “Chemical Composition of Cell-Wall Preparation from Strains of Various Form-Genera of Aerobic Actinomycetes,” Applied Microbiology and Biotechnology, Vol. 13, 1965, pp. 236-243.
[19]  M. Okamoto, K. Yoshida, M. Nishikawa, T. Ando, M. Iwami, M. Kohsaka and H. Aoki, “FR-900452, a Specific Antagonist of Platelet Activating Factor (PAF) Produced by Streptomyces phaeofaciens. I. Taxonomy, Fermentation, Isolation, and Physic-Chemical and Biological Characteristics,” The Journal of Antibiotics, Vol. 39, No. 2, 1986, pp. 198-204. doi: 0.7164/antibiotics.39.198
[20]  M. Iwami, S. Kiyoto, H. Terano, M. Kohsaka, H. Aoki and H. Imanaka, “A New Antitumore Antibiotic, FR- 900482. I. Taxonomic Studies on the Producing Strain: A New Species of the Genus Streptomyces,” The Journal of Antibiotics, Vol. 40, No. 5, 1987, pp. 589-593.
[21]  M. Jeng, C. Hall, F. L. Crane, N. Takahashi, S. Tamura and K. Folkers, “Inhibition of Mitochondrial Electron Transport by Piericidin A and Related Compounds,” Bio- chemistry, Vol. 7, No. 4, 1968, pp. 1311-1322. http://dx.doi.org/10.1021/bi00844a010
[22]  A. Urakawa, T. Sasaki, K. Yoshida, T. Otani, Y. Lei and W. Yun, “IT-143-A and B, Novel Piericidin-Group Antibiotics Produced by Streptomyces sp.,” The Journal of Antibiotics, Vol. 49, No. 10, 1996, pp. 1052-1055. http://dx.doi.org/10.7164/antibiotics.49.1052
[23]  K. Kimura, S. Nakayama, N. Nakajima, M. Yoshihama, N. Miyata and G. Kawanishi, “A New Piericidinrham-noside, 3’-Rhamnopiericidin A1,” The Journal of Antibiotics, Vol. 43, No. 10, 1990, pp. 1341-1343. http://dx.doi.org/10.7164/antibiotics.43.1341
[24]  K. A. Shaaban, E. Helmke, G. Kelter, H. H. Fiebig and H. Laatsch, “Glicopiericidin C: A Cytotoxic Piericidinglucoside Antibiotic Produced by a Marine Strepromyces Isolate,” The Journal of Antibiotics, Vol. 64, No. 2, 2011, pp. 205-209. http://dx.doi.org/10.1038%2Fja.2010.125
[25]  K. Kimura, H. Takahashi, N. Miyata, M. Yoshihama and M. Uramoto, “New Piericidin Antibiotics, 7-Demethyl- piericidin A1,” The Journal of Antibiotics, Vol. 49, No. 7, 1996, pp. 697-699. http://dx.doi.org/10.7164/antibiotics.49.697
[26]  Y. Hayakawa, S. Shirasaki, S. Shiba, T. Kawasaki, Y. Matsuo, K. Adachi and Y. Shizuri, “Piericidin C7 and C8, New Cytotoxic Antibiotics Produced by a Merine Streptomyces sp.,” The Journal of Antibiotics, Vol. 60, No. 3, 2007, pp. 196-200. http://dx.doi.org/10.1038/ja.2007.22
[27]  J. Ueda, T. Togashi, S. Matukura, A. Nagai, T. Nakashima, H. Komaki, K. Anzai, S. Harayama, T. Doi, T. Takahashi, T. Natsume, Y. Kisu, N. Goshima, N. Nomura, M. Takagi and K. Shin-Ya, “A Novel Nuclear Export Inhibitor JBIR-02, a New Piericidin Discovered from Streptomyces sp. ML55,” The Journal of Antibiotics, Vol. 60, No. 7, 2007, pp. 459-462. http://dx.doi.org/10.1038/ja.2007.59

Full-Text

comments powered by Disqus