Chemical and biological characterization of sclerosin, an antifungal lipopeptide

Canadian Journal of Microbiology

Volumn 58, Issue 8, 2012, Pages 1027-1034

  Berry, Chrystal L ^a   Brassinga, Ann Karen C Brassinga ^a   Donald, Lynda J ^a   Fernando, W G Dilantha ^a   Loewen, Peter C ^a   de Kievit, Teresa R ^a  

^a UNIVERSITY OF MANITOBA   (Canada)

Author keywords

Biocontrol; Ipopeptide; Pseudomonas; Sclerosin; Sclerotinia sclerotiorum

Indexed keywords

ANTIFUNGAL AGENT; CORPEPTIN A; CORPEPTIN B; LIPOPEPTIDE; SCLEROSIN; UNCLASSIFIED DRUG;

ANTIMICROBIAL ACTIVITY; BACTERIUM; BIOACTIVITY; BIOCONTROL AGENT; FUNGUS; GERMINATION; GROWTH RATE; MASS SPECTROMETRY; METABOLITE; NEMATODE; PATHOGENICITY; PEPTIDE;

AMINO ACID SEQUENCE; ANTIBACTERIAL ACTIVITY; ANTIFUNGAL ACTIVITY; ARTICLE; BACILLUS; BACTERIAL GROWTH; BIOLOGICAL ACTIVITY; CAENORHABDITIS ELEGANS; CHEMICAL STRUCTURE; FUNGAL SPORE GERMINATION; NONHUMAN; PHYTOPHTHORA INFESTANS; PRIORITY JOURNAL; PSEUDOMONAS; SCLEROTINIA SCLEROTIORUM; TANDEM MASS SPECTROMETRY;

AMINO ACID SEQUENCE; ANIMALS; ANTI-INFECTIVE AGENTS; ANTIFUNGAL AGENTS; BACILLUS; CAENORHABDITIS ELEGANS; LARVA; LIPOPEPTIDES; MASS SPECTROMETRY; PSEUDOMONAS;

BACILLUS (BACTERIUM); BACTERIA (MICROORGANISMS); CAENORHABDITIS ELEGANS; ESCHERICHIA COLI; PHYTOPHTHORA INFESTANS; PSEUDOMONAS; PSEUDOMONAS SP.; SCLEROTINIA; SCLEROTINIA SCLEROTIORUM;

EID: 84864750966     PISSN: 00084166     EISSN: 14803275     Source Type: Journal    
DOI: 10.1139/W2012-079     Document Type: Article

References (44)

1. Ballio, A., Barra, D., Bossa, F., Collina, A., Grgurina, I., Marino, G., et al. 1991. Syringopeptins, new phytotoxic lipodepsipeptides of Pseudomonas syringae pv. syringae. FEBS Lett. 291(1): 109-112. doi:10.1016/0014-5793(91)81115-O. PMID:1936237.
2. Bender, C.L., Alarcon-Chaidez, F., and Gross, D.C. 1999. Pseudomonas syringae phytotoxins: mode of action, regulation, and biosynthesis by peptide and polyketide synthetases. Microbiol. Mol. Biol. Rev. 63(2): 266-292 PMID:10357851.
3. Berry, C., Fernando, W.G., Loewen, P.C., and de Kievit, T.R. 2010. Lipopeptides are essential for Pseudomonas sp. DF41 biocontrol of Sclerotinia sclerotiorum. Biol. Control, 55(3): 211-218 doi:10. 1016/j.biocontrol.2010.09.011.
4. Berti, A.D., Greve, N.J., Christensen, Q.H., and Thomas, M.G. 2007. Identification of a biosynthetic gene cluster and the six associated lipopeptides involved in swarming motility of Pseudomonas syringae pv. tomato DC3000. J. Bacteriol. 189(17): 6312-6323 doi:10.1128/JB.00725-07. PMID:17601782.
5. Biemann, K. 1990. Appendix 5. Nomenclature for peptide fragment ions (positive ions). Meth. Enzymol. 193: 886-887. doi:10.1016/ 0076-6879(90)93460-3 PMID:2074849.
6. Bjørnlund, L., Rønn, R., Péchy-Tarr, M., Maurhofer, M., Keel, C., and Nybroe, O. 2009. Functional GacS in Pseudomonas DSS73 prevents digestion by Caenorhabditis elegans and protects the nematode from killer flagellates. ISME J. 3(7): 770-779 doi:10. 1038/ismej.2009.28. PMID:19340083.
7. Brenner, S. 1974. The genetics of Caenorhabditis elegans. Genetics, 77(1): 71-94 PMID:4366476.
8. Dalla Serra, M., Fagiuoli, G., Nordera, P., Bernhart, I., Della Volpe, C., Di Giorgio, D., et al. 1999. The interaction of lipodepsipeptide toxins from Pseudomonas syringae pv. syringae with biological and model membranes: a comparison of syringotoxin, syringo- mycin, and two syringopeptins. Mol. Plant-Microbe Interact. 12(5): 391-400. doi:10.1094/MPMI.1999.12.5.391. PMID: 10226372.
9. de Bruijn, I., de Kock, M.J.D., Yang, M., de Waard, P., van Beek, T. A., and Raaijmakers, J.M. 2007. Genome-based discovery, structure prediction and functional analysis of cyclic lipopeptide antibiotics in Pseudomonas species. Mol. Microbiol. 63(2): 417-428 doi:10.1111/j.1365-2958.2006.05525.x. PMID:17241198.
10. de Bruijn, I., de Kock, M.J., de Waard, P., van Beek, T.A., and Raaijmakers, J.M. 2008. Massetolide A biosynthesis in Pseudo- monas fluorescens. J. Bacteriol. 190(8): 2777-2789 doi:10.1128/ JB.01563-07. PMID:17993540.
11. de Souza, J.T., de Boer, M., de Waard, P., Van Beek, T.A., and Raaijmakers, J.M. 2003. Biochemical, genetic, and zoosporicidal properties of cyclic lipopeptide surfactants produced by Pseudo- monas fluorescens. Appl. Environ. Microbiol. 69(12): 7161-7172 doi:10.1128/AEM.69.12.7161-7172.2003 PMID:14660362.
12. Emanuele, M.C., Scaloni, A., Lavermicocca, P., Jacobellis, N.S., Camoni, L., Di Giorgio, D., et al. 1998. Corpeptins, new bioactive lipodepsipeptides from cultures of Pseudomonas corrugata. FEBS Lett. 433(3): 317-320. doi:10.1016/S0014-5793(98)00933-8. PMID:9744818.
13. Finking, R., and Marahiel, M.A. 2004. Biosynthesis of nonribosomal peptides. Annu. Rev. Microbiol. 58(1): 453-488. doi:10.1146/ annurev.micro.58.030603.123615. PMID:15487945
14. Fiore, A., Mannina, L., Sobolev, A.P., Salzano, A.M., Scaloni, A., Grgurina, I., et al. 2008. Bioactive lipopeptides of ice-nucleating snow bacterium Pseudomonas syringae strain 31R1. FEMS Microbiol. Lett. 286(2): 158-165. doi:10.1111/j.1574-6968.2008. 01247.x. PMID:18789127.
15. Forge, T.A., and MacGuidwin, A.E. 1989. Nematode autofluores- cence and its use as an indicator of viability. J. Nematol. 21(3): 399-403 PMID:19287626.
16. Gerard, J., Lloyd, R., Barsby, T., Haden, P., Kelly, M.T., and Andersen, R.J. 1997. Massetolides A-H, antimycobacterial cyclic depsipeptides produced by two pseudomonads isolated from marine habitats. J. Nat. Prod. 60(3): 223-229 doi:10.1021/ np9606456. PMID:9157190.
17. Govers, F., and Latijnhouwers, M. 2004. Late blight. In Encyclopedia of plant and crop science. Marcel Dekker, N.Y., USA. pp. 1-5.
18. Grgurina, I., Bensaci, M., Pocsfalvi, G., Mannina, L., Cruciani, O., Fiore, A., et al. 2005. Novel cyclic lipodepsipeptide from Pseudomonas syringae pv. lachrymans strain 508 and syringo- peptin antimicrobial activities. Antimicrob. Agents Chemother. 49(12): 5037-5045 doi:10.1128/AAC.49.12.5037-5045.2005. PMID:16304170.
19. Grünewald, J., and Marahiel, M.A. 2006. Chemoenzymatic and template-directed synthesis of bioactive macrocyclic peptides. Microbiol. Mol. Biol. Rev. 70(1): 121-146 doi:10.1128/MMBR. 70.1.121-146.2006. PMID:16524919.
20. Hope, I.A. 1999. C. elegans: a practical approach. Edited by B.D. Hames. Oxford University Press, Oxford.
21. Hutchison, M.L., and Gross, D.C. 1997. Lipopeptide phytotoxins produced by Pseudomonas syringae pv. syringae: comparison of the biosurfactant and ion channel-forming activities of syringo- peptin and syringomycin. Mol. Plant-Microb. Interact. 10: 347-354 doi:10.1094/MPMI.1997.10.3.347. PMID:9100379.
22. Jousset, A., Rochat, L., Scheu, S., Bonkowski, M., and Keel, C. 2010. Predator-prey chemical warfare determines the expression of biocontrol genes by rhizosphere-associated Pseudomonas fluor- escens. Appl. Environ. Microbiol. 76(15): 5263-5268. doi:10. 1128/AEM.02941-09. PMID:20525866.
23. Kozlovski, V.I., Donald, L.J., Montero-Collado, V., Loboda, A.V., Chernushevich, I.V., Ens, W., and Standing, K.G. 2005. TOF Mass spectrometer with ESI source, orthogonal injection, and 16 kV acceleration voltage, for study of noncovalent complexes. In Proceedings of the 53rd ASMS Conference Mass Spectrometry and Allied Topics, San Antonio, Texas.
24. Kuiper, I., Lagendijk, E.L., Pickford, R., Derrick, J.P., Lamers, G.E., Thomas-Oates, J.E., et al. 2004. Characterization of two Pseudomonas putida lipopeptide biosurfactants, putisolvin I and II, which inhibit biofilm formation and break down existing biofilms. Mol. Microbiol. 51(1): 97-113 doi:10.1046/j.1365-2958.2003.03751.x. PMID:14651614.
25. Lavermicocca, P., Iacobellis, N.S., Simmaco, M., and Graniti, A. 1997. Biological properties and spectrum of activity of Pseudomonas syringae pv. syringae toxins. Physiol. Mol. Plant Pathol. 50(2): 129-140. doi:10.1006/pmpp.1996.0078.
26. Loboda, A.V., Krutchinsky, A.N., Bromirski, M., Ens, W., and Standing, K.G. 2000. A tandem quadrupole/time-of-flight mass spectrometer with a matrix-assisted laser desorption/ionization source: design and performance. Rapid Commun. Mass Spectrom. 14(12): 1047-1057 doi:10.1002/1097-0231(20000630) 14:12<1047::AID-RCM990>3.0.CO;2-E. PMID:10861986.
27. Loper, J.E., and Lindow, S.E. 1987. Lack of evidence for in situ fluorescent pigment production by Pseudomonas syringae pv. syringae on bean leaf surfaces. Phytopathology, 77(10): 1449-1454 doi:10.1094/Phyto-77-1449.
28. Marahiel, M.A. 1997. Protein templates for the biosynthesis of peptide antibiotics. Chem. Biol. 4(8):561-567
29. Mazzola, M., de Bruijn, I., Cohen, M.F., and Raaijmakers, J.M. 2009. Protozoan-induced regulation of cyclic lipopeptide biosynthesis is an effective predation defense mechanism for Pseudomonas fluorescens. Appl. Environ. Microbiol. 75(21): 6804-6811 doi:10.1128/AEM.01272-09. PMID:19717630.
30. Mott, K.A., and Takemoto, J.Y. 1989. Syringomycin, a bacterial phytotoxin, closes stomata. Plant Physiol. 90(4): 1435-1439. doi:10.1104/pp.90.4.1435. PMID:16666948.
31. Nielsen, T.H., Sorensen, D., Tobiasen, C., Andersen, J.B., Christo- phersen, C., Givskov, M., and Sorensen, J. 2002. Antibiotic and biosurfactant properties of cyclic lipopeptides produced by fluorescent Pseudomonas spp. from the sugar beet rhizosphere. Appl. Environ. Microbiol. 68(7): 3416-3423 doi:10.1128/AEM. 68.7.3416-3423.2002. PMID:12089023.
32. Nutkins, J.C., Mortishire-Smith, R.J., Packman, L.C., Brodey, C.L., Rainey, P.B., Johnstone, K., and Williams, D.H. 1991. Structure determination of tolaasin, an extracellular lipodepsipeptide produced by the mushroom pathogen, Pseudomonas tolaasii Paine. J. Am. Chem. Soc. 113(7): 2621-2627 doi:10.1021/ ja00007a040.
33. Purdy, L.H. 1979. Sclerotinia sclerotiorum: history, diseases and symptomatology, host range, geographic distribution, and impact. Phytopathology, 69(8): 875-880 doi:10.1094/Phyto-69-875.
34. Raaijmakers, J.M., de Bruijn, I., and de Kock, M.J. 2006. Cyclic lipopeptide production by plant-associated Pseudomonas spp.: diversity, activity, biosynthesis, and regulation. Mol. Plant- Microbe Interact. 19(7): 699-710. doi:10.1094/MPMI-19-0699. PMID:16838783.
35. Raaijmakers, J.M., de Bruijn, I., Nybroe, O., and Ongena, M. 2010. Natural functions of lipopeptides from Bacillus and Pseudomonas: more than surfactants and antibiotics. FEMS Microbiol. Rev. 34(6): 1037-1062. doi:10.1111/j.1574-6976.2010.00221.x. PMID:20412310.
36. Rohwer, F., Fritzemeier, K.H., Scheel, D., and Hahlbrock, K. 1987. Biochemical reactions of different tissues of potato (Solanumtuberosum) to zoospores or elicitors from Phytophthora infestans. Planta, 170(4): 556-561. doi:10.1007/BF00402991.
37. Savchuk, S., and Fernando, W.G.D. 2004. Effect of timing of application and population dynamics on the degree of biological control of Sclerotinia sclerotiorum by bacterial antagonists. FEMS Microbiol. Ecol. 49(3): 379-388. doi:10.1016/j.femsec.2004.04. 014. PMID:19712288.
38. Shaner, N.C., Campbell, R.E., Steinbach, P.A., Giepmans, B.N., Palmer, A.E., and Tsien, R.Y. 2004. Improved monomeric red, orange and yellow fluorescent proteins derived from Discosoma sp. red fluorescent protein. Nat. Biotechnol. 22(12): 1567-1572 doi:10.1038/nbt1037. PMID:15558047.
39. Shevchenko, A., Loboda, A., Shevchenko, A., Ens, W., Standing, K. G., Ens, W., and Standing, K.G. 2000. MALDI quadrupole time- of-flight mass spectrometry: a powerful tool for proteomic research. Anal. Chem.72(9):2132-2141. doi:10.1021/ ac9913659. PMID:10815976.
40. van de Mortel, J.E., Tran, H., Govers, F., and Raaijmakers, J.M. 2009. Cellular responses of the late blight pathogen Phytophthora infestans to cyclic lipopeptide surfactants and their dependence on G proteins. Appl. Environ. Microbiol. 75(15): 4950-4957 doi:10. 1128/AEM.00241-09. PMID:19502443.
41. West, S.E., Schweizer, H.P., Dall, C., Sample, A.K., and Runyen- Janecky, L.J. 1994. Construction of improved Escherichia-Pseudomonas shuttle vectors derived from pUC18/19 and sequence of the region required for their replication in Pseudo- monas aeruginosa. Gene, 148(1): 81-86 doi:10.1016/0378-1119(94)90237-2. PMID:7926843.
42. Yang, S.Z., Wei, D.Z., and Mu, B.Z. 2006. Determination of the amino acid sequence in a cyclic lipopeptide using M.S. with DHT mechanism. J. Biochem. Biophys. Methods, 68(1): 69-74 doi:10. 1016/j.jbbm.2006.03.008. PMID:16650479.
43. Zhang, Y., Fernando, W.G.D., de Kievit, T.R., Berry, C., Daayf, F., and Paulitz, T.C. 2006. Detection of antibiotic-related genes from bacterial biocontrol agents with polymerase chain reaction. Can. J. Microbiol. 52(5): 476-481. doi:10.1139/w05-152. PMID: 16699573.
44. Zhong, H., Marcus, S.L., and Li, L. 2005. Microwave-assisted acid hydrolysis of proteins combined with liquid chromatography MALDI M.S./M.S. for protein identification. J. Am. Soc. Mass Spectrom. 16(4): 471-481. doi:10.1016/j.jasms.2004.12.017. PMID:15792716.