Two 2[5H]-furanones as possible signaling molecules in Lactobacillus helveticus

Applied and Environmental Microbiology

Volumn 72, Issue 9, 2006, Pages 6053-6061

  Ndagijimana, Maurice ^a   Vallicelli, Melania ^a   Cocconcelli, P Sandro ^b   Cappa, Fabrizio ^b   Patrignani, Francesca ^a   Lanciotti, Rosalba ^a   Guerzoni, M Elisabetta ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

^b UNIVERSITÀ CATTOLICA DEL SACRO CUORE   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

BACTERIA; CELLS; EXTRACTION; FATTY ACIDS; GAS CHROMATOGRAPHY; MASS SPECTROMETRY;

AUTOLYSIS; MICROEXTRACTION; OXIDATIVE STRESSES; ZYMOGRAMS;

ESTERS;

5 ETHYL 3 HYDROXY 4 METHYL 2(5H) FURANONE DERIVATIVE; AUTOLYSIN; FURANONE DERIVATIVE; MEDIUM CHAIN FATTY ACID; UNCLASSIFIED DRUG;

BACTERIUM; FATTY ACID; GAS CHROMATOGRAPHY; MASS SPECTROMETRY; ORGANIC COMPOUND;

ARTICLE; AUTOLYSIS; BACTERIUM CULTURE; CHEESE; CHEESE RIPENING; CHEMICAL STRUCTURE; CONTROLLED STUDY; ENZYME RELEASE; GAS CHROMATOGRAPHY; GRAM NEGATIVE BACTERIUM; HEAT STRESS; LACTOBACILLUS HELVETICUS; LACTOCOCCUS LACTIS; MASS SPECTROMETRY; MOLECULAR WEIGHT; NONHUMAN; OXIDATIVE STRESS; POLYACRYLAMIDE GEL ELECTROPHORESIS; SIGNAL TRANSDUCTION; SOLID PHASE MICROEXTRACTION; TECHNOLOGY; ZYMOGRAPHY;

CHEESE; CULTURE MEDIA, CONDITIONED; FOOD MICROBIOLOGY; FURANS; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; HYDROGEN PEROXIDE; LACTOBACILLUS HELVETICUS; MICROSCOPY, ELECTRON, SCANNING; MOLECULAR STRUCTURE; N-ACETYLMURAMOYL-L-ALANINE AMIDASE; SIGNAL TRANSDUCTION;

LACTOBACILLUS HELVETICUS; LACTOCOCCUS LACTIS SUBSP. CREMORIS; NEGIBACTERIA;

EID: 33748773296     PISSN: 00992240     EISSN: None     Source Type: Journal    
DOI: 10.1128/AEM.00363-06     Document Type: Article

References (57)

1. Altermann, E., W. M. Russell, M. A. Azcarate-Peril, R. Barrangou, B. L. Buck, O. McAuliffe, N. Souther, A. Dobson, T. Duong, M. Callanan, S. Lick, A. Hamrick, R. Cano, and T. R. Klaenhammer. 2005. Complete genome sequence of the probiotic lactic acid bacterium Lactobacillus acidophilus NCFM. Proc. Natl. Acad. Sci. USA 102:3906-3912.
2. Bassler, B. L., C. Dammel, S. Schauder, K. Skokat, J. Stein, and M. G. Surette. May 2003. Compounds and methods for regulating bacterial growth and pathogenesis. U.S. patent 6,559,176 B1.
3. Berger-Bachi, B., A. Strassle, J. E. Gustafson, and F. H. Kayser. 1992. Mapping and characterization of multiple chromosomal factors involved in methicillin resistance in Staphylococcus aureus. Antimicrob. Agents Chemother. 36:1367-1373.
4. Bonini, C. C., C. Iavarone, C. Trogolo, and G. A. Poultron. 1980. The fragmentation of isotetronic acids under electron impact. Org. Mass Spectr. 15:516-519.
5. Braun, D., N. Pauli, U. Sequin, and H. Zahner. 1995. New butenolides from the photoconductivity screening of Streptomyces antibioticus. FEMS Microbiol. Lett. 126:37-42.
6. Cibik, R., and M. P. Chapot-Chartier. 2004. Characterisation of autolytic enzymes in Lactobacillus pentosus. Lett. Appl. Microbiol. 38:459-463.
7. Cocconcelli, P. S., M. G. Parisi, L. Senini, and V. Bottazzi. 1997. Use of RAPD and 16S rDNA sequencing for the study of Lactobacillus population dynamics in natural whey culture. Lett. Appl. Microbiol. 25:8-12.
8. Coppola, R., M. Nanni, M. Iorizzo, A. Sorrentino, E. Sorrentino, C. Chaivari, and L. Grazia. 1997. Survey of lactic acid bacteria isolated during advanced stages of the ripening of Parmigiano Reggiano cheese. J. Dairy Res. 64:305-310.
9. DeKeersmaecker, S. C., and J. Vanderleyden. 2003. Constraints on detection of autoinducer-2 (AI-2) signalling molecules using Vibrio harveyi as a reporter. Microbiology 149:1953-1956.
10. DeLisa, M. P., J. J. Valades, and W. E. Bentley. 2001. Mapping stress-induced changes in autoinducer AI-2 production in chemostat-cultivated Escherichia coli K-12. J. Bacteriol. 183:2918-2928.
11. De Nys, P. C., P. D. Steinberg, T. S. Charlton, and V. Christov. February 2004. Antifouling of shellfish and aquaculture apparatus. U.S. patent 6,692,557 B1.
12. Dirix, G., P. Monsieurs, B. Dombrecht, R. Daniels, K. Marchal, J. Vanderleyden, and J. Michiels. 2004. Peptide signal molecules and bacteriocins in gram-positive bacteria: a genome-wide in silica screening for peptides containing a double-glycine leader sequence and their cognate transporters. Peptides 25:1425-1440.
13. Forsyth, M. H., and T. L. Cover. 2000. Intercellular communication in Helicobacter pylori: luxS is essential for the production of an extracellular signaling molecule. Infect. Immun. 68:3193-3199.
14. Francis, G. L., G. O. Regester, H. A. Webb, and F. J. Ballard. 1995. Extraction from cheese whey by cation-exchange chromatography of factors that stimulate the growth of mammalian cells. J. Dairy Sci. 78:1209-1218.
15. Frank, D. C., C. M. Owen, and J. Patterson. 2004. Solid phase microextraction (SPME) combined with gas-chromatography and olfactometry-mass spectrometry for characterization of cheese aroma compounds. Lebensm.-Wiss. Technol. 37:139-154.
16. Grossmann, G., M. Poncioni, M. Bornand, B. Jolivet, M. Neuburger, and U. Sequin. 2003. Bioactive butenolides from Streptomyces antibioticus. TÜ99: absolute configurations and synthesis of analogs. Tetrahedron 59:3237-3251.
17. Guerzoni, M. E., M. Ferruzzi, F. Gardini, and R. Lanciotti. 1999. Combined effects of ethanol, high homogenisation pressure, and temperature on cell fatty acid composition in Saccharomyces cerevisiae. Can. J. Microbiol. 45:805-810.
18. Guerzoni, M. E., R. Lanciotti, and P. S. Cocconcelli. 2001. Alteration in cellular fatty acid composition as a response to salt, acid, oxidative and thermal stresses in Lactobacillus helveticus. Microbiology 147:2255-2264.
19. Hayashida, Y., and J. C. Slaughter. 1997. Biosynthesis of flavour-active furanones by Saccharomyces cerevisiae during fermentation depends on the malt type used in medium preparation. Biotechnol. Lett. 19:429-431.
20. Hayashida, Y., K. Nishimura, and J. C. Slaughter. 1998. Formation mechanism of flavour-active furanones, 4-hydroxy-2,5-dimethyl-3(2H)-furanone (HDMF) and 4-hydroxy-2 (or 5)-ethyl-5 (or 2)-methyl-3(2H)-furanone (HEMF), in mugi-miso, fermented soy beans paste with barley-koji. J. Brew. Soc. Jpn. 93:730-738.
21. Hayashida, Y., M. Hatano, Y. Tamura, M. Kakimoto, K. Nishimura, K. Igoshi, H. Kobayashi, and H. Kuriyama. 2001. 4-Hydroxy-2,5-dimethyl-3(2H)- furanone (HDMF) production in simple media by lactic acid bacterium, Lactococcus lactis subsp. cremoris IFO 3427. J. Biosci. Bioeng. 91:97-99.
22. Hornby, J. M., E. C. Jensen, A. D. Lisec, J. J. Tasto, and B. Jahnke. 2001. Quorum sensing in the dimorphic fungus Candida albicans is mediated by farnesol. Appl. Environ. Microbiol. 67:2982-2992.
23. Joyce, E. A., B. L. Bassler, and A. Wright. 2000. Evidence for a signaling system in Helicobacter pylon: detection of a luxS-encoded autoinducer. J. Bacteriol. 182:3638-3643.
24. Kjelleberg, S., P. D. Steinberg, P. C. De Nys, R. Maximilien, M. Manefield, M. Givskov, and L. Gram. April 2003. Methods for microbial regulation. U.S. patent 6,555,356 B2.
25. Kleerebezem, M., J. Boekhorst, R. van Kranenburg, D. Molenaar, O. P. Kuipers, R. Leer, R. Tarchini, S. A. Peters, H. M. Sandbrink, M. W. Fiers, W. Stiekema, R. M. Lankhorst, P. A. Bran, S. M. Hoffer, M. N. Groot, R. Kerkhoven, M. de Vries, B. Ursing, W. M. de Vos, and R. J. Siezen. 2003. Complete genome sequence of Lactobacillus plantarum WCFS1. Proc. Natl. Acad. Sci. USA 100:1990-1995.
26. Lepeuple, A.-S., E. Van Gemert, and M.-P. Chapot-Chartier. 1998. Analysis of the bacteriolytic enzymes of the autolytic Lactococcus lactis subsp. cremoris strain AM2 by renaturing polyacrylamide gel electrophoresis: identification of a prophage-encoded enzyme. Appl. Environ. Microbiol. 64:4142-4148.
27. Levy, L. M., G. M. Cabrera, J. E. Wright, and A. M. Seldes. 2003. 5H-furan-2-ones from fungal cultures of Aporpium caryae. Phytochemistry 62:239-243.
28. Lewis, K. 2000. Programmed death in bacteria. Microbiol. Mol. Biol. Rev. 64:503-514.
29. Lorenz, M. C., N. S. Cutler, and J. Heitman. 2000. Characterization of alcohol-induced filamentous growth in Saccharomyces cerevisiae. Mol. Biol. Cell 11:183-199.
30. Malott, R. J., and R. Y. C. Lo. 2002. Studies on the production of quorum-sensing signal molecules in Mannheimia haemolytica A1 and other Pasteurellaceae species. FEMS Microbiol. Lett. 206:25-30.
31. Martinelli, D., G. Grossmann, U. Sequin, H. Brandi, and R. Bachofen. 2004. Effects of natural and chemically synthesized furanones on quorum sensing in Chromobacterium violaceum. BMC Microbiol. 4:1-10.
32. Milo, C., and G. A. Reineccius. 1997. Identification and quantification of potent odorants in regular fat and low-fat mild Cheddar cheese. J. Agric. Food Chem. 45:3590-3594.
33. Mullin, W. J., and D. B. Emmons. 1997. Determination of organic acids and sugars in cheese, milk and whey by high performance liquid chromatography. Food Res. Int. 30:147-151.
34. Nunomura, N., M. Sasaki, and T. Yakotsuka. 1980. Shoyu flavor components: acidic fractions and the characteristic flavour component. Agric. Biol. Chem. 44:339-351.
35. Palumbo, E., C. F. Favier, M. Deghorain, P. S. Cocconcelli, C. Grangette, A. Mercenier, E. E. Vaughan, and P. Hols. 2004. Knockout of the alanine racemase gene in Lactobacillus plantarum results in septation defects and cell wall perforation. FEMS Microbiol. Lett. 233:131-138.
36. Paulitz, T., B. Nowak-Thompson, P. Gamard, E. Tsang, and J. Loper. 2000. A novel antifungal furanone from Pseudomonas aureofaciens, a biocontrol agent of fungal plant pathogens. J. Chem. Ecol. 26:1515-1524.
37. Preininger, M., and W. Grosch. 1994. Evaluation of key odorants of the neutral volatiles of Emmental cheese by the calculation of odor activity values. Lebensm.-Wiss. Technol. 27:237-244.
38. Preininger, M., and W. Grosch. 1995. Determination of 4-hydroxy-2,5-dimethyl-3(2H)-furanone in cultures of bacteria. Zeitschrift Lebensm. Unters. Forsch. 201:97-98.
39. Pridmore, R. D., B. Berger, F. Desiere, D. Vilanova, C. Barretto, A. C. Pittet, M. C. Zwahlen, M. Rouvet, E. Altermann, R. Barrangou, B. Mollet, A. Mercenier, T. Klaenhammer, F. Arigoni, and M. A. Schell. 2004. The genome sequence of the probiotic intestinal bacterium Lactobacillus johnsonii NCC 533. Proc. Natl. Acad. Sci. USA 101:2512-2517.
40. Roberts, D., P. Pollien, and C. Milo. 2000. SPME method development for headspace analysis of volatile flavor compounds. J. Agric. Food Chem. 48:2430-2437.
41. Rosenbluh, A., and E. Rosenberg. 1993. Developmental lysis and autocides, p. 213-233. In M. Dworkin and D. Kaiser (ed.), Myxobacteria II. American Society for Microbiology, Washington, D.C.
42. Rychlik, M., R. Warmke, and W. Grosch. 1997. Ripening of emmenthal cheese wrapped in oil and without addition of Lactobacillus casei subsp. casei 3. Analysis of character impact flavour compounds. Food Sci. Technol.-Leb. 30:471-478.
43. Schauder, S., K. Shokat, M. G. Surette, and B. L. Bassler. 2001. The LuxS family of bacterial autoinducers: biosynthesis of a novel quorum sensing signal molecule. Mol. Microbiol. 41:463-476.
44. Schell, M. A., M. Karmirantzou, B. Snel, D. Vilanova, B. Berger, G. Pessi, M. C. Zwahlen, F. Desiere, P. Bork, M. Delley, R. D. Pridmore, and F. Arigoni. 2005. The genome sequence of Bifidobacterium longum reflects its adaptation to the human gastrointestinal tract. Proc. Natl. Acad. Sci. USA 102:9430.
45. Schimmel, T. G., A. D. Coffman, and S. J. Parsons. 1998. Effect of butyrolactone I on the producing fungus Aspergillus terreus. Appl. Environ. Microbiol. 64:3707-3712.
46. Slaughter, J. C. 1999. The naturally occurring furanones: formation and function from pheromone and food. Biol. Rev. Camb. Philos. Soc. 74:259-276.
47. Spector, M. P., C. C. DiRusso, M. J. Pallen, F. G. del Portillo, G. Dougan, and B. B. Finlay. 1999. The medium-/long-chain fatty acyl-CoA dehydrogenase (fadF) gene of Salmonella typhimurium is a phase I starvation-stress response (SSR) locus. Microbiology 145:15-31.
48. Spiteller, G. 2002. Do changes in the cell membrane structure induce the generation of lipid peroxidation products which serve as first signalling molecules in cell to cell communication? Prostagl. Leukot. Essent. Fatty Acids 67:151-162.
49. Sugawara, E. 1991. Identification of 4-hydroxy-2 (or 5)-ethyl-5 (or 2)-methyl-3(2H)-furanone as flavor component in miso. Nippon Shokuhin Gakkaishi 38:491-493.
50. Surette, M. G., M. B. Miller, and B. L. Bassler. 1999. Quorum sensing in Escherichia coli, Salmonella typhimurium and Vibrio harveyi: a new family of genes responsible for autoinducer production. Proc. Natl. Acad. Sci. USA 96:1639-1644.
51. Surette, M. G., and B. L. Bassler. 1999. Regulation of autoinducer production in Salmonella typhimurium. Mol. Microbiol. 31:585-596.
52. Valence, F., and S. Lortal. 1995. Zymogram and preliminary characterization of Lactobacillus helveticus autolysins. Appl. Environ. Microbiol. 61:3391-3399.
53. Wilkinson, M. G., T. P. Guinee, and P. F. Fox. 1994. Factors which may influence the determination of autolysis starter bacteria during cheddar cheese ripening. Int. Dairy J. 4:141-160.
54. Wilkinson, M. G., T. P. Guinee, D. M. O'Collaghan, and P. F. Fox. 1994. Autolysis and proteolysis in different strains of starter bacteria during Cheddar cheese ripening. J. Dairy Res. 61:249-262.
55. Winzer, K., K. R. Hardie, and P. Williams. 2002. Bacteria cell-to-cell communication. Curr. Opin. Microbiol. 5:216-222.
56. Winzer, K., K. R. Hardie, N. Burgess, N. Doherty, D. Kirke, M. T. G. Holden, R. Linforth, K. A. Cornell, A. J. Taylor, P. J. Hill, and P. Williams. 2002. LuxS: its role in central metabolism and in vitro synthesis of 4-hydroxy-5-methyl-3(2H)-furanone. Microbiology 148:909-922.
57. Zabetakis, I., and M. A. Holden. 1995. A study of strawberry flavour biosynthesis, p. 211-216. In P. Etievant and P. Schreier (ed.), Bioflavour 95: analysis-precursor studies-biotechnology. INRA Editions, Paris, France.