Cyclic dipeptides from lactic acid bacteria inhibit proliferation of the influenza a virus

Journal of Microbiology

Volumn 51, Issue 6, 2013, Pages 836-843

  Kwak, Min Kyu ^a   Liu, Rui ^a   Kwon, Jun Oh ^a   Kim, Min Kyu ^a,b   Kim, Andrew HyoungJin ^a   Kang, Sa Ouk ^a  

^a Seoul National University   (South Korea)

^b Korea Research Institute of Ships and Ocean Engineering   (South Korea)

Author keywords

antiviral activity; cis cyclo(l Leu l Pro); cis cyclo(l Phe l Pro); culture filtrate; influenza A virus; Lactobacillus plantarum LBP K10

Indexed keywords

ANTIVIRUS AGENT; DIPEPTIDE; LACTIC ACID;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECT; GROWTH, DEVELOPMENT AND AGING; INFLUENZA VIRUS A H3N2; LACTOBACILLUS; LACTOBACILLUS PLANTARUM; METABOLISM;

ANTIVIRAL AGENTS; DIPEPTIDES; INFLUENZA A VIRUS, H3N2 SUBTYPE; LACTIC ACID; LACTOBACILLUS; LACTOBACILLUS PLANTARUM; MOLECULAR STRUCTURE;

EID: 84891614350     PISSN: 12258873     EISSN: 19763794     Source Type: Journal    
DOI: 10.1007/s12275-013-3521-y     Document Type: Article

References (34)

1. Alak, J. I., Wolf, B. W., Mdurvwa, E. G., Pimentel-Smith, G. E., and Adeyemo, O. 1997. Effect of Lactobacillus reuteri on intestinal resistance of Cryptosporidium parvum infection in a murine model of acquired immuno-deficiency syndrome. J. Infect. Dis. 175, 218-221.
2. Borthwick, A. D. 2012. 2, 5-Diketopiperazines: synthesis, reactions, medicinal chemistry, and bioactive natural products. Chem. Rev. 112, 3641-3716.
3. De Man, J. C., Rogosa, M., and Sharpe, M. E. 1960. A medium for the cultivation of Lactobacilli. J. Appl. Microbiol. 23, 130-135.
4. Digaitiene, A., Hansen, Josephsen, J. 2012. Lactic acid bacteria isolated from rye sourdoughs produce bacteriocin-like inhibitory substances active against Bacillus subtilis and fungi. J. Appl. Microbiol. 112, 732-742.
5. Ducluzeau, R., Dubos, F., and Raibaud, P. 1971. Antagonist effect of a Lactobacillus strain on a Ristella sp. strain in the digestive tract of gnotoxenic mice ingesting lactose. Ann. Inst. Pasteur. (Paris)121, 777-794.
6. Gänzle, M. G., Höltzel, A., Walter, J., Jung, G., and Hammes, W. P. 2000. Characterization of reutericyclin produced by Lactobacillus reuteri LTH2584. Appl. Environ. Microbiol. 66, 4325-4333.
7. Gao, Q., Liu, F., Zhang, T., Zhang, J., Jia, S., Yu, C., Jiang, K., and Gao, N. 2010. The role of lactic acid adsorption by ion exchange chromatography. PLoS One5, e13948.
8. Graz, M., Hunt, A., Jamie, H., Grant, G., and Milne, P. 1999. Antimicrobial activity of selected cyclic dipeptides. Pharmazie54, 772-775.
9. Huprikar, J. and Rabinowitz, S. 1980. A simplified plaque assay for influenza viruses in Madin-Darby kidney (MDCK) cells. J. Virol. Methods1, 117-120.
10. Jefferies, W. M., Turner, J. C., Lobo, M., and Gwaltney, J. M. Jr. 1998. Low plasma levels of adrenocorticotropic hormone in patients with acute influenza. Clin. Infect. Dis. 26, 708-710.
11. Kanzaki, H., Imura, D., Nitoda, T., and Kawazu, K. 2000. Enzymatic conversion of cyclic dipeptides to dehydro derivatives that inhibit cell division. J. Biosci. Bioeng. 90, 86-89.
12. Lee, K. H., Kim, K. W., and Rhee, K. H. 2010. Identification of Streptomyces sp. KH29, which produces an antibiotic substance processing an inhibitory activity against multidrug-resistant Acinetobacter baumannii. J. Microbiol. Biotechnol. 20, 1672-1676.
13. Li, H., Liu, L., Zhang, S., Cui, W., and Lv, J. 2012. Identification of antifungal compounds produced by Lactobacillus casei AST18. Curr. Microbiol. 65, 156-161.
14. Li, J., Wang, W., Xu, S. X., Magarvey, N. A., and McCormick, J. K. 2011. Lactobacillus reuteri-produced cyclic dipeptides quench agr-mediated expression of toxic shock syndrome toxin-1 in staphylococci. Proc. Natl. Acad. Sci. USA108, 3360-3365.
15. Li, X., Hopmann, K. H., Hudecová, J., Isaksson, J., Novotná, J., Stensen, W., Andrushchenko, V., Urbanová, M., Svendsen, J. S., Bouř, P., andet al. 2013. Determination of absolute configuration and conformation of a cyclic dipeptide by NMR and chiral spectroscopic methods. J. Phys. Chem. A. 117, 1721-1736.
16. Magnusson, J., Ström, K., Roos, S., Sjögren, J., and Schnürer, J. 2003. Broad and complex antifungal activity among environmental isolates of lactic acid bacteria. FEMS Microbiol. Lett. 219, 129-135.
17. Matsuda, T. 1994. Antimicrobial activities of organic acids determined by minimum inhibitory concentrations at different PH ranged from 4. 0 to 7. 0. Nippon Shokuhin Kogyo Gakkaishi41, 687-702.
18. McCleland, K., Milne, P. J., Lucieto, F. R., Frost, C., Brauns, S. C., van De Venter, M., Du Plessis, J., and Dyason, K. 2004. An investigation into the biological activity of the selected histidine-containing diketopiperazines cyclo(His-Phe) and cyclo(His-Tyr). J. Pharm. Pharmacol. 56, 1143-1153.
19. Mezaini, A., Chihib, N. E., Bouras, A. D., Nedjar-Arroume, N., and Hornez, J. P. 2009. Antibacterial activity of some lactic acid bacteria isolated from an Algerian dairy product. J. Environ. Public Health2009, 1-6.
20. Naidu, A. S., Bidlack, W. R., and Clemens, R. A. 1999. Probiotic spectra of lactic acid bacteria (LAB). Crit. Rev. Food Sci. Nutr. 39, 13-126.
21. Niku-Paavola, M. L., Laitila, A., Mattila-Sandholm, T., and Haikara, A. 1999. New types of antimicrobial compounds produced by Lactobacillus plantarum. J. Appl. Microbiol. 86, 29-35.
22. Prasad, C. 1995. Bioactive cyclic dipeptides. Peptides16, 151-164.
23. Rani, B. and Khetarpaul, N. 1998. Probiotic fermented food mixtures: possible applications in clinical anti-diarrhoea usage. Nutr. Hlth. 12, 97-105.
24. Rhee, K. H. 2004. Cyclic dipeptides exhibit synergistic, broad spectrum antimicrobial effects and have anti-mutagenic properties. Int. J. Antimicrob. Agents24, 423-427.
25. Ross, R. P., Morgan, S., and Hill, C. 2002. Preservation and fermentation: past, present and future. Int. J. Food Microbiol. 79, 3-16.
26. Rouse, S. and van Sinderen, D. 2008. Bioprotective potential of lactic acid bacteria in malting and brewing. J. Food Prot. 71, 1724-1733.
27. Savage, D. C. 1969. Microbial interference between indigenous yeast and lactobacilli in the rodent stomach. J. Bacteriol. 98, 1278-1283.
28. Steinhauer, D. A. 1999. Role of hemagglutinin cleavage for the pathogenicity of influenza virus. Virology258, 1-20.
29. Ström, K., Sjögren, J., Broberg, A., and Schnürer, J. 2002. Lactobacillus plantarum MiLAB 393 produces the antifungal cyclic dipeptides cyclo(l-Phe-l-Pro) and cyclo(l-Phe-trans-4-OH-l-Pro) and 3-phenyllactic acid. Appl. Environ. Microbiol. 68, 4322-4327.
30. Trabocchi, A., Scarpi, D., and Guarna, A. 2008. Structural diversity of bicyclic amino acids. Amino Acids34, 1-24.
31. Tsuruoka, N., Beppu, Y., Koda, H., Doe, N., Watanabe, H., and Abe, K. 2012. A DKP cyclo(L-Phe-L-Phe) found in chicken essence is a dual inhibitor of the serotonin transporter and acetylcholine sterase. PLoS One7, e50824.
32. van der Merwe, E., Huang, D., Peterson, D., Kilian, G., Milne, P. J., van de Venter, M., and Frost, C. 2008. The synthesis and anticancer activity of selected diketopiperazines. Peptides29, 1305-1311.
33. Wagner, R. D., Pierson, C., Warner, T., Dohnalek, M., Farmer, J., Roberts, L., Hilty, M., and Balish, E. 1997. Biotherapeutic effects of probiotic bacteria on candidiasis in immunodeficient mice. Infect. Immun. 65, 4165-4172.
34. Watanabe, W., Konno, K., Ijichi, K., Inoue, H., Yokota, T., and Shigeta, S. 1994. MTT colorimetric assay system for the screening of anti-orthomyxo- and anti-paramyxoviral agents. J. Virol. Methods48, 257-265.