A novel isoquinoline alkaloid, DD-carboxypeptidase inhibitor, with antibacterial activity isolated from Streptomyces sp. 8812. Part I: Taxonomy, fermentation, isolation and biological activities

Journal of Antibiotics

Volumn 62, Issue 10, 2009, Pages 575-580

  Solecka, Jolanta ^a   Rajnisz, Aleksandra ^a   Laudy, Agnieszka E ^b  

^a NATIONAL INSTITUTE OF HYGIENE   (Poland)

^b MEDICAL UNIVERSITY OF WARSAW   (Poland)

Author keywords

Antibacterial agent; DD carboxypeptidase inhibitor; Isoquinoline alkaloid; JS 1

Indexed keywords

ACETONE; BETA LACTAMASE; CARBOXYPEPTIDASE TRANSPEPTIDASE; ISOQUINOLINE ALKALOID; JS 1; PEPTIDE HYDROLASE INHIBITOR; PROTEINASE; UNCLASSIFIED DRUG;

ACINETOBACTER BAUMANNII; ACTINOMADURA; ANION EXCHANGE; ANTIBACTERIAL ACTIVITY; ANTIMICROBIAL ACTIVITY; ARTICLE; BACTERIUM CULTURE; BIOLOGICAL ACTIVITY; BORDETELLA BRONCHISEPTICA; BURKHOLDERIA CEPACIA; CONTROLLED STUDY; DRUG ISOLATION; DRUG PURIFICATION; DRUG STRUCTURE; ENZYME ACTIVITY; ENZYME INHIBITION; FERMENTATION; GENOTOXICITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; PROTEUS MIRABILIS; PROTEUS VULGARIS; SACCHAROPOLYSPORA; STAPHYLOCOCCUS AUREUS; STENOTROPHOMONAS MALTOPHILIA; STREPTOMYCES; STREPTOMYCES ERYTHRAEUS; TAXONOMY; TOXICITY TESTING;

ACTINOMYCETALES; ALKALOIDS; ANTI-BACTERIAL AGENTS; CARBOXYPEPTIDASES; CULTURE MEDIA; FERMENTATION; GRAM-NEGATIVE BACTERIA; GRAM-POSITIVE BACTERIA; ISOQUINOLINES; MICROBIAL SENSITIVITY TESTS; PEPTIDYL TRANSFERASES; SACCHAROPOLYSPORA; STREPTOMYCES;

ACINETOBACTER BAUMANNII; ACTINOMADURA; BORDETELLA BRONCHISEPTICA; BURKHOLDERIA CEPACIA; NEGIBACTERIA; POSIBACTERIA; PROTEUS VULGARIS; SACCHAROPOLYSPORA ERYTHRAEA; STAPHYLOCOCCUS AUREUS; STENOTROPHOMONAS MALTOPHILIA; STREPTOMYCES SP.;

EID: 70449127500     PISSN: 00218820     EISSN: None     Source Type: Journal    
DOI: 10.1038/ja.2009.85     Document Type: Article

References (40)

1. Walsh, C. T. Antibiotics: Actions, Origin, Resistance (ASM Press, Washington, DC, 2003).
2. Baker, D. D., Chu, M., Oza, U. & Rajgarhia, V. The value of natural products to future pharmaceutical discovery. Nat. Prod. Rep. 24, 1225-1244 (2007).
3. Imanaka, H. Screening microbial products for medicine. Actinomycetologica 14, 22-26 (2001).
4. Singh, M. P. & Greenstein, M. Antibacterial leads from microbial natural products discovery. Curr. Opin. Drug Disc. Develop. 3, 167-176 (2000).
5. Berdy, J. Bioactive microbial metabolites. J. Antibiot. 58, 1-26 (2005).
6. Waxman, D. J. & Strominger, J. L. Penicillin-binding proteins and the mechanism of action of b-lactam antibiotics. Ann. Rev. Biochem. 52, 825-969 (1983).
7. Ghuysen, J.-M. Bacterial active-site serine penicillin-interactive proteins and domains: mechanism, structure, and evolution. Rev. Infect. Dis. 10, 726-732 (1988).
8. Kurzatkowski, W., Solecka, J., Filipek, J., Kurzatkowski, J. D. & Kurylowicz, W. Streptomycetes excreting DD-carboxypeptidases. Appl. Microbiol. Biotechnol. 33, 452-454 (1990).
9. Solecka, J. & Kurzatkowski, W. Affinity of exocellular DD-carboxypeptidase/transpeptidase from Saccharopolyspora erythraea PZH 64-575 to beta-lactam compounds. Med. Dosw. Mikrobiol. 51, 151-165 (1999).
10. Solecka, J. & Kozerski, L. A new inhibitor of DD-peptidase and its use as antibiotic or anticancer drug. PCT/WO 2009/028972 A1, 5 March (2009).
11. Solecka, J. et al. A novel isoquinoline alkaloid, DD-carboxypeptidase inhibitor, with antimicrobial activity isolated from Streptomyces sp. 8812. Part II: Physico-chemical properties and structure elucidation. J. Antibiot. (e-pub ahead of print 28 August 2009; doi:10.1038/ja.2009.86).
12. Dusart, J. et al. DD-Carboxypeptidase-transpeptidase and killing site of b-lactam antibiotics in Streptomyces strains R39, R61, and K11. Antimicrob. Ag. Chemother. 3, 181-187 (1973).
13. Gould, I. M. The epidemiology of antibiotic resistance. Int. J Antimicrob. Agents 32S, S2-S9 (2008).
14. Casey, A. L., Lambert, P. A. & Elliott, T. S. J. Staphylococci. Int. J Antimicrob. Agents 29 (Suppl. 3), S23-S32 (2007).
15. Denton, M. Enterobacteriaceae. Int. J Antimicrob. Agents 29(Suppl. 3), S9-S22 (2007).
16. Scazzocchio, F., Cometa, M. F., Tomassini, L. & Palmery, M. Antibacterial activity of Hydrastis canadensis extract and its major isolated alkaloids. Planta Med. 67, 561-564 (2001).
17. Feng, T., Xu, Y., Cai, X.-H., Du, Z.-Z. & Luo, X.-D. Antimicrobially active isoquinoline alkaloids from Litsea cubeba. Planta Med. 75, 76-79 (2009).
18. Iwasa, K. et al. Simple isoquinoline and benzylisoquinoline alkaloids as potential antimicrobial, antimalarial, cytotoxic, and anti-HIV agents. Bioorg. Med. Chem. 9, 2871-2884 (2001).
19. Prauser, H. Aptness and application of colour codes for exact description of colours of streptomycetes. Z. Allg. Mikrobiologie 4, 95-98 (1964).
20. Williams, S. T., Goodfellow, M. & Alderson, G. Genus Streptomyces Waksman and Henrici 1943. in Bergey's Manual of Systematic Bacteriology, Vol.4 (ed. Williams, S. T.) 2452-2492 (Williams & Wilkins, Baltimore, 1989).
21. Shirling, E. B. & Gottlieb, D. Methods for characterization of Streptomyces species. Int. J. Syst. Bacteriol. 16, 313-340 (1966).
22. Frere, J. M., Leyh-Bouille, M., Ghuysen, J. M., Nieto, M. & Perkins, H. R. Exocellular DD-carboxypeptidases/transpeptidases from Streptomyces. Methods Enzymol. 45, 610-636 (1976).
23. Solecka, J., &Pysek, R., Furman, B., Chmielewski, M. & Kurzatkowski, W. Practical use of DD-peptidase 64-575 for assay inhibition activity of natural and synthetic b-lactam compounds. Acta. Poloniae Pharmaceutica 60, 115-118 (2003).
24. Frere, J.-M. et al. Molecular weight, amino acid composition and physicochemical properties of the exocellular DD-carboxypeptidase-transpeptidase of Streptomyces R39. Biochem. J. 143, 233-240 (1974).
25. Sternesjo, A. & Gustavsson, E. Biosensor analysis of [beta]-lactams I milk using the carboxypeptidase activity of a bacterial penicillin binding protein. J. AOAC Int. 89, 832-837 (2006).
26. Bieth, J., Spiess, B. & Wermuth, C. G. Synthesis and analytical use of highly sensitive an convenient substrate of elastase. Biochem. Medicine 11, 350-357 (1974).
27. Hass, G. M. & Ryan, C. A. Carboxypeptidase inhibitor from potatoes. Methods Enzymol. 80, 778-791 (1981).
28. Bezeaud, A. & Guillin, M.-C. Enzymatic and nonenzymic properties of human b-thrombin. J. Biol. Chem. 263, 3576-3581 (1988).
29. Erlanger, B. F., Edel, F. & Cooper, A. G. The action of chymotrypsin on two new chromogenic substrates. Arch. Biochem. Biophys. 210, 206-210 (1966).
30. Kassell, B. Bovine trypsin-kallikrein inhibitor (kunits inhibitor, basic pancreatic inhibitor, polyvalent inhibitor from bovine organs). Methods Enzymol. 19, 844-852 (1970).
31. Mole, J. & Horton, H. R. Kinetics of papain-catalyzed hydrolysis of a-N-benzoyl- L-arginine-p-nitroanilide. Biochemistry 12, 816-822 (1973).
32. Kakudo, S. et al. Purification, characterization, cloning, and expressin of a glutamic acid-specific protease from Bacillus licheniformis ATCC 14580. J. Biol. Chem. 267, 23782-23788 (1992).
33. Anson, M. L. The estimation of pepsin, trypsin, papain, and cathepsin with hemoglobin. J. Gen. Physiol. 22, 79-89 (1938).
34. O'Callaghan, C. H., Morris, A., Kirby, S.M. & Shingler, A. H. Novel method for detection of b-lactamases by using a chromogenic cephalosporin substrate. Antimicrob. Ag. Chemother. 1, 283-288 (1972).
35. CLSI. Method for Dilution Antimicrobial Susceptibility Test for Bacteria That Grow Aerobically; Approved Standard-Seventh Edition. M7-A7 [ISBN 1-56238-587-9]. CLSI, 940 West Valley Road, Suite 1400, Wayne, Pennsylvania 19087-21898, USA (2006).
36. CLSI. Reference Method for Broth Dilution Antifungal Susceptibility Testing of Yeast; Approved Standard-Second Edition. M27-A2, CLSI, Wayne, PA, USA (2002).
37. Dehghan-Noudeh, G., Housaindokht, M. & Bazzaz, B. S. F. Isolation, characterization, and investigation of surface and hemolytic activites of a lipopeptide biosurfactant produced by Bacillus subtilis ATCC 6633. J. Microbiol. 43, 272-276 (2005).
38. Kada, T., Moriya, M. & Shirasu, Y. Screening of pesticides for DNA interactions by 'recassay' and mutagenesis testing, and frameshift mutagens detected. Mutat. Res. 26, 243-248 (1974).
39. Kada, T., Hirano, K. & Shirasu, Y. Bacillus subtilis rec-assay test. in Chemical Mutagenesis Vol. 6 (eds de Sevres, F. E. & Hollaender, A.) 149 (Plenum Press, New York, 1980).
40. Sadaie, T. & Kada, T. Recombination-deficient mutants of Bacillus subtilis. J. Bacteriol. 125, 489-500 (1976).