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Metabolic products of microorganisms

167. Cyclopaldic acid from Aspergillus duricaulis. 1. Production, isolation and biological properties

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Abstract

In the course of a screening for new metabolites from fungi we isolated a substance with antimicrobial activity from cultures of Aspergillus duricaulis (CBS 481.65) (Tü 679). It was antagonized by putrescine, spermidine, spermine, arginine, citrulline, lysine, ornithine, in higher concentration by asparagine and glutamine too. The effect of ethylenediaminetetraacetate on the susceptibility of Streptomyces viridochromogenes (Tü 57) and Bacillus subtilis ATCC 6051 to this antibiotic has been studied.

The substance was characterized and identified as cyclopaldic acid.

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Abbreviations

MIC:

minimum inhibitory concentration

tlc:

thinlayer chromatography

References

  • Birkinshaw, J. H., Raistrick, H., Ross, D. J., Stickling, C. E.: Studies in the biochemistry of microorganisms. 85. Cyclopolic and cyclopaldic acids, metabolic products of Penicillium cyclopium Westling. Biochem. J. 50, 610–628 (1952)

    Google Scholar 

  • Davis, B. D., Mingioli, E. S.: Mutants of Escherichia coli requiring methionine or vitamine B12. J. Bacteriol. 60, 17–28 (1950)

    Google Scholar 

  • Durley, R. C., MacMillan, J., Simpson, T. J., Glen, A. T., Turner, W. B.: Fungal products. XIII. Xanthomegnin, viomellein, rubrosulphin, and viopurpurin, pigments from Aspergillus sulphureus and Aspergillus melleus. J. Chem. Soc. Perkin Trans. 1, 163–169 (1975)

    Google Scholar 

  • Haque, H., Russel, A. D.: Effect of chelating agents on the susceptibility of some strains of gram-negative bacteria to some antibacterial agents. Antimicrob. Agents Chemother 6, 200–206 (1974)

    Google Scholar 

  • Hirshfield, I. N., Rosenfeld, H. J., Leifer, Z., Maas, W. K.: Isolation and characterization of a mutant of Escherichia coli blocked in the synthesis of putrescine. J. Bacteriol. 101, 725–730 (1970)

    Google Scholar 

  • Holzapfel, C. W.: The isolation and structure of cyclopiazonic acid, a toxic metabolite of Penicillium cyclopium Westling. Tetrahedron 24, 2101–2119 (1968)

    Google Scholar 

  • Leive, L.: A non specific increase in permeability in Escherichia coli produced by EDTA. Proc. Nat. Acad. Sci. (Wash.) 53, 754–750 (1965)

    Google Scholar 

  • Leive, L.: Studies on the permeability change produced in coliform bacteria by ethylenediamine tetraacetate. J. Biol. Chem. 243, 2373–2380 (1968)

    Google Scholar 

  • Luk, K. C., Kobbe, B., Townsend, J. M.: Production of cyclopiazonic acid by Aspergillus flavus Link. Appl. Environ. Microbiol. 33, 211–212 (1977)

    Google Scholar 

  • Ohmono, S., Sugita, M., Abe, M.: Isolation of cyclopiazonic acid, cyclopiazonic acid imine and bissecodehydrocyclopiazonic acid from the cultures of Aspergillus versicolor (Vuill.) Tiraboshi. J. Agr. Chem. Soc. (Japan) 47, 57–63 (1973)

    Google Scholar 

  • Raistrick, H., Rudman, P.: Studies in the biochemistry of micro-organisms. 97. Flavipin, a crystalline metabolite of Aspergillus flavipes (Bainier a. Sartory) Thom a. Church and Aspergillus terreus Thom. Biochem. J. 63, 395–405 (1956)

    Google Scholar 

  • Raper, K. P., Fennell, D. I.: The genus Aspergillus. Baltimore: Williams and Wilkins 1965

    Google Scholar 

  • Russell, A. D.: Ethylenediamine tetraacetic acid. In: Inhibition and destruction of the microbial cell (W. B. Hugo, ed.), pp. 209–224. London-New York: Academic Press 1971

    Google Scholar 

  • Stack, M. E., Eppley, R. M., Dreifuss, P. A., Pohland, A. E.: Isolation and identification of xanthomegnin, viomellein, rubrosulphin, and viopurpurin as metabolites of Penicillium viridicatum. Appl. Environ. Microbiol. 33, 351–355 (1977)

    Google Scholar 

  • Stevens, L., Morrison, M. R.: Studies on the role of polyamines associated with the ribosomes from Bacillus stearothermophilus. Biochem. J. 108, 633–640 (1968)

    Google Scholar 

  • Tabor, C. W., Tabor, H.: 1,4-Diaminobutane (putrescine), spermidine and spermine. Ann. Rev. Biochem. 45, 285–306 (1976)

    Google Scholar 

  • Turner, W. B.: Fungal metabolites London-New York: Academic Press 1971

    Google Scholar 

  • Weaver, R. H., Herbst, E. J.: Metabolism of diamines and polyamines in microorganisms. J. Biol. Chem. 231, 637–646 (1958)

    Google Scholar 

  • Young, D. V., Srinivasan, P. R.: Regulation of macromolecular synthesis by putrescine in a conditional Escherichia coli putrescine auxotroph. J. Bacteriol. 112, 30–39 (1972)

    Google Scholar 

  • Zähner, H.: New antibiotics. Postepy Hig. Med. Dośw. 28, 459–469 (1974)

    Google Scholar 

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Metabolic products of microorganisms. 166. M. Kappner, A. Hasenböhler, H. Zähner: Optimierung der Desferri-Ferricrocinbildung bei Aspergillus viridi-nutans Ducker & Thrower. Arch. Microbiol. 115, 323–331 (1977)

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Brillinger, G.U., Heberle, W., Weber, B. et al. Metabolic products of microorganisms. Arch. Microbiol. 116, 245–252 (1978). https://doi.org/10.1007/BF00417847

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  • DOI: https://doi.org/10.1007/BF00417847

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