1887

Abstract

Production of the volatile metabolite, isobutyraldoxime -methyl ether (IBME) by a -like organism NCIB 11650 was investigated under a variety of environmental conditions using gas chromatography. Under aerobic conditions up to 10 μg IBME ml was produced on mineral salts media containing 0.5% (w/v) glucose or succinate as sole C source with 0·1% (w/v) NHCl as sole N source. Exogenous -valine further stimulated IBME formation up to 25 μg ml but supplementation of the medium with -isomer or other amino acids had little effect on IBME production and did not lead to the appearance of analogues of IBME. Trapping experiments using [C]valine confirmed that IBME was derived from this amino acid. Several other bacterial species examined, e.g. sp. NCIB 11652, another -like organism NCIB 11651 and sp. NCIB 11653 also produced IBME under similar conditions. The strain synthesized up to 20 μg ml in the absence of valine and up to 90 μg ml in its presence.

The production of IBME exhibited many features characteristic of the formation of a secondary metabolite. Thus biosynthesis was confined to a narrower range of temperature than cell division, was almost completely suppressed by 300 m-phosphate and was inhibited by high concentrations of readily utilizable C sources. Although IBME synthesis in the -like organism NCIB 11650 appeared to be growth-related, its formation by both the sp. and the -like organism NCIB 11651 was delayed until the late-exponential and early-stationary phases of growth. The biological significance of this novel class of secondary metabolite is discussed and a possible biosynthetic route proposed.

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1982-08-01
2024-11-10
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References

  1. Castric P. A. 1975; Hydrogen cyanide, a secondary metabolite of Pseudomonas aeruginosa. . Canadian Journal of Microbiology 21:613–618
    [Google Scholar]
  2. Conn E. E. 1980; Cyanogenic glycosides. In Secondary Plant Products, pp. 461–492 Bell E. A., Charlewood B. V. Edited by Berlin, Heidelberg, New York:: Springer-Verlag;
    [Google Scholar]
  3. Demain A. L., Kennel Y. M., Aharonowitz Y. 1979; Carbon catabolite regulation of secondary metabolism. Symposia of the Society for General Microbiology 29:163–185
    [Google Scholar]
  4. Drew S. W., Demain A. L. 1977; Effect of primary metabolites on secondary metabolism. Annual Review of Microbiology 31:343–356
    [Google Scholar]
  5. Freeman L. R., Silverman G. J., Angelini P., Merritt C. Jr Esselen W. B. 1976; Volatiles produced by microorganisms isolated from refrigerated chicken at spoilage. Applied and Environmental Microbiology 32:222–231
    [Google Scholar]
  6. Gibbs P. A., Patterson J. T., Harper D. B. 1979; Some characteristics of the spoilage of sterile beef by pure cultures of bacteria. Journal of the Science of Food and Agriculture 30:1109–1110
    [Google Scholar]
  7. Hahlbrock K., Tapper B. A., Butler G. W., Conn E. E. 1968; Conversion of nitriles and ±-hydroxynitriles to cyanogenic glucosides in flax seedlings and cherry laurel leaves. Archives of Biochemistry and Biophysics 125:1013–1016
    [Google Scholar]
  8. Harper D. B. 1980; The biogenesis of unusual volatile microbial metabolites of valine. Abstracts of 13th FEBS Meeting p. 273 Jerusalem.:
    [Google Scholar]
  9. Harper D. B., Gibbs P. A. 1979; Identification of isobutyronitrile and isobutyraldoxime O-methyl ether as volatile microbial catabolites of valine. Biochemical Journal 182:609–611
    [Google Scholar]
  10. Ito M., Aida K., Vemura T. 1969; Studies on the bacterial formation of peptide antibiotic, colistin. 2. On the biosynthesis of 6-methyloctanoic and isoctan- oic acids. Agricultural and Biological Chemistry 33:262–269
    [Google Scholar]
  11. Kindl H., Underhill E. W. 1968; Biosynthesis of mustard oil glucosides: N-hydroxyphenylalanine, a precursor of glucotropaeolin and a substrate for the enzymatic and nonenzymatic formation of phenyl-acetaldehyde oxime. Phytochemistry 7:745–756
    [Google Scholar]
  12. Lee M. L., Smith D. L., Freeman L. R. 1979; High-resolution gas chromatographic profiles of volatile organic compounds produced by microorganisms at refrigerated temperatures. Applied and Environmental Microbiology 37:85–90
    [Google Scholar]
  13. Mahadevan S. 1973; Role of oximes in nitrogen metabolism in plants. Annual Review of Plant Physiology 24:69–88
    [Google Scholar]
  14. Malik V. S., Vining L. C. 1970; Metabolism of chloramphenicol by the producing organism. Canadian Journal of Microbiology 16:173–179
    [Google Scholar]
  15. Moeller B. L., Conn E. E. 1977; Biological formation of N-hydroxyamino acids. Proceedings of the Western Pharmacological Society 20:103–107
    [Google Scholar]
  16. Patterson J. T., Gibbs P. A. 1977; Incidence and spoilage potential of isolates from vacuum-packaged meat of high pH values. Journal of Applied Bacteriology 43:25–38
    [Google Scholar]
  17. Pirt S. J., Righelato R. C. 1967; Effect of growth rate on the synthesis of penicillin by Penicillium chrysogenum in batch and chemostat cultures. Applied Microbiology 15:1284–1290
    [Google Scholar]
  18. Rodgers P. B., Knowles C. J. 1978; Cyanide production and degradation during growth of Chromobacterium violaceum. . Journal of General Microbiology 108:261–267
    [Google Scholar]
  19. Stevens R. L., Emery T. F. 1966; The biosynthesis of hadacidin. Biochemistry 5:74–81
    [Google Scholar]
  20. Tapper B. A., Butler G. W. 1971; Oximes, nitriles and 2-hydroxynitriles as precursors in the biosynthesis of cyanogenic glucosides. Biochemical Journal 124:935–941
    [Google Scholar]
  21. Tapper B. A., Butler G. W. 1972; Intermediates in the biosynthesis of linamarin. Phytochemistry 11:1041–1046
    [Google Scholar]
  22. Tapper B. A., Conn E. E., Butler G. W. 1967; Conversion of ±-ketoisovaleric acid oxime and isobutyraldoxime to linamarin in flax seedlings. Archives of Biochemistry and Biophysics 119:593–595
    [Google Scholar]
  23. Underhill E. W. 1980; Glucosinolates. In Secondary Plant Products pp. 493–511 Bell E. A., Charlewood B. V. Edited by Berlin, Heidelberg, New York:: Springer-Verlag.;
    [Google Scholar]
  24. Weinberg E. D. 1970; Biosynthesis of secondary metabolites: roles of trace metals. Advances in Microbial Physiology 4:1–44
    [Google Scholar]
  25. Weinberg E. D. 1971; Secondary metabolism: raison d’être. . Perspectives in Biology and Medicine 14:565–577
    [Google Scholar]
  26. Weinberg E. D. 1974; Secondary metabolism: control by temperature and inorganic phosphate. Developments in Industrial Microbiology 15:70–81
    [Google Scholar]
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