Skip to main content
Log in

Production and composition of phenylpyrrole metabolites prodcued by Pseudomonas cepacia

  • Applied Microbiology
  • Published:
Applied Microbiology and Biotechnology Aims and scope Submit manuscript

Summary

In shaken cultures, a strain of Pseudomonas cepacia isolated from apple leaves produced pyrrolnitrin and four other phenylpyrrole antibiotics. The concentrations of these metabolites were determined at intervals for 7 days in three different media at two initial pH levels. Optical density measurements revealed maximum cell concentrations after 24 h in nutrient broth, after 48 h in King's B medium, and after 96 h in minimum salts solution. The effects caused by initiating fermentations at pH 5.8 rather than 7.0 were in most cases not dramatic, although in some instances, especially in minimum salts broth, higher concentrations of metabolites were produced with the lower initial pH. Concentrations of the phenylpyrrole antibiotics were greatly affected by choice of culture medium and incubation time. Concentrations of the two nitrophenyl metabolites, pyrrolnitrin and 2-chloropyrrolnitrin, rose throughout the 7-day incubation and were more than 20 times greater in minimum salts medium than in either King's B medium or nutrient broth. The maximum concentrations of each of the three aminophenyl metabolites (dichloroamino, trichloroamino and monochloroamino) occurred in different media, the monochloro compound in nutrient broth, the dichloro compound in Kings B medium and the trichloro compound in minimum salts medium. The time dependence of the concentrations of the five metabolites supports the proposed biosynthesis of these pyrroles from tryptophan by successive chlorinations followed by oxidation of the amino group at the end of the pathway.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  • Arima K, Imanaki H, Kousaka M, Fukuta A, Tamura G (1964) Pyrrolnitrin, a new antibiotic substance, produced by Psneudomonas. Agric Biol Chem 28:575–576

    Google Scholar 

  • Arima K, Imanaki H, Kousaka M, Fukuda A, Tamura G (1965) Studies on pyrrolnitrin a new antibiotic. I. Isolation and properties of pyrrolnitrin. J Antibiot A18:201–204

    Google Scholar 

  • Chang CJ, Floss HG, Hook DJ, Mabe JA, Manni PE, Martin LL, Schröder K, Shieh TL (1981) The biosynthesis of the antibiotic pyrrolnitrin by Pseudomonas aureofaciens. J Antibiot 34:555–566

    Google Scholar 

  • Elander R, Mabe J, Hamill R, Gorman M (1968) Metabolism of tryptophans by Pseudomonas aureofaciens VI. Production of pyrrolnitrin by selected Pseudomonas species. Appl Microbiol 1968:753–758

    Google Scholar 

  • Floss HG, Manni PE, Hamill RL, Mabe JA (1971) Further studies on the biosynthesis of pyrrolnitrin from tryptophan by Pseudomonas. Biochem Biophys Res Commun 45:781–787

    Google Scholar 

  • Hamill R, Elander R, Mabe J, Gorman M (1967) Metabolism of tryptophans by Pseudomonas aureofaciens V. Conversion of tryptophan to pyrrolnitrin. Antimicrob Agents Chemother 1967:388–396

    Google Scholar 

  • Hamill R, Elander R, Mabe J, Gorman M (1970) Metabolism of tryptophans by Pseudomonas aureofaciens III. Production of substituted pyrrolnitrins from tryptophan analogs. Appl Microbiol 19:721–725

    Google Scholar 

  • Imanaka H, Kousaka M, Tamura G, Arima K (1965a) Studies on pyrrolnitrin, a new antibiotic. II Taxonomic studies on pyrrolnitrin-producing strain. J Antibiot A18:205–206

    Google Scholar 

  • Imanaka H, Kousaka M, Tamura G, Arima K (1965b) Studies on pyrrolnitrin, a new antibiotic. III Structure of pyrrolnitrin. J Antibiot A18:207–210

    Google Scholar 

  • Janisiewicz WJ, Roitman JN (1987) Postharvest Mucor rot control on apples with Pseudomonas cepacia. Phytopathology 77:1776

    Google Scholar 

  • Janisiewicz WJ, Roitman JN (1988) Biological control of blue mold and gray mold on apple and pear with Pseudomonas cepacia. Phytopathology 78:1697–1700

    Google Scholar 

  • Lively DH, Gorman M, Haney ME, Mabe JA (1966) Metabolism of tryptophans by Pseudomonas auerofaciens I. Biosynthesis of pyrrolnitrin. Antimicrob Agents Chemother 1966:462–469

    Google Scholar 

  • Mahoney NE, Roitman JN (1990) High-performance liquid chromatographic separation of phenylpyrroles produced by Pseudomonas cepacia. J Chromatogr 508:247–251

    Google Scholar 

  • Pee K-H van, Salcher O, Lingens F (1980) Formation of pyrrolnitrin and 3-(2-amino-3-chlorophenyl)-pyrrole from 7-chlorotryptophan. Angew Chem Int Ed Engl 19:828–829

    Google Scholar 

  • Roitman JN, Mahoney NE, Janisiewicz WJ, Benson M (1990) A new chlorinated phenylpyrrole antibiotic produced by the antifungal bacterium Pseudomonas cepacia. J Agric Food Chem 38:538–541

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

Roitman, J.N., Mahoney, N.E. & Janisiewicz, W.J. Production and composition of phenylpyrrole metabolites prodcued by Pseudomonas cepacia . Appl Microbiol Biotechnol 34, 381–386 (1990). https://doi.org/10.1007/BF00170064

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00170064

Keywords

Navigation