Skip to main content
Log in

Stoffwechselprodukte von Mikroorganismen

154. Mitteilung. Nikkomycin, ein neuer Hemmstoff der Chitinsynthese bei Pilzen

Metabolic products of microorganisms

154. Nikkomycin, a new inhibitor of fungal chitin synthesis

  • Published:
Archives of Microbiology Aims and scope Submit manuscript

Abstract

From the fermentation broth of Streptomyces tendae Tü 901 a substance was isolated, which inhibits the growth of several fungi. The new antibiotic affects the chitchin biosynthesis. Its structure was identified by mass spectrometry of the products obtained after chemical degradation. Nikkomycin is a nucleoside-peptide antibiotic consisting of uracil, an amino hexuronic acid and a new amino acid containing a pyridin ring.

Zusammenfassung

Der Streptomycet Tü 901, Streptomyces tendae, bildet ein antifungisch wirkendes Nukleosid-Antibioticum, Nikkomycin. Als Angriffsort kommt die Chitinsynthese in Frage.

Mit Hilfe der Massenspektrometrie und des chemischen Abbaus konnten Uracil, eine Aminohexuronsäure und eine neue, einen Pyridinring enthaltende Aminosäure nachgewiesen werden.

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

Literatur

  • Bartnicki-Garcia, S., Lippman, E.: Inhibition of Mucor rouxii by polyoxin D: Effect on chitin synthetase and morphological development. J. gen. Microbiol. 71, 301–309 (1972)

    Google Scholar 

  • Bayer, E., Gugel, K. H., Hägele, K., Hagenmaier, H., Jessipow, S., König, W. A., Zähner, H.: Phosphinothricin und Phosphinothricyl-Alanyl-Alanin. Helv. chim. Acta 55, 224–239 (1972)

    Google Scholar 

  • Betina, V., Betinova, M., Kutkova, M.: Effect of cyanein on growth and morphology of pathogenic fungi. Arch. Mikrobiol. 55, 1–16 (1966)

    Google Scholar 

  • Betz, A.: Enzyme. Gewinnung, Analyse, Regulation. Weinheim: Verlag Chemie 1974

    Google Scholar 

  • Corbaz, R., Ettlinger, L., Keller-Schierlein, W., Zähner, H.: Zur Systematik der Actinomyceten. 1. Über Streptomyceten mit rhodomycinartigen Pigmenten. Arch. Mikrobiol. 25, 325–332 (1957)

    Google Scholar 

  • Endo, A., Kakiki, K., Misato, T.: Mechanism of action of the antifungal agent polyoxin D. J. Bact. 104, 189–196 (1970)

    Google Scholar 

  • Fuller, M. S., Barshad, I.: Chitin and cellulose in the cell walls of Rhizidiomyces sp. Amer. J. Bot. 47, 105–109 (1960)

    Google Scholar 

  • Gale, G. R.: Effects of the antifungal peptides Ro-27758 on morphology of Mucor corymbifera. J. Bact. 85, 833–837 (1963)

    Google Scholar 

  • Glaser, L., Brown, D. H.: The enzymatic synthesis in vitro of hyaluronic acid chains. Proc. nat. Acad. Sci. (Wash.) 41, 253–260 (1955)

    Google Scholar 

  • Glaser, L., Brown, D. H.: The synthesis of chitin in cell-free extracts of Neurospora crassa. J. biol. Chem. 228, 729–742 (1957)

    Google Scholar 

  • Gottlieb, D., Carter, H. E., Lungi-chi Wu, Sloneker, J. H.: Inhibition of fungi by filipin and its antagonism by steroly. Phytopathology 50, 594–603 (1960)

    Google Scholar 

  • Hashimoto, T., Kito, M., Takeuchi, T., Hamada, M., Maeda, K., Okami, Y., Umezawa, H.: Ablastmycin, a new anti-priricularia antibiotic. J. Antibiot. A 21, 37–43 (1968)

    Google Scholar 

  • Hori, M., Kakiki, K., Misato, T.: Interacion between polyoxin and active center of chitin synthetase. Agr. Biol. Chem. 38, 699–705 (1974)

    Google Scholar 

  • Hütter, R.: Systematik der Streptomyceten. Basel-New York: Karger 1967

    Google Scholar 

  • Hütter, R., Keller-Schierlein, W., Nüesch, J., Zähner, H.: Stoffwcchselprodukte von Mikroorganismen. 48. Mitteilung. Scopamycine. Arch. Mikrobiol. 51, 1–8 (1965)

    Google Scholar 

  • Hütter, R., Poralla, K., Zachau, H. G., Zähner, H.: Stoffwechselprodukte von Mikroorganismen. 51. Mitteilung. Über die Wirkungsweise von Borrelidin-Hemmung des Threonineinbaus in sRNS. Biochem. Z. 344, 190–196 (1966)

    Google Scholar 

  • Isono, K., Asahi, K., Suzuki, S.: Studies on polyoxins, antifungal antibiotics. XIII. The structure of polyoxins. J. Amer. chem. Soc. 91, 7490–7505 (1969)

    Google Scholar 

  • Isono, K., Kobinata, K., Suzuki, S.: Isolation and characterization of polyoxins J, K and L, new components of polyoxin complex. Agr. Biol. Chem. 32, 792–793 (1968)

    Google Scholar 

  • Isono, K., Nagatsu, J., Kawashima, Y., Suzuki, S.: Studies on polyoxins, antifungal antibiotics. Part I. Isolation and characterization of polyoxins A and B Agr. Biol. Chem. 29, 848–854 (1965)

    Google Scholar 

  • Isono, K., Nagatsu, J., Kobinata, K., Sasaki, K., Suzuki, S.: Studies on polyoxins, antifungal antibiotics. Part. V. Isolation and characterization of polyoxins C, D, E, F, G, H and I. Agr. Biol. Chem. 31, 190–199 (1967)

    Google Scholar 

  • Jan, Y. N.: Properties and cellular localization of chitin synthetase in Phycomyces blakesleeanus. J. biol. Chem. 249, 1973–1979 (1974)

    Google Scholar 

  • Keller, F. A., Cabib, E.: Chitin and yeast budding. Properties of chitin synthetase from Saccharomyces carlsbergensis. J. biol. Chem. 246, 160–166 (1971)

    Google Scholar 

  • Kirst, G.: Untersuchungen zur Hemmung der Zygosporenbildung bei Mucor hiemalis. Dissertation, Universität Tübingen (1971)

  • de Kleot, S. R.: Ribonucleic acid synthesis in yeast. The effect of cycloheximid on the synthesis of ribonucleic acid in Saccharomyces carlsbergensis. Biochem. J. 99 566–581 (1966)

    Google Scholar 

  • Kneifel, H., König, W. A., Wolf, G., Zähner, H.: Metabolic products of microorganisms. 123.: Thraustomycin, a new antifungal nucleoside antibiotic from Streptomyces exfoliatus. J. Antibiot. A 27, 20–27 (1974)

    Google Scholar 

  • König, W. A., Bauer, H., Voelter, W., Bayer, E.: Gaschromatographie und Massenspektrometrie von trifluorcetylierten Kohlehydraten. Chem. Ber. 106, 1905–1979 (1973)

    Google Scholar 

  • König, W. A., Smith, L. C., Crain, P. F., McCloskey, J. A.: Mass spectrometry of trifluoracetyl derivatives of nucleosides and hydrolysates of deoxyribonucleic acids. Biochemistry 10, 3968–3979 (1971)

    Google Scholar 

  • König, W. A., Zech, K., Uhmann, R., Voelter, W.: Massenspektrometrische Untersuchungen von Analogen des Adenosins. Chem. Ber. 105, 262–272 (1972)

    Google Scholar 

  • Leloir, L. F., Cardini, C. E.: The biosynthesis of glucosamin. Biochim. biophys. Acta (Amst.) 12, 15–22 (1953)

    Google Scholar 

  • Lineweaver, H., Burk, D.: The determination of enzyme dissociation constants. J. Amer. chem. Soc. 56, 658–666 (1934)

    Google Scholar 

  • Links, J., Rombouts, J. R., Keulen, P.: The “bulging factor”, a fungistatic antibiotic produced by a streptomyces strain, with evidence of an active waterexcreting mechanism in fungi. J. gen. Microbiol. 17, 596–600 (1957)

    Google Scholar 

  • Mahl, D.: Ropalocidin, ein antifungisches Antibiotikum aus Streptomyces violaceoniger. Dissertation, Universität Tübingen (1971)

  • McCloskey, J. A., Stillwell, R. N., Lawson, A. M.: Use of deuterium-labeled trimethylsilyl derivatives in mass spectrometry. Analyt. Chem. 40, 233–236 (1968)

    Google Scholar 

  • McMurrough, I., Bartnicki-Garcia, S.: Properties of a particulate chitin synthetase from Mucor rouxii. J. biol. Chem. 246, 4008–4016 (1971)

    Google Scholar 

  • McMurrough, I., Flores-Carreon, A., Bartnicki-Garcia, S.: Pathway of chitin synthesis and cellular localization of chitin synthetase in Mucor rouxii. J. biol. Chem. 246, 3999–4007 (1971)

    Google Scholar 

  • Mizuno, M., Shimojima, Y., Sugawara, T., Takeda, I.: An antibiotic 24010. J. Antibiot. A 24, 896–899 (1971)

    Google Scholar 

  • Müller, A.: siderochrome aus Mikroorganismen. Dissertation, Universität Tübingen (1968)

  • Paulsen, H., Mäckel, E.: Synthese und Reaktionen von 5-Amino-5-desoxy-l-iduronsäure. Chem. Ber. 106, 1252–1536 (1973)

    Google Scholar 

  • Porter, C. A., Jaworski, E. G.: Biosynthesis of chitin during various stages in the metamorphosis of Proeenia eridania. J. Insect Physiol. 11, 1151–1160 (1965)

    Google Scholar 

  • Reissig, J.: Phosphoacetylglucosamine mutase of Neurospora. J. biol. Chem. 219, 753–767 (1956)

    Google Scholar 

  • Shoji, J., Sakazaki, R., Mayama, M., Kawamura, Y., Yasuda, Y.: A new antibiotic bulgerin, active against phytopathogenic fungi. J. Antibiot. A 23, 295–299 (1970)

    Google Scholar 

  • Siddhikol, C., Erbstoeszer, J.W., Weisblum, B.: Mode of action of streptolydigin. J. Bact. 99, 151–155 (1969)

    Google Scholar 

  • Siegel, M. R., Sisler, H. D.: Site of action of cycloheximide in cells of Saccharomyces pastorianus. I. Effects of the antibiotic on cellular metabolism. Biochim. biophys. Acta (Amst.) 87, 70–82 (1964a)

    Google Scholar 

  • Siegel, M. R., Sisler, H. D.: Site of action of cycloheximide in cells of Saccharomyces pastorianus. II. The nature of inhibition of protein synthesis in a cell-free system. Biochim. Biophys. Acta (Amst.) 87, 83–89 (1964b)

    Google Scholar 

  • Störl, K., Venner, H.: Einbau von Thymin und Thymidin in die DNS von Proteus mirabilis. Z. allg. Mikrobiol. 12, 479–486 (1972)

    Google Scholar 

  • Suhadolnik, R. J.: Nucleoside antibiotics. New York: Wiley 1970

    Google Scholar 

  • Weygand, F., Rinno, H.: Serin-und Thereonin-Verbindungen. Chem. Ber. 92, 517–527 (1959)

    Google Scholar 

  • Wolf, H.: Kirromycin, ein Hemmstoff der Funktion der ribosomalen 30S-Untereinheit. Dissertation, Universität Tübingen (1971)

Download references

Author information

Authors and Affiliations

Authors

Additional information

153. Mitteilung: G. Wolf, J. Wörth, H. Achenbach: Untersuchungen der Pigmente aus Streptomyces michiganesis. Arch. Microbiol. 106, 245–249 (1975)

Rights and permissions

Reprints and permissions

About this article

Cite this article

Dähn, U., Hagenmaier, H., Höhne, H. et al. Stoffwechselprodukte von Mikroorganismen. Arch. Microbiol. 107, 143–160 (1976). https://doi.org/10.1007/BF00446834

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00446834

Key words

Navigation