Skip to main content
Log in

6-Thioguanine fromErwinia amylovora

  • Published:
Current Microbiology Aims and scope Submit manuscript

Abstract

Erwinia amylovora, the etiological agent of fireblight disease, was found to produce under aerobic conditions in axenic culture 2-amino-1,7-dihydro-6H-purine-6-thion (6-thioguanine, 6-TG), easily recognized by a UV absorbance at 340 nm (pH≤7) and readily distinguished from NADH by both its acid stability and the pH dependence of its UV spectrum. 6-TG is known for a variety of physiological activities, but in this study no toxicity toward Bartlett pear suspension culture was detected. Although a synergistic role of 6-TG in the development of fireblight is not excluded, it may not be responsible for the black necrosis typical for the disease. This conclusion was corroborated through the study of severalE. amylovora mutants with respect to their capability to produce 6-TG.

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

Literature Cited

  1. Ayers AR, Ayers SB, Goodman RN (1979) Extracellular polysaccharide ofErwinia amylovora: a correlation with virulence. Appl Environ Microbiol 38:659–666

    Google Scholar 

  2. Bauer DW, Beer SV (1983) Evidence that the activity of a putative necrotoxin ofErwinia amylovora is due to the action of inorganic salts. Phytopathology 73:362

    Google Scholar 

  3. Bennett RA, Billing E (1980) Origin of the polysaccharide component of ooze from plants infected withErwinia amylovora. J Gen Microbiol 116:341–349

    Google Scholar 

  4. Bernofsky C (1981) Chromatographic stability of acid-modified reduced nicotinamide adenine dinucleotide (NADH). Physiol Chem Phys 13:3–10

    Google Scholar 

  5. Billing E (1984) Studies on avirulent strains ofErwinia amylovora. Acta Hortic 151:249–253

    Google Scholar 

  6. Breitmaier E, Voelter W (1974)13C NMR spectroscopy. Weinheim. Verlag Chemie, p 250

    Google Scholar 

  7. Breter HJ, Zahn RK (1977) The quantitative determination of metabolites of 6-mercaptopurine in biological materials. II. Advantages of a variable-wavelength HPLC spectrophotometric detector for the determination of 6-thiopurines. J Chromatogr 137:61–68

    PubMed  Google Scholar 

  8. Bruice TC, Benkovic SJ (1966) Nicotinamide nucleotides. In: Bruice TC, Benkovic SJ (eds) Bioorganic mechanisms. New York: WA Benjamin, pp 301–349

    Google Scholar 

  9. Buchanan GE, Starr MP (1980) Phytotoxic material from associations betweenErwinia amylovora and pear tissue culture: possible role in necrotic symptomatology of fireblight disease. Curr Microbiol 4:63–68

    Google Scholar 

  10. Burkowicz A, Goodman RN (1969) Permeability alterations induced in apple leaves by virulent and avirulent strains ofErwinia amylovora. Phytopathology 59:314–318

    Google Scholar 

  11. Durbin RD (1983) Future prospects in toxin research. In: Daly JD, Deverall BJ (eds) Toxins and plant pathogenesis. New York: Academic Press, pp 159–177

    Google Scholar 

  12. Fawcett CP, Ciotti MM, Kaplan NO (1961) Inhibition of dehydrogenase reactions by a substance formed from reduced diphosphopyridine nucleotide. Biochim Biophys Acta 54:210–212

    PubMed  Google Scholar 

  13. Finkel JM (1975) Fluorometric assay of thioguanine. J Pharm Sci 64:121–122

    PubMed  Google Scholar 

  14. Fox JJ, Wempen I, Hampton A, Doerr IL (1957) Thiation of nucleosides. I. Synthesis of 2-amino-6-mercapto-9-β-d-ribo-furanosylpurine (“thioguanosine”) and related purine nucleosides. J Am Chem Soc 80:1669–1675

    Google Scholar 

  15. Harris BA, Weigent DA, Nelson JA (1979) Effects of 6-thiopurines on the transforming activity ofBacillus subtilis deoxyribonucleic acid. Biochem Pharmacol 28:1169–1173

    PubMed  Google Scholar 

  16. Heinze JE, Mitani T, Rich KE, Freese E (1978) Induction of sporulation by inhibitory purines and related compounds. Biochim Biophys Acta 521:16–26

    PubMed  Google Scholar 

  17. Helgeson JP, Deverall BJ (eds) (1983) Use of tissue culture and protoplasts in plant pathology. New York: Academic Press

    Google Scholar 

  18. Hildebrand EM (1939) Studies on fireblight ooze. Phytopathology 29:142–156

    Google Scholar 

  19. Hollomon DW (1979) Evidence that ethirimol may interfere with adenine metabolism during primary infection of barley powdery mildew. Pestic Biochem Physiol 10:181–189

    Google Scholar 

  20. Iwakura M, Tokushige M, Katsuki H (1979) Studies on regulatory functions of malic enzymes. VII. Structural and functional characteristics of sulfhydryl groups in NADP-linked malic enzyme fromEscherichia coli W. J Biochem 86:1239–1249

    PubMed  Google Scholar 

  21. Kastrup EK, Boyd JR (1985) Drug: facts and comparisons. Philadelphia: Lippincott

    Google Scholar 

  22. Klement Z, Goodman RN (1967) The hypersensitive reaction to infection by bacterial plant pathogens. Annu Rev Phytopathol 5:17–44

    Google Scholar 

  23. Lee SH, Sartorelli AC (1981) Conversion of 6-thioguanine to the nucleoside level by purine nucleoside phosphorylase of sarcoma 180 and sarcoma 180/TG ascites cells. Cancer Res 41:1086–1090

    PubMed  Google Scholar 

  24. Lindemans-Bänziger CIM, Van der Steen ATM, Staal GEJ (1976) The influence of 6-mercaptopurine and some of its derivatives on human erythrocyte phosphofructokinase. J Mol Med 1:117–125

    Google Scholar 

  25. Loewus FA, Loewus MW (1983) myo-Inositol: its biosynthesis and metabolism. Annu Rev Plant Physiol 34:137–161

    Google Scholar 

  26. Lovrekovich L, Lovrekovich H, Goodman RN (1970) The relationship of ammonia to symptom expression in apple shoots inoculated withErwinia amylovora. Can J Bot 48:999–1000

    Google Scholar 

  27. Maddocks JL, Davidson GS (1975) Separation and detection of picomole quantities of azathioprine metabolites. Br J Clin Pharmacol 2:359–360

    PubMed  Google Scholar 

  28. Mandel HG (1967) Comparative actions of some purine analogues on growingBacillus cereus. Fed Proc Fed Am Soc Exp Biol 26:905–906

    Google Scholar 

  29. Mehta BM, Hutchison DJ (1975) Inhibition of microorganisms by pyrimidine nucleosides. Ann NY Acad Sci 255:559–563

    PubMed  Google Scholar 

  30. Miller TD, Schroth MN (1972) Monitoring the epiphytic population ofErwinia amylovora on pear with a selective medium. Phytopathology 62:1175–1182

    Google Scholar 

  31. Mitchell RE (1981) Structure: bacterial. In: Durbin RD (ed) Toxins in plant disease. New York: Academic Press, pp 259–293

    Google Scholar 

  32. Murashige T, Skoog F (1962) A revised medium for rapid growth and bioassays with tobacco tissue cultures. Physiol Plant 15:473–497

    Google Scholar 

  33. Nelson DJ, Bugge CJL, Krasny HC, Zimmerman TP (1973) Separation of 6-thiopurine derivatives on DEAE-Sephadex columns and in the high-pressure liquid chromatograph. J Chromatogr 77:181–190

    PubMed  Google Scholar 

  34. Nygaard P (1983) Utilization of preformed purine bases and nucleosides. In: Munch-Petersen A (ed) Metabolism of nucleotides, nucleosides and nucleobases in microorganisms. New York: Academic Press, pp. 27–93 (see p 65)

    Google Scholar 

  35. Pech JC, Ambid C, Latché A, Diarra A, Fallot J (1975) Culture de tissus et de suspensions cellulaires de fruits: moyen d'étude de certains aspects de la maturation. In: Ulrich R (ed) Colloques Internationaux du Centre National de la Recherche Scientifique: facteurs et régulation de la maturation des fruits. Paris: Editions du Centre National de la Recherche Scientifique, pp 211–220

    Google Scholar 

  36. Pech JC, Romani RJ (1979) Senescence of pear fruit cells cultured in a continuously renewed, auxin-deprived medium. Plant Physiol 63:814–817

    Google Scholar 

  37. Porath J (1956) Methodological studies of zone-electrophoresis in vertical columns. I. Fractionation in cellulose powder columns of substances of low molecular weight exemplified by amino acids and related compounds. Biochim Biophys Acta 22:151–175

    PubMed  Google Scholar 

  38. Raymundo AK, Ries SM (1980) Chemotaxis ofErwinia amylovora. Phytopathology 70:1066–1069

    Google Scholar 

  39. Scannell JP, Pruess DL, Kellett M, Demny TC, Stempel A (1971) Antimetabolites produced by microorganisms. III. 2-Aminopurine-6-thiol (thioguanine). J Antibiot (Tokyo) 24:328–329

    Google Scholar 

  40. Schenk RU, Hildebrandt AC (1972) Medium and techniques for induction and growth of monocotyledonous and dicotyledonous plant cell cultures. Can J Bot 50:199–204

    Google Scholar 

  41. Schraudolf H (1967) Wirkung von Hemmstoffen der DNS-, RNS- und Proteinsynthese auf Wachstum und Antheridienbildung in Prothallien vonAnemia phyllitidis L. Planta (Berlin) 74:123–147

    Google Scholar 

  42. Seemüller EA, Beer SV (1976) Absence of cell wall polysaccharide degradation byErwinia amylovora. Phytopathology 66:433–436

    Google Scholar 

  43. Seemüller E, Beer SV (1977) Isolation and partial characterization of two neutral proteases ofErwinia amylovora. Phytopathol Z 90:12–21

    Google Scholar 

  44. Shaw PD (1981) Production and isolation. In: Durbin RD (ed) Toxins in plant disease. New York: Academic Press, pp 21–44

    Google Scholar 

  45. Singha S, Powell LE (1979) Effect of purine analogs and their interactions with benzyladenine on bud burst and shoot growth in apple bud explants. Physiol Plant 47:167–172

    Google Scholar 

  46. Van der Zwet T, Keil HL (1979) Fire blight: a bacterial disease of rosaceous plants. Agriculture handbook no. 510. Washington: US Government Printing Office

    Google Scholar 

  47. Yamaki S (1984) Isolation of vacuoles from immature apple fruit flesh and compartmentation of sugars, organic acids, phenolic compounds and amino acids. Plant Cell Physiol 25:151–166

    Google Scholar 

  48. Ziegler H (1975) Nature of transported substances. In: Zimmermann MH, Milburn JA (eds) Transport in plants. I. Phloem transport. New York: Springer, pp 59–100

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

Feistner, G., Staub, C.M. 6-Thioguanine fromErwinia amylovora . Current Microbiology 13, 95–101 (1986). https://doi.org/10.1007/BF01568289

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF01568289

Keywords

Navigation