1887

Abstract

sp., strain JCM grown photoautotrophically in the presence of naphthalene oxidized the aromatic hydrocarbon to -1,2-dihydroxy-1,2-dihydronaphthalene, 4-hydroxy-1-tetralone and 1-naphthol. The major metabolite was 1-naphthol. Each product was isolated and shown to have ultraviolet and mass spectra identical to those of authentic compounds. In addition, each metabolite had properties identical to those of authentic compounds when analysed by thin-layer, high-pressure liquid and gas-liquid chromatography. Experiments with [C]naphthalene showed that, over a 24 h period, the organism oxidized 4·8 % of the added naphthalene. The ratio of organic-soluble to water-soluble metabolites was 41:59. Incubation of whole organisms with naphthalene and O led to the isolation of 1-naphthol that contained O. The organism oxidized 1-[C]naphthol to 4-hydroxy-1-tetralone. The mechanism of naphthalene oxidation by this cyanobacterium is discussed.

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/content/journal/micro/10.1099/00221287-116-2-485
1980-02-01
2021-10-22
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References

  1. Bollag J. M., Czaplicki E. J., Minard R. D. 1975; Bacterial metabolism of 1-naphthol. Agricultural and Food Chemistry 23:85–90
    [Google Scholar]
  2. Boyland E., Ramsay G. S., Sims P. 1961; Metabolism of polycyclic compounds. 18. The secretion of metabolites of naphthalene, 1,2-dihydroxynaphthalene and 1,2-epoxy-l,2,3,4-tetrahydronaphthalene in rat bile. Biochemical Journal 78:376–384
    [Google Scholar]
  3. Catterall F. A., Murray K., Williams P. A. 1971; The configuration of the 1,2-dihydroxy-1,2-dihydronaphthalene formed in the bacterial metabolism of naphthalene. Biochimica et biophysica acta 237:361–364
    [Google Scholar]
  4. Cerniglia C. E., Gibson D. T. 1977; Metabolism of naphthalene by Cunninghamella elegans . Applied and Environmental Microbiology 34:363–370
    [Google Scholar]
  5. Cerniglia C. E., Gibson D. T. 1978; Metabolism of naphthalene by cell extracts of Cunninghamella elegans . Archives of Biochemistry and Biophysics 186:121–127
    [Google Scholar]
  6. Cerniglia C. E., Hebert R. L., Szaniszlo P. J., Gibson D. T. 1978; Fungal transformation of naphthalene. Archives of Microbiology 117:135–143
    [Google Scholar]
  7. Cerniglia C. E., Gibson D. T., Van Baalen C. 1979; Algal oxidation of aromatic hydrocarbons: formation of 1-naphthol from naphthalene by Agmenellum quadruplicatum, strain PR-6. Biochemical and Biophysical Research Communications 88:50–58
    [Google Scholar]
  8. Cerniglia C. E., Gibson D. T., Van Baalen C. 1980; Oxidation of naphthalene by cyanobacteria and microalgae. Journal of General Microbiology 116:495–500
    [Google Scholar]
  9. Corner E. D. S., Young L. 1954; Biochemical studies of toxic agents. 7. The metabolism of naphthalene in animals of different species. Biochemical Journal 58:647–655
    [Google Scholar]
  10. Dagley S. 1971; Catabolism of aromatic compounds by microorganisms. Advances in Microbial Physiology 6:1–46
    [Google Scholar]
  11. Davies J. I., Evans W. C. 1964; Oxidative metabolism of naphthalene by soil pseudomonads. Biochemical Journal 91:251–261
    [Google Scholar]
  12. Ellis B. E. 1977; Degradation of phenolic compounds by fresh-water algae. Plant Science Letters 8:213–216
    [Google Scholar]
  13. Ferris J. P., Fasco M. J., Stylianopoulou F. L., Jerina D. M., Daly J. W., Jeefrey A. M. 1973; Mono-oxygenase activity in Cunninghamella bainieri: evidence for a fungal system similar to liver microsomes. Archives of Biochemistry and Biophysics 156:97–103
    [Google Scholar]
  14. Gordon D. C., Prouse N. J. 1973; The effects of three oils on marine phytoplankton photosynthesis. Marine Biology 22:329–333
    [Google Scholar]
  15. Griffiths E., Evans W. C. 1965; A cell-free perhydroxylase system from soil pseudomonads. Biochemical Journal 95:51
    [Google Scholar]
  16. Jeffrey A. M., Yeh H. J. C., Jerina D. M., Patel T. R., Davey J. F., Gibson D. T. 1975; Initial reactions in the oxidation of naphthalene by Pseudomonas putida . Biochemistry 14:575–584
    [Google Scholar]
  17. Jerina D. M., Daly J. W., Witkop B., Zaltzman-Nirenberg P., Udenfriend S. 1968; The role of arene oxide-oxepin systems in the metabolism of aromatic substrates. III. Formation of 1,2-naphthalene oxide from naphthalene by liver microsomes. Journal of the American Chemical Society 90:6525–6527
    [Google Scholar]
  18. Jerina D. M., Daly J. W., Witkop B., Zaltzman-Nirenberg P., Udenfriend S. 1970; 1,2-Naphthalene oxide as an intermediate in the microsomal hydroxylation of naphthalene. Biochemistry 9:147–156
    [Google Scholar]
  19. Jerina D. M., Daly J. W., Jeffrey A. M., Gibson D. T. 1971; cis-l,2-Dihydroxy-l,2-dihydronaphthalene : a bacterial metabolite from naphthalene. Archives of Biochemistry and Biophysics 142:394–396
    [Google Scholar]
  20. Jerina D. M., Selander H., Yagi H., Wells M. C., Davey J. F., Mahadevan V., Gibson D. T. 1976; Dihydrodiols from anthracene and phenanthrene. Journal of the American Chemical Society 98:5988–5996
    [Google Scholar]
  21. Kusk K. O. 1978; Effects of crude oil and aromatic hydrocarbons on the photosynthesis of the diatom Nitzschia . Physiologia plantarum 43:1–6
    [Google Scholar]
  22. Miller E. C., Miller J. A. 1974; Biochemical mechanisms of chemical carcinogenesis. In Molecular Biology of Cancer pp. 377–402 Edited by Bush H. New York: Academic Press;
    [Google Scholar]
  23. Morgan J. C. 1975 Studies of the diatoms of the Northwestern Gulf of Mexico: identification, distribution and cultural studies Master’s thesis, University of Texas at Austin, Austin, Texas, U.S.A.
    [Google Scholar]
  24. Myers J. 1950; The culturing of algae for physiological research. In The Culturing of Algae pp. 45–51 Edited by Brunei J., Prescott G. W., Tiffany L. H. Yellow Springs, Ohio, U.S.A.: Charles F. Kettering Foundation;
    [Google Scholar]
  25. Oesch F., Jerina D. M., Daly J. W. 1971; Conversion of naphthalene to tnmv-naphthalene dihydrodiol: evidence for the presence of a coupled aryl monooxygenase-epoxide hydrase system in hepatic microsomes. Biochemical and Biophysical Research Communications 46:1713–1720
    [Google Scholar]
  26. Oesch F., Jerina D. M., Daly J. W., Lu A. Y. H., Kuntzman R., Conney A. J. 1972; A reconstituted microsomal enzyme system that converts naphthalene to trans-l,2-dihydroxy-1,2-dihydronaphthalene via naphthalene-1,2-oxide. Presence of epoxide hydrase in cytochrome P-450 and P-448 fractions. Archives of Biochemistry and Biophysics 153:62–67
    [Google Scholar]
  27. Patel T. R., Gibson D. T. 1974; Purification and properties of (+)-cis-naphthalene dihydrodiol dehydrogenase of Pseudomonas putida . Journal of Bacteriology 119:879–888
    [Google Scholar]
  28. Pulich W. M. JR Winters K., Van Baalen C. 1974; The effects of No. 2 fuel oil and two crude oils on the growth and photosynthesis of microalgae. Marine Biology 28:87–94
    [Google Scholar]
  29. Soto C., Hellebust A. J., Hutchinson T. C., Sawa T. 1975a; Effect of naphthalene and aqueous crude oil extracts on the green flagellate Chlamydomonas angulosa. I. Growth. Canadian Journal of Microbiology 53:109–117
    [Google Scholar]
  30. Soto C., Hellebust A. J., Hutchinson T. C. 1975b; Effect of naphthalene and aqueous crude oil extracts on the green flagellate Chlamydomonas angulosa. II. Photosynthesis and the uptake and release of naphthalene. Canadian Journal of Microbiology 53:118–126
    [Google Scholar]
  31. Treccani V., Walker N., Wiltshire G. H. 1954; The metabolism of naphthalene by soil bacteria. Journal of General Microbiology 11:341–348
    [Google Scholar]
  32. Van Baalen C. 1962; Studies on marine blue-green algae. Botanica marina 4:129–139
    [Google Scholar]
  33. Walker N., Wiltshire G. H. 1953; The breakdown of naphthalene by a soil bacterium. Journal of General Microbiology 8:273–276
    [Google Scholar]
  34. Winters K., O’Donnell R., Batterton J. C., Van Baalen C. 1976; Water soluble components of four fuel oils: chemical characterization and effects on growth of microalgae. Marine Biology 36:269–276
    [Google Scholar]
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