Abstract
Eighty-six species of fungi belonging to sixty-four genera were examined for their ability to metabolize naphthalene. Analysis by thin-layer and high pressure liquid chromatography revealed that naphthalene metabolism occurred in forty-seven species belonging to thirty-four genera from the major fungal taxa. All organisms tested from the order Mucorales oxidized naphthalene with species of Cunninghamella, Syncephalastrum and Mucor showing the greatest activity. Significant metabolism was also observed with Neurospora crassa, Claviceps paspali and four species of Psilocybe. The predominant metabolite formed by most organisms was 1-naphthol. Other products identified were, 4-hydroxy-1-tetralone, trans-1,2-dihydroxy-1,2-dihydronaphthalene, 2-naphthol, 1,2-and 1,4-naphthoquinone.
Similar content being viewed by others
References
Ambike, S. H., Baxter, R. M., Zahid, N. D.: The relationships of cytochrome P-450 levels and alkaloid synthesis in Claviceps purpurea. Phytochemistry 9, 1953–1958 (1970)
Auret, B. J., Boyd, D. R. Robinson, P. M., Watson, C. G., Daly, J. W., Jerina, D. M.: The NIH Shift during the hydroxylation of aromatic substrates by fungi. Chem. Commun. 1585–1587 (1971)
Blumer, M.: Polycyclic aromatic hydrocarbons in nature. Sci. Am. 234, 34–44 (1976)
Bollag, J. M., Czaplicki, E. J., Minard, R. D.: Bacterial metabolism of 1-naphthol. Agric. Food Chem. 23, 85–90 (1975)
Catterall, F. A., Murray, K., Williams, P. A.: The configuration of the 1,2-dihydroxy-1,2-dihydronaphthalene formed in the bacterial metabolism of naphthalene. Biochim. Biophys. Acta 237, 361–364 (1971)
Cerniglia, C. E., Gibson, D. T.: Metabolism of naphthalene by Cunninghamella elegans. Appl. Environ. Microbiol. 34, 363–370 (1977)
Cerniglia, C. E., Gibson, D. T.: Metabolism of naphthalene by cell extracts of Cunninghamella elegans. Arch. Biochem. Biophys. (1978, in press)
Dagley, S.: Catabolism of aromatic compounds by microorganisms. Adv. Microbial. Physiol. 6, 1–46 (1971)
Daly, J. W., Jerina, D. M., Witkop, B.: Arene oxides and the NIH shift: The metabolism, toxicity and carcinogenicity of aromatic compounds. Experientia 28, 1129–1149 (1972)
Duppel, W., Lebeault, J. J., Coon, M. J.: Properties of a yeast cytochrome P-450 containing enzyme system which catalyzes the hydroxylation of fatty acids, alkanes, and drugs. Eur. J. Biochem. 36, 583–592 (1973)
Ferris, J. P., Fasco, M. J., Stylianopoulou, F. L., Jerina, D. M., Daly, J. W., Jeffrey, A. M.: Monooxygenase activity in Cunninghamella bainieri: Evidence for a fungal system similar to liver microsomes. Arch. Biochem. Biophys. 156, 97–103 (1973)
Ferris, J. P., MacDonald, L. H., Patrie, M. A., Martin, M. A.: Aryl hydrocarbon hydroxylase activity in the fungus Cunninghamella bainieri: Evidence for the presence of cytochrome P-450. Arch. Biochem. Biophys. 175, 443–452 (1976)
Gallo, M., Roche, B., Azoulay, E.: Microsomal cytochromes of Candida tropicalis grown on alkanes. Biochim. Biophys. Acta 419, 425–434 (1976)
Gibson, D. T.: The microbial oxidation of aromatic hydrocarbons. Crit. Rev. Microbiol. 1, 199–223 (1972)
Gibson, D. T.: Biodegradation of aromatic petroleum hydrocarbons. In: Fate and effects of petroleum hydrocarbons (D. A. Wolfe, ed.), pp. 36–46. New York: Pergamon Press 1977
Jeffrey, A. M., Yeh, H. J. C., Jerina, D. M., Patel, T. R., Davey, J. F., Gibson, D. T.: Initial reactions in the oxidation by naphthalene by Pseudomonas putida. Biochemistry 14, 575–584 (1975)
Jerina, D. M., Daly, J. W., Witkop, B., Zaltzman-Nirenberg, P., Udenfriend, S.: Role of arene oxide-oxepin system in the metabolism of aromatic substrates. I. In vitro conversion of benzene oxide to a premercapturic acid and a dihydrodiol. Arch. Biochem. Biophys. 128, 176–183 (1968a)
Jerina, D. M., Daly, J. W., Witkop, B., Zaltzman-Nirenberg, P., Udenfriend, S.: 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. J. Am. Chem. Soc. 90, 6525–6527 (1968b)
Jerina, D. M., Daly, J. W., Witkop, B., Zaltzman-Nirenberg, P.: Udenfriend, S.: 1,2-Naphthalene oxide as an intermediate in the microsomal hydroxylation of naphthalene. Biochemistry 9, 147–156 (1970)
Jerina, D. M., Daly, J. W., Jeffrey, A. M., Gibson, D. T.: cis-1,2-Dihydroxy-1,2-dihydronaphthalene: a bacterial metabolite from naphthalene. Arch. Biochem. Biophys. 142, 394–396 (1971)
Jerina, D. M., Daly, J. W.: Arene oxides: a new aspect of drug metabolism. Science 185, 573–582 (1974)
Lebeault, J. M., Lode, E. T., Coon, M. J.: Fatty acid and hydrocarbon hydroxylation in yeast: Role of cytochrome P-450 in Candida tropicalis. Biochem. Biophys. Res. Commun. 42, 413–419 (1971)
Machlis, L.: Growth and nutrition of water molds in the sub-genus Euallomyces. II. Optimal composition of the minimal medium. Am. J. Bot. 40, 450–460 (1953)
Murphy, G., Vogel, G., Krippahl, G., Lynen, F.: Patulin biosynthesis: The role of mixed function oxidases in the hydroxylation of m-cresol. Eur. J. Biochem. 49, 443–455 (1974)
Oesch, F., Jerina, D. M., Daly, J. W.: Conversion of naphthalene to trans-naphthalene dihydrodiol: Evidence for the presence of a coupled aryl monooxygenase-epoxide hydrase system in hepatic microsomes. Biochem. Biophys. Res. Commun. 46, 1713–1720 (1971)
Oesch, F., Jerina, D. M., Daly, J. W., Lu, A. Y. H., Kuntzman, R., Conney, A. H.: A reconstituted microsomal enzyme system that converts naphthalene to trans-1,2-dihydroxy-1,2-dihydronaphthalene via naphthalene-1,2-oxide: Presence of epoxide hydrase in cytochrome P-450 and P-448 fractions. Arch. Biochem. Biophys. 153, 62–67 (1972)
Oesch, F.: Mammalian epoxide hydrases: Inducible enzymes catalyzing the inactivation of carinogenic metabolites derived from aromatic and olefinic compounds. Xenobiotica 3, 305–340 (1973)
Smith, R. V., Rosazza, J. P.: Microbial models of mammalian metabolism. Aromatic hydroxylation. Arch. Biochem. Biophys. 161, 551–558 (1974)
Stanier, R. Y., Ornston, L. N.: The β-ketoadipate pathway. Adv. Microbial Physiol. 9, 89–151 (1973)
Wiseman, A., Gondal, J. A., Sims, P.: 4′-Hydroxylation of biphenyl by yeast containing cytochrome P-450: Radiation and thermal stability, comparisons with liver enzyme (oxidized and reduced forms). Biochem. Soc. Trans. 3, 278–281 (1975)
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Cerniglia, C.E., Hebert, R.L., Szaniszlo, P.J. et al. Fungal transformation of naphthalene. Arch. Microbiol. 117, 135–143 (1978). https://doi.org/10.1007/BF00402301
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00402301