Abstract
Six yeasts were examined for their ability to metabolize naphthalene, biphenyl and benzo(a)pyrene. All of the organisms tested oxidized these aromatic hydrocarbons. Candida lipolytica oxidized naphthalene to 1-naphthol, 2-naphthol, 4-hydroxy-1-tetralone and trans-1,2-dihydroxy-1,2-dihydronaphthalene. The major metabolite was 1-naphthol. C. lipolytica oxidized biphenyl to produce 2-, 3-, and 4-hydroxybiphenyl, 4,4′-dihydroxybiphenyl and 3-methoxy-4-hydroxybiphenyl. 4-Hydroxybiphenyl was the predominant metabolite formed. C. lipolytica oxidized benzo(a)pyrene to 3-hydroxybenzo(a)pyrene and 9-hydroxybenzo(a)pyrene. Metabolites were isolated and identified by absorption spectrophotometry, mass spectrometry and thin-layer, gasliquid and high-pressure liquid chromatography. Where possible the structures of these metabolites were confirmed by comparison with authenic compounds.
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Abbreviations
- tlc:
-
thin-layer chromatography
- hplc:
-
high pressure liquid chromatography and
- GC/MS:
-
Gas chromatography-mass spectrometry
- TMS:
-
Trimethylsilyl
- YNBG:
-
yeast nitrogen base glucose
References
Ahearn DG, Meyers SP, Standard PG (1971) The role of yeasts in the decomposition of oils in marine environments. Dev Ind Microbiol 12:126–134
Ahearn DG, Crow SA, Berner NH, Meyers SP (1976) Microbiological cycling of oil in estuarine marsh lands. In: Wiley M (ed) Estuarine Processes I. Academic Press, New York, pp 483–493
Atlas RM, Schofield EA, Morellia FA, Cameron RE (1976) Effects of petroleum pollutants on Artic microbial populations. Environ Pollut 10:35–43
Billings RE, McMahon RE (1978) Microsomal biphenyl hydroxylation: the formation of 3-hydroxybiphenyl and biphenyl catechol. Mol Pharmacol 14:145–154
Blumer M (1976) Polycyclic aromatic hydrocarbons in nature. Sci Am 234:34–44
Bollag JM, Czaplicki EJ, Minard RD (1975) Bacterial metabolism of 1-naphthol. Agric Food Chem 23:85–90
Cerniglia CE, Gibson DT (1977) Metabolism of naphthalene by Cunninghamella elegans. Appl Environ Microbiol 34:363–370
Cerniglia CE, Gibson DT (1978) Metabolism of naphthalene by cell extracts of Cunninghamella elegans. Arch Biochem Biophys 186:121–127
Cerniglia CE, Hebert RL, Szaniszlo PJ, Gibson DT (1978) Fungal transformation of naphthalene. Arch Microbiol 117:135–143
Cerniglia CE, Gibson DT (1979) Oxidation of benzo(a)pyrene by the filamentous fungus Cunninghamella elegans. J Biol Chem 254:12174–12180
Cerniglia CE, Gibson DT (1980) Fungal oxidation of benzo(a)pyrene: Evidence for the formation of a benzo(a)pyrene 7,8-diol-9,10 epoxide. J Biol Chem 255:5159–5163
Cerniglia CE, Gibson DT, Van Baalen C (1980) Oxidation of naphthalene by the cyanobacterium Oscillatoria sp. strain JCM. J Gen Microbiol 125:203–207
Dagley S (1971) Catabolism of aromatic compounds by microorganisms. Adv Microbiol Physiol 6:1–46
Daly JW, Jerina DM, Witkop B (1972) Arene oxides and the NIH shift: The metabolism, toxicity and carcinogenicity of aromatic compounds. Experientia 28:1129–1149
Dodge RH, Cerniglia CE, Gibson DT (1979) Fungal metabolism of biphenyl. Biochem J 178:223–230
Ferris JP, Fasco MJ, Stylianopoulou FL, Jerina DM, Daly JW, Jeffrey AM (1973) Mono-oxygenase activity in Cunninghamella bainieri. Evidence for a fungal system similar to liver microsomes. Arch Biochem Biophys 156:97–103
Ferris JP, MacDonald LH, Patrie MA, Martin MA (1976) Aryl hydrocarbon hydroxylase activity in the fungus Cunninghamella bainieri: Evidence for the presence of cytochrome P-450. Arch Biochem Biophys 175:443–452
Gibson DT (1972) The microbial oxidation of aromatic hydrocarbons. Crit Rev Microbiol 1:199–223
Gibson DT (1972) Biodegradation of aromatic petroleum hydrocarbons. In: Wolfe DA (ed) Fate and Effects of Petroleum Hydrocarbons. Pergamon Press, New York, pp 36–46
Halpaap K, Horning MG, Horning EC (1978) Metabolism of biphenyl in the rat. J Chromatogr 166:479–490
Jerina DM, Daly JW, 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
Klug MJ, Markovetz AJ (1971) Utilization of aliphatic hydrocarbons by microorganisms. In: Rose AH, Wilkinson JF (eds) Advances in Microbial Physiology Vol. 5. Academic Press, New York, pp 1–43
Meyer T, Aarbakke J, Scheline RR (1976) The metabolism of biphenyl. I. Metabolic disposition of 14C-biphenyl in the rat. Acta Pharmacol Toxicol 39:412–418
Miller EC, Miller JA (1974) Biochemical mechanisms of chemical carcinogenesis. In: Bush H (ed) Molecular Biology of Cancer. Academic Press, New York, pp 377–402
Norkrans B (1966) On the occurrence of yeasts in an estuary of the Swedish west coast. Svensk Bot Tidskr 60:463–482
Oesch F, Jerina DM, Daly JW (1971) Conversion of naphthalene to transnaphthalene dihydrodiol: Evidence for the presence of a coupled aryl mono-oxygenase-epoxide hydrase system in hepatic microsomes. Biochem Biophys Res Commun 46:1713–1720
Servé MP, Jerina DM (1978) Synthesis of biphenyl 2,3-oxide. J Org Chem 43:2711–2713
Shennan JL, Levi JD (1974) The growth of yeasts on hydrocarbons. In: Progress in Industrial Microbiology. Churchill Livingstone, London, pp 1–57
Wiseman A, Gondal JA, Sims P (1975) 4′-Hydroxylation of biphenyl by yeast containing cytochrome P-450: Radiation and thermal stability, comparisons with liver enzymes (oxidized and reduced forms). Biochem Soc Trans 3:278–281
Wiseman A, Woods LFJ (1979) Benzo(a)pyrene metabolites formed by the action of yeast cytochrome P-450/P-448. J Chem Tech Biotechnol 29:320–324
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Cerniglia, C.E., Crow, S.A. Metabolism of aromatic hydrocarbons by yeasts. Arch. Microbiol. 129, 9–13 (1981). https://doi.org/10.1007/BF00417170
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DOI: https://doi.org/10.1007/BF00417170