Abstract
Trichosporon beigelii SBUG 752 was able to transform diphenyl ether. By TLC, HPLC, GC, GC-MS, NMR- and UV-spectroscopy, several oxidation products were identified. The primary attack was initiated by a monooxygenation step, resulting in the formation of 4-hydroxydiphenyl ether, 2-hydroxydiphenyl ether and 3-hydroxydiphenyl ether (48:47:5). Further oxidation led to 3,4-dihydroxydiphenyl ether. As a characteristic product resulting from the cleavage of an aromatic ring, the lactone of 2-hydroxy-4-phenoxymuconic acid was identified. The possible mechanism of ring cleavage to yield this metabolite is discussed.
Similar content being viewed by others
References
Cerniglia CE & Gibson DT (1977) Metabolism of naphthalene byCunninghamella elegans. Appl. Environ. Microbiol. 10: 363–367
Cerniglia CE, Morgan JC & Gibson DT (1979) Bacterial and fungal oxidation of dibenzofuran. Biochem. J. 180: 175–185
Cerniglia CE (1981) Aromatic hydrocarbons: Metabolism by bacteria, algae and fungi. In: Hodgson E, Bend JR, Philpot RM (Eds) Reviews in Biochemical Toxicology (pp 321–361) Elsevier/North Holland Publishing (o.) New York
Cerniglia CE & Crow SA (1981) Metabolism of aromatic hydrocarbons by yeasts. Arch. Microbiol. 129: 9–13
Daly JW, Jerina DM & Witkop B (1972) Arene oxides and the NIH shift: the metabolism, toxicity and carcinogenicity of aromatic compounds. Experientia 28: 1129–1249
Dodge RH, Cerniglia CE & Gibson DT (1979) Fungal metabolism of biphenyl. Biochem. J. 178: 223–230
Eaton WE & Ribbons DW (1982) Metabolism of dibutylphthalate and phthalate byMicrococcus sp. strain 12 B. J. Bacteriol. 151: 48–57
Eaton WE & Ribbons DW (1987) Biotransformation of 3-methylphthalate byMicrococcus sp. strain 12 B. J. Gen. Microbiol. 133: 2473–2476
Fortnagel P, Harms H, Wittich R-M, Francke W, Krohn S, Meyer H (1989) Cleavage of dibenzofuran and dibenzodioxin ring systems by aPseudomonas bacterium. Naturwiss. 76: 222–223
Gaal A & Neujahr H (1980) cis-cis-Muconate cyclase fromTrichosporon cutaneum. Biochem. J. 191: 37–43
Gurujeyalakshmi G & Mahadevan A (1987) Degradation of gallic acid byAspergillus flavus. Zentralbl. Mikrobiol. 142: 187–192
Hofmann KH & Schauer F (1988) Utilization of phenol by hydrocarbon assimilating yeasts. Antonic van Leeuwenhoek 54: 179–188
Hutzinger O & Blumid MJ (1985) Sources and fate of PCDD's and PCDF's: an overview. Chemosphere 14: 581–600
Janssen DE, van Allan J & Wilson CV (1955) Synthesis of 4-phenoxycatechol and 2-phenoxyhydroquinone. J. Org. Chem. 20: 1326–1329
McLafferty FW & Stauffer DB (1989) The Wiley/NBS registry of mass spectral data. J. Wiley & Sons, New York
Mc Omie JFW & West DE (1969) 3,3′-Dihydroxybiphenyl. Org. Synthesis 49: 50–52
Plüss N, Poiger H, Hohbach C, Suter M & Schlatter C (1988) Subchronic toxicity of 2,3,4,7,8-pentachlorodibenzofuran in rats. Chemosphere 17: 1099–1110
Schauer F, Henning K, Schauer M & Hecker M (1993) Characterization ofTrichosporon beigelii SBUG 752 oxidizing dioxin like compounds (in preparation)
Seigle-Murandi FM, Krivobok SMA, Steiman RL, Benoit-Guyod J-LA & Thiault G-A (1991) Biphenyl oxide hydroxylation byCunninghamella echinulata. J. Agric. Food. Chem. 39: 428–430
Servé MP & Jerina DM (1978) Synthesis of biphenyl-2,3-oxide. J. Org. Chem. 43: 2711–2714
Spanning A & Neujahr HY (1987) Growth and enzyme synthesis during continuous culture ofTrichosporon cutaneum on phenol. Biotechnol. Bioengin. 29: 464–468
Stahl E (1967) Thin layer chromatography. Springer-Verlag Berlin, Heidelberg, New York, 818
Strubel V, Rast HG, Fietz W, Knackmuss H-J & Engesser KH (1989) Enrichment of dibenzofuran utilizing bacteria with high co-metabolic potential towards dibenzodioxin and other anellated aromatics. FEMS Microbiol. Lett. 58: 233–238
Ungnade E & Orwoll EF (1946) 2-Methoxydiphenylether. Org. Synthesis 26: 50–52
Ungnade E & Zilch KT (1950) Phenoxyquinones. J. Org. Chem. 15: 1108–1109
Walker JRL & Taylor BG (1983) Metabolism of phloroglucinol byFusarium solani. Arch. Microbiol. 134: 123–126
Wiseman A, Gondal J & Sims P (1975) 4-Hydroxylation of biphenyl by yeasts containing cytochrome P-450. Biochem. Soc. Trans. 3: 278–285
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Schauer, F., Henning, K., Pscheidl, H. et al. Biotransformation of diphenyl ether by the yeastTrichosporon beigelii SBUG 752. Biodegradation 6, 173–180 (1995). https://doi.org/10.1007/BF00695348
Issue Date:
DOI: https://doi.org/10.1007/BF00695348