Abstract
The aquatic hyphomycete Heliscus lugdunensis belongs to a group of exclusively aquatic mitosporic fungi with an only scarcely explored potential to oxidatively attack xenobiotic compounds, and was used to study the biotransformation of the environmental pollutant metabolite 1-naphthol. H. lugdunensis metabolized approximately 74% of 1-naphthol within 5 days. The identification and quantification of degradation products using gas chromatography-mass spectrometry, liquid chromatography-mass spectrometry, and high performance liquid chromatography revealed that approximately 12% of the parent compound was converted into 1-naphthylsulfate, 3% was transformed into 1-methoxy-naphthalene, and less than 1% was converted into 1,4-naphthoquinone. A further metabolite, most likely 4-hydroxy-1-naphthylsulfate, was also detected. In contrast to sulfate conjugate metabolites, no glucuronide and glucoside conjugates of 1-naphthol were found, and neither UDP-glucuronyltransferase nor UDP-glucosyltransferase present in H. lugdunensis showed activity towards 1-naphthol. These results support a role of fungi adapted to aquatic environments in affecting the environmental fate of pollutants in aquatic ecosystems.
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Literature Cited
Allen CCR, Boyd DR, Larkin MJ, Reid KA, Sharma ND, Wilson K (1997) Metabolism of naphthalene, 1-naphthol, indene, and indole by Rhodococcus sp. strain NCIMB 12038. Appl Environ Microbiol 63:151–155
Bärlocher F (1992) The ecology of aquatic hyphomycetes. Berlin: Springer-Verlag
Boss B, Richling E, Herderich M, Schreier P (1999) HPLC-ESI-MS/MS analysis of sulfated flavour compounds in plants. Phytochemistry 50:19–225
Cerniglia CE, Sutherland JB, Crow SA (1992) Fungal metabolism of aromatic hydrocarbons. In: Winkelmann G (ed) Microbial degradation of natural products. Weinheim: Wiley-VCH, pp 193–217
Da Silva M, Esposito E, Moody JD, Canhos VP, Cerniglia CE (2004) Metabolism of aromatic hydrocarbons by the filamentous fungus Cyclothyrium sp. Chemosphere 57:943–952
Dalton SA, Smith KA (1971) DDT and river fungi. Trans Br Mycol Soc 58(suppl):28
Dikshith TS, Kumar SN, Raizada RB, Srivastava MK, Ray PK (1990) Residues of 1-naphthol in soil and waters amples in and around Bophal, India. Bull Environ Contam Toxicol 44:87–91
Gosselin H, Hodge C, Smith RP, Gleason MN (1976) Clinical toxicology of commercial products. Baltimore: Williams & Wilkins
Hayatsu M, Hirano M, Nagata T (1999) Involvement of two plasmids in the degradation of carbaryl by Arthrobacter sp. strain RC100. Appl Environ Microbiol 65:1015–1019
Heitkamp MA, Freeman JP, Cerniglia CE (1987) Naphthalene biodegradation in environmental microcosms: estimates of degradation rates and characterization of metabolites. Appl Environ Microbiol 53:129–136
Johnsen AR, Wick LY, Harms H (2005) Principles of microbial PAH-degradation in soil. Environ Pollut 133:71–84
Junghanns C, Moeder M, Krauss G, Martin C, Schlosser D (2005) Degradation of the xenoestrogen nonylphenol by aquatic fungi and their laccases. Microbiology 151:45–57
Krauss G, Bärlocher F, Krauss G-J (2003) Effect of pollution on aquatic hyphomycetes. In: Tsui CKM, Hyde KD (eds) Freshwater mycology. Fungal diversity research series 10. Hong Kong: Fungal Diversity Press, pp 211–230
Krauss G, Bärlocher F, Wennrich R, Glässer W, Krauss G-J (2001) Aquatic hyphomycetes occur in hyperpolluted waters in Central Germany. Nova Hedwigia 72:419–428
Krauss G, Schlosser D, Krauss G-J (2005) Aquatic fungi in heavy metal and organically polluted habitats. In: Deshmukh SK, Rai MK (eds) Biodiversity of fungi: Their role in human life. New Dehli: Oxford & IBH Publishing Co Pvt Ltd, and Enfield: Science Publishers, pp 221–246
Lange B, Kremer S, Sterner O, Anke H (1994) Pyrene metabolism in Crinipellis stipitaria: identification of trans-dihydro-4,5-dihydroxypyrene and 1-pyrenylsulfate in strain JK364. Appl Environ Microbiol 60:3602–3606
Larson SJ, Capel PD, Majewski MS (1997) Pesticides in surface waters: distribution, trends, and governing factors. Chelsea: Ann Arbor Press
Lowry DH, Rosenbrough NJ, Farr AL, Randell RL (1951) Protein measurement with Folin phenol reagent. J Biol Chem 193:265–275
Sack U, Heinze TM, Deck J, Cerniglia CE, Cazau MC, Fritsche W (1997) Novel metabolites in phenanthrene and pyrene transformation by Aspergillus niger. Appl Environ Microbiol 63:2906–2909
Samanta SK, Chakraborti AK, Jain RK (1999) Degradation of phenanthrene by different bacteria: evidence for novel transformation sequences involving the formation of 1-naphthol. Appl Microbiol Biotechnol 53:98–107
Watanabe HK, Hoskins B, Ho IK (1986) Selective inhibitory effect of organophosphates on UDP-glucuronyltransferase activities in rat liver microsomes. Biochem Pharmacol 35:455–460
Wunder T, Marr J, Kremer S, Sterner O, Anke H (1997) 1-Methoxypyrene and 1,6-dimethoxypyrene: two novel metabolites in fungal metabolism of polycyclic aromatic hydrocarbons. Arch Microbiol 167:310–316
Zhang D, Yang Y, Leakey JEA, Cerniglia CE (1996) Phase I and phase II enzymes produced by Cunninghamella elegans for the metabolism of xenobiotics. FEMS Microbiol Lett 138:221–226
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We thank C. Kuhnt (Halle) for performing the GC-MS measurements.
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Augustin, T., Schlosser, D., Baumbach, R. et al. Biotransformation of 1-Naphthol by a Strictly Aquatic Fungus. Curr Microbiol 52, 216–220 (2006). https://doi.org/10.1007/s00284-005-0239-z
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DOI: https://doi.org/10.1007/s00284-005-0239-z