Abstract
For elucidation of the metabolism of the endocrine disruptor nonylphenol by Sphingomonas sp. strain TTNP3, the degradation of an isomer of nonylphenol, 4(2′,6′-dimethyl-2′-heptyl)-phenol, has been studied. As in the case of 4(3′,5′-dimethyl-3′-heptyl)-phenol, the metabolism of this nonylphenol isomer leads to the formation of the NIH-shifted product 2(2′,6′-dimethyl-2′-heptyl)-1,4-benzenediol (NIH: National Institute of Health), but also to the alkoxy derivative 4(2′,6′-dimethylheptan-2′-yloxy)phenol as additional metabolite. To the best of our knowledge, this is the first report describing the formation of alkoxyphenol as a degradation product of nonylphenol. Additionally, these results provide for the first time evidence for slight differences in the biodegradation of the isomers of nonylphenol.
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Corvini PFX, Vinken R, Hommes G, Schmidt B, Dohmann M (2004a) Degradation of the radioactive and non-labelled branched 4(3′,5′-dimethyl-3′-heptyl)-phenol nonylphenol isomer by Sphingomonas TTNP3. Biodegradation 15:9–18
Corvini PFX, Vinken R, Hommes G, Mundt M, Meesters R, Schröder HF, Hollender J, Schmidt B (2004b) Microbial degradation of a single branched isomer of nonylphenol by Sphingomonas TTNP3. Water Sci Technol 50(5):195–202
Corvini PFX, Meesters R, Schäffer A, Schröder HF, Vinken R, Hollender J (2004c) Degradation of a nonylphenol single isomer by Sphingomonas sp. strain TTNP3 leads to a hydroxylation-induced migration product. Appl Environ Microbiol 70:6897–6900
Giger W, Ahel M, Koch M, Laubscher HU, Schaffner C, Schneider J (1987) Behaviour of alkylphenolpolyethoxylate surfactants and of nitrilotriacetate in sewage treatment. Water Sci Technol 19:449–460
Soto AM, Justica H, Wray JW, Sonnenschein C (1991) Para-nonylphenol: an estrogenic xenobiotic released from polystyrene. Environ Health Perspect 92:167–173
Van Ginkel CG (1996) Complete degradation of xenobiotic surfactants by consortia of aerobic microorganisms. Biodegradation 7:151–164
Vinken R, Schmidt B, Schäffer A (2002) Synthesis of tertiary 14C-labelled nonylphenol isomers. J Label Compd Radiopharm 45:1253–1263
Vinken R, Höllrigl-Rosta A, Schmidt B, Schäffer A, Corvini PFX (2004) Bioavailability of a nonylphenol isomer in dependence on the association to dissolved humic substances. Water Sci Technol 50(5):285–291
Wheeler TF, Heim JR, LaTorre MR, Janes B (1997) Mass spectral characterization of p-nonylphenol isomers using high-resolution capillary GC–MS. J Chromatogr Sci 35:19–30
Ying GG, Kookana RS, Dillon P (2003) Sorption and degradation of selected five endocrine disrupting chemicals in aquifer material. Water Res 37:3785–3791
Acknowledgements
We thank Prof. W. Verstraete and Dr. N. Boon (LabMet, University Ghent, Belgium) for the S. TTNP3 strain. The assistance of M. Meindorf is gratefully acknowledged.
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Corvini, P.F.X., Elend, M., Hollender, J. et al. Metabolism of a nonylphenol isomer by Sphingomonas sp. strain TTNP3. Environ Chem Lett 2, 185–189 (2005). https://doi.org/10.1007/s10311-004-0094-3
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DOI: https://doi.org/10.1007/s10311-004-0094-3