Ensifer sp. strain AS08 and Pseudomonas sp. strain AS90 degrading short ethoxy (EO) chain-nonylphenol (NP) [NPEOav2.0 containing NP mono- ∼ tetraethoxylates (NP1EO ∼ NP4EO); average 2.0 EO units] were isolated by enrichment cultures. Both strains grew on NP but not on octyl- and nonylphenol polyethoxylates (NPEOs) (average 10 EO units). Growth and degradation of NPEOav2.0 was increased with increased concentrations of yeast extract (0.02–0.5%) in a culture medium. Culture supernatants of both strains grown on NPEOav2.0 were analyzed by high-performance liquid chromatography, showing degradation of NP4EO–NP1EO. The metabolites from nonylphenol diethoxylate (NP2EO) by resting cells of both strains were identified by gas chromatography–mass spectrometry as nonylphenoxyethoxyacetic acid, NP1EO, nonylphenoxyacetic acid (NP1EC), and NP, while those from NP1EO were identified as NP1EC and NP. Cell-free extracts from strain AS08 grown on NPEOav2.0 dehydrogenated NPEOs, NPEOav2.0, NP2EO, NP1EO, and PEG 400, but the extracts were inactive toward di- ∼ tetraethylene glycol. Aldehydes were formed in the reaction mixture of each substrate with cell-free extracts. From these results, the aerobic metabolic pathway for short EO chain-NP is proposed: A terminal alcohol group of the EO chain is oxidized to a carboxylic acid via an aldehyde, and then one EO unit is removed. This process is repeated until NP is produced.
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Ahel M, Conrad T, Giger W (1987) Persistent organic chemicals in sewage effluents. 3. Determinations of nonylphenoxy carboxylic acids by high-resolution gas chromatography/mass spectrometry and high-performance liquid chromatography. Environ Sci Technol 21:697–703
Ejlertsson J, Nilsson ML, Kylin H, Bergman A, Karlson I, Oquist M, Svensson BH (1999) Anaerobic degradation of nonylphenol mono- and diethoxylates in digestor sludge, landfill municipal solid waste and landfill sludge. Environ Sci Technol 33:301–306
Frings J, Schramm Z, Schink B (1992) Enzymes involved in anaerobic polyethylene glycol degradation by Pelobacter venetianus and Bacteroides strain PG1. Appl Environ Microbiol 58:2164–2167
Fujii K, Urano N, Ushio H, Satomi M, Iida H, Ushio-Sata N, Kimura S (2000) Profile of a nonylphenol-degrading microflora and its potential for bioremedial applications. J Biochem 128:909–916
Giger W, Brunner PH, Schaffner C (1984) 4-Nonylphenol in sewage sludge: accumulation of toxic metabolites from nonionic surfactants. Science 225:623–625
Hayashi S, Saito S, Kim J-H, Nishimura O, Sudo R (2005) Aerobic biodegradation behavior of nonylphenol polyethoxylates and their metabolites in the presence of organic matter. Environ Sci Technol 39:5626–5633
Jobling R, Sumpter JP (1993) Detergent components in sewage effluent are weakly estrogenic to fish: an in vitro study using rainbow trout (Oncorhynchus mykiss) hepatocytes. Aquat Toxicol 27:361–372
John DM, White GF (1998) Mechanism for biotransformation of nonylphenol polyethoxylates to xenoestrogens in Pseudomonas putida. J Bacteriol 180:4332–4338
Jonkers N, Knepper TP, de Voogt P (2001) Aerobic biodegradation studies of nonylphenol ethoxylates in river water using liquid chromatography–electrospray tandem mass spectrometry. Environ Sci Technol 35:335–340
Jonkers N, Laane RW, de Voogt P (2003) Fate of nonylphenol ethoxylates and their metabolites in two Dutch estuaries: evidence of biodegradation in the field. Environ Sci Technol 37:321–327
Kane MD, Poulsen LK, Stahl DA (1993) Monitoring the enrichment and isolation of sulfate-reducing bacteria by using oligonucleotide hybridization probes designed from environmentally derived 16S rRNA sequences. Appl Environ Microbiol 59:682–686
Kawai F, Fukaya M, Tani Y, Ogata K (1977) Identification of polyethylene glycols (PEGs)-assimilable bacteria and culture characteristics of PEG 6000 degradation by a mixed culture. J Ferment Technol 55:429–435
Kawai F, Kimura T, Tani Y, Yamada H, Ueno T, Fukami H (1983) Identification of reaction products of polyethylene glycol dehydrogenase. Agric Biol Chem 47:1669–1671
Kvestak R, Ahel M (1994) Occurrence of toxic metabolites from nonionic surfactants in the Krka River estuary. Ecotoxicol Environ Saf 28:25–34
Liu X, Tani A, Kawai F (2005) Determination of nonylphenol and short chain nonylphenol polyethoxylates by normal phase high performance liquid chromatography. Chin J Anal Chem 33:1189–1191
Maeda S, Mikami I (1988) Degradation of the non-ionic surfactant (polyoxyethylene-p-nonylphenyl ether) by Pseudomonas species. J Water Wastes 30:1056–1063
Maki H, Masuda N, Fujiwara Y, Ike M, Fujita M (1994) Degradation of alkylphenol ethoxylates by Pseudomonas sp. strain TR01. Appl Environ Microbiol 60:2265–2271
Montgomery-Brown J, Drewes JE, Fox P, Reinhard M (2003) Behavior of alkylphenol polyethoxylate metabolites during soil aquifer treatment. Water Res 37:3672–3681
Murray ERB, Doetsch RN, Robinow CF (1994) Determinative and cytological light microscopy. In: Gerhardt P, Murray ERB, Wood WA, Krieg NR (eds) Methods for general and molecular bacteriology. ASM, Washington, DC, pp 31–32
Patoczka J, Pulliam GW (1990) Biodegradation and secondary effluent toxicity of ethoxylated surfactants. Water Res 24:965–972
Planas C, Guadayol JM, Droguest M, Escals A, Rivera J, Caixach J (2002) Degradation of polyethoxylated nonylphenols in a sewage treatment plant. Quantitative analysis by isotopic dilution-HRGC/MS. Water Res 36:982–988
Sato H, Shibata A, Wang Y, Yoshikawa H, Tamura H (2003) Characterization of biodegradation intermediates of nonionic surfactants by MALDI-MS. 2. Oxidative biodegradation profiles of uniform octylphenol polyethoxylate in 18O-labeled water. Biomacromolecules 4:46–51
Smibert RM, Krieg NR (1994) Phenotypic characterization. In: Gerhardt P, Murray, ERB, Wood WA, Krieg NR (eds) Methods for general and molecular bacteriology. ASM, Washington, DC, pp 615–640
Soto AM, Justicia H, Wray JW, Sonnenschein C (1991) p-Nonylphenol: an estrogenic xenobiotic released from modified polystyrene. Environ Health Persp 92:167–173
Sugimoto M, Tanabe M, Hataya M, Enokibara S, Duine JA, Kawai F (2001) The first step in polyethylene glycol degradation by sphingomonads proceeds via a flavoprotein alcohol dehydrogenase containing flavin adenine dinucleotide. J Bacteriol 183:6694–6698
Thompson JD, Higgins DG, Gibson TJ (1994) Improving the sensitivity of progressive multiple sequence alignment through sequence weighting, position specific gap penalties and weight matrix choice. Nucleic Acids Res 22:4673–4680
Ushida Y, Takahara Y, Ohta H (2003) Sphingobium amiense sp. nov., a novel nonylphenol-degrading bacterium isolated from a river sediment. Inter J Syst Evol Microbiol 53:2045–2048
Wintgens T, Gallenkemper M, Melin T (2003) Occurrence and removal of endocrine disrupters in landfill leachate treatment plants. Water Sci Technol 48:127–134
Yuan SY, Chang JS, Yen J, Chang BV (2000) Biodegradation of phenanthrene in river sediment. Chemosphere 43:273–278
Yuan SY, Yu CH, Chang BV (2004) Biodegradation of nonylphenol in river sediment. Environ Pollut 127:425–430
We are grateful to Dr. M. Hatta, Okayama University of Science, and to Mr. Y. Haba for their help with the GC–MS measurement. This work was partly supported by the Research Grant for Encouragement of Studies to F. K. and X. L. from the Graduate School of Natural Science and Technology, Okayama University. We appreciate the review of the manuscript prior to submission by KN International.
English edition: The paper was edited by a native speaker through KN international (http://www.kninter.com)
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Liu, X., Tani, A., Kimbara, K. et al. Metabolic pathway of xenoestrogenic short ethoxy chain-nonylphenol to nonylphenol by aerobic bacteria, Ensifer sp. strain AS08 and Pseudomonas sp. strain AS90. Appl Microbiol Biotechnol 72, 552–559 (2006). https://doi.org/10.1007/s00253-005-0288-z
- Sewage Sludge
- Nicotinamide Adenine Dinucleotide
- Aerobic Degradation
- Tetraethylene Glycol