ArticleJournal of bacteriology1998
Mechanism for biotransformation of nonylphenol polyethoxylates to Xenoestrogens in Pseudomonas putida.
Article in Journal of bacteriology, 1998. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 17 papers, 1 of them a synthesis that pooled it.
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The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
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Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
Neither the registry nor the abstract names a trial number. If this is a trial report, that itself is worth knowing.
Who cites it
17 citing papers in PubMed, 1 synthesis or guideline pooled it.
- Meta-analysis of environmental contamination by alkylphenols.Environmental science and pollution research international · 2012Pooled it
- Growth and gene expression of Pseudomonas nitroreducens TX1 on octylphenol polyethoxylate surfactants.Applied microbiology and biotechnology · 2025Article
- Bio-Fenton reaction involved in the cleavage of the ethoxylate chain of nonionic surfactants by dihydrolipoamide dehydrogenase from Pseudomonas nitroreducens TX1.Scientific reports · 2019Article
- Comparative Analysis of the Genetic Basis of Branched Nonylphenol Degradation by Sphingobium amiense DSM 16289Microbes and environments · 2018Article
- Transposon Mutagenesis Identifies Genes Critical for Growth of Pseudomonas nitroreducens TX1 on Octylphenol Polyethoxylates.Applied and environmental microbiology · 2016Article
- Isolation and characterization of Sphingomonas sp. Y2 capable of high-efficiency degradation of nonylphenol polyethoxylates in wastewater.Environmental science and pollution research international · 2016Article
- Attention Deficit/Hyperactivity Disorder and Urinary Nonylphenol Levels: A Case-Control Study in Taiwanese Children.PloS one · 2016Article
- Degradation pathways of low-ethoxylated nonylphenols by isolated bacteria using an improved method.Environmental science and pollution research international · 2014Article
- Study of contaminant transport at an open-tipping waste disposal site.Environmental science and pollution research international · 2013Article
- Alkylphenolic compounds and bisphenol A contamination within a heavily urbanized area: case study of Paris.Environmental science and pollution research international · 2013Article
- Overview of passive Chemcatcher sampling with SPE pretreatment suitable for the analysis of NPEOs and NPs.Environmental science and pollution research international · 2013Review
- Biodegradation of polyethoxylated nonylphenols.ISRN microbiology · 2013Article
- Identification and characterization of a novel estrogenic ligand actinopolymorphol A.Biochemical pharmacology · 2010Article
- Monitoring the effects of chiral pharmaceuticals on aquatic microorganisms by metabolic fingerprinting.Applied and environmental microbiology · 2010Article
- Degradation of low-ethoxylated nonylphenols by a Stenotrophomonas strain and development of new phylogenetic probes for Stenotrophomonas spp. detection.Current microbiology · 2006Article
- Degradation of estrogens by Rhodococcus zopfii and Rhodococcus equi isolates from activated sludge in wastewater treatment plants.Applied and environmental microbiology · 2004Article
- Isolation of a bacterial strain able to degrade branched nonylphenol.Applied and environmental microbiology · 1999Article
Corrections and comments
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Authors and funding
2 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
A strain of Pseudomonas putida isolated from activated sewage grew aerobically on the xenoestrogen precursor, nonylphenol polyethoxylate (NPEOx, where x is the number of ethoxylate units) as sole carbon source. Comparative growth yields on NPEOav6, NPEOav9, and NPEOav20 (mixtures with average ethoxylate numbers as indicated) were consistent with utilization of all but two ethoxylate units, and the final accumulating metabolite was identified by gas chromatography-mass spectroscopy as nonylphenol diethoxylate (NPEO2). There was no growth on nonylphenol or polyethylene glycols, and there was no evidence for production of carboxylic acid analogs of NPEOx. Biodegradation kinetics measured by high-pressure liquid chromatography (HPLC) for each component in NPEOx mixtures showed that biodegradation proceeded via successive exoscission of the ethoxylate chain and not by direct scission between the second and third ethoxylate residues. The NPEOx-degrading activity was inducible by substrate, and cell extracts of NPEOav9-induced cells were also active on the pure alcohol ethoxylate, dodecyl octaethoxylate (AEO8), producing sequentially, under either aerobic or anaerobic conditions, AEO7, AEO6, AEO5, etc., thus demonstrating that the pathway involved removal of single ethoxylate units. HPLC analysis of 2,4-dinitrophenylhydrazone derivatives revealed acetaldehyde (ethanal) as the sole aldehydic product from either NPEOav9 or AEO8 under either aerobic or anaerobic conditions. We propose a mechanism for biotransformation which involves an oxygen-independent hydroxyl shift from the terminal to the penultimate carbon of the terminal ethoxylate unit of NPEOx and dissociation of the resulting hemiacetal to release acetaldehyde and the next-lower homolog, NPEOx-1, which then undergoes further cycles of the same reaction until x = 2.
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