Degradation of alkylphenol ethoxylates by Pseudomonas sp. strain TR01

Maki, Hideshi; Masuda, Nobuhito; Fujiwara, Yoshiyuki; Ike, Michihiko; Fujita, Masanori

doi:10.1128/aem.60.7.2265-2271.1994

Cited by 70 publications

(33 citation statements)

References 31 publications

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“…Pseudomonas synxantha, mephitica, and fluorescens were strongly present during surfactant dosing, suggesting that such microorganisms could probably degrade Triton X‐100. This is in agreement with the literature; in fact, a strain of Pseudomonas that is capable of demolishing polyethoxylate nonylphenol into a diethoxylate has been isolated ( Allen et al, 1999 ; Maki et al, 1994 ).…”

Section: Resultssupporting

confidence: 92%

Alkylphenol Polyethoxylate Removal in a Pilot‐Scale Reed Bed and Phenotypic Characterization of the Aerobic Heterotrophic Community

Sacco¹,

Pizzo²,

E³

et al. 2006

Water Environment Research

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ABSTRACT:The removal of the non-ionic surfactant Triton X-100, dosed at 30 and 300 mg/L in a pilot-scale subsurface horizontal flow reed bed, and the aerobic heterotrophic cultivable community associated with the roots and with the substrate gravel in both absence and presence of Triton X-100 were investigated. t-Octylphenol (OP) and its mono-, di-and tri-ethoxyl derivatives, among others, were found in the outlet. A mass balance allowed us to calculate that approximately 40% of the Triton X-100 metabolites OP and octylphenol polyethoxylate derivatives flowed out of the reed bed during the dosage and postdosage experiments. More aerobic heterotrophic microorganisms adhered to the roots than to the gravel. The appearance of new strains (Aeromonas, Flavobacterium, and Aquaspirillum) and the increased presence of others (Pseudomonas) during the dosage of Triton may be linked to the capacity of these bacteria to adapt to the presence of the surfactant or to use it as a nourishment. Water Environ. Res., 78, 000 (2006).

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Section: Resultssupporting

confidence: 92%

Alkylphenol Polyethoxylate Removal in a Pilot‐Scale Reed Bed and Phenotypic Characterization of the Aerobic Heterotrophic Community

Sacco¹,

Pizzo²,

E³

et al. 2006

Water Environment Research

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“…1. However, the final profile of homologue distribution was similar in both tests (accumulation of NPPOs with one to six propoxylene units was observed in both cases) This scheme is similar to that observed in biodegradation tests of APEOs where lower molecular mass homologues having one to three ethoxylene units were accumulated [12,15,24]. The difference in alkoxylene chain lengths of NPPOs and APEOs being accumulated in the biodegradation liquor can be connected with the lower polarity of propoxylene units compared with ethoxylene units.…”

Section: Resultssupporting

confidence: 82%

“…Moreover, alkylphenols have been known for several years as hazardous pollutants with endocrine disruption activity [9][10][11]. Many biodegradation studies on APEOs have been carried out [12][13][14][15][16][17][18], while only one study concerning the biodegradation of APPOs is available [19]. Most studies on APEOs have proved that biodegradation of these surfactants occurs by shortening the ethoxylene chain, which leads to accumulation of alkylphenols and APEOs containing one, two or three ethoxylene units in the environment [5,[20][21][22][23][24][25][26][27][28].…”

Section: Introductionmentioning

confidence: 99%

Comparison of Biodegradation of Nonylphenol Propoxylates with Usage of Two Different Sources of Activated Sludge

Zgoła‐Grześkowiak

Grześkowiak

Szymański

2013

J Surfact & Detergents

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Aerobic biodegradation behaviour of nonylphenol propoxylates was investigated in two tests with different sewage sludge as inocula. The samples containing target compounds were pre-concentrated using dispersive liquid–liquid microextraction and analysed with the use of high performance liquid chromatography with tandem mass spectrometry. Both primary biodegradation and formation of different biodegradation by-products were studied. Primary biodegradation of nonylphenol propoxylates was relatively slow and reached only about 70 % in over 70 days from the start of the tests. The biodegradation by-products from both oxidative and non-oxidative pathways were found. In the non-oxidative route, shortening of the propoxy chain was observed. In the oxidative pathway carboxylic acids and ketones were identified. The biodegradation by-products identified with the use of mass spectrometric detection also persisted for many days.

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“…The sequential exoscission of glycol units from NPEO x is consistent with the study of Kveštak and Ahel (20), who showed the formation of shortened but unoxidized NPEO x homologs by mixed estuarine cultures. On the other hand, some workers (4,24) have interpreted the frequent occurrence of oxidized intermediates (carboxylic acid analogs) in mixed culture and environmental samples as indicative of the importance of oxidative mechanisms in NPEO x biodegradation. A parallel situation exists in the biodegradation of polyethylene glycols, for which there is evidence for their oxidation to carboxylic acids but no evidence on which to assess whether oxidation is a precursor to, or a component of, the ether scission step (38).…”

Section: Gc-ms Analysis Of End Product Of Biodegradation Of Npeo Av9mentioning

confidence: 99%

“…Laboratory studies with mixed cultures (20,23,31) and pure cultures (15,24,26) have demonstrated that biodegradation results in the conversion of NPEO x to shorter homologs, usually nonylphenol diethoxylate (NPEO 2 ) and/or its carboxylic acid analog, and it has been tacitly assumed that this is achieved by sequential removal of C 2 ethoxylate units from the end of the chain. However, definitive evidence for the operation of this pathway in pure culture is lacking, and the nature of the ether scission reaction which it requires is unknown.…”

mentioning

confidence: 99%

Mechanism for Biotransformation of Nonylphenol Polyethoxylates to Xenoestrogens in Pseudomonas putida

1998

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A strain of Pseudomonas putida isolated from activated sewage grew aerobically on the xenoestrogen precursor, nonylphenol polyethoxylate (NPEO x , 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 NPEO x . Biodegradation kinetics measured by high-pressure liquid chromatography (HPLC) for each component in NPEO x 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 NPEO x -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 NPEO x and dissociation of the resulting hemiacetal to release acetaldehyde and the next-lower homolog, NPEO x−1, which then undergoes further cycles of the same reaction until x = 2.

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Degradation of alkylphenol ethoxylates by Pseudomonas sp. strain TR01

Cited by 70 publications

References 31 publications

Alkylphenol Polyethoxylate Removal in a Pilot‐Scale Reed Bed and Phenotypic Characterization of the Aerobic Heterotrophic Community

Alkylphenol Polyethoxylate Removal in a Pilot‐Scale Reed Bed and Phenotypic Characterization of the Aerobic Heterotrophic Community

Comparison of Biodegradation of Nonylphenol Propoxylates with Usage of Two Different Sources of Activated Sludge

Mechanism for Biotransformation of Nonylphenol Polyethoxylates to Xenoestrogens in Pseudomonas putida

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