Contribution to the detection and identification of oxidation metabolites of nonylphenol in Sphingomonas sp. strain TTNP3

Biodegradation

Volumn 18, Issue 2, 2007, Pages 233-245

  Corvini, P F X ^a   Meesters, R ^a   Mundt, M ^c   Schaffer A ^a   Schmidt, B ^a   Schroder H Fr ^a   Verstraete, W ^b   Vinken, R ^a   Hollender, J ^c  

^a RWTH AACHEN UNIVERSITY   (Germany)

^b GHENT UNIVERSITY   (Belgium)

^c UNIVERSITY HOSPITAL RWTH AACHEN   (Germany)

Author keywords

4(3 ,5 Dimethyl 3 heptyl) phenol; Branched isomer; Metabolites; Nonylphenol; Oxidation; Sphingomonas

Indexed keywords

BACTERIA; CELLS; GROWTH KINETICS; ISOMERS; OXIDATION; PHENOLS;

BRANCHED ISOMERS; SPHINGOMONAS;

METABOLITES;

NONYLPHENOL; PHENOL DERIVATIVE;

BACTERIA; CELLS; GROWTH KINETICS; ISOMERS; METABOLITES; OXIDATION; PHENOLS;

BACTERIUM; BIODEGRADATION; BIOREMEDIATION; DETECTION METHOD; IDENTIFICATION METHOD; METABOLITE; OXIDATION; PHENOL;

ARTICLE; CHEMISTRY; ELECTROSPRAY MASS SPECTROMETRY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; INFRARED SPECTROSCOPY; MASS FRAGMENTOGRAPHY; METABOLISM; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION REDUCTION REACTION; SPHINGOMONAS; STEREOISOMERISM;

CHROMATOGRAPHY, HIGH PRESSURE LIQUID; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION-REDUCTION; PHENOLS; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; SPHINGOMONAS; STEREOISOMERISM;

BACTERIA (MICROORGANISMS); SPHINGOMONAS; SPHINGOMONAS SP.;

EID: 33847674919     PISSN: 09239820     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10532-006-9058-6     Document Type: Article

References (32)

1. Bokern M, Nimtz M, Harms HH (1996) Metabolites of 4- n-nonylphenol in wheat cell suspension cultures. J Agric Food Chem 44:1123-1127
2. Corti A, Frassinetti S, Vallini G, D'Antone S, Fichi C, Solaro R (1995) Biotransformation of nonionic surfactants. I. Biotransformation of 4-(1-nonyl)phenol by Candida maltosa isolate. Environ Pollut 90:83-87
3. Corvini PFX, Vinken R, Hommes G, Schmidt B, Dohmann M (2004a) Degradation of the radioactive and non-labelled branched 3′,5′-dimethyl 3′-heptyl-phenol nonylphenol isomer by Sphingomonas TTNP3. Biodegradation 15:9-18
4. 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 50:195-202
5. Corvini PFX, Meesters RJW, Schäffer A, Schröder HFr, 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
6. Dachs J, Van Ry DA, Eisenreich SJ (1999) Occurrence of estrogenic nonylphenols in the urban and coastal atmosphere of the lower Hudson River estuary. Environ Sci Technol 33:2676-2679
7. Di Corcia A, Costantino A, Crescenzi C, Marinoni E, Samperi R (1998) Characterization of recalcitrant intermediates of the branched alkyl side chain of nonylphenol ethoxylate surfactants. Environ Sci Technol 32:2401-2409
8. Ekelund R, Granmo Å, Magnusson K, Berggren M (1993) Biodegradation of 4-nonylphenol in seawater and sediment. Environ Pollut 79:59-61
9. Espadaler I, Caixach J, Om J, Ventura F, Cortina M, Pauné F, Rivera J (1997) Identification of organic pollutants in Ter river and its system of reservoirs supplying water to Barcelona (Catalonia, Spain): a study by GC/MS and FAB/MS. Water Res 31:1996-2004
10. Fereira-Leach AMR, Hill EM (2001) Bioconcentration and distribution of 4-tert-octylphenol residues in tissues of the rainbow trout (Oncorhynchus mykiss). Mar Environ Res 51:75-89
11. 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
12. Fujii K, Urano N, Ushio H, Satomi M, Kimura S (2001) Sphingomonas cloacae sp. nov., a nonylphenoldegrading bacterium isolated from wastewater of a sewage-treatment plant in Tokyo. Int J Syst Evol Microbiol 51:603-610
13. 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
14. Guroff G, Daly JW, Jerina DM, Renson J, Witkop B, Udenfriend S (1967) Hydroxylation-induced migration: the NIH shift. Science 157:1524-1530
15. Hesselsøe M, Jensen D, Skals K, Olesen T, Moldrup P, Roslev P, Krog Mortensen G, Henriksen K (2001) Degradation of 4-nonylphenol in homogeneous and nonhomogeneous mixtures of soil and sewage sludge. Environ Sci Technol 35:3695-3700
16. SPα). J Biochem 128:189-194
17. Koerts J, Soffers AEMF, Vervoort J, De Jager A, Rietjens IMCM (1998) Occurrence of the NIH shift upon the cytochrome P450-catalyzed in vivo and in vitro aromatic ring hydroxylation of fluorobenzenes. Chem Res Toxicol 11:503-512
18. 14C-nonylphenol isomer in pond snails, Lymnea stagnalis L. Aquat Toxicol 62:305-319
19. Liber K, Knuth ML, Stay FS (1999) An integrated evaluation of the persistence and effects of 4-nonylphenol in an experimental littoral ecosystem. Environ Toxicol Chem 18:357-362
20. Lobos JH, Leib TK, Su TM (1992) Biodegradation of bisphenol A and other bisphenols by a gram-negative bacterium. Appl Environ Microbiol 58:1823-1831
21. Soto AM, Justica H, Wray JW, Sonnenschein C (1991) Para-nonylphenol: an estrogenic xenobiotic released from polystyrene. Environ Health Perspect 92:167-173
22. Spivack J, Leib TK, Lobos JH (1994) Novel pathway for bacterial metabolism of bisphenol A. J Biol Chem 269:7323-7329
23. Sundaram KMS, Szeto S (1981) The dissipation of nonylphenol in stream and pond water under simulated field conditions. J Environ Sci Health B16:767-776
24. Tanghe T, Devriese G, Verstraete W (1998) Nonylphenol degradation in lab scale activated sludge units is temperature dependent. Water Res 32:2889-2896
25. Tanghe T, Dhooge W, Verstraete W (1999) Isolation of a bacterial strain able to degrade branched nonylphenol. Appl Environ Microbiol 65:746-751
26. Tanghe T, Dhooge W, Verstraete W (2000) Formation of the metabolic intermediate 2,4,4-trimethyl-3-pentanol during incubation of a Sphingomonas sp. strain with the xeno-estrogenic octylphenol. Biodegradation 11:11-19
27. Topp E, Starratt A (2000) Rapid mineralization of the endocrine-disrupting chemical 4-nonylphenol in soil. Environ Toxicol Chem 19:313-318
28. Ushiba Y, Takahara Y, Ohta H (2003) Sphingobium amiense sp. nov., a novel nonylphenol-degrading bacterium isolated from a river sediment. Int J Syst Evol Microbiol 53:2045-2048
29. Vallini G, Frassinetti S, Scorzetti G (1997) Candida aquaetextoris sp. nov., a new species of yeast occurring in sludge from a textile industry wastewater treatment plant in Tuscany, Italy. Int J Syst Bacteriol 47:336-340
30. Van Ginkel CG 1996. Complete degradation of xenobiotic surfactants by consortia of aerobic microorganisms. Biodegradation 7:151-164
31. 14C-labelled nonylphenol isomers. J Label Compd Radiopharm 45:1253-1263
32. Wheeler TF, Heim JR, LaTorre MR, B Janes (1997) Mass spectral characterization of p-nonylphenol isomers using high-resolution capillary GC-MS. J Chromatogr Sci 35:19-30