The degradation of alkylphenols by Sphingomonas sp. strain TTNP3 - a review on seven years of research

New Biotechnology

Volumn 30, Issue 1, 2012, Pages 88-95

  Kolvenbach, B A ^a   Corvini, P F X ^a,b  

^a UNIVERSITY OF APPLIED SCIENCES AND ARTS NORTHWESTERN SWITZERLAND   (Switzerland)

^b NANJING UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLPHENOLIC COMPOUNDS; ALKYLPHENOLS; BIOANALYTICAL METHODS; GENES ENCODING; REACTION MECHANISM; SPHINGOMONAS SP;

BIODEGRADATION;

CARBON;

1 [2 (4 HYDROXYPHENYL)PROPAN 2 YL]CYCLOHEX 2 ENE 1,4 DIOL; 2 [2 (4 HYDROXYPHENYL)PROPAN 2 YL]CYCLOHEX 2 ENE 1,4 DIOL; 3 OXOADIPIC ACID; 4 262 NONYLPHENOL; 4 353 NONYLPHENOL; 4 363NONYLPHENOL; 4 ISOPROPENYLPHENOL; 4 ISOPROPYLPHENOL; 4,4' ISOPROPYLIDENEDIPHENOL; ALKYLPHENOL; CARBON; HYDROQUINONE; HYDROXYMUCONIC ACID SEMIALDEHYDE; MALEYLACETIC ACID; QUINOL; UNCLASSIFIED DRUG;

ATOM; BACTERIAL STRAIN; BURKHOLDERIA; ENZYME MEMBRANE BIOREACTOR; MICROBIAL DEGRADATION; MOLECULAR MECHANICS; NONHUMAN; PRIORITY JOURNAL; PSEUDOMONAS; REVIEW; SPHINGOBIUM; SPHINGOBIUM CHLOROPHENOLICUM; SPHINGOMONAS; WASTE WATER MANAGEMENT;

BIODEGRADATION, ENVIRONMENTAL; BIOREACTORS; METABOLIC NETWORKS AND PATHWAYS; PHENOLS; RESEARCH; SPHINGOMONAS;

BACTERIA (MICROORGANISMS); SPHINGOMONAS SP.;

EID: 84867660637     PISSN: 18716784     EISSN: 18764347     Source Type: Journal    
DOI: 10.1016/j.nbt.2012.07.008     Document Type: Review

References (54)

1. Colborn T., et al. Developmental effects of endocrine-disrupting chemicals in wildlife and humans. Environ. Impact Assess. Rev. 1994, 14:469-489.
2. Soto A.M., et al. Para-nonyl-phenol-an estrogenic xenobiotic released from modified polystyrene. Environ. Health Perspect. 1991, 92:167-173.
3. Krishnan A.V., et al. Bisphenol-A: an estrogenic substance is released from polycarbonate flasks during autoclaving. Endocrinology 1993, 132:2279-2286.
4. Berryman D., et al. Nonylphenolic compounds in drinking and surface waters downstream of treated textile and pulp and paper effluents: a survey and preliminary assessment of their potential effects on public health and aquatic life. Chemosphere 2004, 56:247-255.
5. Dessi-Fulgheri F., et al. Effects of perinatal exposure to bisphenol A on play behavior of female and male juvenile rats. Environ. Health Perspect. 2002, 110(S3):409-414.
6. vom Saal F.S., Hughes C. An extensive new literature concerning low-dose effects of bisphenol A shows the need for a new risk assessment. Environ. Health Perspect. 2005, 113:926-933.
7. Oehlmann J., et al. Bisphenol A induces superfeminization in the ramshorn snail Marisa cornuarietis (Gastropoda: Prosobranchia) at environmentally relevant concentrations. Environ. Health Perspect. 2006, 114:127-133.
8. Wheeler T.F., et al. Mass spectral characterization of p-nonylphenol isomers using high-resolution capillary GC-MS. J. Chromatogr. Sci. 1997, 35:19-30.
9. Van Ginkel C.G. Complete degradation of xenobiotic surfactants by consortia of aerobic microorganisms. Biodegradation 1996, 7:151-164.
10. Ekelund R., et al. Biodegradation of 4-nonylphenol in seawater and sediment. Environ. Pollut. 1993, 79:59-61.
11. Fujii K., et al. Microbial degradation of nonylphenol in some aquatic environments. Fish. Sci. 2000, 66:44-48.
12. Topp E., Starratt A. Rapid mineralization of the endocrine-disrupting chemical 4-nonylphenol in soil. Environ. Toxicol. Chem. 2000, 19:313-318.
13. Vallini G., et al. 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. 1997, 47:336-340.
14. Tanghe T., et al. Isolation of a bacterial strain able to degrade branched nonylphenol. Appl. Environ. Microbiol. 1999, 65:746-751.
15. Fujii K., et al. Sphingomonas cloacae sp nov., a nonylphenol-degrading bacterium isolated from wastewater of a sewage-treatment plant in Tokyo. Int. J. Syst. Evol. Microbiol. 2001, 51:603-610.
16. Gabriel F.L.P., et al. Differential degradation of nonylphenol isomers by Sphingomonas xenophaga Bayram. Appl. Environ. Microbiol. 2005, 71:1123-1129.
17. Ushiba Y., et al. Sphingobium amiense sp nov., a novel nonylphenol-degrading bacterium isolated from a river sediment. Int. J. Syst. Evol. Microbiol. 2003 Nov, 53:2045-2048.
18. de Vries Y.P., et al. Organic nutrient-dependent degradation of branched nonylphenol by Sphingomonas sp. YT isolated from a river sediment sample. Microb. Environ. 2001, 16:240-249.
19. Ieda T., et al. Analysis of nonylphenol isomers in a technical mixture and in water by comprehensive two-dimensional gas chromatography/mass spectrometry. Environ. Sci. Technol. 2005, 39:7202-7207.
20. Moeder M., et al. Identification of isomeric 4-nonylphenol structures by gas chromatography-tandem mass spectrometry combined with cluster analysis. J. Chromatogr. A 2006, 1102:245-255.
21. Corvini P.F.X., et al. Degradation of the radioactive and non-labelled branched 4(3',5'-dimethyl 3'-heptyl)-phenol nonylphenol isomer by Sphingomonas TTNP3. Biodegradation 2004, 15:9-18.
22. Corvini P.F.X., et al. Metabolism of a nonylphenol isomer by Sphingomonas sp. strain TTNP3. Environ. Chem. Lett. 2005, 2:185-189.
23. Corvini P.F.X., et al. The degradation of alpha-quaternary nonylphenol isomers by Sphingomonas sp. strain TTNP3 involves a type II ipso-substitution mechanism. Appl. Microbiol. Biotechnol. 2006, 70:114-122.
24. Preuss T.G., et al. Some nonylphenol isomers show antiestrogenic potency in the MVLN cell assay. Toxicol. In Vitro 2006, 24:129-134.
25. Ruß A.S., et al. Synthesis of branched para-nonylphenol isomers: occurrence and quantification in two commercial mixtures. Chemosphere 2005, 60:1624-1635.
26. Corvini P.F.X., et al. Degradation of a nonylphenol single isomer by Sphingomonas sp. strain TTNP3 leads to a hydroxylation-induced migration product. Appl. Environ. Microbiol. 2004, 70:6897-6900.
27. Martin G., et al. Hydroxylation reaction catalyzed by the Burkholderia cepacia AC1100 bacterial strain. Eur. J. Biochem. 1999, 261:533-539.
28. Taniguchi K., et al. Further studies on phenylpyruvate oxidase. J. Biol. Chem. 1964, 239:3389-3395.
29. Guroff G., et al. Hydroxylation-induced migration: the NIH shift. Recent experiments reveal an unexpected and general result of enzymatic hydroxylation of aromatic compounds. Science (New York, NY) 1967, 157:1524-1530.
30. Jerina D.M., et al. A new aspect of drug metabolism. Science 1974, 185:573-582.
31. Koerts J., et al. Occurrence of the NIH shift upon the cytochrome P450-catalyzed in vivo and in vitro aromatic ring hydroxylation of fluorobenzenes. Chem. Res. Toxicol. 1998, 11:503-512.
32. Gabriel F.L.P., et al. A novel metabolic pathway for degradation of 4-nonylphenol environmental contaminants by Sphingomonas xenophaga Bayram - ipso-hydroxylation and intramolecular rearrangement. J. Biol. Chem. 2005, 280:15526-15533.
33. Kamerbeek N.M., et al. 4-Hydroxyacetophenone monooxygenase from Pseudomonas fluorescens ACB. Eur. J. Biochem. 2001, 268:2547-2557.
34. Corvini P.F.X., et al. Microbial degradation of a single branched isomer of nonylphenol by Sphingomonas TTNP3. Water Sci. Technol. 2004, 50:189-194.
35. Ohe T., et al. Substituent elimination from p-substituted phenols by cytochrome P450. Drug Metab. Dispos. 1997, 25:116-122.
36. Spain J.C., Gibson D.T. Pathway for biodegradation of para-nitrophenol in a Moraxella sp. Appl. Environ. Microbiol. 1991, 57:812-819.
37. McCarthy D.L., et al. In vivo levels of chlorinated hydroquinones in a pentachlorophenol-degrading bacterium. Appl. Environ. Microbiol. 1997, 63:1883-1888.
38. White G.F., et al. Bacterial scission of ether bonds. Microbiol. Rev. 1996, 60:216-232.
39. Vatsis K.P., Coon M.J. Ipso-substitution by cytochrome P450 with conversion of p-hydroxybenzene derivatives to hydroquinone: evidence for hydroperoxo-iron as the active oxygen species. Arch. Biochem. Biophys. 2002, 397:119-129.
40. Tanghe T., et al. Formation of the metabolic intermediate 2,4,4-trimethyl-2-pentanol during incubation of a shape Sphingomonas sp. strain with the xeno-estrogenic octylphenol. Biodegradation 2000, 11:11-19.
41. Fuji K., et al. Profile of a nonylphenol-degrading microflora and its potential for bioremedial applications. J. Biochem. 2000, 128:909-916.
42. Corvini P.F.X., et al. Microbial degradation of nonylphenol and other alkylphenols-our evolving view. Appl. Microbiol. Biotechnol. 2006, 72:223-243.
43. Gabriel F.L.P., et al. Isomer-specific degradation and endocrine disrupting activity of nonylphenols. Environ. Sci. Technol. 2008, 42:6399-6408.
44. Kolvenbach B., et al. Degradation pathway of Bisphenol A: does ipso substitution apply to phenols containing a quaternary {alpha}-carbon structure in the para position?. Appl. Environ. Microbiol. 2007, 73:4776-4784.
45. Kolvenbach B.A., et al. An unexpected gene cluster for downstream degradation of alkylphenols in Sphingomonas sp. strain TTNP3. Appl. Microbiol. Biotechnol. 2012, 93:1315-1324.
46. Kolvenbach B.A., et al. Purification and characterization of hydroquinone dioxygenase from Sphingomonas sp. strain TTNP3. AMB Express. 2011, 1:8.
47. Moonen M.J.H., et al. Hydroquinone dioxygenase from Pseudomonas fluorescens ACB: a novel member of the family of nonheme-iron(II)-dependent dioxygenases. J. Bacteriol. 2008, 190:5199-5209.
48. Porter A.W., Hay A.G. Identification of opdA, a gene involved in biodegradation of the endocrine disrupter octylphenol. Appl. Environ. Microbiol. 2007, 73:7373-7379.
49. Porter A.W., et al. Identification of the flavin monooxygenase responsible for ipso substitution of alkyl and alkoxyphenols in Sphingomonas sp. TTNP3 and Sphingobium xenophagum Bayram. Appl. Microbiol. Biotechnol. 2012, 94:261-272.
50. Cirja M., et al. Impact of bio-augmentation with Sphingomonas sp. strain TTNP3 in membrane bioreactors degrading nonylphenol. Appl. Microbiol. Biotechnol. 2009, 84:183-189.
51. Li C., et al. Role of dissolved humic acids in the biodegradation of a single isomer of nonylphenol by Sphingomonas sp. Chemosphere 2007, 68:2172-2180.
52. Cai M., Xun L. Organization and regulation of pentachlorophenol-degrading genes in Sphingobium chlorophenolicum ATCC 39723. J. Bacteriol. 2002, 184:4672-4680.
53. Endo R., et al. Identification and characterization of genes involved in the downstream degradation pathway of gamma-hexachlorocyclohexane in Sphingomonas paucimobilis UT26. J. Bacteriol. 2005, 187:847-853.
54. Takeo M., et al. Two identical nonylphenol monooxygenase genes linked to IS6100 and some putative IS elements in Sphingomonas sp. NP5. Microbiology 2012, 10.1099/mic.0.055335-0.