References
- Ahel, M., C. Schaffner, and W. Giger. 1996. Behavior of alkylphenol polyethoxylates surfactants in the aquatic environment-III. Occurrence and elimination of their persistent metabolites during infiltration of river water to groundwater. Water Res. 30: 37-46 https://doi.org/10.1016/0043-1354(95)00123-3
- Ajithkumar, B., V. P. Ajithkumar, and R. Iriye. 2003. Degradation of 4-amylphenol and 4-hexylphenol by a new activated sludge isolate of Pseudomonas veronii and proposal for a new subspecies status. Res. Microbiol. 154: 17-23 https://doi.org/10.1016/S0923-2508(02)00009-8
- Altschul, S. F., W. Gish, W. Mille, E. W. Myer, and D. J. Lipman. 1990. Basic local alignment search tool. J. Mol. Biol. 219: 403-410 https://doi.org/10.1016/0022-2836(91)90182-6
- Bennett, E. R. and C. D. Metcalfe. 1998. Distribution of alkylphenol compounds in great lakes sediments, United States and Canada. Environ. Toxicol. Chem. 17: 1230-1235 https://doi.org/10.1897/1551-5028(1998)017<1230:DOACIG>2.3.CO;2
- Bulayeva, N. N., B. Gametchu, and C. S. Watson. 2004. Quantitative measurement of estrogen-induced ERK 1 and 2 activation via multiple membrane-initiated signaling pathways. Steroids 69: 181-192 https://doi.org/10.1016/j.steroids.2003.12.003
- Bulayeva, N. N. and C. S. Watson. 2004. Xenoestrogen-induced ERK-1 and ERK-2 activation via multiple membrane-initiated signaling pathways. Environ. Health Perspect. 112: 1481-1487 https://doi.org/10.1289/ehp.7175
- Corti, A., S. Frassinetti, G. Vallini, S. D'Antone, C. Fichi, and R. Solaro. 1995. Biotransformation of nonionic surfactants. I. Biotransformation of 4-(1-nonyl)phenol by Candida maltosa isolate. Environ. Pollut. 90: 83-87 https://doi.org/10.1016/0269-7491(94)00080-W
- Corvini, P. F. X., J. Hollender, R. Ji, S. Schumacher, J. Prell, G. Hommes, U. Priefer, R. Vinken, and A. Schaffer. 2006. The degradation of alpha-quaternary nonylphenol isomers by Sphingomonas sp. strain TTNP3 involves a type II ipso-substitution mechanism. Appl. Microbiol. Biotechnol. 70: 114-122 https://doi.org/10.1007/s00253-005-0080-0
- Corvini, P. F. X., R. J. W. Meesters, A. Schaffer, H. F. Schroder, R. Vinken, and J. Hollender. 2004. Degradation of a nonylphenol single isomer by Sphingomonas sp. strain TTNP3 leads to a hydroxylation-induced migration product. Appl. Environ. Microbiol. 70: 6897-6900 https://doi.org/10.1128/AEM.70.11.6897-6900.2004
- Corvini, P. F., R. Vinken, G. Hommes, B. Schmidt, and M. Dohmann. 2004. Degradation of the radioactive and non-labelled branched 4(3',5'-dimethyl 3'-heptyl)-phenol nonylphenol isomer by Sphingomonas TTNP3. Biodegradation 15: 9-18 https://doi.org/10.1023/B:BIOD.0000009937.20251.d2
- Darby, J. M., D. G. Taylor, and D. J. Hopper. 1987. Hydroquinone as the ring-fission substrate in the catabolism of 4-ethylphenol and 4-hydroxyacetophenone by Pseudomonas putida JD1. J. Gen. Microbiol. 133: 2137-2146
- de Vries, Y. P., Y. Takahara, Y. Ikunaga, et al. 2001. Organic nutrient-dependent degradation of branched nonylphenol by Sphingomonas sp. YT isolated from a river sediment sample. Microb. Environ. 16: 240-249 https://doi.org/10.1264/jsme2.2001.240
- Ejlertsson, J., M. Nilsson, H. Kylin, A. Bergman, L. Karlson, M. Oquist, and B. Svensson. 1999. Anaerobic degradation of nonylphenol mono- and diethoxylates in digestor sludge, landfilled municipal solid waste, and landfilled sludge. Environ. Sci. Technol. 33: 301-306 https://doi.org/10.1021/es980669u
- Felsenstein, J. 1993. PHYLIP (phylogenetic inference package), version 3.5c. Department of Genome Sciences, University of Washington, Seattle, U.S.A
- Fujii, K., N. Urano, H. Ushio, M. Satomi, H. Iida, N. Ushio-Sata, and S. Kimura. 2000. Profile of a nonylphenol-degrading microflora and its potential for bioremedial applications. J. Biochem. 128: 909-916 https://doi.org/10.1093/oxfordjournals.jbchem.a022841
- Gabriel, F. L. P., W. Giger, K. Guenther, and H.-P. E. Kohler. 2005. Differential degradation of nonylphenol isomers by Sphingomonas xenophaga Bayram. Appl. Environ. Microbiol. 71: 1123-1129 https://doi.org/10.1128/AEM.71.3.1123-1129.2005
- Gabriel, F. L. P., A. Heidlberger, D. Rentsch, W. Giger, K. Guenther, and H.-P. E. Kohler. 2005. A novel metabolic pathway for degradation of 4-nonylphenol environmental contaminants by Sphingomonas xenophaga Bayram. J. Biol. Chem. 280: 15526-15533 https://doi.org/10.1074/jbc.M413446200
- Hemmer, M. J., B. L. Hemmer, C. J. Bowman, K. J. Kroll, L. C. Folmar, D. Marcovich, M. D. Hoglund, and N. D. Denslow. 2001. Effects of p-nonylphenol, methoxychlor, and endosulfan on vitellogenin induction and expression in sheepshead minnow (Cyprinodon variegatus). Environ. Toxicol. Chem. 20: 336-343 https://doi.org/10.1897/1551-5028(2001)020<0336:EOPNMA>2.0.CO;2
- Inoue, K., S. Kondo, Y. Yoshie, K. Kato, Y. Yoshimura, M. Horie, and H. Nakazawa. 2001. Migration of 4-nonylphenol from polyvinyl chloride food packaging films into food simulants and foods. Food Addit. Contam. 18: 157-164 https://doi.org/10.1080/02652030010018930
- Jeong, J. J., J. H. Kim, C.-K. Kim, I. Hwang, and K. Lee. 2003. 3- and 4-alkylphenol degradation pathway in Pseudomonas sp. strain KL28: Genetic organization of the lap gene cluster and substrate specificities of phenol hydroxylase and catechol 2,3-dioxygenase. Microbiology 149: 3265-3277 https://doi.org/10.1099/mic.0.26628-0
- Johnson, J. L. 1994. Similarity analysis of rRNAs, Chapter 27, pp. 683-700. In P. Gerhardt, R. G. E. Murray, W. A. Wood, and N. R. Krieg (eds.), Methods for General and Molecular Bacteriology. American Society for Microbiology, Washington, DC
- Kamerbeeck, N. M., M. J. H. Moonen, J. G. M. van der Ven, W. J. H. van Berkel, M. W. Fraaije, and D. B. Janssen. 2001. 4-Hydroxyacetophenone monooxygenase from Pseudomonas fluorescens ACB. A novel flavoprotein catalyzing Baeyer-Villiger oxidation of aromatic compounds. Eur. J. Biochem. 268: 2547-2557 https://doi.org/10.1046/j.1432-1327.2001.02137.x
- King, E. O., M. K. Ward, and D. E. Raney. 1954. Two simple media for the demonstration of pyocyanin and fluorescein. J. Lab. Clin. Med. 44: 301-307
- Kwack, S. J., O. Kwon, H. S. Kim, S. S. Kim, S. H. Kim, K. H. Sohn, R. D. Lee, C. H. Park, E. B. Jeung, B. S. An, and K. L. Park. 2002. Comparative evaluation of alkylphenolic compounds on estrogenic activity in vitro and in vivo. J. Toxicol. Environ. Health Part A 65: 419-431 https://doi.org/10.1080/15287390252808082
- Lowry, O. H., N. J. Rosebrough, A. L. Farr, and R. J. Randall. 1951. Protein measurement with the Folin phenol reagent. J. Biol. Chem. 193: 265-267
- Moeder, M., C. Martin, D. Schlosser, J. Harynuk, and T. Gorecki. 2006. Separation of technical 4-nonylphenols and their biodegradation products by comprehensive two-dimensional gas chromatography coupled to time-of-flight mass spectrometry. J. Chromatogr. A 1107: 233-239 https://doi.org/10.1016/j.chroma.2005.12.092
-
Michelangeli, F., S. Orlowski, P. Champeil, J. M. East, and A. G. Lee. 1990. Mechanism of inhibition of the
$(Ca^{2+}-Mg^{2+})$ -ATPase by nonylphenol. Biochemistry 29: 3091-3101 https://doi.org/10.1021/bi00464a028 - Ngai, K. L., E. L. Neidle, and L. N. Ornston. 1990. Catechol and chlorocatechol 1,2-dioxygenases. Methods Enzymol. 188: 122-126 https://doi.org/10.1016/0076-6879(90)88022-3
- Nozaki, M. 1970. Metapyrocatechase (Pseudomonas). Methods Enzymol. 17A: 522-525
- Okai, Y., E. F. Sato, K. Higashi-Okai, and M. Inoue. 2004. Enhancing effect of the endocrine disruptor para-nonylphenol on the generation of reactive oxygen species in human blood neutrophils. Environ. Health Perspect. 112: 553-556 https://doi.org/10.1289/ehp.6584
- Saitou, N. and M. Nei. 1987. The neighbor-joining method: A new method for reconstructing phylogenetic trees. Mol. Biol. Evol. 4: 406-425
- Servos, M. R. 1999. Review of aquatic toxicity, estrogenic responses and bioaccumulation of alkylphenols and alkylphenol polyethoxylates. Water Qual. Res. J. Canada 34: 123-177
- Smibert, R. M. and N. R. Krieg. 1994. Phenotypic characterization, Chapter 25, pp. 607-654. In P. Gerhardt, R. G. E. Murray, W. A. Wood, and N. R. Krieg (eds.), Methods for General and Molecular Bacteriology. American Society for Microbiology, Washington, DC
- Singleton, V. L., R. Orthofer, and R. M. Lamuela-Raventos. 1999. Analysis of total phenols and other oxidation substrates and antioxidants by means of Folin-Ciocalteu reagent. Methods Enzymol. 299: 152-178 https://doi.org/10.1016/S0076-6879(99)99017-1
- Soares, A., B. Guieysse, O. Delgado, and B. Mattiasson. 2003. Aerobic biodegradation of nonylphenol by cold-adapted bacteria. Biotechnol. Lett. 25: 731-738 https://doi.org/10.1023/A:1023466916678
- Soares, A., M. Murto, B. Guieysse, and B. Mattiasson. 2006. Biodegradation of nonylphenol in a continuous bioreactor at low temperatures and effects on the microbial population. Appl. Microbiol. Biotechnol. 69: 597-606 https://doi.org/10.1007/s00253-005-0067-x
- Soto, A. M., H. Justicia, J. W. Wray, and C. Sonnenschein 1991. p-Nonylphenol: An estrogenic xenobiotic released from 'modified' polystyrene. Environ. Health Perspect. 92: 167-173 https://doi.org/10.2307/3431154
- Tanghe, T., W. Dhooge, and W. Verstraete. 1999. Isolation of a bacterial strain able to degrade branched nonylphenol. Appl. Environ. Microbiol. 65: 746-751
- Tanghe, T., W. Dhooge, and W. Verstraete 2000. Formation of metabolic intermediate 2,4,4-trimethyl-2-pentanol during incubation of a Sphingomonas sp. strain with the xeno-estrogenic octylphenol. Biodegradation 11: 11-19 https://doi.org/10.1023/A:1026518727690
- Thiele, B., K. Gunther, and M. J. Schwuger. 1997. Alkylphenol ethoxylates: Trace analysis and environmental behavior. Chem. Rev. 97: 3247-3272 https://doi.org/10.1021/cr970323m
- Thiele, B., V. Heinke, E. Kleist, and K. Gunther. 2004. Contribution to the structual elucidationof 10 isomers of technical p-nonylphenol. Environ. Sci. Technol. 38: 3405-3411 https://doi.org/10.1021/es040026g
- Thompson, J. D., D. G. Higgins, and T. J. Gibson. 1994. ClustalW: 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 https://doi.org/10.1093/nar/22.22.4673
- U.S. EPA. 2003. Ambient Aquatic Life Water Quality Criteria for Nonylphenol - Draft. Washington, DC
- Ushiba, Y., Y. Takahara, and H. Ohta. 2003. Sphingobium amiense sp. nov., a novel nonylphenol-degrading bacterium isolated from a river sediment. Int. J. Syst. Evol. Microbiol. 53: 2045-2048 https://doi.org/10.1099/ijs.0.02581-0
- Vallini, G., S. Frassinetti, and G. Scorzetti. 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 https://doi.org/10.1099/00207713-47-2-336
- Van de Peer, Y. and R. De Wachter. 1994. TREECON for Windows: A software package for the construction and drawing of evolutionary trees for the Microsoft Windows environment. Comput. Appl. Biosci. 10: 569-570
- Van Ginkel, C. G. 1996. Complete degradation of xenobiotic surfactants by consortia of aerobic microorganisms. Biodegradation 7: 151-164 https://doi.org/10.1007/BF00114627
- Wheeler, T. F., J. R. Heim, M. R. LaTorre, and A. B. Janes 1997. Mass spectral characterization of p-nonylphenol isomers using high-resolution capillary GC-MS. J. Chromatogr. Sci. 35: 19-30 https://doi.org/10.1093/chromsci/35.1.19
- White, R., S. Jobling, S. A. Hoare, J. P. Sumpter, and M. G. Parker. 1994. Environmentally persistent alkylphenolic compounds are estrogenic. Endocrinology 135: 175-182 https://doi.org/10.1210/en.135.1.175
- Yao, G. and Y. Hou. 2004. Nonylphenol induces thymocyte apoptosis through Fas/FasL pathway by mimicking estrogen in vivo. Environ. Toxicol. Pharmacol. 17: 19-27 https://doi.org/10.1016/j.etap.2004.01.006
- Ying, G. G., B. Williams, and R. Kookana. 2002. Environmental fate of alkylphenols and alkylphenol ethoxylates. A review. Environ. Int. 28: 215-226 https://doi.org/10.1016/S0160-4120(02)00017-X