Isomer-specific biodegradation of nonylphenol in river sediments and structure-biodegradability relationship

Environmental Science and Technology

Volumn 48, Issue 2, 2014, Pages 1008-1014

  Lu, Zhijiang ^a   Gan, Jay ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANOXIC CONDITIONS; DEGREE OF BRANCHING; ENVIRONMENTAL ESTROGENS; ENVIRONMENTAL FATE; ENVIRONMENTAL PROCESS; LINEAR CORRELATION; MOLECULAR DESCRIPTORS; SHORT SIDE CHAINS;

BIODEGRADATION; OXIC SEDIMENTS; PHENOLS; RIVERS;

ISOMERS;

NONYLPHENOL; ORGANIC CARBON; PHENOL DERIVATIVE;

BIODEGRADATION; CALCIFICATION; CORRELATION; ENVIRONMENTAL RISK; ESTROGENIC COMPOUND; FLUVIAL DEPOSIT; PERSISTENCE; PHENOL; RIVER BED;

ANOXIA; ARTICLE; BACTERIUM; BIODEGRADABILITY; BIODEGRADATION; CHEMICAL STRUCTURE; CONTROLLED STUDY; ENVIRONMENTAL IMPACT; HALF LIFE TIME; INCUBATION TIME; ISOMER; NONHUMAN; RIVER; SEDIMENT; SPHINGOBIUM XENOPHAGUM; ANAEROBIC GROWTH; BIOREMEDIATION; CHEMISTRY; ISOMERISM; METABOLISM; OXIDATION REDUCTION REACTION; PH; REGRESSION ANALYSIS;

ANAEROBIOSIS; BIODEGRADATION, ENVIRONMENTAL; GEOLOGIC SEDIMENTS; HALF-LIFE; HYDROGEN-ION CONCENTRATION; ISOMERISM; LEAST-SQUARES ANALYSIS; OXIDATION-REDUCTION; PHENOLS; RIVERS;

EID: 84892768961     PISSN: 0013936X     EISSN: 15205851     Source Type: Journal    
DOI: 10.1021/es403950y     Document Type: Article

References (34)

1. Ying, G. G.; Williams, B.; Kookana, R. Environmental fate of alkylphenols and alkylphenol ethoxylates-A review Environ. Int. 2002, 28 (3) 215-226
2. Soares, A.; Guieysse, B.; Jefferson, B.; Cartmell, E.; Lester, J. N. Nonylphenol in the environment: A critical review on occurrence, fate, toxicity and treatment in wastewaters Environ. Int. 2008, 34 (7) 1033-1049
3. Giger, W.; Gabriel, F. L. P.; Jonkers, N.; Wettstein, F. E.; Kohler, H. P. E. Environmental fate of phenolic endocrine disruptors: Field and laboratory studies Philos. Trans. R. Soc. A 2009, 367 (1904) 3941-3963
4. Anonymous, Overview of the US nonylphenol sector. Focus Surfact. 2007, 2007, (8), 4.
5. Mao, Z.; Zheng, X. F.; Zhang, Y. Q.; Tao, X. X.; Li, Y.; Wang, W. Occurrence and biodegradation of nonylphenol in the environment Int. J. Mol. Sci. 2012, 13 (1) 491-505
6. Writer, J. H.; Barber, L. B.; Ryan, J. N.; Bradley, P. M. Biodegradation and attenuation of steroidal hormones and alkylphenols by stream biofilms and sediments Environ. Sci. Technol. 2011, 45 (10) 4370-4376
7. Writer, J. H.; Ryan, J. N.; Keefe, S. H.; Barber, L. B. Fate of 4-nonylphenol and 17 β-estradiol in the Redwood River of Minnesota Environ. Sci. Technol. 2012, 46 (2) 860-868
8. Rice, C. P.; Schmitz-Afonso, I.; Loyo-Rosales, J. E.; Link, E.; Thoma, R.; Fay, L.; Altfater, D.; Camp, M. J. Alkylphenol and alkylphenol-ethoxylates in carp, water, and sediment from the Cuyahoga River, Ohio Environ. Sci. Technol. 2003, 37 (17) 3747-3754
9. Bechi, N.; Ietta, F.; Romagnoli, R.; Jantra, S.; Cencini, M.; Galassi, G.; Serchi, T.; Corsi, I.; Focardi, S.; Paulesu, L. Environmental levels of para -nonylphenol are able to affect cytokine secretion in human placenta Environ. Health Perspect. 2010, 118 (3) 427-431
10. Lalah, J. O.; Schramm, K. W.; Henkelmann, B.; Lenoir, D.; Behechti, A.; Günther, K.; Kettrup, A. The dissipation, distribution and fate of a branched 14C-nonylphenol isomer in lake water/sediment systems Environ. Pollut. 2003, 122 (2) 195-203
11. Chang, B. V.; Yu, C. H.; Yuan, S. Y. Degradation of nonylphenol by anaerobic microorganisms from river sediment Chemosphere 2004, 55 (4) 493-500
12. De Weert, J.; Streminska, M.; Hua, D.; Grotenhuis, T.; Langenhoff, A.; Rijnaarts, H. Nonylphenol mass transfer from field-aged sediments and subsequent biodegradation in reactors mimicking different river conditions J. Soils Sed. 2010, 10 (1) 77-88
13. Yuan, S. Y.; Yu, C. H.; Chang, B. V. Biodegradation of nonylphenol in river sediment Environ. Pollut. 2004, 127 (3) 425-430
14. De Weert, J. P. A.; Vinas, M.; Grotenhuis, T.; Rijnaarts, H. H. M.; Langenhoff, A. A. M. Degradation of 4- n -nonylphenol under nitrate reducing conditions Biodegradation 2011, 22 (1) 175-187
15. Sarmah, A. K.; Northcott, G. L. Laboratory degradation studies of four endocrine disruptors in two environmental media Environ. Toxicol. Chem. 2008, 27 (4) 819-827
16. Shang, D. Y.; Macdonald, R. W.; Ikonomou, M. G. Persistence of nonylphenol ethoxylate surfactants and their primary degradation products in sediments from near a municipal outfall in the Strait of Georgia, British Columbia, Canada Environ. Sci. Technol. 1999, 33 (9) 1366-1372
17. Eganhouse, R. P.; Pontolillo, J.; Gaines, R. B.; Frysinger, G. S.; Gabriel, F. L. P.; Kohler, H. P. E.; Giger, W.; Barber, L. B. Isomer-specific determination of 4-nonylphenols using comprehensive two-dimensional gas chromatography/time-of-flight mass spectrometry Environ. Sci. Technol. 2009, 43 (24) 9306-9313
18. Gabriel, F. L. P.; Routledge, E. J.; Heidlberger, A.; Rentsch, D.; Guenther, K.; Giger, W.; Sumpter, J. P.; Kohler, H. P. E. Isomer-specific degradation and endocrine disrupting activity of nonylphenols Environ. Sci. Technol. 2008, 42 (17) 6399-6408
19. Shan, J.; Jiang, B. Q.; Yu, B.; Li, C. L.; Sun, Y. Y.; Guo, H. Y.; Wu, J. C.; Klumpp, E.; Schaffer, A.; Ji, R. Isomer-specific degradation of branched and linear 4-nonylphenol isomers in an oxic soil Environ. Sci. Technol. 2011, 45 (19) 8283-8289
20. Lin, K.; Haver, D.; Oki, L.; Gan, J. Transformation and sorption of fipronil in urban stream sediments J. Agric. Food Chem. 2008, 56 (18) 8594-8600
21. Thiele, B.; Heinke, V.; Kleist, E.; Guenther, K. Contribution to the structural elucidation of 10 isomers of technical p -nonylphenol Environ. Sci. Technol. 2004, 38 (12) 3405-3411
22. Wheeler, T. F.; Heim, J. R.; LaTorre, M. R.; Janes, A. B. Mass spectral characterization of p -nonylphenol isomers using high-resolution capillary GC-MS J. Chromatogr. Sci. 1997, 35 (1) 19-30
23. Zenkevich, I. G.; Makarov, A. A.; Schrader, S.; Moeder, M. A new version of an additive scheme for the prediction of gas chromatographic retention indices of the 211 structural isomers of 4-nonylphenol J. Chromatogr. A 2009, 1216 (18) 4097-4106
24. Cao, C. Z.; Liu, L. Topological steric effect index and its application J. Chem. Inf. Comput. Sci. 2004, 44 (2) 678-687
25. Hall, L. H.; Kellogg, G. E.; Haney, D. N. Software Package for Molecular Topology Analysis User'S Guide; 2008.
26. Todeschini, R.; Consonni, V.; Mannhold, R.; Kubinyi, H.; Folkers, G. Molecular Descriptors for Chemoinformatics; Wiley: New York, 2009.
27. Wold, S.; Sjöström, M.; Eriksson, L. PLS-regression: A basic tool of chemometrics Chemom. Intell. Lab. Syst. 2001, 58 (2) 109-130
28. Hao, R. X.; Li, J. B.; Zhou, Y. W.; Cheng, S. Y.; Zhang, Y. Structure-biodegradability relationship of nonylphenol isomers during biological wastewater treatment process Chemosphere 2009, 75 (8) 987-994
29. DeLaune, R. D.; Reddy, K. R. Redox potential. In Encyclopedia of Soils in the Environment; Daniel, H., Ed.; Elsevier: Oxford, 2005; pp 366-371.
30. Corvini, P. F. X.; Schaffer, A.; Schlosser, D. Microbial degradation of nonylphenol and other alkylphenols-Our evolving view Appl. Microbiol. Biotechnol. 2006, 72 (2) 223-243
31. Liu, Q.; Ji, R.; Hommes, G.; Schaffer, A.; Corvini, P. F. X. Fate of a branched nonylphenol isomer in submerged paddy soils amended with nitrate Water Res. 2008, 42 (19) 4802-4808
32. Guenther, K.; Kleist, E.; Thiele, B. Estrogen-active nonylphenols from an isomer-specific viewpoint: A systematic numbering system and future trends Anal. Bioanal. Chem. 2006, 384 (2) 542-6
33. Gabriel, F. L. P.; Giger, W.; Guenther, K.; Kohler, H. P. E. Differential degradation of nonylphenol isomers by Sphingomonas xenophaga bayram Appl. Environ. Microbiol. 2005, 71 (3) 1123-1129
34. Bonchev, D.; Trinajstic, N. Information theory, distance matrix, and molecular branching J. Chem. Phys. 1977, 67 (10) 4517-4533