博碩士論文 982404004 詳細資訊




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姓名 林怡雯(Yi-Wen Lin)  查詢紙本館藏   畢業系所 生命科學系
論文名稱 Brevibacterium sp. TX4 與 Pseudomonas nitroreducens TX1 異化辛基苯酚聚氧乙基醇及其代謝物之生物分解途徑研究
(Study of degradation pathway of octylphenol polyethoxylates by Brevibacterium sp. TX4 and octylphenol degradation by Pseudomonas nitroreducens TX1)
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摘要(中) 辛基苯酚聚氧乙基醇 (Octylphenol polyethoxylates, OPEOn) 屬於非離子性界面活性劑的一種,其一旦被排放至自然環境中,經常會生成為更不易分解且具環境賀爾蒙效力的代謝產物如辛基苯酚 (octylphenol) 與帶1-2單位氧乙基醇之辛基苯酚聚氧乙基醇,對於人體健康與環境生態具危害性。黃雪莉教授研究團隊先前從農藥工廠、稻田及中央大學排放水的表土及底泥中分離出43株可以辛基苯酚聚氧乙基醇為唯一碳源培養之菌株,其中Brevibacterium sp. TX4 為唯一的一株格蘭氏陽性菌。以高效能液相層析質譜儀 (HPLC-MS) 分析菌株TX4分解辛基苯酚聚氧乙基醇的代謝產物,推斷此菌株能在耗氧的情況下減短聚氧乙烯鏈,Brevibacterium sp. TX4為第一株被發現據此能力的格蘭氏陽性菌。
另外,在43株具分解辛基苯酚聚氧乙基醇能力的菌株中,Pseudomonas nitroreducens TX1生長速率最快且對辛基苯酚聚氧乙基醇的耗氧活性最高,並能生長在0.05%到20%的辛基苯酚聚氧乙基醇濃度中,其生長速率在0.34到0.44 hr-1之間。以高效能液相層析質譜儀 (HPLC-MS) 分析菌株TX1分解辛基苯酚聚氧乙基醇的代謝產物,推斷此菌株能減短聚氧乙烯鏈並生成辛基苯酚。本研究發現菌株TX1可以進一步以支鏈型辛基苯酚 (4-t-octylphenol) 為唯一碳源生長。P. nitroreducens TX1為第一株被發現同時具有分解辛基苯酚聚氧乙基醇與支鏈型辛基苯酚能力的菌株。以高效能液相層析質譜儀 (LC-ESI-Q-TOF) 分析此菌株以支鏈型辛基苯酚為唯一碳源生長過程中的代謝產物,發現有中間代謝物辛基鄰苯二酚 (4-t-octylcatechol) 生成。其中偵測到兩個經間位裂解 (meta-cleavage) 途徑產生之代謝物: 5-formyl-2-hydroxy-6,6,8,8-tetramethylnona-2,4-dienoic acid 與 6,6,8,8-tetramethyl-2-oxonon-4-enoic acid,推測菌株TX1分解支鏈型辛基苯酚的過程首先藉由苯環羥化 (aromatic ring hydroxylation) 產生辛基鄰苯二酚,再經由間位裂解途徑以破壞辛基苯酚之結構進而降低環境賀爾蒙效力。除此之外,在菌株TX1分解支鏈型辛基苯酚的過程中發現有O-甲基化 (O-methylation) 的反應進行。生長實驗中測定菌株TX1對其他不同類型之烷基苯酚 (4-alkylphenols) 之利用特性,發現菌株TX1可利用廣泛不同類型之烷基苯酚,尤其是長鏈烷基苯酚。因此,菌株TX1具有應用於分解環境中之辛基苯酚聚氧乙基醇與不同類型之烷基苯酚污染物之潛力。
摘要(英) Octylphenol polyethoxylates (OPEOn) are surfactants and prone to be degraded into xenoestrogenic metabolites, such as octylphenol and OPEOn (n=1-2), are estrogenic-like compounds, and persistent to be degraded by bacteria in the environments. Due to the structural similarity to estradiol, nonylphenols/octylphenols influenced the growth, reproduction and sexual development of humans and animals, therefore, causing health and ecological concern. Forty three bacterial strains were isolated from soil and sediments of a pesticide factory, a rice field, and drainage of a dormitory by Huang’s group can utilize OPEOn as their sole carbon and energy source. Brevibacterium sp. TX4 was the only Gram-positive bacterium. Metabolites analysis by HPLC/MS revealed that Brevibacterium sp. TX4 could shorten the ethoxylate chain thereby degrading OPEOn, during which O2 was required. Brevibacterium sp. TX4 is the first Gram-positive bacterium which was demonstrated to shorten the ethoxylate chain of OPEOn.
Among the isolates, Pseudomonas nitroreducens TX1 can grow on 0.05% to 20% of OPEOn with a specific growth rate of 0.34-0.44 hr-1. High-performance liquid chromatography–mass spectrometer analysis of OPEOn degraded metabolites revealed that strain TX1 was able to shorten the ethoxylate chain and produce octylphenol (OP). This study showed that P. nitroreducens TX1 was capable of utilizing 4-t-octylphenol, the endocrine disrupting compound, as a sole carbon source. This strain is the first bacterium which is able to degrade both octylphenol polyethoxylates (OPEOn) and 4-t-octylphenol to be reported. Along with the degradation of 4-t-octylphenol, 4-t-octylcatechol was identified as internal metabolite. Two key metabolites of the meta-cleavage pathway, 5-formyl-2-hydroxy-6,6,8,8-tetramethylnona-2,4-dienoic acid and 6,6,8,8-tetramethyl-2-oxonon-4-enoic acid, were detected by LC-ESI-Q-TOF. We concluded that degradation of 4-t-octylphenol by strain TX1 is initiated by aromatic ring hydroxylation to form 4-t-octylcatechol, followed by a meta-cleavage pathway thereby to disrupting the estrogenic activity of 4-t-octylphenol. In addition to the degradation reactions, O-methylation was observed during the 4-t-octylphenol degradation by strain TX1. Growth experiments with other 4-alkylphenols showed that strain TX1 could utilize a wide range of 4-alkylphenols, especially the long chain alkylphenols. Therefore, strain TX1 has potential be used in the bioremediation of environments polluted by OPEOn, 4-t-octylphenol and various other 4-alkylphenols.
關鍵字(中) ★ 辛基苯酚聚氧乙基醇
★ 辛基苯酚
★ 生物分解途徑
★ Brevibacterium sp. TX4
★ Pseudomonas nitroreducens TX1
關鍵字(英) ★ octylphenol polyethoxylates
★ octylphenol
★ degradation pathway
★ Brevibacterium sp. TX4
★ Pseudomonas nitroreducens TX1
論文目次 中文摘要 I
Abstract III
致謝 V
Table of Contents VI
List of Figures X
List of Tables XII
Abbreviations XIII
Chapter 1. Background and Goals 1
1.1 General concepts in biodegradation and biotransformation 2
1.2 Endocrine disrupting compounds 2
1.3 Alkylphenol polyethoxylates 3
1.3.1 Structure 4
1.3.2 Application 4
1.4 Biodegradation of alkylphenol polyethoxylates 5
1.4.1 Bacterial strains 5
1.4.2 exo-scission of ethoxylate chain 9
1.4.3 Alkyl chain hydroxylation 11
1.5 Long-chain alkylphenol (octylphenol and nonylphenol) 12
1.5.1 Structure 12
1.5.2 Sources 13
1.5.3 Distribution 14
1.5.3.1 Distribution of octylphenol and nonylphenol in the environments 14
1.5.3.2 Drinking water and food 20
1.5.3.3 Human exposure and alkylphenols detected in human body 20
1.5.3.3.1 Octylphenol and nonylphenol detected in human adipose tissue 21
1.5.3.3.2 Octylphenol and nonylphenol in human urine and plasma 22
1.5.3.3.3 Octylphenol and nonylphenol in human umbilical cord blood and breast milk 22
1.5.4 Adverse health effect 23
1.5.5 Controlling legislation and international agreements 25
1.6 Transformation of octylphenol/nonylphenol in fish and rats 26
1.6.1 Hydroxylation of the aromatic ring to form catechols and catechol O-methylation 29
1.6.2 Hydroxylation of alkyl chain via ω-oxidation and β-oxidation 30
1.6.3 Glucuronidation and de-conjugation 30
1.7 Transformation of octylphenol/nonylphenol by plants 31
1.8 Transformation of octylphenol/nonylphenol by fungi and yeast 33
1.8.1 Fungi and yeast isolates 33
1.8.2 Oxidative enzymes from fungi 34
1.8.3 Alkyl chain hydroxylation 36
1.9 Degradation of octylphenol/nonylphenol by bacteria 39
1.9.1 Bacterial isolates 39
1.9.2 Passage of hydrophobic substrates across the bacterial cell membrane 41
1.9.3 Mechanisms and oxygenases involved in long-chain alkylphenol ring degradation 43
1.9.3.1 Fission of the alkyl chain and phenol ring: ipso hydroxylation and single-component monooxygenase 45
1.9.3.2 Aromatic ring hydroxylation and ring fission 50
1.9.3.2.1 Aromatic ring hydroxylation: multicomponent phenol hydroxylase 53
1.9.3.2.2 Aromatic ring hydroxylation: cytochrome P450 monooxygeneses 55
1.9.3.2.3 Aromatic ring fission: catechol 2,3-dioxygenase 60
1.9.4 Alkyl chain hydroxylation 62
1.9.5 Anaerobic degradation 67
1.10 Research aims 67
Chapter 2. Aerobic degradation of alkylphenol polyethoxylates via cleavage of polyethoxylate chain by Brevibacterium sp. TX4 69
2.1 Introduction 69
2.2 A review of previous work 71
2.2.1 Isolation and identification of OPEOn-degrading bacteria 71
2.2.2 The diversity of enriched isolates 71
2.2.3 OPEOn degradation pathway in P. nitroreducens TX1 73
2.3 Materials and Methods 75
2.3.1 Media 75
2.3.2 16S rRNA Gene Sequencing and Phylogenetic Analysis 76
2.3.3 Carbon source utilization of Brevibacterium sp. TX4 76
2.3.4 Oxygen consumption 76
2.3.5 Identification of metabolites from OPEOn biodegradation 77
2.4 Result
2.4.1 Identification of Brevibacterium sp. TX4 78
2.4.2 Growth of Brevibacterium sp. TX4 on OPEOn and related carbon source 78
2.4.3 Oxygen consumption activity of Brevibacterium sp. TX4 79
2.4.4 Biodegradation kinetics of OPEOn by Brevibacterium sp. TX4 79
2.5 Discussion 83
2.6 Conclusion 88
Chapter 3. Degradation of 4-t-octylphenol via aromatic ring hydroxylation and meta-cleavage pathway by Pseudomonas nitroreducens TX1 89
3.1 Introduction 89
3.2 Materials and Methods 93
3.2.1 Chemicals 93
3.2.2 Bacterium and medium 93
3.2.3 Carbon source utilization of 4-alkylphenols and 4-alkylcatechols 94
3.2.4 Analysis of the metabolites obtained from the biodegradation of 4-t-octylphenol 94
3.2.5 Estrogenic activity assay 100
3.2.6 Inhibition of Pseudomonas sp. TX1 growth by metyrapone 101
3.2.7 Enzyme structure prediction and molecule docking 103
3.3 Result 103
3.3.1 Growth of strain TX1 on various 4-alkylphenols and 4-alkylcatechols 103
3.3.2 Biodegradation kinetics of 4-t-octylphenol by strain TX1 105
3.3.3 Estrogenic activity assay 106
3.3.4 Analysis of the metabolites obtained from the biodegradation of
4-t-octylphenol 107
3.3.5 Structure prediction of cytochrome P450 in strain TX1 108
3.3.6 Inhibition of 4-t-octylphenol degradation by metyrapone 112
3.4 Discussion 113
3.5 Conclusion 121
Chapter 4 Conclusion 122
References 126
Appendixes
A1. Paper published:
Yi-Wen Lin, Chia-Chin Yang, Nguyen Ngoc Tuan, Shir-Ly Huang*. 2016. Diversity of octylphenol polyethoxylate-degrading bacteria: with a special reference to Brevibacterium sp. TX4. International Biodeterioration & Biodegradation 115, 55-63.
A2. Paper published:
Yi-Wen Lin, Nguyen Ngoc Tuan, Shir-Ly Huang*. 2016. Metaproteomic analysis of the microbial community present in a thermophilic swine manure digester to allow functional characterization: a case study. International Biodeterioration & Biodegradation 115, 64-73
A3. Paper published:
Nguyen Ngoc Tuan, Yi Wen Lin, Shir Ly Huang*. 2013. Catabolism of 4-alkylphenols by Acinetobacter sp. OP5: Genetic organization of the oph gene cluster and characterization of alkylcatechol 2, 3-dioxygenase.Bioresource Technology 131, 420-428.
A4. Paper published:
Nguyen Ngoc Tuan, Hsiao Cheng Hsieh, Yi Wen Lin, and Shir Ly Huang*. 2011. Analysis of bacterial degradation pathways for long-chain alkylphenols involving phenol hydroxylase, alkylphenol monooxygenase and catechol dioxygenase genes. Bioresource Technology 102, 4232-40.
A5. Paper published:
Yi-Wen Lin, Gia-Luen Guo, Hsiao-Cheng Hsieh, Shir-Ly Huang*. 2010. Growth of Pseudomonas sp. TX1 on a wide range of octylphenol polyethoxylate concentrations and the formation of dicarboxylated metabolites. Bioresource Technology 101, 2853-2859.
參考文獻 王正雄、張小萍、黃任瑰、李宜樺、王世冠、洪文宗、陳珮珊。2002。環境荷爾蒙-壬基苯酚殘留調查及其對雄鯉魚生理效應之研究。環境檢驗所環境調查研究年報第九期。
Ademollo, N., Ferrara, F., Delise, M., Fabietti, F., Funari, E. 2008. Nonylphenol and octylphenol in human breast milk. Environ Int, 34(7), 984-7.
Ahel, M., Giger, W. 1993. Aqueous solubility of alkylphenols and alkylphenol polyethoxylates. Chemosphere, 26(8), 1461-70.
Ahel, M., Giger, W., Schaffner, C. 1994. Behavior of alkylphenol polyethoxylate surfactants in the aquatic environment .2. occurrence and transformation in rivers. Water Research, 28(5), 1143-52.
Allard, A.S., Remberger, M., Neilson, A.H. 1987. Bacterial O-methylation of halogen-substituted phenols. Appl Environ Microbiol, 53(4), 839-45.
Alonso, H., Kleifeld, O., Yeheskel, A., Ong, P.C., Liu, Y.C., Stok, J.E., De Voss, J.J., Roujeinikova, A. 2014. Structural and mechanistic insight into alkane hydroxylation by Pseudomonas putida AlkB. Biochem J, 460(2), 283-93.
Amann, R.I., Ludwig, W., Schleifer, K.H. 1995. Phylogenetic identification and in situ detection of individual microbial cells without cultivation. Microbiol Rev, 59(1), 143-69.
Anfinsen, C.B. 1973. Principles that govern the folding of protein chains. Science, 181(4096), 223-30.
Arai, H., Akahira, S., Ohishi, T., Maeda, M., Kudo, T. 1998. Adaptation of Comamonas testosteroni TA441 to utilize phenol: organization and regulation of the genes involved in phenol degradation. Microbiology, 144 ( Pt 10), 2895-903.
Arnold, K., Bordoli, L., Kopp, J., Schwede, T. 2006. The SWISS-MODEL workspace: a web-based environment for protein structure homology modelling. Bioinformatics, 22(2), 195-201.
Arukwe, A., Thibaut, R., Ingebrigtsen, K., Celius, T., Goksoyr, A., Cravedi, J.P. 2000. In vivo and in vitro metabolism and organ distribution of nonylphenol in Atlantic salmon (Salmo salar). Aquatic Toxicology, 49(4), 289-304.
Baker, D., Sali, A. 2001. Protein structure prediction and structural genomics. Science, 294(5540), 93-6.
Ball, P., Knuppen, R. 1980. Catecholoestrogens (2-and 4-hydroxyoestrogens): chemistry, biogenesis, metabolism, occurrence and physiological significance. Acta Endocrinol Suppl (Copenh), 232, 1-127.
Barber, L.B., Loyo-Rosales, J.E., Rice, C.P., Minarik, T.A., Oskouie, A.K. 2015. Endocrine disrupting alkylphenolic chemicals and other contaminants in wastewater treatment plant effluents, urban streams, and fish in the Great Lakes and Upper Mississippi River Regions. Sci Total Environ, 517, 195-206.
Barberio, C., Pagliai, L., Cavalieri, D., Fani, R. 2001. Biodiversity and horizontal gene transfer in culturable bacteria isolated from activated sludge enriched in nonylphenol ethoxylates. Res Microbiol, 152(1), 105-12.
Blake, C.A., Boockfor, F.R. 1997. Chronic administration of the environmental pollutant 4-tert-octylphenol to adult male rats interferes with the secretion of luteinizing hormone, follicle-stimulating hormone, prolactin, and testosterone. Biol Reprod, 57(2), 255-66.
Bodo, A., Bakos, E., Szeri, F., Varadi, A., Sarkadi, B. 2003. Differential modulation of the human liver conjugate transporters MRP2 and MRP3 by bile acids and organic anions. Journal of Biological Chemistry, 278(26), 23529-37.
Bokern, M., Nimtz, M., Harms, H.H. 1996. Metabolites of 4-n-nonylphenol in wheat cell suspension cultures. Journal of Agricultural and Food Chemistry, 44(4), 1123-7.
Bonefeld-Jorgensen, E.C., Long, M.H., Hofmeister, M.V., Vinggaard, A.M. 2007. Endocrine-disrupting potential of bisphenol A, bisphenol A dimethacrylate, 4-n-nonylphenol, and 4-n-octylphenol in vitro: new data and a brief review. Environ Health Perspect, 115, 69-76.
Cabana, H., Jiwan, J.L.H., Rozenberg, R., Elisashvili, V., Penninckx, M., Agathos, S.N., Jones, J.P. 2007a. Elimination of endocrine disrupting chemicals nonylphenol and bisphenol A and personal care product ingredient triclosan using enzyme preparation from the white rot fungus Coriolopsis polyzona. Chemosphere, 67(4), 770-778.
Cabana, H., Jones, J.P., Agathos, S.N. 2007b. Preparation and characterization of cross-linked laccase aggregates and their application to the elimination of endocrine disrupting chemicals. Journal of Biotechnology, 132(1), 23-31.
Cespedes, R., Lacorte, S., Ginebreda, A., Barcelo, D. 2006. Chemical monitoring and occurrence of alkylphenols, alkylphenol ethoxylates, alcohol ethoxylates, phthalates and benzothiazoles in sewage treatment plants and receiving waters along the Ter River basin (Catalonia, N. E. Spain). Anal Bioanal Chem, 385(6), 992-1000.
Chang, B.V., Chiang, B.W., Yuan, S.Y. 2007. Biodegradation of nonylphenol in soil. Chemosphere, 66(10), 1857-62.
Chang, B.V., Yu, C.H., Yuan, S.Y. 2004. Degradation of nonylphenol by anaerobic microorganisms from river sediment. Chemosphere, 55(4), 493-500.
Chen, H.J., Guo, G.L., Tseng, D.H., Cheng, C.L., Huang, S.L. 2006. Growth factors, kinetics and biodegradation mechanism associated with Pseudomonas nitroreducens TX1 grown on octylphenol polyethoxylates. Journal of Environmental Management, 80(4), 279-86.
Chen, H.J., Tseng, D.H., Huang, S.L. 2005a. Biodegradation of octylphenol polyethoxylate surfactant Triton X-100 by selected microorganisms. Bioresource Technology, 96(13), 1483-91.
Chen, M.L., Chang, C.C., Shen, Y.J., Hung, J.H., Guo, B.R., Chuang, H.Y., Mao, I.F. 2008. Quantification of prenatal exposure and maternal-fetal transfer of nonylphenol. Chemosphere, 73(1), S239-S245.
Chen, M.L., Lee, W.P., Chung, H.Y., Guo, B.R., Mao, I.F. 2005b. Biornonitoring of alkylphenols exposure for textile and housekeeping workers. International Journal of Environmental Analytical Chemistry, 85(4-5), 335-47.
Cheng, C.Y., Li, W.R., Chang, J.W., Wu, H.C., Ding, W.H. 2006a. Synthesis and determination of dicarboxylic degradation products of nonylphenol polyethoxylates by gas chromatography-mass spectrometry. J Chromatogr A, 1127(1-2), 246-53.
Cheng, C.Y., Liu, L.L., Ding, W.H. 2006b. Occurrence and seasonal variation of alkylphenols in marine organisms from the coast of Taiwan. Chemosphere, 65(11), 2152-9.
Cheng, C.Y., Wu, C.Y., Wang, C.H., Ding, W.H. 2006c. Determination and distribution characteristics of degradation products of nonylphenol polyethoxylates in the rivers of Taiwan. Chemosphere, 65(11), 2275-81.
Chiu, T.S., Hsieh, C.Y., Miaw, C.L., Lin, C.N., Chang, T.C., Yen, C.H., Chiou, M.T. 2014. Alkylphenol polyethoxylate derivatives in groundwater and blood samples collected from pig herds in Taiwan. J Vet Med Sci, 76(7), 971-5.
Cho, J.H., Jung, D.K., Lee, K., Rhee, S. 2009. Crystal structure and functional analysis of the extradiol dioxygenase LapB from a long-chain alkylphenol degradation pathway in Pseudomonas. J Biol Chem, 284(49), 34321-30.
Chothia, C. 1992. Proteins. One thousand families for the molecular biologist. Nature, 357(6379), 543-4.
Coleman, N.V., Spain, J.C., Duxbury, T. 2002. Evidence that RDX biodegradation by Rhodococcus strain DN22 is plasmid-borne and involves a cytochrome p-450. J Appl Microbiol, 93(3), 463-72.
Collado, N., Buttiglieri, G., Kolvenbach, B.A., Comas, J., Corvini, P.F., Rodriguez-Roda, I. 2013. Exploring the potential of applying proteomics for tracking bisphenol A and nonylphenol degradation in activated sludge. Chemosphere, 90(8), 2309-14.
Correia, M.A., Monteflano, P.R.O.d. 2004. Cytochrome P450: Structure, Mechanism, and Biochemistry. Springer.
Corti, A., Frassinetti, S., Vallini, G., D′Antone, S., Fichi, C., Solaro, R. 1995. Biodegradation of nonionic surfactants. I. Biotransformation of 4-(1-nonyl)phenol by a Candida maltosa isolate. Environ Pollut, 90(1), 83-7.
Corvini, P.F., Hollender, J., Ji, R., Schumacher, S., Prell, J., Hommes, G., Priefer, U., Vinken, R., Schaffer, A. 2006a. The degradation of alpha-quaternary nonylphenol isomers by Sphingomonas sp. strain TTNP3 involves a type II ipso-substitution mechanism. Appl Microbiol Biotechnol, 70(1), 114-22.
Corvini, P.F., Meesters, R., Mundt, M., Schaffer, A., Schmidt, B., Schroder, H.F., Verstraete, W., Vinken, R., Hollender, J. 2007. Contribution to the detection and identification of oxidation metabolites of nonylphenol in Sphingomonas sp. strain TTNP3. Biodegradation, 18(2), 233-45.
Corvini, P.F., Meesters, R.J., Schaffer, A., Schroder, H.F., Vinken, R., Hollender, J. 2004a. Degradation of a nonylphenol single isomer by Sphingomonas sp. strain TTNP3 leads to a hydroxylation-induced migration product. Appl Environ Microbiol, 70(11), 6897-900.
Corvini, P.F., Schaffer, A., Schlosser, D. 2006b. Microbial degradation of nonylphenol and other alkylphenols--our evolving view. Appl Microbiol Biotechnol, 72(2), 223-43.
Corvini, P.F., Vinken, R., Hommes, G., Mundt, M., Hollender, J., Meesters, R., Schroder, H.F., Schmidt, B. 2004b. Microbial degradation of a single branched isomer of nonylphenol by Sphingomonas TTNP3. Water Sci Technol, 50(5), 189-94.
Corvini, P.F.X., Elend, M., Hollender, J., Ji, R., Preiss, A., Vinken, R., Schaffer, A. 2005. Metabolism of a nonylphenol isomer by Sphingomonas sp strain TTNP3. Environmental Chemistry Letters, 2(4), 185-9.
Crago, J., Tran, K., Budicin, A., Schreiber, B., Lavado, R., Schlenk, D. 2015. Exploring the impacts of two separate mixtures of pesticide and surfactants on estrogenic activity in male fathead minnows and rainbow trout. Arch Environ Contam Toxicol, 68(2), 362-70.
Daidoji, T., Inoue, H., Kato, S., Yokota, H. 2003. Glucuronidation and excretion of nonylphenol in perfused rat liver. Drug Metabolism and Disposition, 31(8), 993-8.
Di Corcia, A., Cavallo, R., Crescenzi, C., Nazzari, M. 2000. Occurrence and abundance of dicarboxylated metabolites of nonylphenol polyethoxylate surfactants in treated sewages. Environmental Science & Technology, 34(18), 3914-9.
Di Corcia, A., Costantino, A., Crescenzi, C., Marinoni, E., Samperi, R. 1998. Characterization of recalcitrant intermediates from biotransformation of the branched alkyl side chain of nonylphenol ethoxylate surfactants. Environmental Science & Technology, 32(16), 2401-9.
Di Gioia, D., Fambrini, L., Coppini, E., Fava, F., Barberio, C. 2004. Aggregation-based cooperation during bacterial aerobic degradation of polyethoxylated nonylphenols. Res Microbiol, 155(9), 761-9.
Ding, W.H., Fujita, Y., Aeschimann, R., Reinhard, M. 1996. Identification of organic residues in tertiary effluents by GC/EI-MS, GC/CI-MS and GC/TSQ-MS. Fresenius Journal of Analytical Chemistry, 354(1), 48-55.
Ding, W.H., Tzing, S.H., Lo, J.H. 1999. Occurrence and concentrations of aromatic surfactants and their degradation products in river waters of Taiwan. Chemosphere, 38(11), 2597-606.
Dixon, B. 1996. Cheese, toes, and mosquitoes. BMJ, 312(7038), 1105.
Endo, Y., Xuan, Y.J., Fujimoto, K. 2000. The oxidation of p-octylphenol by mushroom tyrosinase. Nippon Nogeikagaku Kaishi-Journal of the Japan Society for Bioscience Biotechnology and Agrochemistry, 74(12), 1337-41.
Farnet, A.M., Chevremont, A.C., Gil, G., Gastaldi, S., Ferre, E. 2011. Alkylphenol oxidation with a laccase from a white-rot fungus: effects of culture induction and of ABTS used as a mediator. Chemosphere, 82(2), 284-9.
Ferrara, F., Ademollo, N., Orru, M.A., Silvestroni, L., Funari, E. 2011. Alkylphenols in adipose tissues of Italian population. Chemosphere, 82(7), 1044-9.
Ferrara, F., Fabietti, F., Delise, M., Funari, E. 2005. Alkylphenols and alkylphenol ethoxylates contamination of crustaceans and fishes from the Adriatic Sea (Italy). Chemosphere, 59(8), 1145-50.
Franska, M., Franski, R., Szymanski, A., Lukaszewski, Z. 2003. A central fission pathway in alkylphenol ethoxylate biodegradation. Water Res, 37(5), 1005-14.
Fujii, K., Urano, N., Ushio, H., Satomi, M., Kimura, S. 2001. Sphingomonas cloacae sp. nov., a nonylphenol-degrading bacterium isolated from wastewater of a sewage-treatment plant in Tokyo. Int J Syst Evol Microbiol, 51(Pt 2), 603-10.
Gabriel, F.L., Cyris, M., Giger, W., Kohler, H.P. 2007a. ipso-substitution: a general biochemical and biodegradation mechanism to cleave alpha-quaternary alkylphenols and bisphenol A. Chem Biodivers, 4(9), 2123-37.
Gabriel, F.L., Cyris, M., Jonkers, N., Giger, W., Guenther, K., Kohler, H.P. 2007b. Elucidation of the ipso-substitution mechanism for side-chain cleavage of alpha-quaternary 4-nonylphenols and 4-t-butoxyphenol in Sphingobium xenophagum Bayram. Appl Environ Microbiol, 73(10), 3320-6.
Gabriel, F.L., Giger, W., Guenther, K., Kohler, H.P. 2005a. Differential degradation of nonylphenol isomers by Sphingomonas xenophaga Bayram. Appl Environ Microbiol, 71(3), 1123-9.
Gabriel, F.L., Heidlberger, A., Rentsch, D., Giger, W., Guenther, K., Kohler, H.P. 2005b. A novel metabolic pathway for degradation of 4-nonylphenol environmental contaminants by Sphingomonas xenophaga Bayram: ipso-hydroxylation and intramolecular rearrangement. J Biol Chem, 280(16), 15526-33.
Gabriel, F.L., Routledge, E.J., Heidlberger, A., Rentsch, D., Guenther, K., Giger, W., Sumpter, J.P., Kohler, H.P. 2008. Isomer-specific degradation and endocrine disrupting activity of nonylphenols. Environ Sci Technol, 42(17), 6399-408.
Gibson, D.T. 1993. Biodegradation, biotransformation and the belmont. Journal of Industrial Microbiology, 12(1), 1-12.
Giger, W., Gabriel, F.L., Jonkers, N., Wettstein, F.E., Kohler, H.P. 2009. Environmental fate of phenolic endocrine disruptors: field and laboratory studies. Philos Transact A Math Phys Eng Sci, 367(1904), 3941-63.
Gray, M.A., Metcalfe, C.D. 1997. Induction of testis-ova in Japanese medaka (Oryzias latipes) exposed to p-nonylphenol. Environmental Toxicology and Chemistry, 16(5), 1082-6.
Griva, E., Pessione, E., Divari, S., Valetti, F., Cavaletto, M., Rossi, G.L., Giunta, C. 2003. Phenol hydroxylase from Acinetobacter radioresistens S13. Isolation and characterization of the regulatory component. Eur J Biochem, 270(7), 1434-40.
Gronen, S., Denslow, N., Manning, S., Barnes, S., Barnes, D., Brouwer, M. 1999. Serum vitellogenin levels and reproductive impairment of male Japanese Medaka (Oryzias latipes) exposed to 4-tert-octylphenol. Environ Health Perspect, 107(5), 385-90.
Gu, X., Zhang, Y., Zhang, J., Yang, M., Tamaki, H., Kamagata, Y., Li, D. 2010. Isolation of phylogenetically diverse nonylphenol ethoxylate-degrading bacteria and characterization of their corresponding biotransformation pathways. Chemosphere, 80(3), 216-22.
Guenther, K., Heinke, V., Thiele, B., Kleist, E., Prast, H., Raecker, T. 2002. Endocrine disrupting nonylphenols are ubiquitous in food. Environmental Science & Technology, 36(8), 1676-80.
Haggblom, M. 1990. Mechanisms of bacterial degradation and transformation of chlorinated monoaromatic compounds. J Basic Microbiol, 30(2), 115-41.
Haines, J.R., Alexander, M. 1975. Microbial degradation of polyethylene glycols. Appl Microbiol, 29(5), 621-5.
Harayama, S., Kok, M., Neidle, E.L. 1992. Functional and evolutionary relationships among diverse oxygenases. Annual Review of Microbiology, 46, 565-601.
Harayama, S., Rekik, M. 1989. Bacterial aromatic ring-cleavage enzymes are classified into two different gene families. J Biol Chem, 264(26), 15328-33.
Harries, J.E., Sheahan, D.A., Jobling, S., Matthiessen, P., Neall, M., Sumpter, J.P., Taylor, T., Zaman, N. 1997. Estrogenic activity in five United Kingdom rivers detected by measurement of vitellogenesis in caged male trout. Environmental Toxicology and Chemistry, 16(3), 534-42.
Harris, C.A., Santos, E.M., Janbakhsh, A., Pottinger, T.G., Tyler, C.R., Sumpter, J.P. 2001. Nonylphenol affects gonadotropin levels in the pituitary gland and plasma of female rainbow trout. Environ Sci Technol, 35(14), 2909-16.
Hayaishi, O. 1974. Bacterial enzymology: adenylate cyclase. Nihon Saikingaku Zasshi, 29(1), 30.
Hearn, E.M., Patel, D.R., van den Berg, B. 2008. Outer-membrane transport of aromatic hydrocarbons as a first step in biodegradation. Proc Natl Acad Sci U S A, 105(25), 8601-6.
Helenius, A., Simons, K. 1975. Solubilization of membranes by detergents. Biochimica et Biophysica Acta (BBA) - Reviews on Biomembranes, 415(1), 29-79.
Herrmann, H., Muller, C., Schmidt, I., Mahnke, J., Petruschka, L., Hahnke, K. 1995. Localization and organization of phenol degradation genes of Pseudomonas putida strain H. Mol Gen Genet, 247(2), 240-6.
Hino, S., Watanabe, K., Takahashi, N. 1998. Phenol hydroxylase cloned from Ralstonia eutropha strain E2 exhibits novel kinetic properties. Microbiology, 144 ( Pt 7), 1765-72.
Hopper, D.J., Cottrell, L. 2003. Alkylphenol biotransformations catalyzed by 4-ethylphenol methylenehydroxylase. Appl Environ Microbiol, 69(6), 3650-2.
Hotta, Y., Hosoda, A., Sano, F., Wakayama, M., Niwa, K., Yoshikawa, H., Tamura, H. 2010. Ecotoxicity by the biodegradation of alkylphenol polyethoxylates depends on the effect of trace elements. J Agric Food Chem, 58(2), 1062-7.
Hugo, N., Armengaud, J., Gaillard, J., Timmis, K.N., Jouanneau, Y. 1998. A novel -2Fe-2S- ferredoxin from Pseudomonas putida mt2 promotes the reductive reactivation of catechol 2,3-dioxygenase. J Biol Chem, 273(16), 9622-9.
Iizuka, H., Komagata, K. 1964. Microbiological studies on petroleum and natural gas i. Determination of hydrocarbon-utilizing bacteria. The Journal of General and Applied Microbiology, 10(3), 207-21.
Ikeda, N., Yamada, K., Shibuya, T., Kashiwada, A., Matsuda, K., Hirata, M. 2008. Removal of linear and branched alkylphenols from aqueous solutions with horseradish peroxidase. Bioscience Biotechnology and Biochemistry, 72(5), 1368-71.
Inoue, K., Kondo, S., Yoshie, Y., Kato, K., Yoshimura, Y., Horie, M., Nakazawa, H. 2001. Migration of 4-nonylphenol from polyvinyl chloride food packaging films into food simulants and foods. Food Addit Contam, 18(2), 157-64.
Jeong, J.J., Kim, J.H., Kim, C.K., Hwang, I., Lee, K. 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(Pt 11), 3265-77.
Jing, X., Bing, S., Xiaoyan, W., Xiaojie, S., Yongning, W. 2011. A study on bisphenol A, nonylphenol, and octylphenol in human urine amples detected by SPE-UPLC-MS. Biomed Environ Sci, 24(1), 40-6.
Jobling, S., Sheahan, D., Osborne, J.A., Matthiessen, P., Sumpter, J.P. 1996. Inhibition of testicular growth in rainbow trout (Oncorhynchus mykiss) exposed to estrogenic alkylphenolic chemicals. Environmental Toxicology and Chemistry, 15(2), 194-202.
Jobling, S., Sumpter, J.P. 1993. Detergent components in sewage effluent are weakly estrogenic to fish - an in-vitro study using rainbow-trout (Oncorhynchus-Mykiss) Hepatocytes. Aquatic Toxicology, 27(3-4), 361-72.
John, D.M., White, G.F. 1998. Mechanism for biotransformation of nonylphenol polyethoxylates to Xenoestrogens in Pseudomonas putida. J Bacteriol, 180(17), 4332-8.
Johnson, E.L., Hyman, M.R. 2006. Propane and n-butane oxidation by Pseudomonas putida GPo1. Appl Environ Microbiol, 72(1), 950-2.
Junghanns, C., Moeder, M., Krauss, G., Martin, C., Schlosser, D. 2005. Degradation of the xenoestrogen nonylphenol by aquatic fungi and their laccases. Microbiology, 151(Pt 1), 45-57.
Karci, A. 2014. Degradation of chlorophenols and alkylphenol ethoxylates, two representative textile chemicals, in water by advanced oxidation processes: the state of the art on transformation products and toxicity. Chemosphere, 99, 1-18.
Kawaguchi, M., Ishii, Y., Sakui, N., Okanouchi, N., Ito, R., Inoue, K., Saito, K., Nakazawa, H. 2004. Stir bar sorptive extraction with in situ derivatization and thermal desorption-gas chromatography-mass spectrometry in the multi-shot mode for determination of estrogens in river water samples. J Chromatogr A, 1049(1-2), 1-8.
Kawai, F. 1996. Bacterial degradation of a new polyester, polyethylene glycol-phthalate polyester. Journal of environmental polymer degradation, 4(1), 21-8.
Kawai, F., Kimura, T., Tani, Y., Yamada, H., Kurachi, M. 1980. Purification and characterization of polyethylene glycol dehydrogenase involved in the bacterial metabolism of polyethylene glycol. Appl Environ Microbiol, 40(4), 701-5.
Knaak, J.B., Eldridge, J.M., Sullivan, L.J. 1966. Excretion of certain polyethylene glycol ether adducts of nonylphenol by the rat. Toxicol Appl Pharmacol, 9(2), 331-40.
Kohlweyer, U., Thiemer, B., Schrader, T., Andreesen, J.R. 2000. Tetrahydrofuran degradation by a newly isolated culture of Pseudonocardia sp. strain K1. FEMS Microbiol Lett, 186(2), 301-6.
Kolvenbach, B., Schlaich, N., Raoui, Z., Prell, J., Zuhlke, S., Schaffer, A., Guengerich, F.P., Corvini, P.F. 2007. Degradation pathway of bisphenol A: does ipso substitution apply to phenols containing a quaternary alpha-carbon structure in the para position? Appl Environ Microbiol, 73(15), 4776-84.
Kovacs, J.A. 2003. Biochemistry. How iron activates O2. Science, 299(5609), 1024-5.
Kweon, O., Kim, S.J., Jones, R.C., Freeman, J.P., Adjei, M.D., Edmondson, R.D., Cerniglia, C.E. 2007. A polyomic approach to elucidate the fluoranthene-degradative pathway in Mycobacterium vanbaalenii PYR-1. J Bacteriol, 189(13), 4635-47.
Lazarow, P.B. 1978. Rat liver peroxisomes catalyze the beta oxidation of fatty acids. J Biol Chem, 253(5), 1522-8.
Lee, H.J., Lian, L.Y., Scrutton, N.S. 1997. Recombinant two-iron rubredoxin of Pseudomonas oleovorans: overexpression, purification and characterization by optical, CD and 113Cd NMR spectroscopies. Biochem J, 328(Pt 1), 131-6.
Li, C.T., Cheng, C.Y., Ding, W.H. 2008. Determination of alkylphenol residues in baby-food purees by steam distillation extraction and gas chromatography-mass spectrometry. Food and Chemical Toxicology, 46(2), 803-7.
Li, X.L., Luan, T.G., Liang, Y., Wong, M.H., Lan, C.Y. 2007. Distribution patterns of octylphenol and nonylphenol in the aquatic system at mai po marshes nature reserve, a subtropical estuarine wetland in Hong Kong. J Environ Sci (China), 19(6), 657-62.
Lin, Y.-W., Yang, C.-C., Tuan, N.N., Huang, S.-L. 2016. Diversity of octylphenol polyethoxylate-degrading bacteria: With a special reference to Brevibacterium sp. TX4. International Biodeterioration & Biodegradation, 115, 55-63.
Lin, Y.W., Guo, G.L., Hsieh, H.C., Huang, S.L. 2010. Growth of Pseudomonas sp. TX1 on a wide range of octylphenol polyethoxylate concentrations and the formation of dicarboxylated metabolites. Bioresour Technol, 101(8), 2853-9.
Liney, K.E., Hagger, J.A., Tyler, C.R., Depledge, M.H., Galloway, T.S., Jobling, S. 2006. Health effects in fish of long-term exposure to effluents from wastewater treatment works. Environ Health Perspect, 114 Suppl 1, 81-9.
Lipscomb, J.D. 1994. Biochemistry of the soluble methane monooxygenase. Annu Rev Microbiol, 48, 371-99.
Liu, J., Wang, R., Huang, B., Lin, C., Wang, Y., Pan, X. 2011. Distribution and bioaccumulation of steroidal and phenolic endocrine disrupting chemicals in wild fish species from Dianchi Lake, China. Environ Pollut, 159(10), 2815-22.
Liu, M., Hashi, Y., Pan, F., Yao, J., Song, G., Lin, J.M. 2006. Automated on-line liquid chromatography-photodiode array-mass spectrometry method with dilution line for the determination of bisphenol A and 4-octylphenol in serum. J Chromatogr A, 1133(1-2), 142-8.
Liu, Y., Wang, F., Xia, S., Zhao, J. 2008. Study of 4-t-octylphenol degradation and microbial community in granular sludge. J Environ Sci (China), 20(2), 167-71.
Liu, Z.H., Kanjo, Y., Mizutani, S. 2009. Removal mechanisms for endocrine disrupting compounds (EDCs) in wastewater treatment - physical means, biodegradation, and chemical advanced oxidation: a review. Sci Total Environ, 407(2), 731-48.
Locher, H.H., Poolman, B., Cook, A.M., Konings, W.N. 1993. Uptake of 4-toluene sulfonate by Comamonas testosteroni T-2. J Bacteriol, 175(4), 1075-80.
Lopez-Espinosa, M.J., Freire, C., Arrebola, J.P., Navea, N., Taoufiki, J., Fernandez, M.F., Ballesteros, O., Prada, R., Olea, N. 2009. Nonylphenol and octylphenol in adipose tissue of women in Southern Spain. Chemosphere, 76(6), 847-52.
Loyo-Rosales, J.E., Rosales-Rivera, G.C., Lynch, A.M., Rice, C.P., Torrents, A. 2004. Migration of nonylphenol from plastic containers to water and a milk surrogate. Journal of Agricultural and Food Chemistry, 52(7), 2016-20.
Lu, J., Jin, Q., He, Y., Wu, J., Zhao, J. 2008. Biodegradation of nonylphenol ethoxylates by Bacillus sp. LY capable of heterotrophic nitrification. FEMS Microbiol Lett, 280(1), 28-33.
Lu, Y.Y., Chen, M.L., Sung, F.C., Wang, P.S., Mao, I.F. 2007. Daily intake of 4-nonylphenol in Taiwanese. Environ Int, 33(7), 903-10.
Lu, Z., Gan, J. 2014. Analysis, toxicity, occurrence and biodegradation of nonylphenol isomers: a review. Environ Int, 73, 334-45.
Ma, M., Li, J., Wang, Z. 2005. Assessing the detoxication efficiencies of wastewater treatment processes using a battery of bioassays/biomarkers. Arch Environ Contam Toxicol, 49(4), 480-7.
Maguire, R.J. 1999. Review of the persistence of nonylphenol and nonylphenol ethoxylatesin aquatic environments. Water Quality Research Journal of Canada, 34(1), 37.
Maki, H., Masuda, N., Fujiwara, Y., Ike, M., Fujita, M. 1994. Degradation of alkylphenol ethoxylates by Pseudomonas sp. strain TR01. Appl Environ Microbiol, 60(7), 2265-71.
Matsui, T., Nomura, Y., Takano, M., Imai, S., Nakayama, H., Miyasaka, H., Okuhata, H., Tanaka, S., Matsuura, H., Harada, K., Bamba, T., Hirata, K., Kato, K. 2011. Molecular cloning and partial characterization of a peroxidase gene expressed in the roots of Portulaca oleracea cv., one potentially useful in the remediation of phenolic pollutants. Biosci Biotechnol Biochem, 75(5), 882-90.
McCormick, M.S., Lippard, S.J. 2011. Analysis of substrate access to active sites in bacterial multicomponent monooxygenase hydroxylases: X-ray crystal structure of xenon-pressurized phenol hydroxylase from Pseudomonas sp. OX1. Biochemistry, 50(51), 11058-69.
Meldahl, A.C., Nithipatikom, K., Lech, J.J. 1996. Metabolism of several C-14-nonylphenol isomers by rainbow trout (Oncorhynchus mykiss): In vivo and in vitro microsomal metabolites. Xenobiotica, 26(11), 1167-80.
Merimaa, M., Heinaru, E., Liivak, M., Vedler, E., Heinaru, A. 2006. Grouping of phenol hydroxylase and catechol 2,3-dioxygenase genes among phenol- and p-cresol-degrading Pseudomonas species and biotypes. Arch Microbiol, 186(4), 287-96.
Meunier, B., de Visser, S.P., Shaik, S. 2004. Mechanism of oxidation reactions catalyzed by cytochrome p450 enzymes. Chem Rev, 104(9), 3947-80.
Montgomery-Brown, J., Drewes, J.E., Fox, P., Reinhard, M. 2003. Behavior of alkylphenol polyethoxylate metabolites during soil aquifer treatment. Water Res, 37(15), 3672-81.
Montgomery-Brown, J., Reinhard, M. 2003. Occurrence and behavior of alkylphenol polyethoxylates in the environment. Environmental Engineering Science, 20(5), 471-86.
Muller, S., Schmid, P., Schlatter, C. 1998. Pharmacokinetic behavior of 4-nonylphenol in humans. Environ Toxicol Pharmacol, 5(4), 257-65.
Naylor, R. 1998. International trade and economic integration when labour markets are generally unionised. European Economic Review, 42(7), 1251-67.
Neilson, A.H., Allard, A.S., Hynning, P.A., Remberger, M., Landner, L. 1983. Bacterial methylation of chlorinated phenols and guaiacols: formation of veratroles from guaiacols and high-molecular-weight chlorinated lignin. Appl Environ Microbiol, 45(3), 774-83.
Nguyen, M.H., Sigoillot, J.C. 1997. Isolation from coastal sea water and characterization of bacterial strains involved in non-ionic surfactant degradation. Biodegradation, 7(5), 369-375.
Ni, Y., Li, C.X., Ma, H.M., Zhang, J., Xu, J.H. 2011. Biocatalytic properties of a recombinant aldo-keto reductase with broad substrate spectrum and excellent stereoselectivity. Appl Microbiol Biotechnol, 89(4), 1111-8.
Nielsen, D.R., McLellan, P.J., Daugulis, A.J. 2006. Direct estimation of the oxygen requirements of Achromobacter xylosoxidans for aerobic degradation of monoaromatic hydrocarbons (BTEX) in a bioscrubber. Biotechnol Lett, 28(16), 1293-8.
Nimrod, A.C., Benson, W.H. 1996. Environmental estrogenic effects of alkylphenol ethoxylates. Crit Rev Toxicol, 26(3), 335-64.
Nishio, E., Ichiki, Y., Tamura, H., Morita, S., Watanabe, K., Yoshikawa, H. 2002. Isolation of bacterial strains that produce the endocrine disruptor, octylphenol diethoxylates, in paddy fields. Bioscience Biotechnology and Biochemistry, 66(9), 1792-8.
Nishio, E., Yoshikawa, H., Wakayama, M., Tamura, H., Morita, S., Tomita, Y. 2005. Isolation and identification of Sphingomonas sp that yields tert-octylphenol monoethoxylate under aerobic conditions. Bioscience Biotechnology and Biochemistry, 69(7), 1226-31.
Nixdorff, K., Gmeiner, J., Martin, H.H. 1978. Interaction of lipopolysaccharide with detergents and its possible role in the detergent resistance of the outer membrane of Gram-negative bacteria. Biochim Biophys Acta, 510(1), 87-98.
Nomura, S., Daidoji, T., Inoue, H., Yokota, H. 2008. Differential metabolism of 4-n- and 4-tert-octylphenols in perfused rat liver. Life Sci, 83(5-6), 223-8.
Nordlund, I., Powlowski, J., Shingler, V. 1990. Complete nucleotide sequence and polypeptide analysis of multicomponent phenol hydroxylase from Pseudomonas sp. strain CF600. J Bacteriol, 172(12), 6826-33.
Obradors, N., Aguilar, J. 1991. Efficient biodegradation of high-molecular-weight polyethylene glycols by pure cultures of Pseudomonas stutzeri. Appl Environ Microbiol, 57(8), 2383-8.
Ohe, T., Mashino, T., Hirobe, M. 1997. Substituent elimination from p-substituted phenols by cytochrome P450. ipso-Substitution by the oxygen atom of the active species. Drug Metab Dispos, 25(1), 116-22.
Otaka, H., Yasuhara, A., Morita, M. 2003. Determination of bisphenol A and 4-nonylphenol in human milk using alkaline digestion and cleanup by solid-phase extraction. Anal Sci, 19(12), 1663-6.
Pachura-Bouchet, S., Blaise, C., Vasseur, P. 2006. Toxicity of nonylphenol on the cnidarian Hydra attenuata and environmental risk assessment. Environ Toxicol, 21(4), 388-94.
Pearson, J., Dahal, U.P., Rock, D., Peng, C.C., Schenk, J.O., Joswig-Jones, C., Jones, J.P. 2011. The kinetic mechanism for cytochrome P450 metabolism of type II binding compounds: evidence supporting direct reduction. Arch Biochem Biophys, 511(1-2), 69-79.
Pedersen, R.T., Hill, E.M. 2000. Identification of novel metabolites of the xenoestrogen 4-tert-octylphenol in primary rat hepatocytes. Chem Biol Interact, 128(3), 189-209.
Petrovic, M., Barcelo, D. 2001a. Analysis of ethoxylated nonionic surfactants and their metabolites by liquid chromatography/atmospheric pressure ionization mass spectrometry. J Mass Spectrom, 36(11), 1173-85.
Petrovic, M., Barcelo, D. 2001b. Determination of anionic and nonionic surfactants, their degradation products, and endocrine-disrupting compounds in sewage sludge by liquid chromatography/mass spectrometry. Analytical Chemistry, 72(19), 4560-7.
Pinero-Fernandez, S., Chimerel, C., Keyser, U.F., Summers, D.K. 2011. Indole transport across Escherichia coli membranes. J Bacteriol, 193(8), 1793-8.
Porter, A.W., Campbell, B.R., Kolvenbach, B.A., Corvini, P.F., Benndorf, D., Rivera-Cancel, G., Hay, A.G. 2012. Identification of the flavin monooxygenase responsible for ipso substitution of alkyl and alkoxyphenols in Sphingomonas sp. TTNP3 and Sphingobium xenophagum Bayram. Appl Microbiol Biotechnol, 94(1), 261-72.
Porter, A.W., Hay, A.G. 2007. Identification of opdA, a gene involved in biodegradation of the endocrine disrupter octylphenol. Appl Environ Microbiol, 73(22), 7373-9.
Powlowski, J., Sealy, J., Shingler, V., Cadieux, E. 1997. On the role of DmpK, an auxiliary protein associated with multicomponent phenol hydroxylase from Pseudomonas sp. strain CF600. J Biol Chem, 272(2), 945-51.
Powlowski, J., Shingler, V. 1994. Genetics and biochemistry of phenol degradation by Pseudomonas sp. CF600. Biodegradation, 5(3-4), 219-36.
Powlowski, J., Shingler, V. 1990. In vitro analysis of polypeptide requirements of multicomponent phenol hydroxylase from Pseudomonas sp. strain CF600. J Bacteriol, 172(12), 6834-40.
Probian, C., Wulfing, A., Harder, J. 2003. Anaerobic mineralization of quaternary carbon atoms: isolation of denitrifying bacteria on pivalic acid (2,2-dimethylpropionic acid). Appl Environ Microbiol, 69(3), 1866-70.
Reichlin, F., Kohler, H.P. 1994. Pseudomonas sp. strain HBP1 Prp degrades 2-isopropylphenol (ortho-cumenol) via meta cleavage. Appl Environ Microbiol, 60(12), 4587-91.
Rost, B. 1999. Twilight zone of protein sequence alignments. Protein Eng, 12(2), 85-94.
Routledge, E.J., Sumpter, J.P. 1996. Estrogenic activity of surfactants and some of their degradation products assessed using a recombinant yeast screen. Environmental Toxicology and Chemistry, 15(3), 241-8.
Sanchez, M.A., Gonzalez, B. 2007. Genetic characterization of 2,4,6-trichlorophenol degradation in Cupriavidus necator JMP134. Appl Environ Microbiol, 73(9), 2769-76.
Sakuyama, H., Endo, Y., Fujimoto, K., Hatana, Y. 2003. Oxidative degradation of alkylphenols by horseradish peroxidase. J Biosci Bioeng, 96(3), 227-31.
Sasaki, M., Maki, J., Oshiman, K., Matsumura, Y., Tsuchido, T. 2005. Biodegradation of bisphenol A by cells and cell lysate from Sphingomonas sp. strain AO1. Biodegradation, 16(5), 449-59.
Sasaki, M., Tsuchido, T., Matsumura, Y. 2008. Molecular cloning and characterization of cytochrome P450 and ferredoxin genes involved in bisphenol A degradation in Sphingomonas bisphenolicum strain AO1. J Appl Microbiol, 105(4), 1158-69.
Sato, H., Shibata, A., Wang, Y., Yoshikawa, H., Tamura, H. 2001. Characterization of biodegradation intermediates of non-ionic surfactants by matrix-assisted laser desorption/ionization-mass spectrometry 1. Bacterial biodegradation of octylphenol polyethoxylate under aerobic conditions. Polymer Degradation and Stability, 74(1), 69-75.
Sato, H., Shibata, A., Wang, Y., Yoshikawa, H., Tamura, H. 2003. Characterization of biodegradation intermediates of nonionic surfactants by MALDI-MS. 2. Oxidative biodegradation profiles of uniform octylphenol polyethoxylate in 18O-labeled water. Biomacromolecules, 4(1), 46-51.
Sazinsky, M.H., Dunten, P.W., McCormick, M.S., DiDonato, A., Lippard, S.J. 2006. X-ray structure of a hydroxylase-regulatory protein complex from a hydrocarbon-oxidizing multicomponent monooxygenase, Pseudomonas sp. OX1 phenol hydroxylase. Biochemistry, 45(51), 15392-404.
Schmidt, B., Patti, H., Niewersch, C., Schuphan, I. 2003. Biotransformation of [ring-U-14C]4-n-nonylphenol by Agrostemma githago cell culture in a two-liquid-phase system. Biotechnol Lett, 25(16), 1375-81.
Schwarzenbach, R.P., Escher, B.I., Fenner, K., Hofstetter, T.B., Johnson, C.A., von Gunten, U., Wehrli, B. 2006. The challenge of micropollutants in aquatic systems. Science, 313(5790), 1072-7.
Scott, M.J., Jones, M.N. 2000. The biodegradation of surfactants in the environment. Biochim Biophys Acta, 1508(1-2), 235-51.
Sharma, V.K., Anquandah, G.A., Yngard, R.A., Kim, H., Fekete, J., Bouzek, K., Ray, A.K., Golovko, D. 2009. Nonylphenol, octylphenol, and bisphenol-A in the aquatic environment: a review on occurrence, fate, and treatment. J Environ Sci Health A Tox Hazard Subst Environ Eng, 44(5), 423-42.
Sharpe, R.M., Fisher, J.S., Millar, M.M., Jobling, S., Sumpter, J.P. 1995. Gestational and lactational exposure of rats to xenoestrogens results in reduced testicular size and sperm production. Environ Health Perspect, 103(12), 1136-43.
Sharpe, R.M., Skakkebaek, N.E. 1993. Are oestrogens involved in falling sperm counts and disorders of the male reproductive tract? Lancet, 341(8857), 1392-5.
Shibata, A., Katayama, A. 2007. Anaerobic co-metabolic oxidation of 4-alkylphenols with medium-length or long alkyl chains by Thauera sp., strain R5. Appl Microbiol Biotechnol, 75(5), 1151-61.
Shingler, V., Franklin, F.C., Tsuda, M., Holroyd, D., Bagdasarian, M. 1989. Molecular analysis of a plasmid-encoded phenol hydroxylase from Pseudomonas CF600. J Gen Microbiol, 135(5), 1083-92.
Shingler, V., Moore, T. 1994. Sensing of aromatic compounds by the DmpR transcriptional activator of phenol-catabolizing Pseudomonas sp. strain CF600. J Bacteriol, 176(6), 1555-60.
Shingler, V., Powlowski, J., Marklund, U. 1992. Nucleotide sequence and functional analysis of the complete phenol/3,4-dimethylphenol catabolic pathway of Pseudomonas sp. strain CF600. J Bacteriol, 174(3), 711-24.
Smeds, A., Saukko, P. 2003. Brominated flame retardants and phenolic endocrine disrupters in Finnish human adipose tissue. Chemosphere, 53(9), 1123-30.
Soares, A., Guieysse, B., Delgado, O., Mattiasson, B. 2003. Aerobic biodegradation of nonylphenol by cold-adapted bacteria. Biotechnol Lett, 25(9), 731-8.
Soares, A., Guieysse, B., Jefferson, B., Cartmell, E., Lester, J.N. 2008. Nonylphenol in the environment: a critical review on occurrence, fate, toxicity and treatment in wastewaters. Environ Int, 34(7), 1033-49.
Soares, A., Jonasson, K., Terrazas, E., Guieysse, B., Mattiasson, B. 2005. The ability of white-rot fungi to degrade the endocrine-disrupting compound nonylphenol. Appl Microbiol Biotechnol, 66(6), 719-25.
Soto, A.M., Justicia, H., Wray, J.W., Sonnenschein, C. 1991. p-Nonyl-phenol: an estrogenic xenobiotic released from "modified" polystyrene. Environ Health Perspect, 92, 167-73.
Soucek, P., Filipcova, B., Gut, I. 1994. Cytochrome P450 destruction and radical scavenging by benzene and its metabolites. Evidence for the key role of quinones. Biochem Pharmacol, 47(12), 2233-42.
Staples, C.A., Williams, J.B., Blessing, R.L., Varineau, P.T. 1999. Measuring the biodegradability of nonylphenol ether carboxylates, octylphenol ether carboxylates, and nonylphenol. Chemosphere, 38(9), 2029-39.
Strubel, V., Engesser, K.H., Fischer, P., Knackmuss, H.J. 1991. 3-(2-hydroxyphenyl)catechol as substrate for proximal meta ring cleavage in dibenzofuran degradation by Brevibacterium sp. strain DPO 1361. J Bacteriol, 173(6), 1932-7.
Tabira, Y., Nakai, M., Asai, D., Yakabe, Y., Tahara, Y., Shinmyozu, T., Noguchi, M., Takatsuki, M., Shimohigashi, Y. 1999. Structural requirements of para-alkylphenols to bind to estrogen receptor. Eur J Biochem, 262(1), 240-5.
Takeo, M., Maeda, Y., Maeda, J., Nishiyama, N., Kitamura, C., Kato, D., Negoro, S. 2012. Two identical nonylphenol monooxygenase genes linked to IS6100 and some putative insertion sequence elements in Sphingomonas sp. NP5. Microbiology, 158(Pt 7), 1796-807.
Takeo, M., Nishimura, M., Takahashi, H., Kitamura, C., Kato, D., Negoro, S. 2007. Purification and characterization of alkylcatechol 2,3-dioxygenase from butylphenol degradation pathway of Pseudomonas putida MT4. J Biosci Bioeng, 104(4), 309-14.
Takeo, M., Prabu, S.K., Kitamura, C., Hirai, M., Takahashi, H., Kato, D., Negoro, S. 2006. Characterization of alkylphenol degradation gene cluster in Pseudomonas putida MT4 and evidence of oxidation of alkylphenols and alkylcatechols with medium-length alkyl chain. J Biosci Bioeng, 102(4), 352-61.
Takeuchi, M., Kawai, F., Shimada, Y., Yokota, A. 1993. Taxonomic Study of Polyethylene Glycol-Utilizing Bacteria: Emended Description of the Genus Sphingomonas and New Descriptions of Sphingomonas macrogoltabidus sp. nov., Sphingomonas sanguis sp. nov. and Sphingomonas terrae sp. nov. Systematic and Applied Microbiology, 16(2), 227-38.
Tamagawa, Y., Hirai, H., Kawai, S., Nishida, T. 2007. Removal of estrogenic activity of 4-tert-octylphenol by ligninolytic enzymes from white rot fungi. Environ Toxicol, 22(3), 281-6.
Tan, B.L.L., Mohd, M.A. 2003. Analysis of selected pesticides and alkylphenols in human cord blood by gas chromatograph-mass spectrometer. Talanta, 61(3), 385-91.
Tanenbaum, D.M., Wang, Y., Williams, S.P., Sigler, P.B. 1998. Crystallographic comparison of the estrogen and progesterone receptor′s ligand binding domains. Proc Natl Acad Sci U S A, 95(11), 5998-6003.
Tanghe, T., Dhooge, W., Verstraete, W. 2000. Formation of the metabolic intermediate 2,4,4-trimethyl-2-pentanol during incubation of a Sphingomonas sp. strain with the xeno-estrogenic octylphenol. Biodegradation, 11(1), 11-9.
Tanghe, T., Dhooge, W., Verstraete, W. 1999. Isolation of a bacterial strain able to degrade branched nonylphenol. Appl Environ Microbiol, 65(2), 746-51.
Thayer, J.R., Wheelis, M.L. 1982. Active transport of benzoate in Pseudomonas putida. J Gen Microbiol, 128(8), 1749-53.
Thibaut, R., Debrauwer, L., Rao, D., Cravedi, J.P. 1998. Characterization of biliary metabolites of 4-n-nonylphenol in rainbow trout (Oncorhynchus mykiss). Xenobiotica, 28(8), 745-57.
Thibaut, R., Debrauwer, L., Rao, D., Cravedi, J.P. 1999. Urinary metabolites of 4-n-nonylphenol in rainbow trout (Oncorhynchus mykiss). Science of the Total Environment, 233(1-3), 193-200.
Thiele, B., Gunther, K., Schwuger, M.J. 1997. Alkylphenol Ethoxylates: Trace Analysis and Environmental Behavior. Chem Rev, 97(8), 3247-72.
Toppari, J., Larsen, J.C., Christiansen, P., Giwercman, A., Grandjean, P., Guillette, L.J., Jr., Jegou, B., Jensen, T.K., Jouannet, P., Keiding, N., Leffers, H., McLachlan, J.A., Meyer, O., Muller, J., Rajpert-De Meyts, E., Scheike, T., Sharpe, R., Sumpter, J., Skakkebaek, N.E. 1996. Male reproductive health and environmental xenoestrogens. Environ Health Perspect, 104 Suppl 4, 741-803.
Toyama, T., Kainuma, Y., Kikuchi, S., Mori, K. 2012. Biodegradation of bisphenol A and 4-alkylphenols by Novosphingobium sp. strain TYA-1 and its potential for treatment of polluted water. Water Sci Technol, 66(10), 2202-8.
Toyama, T., Momotani, N., Ogata, Y., Miyamori, Y., Inoue, D., Sei, K., Mori, K., Kikuchi, S., Ike, M. 2010. Isolation and characterization of 4-tert-butylphenol-utilizing Sphingobium fuliginis strains from Phragmites australis rhizosphere sediment. Appl Environ Microbiol, 76(20), 6733-40.
Toyama, T., Murashita, M., Kobayashi, K., Kikuchi, S., Sei, K., Tanaka, Y., Ike, M., Mori, K. 2011. Acceleration of nonylphenol and 4-tert-octylphenol degradation in sediment by Phragmites australis and associated rhizosphere bacteria. Environ Sci Technol, 45(15), 6524-30.
Toyo′oka, T., Oshige, Y. 2000. Determination of alkylphenols in mineral water contained in PET bottles by liquid chromatography with coulometric detection. Analytical Sciences, 16(10), 1071-6.
Tsutsumi, Y., Haneda, T., Nishida, T. 2001. Removal of estrogenic activities of bisphenol A and nonylphenol by oxidative enzymes from lignin-degrading basidiomycetes. Chemosphere, 42(3), 271-6.
Tuan, N.N., Hsieh, H.C., Lin, Y.W., Huang, S.L. 2011. Analysis of bacterial degradation pathways for long-chain alkylphenols involving phenol hydroxylase, alkylphenol monooxygenase and catechol dioxygenase genes. Bioresour Technol, 102(5), 4232-40.
Tuan, N.N., Lin, Y.W., Huang, S.L. 2013. Catabolism of 4-alkylphenols by Acinetobacter sp. OP5: genetic organization of the oph gene cluster and characterization of alkylcatechol 2, 3-dioxygenase. Bioresour Technol, 131, 420-8.
Turkovskava, O., L. Panchenko, A. Muratova, E. Dubrovskaya, and G. Shub. . 1996. Biodegradation of surfactant and mineral oils. International Biodeterioration and Biodegradation, 37, 250-5.
Urlacher, V.B., Girhard, M. 2012. Cytochrome P450 monooxygenases: an update on perspectives for synthetic application. Trends Biotechnol, 30(1), 26-36.
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(Pt 6), 2045-8.
Vaara, M. 1992. Agents that increase the permeability of the outer membrane. Microbiol Rev, 56(3), 395-411.
Vaillancourt, F.H., Bolin, J.T., Eltis, L.D. 2006. The ins and outs of ring-cleaving dioxygenases. Crit Rev Biochem Mol Biol, 41(4), 241-67.
Vallejo, A., Usobiaga, A., Ortiz-Zarragoitia, M., Cajaraville, M.P., Fernandez, L.A., Zuloaga, O. 2010. Focused ultrasound-assisted acceleration of enzymatic hydrolysis of alkylphenols and 17 beta-oestradiol glucuronide in fish bile. Anal Bioanal Chem, 398(5), 2307-14.
Vallini, G., Frassinetti, S., D′Andrea, F., Catelani, G., Agnolucci, M. 2001. Biodegradation of 4-(1-nonyl)phenol by axenic cultures of the yeast Candida aquaetextoris: identification of microbial breakdown products and proposal of a possible metabolic pathway. International Biodeterioration & Biodegradation, 47(3), 133-40.
Vazquez, G.R., Meijide, F.J., Da Cuna, R.H., Lo Nostro, F.L., Piazza, Y.G., Babay, P.A., Trudeau, V.L., Maggese, M.C., Guerrero, G.A. 2009. Exposure to waterborne 4-tert-octylphenol induces vitellogenin synthesis and disrupts testis morphology in the South American freshwater fish Cichlasoma dimerus (Teleostei, Perciformes). Comparative Biochemistry and Physiology C-Toxicology & Pharmacology, 150(2), 298-306.
Viggiani, A., Olivieri, G., Siani, L., Di Donato, A., Marzocchella, A., Salatino, P., Barbieri, P., Galli, E. 2006. An airlift biofilm reactor for the biodegradation of phenol by Pseudomonas stutzeri OX1. J Biotechnol, 123(4), 464-77.
Voutsa, D., Hartmann, P., Schaffner, C., Giger, W. 2006. Benzotriazoles, alkylphenols and bisphenol A in municipal wastewaters and in the Glatt River, Switzerland. Environ Sci Pollut Res Int, 13(5), 333-41.
Wackett, L.P., Hershberger, C.D. 2001. Biocatalysis and Biodegradation: Microbial Transformation of Organic Compounds. ASM Press, Washington, DC, USA.
Wan, N.S., Gu, J.D., Huang, J.H., Gao, C.D. 2007. Isolation of Achromobacter xylosoxidans NS12 and degradation of nitrophenols. Huan Jing Ke Xue, 28(2), 422-6.
Wang, J.Q., Majima, N., Hirai, H., Kawagishi, H. 2012. Effective removal of endocrine-disrupting compounds by lignin peroxidase from the white-rot fungus Phanerochaete sordida YK-624. Current Microbiology, 64(3), 300-3.
Waring, R.H., Harris, R.M. 2005. Endocrine disrupters: a human risk? Mol Cell Endocrinol, 244(1-2), 2-9.
Weber, S., Leuschner, P., Kampfer, P., Dott, W., Hollender, J. 2005. Degradation of estradiol and ethinyl estradiol by activated sludge and by a defined mixed culture. Appl Microbiol Biotechnol, 67(1), 106-12.
Werck-Reichhart, D., Feyereisen, R. 2000. Cytochromes P450: a success story. Genome Biol, 1(6), REVIEWS3003.
White, E., Malone, K., Weiss, N., Daling, J. 1994a. Breast cancer among young U.S. women in relation to oral contraceptive use. JNCI J Natl Cancer Inst, 1994, 505-14.
White, G.F. 1993. Bacterial biodegradation of ethoxylated surfactants. Pesticide Science, 37(2), 159-66.
White, G.F., Russell, N.J., Tidswell, E.C. 1996. Bacterial scission of ether bonds. Microbiol Rev, 60(1), 216-32.
White, R., Jobling, S., Hoare, S.A., Sumpter, J.P., Parker, M.G. 1994b. Environmentally persistent alkylphenolic compounds are estrogenic. Endocrinology, 135(1), 175-82.
Whited, G.M., Gibson, D.T. 1991. Separation and partial characterization of the enzymes of the toluene-4-monooxygenase catabolic pathway in Pseudomonas mendocina KR1. J Bacteriol, 173(9), 3017-20.
Williams, P.A., Cosme, J., Ward, A., Angove, H.C., Matak Vinkovic, D., Jhoti, H. 2003. Crystal structure of human cytochrome P450 2C9 with bound warfarin. Nature, 424(6947), 464-8.
Yalkowsky, S.H., Dannenfelser, R.M. 1992. Aquasol database of aqueous solubility. College of Pharmacy, University of Arizona, Tucson, AZ.
Yamada, K., Inoue, T., Akiba, Y., Kashiwada, A., Matsuda, K., Hirata, M. 2006. Removal of p-alkylphenols from aqueous solutions by combined use of mushroom tyrosinase and chitosan beads. Bioscience Biotechnology and Biochemistry, 70(10), 2467-75.
Yamanaka, H., Kawai, F. 1989. Purification and characterization of constitutive polyethylene glycol (PEG) dehydrogenase of a PEG 4000-utilizing Flavobacterium sp. no. 203. Journal of Fermentation and Bioengineering, 67(5), 324-30.
Yang, D.K., Ding, W.H. 2005. Determination of alkylphenolic residues in fresh fruits and vegetables by extractive steam distillation and gas chromatography-mass spectrometry. Journal of Chromatography A, 1088(1-2), 200-4.
Yao, J., Zhang, G., Wu, Q., Chen, G.-Q., Zhang, R. 1999. Production of polyhydroxyalkanoates by Pseudomonas nitroreducens. Antonie van Leeuwenhoek, 75(4), 345-9.
Ye, X., Kuklenyik, Z., Needham, L.L., Calafat, A.M. 2006. Measuring environmental phenols and chlorinated organic chemicals in breast milk using automated on-line column-switching-high performance liquid chromatography-isotope dilution tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci, 831(1-2), 110-5.
Ying, G.G., Williams, B., Kookana, R. 2002. Environmental fate of alkylphenols and alkylphenol ethoxylates--a review. Environ Int, 28(3), 215-26.
Yuan, S.Y., Yu, C.H., Chang, B.V. 2004. Biodegradation of nonylphenol in river sediment. Environ Pollut, 127(3), 425-30.
Zhang, C., Zeng, G., Yuan, L., Yu, J., Li, J., Huang, G., Xi, B., Liu, H. 2007. Aerobic degradation of bisphenol A by Achromobacter xylosoxidans strain B-16 isolated from compost leachate of municipal solid waste. Chemosphere, 68(1), 181-90.
Zhao, J., Zhang, G., Qin, Y., Zhao, Y. 2006. Aerobic biodegradation of alkylphenol ethoxylates. Bioresour Technol, 97(18), 2478-80.
Zhu, B.T., Conney, A.H. 1998. Functional role of estrogen metabolism in target cells: review and perspectives. Carcinogenesis, 19(1), 1-27.


指導教授 黃雪莉、羅南德(Shir-Ly Huang Roland Kirschner) 審核日期 2017-2-3
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