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

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林怡雯(Yi-Wen Lin) 查詢紙本館藏

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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.

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指導教授

黃雪莉、羅南德(Shir-Ly Huang Roland Kirschner)

審核日期

2017-2-3

推文