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The metabolic pathway of metamifop degradation by consortium ME-1 and its bacterial community structure

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Abstract

Metamifop is universally used in agriculture as a post-emergence aryloxyphenoxy propionate herbicide (AOPP), however its microbial degradation mechanism remains unclear. Consortium ME-1 isolated from AOPP-contaminated soil can degrade metamifop completely after 6 days and utilize it as the carbon source for bacterial growth. Meanwhile, consortium ME-1 possessed the ability to degrade metamifop stably under a wide range of pH (6.0–10.0) or temperature (20–42 °C). HPLC–MS analysis shows that N-(2-fluorophenyl)-2-(4-hydroxyphenoxy)-N-methyl propionamide, 2-(4-hydroxyphenoxy)-propionic acid, 6-chloro-2-benzoxazolinone and N-methyl-2-fluoroaniline, were detected and identified as four intermediate metabolites. Based on the metabolites identified, a putative metabolic pathway of metamifop was proposed for the first time. In addition, the consortium ME-1 was also able to transform or degrade other AOPP such as fenoxaprop-p-ethyl, clodinafop-propargyl, quizalofop-p-ethyl and cyhalofop-butyl. Moreover, the community structure of ME-1 with lower microbial diversity compared with the initial soil sample was investigated by high throughput sequencing. β-Proteobacteria and Sphingobacteria were the largest class with sequence percentages of 46.6% and 27.55% at the class level. In addition, 50 genera were classified in consortium ME-1, of which Methylobacillus, Sphingobacterium, Bordetella and Flavobacterium were the dominant genera with sequence percentages of 25.79, 25.61, 14.68 and 9.55%, respectively.

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References

  • Abraham J, Silambarasan S (2013) Biodegradation of chlorpyrifos and its hydrolyzing metabolite 3,5,6-trichloro-2-pyridinol by Sphingobacterium sp. JAS3. Process Biochem 48:1559–1564

    Article  CAS  Google Scholar 

  • Amareshwari P, Bhatia M, Venkatesh K, Rani AR, Ravi GV, Bhakt P, Nair AS (2015) Isolation and characterization of a novel chlorpyrifos degrading flavobacterium species EMBS0145 by 16S rRNA gene sequencing. Interdiscip Sci 7:1–6

    Article  CAS  PubMed  Google Scholar 

  • Bolger AM, Lohse M, Usadel B (2014) Trimmomatic: a flexible trimmer for illumina sequence data. Bioinformatics. doi:10.1093/bioinformatics/btu170

    PubMed  PubMed Central  Google Scholar 

  • Burrows HD, Santaballa JA, Steenken S (2002) Reaction pathways and mechanisms of photodegradation of pesticides. J Photoch Photobio B 67:71–108

    Article  CAS  Google Scholar 

  • Cai S, Cai TM, Liu S, Yang Q, He J, Chen LW, Hu J (2014) Biodegradation of N-methylpyrrolidone by Paracoccus sp. NMD-4 and its degradation pathway. Int Biodeter Biodeg 93:70–77

    Article  CAS  Google Scholar 

  • Cai Z, Zhang W, Li S, Ma J, Wang J, Zhao X (2015) Microbial degradation mechanism and pathway of the novel insecticide paichongding by a newly isolated Sphingobacterium sp. P1-3 from soil. J Agr Food Chem 63:3823–3829

    Article  CAS  Google Scholar 

  • Caracciolo AB, Topp E, Grenni P (2015) Pharmaceuticals in the environment: biodegradation and effects on natural microbial communities: a review. J Pharmaceut Biomed 106:25–36

    Article  Google Scholar 

  • Dong WL, Jiang S, Shi KW, Wang F, Li SH, Zhou J, Huang F, Wang YC, Zheng YX, Hou Y, Huang Y, Cui ZL (2015a) Biodegradation of fenoxaprop-p-ethyl (FE) by Acinetobacter sp. strain DL-2 and cloning of FE hydrolase gene afeH. Bioresour Technol 186:114–121

    Article  CAS  PubMed  Google Scholar 

  • Dong WL, Hou Y, Xi XD, Wang F, Li ZK, Ye XF, Huang Y, Cui ZL (2015b) Biodegradation of fenoxaprop-ethyl by an enriched consortium and its proposed metabolic pathway. Int Biodeter Biodeg 97:159–167

    Article  CAS  Google Scholar 

  • Dong WL, Chen QZ, Hou Y, Li SH, Zhuang K, Huang F, Zhou J, Li ZK, Wang J, Fu L, Zhang ZG, Wang F, Cui ZL (2015c) Metabolic pathway involved in 2-methyl-6- ethylaniline degradation by Sphingobium sp. strain MEA3-1 and cloning of the novel flavin-dependent monooxygenase system meaBA. Appl Environ Microb 8:8254–8264

    Article  Google Scholar 

  • Dong WL, Wang F, Huang F, Wang YC, Zhou J, Ye XF, Li ZK, Hou Y, Huang Y, Ma JF, Jiang M, Cui ZL (2016) Metabolic pathway involved in 6-chloro-2-benzoxazolinone degradation by Pigmentiphaga sp. strain DL-8 and identification of the novel metal-dependent hydrolase CbaA. Appl Environ Microb 82:4169–4179. doi:10.1128/AEM.00532-16

    Article  CAS  Google Scholar 

  • Edgar RC (2013) UPARSE: highly accurate OTU sequences from microbial amplicon reads. Nat Methods 10:996–998

    Article  CAS  PubMed  Google Scholar 

  • Edgar RC, Haas BJ, Clemente JC, Quince C, Knight R (2011) UCHIME improves sensitivity and speed of chimera detection. Bioinformatics 27:2194–2200

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Flint HJ, Scott KP, Duncan SH, Louis P, Forano E (2012) Microbial degradation of complex carbohydrates in the gut. Gut Microbes 3:289–306

    Article  PubMed  PubMed Central  Google Scholar 

  • Gennari M, Vincenti M, Nègre M, Ambrosoli R (1995) Microbial metabolism of fenoxaprop-ethyl. Pestic Sci 44:299–303

    CAS  Google Scholar 

  • Glenn AE, Bacon CW (2009) FDB2 encodes a member of the arylamine N-acetyltransferase family and is necessary for biotransformation of benzoxazolinones by Fusarium verticillioides. J Appl Microbial 107:657–671

    Article  CAS  Google Scholar 

  • Hao DC, Song SM, Mu J, Hu WL, Xiao PG (2016) Unearthing microbial diversity of Taxus rhizosphere via MiSeq high-throughput amplicon sequencing and isolate characterization. Sci Rep. doi:10.1038/srep22006

    Google Scholar 

  • Hou Y, Tao J, Shen WJ, Liu J, Li JQ, Li YF, Cao H, Cui ZL (2011) Isolation of the fenoxaprop-ethyl (FE)-degrading bacterium Rhodococcus sp. T1, and cloning of FE hydrolase gene feh. FEMS Microbial Lett 323:196–203

    Article  CAS  Google Scholar 

  • Hou Y, Li SH, Dong WL, Yuan Y, Wang YC, Shen WJ, Cui ZL (2015) Community structure of a propanil-degrading consortium and the metabolic pathway of Microbacterium sp. strain T4-7. Int Biodeter Biodeg 105:80–89

    Article  CAS  Google Scholar 

  • Hu LB, Yang JD, Zhou W, Yin YF, Chen J, Shi ZQ (2009) Isolation of a Methylobacillus sp. that degrades microcystin toxins associated with cyanobacteria. New Biotechnol 26:205–211

    Article  CAS  Google Scholar 

  • Janaki P, Chinnusamy C (2012) Determination of metamifop residues in soil under direct-seeded rice. Toxico Enviro Chem 94:1043–1052

    Article  CAS  Google Scholar 

  • Kim TJ, Chang HS, Kim JS, Hwang IT, Hong KS, Kim DW, Chung BJ (2003) Metamifop: mechanism of herbicidal activity and selectivity in rice and barnyardgrass. In The BCPC International Congress: Crop Science and Technology, Volumes 1 and 2. In: Proceedings of an International Congress held at the SECC, Glasgow, Scotland, UK

  • Li JQ, Liu J, Shen WJ, Zhao XL, Hou Y, Cao H, Cui ZL (2010) Isolation and characterization of 3,5,6-trichloro-2-pyridinol-degrading Ralstonia sp. strain T6. Bioresour Technol 101:7479–7483

    Article  CAS  PubMed  Google Scholar 

  • Lin J, Chen J, Wang Y, Cai X, Wei X, Qiao X (2008) More toxic and photoresistant products from photodegradation of fenoxaprop-p-ethyl. J Agr Food Chem 56:8226–8230

    Article  CAS  Google Scholar 

  • Magoč T, Salzberg SL (2011) FLASH: fast length adjustment of short reads to improve genome assemblies. Bioinformatics 27:2957–2963

    Article  PubMed  PubMed Central  Google Scholar 

  • Mohd-Kamil NAF, Hussain NH, Mizad MB, Abdul-Talib S (2014) Enhancing performance of Sphingobacterium spiritivorum in bioremediation phenanthrene contaminated sand. Remediat J 24:119–128

    Article  Google Scholar 

  • Moon JK, Keum YS, Hwang EC, Park BS, Chang HR, Li QX, Kim JH (2007) Hapten syntheses and antibody generation for a new herbicide, metamifop. J Agr Food Chem 55:5416–5422

    Article  CAS  Google Scholar 

  • Moon JK, Kim JH, Shibamoto T (2010) Photodegradation pathways and mechanisms of the herbicide metamifop in a water/acetonitrile solution. J Agr Food Chem 58:12357–12365

    Article  CAS  Google Scholar 

  • Nam IH, Kim Y, Cho D, Kim JG, Song H, Chon CM (2015) Effects of heavy metals on biodegradation of fluorene by a Sphingobacterium sp. strain (KM-02) isolated from polycyclic aromatic hydrocarbon-contaminated mine soil. Environ Eng Sci 32:891–898

    Article  CAS  Google Scholar 

  • Nie ZJ, Hang BJ, Cai S, Xie XT, He J, Li SP (2011) Degradation of cyhalofop-butyl (CyB) by Pseudomonas azotoformans strain QDZ-1 and cloning of a novel gene encoding CyB-hydrolyzing esterase. J Agr Food Chem 59:6040–6046

    Article  CAS  Google Scholar 

  • Oike H, Aoki-Yoshida A, Kimoto-Nira H, Yamagishi N, Tomita S, Sekiyama Y, Kobori M (2016) Dietary intake of heat-killed Lactococcus lactis H61 delays age-related hearing loss in C57BL/6 J mice. Sci Rep. doi:10.1038/srep23556

    Google Scholar 

  • Pandey P, Pathak H, Dave S (2016) Microbial ecology of hydrocarbon degradation in the soil: a review. Res J Environ Toxicol 10:1

    Article  Google Scholar 

  • Patel V, Jain S, Madamwar D (2012) Naphthalene degradation by bacterial consortium (DV-AL) developed from Alang-Sosiya ship breaking yard, Gujarat, India. Bioresour Technol 107:122–130

    Article  CAS  PubMed  Google Scholar 

  • Roy S, Singh SB (2005) Phototransformation of clodinafop-propargyl. J Environ Sci Heal B 40:525–534

    Article  Google Scholar 

  • Schloss PD, Westcott SL (2011) Assessing and improving methods used in operational taxonomic unit-based approaches for 16S rRNA gene sequence analysis. Appl Environ Microb 77:3219–3226

    Article  CAS  Google Scholar 

  • Tamura K, Dudley J, Nei M, Kumar S (2007) MEGA4: molecular evolutionary genetics analysis (MEGA) software version 4.0. Mol Boil Evol 24:1596–1599

    Article  CAS  Google Scholar 

  • Wang F, Grundmann S, Schmid M, Dörfler U, Roherer S, Munch JC, Schroll R (2007) Isolation and characterization of 1,2,4-trichlorobenzene mineralizing Bordetella sp. and its bioremediation potential in soil. Chemosphere 67:896–902

    Article  CAS  PubMed  Google Scholar 

  • Wang X, Hou ZG, Guo G, Zhao XF, Wang XH, Li ZB (2014) Photolysis kinetics and mechanism of metamifop. Chinese Agr Sci Bull 1:059

    Google Scholar 

  • Whitacre DM, Ware GW (2004) The pesticide book. Meister Media Worldwide, Willoughby

    Google Scholar 

  • Xiong J, Liu Y, Lin X, Zhang H, Zeng J, Hou J, Chu H (2012) Geographic distance and pH drive bacterial distribution in alkaline lake sediments across Tibetan Plateau. Environ Microbial 14:2457–2466

    Article  CAS  Google Scholar 

  • Xu J, Yao G, Liu D, Liu M, Wang P, Zhou Z (2016) Environmental fate of chiral herbicide fenoxaprop-ethyl in water-sediment microcosms. Sci Rep. doi:10.1038/srep26797

    Google Scholar 

  • Zhang YH, Xu D, Liu JQ, Zhao XH (2014) Enhanced degradation of five organophosphorus pesticides in skimmed milk by lactic acid bacteria and its potential relationship with phosphatase production. Food Chem 164:173–178

    Article  CAS  PubMed  Google Scholar 

  • Zhu Y, Lin X, Zhao F, Shi X, Li H, Li Y, Zhou G (2015) Erratum: meat, dairy and plant proteins alter bacterial composition of rat gut bacteria. Sci Rep 5:16546

    Article  CAS  PubMed  PubMed Central  Google Scholar 

Download references

Acknowledgements

This work was supported by the National Natural Science Foundation of China (Nos. 21390200 and 31560031), the Jiangsu Province Natural Science Foundation for Youths (No. BK20140940), China Postdoctoral Science Foundation (No. 2016M601787), and the Postdoctoral Foundation of Jiangsu Province (No. 1601043B), A Project Funded by the Priority Academic Program Development of Jiangsu Higher Education Institutions, A Project Supported by Program for New Century Excellent Talents in University, Program for Changjiang Scholars and Innovative Research Team in University (No. 06-A-047).

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Authors and Affiliations

  1. State Key Laboratory of Materials-Oriented Chemical Engineering, College of Biotechnology and Pharmaceutical Engineering, Nanjing Tech University, Nanjing, 211816, People’s Republic of China

    Weiliang Dong, Kuan Liu, Fengxue Xin, Min Zhang, Hao Wu, Jiangfeng Ma & Min Jiang

  2. Jiangsu National Synergetic Innovation Center for Advanced Materials (SICAM), Nanjing Tech University, Nanjing, 211816, People’s Republic of China

    Weiliang Dong, Fengxue Xin, Wenming Zhang, Min Zhang, Hao Wu, Jiangfeng Ma & Min Jiang

  3. College of Bioscience and Bioengineering, Jiangxi Agricultural University, Nanchang, 330045, People’s Republic of China

    Fei Wang

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  1. Weiliang Dong
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  9. Min Jiang
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Correspondence to Jiangfeng Ma or Min Jiang.

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Dong, W., Liu, K., Wang, F. et al. The metabolic pathway of metamifop degradation by consortium ME-1 and its bacterial community structure. Biodegradation 28, 181–194 (2017). https://doi.org/10.1007/s10532-017-9787-8

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