Advertisement

Applied Microbiology and Biotechnology

, Volume 99, Issue 19, pp 8187–8198 | Cite as

Characterization of a novel β-cypermethrin-degrading Aspergillus niger YAT strain and the biochemical degradation pathway of β-cypermethrin

  • Weiqin Deng
  • Derong Lin
  • Kai Yao
  • Huaiyu Yuan
  • Zhilong Wang
  • Jianlong Li
  • Likou Zou
  • Xinfeng Han
  • Kang Zhou
  • Li He
  • Xinjie Hu
  • Shuliang Liu
Environmental biotechnology

Abstract

Aspergillus niger YAT strain was obtained from Chinese brick tea (Collection number: CGMCC 10,568) and identified on the basis of morphological characteristics and internal transcribed spacer (ITS) sequence. The strain could degrade 54.83 % of β-cypermethrin (β-CY; 50 mg L−1) in 7 days and 100 % of 3-phenoxybenzoic acid (3-PBA; 100 mg L−1) in 22 h. The half-lives of β-CY and 3-PBA range from 3.573 to 11.748 days and from 5.635 to 12.160 h, respectively. The degradation of β-CY and 3-PBA was further described using first-order kinetic models. The pathway and mechanism of β-CY degraded by YAT were investigated by analyzing the degraded metabolites through high-performance liquid chromatography (HPLC) and liquid chromatography-mass spectrometry (LC-MS). Relevant enzymatic activities and substrate utilization were also investigated. β-CY degradation products were analyzed. Results indicated that YAT strain transformed β-CY into 3-PBA. 3-PBA was then gradually transformed into permethric acid, protocatechuic acid, 3-hydroxy-5-phenoxy benzoic acid, gallic acid, and phenol gradually. The YAT strain can also effectively degrade these metabolites. The results indicated that YAT strain has potential applications in bioremediation of pyrethroid insecticide (PI)-contaminated environments and fermented food.

Keywords

β-cypermethrin 3-phenoxybenzoic acid Biodegradation Degradation pathway Aspergillus niger YAT strain 

Notes

Acknowledgments

The authors extend their gratitude to the National Natural Science Foundation of China (31371775) for the financial support to this research.

Conflict of interest

We declare that no conflict of interest exists in the submission of this manuscript.

Ethical statement

All authors agreed to publish this manuscript. I would like to declare on behalf of my co-authors that this original work has not been previously published and is not under consideration for publication elsewhere, in whole or in part.

Supplementary material

253_2015_6690_MOESM1_ESM.pdf (273 kb)
ESM 1 (PDF 273 kb)

References

  1. Ansari RA, Rahman S, Kaur M, Anjum S, Raisuddin S (2011) In vivo cytogenetic and oxidative stress-inducing effects of cypermethrin in freshwater fish, Channa punctata Bloch. Ecotoxicol Environ Saf 74:150–156CrossRefPubMedGoogle Scholar
  2. Chen S, Hu Q, Hu M, Luo J, Weng Q, Lai K (2011a) Isolation and characterization of a fungus able to degrade pyrethroids and 3-phenoxybenzaldehyde. Bioresour Technol 102:8110–8116CrossRefPubMedGoogle Scholar
  3. Chen S, Hu M, Liu J, Zhong G, Yang L, Rizwan-ul-Haq M, Han H (2011b) Biodegradation of beta-cypermethrin and 3-phenoxybenzoic acid by a novel Ochrobactrum lupini DG-S-01. J Hazard Mater 187:433–440CrossRefPubMedGoogle Scholar
  4. Chen S, Yang L, Hu M, Liu J (2011c) Biodegradation of fenvalerate and 3-phenoxybenzoic acid by a novel Stenotrophomonas sp strain ZS-S-01 and its use in bioremediation of contaminated soils. Appl Microbiol Biotechnol 90:755–767CrossRefPubMedGoogle Scholar
  5. Chen S, Geng P, Xiao Y, Hu M (2012a) Bioremediation of β-cypermethrin and 3-phenoxybenzaldehyde contaminated soils using Streptomyces aureus HP-S-01. Appl Microbiol Biotechnol 94:505–515CrossRefPubMedGoogle Scholar
  6. Chen S, Liu C, Peng C, Liu H, Hu M, Zhong G (2012b) Biodegradation of chlorpyrifos and its hydrolysis product 3, 5, 6-trichloro-2-pyridinol by a new fungal strain Cladosporium cladosporioides Hu-01. PLoS One 7:1–12Google Scholar
  7. Chen S, Hu W, Xiao Y, Deng Y, Jia J, Hu M (2012c) Degradation of 3-phenoxybenzoic acid by a Bacillus sp. PLoS One 7:1–12Google Scholar
  8. Cuthbertson AGS, Murchie AK (2010) Ecological benefits of Anystis baccarum in an orchard ecosystem and the need for its conservation. Int J Environ Sci Technol 7:807–813CrossRefGoogle Scholar
  9. Cuthbertson AGS, Blackburn LF, Northing P, Luo W, Cannon RJC, Walters KFA (2010) Chemical compatibility testing of the entomopathogenic fungus Lecanicillium muscarium to control Bemisia tabaci in glasshouse environment. Int J Environ Sci Technol 7:405–409CrossRefGoogle Scholar
  10. Dewailly E, Forde M, Robertson L, Kaddar N, Laouan SE, Cote S, Gaudreau E, Drescher O, Ayotte P (2014) Evaluation of pyrethroid exposures in pregnant women from 10 Caribbean countries. Environ Int 63:201–206CrossRefPubMedGoogle Scholar
  11. Diez MC (2010) Biological aspects involved in the degradation of organic pollutants. J Soil Sci Plant Nutr 10:244–267CrossRefGoogle Scholar
  12. Ding Y, White CA, Muralidhara S, Bruckner JV, Bartlett MG (2004) Determination of deltamethrin and its metabolite 3-phenoxybenzoic acid in male rat plasma by high-performance liquid chromatography. J Chromatogr B 810:221–227CrossRefGoogle Scholar
  13. Fortes C, Mastroeni S, Pilla MA, Antonelli G, Lunghini L, Aprea C (2013) The relation between dietary habits and urinary levels of 3-phenoxybenzoic acid a pyrethroid metabolite. Food Chem Toxicol 52:91–96CrossRefPubMedGoogle Scholar
  14. Gaskin W, Guo HZ, Yin HJ, Xiong MD (2013) Identification and characterization of cotton genes involved in fuzz-fiber development. J Integr Plant Biol 57:619–630Google Scholar
  15. Gu X, Zhang G, Chen L, Dai R, Yu Y (2008) Persistence and dissipation of synthetic pyrethroid pesticides in red soils from the Yangtze River Delta area. Environ Geochem. Health 30:67–77CrossRefPubMedGoogle Scholar
  16. Guo P, Wang B, Hang B, Li L, Ali SW, He J, Li S (2009) Pyrethroid-degrading Sphingobium sp. JZ-2 and the purification and characterization of a novel pyrethroid hydrolase. Int Biodeterior Biodegrad 63:1107–1112CrossRefGoogle Scholar
  17. Halden RU, Tepp SM, Halden BG, Dwyer DF (1999) Degradation of 3-phenoxybenzoic acid in soil by Pseudomonas pseudoalcaligenes POB310 (pPOB) and two modified Pseudomonas strains. Appl Environ Microbiol 65:3354–3359PubMedCentralPubMedGoogle Scholar
  18. Hirosawa N, Ueyama J, Kondo T, Kamijima M, Takagi K, Fujinaka S, Hirate A, Hasegawa T, Wakusawa S (2011) Effect of DDVP on urinary excretion levels of pyrethroid metabolite 3-phenoxybenzoic acid in rats. Toxicol Lett 203:28–32CrossRefPubMedGoogle Scholar
  19. Katsuda Y (1999) Development of and future prospects for pyrethroid chemistry. J Pestic Sci 55:775–782CrossRefGoogle Scholar
  20. Lavado R, Li J, Rimoldi JM, Schlenk D (2014) Evaluation of the stereoselective biotransformation of permethrin in human liver microsomes: contributions of cytochrome P450 monooxygenases to the formation of estrogenic metabolites. Toxicol Lett 226:192–197CrossRefPubMedGoogle Scholar
  21. Liu S, Yao K, Jia D, Zhao N, Lai W, Yuan H (2012) A pretreatment method for HPLC analysis of cypermethrin in microbial degradation systems. J Chromatogr Sci 50:469–476CrossRefPubMedGoogle Scholar
  22. Liu F, Chi Y, Wu S, Jia D, Yao K (2014) Simultaneous degradation of cypermethrin and its metabolite 3-phenoxybenzoic acid by the cooperation of Bacillus licheniformis B-1 and Sphingomonas sp. SC-1. J Agric Food Chem 7:8256–8262CrossRefGoogle Scholar
  23. Lovley DR (2011) Live wires: direct extracellular electron exchange for bioenergy and the bioremediation of energy-related contamination. Energy Environ Sci 4:4896–4906CrossRefGoogle Scholar
  24. Maloney SE, Maule A, Smith AR (1993) Purification and preliminary characterization of permethrinase from a pyrethroid-transforming strain of Bacillus cereus. Appl Environ Microbiol 59:2007–2013PubMedCentralPubMedGoogle Scholar
  25. McCoy MR, Yang Z, Fu X, Ahn KC, Gee SJ, Bom DC, Zhong P, Chang D, Hammock BD (2012) Monitoring of total type II pyrethroid pesticides in citrus oils and water by converting to a common product 3-phenoxybenzoic acid. J Agric Food Chem 60:5065–5070PubMedCentralCrossRefPubMedGoogle Scholar
  26. Peng X, Huang J, Liu C, Xiang Z, Zhou J, Zhong G (2012) Biodegradation of bensulphuron-methyl by a novel Penicillium pinophilum strain BP-H-02. J Hazard Mater 213-214:216–221CrossRefPubMedGoogle Scholar
  27. Pinto AP, Serrano C, Pires T, Mestrinho E, Dias L, Teixeira DM, Caldeira AT (2012) Degradation of terbuthylazine difenoconazole and pendimethalin pesticides by selected fungi cultures. Sci Total Environ 435:402–410CrossRefPubMedGoogle Scholar
  28. Ruan Z, Zhai Y, Song J, Shi Y, Li K, Zhao B, Yan Y (2013) Molecular cloning and characterization of a newly isolated pyrethroid-degrading esterase gene from a genomic library of Ochrobactrum anthropi YZ-1. PLoS One 8:1–7Google Scholar
  29. Saikia N, Das SK, Patel BK, Niwas R, Singh A, Gopal M (2005) Biodegradation of beta-cyfluthrin by Pseudomonas stutzeri strain S1. Biodegradation 16:581–589CrossRefPubMedGoogle Scholar
  30. Shafer TJ, Meyer DA, Crofton KM (2005) Developmental neurotoxicity of pyrethroid insecticides: critical review and future research needs. Environ Health Perspect 113:123–136PubMedCentralCrossRefPubMedGoogle Scholar
  31. Shukla Y, Yadav A, Arora A (2002) Carcinogenic and cocarcinogenic potential of cypermethrin on mouse skin. Cancer Lett 182:33–41CrossRefPubMedGoogle Scholar
  32. Sun H, Chen W, Xu X, Ding Z, Chen X, Wang X (2014) Pyrethroid and their metabolite 3-phenoxybenzoic acid showed similar (anti) estrogenic activity in human and rat estrogen receptor α-mediated reporter gene assays. Environ Toxicol Pharmacol 37:371–377CrossRefPubMedGoogle Scholar
  33. Tallur P, Megadi V, Ninnekar H (2008) Biodegradation of cypermethrin by Micrococcus sp strain CPN 1. Biodegradation 19:77–82CrossRefPubMedGoogle Scholar
  34. Tang J, Yao K, Liu S, Jia D, Chi Y, Zeng C, Wu S (2013) Biodegradation of 3-phenoxybenzoic acid by a novel Sphingomonas sp. SC-1. Fresenius Environ Bull 22:1564–1572Google Scholar
  35. Topp E, Akhtar MH (1991) Identification and characterization of a Pseudomonas strain capable of metabolizing phenoxybenzoates. Appl Environ Microbiol 57:1294–1300PubMedCentralPubMedGoogle Scholar
  36. Wang C, Chen F, Zhang Q, Fang Z (2009) Chronic toxicity and cytotoxicity of synthetic pyrethroid insecticide cis-bifenthrin. J Environ Sci 21:1710–1715CrossRefGoogle Scholar
  37. Xie W, Zhou J, Wang H, Chen X (2008) Effect of nitrogen on the degradation of cypermethrin and its metabolite 3-phenoxybenzoic acid in soil. Pedosphere 18:638–644CrossRefGoogle Scholar
  38. Yu FB, Shan SD, Luo LP, Guan LB, Qin H (2013) Isolation and characterization of a Sphingomonas sp. strain F-7 degrading fenvalerate and its use in bioremediation of contaminated soil. J Environ Sci Health B 48:198–207CrossRefPubMedGoogle Scholar

Copyright information

© Springer-Verlag Berlin Heidelberg 2015

Authors and Affiliations

  • Weiqin Deng
    • 1
  • Derong Lin
    • 1
  • Kai Yao
    • 2
  • Huaiyu Yuan
    • 1
  • Zhilong Wang
    • 1
  • Jianlong Li
    • 1
  • Likou Zou
    • 3
  • Xinfeng Han
    • 1
  • Kang Zhou
    • 1
  • Li He
    • 1
  • Xinjie Hu
    • 1
  • Shuliang Liu
    • 1
  1. 1.College of Food ScienceSichuan Agricultural UniversityYa’anPeople’s Republic of China
  2. 2.College of Light Industry and FoodSichuan UniversityChengduPeople’s Republic of China
  3. 3.The Laboratory of Microbiology, Dujiangyan CampusSichuan Agricultural UniversityDujiangyanPeople’s Republic of China

Personalised recommendations