Journal article
Metabolization and degradation kinetics of the urban-use pesticide fipronil by white rot fungus Trametes versicolor
Environmental science--processes & impacts, Vol.18(10), pp.1256-1265
10/12/2016
DOI: 10.1039/c6em00344c
PMID: 27722395
Abstract
Fipronil is a recalcitrant phenylpyrazole-based pesticide used for flea/tick treatment and termite control that is distributed in urban aquatic environments via stormwater and contributes to stream toxicity. We discovered that fipronil is rapidly metabolized (t
= 4.2 d) by the white rot fungus Trametes versicolor to fipronil sulfone and multiple previously unknown fipronil transformation products, lowering fipronil concentration by 96.5%. Using an LC-QTOF-MS untargeted metabolomics approach, we identified four novel fipronil fungal transformation products: hydroxylated fipronil sulfone, glycosylated fipronil sulfone, and two compounds with unresolved structures. These results are consistent with identified enzymatic detoxification pathways wherein conjugation with sugar moieties follows initial ring functionalization (hydroxylation). The proposed pathway is supported by kinetic evidence of transformation product formation. Fipronil loss by sorption, hydrolysis, and photolysis was negligible. When T. versicolor was exposed to the cytochrome P450 enzyme inhibitor 1-aminobenzotriazole, oxidation of fipronil and production of hydroxylated and glycosylated transformation products significantly decreased (p = 0.038, 0.0037, 0.0023, respectively), indicating that fipronil is metabolized intracellularly by cytochrome P450 enzymes. Elucidating fipronil transformation products is critical because pesticide target specificity can be lost via structural alteration, broadening classes of impacted organisms. Integration of fungi in engineered natural treatment systems could be a viable strategy for pesticide removal from stormwater runoff.
Details
- Title: Subtitle
- Metabolization and degradation kinetics of the urban-use pesticide fipronil by white rot fungus Trametes versicolor
- Creators
- Jordyn M Wolfand - ReNUWIt Engineering Research Center, Stanford University, Stanford, CA, USA and Department of Civil & Environmental Engineering, Stanford University, 473 Via Ortega, Stanford, CA 94305, USA. luthy@stanford.eduGregory H LeFevre - ReNUWIt Engineering Research Center, Stanford University, Stanford, CA, USA and Department of Civil & Environmental Engineering, Stanford University, 473 Via Ortega, Stanford, CA 94305, USA. luthy@stanford.edu and Department of Civil & Environmental Engineering, University of Iowa, Iowa City, IA, USARichard G Luthy - ReNUWIt Engineering Research Center, Stanford University, Stanford, CA, USA and Department of Civil & Environmental Engineering, Stanford University, 473 Via Ortega, Stanford, CA 94305, USA. luthy@stanford.edu
- Resource Type
- Journal article
- Publication Details
- Environmental science--processes & impacts, Vol.18(10), pp.1256-1265
- Publisher
- England
- DOI
- 10.1039/c6em00344c
- PMID
- 27722395
- ISSN
- 2050-7895
- eISSN
- 2050-7895
- Grant note
- DOI: 10.13039/100000149, name: Division of Engineering Education and Centers, award: 1028968
- Language
- English
- Date published
- 10/12/2016
- Academic Unit
- Civil and Environmental Engineering
- Record Identifier
- 9983991953502771
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