Enantioselective biodegradation of the pyrethroid (±)-lambda-cyhalothrin by marine-derived fungi

Birolli, Willian Garcia; Vacondio, Bruna; Alvarenga, Natália; Seleghim, Mirna Helena Regali; Porto, André Luiz Meleiro

doi:10.1016/j.chemosphere.2018.01.054

Cited by 61 publications

(17 citation statements)

References 25 publications

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“…Similar results have been observed with different strains of bacteria and fungi [59]. Several degradation mechanisms for cypermethrin and other pyrethroids have been identified in bacterial strains of Stenotrophomonas, Acinetobacter, Bacillus, Raoultella, Pseudomonas, and Brevibacterium, and fungal strains Aspergillus, Candidia, and Trichoderma [2,15,19,20,[59][60][61]. We propose the possible metabolic degradation pathway of cypermethrin with strain SG4 but, in natural conditions, the degradation could proceed via both biotic and abiotic reactions occurring in environmental conditions.…”

Section: Discussionsupporting

confidence: 83%

“…Several cypermethrin-degrading bacterial strains have been reported to effectively use the pesticide as a carbon and nitrogen source [15][16][17][18]. Microbial strains of genera Bacillus, Pseudomonas, Acinetobacter, Roultella, Aspergillus, Candida, Trichoderma, and Cunninghamella have been used for the degradation of cypermethrin and other pyrethroids [19][20][21][22][23][24]. These isolates can degrade up to 80% of cypermethrin in liquid media [21][22][23][24].…”

Section: Introductionmentioning

confidence: 99%

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Enhanced Cypermethrin Degradation Kinetics and Metabolic Pathway in Bacillus thuringiensis Strain SG4

et al. 2020

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Cypermethrin is popularly used as an insecticide in households and agricultural fields, resulting in serious environmental contamination. Rapid and effective techniques that minimize or remove insecticidal residues from the environment are urgently required. However, the currently available cypermethrin-degrading bacterial strains are suboptimal. We aimed to characterize the kinetics and metabolic pathway of highly efficient cypermethrin-degrading Bacillus thuringiensis strain SG4. Strain SG4 effectively degraded cypermethrin under different conditions. The maximum degradation was observed at 32 °C, pH 7.0, and a shaking speed of 110 rpm, and about 80% of the initial dose of cypermethrin (50 mg·L−1) was degraded in minimal salt medium within 15 days. SG4 cells immobilized with sodium alginate provided a higher degradation rate (85.0%) and lower half-life (t1/2) of 5.3 days compared to the 52.9 days of the control. Bioaugmentation of cypermethrin-contaminated soil slurry with strain SG4 significantly enhanced its biodegradation (83.3%). Analysis of the degradation products led to identification of nine metabolites of cypermethrin, which revealed that cypermethrin could be degraded first by cleavage of its ester bond, followed by degradation of the benzene ring, and subsequent metabolism. A new degradation pathway for cypermethrin was proposed based on analysis of the metabolites. We investigated the active role of B. thuringiensis strain SG4 in cypermethrin degradation under various conditions that could be applied in large-scale pollutant treatment.

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Section: Discussionsupporting

confidence: 83%

Section: Introductionmentioning

confidence: 99%

Enhanced Cypermethrin Degradation Kinetics and Metabolic Pathway in Bacillus thuringiensis Strain SG4

et al. 2020

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“…CBMAI 1829, Penicillium raistrickii CBMAI 931, and Cladosporium sp. HU [28][29][30]. Microorganisms-based SPs degradation causes ester cleavage to form 3-PBA which is further metabolized [31].…”

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confidence: 99%

New Insights into the Microbial Degradation of D-Cyphenothrin in Contaminated Water/Soil Environments

et al. 2020

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Persistent use of the insecticide D-cyphenothrin has resulted in heavy environmental contamination and public concern. However, microbial degradation of D-cyphenothrin has never been investigated and the mechanism remains unknown. During this study, for the first time, an efficient D-cyphenothrin-degrading bacterial strain Staphylococcus succinus HLJ-10 was identified. Response surface methodology was successfully employed by using Box-Behnken design to optimize the culture conditions. At optimized conditions, over 90% degradation of D-cyphenothrin (50 mg·L−1) was achieved in a mineral salt medium within 7 d. Kinetics analysis revealed that its half-life was reduced by 61.2 d, in comparison with the uninoculated control. Eight intermediate metabolites were detected in the biodegradation pathway of D-cyphenothrin including cis-D-cyphenothrin, trans-D-cyphenothrin, 3-phenoxybenzaldehyde, α-hydroxy-3-phenoxy-benzeneacetonitrile, trans-2,2-dimethyl-3-propenyl-cyclopropanol, 2,2-dimethyl-3-propenyl-cyclopropionic acid, trans-2,2-dimethyl-3-propenyl-cyclopropionaldehyde, and 1,2-benzenedicarboxylic acid, dipropyl ester. This is the first report about the degradation of D-cyphenothrin through cleavage of carboxylester linkage and diaryl bond. In addition to degradation of D-cyphenothrin, strain HLJ-10 effectively degraded a wide range of synthetic pyrethroids including permethrin, tetramethrin, bifenthrin, allethrin, and chlorempenthrin, which are also widely used insecticides with environmental contamination problems. Bioaugmentation of D-cyphenothrin-contaminated soils with strain HLJ-10 substantially enhanced its degradation and over 72% of D-phenothrin was removed from soils within 40 d. These findings unveil the biochemical basis of a highly efficient D-cyphenothrin-degrading bacterial isolate and provide potent agents for eliminating environmental residues of pyrethroids.

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“…There was a signal referring to a small concentration of 3-phenoxybenzaldehyde in the biodegradation analyses by GC-MS, but the same concentration was observed in the analysis of a pure standard of esfenvalerate at the same determined concentration of the sample. Therefore, this compound was generated by thermal instability of esfenvalerate at the analysis, as described in previous studies 8,20,25,28 with pyrethroids.…”

Section: Resultsmentioning

confidence: 99%

“…5 Several bacterial strains were isolated from different environments for biodegradation processes, i.e., contaminated soil, marine environment and activated sludge. [6][7][8][9][10] However, the major part of the literature aiming bioremediation of pyrethroids employed bacteria isolated from contaminated soil, since it is important that the biocatalyst presents an efficient biodegradation activity and a good development in the environmental conditions. Some examples were the biodegradation of cypermethrin by Pseudomonas aeruginosa GF31, Micrococcus sp.…”

Section: Introductionmentioning

confidence: 99%

Biodegradation of the Pyrethroid Pesticide Esfenvalerate by a Bacterial Consortium Isolated from Brazilian Savannah

Anjos¹,

Birolli²,

Porto³

2020

J. Braz. Chem. Soc.

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New biocatalysts for bioremediation techniques are necessary nowadays. Therefore, a bacterial consortium isolated from Brazilian Savannah was employed for biodegradation of 100 mg L −1 esfenvalerate in liquid culture medium. The bacterial consortium (Lysinibacillus xylanilyticus CBMAI2085, Bacillus cereus CBMAI2067, Lysinibacillus sp. CBMAI2051 and Bacillus sp. CBMAI2052) biodegraded this pyrethroid efficiently. The assays were conducted in triplicate, and after 12 days, 90% of the pesticide was degraded producing 3-phenoxybenzoic acid (35.0 ± 3.1 mg L −1 ) and 2-(4-chlorophenyl)-3-methylbutanoic acid (34.0 ± 2.8 mg L −1 ). The bacterial consortium (52 ± 5% biodegradation) was more efficient in the biodegradation than the average of the same strains solely employed (40 ± 7% biodegradation), showing that the use of consortia is an interesting approach. However, the strain Bacillus cereus CBMAI2067 (67 ± 3% biodegradation) was more efficient than the bacterial consortium, showing its potential as source of carboxylesterases and proving that, in this case, the use of a unique efficient strain is more adequate.

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Enantioselective biodegradation of the pyrethroid (±)-lambda-cyhalothrin by marine-derived fungi

Cited by 61 publications

References 25 publications

Enhanced Cypermethrin Degradation Kinetics and Metabolic Pathway in Bacillus thuringiensis Strain SG4

Enhanced Cypermethrin Degradation Kinetics and Metabolic Pathway in Bacillus thuringiensis Strain SG4

New Insights into the Microbial Degradation of D-Cyphenothrin in Contaminated Water/Soil Environments

Biodegradation of the Pyrethroid Pesticide Esfenvalerate by a Bacterial Consortium Isolated from Brazilian Savannah

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