Effects of the earthworm Metaphire guillelmi on the mineralization, metabolism, and bound-residue formation of tetrabromobisphenol A (TBBPA) in soil

Gu, Jianqiang; Jing, Yuying; Ma, Yudao; Sun, Feifei; Wang, Lianhong; Chen, Jianqiu; Guo, Hongyan; Ji, Rong

doi:10.1016/j.scitotenv.2017.03.273

Cited by 25 publications

(11 citation statements)

References 41 publications

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“…They are generally considered as transformation products of TBBPA. Biotransformation from TBBPA to TBBPA DME and TBBPA MME has been reported in various studies (George and Häggblom, 2008; Sun et al, 2014a; Chen et al, 2017; Gu et al, 2017). Transformation ratio in mass or mole mass (TRM or TRMM, respectively) was used to describe the transformation efficiency from a parent compound to its metabolite.…”

Section: Introductionmentioning

confidence: 93%

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Biotransformation of tetrabromobisphenol A dimethyl ether back to tetrabromobisphenol A in whole pumpkin plants

Hou

Liu

et al. 2018

Environmental Pollution

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As the metabolites of tetrabromobisphenol A (TBBPA), tetrabromobisphenol A mono- and di-methyl ethers (TBBPA MME and TBBPA DME) have been detected in various environmental media. However, knowledge of the contribution of plants to their environmental fates, especially to the interactions between TBBPA DME and TBBPA, is quite limited. In this study, the metabolism and behaviors of TBBPA DME was studied with pumpkin plants through 15-day hydroponic exposure. The TBBPA were also studied separately using in-lab hydroponic exposure for comparison. The results showed that more TBBPA DME accumulated in pumpkin roots and translocated up to stems and leaves compared with TBBPA. Transformation of TBBPA DME occurred later and more slowly than that of TBBPA. Interconversion between TBBPA DME and TBBPA was verified in intact plants for the first time. Namely, TBBPA DME can be biotransformed to TBBPA MME (transformation ratio in mole mass, TRMM 0.50%) and to TBBPA (TRMM 0.53%) within pumpkin; and TBBPA can be biotransformed to TBBPA MME (TRMM 0.58%) and to TBBPA DME (TRMM 0.62%). In addition, two single benzene-ring metabolites, 2,6-dibromo-4-(2-(2-hydroxyl)-propyl)-anisole (DBHPA, TRMM 3.4%) with an O-methyl group and 2,6-dibromo-4-(2-(2-hydroxyl)-propyl)-phenetole (DBHPP, TRMM 0.57%) with an O-ethyl group, were identified as the transformation products in the TBBPA exposure experiments. The transformation and interconversion from TBBPA DME back to TBBPA is reported as a new pathway and potential source for TBBPA in the environment.

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Section: Introductionmentioning

confidence: 93%

“…TBBPA was transformed to TBBPA MME and TBBPA DME in the Kearny Marsh and Kymijoki sediments with reported TRMs of 10−50% (George and Häggblom, 2008). In soil, the earthworm Metaphire guillelmi enhanced the O -methylation transformation of TBBPA with a total TRM of 59.5 ± 5% (Gu et al, 2017).…”

Section: Introductionmentioning

confidence: 99%

Biotransformation of tetrabromobisphenol A dimethyl ether back to tetrabromobisphenol A in whole pumpkin plants

Hou

Liu

et al. 2018

Environmental Pollution

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“…Moreover, the substantially increased ratio of TBBPA-MAE/ TBBPA-BAE (3.4:1) in the soil samples compared with the original ratio in the commercial products (9:2 × 10 −3 :1) suggested that certain portions of TBBPA derivatives could transform to TBBPA mono-ether structural analogs in the environment (Liu et al 2017). In addition, the biotransformation from TBBPA to some TBBPA mono-ether structural analogs has been reported in various studies (Chen et al 2017;Gu et al 2017), suggesting that TBBPA could also contribute to the occurrence of environmental TBBPA monoether structural analogs.…”

Section: Introductionmentioning

confidence: 95%

Binding and Activity of Tetrabromobisphenol A Mono-Ether Structural Analogs to Thyroid Hormone Transport Proteins and Receptors

Ren

Yao

Xue

et al. 2020

Environ Health Perspect

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Background: Tetrabromobisphenol A (TBBPA) mono-ether structural analogs, identified as the by-products or transformation products of commercial TBBPA bis-ether derivatives, have been identified as emerging widespread pollutants. However, there is very little information regarding their toxicological effects. Objective: We aimed to explore the potential thyroid hormone (TH) system–disrupting effect of TBBPA mono-ether structural analogs. Methods: The binding potencies of chemicals toward human TH transport proteins [transthyretin (TTR) and thyroxine-binding globulin (TBG)] and receptors [ ligand-binding domain (LBD) and ] were determined by fluorescence competitive binding assays. Molecular docking was used to simulate the binding modes of the chemicals with the proteins. The cellular TR-disrupting potencies of chemicals were assessed by a GH3 cell proliferation assay. The intracellular concentrations of the chemicals were measured by high-performance liquid chromatography and mass spectrometry. Results: TBBPA mono-ether structural analogs bound to TTR with half maximal inhibitory concentrations ranging from to but did not bind to TBG. They also bound to both subtypes of TR-LBDs with 20% maximal inhibitory concentrations ranging from to . The docking results showed that the analogs fit into the ligand-binding pockets of TTR and TR-LBDs with binding modes similar to that of TBBPA. These compounds likely induced GH3 cell proliferation via TR [with the lowest effective concentrations (LOECs) ranging from to ] and further enhanced TH-induced GH3 cell proliferation (with LOECs ranging from to ). Compared with TBBPA, TBBPA-mono(2,3-dibromopropyl ether) showed a 4.18-fold higher GH3 cell proliferation effect and 105-fold higher cell membrane transportation ability. Conclusion: This study provided a possible mechanism underlying the difference in TTR or TR binding by novel TBBPA structural analogs. These compounds might exert TH system–disrupting effects by disrupting TH transport in circulation and TR activity in TH-responsive cells. https://doi.org/10.1289/EHP6498

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“…However, some scholars hold different views. Gu et al found that earthworms enriched soil organic matter, increasing the binding residues of flame retardants in the soil, which inhibited the degradation . The effects of earthworms toward the degradation of pollutants in soil were complicated.…”

Section: Introductionmentioning

confidence: 99%

“…Gu et al found that earthworms enriched soil organic matter, increasing the binding residues of flame retardants in the soil, which inhibited the degradation. 18 The effects of earthworms toward the degradation of pollutants in soil were complicated. Contaminants such as potentially toxic elements, pesticides, antibiotics, and so on in soil may influence earthworms.…”

Section: Introductionmentioning

confidence: 99%

Co-exposure of Monensin Increased the Risks of Atrazine to Earthworms

Jiang

Zhai

Liu

et al. 2022

Environ. Sci. Technol.

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Antibiotics could enter farmlands through sewage irrigation or manure application, causing combined pollution with pesticides. Antibiotics may affect the environmental fate of pesticides and even increase their bioavailability. In this study, the influence of monensin on the degradation, toxicity, and availability of atrazine in soil-earthworm microcosms was investigated. Monensin inhibited the degradation of atrazine, changed the metabolite patterns in soil, and increased the bioavailability of atrazine in earthworms. Atrazine and monensin had a significant synergistic effect on earthworms in the acute toxic test. In long-term toxicity tests, co-exposure of atrazine and monensin also led to worse effects on earthworms including oxidative stress, energy metabolism disruption, and cocoon production compared to single exposure. The expression of tight junction proteins was down-regulated significantly by monensin, indicating that the intestinal barrier of earthworms was weakened, possibly causing the increased bioavailability of atrazine. The expressions of heat shock protein 70 (Hsp70) and reproductive and ontogenetic factors (ANN, TCTP) were all downregulated in binary exposure, indicating that the resilience and cocoon production of earthworms were further weakened under combined pollution. Monensin disturbed the energy metabolism and weakened the intestinal barrier of earthworms. These results showed that monensin increased the risks of atrazine in agricultural areas.

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Effects of the earthworm Metaphire guillelmi on the mineralization, metabolism, and bound-residue formation of tetrabromobisphenol A (TBBPA) in soil

Cited by 25 publications

References 41 publications

Biotransformation of tetrabromobisphenol A dimethyl ether back to tetrabromobisphenol A in whole pumpkin plants

Biotransformation of tetrabromobisphenol A dimethyl ether back to tetrabromobisphenol A in whole pumpkin plants

Binding and Activity of Tetrabromobisphenol A Mono-Ether Structural Analogs to Thyroid Hormone Transport Proteins and Receptors

Co-exposure of Monensin Increased the Risks of Atrazine to Earthworms

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