Characterizing biotransformation products and pathways of the flame retardant triphenyl phosphate in Daphnia magna using non-target screening

Choi, Yeowool; Jeon, Junho; Choi, Young-Hun; Kim, Sang Don

doi:10.1016/j.scitotenv.2019.135106

Cited by 23 publications

(14 citation statements)

References 49 publications

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“…Hydroxylation is a typical biotransformation process of TPHP and is generally associated with CYP450. , However, the exact sites of hydroxylation, especially for dihydroxyl groups, are still controversial. , A recent study reported that TPHP could transform into glucuronic acid-conjugated and methoxy-conjugated products in wheat . For the first time, sulfate-conjugated products and hydration of cysteine-conjugated products of TPHP were identified in plants in this study, although they have been found in other organisms, such as humans and Daphnia magna . As a precursor of glutathione (GSH), cysteine may conjugate with xenobiotics for detoxification. , GSH may interact with water molecules via hydrogen bonding between the thiol groups of cysteine and H 2 O .…”

Section: Resultsmentioning

confidence: 62%

“…24 For the first time, sulfate-conjugated products and hydration of cysteine-conjugated products of TPHP were identified in plants in this study, although they have been found in other organisms, such as humans 17 and Daphnia magna. 38 As a precursor of glutathione (GSH), cysteine may conjugate with xenobiotics for detoxification. 57,58 GSH may interact with water molecules via hydrogen bonding between the thiol groups of cysteine and H 2 O.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…For the high-resolution mass spectrometry data, the mass accuracy of the detected mOPEs was set to less than 10 ppm. All of the biotransformation products of OPEs in the plants were selected by referring to the existing refs , , and using the EAWAG-BBD pathway prediction system () to perform the suspect screening. The suspect screening method was used to detect mOPEs with no commercial standard.…”

Section: Materials and Methodsmentioning

confidence: 99%

See 2 more Smart Citations

Phosphorus Deficiency Promoted Hydrolysis of Organophosphate Esters in Plants: Mechanisms and Transformation Pathways

Liu

Wang

Zhou

et al. 2021

Environ. Sci. Technol.

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The biotransformation of organophosphate esters (OPEs) in white lupin (Lupinus albus) and wheat (Triticum aestivum L.) was investigated in hydroponic experiments with different phosphorus (P)-containing conditions. The hydrolysis rates of OPEs followed the order of triphenyl phosphate (TPHP) > tri-n-butyl phosphate (TnBP) > tris(1,3-dichloro-2-propyl) phosphate (TDCPP). Hydrolysis of OPEs was accelerated at P-deficient conditions, and faster hydrolysis took place in white lupin than in wheat. Coincidingly, the production of acid phosphatase (ACP) in both plants was promoted, and much higher intracellular and extracellular ACPs were observed in white lupin under P-deficient conditions. In vitro experiments revealed that ACP was a key enzyme to hydrolyze OPEs. The hydrolysis rates of OPEs were significantly correlated with the Hirshfeld charges, calculated by density functional theory, of the oxygen atom in the single P–O bond. Using ultra-high-performance liquid chromatography coupled with Orbitrap Fusion mass spectrometer, 30 metabolites were successfully identified. Some of these metabolites, such as sulfate-conjugated products, hydration of cysteine-conjugated products of TPHP, and reductively dechlorinated metabolites of TDCPP, were observed for the first time in plants. It is noteworthy that OPEs may transform into many hydroxylated metabolites, and special attention should be paid to their potential environmental effects.

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Section: Resultsmentioning

confidence: 62%

Section: ■ Results and Discussionmentioning

confidence: 99%

Section: Materials and Methodsmentioning

confidence: 99%

See 1 more Smart Citation

Phosphorus Deficiency Promoted Hydrolysis of Organophosphate Esters in Plants: Mechanisms and Transformation Pathways

Liu

Wang

Zhou

et al. 2021

Environ. Sci. Technol.

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“…This product has the same structure as diphenyl phosphate, and the results were confirmed by comparison with the MS/MS fragment pattern of the reference standard (Figure 4e). TP_250 and TP_342 were detected as the same BTPs in invertebrates exposed to TPHP [21]. It could be inferred that hydrolysis and oxidation might occur with the biotransformation reactions of TPHP regardless of species.…”

Section: Triphenyl Phosphatementioning

confidence: 84%

Identification and Toxicity Prediction of Biotransformation Molecules of Organophosphate Flame Retardants by Microbial Reactions in a Wastewater Treatment Plant

Choi

Kim

2021

IJMS

Self Cite

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Organophosphate flame retardants (OPFRs) are substances added to plastics, textiles, and furniture, and are used as alternatives to brominated flame retardants. As the use of OPFRs increases in the manufacturing industry, the concentration in the aquatic environment is also increasing. In this study, OPFRs introduced into a wastewater treatment plant (WWTP) were identified, and the toxicity of biotransformation molecules generated by the biological reaction was predicted. Tris(2-butoxyethyl) phosphate, tris(2-butoxyethyl) phosphate, and triphenyl phosphate were selected as research analytes. Chemicals were analyzed using high-resolution mass spectrometry, and toxicity was predicted according to the structure. As a result, tris(1-chloro-2-propyl) phosphate showed the highest concentration, and the removal rate of OPFRs in the WWTP was 0–57%. A total of 15 biotransformation products were produced by microorganisms in the WWTP. Most of the biotransformation products were predicted to be less toxic than the parent compound, but some were highly toxic. These biotransformation products, as well as OPFRs, could flow into the water from the WWTP and affect the aquatic ecosystem.

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“…The effective concentration (EC) of TBBPA that affects 50% of daphnid mobility was less than 1 mg L −1 (48-h median EC [EC50] of 0.6 mg L −1 ; Waaijers et al 2013). Even though the concentration of TBBPA in the body fluid of D. magna has been reported (Choi et al 2020), to the best of our knowledge, there is no report on analytical methods based on DLLME using the whole organism for determining TBBPA bioaccumulation.…”

Section: Introductionmentioning

confidence: 99%

Application of Dispersive Liquid–Liquid Microextraction Followed by High‐Performance Liquid Chromatography/Tandem Mass Spectrometry Analysis to Determine Tetrabromobisphenol A in Complex Matrices

Macêdo

Bernegossi

Sabatini

et al. 2020

Enviro Toxic and Chemistry

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An accurate and sensitive ultrasound-dispersive liquid-liquid microextraction technique followed by highperformance liquid chromatography separation coupled with electrospray ionization tandem mass spectrometry detection method to determine the presence of tetrabromobisphenol A (TBBPA) in complex environmental matrices is proposed. The miniaturized procedure was used to extract and quantify the analyte in domestic sewage, anaerobic sludge, and the aquatic test organism species Daphnia magna and Chironomus sancticaroli, which are standardized organisms for ecotoxicity bioassays. Limits of detection of 2 ng L −1 (domestic sewage), 2 ng g −1 (anaerobic sludge), 0.25 ng g −1 (D. magna), and 5 ng g −1 (C. tentans) were obtained. The presence of TBBPA was determined in domestic sewage and anaerobic sludge from an anaerobic batch bioreactor at a concentration of 0.2 ± 0.03 μg L −1 and 507 ± 79 ng g −1 , respectively. In D. magna and C. sancticaroli exposed to TBBPA in an acute toxicity bioassay, the micropollutant accumulated at 3.74 and 8.87 μg g −1 , respectively. The proposed method is a simple and cost-effective tool to determine TBBPA environmental occurrence and biomagnification potential compared with conventional extraction methods. To the best of our knowledge, this is the first liquid-liquid miniaturized extraction method to be applied to D. magna and C. sancticaroli.

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Characterizing biotransformation products and pathways of the flame retardant triphenyl phosphate in Daphnia magna using non-target screening

Cited by 23 publications

References 49 publications

Phosphorus Deficiency Promoted Hydrolysis of Organophosphate Esters in Plants: Mechanisms and Transformation Pathways

Phosphorus Deficiency Promoted Hydrolysis of Organophosphate Esters in Plants: Mechanisms and Transformation Pathways

Identification and Toxicity Prediction of Biotransformation Molecules of Organophosphate Flame Retardants by Microbial Reactions in a Wastewater Treatment Plant

Application of Dispersive Liquid–Liquid Microextraction Followed by High‐Performance Liquid Chromatography/Tandem Mass Spectrometry Analysis to Determine Tetrabromobisphenol A in Complex Matrices

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