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Glycosylation of Tetrabromobisphenol A in Pumpkin

  • Xingwang Hou
    Xingwang Hou
    State Key Laboratory of Environmental Chemistry and Ecotoxicology, Research Center for Eco-Environmental Sciences, Chinese Academy of Sciences, P.O. Box 2871, Beijing, 100085, China
    College of Resources and Environment, University of Chinese Academy of Sciences, Beijing, 100049, China
    More by Xingwang Hou
  • Miao Yu
    Miao Yu
    Department of Environmental Medical and Public Health, Icahn School of Medicine at Mount Sinai, New York, New York 10029, United States
    More by Miao Yu
  • Aifeng Liu
    Aifeng Liu
    CAS Key Laboratory of Biobased Materials, Qingdao Institute of Bioenergy and Bioprocess Technology, Chinese Academy of Sciences, Qingdao, 266101, China
    More by Aifeng Liu
  • Xiaoyun Wang
    Xiaoyun Wang
    State Key Laboratory of Environmental Chemistry and Ecotoxicology, Research Center for Eco-Environmental Sciences, Chinese Academy of Sciences, P.O. Box 2871, Beijing, 100085, China
    College of Resources and Environment, University of Chinese Academy of Sciences, Beijing, 100049, China
    More by Xiaoyun Wang
  • Yanlin Li
    Yanlin Li
    Department of Civil and Environmental Engineering, University of Iowa, Iowa City, Iowa 52242, United States
    More by Yanlin Li
  • Jiyan Liu*
    Jiyan Liu
    State Key Laboratory of Environmental Chemistry and Ecotoxicology, Research Center for Eco-Environmental Sciences, Chinese Academy of Sciences, P.O. Box 2871, Beijing, 100085, China
    College of Resources and Environment, University of Chinese Academy of Sciences, Beijing, 100049, China
    *Phone: 8610-62849334; fax: 8610-62849339; e-mail: [email protected]
    More by Jiyan Liu
  • Jerald L. Schnoor
    Jerald L. Schnoor
    Department of Civil and Environmental Engineering, University of Iowa, Iowa City, Iowa 52242, United States
  • , and 
  • Guibin Jiang
    Guibin Jiang
    State Key Laboratory of Environmental Chemistry and Ecotoxicology, Research Center for Eco-Environmental Sciences, Chinese Academy of Sciences, P.O. Box 2871, Beijing, 100085, China
    College of Resources and Environment, University of Chinese Academy of Sciences, Beijing, 100049, China
    More by Guibin Jiang
Cite this: Environ. Sci. Technol. 2019, 53, 15, 8805–8812
Publication Date (Web):June 25, 2019
https://doi.org/10.1021/acs.est.9b02122
Copyright © 2019 American Chemical Society
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Supporting Info (1)»

Abstract

Abstract Image

Tetrabromobisphenol A (TBBPA) is the most widely used brominated flame retardant (BFR), and it bioaccumulates throughout the food chains. Its fate in the first trophic level, plants, is of special interest. In this study, a four-day hydroponic exposure of TBBPA at a concentration of 1 μmol L–1 to pumpkin seedlings was conducted. A nontarget screening method for hydrophilic bromine-containing metabolites was modified, based on both typical isotope patterns of bromine and mass defect, and used to process mass spectra data. A total of 20 glycosylation and malonyl glycosylation metabolites were found for TBBPA in the pumpkin plants. Representative glycosyl TBBPA reference standards were synthesized to evaluate the contribution of this glycosylation process. Approximately 86% of parent TBBPA was metabolized to form those 20 glycosyl TBBPAs, showing that glycosylation was the most dominant metabolism pathway for TBBPA in pumpkin at the tested exposure concentration.

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The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.est.9b02122.

  • Synthetic routes of five glycosyl TBBPA standards; NMR and MS2 of five gycosyl TBBPA standards; algorithm of findbr; additional figures and tables (PDF)

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Cited By


This article is cited by 8 publications.

  1. Shaochen Pang, Yue Gao, Aijing Li, Xinglei Yao, Guangbo Qu, Ligang Hu, Yong Liang, Maoyong Song, Guibin Jiang. Tetrabromobisphenol A Perturbs Erythropoiesis and Impairs Blood Circulation in Zebrafish Embryos. Environmental Science & Technology 2020, Article ASAP.
  2. Weifang Chen, Miao Yu, Qing Zhang, Xingwang Hou, Wenqian Kong, Linfeng Wei, Xiaowei Mao, Jiyan Liu, Jerald L. Schnoor, Guibin Jiang. Metabolism of SCCPs and MCCPs in Suspension Rice Cells Based on Paired Mass Distance (PMD) Analysis. Environmental Science & Technology 2020, 54 (16) , 9990-9999. https://doi.org/10.1021/acs.est.0c01830
  3. Qian S. Liu, Zhendong Sun, Xiaomin Ren, Zhihua Ren, Aifeng Liu, Jianqing Zhang, Qunfang Zhou, Guibin Jiang. Chemical Structure-Related Adipogenic Effects of Tetrabromobisphenol A and Its Analogues on 3T3-L1 Preadipocytes. Environmental Science & Technology 2020, 54 (10) , 6262-6271. https://doi.org/10.1021/acs.est.0c00624
  4. Ge Guan, Huilan Su, Xiaoran Wei, Yuxin Zheng, Xiaoting Jin. The promotion of tetrabromobisphenol A exposure on Ishikawa cells proliferation and pivotal role of ubiquitin-mediated IκB′ degradation. Ecotoxicology and Environmental Safety 2021, 207 , 111254. https://doi.org/10.1016/j.ecoenv.2020.111254
  5. Hongna Zhang, Yao Lu, Yanshan Liang, Lilong Jiang, Zongwei Cai. Triclocarban-induced responses of endogenous and xenobiotic metabolism in human hepatic cells: Toxicity assessment based on nontargeted metabolomics approach. Journal of Hazardous Materials 2020, 392 , 122475. https://doi.org/10.1016/j.jhazmat.2020.122475
  6. Yongcan Jiang, Haoliang Lu, Kang Xia, Qiang Wang, Jinjin Yang, Hualong Hong, Jingchun Liu, Chonglin Yan. Effect of mangrove species on removal of tetrabromobisphenol A from contaminated sediments. Chemosphere 2020, 244 , 125385. https://doi.org/10.1016/j.chemosphere.2019.125385
  7. Yongcan Jiang, Haoliang Lu, Yazhi Wang, Hualong Hong, Qiang Wang, Jingchun Liu, Chongling Yan. Uptake, biotransformation and physiological response of TBBPA in mangrove plants after hydroponics exposure. Marine Pollution Bulletin 2020, 151 , 110832. https://doi.org/10.1016/j.marpolbul.2019.110832
  8. Ramces De-Jesús-García, Ulises Rosas, Joseph G. Dubrovsky. The barrier function of plant roots: biological bases for selective uptake and avoidance of soil compounds. Functional Plant Biology 2020, 47 (5) , 383. https://doi.org/10.1071/FP19144

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