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

Xingwang Hou; Miao Yu; Aifeng Liu; Yanlin Li; Ting Ruan; Jiyan Liu; Jerald L Schnoor; Guibin Jiang

doi:10.1016/j.envpol.2018.05.075

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

Xingwang Hou, Miao Yu, Aifeng Liu, Yanlin Li, Ting Ruan, Jiyan Liu, Jerald L Schnoor and Guibin Jiang

Environmental pollution (1987), Vol.241, pp.331-338

10/2018

DOI: 10.1016/j.envpol.2018.05.075

PMCID: PMC6351071

PMID: 29843015

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https://www.ncbi.nlm.nih.gov/pmc/articles/6351071View

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Abstract

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. [Display omitted] •More TBBPA DME translocated up to stems and leaves from roots compared with TBBPA.•TBBPA was metabolically transformed more quickly than TBBPA DME.•Interconversion between TBBPA and TBBPA DME was verified in intact pumpkin seedlings.•A metabolite of TBBPA with an O-ethyl group, was found in pumpkin for the first time. Interconversion between Tetrabromobisphenol A (TBBPA) and its dimethyl ether as well two single benzene-ring transformed compounds of TBBPA was found in the exposure of pumpkin.

Interconversion

Tetrabromobisphenol A monomethyl ether

Tetrabromobisphenol A dimethyl ether

Single benzene-ring compounds

Tetrabromobisphenol A

Details

Title: Subtitle: Biotransformation of tetrabromobisphenol A dimethyl ether back to tetrabromobisphenol A in whole pumpkin plants
Creators: 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
Miao Yu - 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
Aifeng Liu - CAS Key Laboratory of Biobased Materials, Qingdao Institute of Bioenergy and Bioprocess Technology, Chinese Academy of Sciences, Qingdao, 266101, China
Yanlin Li - 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
Ting Ruan - 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
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
Jerald L Schnoor - Department of Civil and Environmental Engineering, University of Iowa, Iowa City, IA, USA
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
Resource Type: Journal article
Publication Details: Environmental pollution (1987), Vol.241, pp.331-338
DOI: 10.1016/j.envpol.2018.05.075
PMID: 29843015
PMCID: PMC6351071
NLM abbreviation: Environ Pollut
ISSN: 0269-7491
eISSN: 1873-6424
Publisher: Elsevier Ltd
Grant note: name: National Key Basic Research Program of China, award: 2014CB441105; DOI: 10.13039/501100001809, name: National Natural Science Foundation of China, award: 21677158, 21621064; DOI: 10.13039/501100002367, name: Chinese Academy of Sciences, award: XDB14010400; name: Iowa Superfund Research Program; DOI: 10.13039/100000066, name: National Institute of Environmental Health Sciences, award: P42ES013661-12; name: 1000-Talents Program of the Chinese Academy of Sciences
Language: English
Date published: 10/2018
Academic Unit: Civil and Environmental Engineering; Occupational and Environmental Health; IIHR--Hydroscience and Engineering
Record Identifier: 9983997426702771

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