Journal article
New hydroxylated metabolites of 4-monochlorobiphenyl in whole poplar plants
Chemistry Central Journal, Vol.5(1), pp.1-9
12/2011
DOI: 10.1186/1752-153X-5-87
PMCID: PMC3260099
PMID: 22185578
Abstract
Two new monohydroxy metabolites of 4-monochlorobiphenyl (CB3) were positively identified using three newly synthesized monohydroxy compounds of CB3: 2-hydroxy-4-chlorobiphenyl (2OH-CB3), 3-hydroxy-4-chlorobiphenyl (3OH-CB3) and 4-hydroxy-3-chlorobiphenyl (4OH-CB2). New metabolites of CB3, including 2OH-CB3 and 3OH-CB3, were confirmed in whole poplars (Populus deltoides × nigra, DN34), a model plant in the application of phytoremediation. Furthermore, the concentrations and masses of 2OH-CB3 and 3OH-CB3 formed in various tissues of whole poplar plants and controls were measured. Results showed that 2OH-CB3 was the major product in these two OH-CB3s with chlorine and hydroxyl moieties in the same phenyl ring of CB3. Masses of 2OH-CB3 and 3OH-CB3 in tissues of whole poplar plants were much higher than those in the hydroponic solution, strongly indicating that the poplar plant itself metabolizes CB3 to both 2OH-CB3 and 3OH-CB3. The total yield of 2OH-CB3 and 3OH-CB3, with chlorine and hydroxyl in the same phenyl ring of CB3, was less than that of three previously found OH-CB3s with chlorine and hydroxyl in the opposite phenyl rings of CB3 (2'OH-CB3, 3'OH-CB3, and 4'OH-CB3). Finally, these two newly detected OH-CB3s from CB3 in this work also suggests that the metabolic pathway was via epoxide intermediates. These five OH-CB3s clearly showed the complete metabolism profile from CB3 to monohydroxylated CB3. More importantly, it's the first report and confirmation of 2OH-CB3 and 3OH-CB3 (new metabolites of CB3) in a living organism.
Details
- Title: Subtitle
- New hydroxylated metabolites of 4-monochlorobiphenyl in whole poplar plants
- Creators
- Guangshu Zhai - Department of Civil and Environmental Engineering and IIHR Hydroscience and Engineering The University of Iowa Iowa City IA 52242 USAHans-Joachim Lehmler - Department of Occupational and Environmental Health The University of Iowa Iowa City IA 52242 USAJerald Schnoor - Department of Occupational and Environmental Health The University of Iowa Iowa City IA 52242 USA
- Resource Type
- Journal article
- Publication Details
- Chemistry Central Journal, Vol.5(1), pp.1-9
- DOI
- 10.1186/1752-153X-5-87
- PMID
- 22185578
- PMCID
- PMC3260099
- NLM abbreviation
- Chem Cent J
- ISSN
- 1752-153X
- eISSN
- 1752-153X
- Publisher
- Springer International Publishing; Cham
- Language
- English
- Date published
- 12/2011
- Academic Unit
- Civil and Environmental Engineering; Occupational and Environmental Health; Iowa Neuroscience Institute
- Record Identifier
- 9983991968002771
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