Enantioselective transport and biotransformation of chiral hydroxylated metabolites of polychlorinated biphenyls in whole poplar plants.
Identifieur interne : 002255 ( Main/Exploration ); précédent : 002254; suivant : 002256Enantioselective transport and biotransformation of chiral hydroxylated metabolites of polychlorinated biphenyls in whole poplar plants.
Auteurs : Guangshu Zhai [États-Unis] ; Sarah M. Gutowski ; Hans-Joachim Lehmler ; Jerald L. SchnoorSource :
- Environmental science & technology [ 1520-5851 ] ; 2014.
Descripteurs français
- KwdFr :
- Biotransformation (MeSH), Culture hydroponique (MeSH), Dépollution biologique de l'environnement (MeSH), Hydroxylation (MeSH), Polychlorobiphényles (métabolisme), Polychlorobiphényles (toxicité), Populus (effets des médicaments et des substances chimiques), Populus (métabolisme), Stéréoisomérie (MeSH), Tiges de plante (MeSH), Transpiration des plantes (effets des médicaments et des substances chimiques), Transport biologique (MeSH).
- MESH :
- effets des médicaments et des substances chimiques : Populus, Transpiration des plantes.
- métabolisme : Polychlorobiphényles, Populus.
- toxicité : Polychlorobiphényles.
- Biotransformation, Culture hydroponique, Dépollution biologique de l'environnement, Hydroxylation, Stéréoisomérie, Tiges de plante, Transport biologique.
English descriptors
- KwdEn :
- Biodegradation, Environmental (MeSH), Biological Transport (MeSH), Biotransformation (MeSH), Hydroponics (MeSH), Hydroxylation (MeSH), Plant Stems (MeSH), Plant Transpiration (drug effects), Polychlorinated Biphenyls (metabolism), Polychlorinated Biphenyls (toxicity), Populus (drug effects), Populus (metabolism), Stereoisomerism (MeSH).
- MESH :
- chemical , metabolism : Polychlorinated Biphenyls.
- drug effects : Plant Transpiration, Populus.
- metabolism : Populus.
- chemical , toxicity : Polychlorinated Biphenyls.
- Biodegradation, Environmental, Biological Transport, Biotransformation, Hydroponics, Hydroxylation, Plant Stems, Stereoisomerism.
Abstract
Hydroxylated metabolites of polychlorinated biphenyls (OH-PCBs) have been found to be ubiquitous in the environment due to the oxidative metabolism of their parent PCBs. With more polarity, OH-PCBs may be more toxic and mobile than their parent compounds. However, the behavior and fate of OH-PCBs have been neglected in the environment because they are not the original contaminants. Some of these hydroxylated metabolites are chiral, and chiral compounds can be used to probe biological metabolic processes. Therefore, chiral OH-PCBs were selected to study their uptake, translocation, transformation, and enantioselectivity in plants in this work. Poplars (Populus deltoides × nigra, DN34), a model plant with complete genomic sequence, were hydroponically exposed to 5-hydroxy-2,2',3,4',6-pentachlorobiphenyl (5-OH-PCB91) and 5-hydroxy-2,2',3,5',6-pentachlorobiphenyl (5-OH-PCB95) for 10 days. Chiral 5-OH-PCB91 and 5-OH-PCB95 were clearly shown to be sorbed, taken up, and translocated in whole poplars, and they were detected in various tissues of whole poplars. However, the enantioselectivity of poplar for 5-OH-PCB91 and 5-OH-PCB95 proved to be quite different. The second-eluting enantiomer of OH-PCB95, separated on a chiral column (Phenomenex Lux Cellulose-1), was enantioselectively removed in whole poplar. Enantiomeric fractions in the middle xylem, top bark, top xylem, and stem, reached 0.803 ± 0.022, 0.643 ± 0.110, 0.835 ± 0.087, and 0.830 ± 0.029, respectively. Therefore, 5-OH-PCB95 was significantly enantioselectively biotransformed inside poplar tissues, in contrast to nearly racemic mixtures of 5-OH-PCB95 remaining in hydroponic solutions. Unlike 5-OH-PCB95, 5-OH-PCB91 remained nearly racemic in most tissues of whole poplars during 10 day exposure, suggesting the enantiomers of 5-OH-PCB91 were equally transported and metabolized in whole poplars. This is the first evidence of enantioselectivity of chiral OH-PCBs and suggests that poplars can enantioselectively biotransform at least one chiral OH-PCB: namely, 5-OH-PCB95.
DOI: 10.1021/es503443e
PubMed: 25238141
PubMed Central: PMC4207536
Affiliations:
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Schnoor</name></author></analytic><series><title level="j">Environmental science & technology</title><idno type="eISSN">1520-5851</idno><imprint><date when="2014" type="published">2014</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Biodegradation, Environmental (MeSH)</term><term>Biological Transport (MeSH)</term><term>Biotransformation (MeSH)</term><term>Hydroponics (MeSH)</term><term>Hydroxylation (MeSH)</term><term>Plant Stems (MeSH)</term><term>Plant Transpiration (drug effects)</term><term>Polychlorinated Biphenyls (metabolism)</term><term>Polychlorinated Biphenyls (toxicity)</term><term>Populus (drug effects)</term><term>Populus (metabolism)</term><term>Stereoisomerism (MeSH)</term></keywords><keywords scheme="KwdFr" xml:lang="fr"><term>Biotransformation (MeSH)</term><term>Culture hydroponique (MeSH)</term><term>Dépollution biologique de l'environnement (MeSH)</term><term>Hydroxylation (MeSH)</term><term>Polychlorobiphényles (métabolisme)</term><term>Polychlorobiphényles (toxicité)</term><term>Populus (effets des médicaments et des substances chimiques)</term><term>Populus (métabolisme)</term><term>Stéréoisomérie (MeSH)</term><term>Tiges de plante (MeSH)</term><term>Transpiration des plantes (effets des médicaments et des substances chimiques)</term><term>Transport biologique (MeSH)</term></keywords><keywords scheme="MESH" type="chemical" qualifier="metabolism" xml:lang="en"><term>Polychlorinated Biphenyls</term></keywords><keywords scheme="MESH" qualifier="drug effects" xml:lang="en"><term>Plant Transpiration</term><term>Populus</term></keywords><keywords scheme="MESH" qualifier="effets des médicaments et des substances chimiques" xml:lang="fr"><term>Populus</term><term>Transpiration des plantes</term></keywords><keywords scheme="MESH" qualifier="metabolism" xml:lang="en"><term>Populus</term></keywords><keywords scheme="MESH" qualifier="métabolisme" xml:lang="fr"><term>Polychlorobiphényles</term><term>Populus</term></keywords><keywords scheme="MESH" type="chemical" qualifier="toxicity" xml:lang="en"><term>Polychlorinated Biphenyls</term></keywords><keywords scheme="MESH" qualifier="toxicité" xml:lang="fr"><term>Polychlorobiphényles</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Biodegradation, Environmental</term><term>Biological Transport</term><term>Biotransformation</term><term>Hydroponics</term><term>Hydroxylation</term><term>Plant Stems</term><term>Stereoisomerism</term></keywords><keywords scheme="MESH" xml:lang="fr"><term>Biotransformation</term><term>Culture hydroponique</term><term>Dépollution biologique de l'environnement</term><term>Hydroxylation</term><term>Stéréoisomérie</term><term>Tiges de plante</term><term>Transport biologique</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">Hydroxylated metabolites of polychlorinated biphenyls (OH-PCBs) have been found to be ubiquitous in the environment due to the oxidative metabolism of their parent PCBs. With more polarity, OH-PCBs may be more toxic and mobile than their parent compounds. However, the behavior and fate of OH-PCBs have been neglected in the environment because they are not the original contaminants. Some of these hydroxylated metabolites are chiral, and chiral compounds can be used to probe biological metabolic processes. Therefore, chiral OH-PCBs were selected to study their uptake, translocation, transformation, and enantioselectivity in plants in this work. Poplars (Populus deltoides × nigra, DN34), a model plant with complete genomic sequence, were hydroponically exposed to 5-hydroxy-2,2',3,4',6-pentachlorobiphenyl (5-OH-PCB91) and 5-hydroxy-2,2',3,5',6-pentachlorobiphenyl (5-OH-PCB95) for 10 days. Chiral 5-OH-PCB91 and 5-OH-PCB95 were clearly shown to be sorbed, taken up, and translocated in whole poplars, and they were detected in various tissues of whole poplars. However, the enantioselectivity of poplar for 5-OH-PCB91 and 5-OH-PCB95 proved to be quite different. The second-eluting enantiomer of OH-PCB95, separated on a chiral column (Phenomenex Lux Cellulose-1), was enantioselectively removed in whole poplar. Enantiomeric fractions in the middle xylem, top bark, top xylem, and stem, reached 0.803 ± 0.022, 0.643 ± 0.110, 0.835 ± 0.087, and 0.830 ± 0.029, respectively. Therefore, 5-OH-PCB95 was significantly enantioselectively biotransformed inside poplar tissues, in contrast to nearly racemic mixtures of 5-OH-PCB95 remaining in hydroponic solutions. Unlike 5-OH-PCB95, 5-OH-PCB91 remained nearly racemic in most tissues of whole poplars during 10 day exposure, suggesting the enantiomers of 5-OH-PCB91 were equally transported and metabolized in whole poplars. This is the first evidence of enantioselectivity of chiral OH-PCBs and suggests that poplars can enantioselectively biotransform at least one chiral OH-PCB: namely, 5-OH-PCB95. </div></front></TEI><pubmed><MedlineCitation Status="MEDLINE" IndexingMethod="Curated" Owner="NLM"><PMID Version="1">25238141</PMID><DateCompleted><Year>2015</Year><Month>12</Month><Day>29</Day></DateCompleted><DateRevised><Year>2018</Year><Month>12</Month><Day>02</Day></DateRevised><Article PubModel="Print-Electronic"><Journal><ISSN IssnType="Electronic">1520-5851</ISSN><JournalIssue CitedMedium="Internet"><Volume>48</Volume><Issue>20</Issue><PubDate><Year>2014</Year><Month>Oct</Month><Day>21</Day></PubDate></JournalIssue><Title>Environmental science & technology</Title><ISOAbbreviation>Environ Sci Technol</ISOAbbreviation></Journal><ArticleTitle>Enantioselective transport and biotransformation of chiral hydroxylated metabolites of polychlorinated biphenyls in whole poplar plants.</ArticleTitle><Pagination><MedlinePgn>12213-20</MedlinePgn></Pagination><ELocationID EIdType="doi" ValidYN="Y">10.1021/es503443e</ELocationID><Abstract><AbstractText>Hydroxylated metabolites of polychlorinated biphenyls (OH-PCBs) have been found to be ubiquitous in the environment due to the oxidative metabolism of their parent PCBs. With more polarity, OH-PCBs may be more toxic and mobile than their parent compounds. However, the behavior and fate of OH-PCBs have been neglected in the environment because they are not the original contaminants. Some of these hydroxylated metabolites are chiral, and chiral compounds can be used to probe biological metabolic processes. Therefore, chiral OH-PCBs were selected to study their uptake, translocation, transformation, and enantioselectivity in plants in this work. Poplars (Populus deltoides × nigra, DN34), a model plant with complete genomic sequence, were hydroponically exposed to 5-hydroxy-2,2',3,4',6-pentachlorobiphenyl (5-OH-PCB91) and 5-hydroxy-2,2',3,5',6-pentachlorobiphenyl (5-OH-PCB95) for 10 days. Chiral 5-OH-PCB91 and 5-OH-PCB95 were clearly shown to be sorbed, taken up, and translocated in whole poplars, and they were detected in various tissues of whole poplars. However, the enantioselectivity of poplar for 5-OH-PCB91 and 5-OH-PCB95 proved to be quite different. The second-eluting enantiomer of OH-PCB95, separated on a chiral column (Phenomenex Lux Cellulose-1), was enantioselectively removed in whole poplar. Enantiomeric fractions in the middle xylem, top bark, top xylem, and stem, reached 0.803 ± 0.022, 0.643 ± 0.110, 0.835 ± 0.087, and 0.830 ± 0.029, respectively. Therefore, 5-OH-PCB95 was significantly enantioselectively biotransformed inside poplar tissues, in contrast to nearly racemic mixtures of 5-OH-PCB95 remaining in hydroponic solutions. Unlike 5-OH-PCB95, 5-OH-PCB91 remained nearly racemic in most tissues of whole poplars during 10 day exposure, suggesting the enantiomers of 5-OH-PCB91 were equally transported and metabolized in whole poplars. This is the first evidence of enantioselectivity of chiral OH-PCBs and suggests that poplars can enantioselectively biotransform at least one chiral OH-PCB: namely, 5-OH-PCB95. </AbstractText></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Zhai</LastName><ForeName>Guangshu</ForeName><Initials>G</Initials><AffiliationInfo><Affiliation>Department of Civil and Environmental Engineering and IIHR Hydroscience and Engineering, The University of Iowa , Iowa City, Iowa 52242, United States.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Gutowski</LastName><ForeName>Sarah M</ForeName><Initials>SM</Initials></Author><Author ValidYN="Y"><LastName>Lehmler</LastName><ForeName>Hans-Joachim</ForeName><Initials>HJ</Initials></Author><Author ValidYN="Y"><LastName>Schnoor</LastName><ForeName>Jerald L</ForeName><Initials>JL</Initials></Author></AuthorList><Language>eng</Language><GrantList CompleteYN="Y"><Grant><GrantID>P30 ES005605</GrantID><Acronym>ES</Acronym><Agency>NIEHS NIH HHS</Agency><Country>United States</Country></Grant><Grant><GrantID>P42 ES013661</GrantID><Acronym>ES</Acronym><Agency>NIEHS NIH HHS</Agency><Country>United States</Country></Grant><Grant><GrantID>P42ES013661</GrantID><Acronym>ES</Acronym><Agency>NIEHS NIH HHS</Agency><Country>United States</Country></Grant></GrantList><PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType><PublicationType UI="D052061">Research Support, N.I.H., Extramural</PublicationType><PublicationType UI="D013485">Research Support, Non-U.S. Gov't</PublicationType></PublicationTypeList><ArticleDate DateType="Electronic"><Year>2014</Year><Month>10</Month><Day>01</Day></ArticleDate></Article><MedlineJournalInfo><Country>United States</Country><MedlineTA>Environ Sci Technol</MedlineTA><NlmUniqueID>0213155</NlmUniqueID><ISSNLinking>0013-936X</ISSNLinking></MedlineJournalInfo><ChemicalList><Chemical><RegistryNumber>0YO8J06WCR</RegistryNumber><NameOfSubstance UI="C032904">2,2',3,5',6-pentachlorobiphenyl</NameOfSubstance></Chemical><Chemical><RegistryNumber>DFC2HB4I0K</RegistryNumber><NameOfSubstance UI="D011078">Polychlorinated Biphenyls</NameOfSubstance></Chemical></ChemicalList><CitationSubset>IM</CitationSubset><MeshHeadingList><MeshHeading><DescriptorName UI="D001673" MajorTopicYN="N">Biodegradation, Environmental</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D001692" MajorTopicYN="N">Biological Transport</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D001711" MajorTopicYN="N">Biotransformation</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D018527" MajorTopicYN="N">Hydroponics</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D006900" MajorTopicYN="N">Hydroxylation</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D018547" MajorTopicYN="N">Plant Stems</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D018526" MajorTopicYN="N">Plant Transpiration</DescriptorName><QualifierName UI="Q000187" MajorTopicYN="N">drug effects</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D011078" MajorTopicYN="N">Polychlorinated Biphenyls</DescriptorName><QualifierName UI="Q000378" MajorTopicYN="Y">metabolism</QualifierName><QualifierName UI="Q000633" MajorTopicYN="N">toxicity</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D032107" MajorTopicYN="N">Populus</DescriptorName><QualifierName UI="Q000187" MajorTopicYN="N">drug effects</QualifierName><QualifierName UI="Q000378" MajorTopicYN="Y">metabolism</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D013237" 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last="Gutowski">Sarah M. Gutowski</name><name sortKey="Lehmler, Hans Joachim" sort="Lehmler, Hans Joachim" uniqKey="Lehmler H" first="Hans-Joachim" last="Lehmler">Hans-Joachim Lehmler</name><name sortKey="Schnoor, Jerald L" sort="Schnoor, Jerald L" uniqKey="Schnoor J" first="Jerald L" last="Schnoor">Jerald L. Schnoor</name></noCountry><country name="États-Unis"><noRegion><name sortKey="Zhai, Guangshu" sort="Zhai, Guangshu" uniqKey="Zhai G" first="Guangshu" last="Zhai">Guangshu Zhai</name></noRegion></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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