Herbivore-induced poplar cytochrome P450 enzymes of the CYP71 family convert aldoximes to nitriles which repel a generalist caterpillar.
Identifieur interne : 002192 ( Main/Exploration ); précédent : 002191; suivant : 002193Herbivore-induced poplar cytochrome P450 enzymes of the CYP71 family convert aldoximes to nitriles which repel a generalist caterpillar.
Auteurs : Sandra Irmisch [Allemagne] ; Andrea Clavijo Mccormick ; Jan Günther ; Axel Schmidt ; Gerhard Andreas Boeckler ; Jonathan Gershenzon ; Sybille B. Unsicker ; Tobias G. KöllnerSource :
- The Plant journal : for cell and molecular biology [ 1365-313X ] ; 2014.
Descripteurs français
- KwdFr :
- Analyse de séquence d'ADN (MeSH), Animaux (MeSH), Composés organiques volatils (métabolisme), Composés organiques volatils (pharmacologie), Cytochrome P-450 enzyme system (génétique), Cytochrome P-450 enzyme system (métabolisme), Feuilles de plante (enzymologie), Feuilles de plante (génétique), Feuilles de plante (immunologie), Herbivorie (MeSH), Larve (MeSH), Nitriles (métabolisme), Oximes (composition chimique), Oximes (métabolisme), Papillons de nuit (effets des médicaments et des substances chimiques), Papillons de nuit (physiologie), Phylogenèse (MeSH), Populus (enzymologie), Populus (génétique), Populus (immunologie), Protéines végétales (génétique), Protéines végétales (métabolisme), Régulation de l'expression des gènes végétaux (MeSH).
- MESH :
- composition chimique : Oximes.
- effets des médicaments et des substances chimiques : Papillons de nuit.
- enzymologie : Feuilles de plante, Populus.
- génétique : Cytochrome P-450 enzyme system, Feuilles de plante, Populus, Protéines végétales.
- immunologie : Feuilles de plante, Populus.
- métabolisme : Composés organiques volatils, Cytochrome P-450 enzyme system, Nitriles, Oximes, Protéines végétales.
- pharmacologie : Composés organiques volatils.
- physiologie : Papillons de nuit.
- Analyse de séquence d'ADN, Animaux, Herbivorie, Larve, Phylogenèse, Régulation de l'expression des gènes végétaux.
English descriptors
- KwdEn :
- Animals (MeSH), Cytochrome P-450 Enzyme System (genetics), Cytochrome P-450 Enzyme System (metabolism), Gene Expression Regulation, Plant (MeSH), Herbivory (MeSH), Larva (MeSH), Moths (drug effects), Moths (physiology), Nitriles (metabolism), Oximes (chemistry), Oximes (metabolism), Phylogeny (MeSH), Plant Leaves (enzymology), Plant Leaves (genetics), Plant Leaves (immunology), Plant Proteins (genetics), Plant Proteins (metabolism), Populus (enzymology), Populus (genetics), Populus (immunology), Sequence Analysis, DNA (MeSH), Volatile Organic Compounds (metabolism), Volatile Organic Compounds (pharmacology).
- MESH :
- chemical , chemistry : Oximes.
- chemical , genetics : Cytochrome P-450 Enzyme System, Plant Proteins.
- chemical , metabolism : Cytochrome P-450 Enzyme System, Nitriles, Oximes, Plant Proteins, Volatile Organic Compounds.
- drug effects : Moths.
- enzymology : Plant Leaves, Populus.
- genetics : Plant Leaves, Populus.
- immunology : Plant Leaves, Populus.
- chemical , pharmacology : Volatile Organic Compounds.
- physiology : Moths.
- Animals, Gene Expression Regulation, Plant, Herbivory, Larva, Phylogeny, Sequence Analysis, DNA.
Abstract
Numerous plant species emit volatile nitriles upon herbivory, but the biosynthesis as well as the relevance of these nitrogenous compounds in plant-insect interactions remains unknown. Populus trichocarpa has been shown to produce a complex blend of nitrogenous volatiles, including aldoximes and nitriles, after herbivore attack. The aldoximes were previously reported to be derived from amino acids by the action of cytochrome P450 enzymes of the CYP79 family. Here we show that nitriles are derived from aldoximes by another type of P450 enzyme in P. trichocarpa. First, feeding of deuterium-labeled phenylacetaldoxime to poplar leaves resulted in incorporation of the label into benzyl cyanide, demonstrating that poplar volatile nitriles are derived from aldoximes. Then two P450 enzymes, CYP71B40v3 and CYP71B41v2, were characterized that produce aliphatic and aromatic nitriles from their respective aldoxime precursors. Both possess typical P450 sequence motifs but do not require added NADPH or cytochrome P450 reductase for catalysis. Since both enzymes are expressed after feeding by gypsy moth caterpillars, they are likely to be involved in herbivore-induced volatile nitrile emission in P. trichocarpa. Olfactometer experiments showed that these volatile nitriles have a strong repellent activity against gypsy moth caterpillars, suggesting they play a role in induced direct defense against poplar herbivores.
DOI: 10.1111/tpj.12711
PubMed: 25335755
Affiliations:
Links toward previous steps (curation, corpus...)
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Unsicker</name></author><author><name sortKey="Kollner, Tobias G" sort="Kollner, Tobias G" uniqKey="Kollner T" first="Tobias G" last="Köllner">Tobias G. Köllner</name></author></analytic><series><title level="j">The Plant journal : for cell and molecular biology</title><idno type="eISSN">1365-313X</idno><imprint><date when="2014" type="published">2014</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Animals (MeSH)</term><term>Cytochrome P-450 Enzyme System (genetics)</term><term>Cytochrome P-450 Enzyme System (metabolism)</term><term>Gene Expression Regulation, Plant (MeSH)</term><term>Herbivory (MeSH)</term><term>Larva (MeSH)</term><term>Moths (drug effects)</term><term>Moths (physiology)</term><term>Nitriles (metabolism)</term><term>Oximes (chemistry)</term><term>Oximes (metabolism)</term><term>Phylogeny (MeSH)</term><term>Plant Leaves (enzymology)</term><term>Plant Leaves (genetics)</term><term>Plant Leaves (immunology)</term><term>Plant Proteins (genetics)</term><term>Plant Proteins (metabolism)</term><term>Populus (enzymology)</term><term>Populus (genetics)</term><term>Populus (immunology)</term><term>Sequence Analysis, DNA (MeSH)</term><term>Volatile Organic Compounds (metabolism)</term><term>Volatile Organic Compounds (pharmacology)</term></keywords><keywords scheme="KwdFr" xml:lang="fr"><term>Analyse de séquence d'ADN (MeSH)</term><term>Animaux (MeSH)</term><term>Composés organiques volatils (métabolisme)</term><term>Composés organiques volatils (pharmacologie)</term><term>Cytochrome P-450 enzyme system (génétique)</term><term>Cytochrome P-450 enzyme system (métabolisme)</term><term>Feuilles de plante (enzymologie)</term><term>Feuilles de plante (génétique)</term><term>Feuilles de plante (immunologie)</term><term>Herbivorie (MeSH)</term><term>Larve (MeSH)</term><term>Nitriles (métabolisme)</term><term>Oximes (composition chimique)</term><term>Oximes (métabolisme)</term><term>Papillons de nuit (effets des médicaments et des substances chimiques)</term><term>Papillons de nuit (physiologie)</term><term>Phylogenèse (MeSH)</term><term>Populus (enzymologie)</term><term>Populus (génétique)</term><term>Populus (immunologie)</term><term>Protéines végétales (génétique)</term><term>Protéines végétales (métabolisme)</term><term>Régulation de l'expression des gènes végétaux (MeSH)</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Oximes</term></keywords><keywords scheme="MESH" type="chemical" qualifier="genetics" xml:lang="en"><term>Cytochrome P-450 Enzyme System</term><term>Plant Proteins</term></keywords><keywords scheme="MESH" type="chemical" qualifier="metabolism" xml:lang="en"><term>Cytochrome P-450 Enzyme System</term><term>Nitriles</term><term>Oximes</term><term>Plant Proteins</term><term>Volatile Organic Compounds</term></keywords><keywords scheme="MESH" qualifier="composition chimique" xml:lang="fr"><term>Oximes</term></keywords><keywords scheme="MESH" qualifier="drug effects" xml:lang="en"><term>Moths</term></keywords><keywords scheme="MESH" qualifier="effets des médicaments et des substances chimiques" xml:lang="fr"><term>Papillons de nuit</term></keywords><keywords scheme="MESH" qualifier="enzymologie" xml:lang="fr"><term>Feuilles de plante</term><term>Populus</term></keywords><keywords scheme="MESH" qualifier="enzymology" xml:lang="en"><term>Plant Leaves</term><term>Populus</term></keywords><keywords scheme="MESH" qualifier="genetics" xml:lang="en"><term>Plant Leaves</term><term>Populus</term></keywords><keywords scheme="MESH" qualifier="génétique" xml:lang="fr"><term>Cytochrome P-450 enzyme system</term><term>Feuilles de plante</term><term>Populus</term><term>Protéines végétales</term></keywords><keywords scheme="MESH" qualifier="immunologie" xml:lang="fr"><term>Feuilles de plante</term><term>Populus</term></keywords><keywords scheme="MESH" qualifier="immunology" xml:lang="en"><term>Plant Leaves</term><term>Populus</term></keywords><keywords scheme="MESH" qualifier="métabolisme" xml:lang="fr"><term>Composés organiques volatils</term><term>Cytochrome P-450 enzyme system</term><term>Nitriles</term><term>Oximes</term><term>Protéines végétales</term></keywords><keywords scheme="MESH" qualifier="pharmacologie" xml:lang="fr"><term>Composés organiques volatils</term></keywords><keywords scheme="MESH" type="chemical" qualifier="pharmacology" xml:lang="en"><term>Volatile Organic Compounds</term></keywords><keywords scheme="MESH" qualifier="physiologie" xml:lang="fr"><term>Papillons de nuit</term></keywords><keywords scheme="MESH" qualifier="physiology" xml:lang="en"><term>Moths</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Animals</term><term>Gene Expression Regulation, Plant</term><term>Herbivory</term><term>Larva</term><term>Phylogeny</term><term>Sequence Analysis, DNA</term></keywords><keywords scheme="MESH" xml:lang="fr"><term>Analyse de séquence d'ADN</term><term>Animaux</term><term>Herbivorie</term><term>Larve</term><term>Phylogenèse</term><term>Régulation de l'expression des gènes végétaux</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">Numerous plant species emit volatile nitriles upon herbivory, but the biosynthesis as well as the relevance of these nitrogenous compounds in plant-insect interactions remains unknown. Populus trichocarpa has been shown to produce a complex blend of nitrogenous volatiles, including aldoximes and nitriles, after herbivore attack. The aldoximes were previously reported to be derived from amino acids by the action of cytochrome P450 enzymes of the CYP79 family. Here we show that nitriles are derived from aldoximes by another type of P450 enzyme in P. trichocarpa. First, feeding of deuterium-labeled phenylacetaldoxime to poplar leaves resulted in incorporation of the label into benzyl cyanide, demonstrating that poplar volatile nitriles are derived from aldoximes. Then two P450 enzymes, CYP71B40v3 and CYP71B41v2, were characterized that produce aliphatic and aromatic nitriles from their respective aldoxime precursors. Both possess typical P450 sequence motifs but do not require added NADPH or cytochrome P450 reductase for catalysis. Since both enzymes are expressed after feeding by gypsy moth caterpillars, they are likely to be involved in herbivore-induced volatile nitrile emission in P. trichocarpa. Olfactometer experiments showed that these volatile nitriles have a strong repellent activity against gypsy moth caterpillars, suggesting they play a role in induced direct defense against poplar herbivores. </div></front></TEI><pubmed><MedlineCitation Status="MEDLINE" Owner="NLM"><PMID Version="1">25335755</PMID><DateCompleted><Year>2015</Year><Month>10</Month><Day>20</Day></DateCompleted><DateRevised><Year>2015</Year><Month>11</Month><Day>19</Day></DateRevised><Article PubModel="Print-Electronic"><Journal><ISSN IssnType="Electronic">1365-313X</ISSN><JournalIssue CitedMedium="Internet"><Volume>80</Volume><Issue>6</Issue><PubDate><Year>2014</Year><Month>Dec</Month></PubDate></JournalIssue><Title>The Plant journal : for cell and molecular biology</Title><ISOAbbreviation>Plant J</ISOAbbreviation></Journal><ArticleTitle>Herbivore-induced poplar cytochrome P450 enzymes of the CYP71 family convert aldoximes to nitriles which repel a generalist caterpillar.</ArticleTitle><Pagination><MedlinePgn>1095-107</MedlinePgn></Pagination><ELocationID EIdType="doi" ValidYN="Y">10.1111/tpj.12711</ELocationID><Abstract><AbstractText>Numerous plant species emit volatile nitriles upon herbivory, but the biosynthesis as well as the relevance of these nitrogenous compounds in plant-insect interactions remains unknown. Populus trichocarpa has been shown to produce a complex blend of nitrogenous volatiles, including aldoximes and nitriles, after herbivore attack. The aldoximes were previously reported to be derived from amino acids by the action of cytochrome P450 enzymes of the CYP79 family. Here we show that nitriles are derived from aldoximes by another type of P450 enzyme in P. trichocarpa. First, feeding of deuterium-labeled phenylacetaldoxime to poplar leaves resulted in incorporation of the label into benzyl cyanide, demonstrating that poplar volatile nitriles are derived from aldoximes. Then two P450 enzymes, CYP71B40v3 and CYP71B41v2, were characterized that produce aliphatic and aromatic nitriles from their respective aldoxime precursors. Both possess typical P450 sequence motifs but do not require added NADPH or cytochrome P450 reductase for catalysis. Since both enzymes are expressed after feeding by gypsy moth caterpillars, they are likely to be involved in herbivore-induced volatile nitrile emission in P. trichocarpa. Olfactometer experiments showed that these volatile nitriles have a strong repellent activity against gypsy moth caterpillars, suggesting they play a role in induced direct defense against poplar herbivores. </AbstractText><CopyrightInformation>© 2014 The Authors The Plant Journal © 2014 John Wiley & Sons Ltd.</CopyrightInformation></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Irmisch</LastName><ForeName>Sandra</ForeName><Initials>S</Initials><AffiliationInfo><Affiliation>Max Planck Institute for Chemical Ecology, Hans-Knöll-Strasse 8, 07745, Jena, Germany.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Clavijo McCormick</LastName><ForeName>Andrea</ForeName><Initials>A</Initials></Author><Author ValidYN="Y"><LastName>Günther</LastName><ForeName>Jan</ForeName><Initials>J</Initials></Author><Author ValidYN="Y"><LastName>Schmidt</LastName><ForeName>Axel</ForeName><Initials>A</Initials></Author><Author ValidYN="Y"><LastName>Boeckler</LastName><ForeName>Gerhard Andreas</ForeName><Initials>GA</Initials></Author><Author ValidYN="Y"><LastName>Gershenzon</LastName><ForeName>Jonathan</ForeName><Initials>J</Initials></Author><Author ValidYN="Y"><LastName>Unsicker</LastName><ForeName>Sybille B</ForeName><Initials>SB</Initials></Author><Author ValidYN="Y"><LastName>Köllner</LastName><ForeName>Tobias G</ForeName><Initials>TG</Initials></Author></AuthorList><Language>eng</Language><PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType><PublicationType UI="D013485">Research Support, Non-U.S. Gov't</PublicationType></PublicationTypeList><ArticleDate DateType="Electronic"><Year>2014</Year><Month>11</Month><Day>17</Day></ArticleDate></Article><MedlineJournalInfo><Country>England</Country><MedlineTA>Plant J</MedlineTA><NlmUniqueID>9207397</NlmUniqueID><ISSNLinking>0960-7412</ISSNLinking></MedlineJournalInfo><ChemicalList><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D009570">Nitriles</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D010091">Oximes</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D010940">Plant Proteins</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D055549">Volatile Organic Compounds</NameOfSubstance></Chemical><Chemical><RegistryNumber>7028-48-0</RegistryNumber><NameOfSubstance UI="C408881">phenylacetaldoxime</NameOfSubstance></Chemical><Chemical><RegistryNumber>9035-51-2</RegistryNumber><NameOfSubstance UI="D003577">Cytochrome P-450 Enzyme System</NameOfSubstance></Chemical><Chemical><RegistryNumber>ME6U10SD7D</RegistryNumber><NameOfSubstance UI="C023728">acetaldehyde oxime</NameOfSubstance></Chemical></ChemicalList><CitationSubset>IM</CitationSubset><MeshHeadingList><MeshHeading><DescriptorName UI="D000818" MajorTopicYN="N">Animals</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D003577" MajorTopicYN="N">Cytochrome P-450 Enzyme System</DescriptorName><QualifierName UI="Q000235" MajorTopicYN="N">genetics</QualifierName><QualifierName UI="Q000378" MajorTopicYN="N">metabolism</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D018506" MajorTopicYN="Y">Gene Expression Regulation, Plant</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D060434" MajorTopicYN="N">Herbivory</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D007814" MajorTopicYN="N">Larva</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D009036" MajorTopicYN="N">Moths</DescriptorName><QualifierName UI="Q000187" MajorTopicYN="Y">drug effects</QualifierName><QualifierName UI="Q000502" MajorTopicYN="N">physiology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D009570" MajorTopicYN="N">Nitriles</DescriptorName><QualifierName UI="Q000378" MajorTopicYN="Y">metabolism</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D010091" MajorTopicYN="N">Oximes</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName><QualifierName UI="Q000378" MajorTopicYN="Y">metabolism</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D010802" MajorTopicYN="N">Phylogeny</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D018515" MajorTopicYN="N">Plant Leaves</DescriptorName><QualifierName UI="Q000201" MajorTopicYN="N">enzymology</QualifierName><QualifierName UI="Q000235" MajorTopicYN="N">genetics</QualifierName><QualifierName UI="Q000276" MajorTopicYN="N">immunology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D010940" MajorTopicYN="N">Plant Proteins</DescriptorName><QualifierName UI="Q000235" MajorTopicYN="N">genetics</QualifierName><QualifierName UI="Q000378" MajorTopicYN="N">metabolism</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D032107" MajorTopicYN="N">Populus</DescriptorName><QualifierName UI="Q000201" MajorTopicYN="Y">enzymology</QualifierName><QualifierName UI="Q000235" MajorTopicYN="N">genetics</QualifierName><QualifierName UI="Q000276" MajorTopicYN="N">immunology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D017422" MajorTopicYN="N">Sequence Analysis, DNA</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D055549" MajorTopicYN="N">Volatile Organic Compounds</DescriptorName><QualifierName UI="Q000378" MajorTopicYN="N">metabolism</QualifierName><QualifierName UI="Q000494" MajorTopicYN="Y">pharmacology</QualifierName></MeshHeading></MeshHeadingList><KeywordList Owner="NOTNLM"><Keyword MajorTopicYN="N">CYP71</Keyword><Keyword MajorTopicYN="N">Populus trichocarpa</Keyword><Keyword MajorTopicYN="N">cytochrome P450</Keyword><Keyword MajorTopicYN="N">direct defense</Keyword><Keyword MajorTopicYN="N">nitriles</Keyword><Keyword MajorTopicYN="N">volatiles</Keyword></KeywordList></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="received"><Year>2014</Year><Month>09</Month><Day>04</Day></PubMedPubDate><PubMedPubDate PubStatus="revised"><Year>2014</Year><Month>10</Month><Day>16</Day></PubMedPubDate><PubMedPubDate PubStatus="accepted"><Year>2014</Year><Month>10</Month><Day>20</Day></PubMedPubDate><PubMedPubDate PubStatus="entrez"><Year>2014</Year><Month>10</Month><Day>23</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="pubmed"><Year>2014</Year><Month>10</Month><Day>23</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="medline"><Year>2015</Year><Month>10</Month><Day>21</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate></History><PublicationStatus>ppublish</PublicationStatus><ArticleIdList><ArticleId IdType="pubmed">25335755</ArticleId><ArticleId IdType="doi">10.1111/tpj.12711</ArticleId></ArticleIdList></PubmedData></pubmed><affiliations><list><country><li>Allemagne</li></country></list><tree><noCountry><name sortKey="Boeckler, Gerhard Andreas" sort="Boeckler, Gerhard Andreas" uniqKey="Boeckler G" first="Gerhard Andreas" last="Boeckler">Gerhard Andreas Boeckler</name><name sortKey="Clavijo Mccormick, Andrea" sort="Clavijo Mccormick, Andrea" uniqKey="Clavijo Mccormick A" first="Andrea" last="Clavijo Mccormick">Andrea Clavijo Mccormick</name><name sortKey="Gershenzon, Jonathan" sort="Gershenzon, Jonathan" uniqKey="Gershenzon J" first="Jonathan" last="Gershenzon">Jonathan Gershenzon</name><name sortKey="Gunther, Jan" sort="Gunther, Jan" uniqKey="Gunther J" first="Jan" last="Günther">Jan Günther</name><name sortKey="Kollner, Tobias G" sort="Kollner, Tobias G" uniqKey="Kollner T" first="Tobias G" last="Köllner">Tobias G. Köllner</name><name sortKey="Schmidt, Axel" sort="Schmidt, Axel" uniqKey="Schmidt A" first="Axel" last="Schmidt">Axel Schmidt</name><name sortKey="Unsicker, Sybille B" sort="Unsicker, Sybille B" uniqKey="Unsicker S" first="Sybille B" last="Unsicker">Sybille B. Unsicker</name></noCountry><country name="Allemagne"><noRegion><name sortKey="Irmisch, Sandra" sort="Irmisch, Sandra" uniqKey="Irmisch S" first="Sandra" last="Irmisch">Sandra Irmisch</name></noRegion></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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|type= RBID
|clé= pubmed:25335755
|texte= Herbivore-induced poplar cytochrome P450 enzymes of the CYP71 family convert aldoximes to nitriles which repel a generalist caterpillar.
}}
Pour générer des pages wiki
HfdIndexSelect -h $EXPLOR_AREA/Data/Main/Exploration/RBID.i -Sk "pubmed:25335755" \
| HfdSelect -Kh $EXPLOR_AREA/Data/Main/Exploration/biblio.hfd \
| NlmPubMed2Wicri -a PoplarV1
| This area was generated with Dilib version V0.6.37. |  |