3-Acyl dihydroflavonols from poplar resins collected by honey bees are active against the bee pathogens Paenibacillus larvae and Ascosphaera apis.
Identifieur interne : 001561 ( Main/Exploration ); précédent : 001560; suivant : 0015623-Acyl dihydroflavonols from poplar resins collected by honey bees are active against the bee pathogens Paenibacillus larvae and Ascosphaera apis.
Auteurs : Michael B. Wilson [États-Unis] ; Alison D. Pawlus [États-Unis] ; Doug Brinkman [États-Unis] ; Gary Gardner [États-Unis] ; Adrian D. Hegeman [États-Unis] ; Marla Spivak [États-Unis] ; Jerry D. Cohen [États-Unis]Source :
- Phytochemistry [ 1873-3700 ] ; 2017.
Descripteurs français
- KwdFr :
- Abeilles (MeSH), Animaux (MeSH), Anti-infectieux (composition chimique), Ascomycota (effets des médicaments et des substances chimiques), Flavonols (composition chimique), Fractionnement chimique (MeSH), Paenibacillus larvae (effets des médicaments et des substances chimiques), Populus (composition chimique), Propolis (composition chimique), Relation structure-activité (MeSH), Résines végétales (composition chimique), Tests de sensibilité microbienne (MeSH).
- MESH :
- composition chimique : Anti-infectieux, Flavonols, Populus, Propolis, Résines végétales.
- effets des médicaments et des substances chimiques : Ascomycota, Paenibacillus larvae.
- Abeilles, Animaux, Fractionnement chimique, Relation structure-activité, Tests de sensibilité microbienne.
English descriptors
- KwdEn :
- Animals (MeSH), Anti-Infective Agents (chemistry), Ascomycota (drug effects), Bees (MeSH), Chemical Fractionation (MeSH), Flavonols (chemistry), Microbial Sensitivity Tests (MeSH), Paenibacillus larvae (drug effects), Populus (chemistry), Propolis (chemistry), Resins, Plant (chemistry), Structure-Activity Relationship (MeSH).
- MESH :
- chemical , chemistry : Anti-Infective Agents, Flavonols, Propolis, Resins, Plant.
- chemistry : Populus.
- drug effects : Ascomycota, Paenibacillus larvae.
- Animals, Bees, Chemical Fractionation, Microbial Sensitivity Tests, Structure-Activity Relationship.
Abstract
Honey bees, Apis mellifera, collect antimicrobial plant resins from the environment and deposit them in their nests as propolis. This behavior is of practical concern to beekeepers since the presence of propolis in the hive has a variety of benefits, including the suppression of disease symptoms. To connect the benefits that bees derive from propolis with particular resinous plants, we determined the identity and botanical origin of propolis compounds active against bee pathogens using bioassay-guided fractionation against the bacterium Paenibacillus larvae, the causative agent of American foulbrood. Eleven dihydroflavonols were isolated from propolis collected in Fallon, NV, including pinobanksin-3-octanoate. This hitherto unknown derivative and five other 3-acyl-dihydroflavonols showed inhibitory activity against both P. larvae (IC50 = 17-68 μM) and Ascosphaera apis (IC50 = 8-23 μM), the fungal agent of chalkbrood. A structure-activity relationship between acyl group size and antimicrobial activity was found, with longer acyl groups increasing activity against P. larvae and shorter acyl groups increasing activity against A. apis. Finally, it was determined that the isolated 3-acyl-dihydroflavonols originated from Populus fremontii, and further analysis showed these compounds can also be found in other North American Populus spp.
DOI: 10.1016/j.phytochem.2017.02.020
PubMed: 28258722
Affiliations:
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Wilson</name><affiliation wicri:level="1"><nlm:affiliation>Department of Horticultural Science, Microbial and Plant Genomics Institute, University of Minnesota, 305 Alderman Hall, 1970 Folwell Ave, St. Paul, MN, 55108, USA; Department of Entomology, 219 Hodson Hall, 1980 Folwell Ave, St. Paul, MN, 55108, USA. Electronic address: wils0888@umn.edu.</nlm:affiliation><country xml:lang="fr">États-Unis</country><wicri:regionArea>Department of Horticultural Science, Microbial and Plant Genomics Institute, University of Minnesota, 305 Alderman Hall, 1970 Folwell Ave, St. Paul, MN, 55108, USA; Department of Entomology, 219 Hodson Hall, 1980 Folwell Ave, St. Paul, MN, 55108</wicri:regionArea><wicri:noRegion>55108</wicri:noRegion></affiliation></author><author><name sortKey="Pawlus, Alison D" sort="Pawlus, Alison D" uniqKey="Pawlus A" first="Alison D" last="Pawlus">Alison D. Pawlus</name><affiliation wicri:level="1"><nlm:affiliation>Department of Horticultural Science, Microbial and Plant Genomics Institute, University of Minnesota, 305 Alderman Hall, 1970 Folwell Ave, St. Paul, MN, 55108, USA; Aveda Corporation, 4000 Pheasant Ridge Dr. NE, Blaine, MN, 55449, USA. Electronic address: apawlus@aveda.com.</nlm:affiliation><country xml:lang="fr">États-Unis</country><wicri:regionArea>Department of Horticultural Science, Microbial and Plant Genomics Institute, University of Minnesota, 305 Alderman Hall, 1970 Folwell Ave, St. Paul, MN, 55108, USA; Aveda Corporation, 4000 Pheasant Ridge Dr. NE, Blaine, MN, 55449</wicri:regionArea><wicri:noRegion>55449</wicri:noRegion></affiliation></author><author><name sortKey="Brinkman, Doug" sort="Brinkman, Doug" uniqKey="Brinkman D" first="Doug" last="Brinkman">Doug Brinkman</name><affiliation wicri:level="1"><nlm:affiliation>Department of Horticultural Science, Microbial and Plant Genomics Institute, University of Minnesota, 305 Alderman Hall, 1970 Folwell Ave, St. Paul, MN, 55108, USA. Electronic address: brin0094@umn.edu.</nlm:affiliation><country xml:lang="fr">États-Unis</country><wicri:regionArea>Department of Horticultural Science, Microbial and Plant Genomics Institute, University of Minnesota, 305 Alderman Hall, 1970 Folwell Ave, St. Paul, MN, 55108</wicri:regionArea><wicri:noRegion>55108</wicri:noRegion></affiliation></author><author><name sortKey="Gardner, Gary" sort="Gardner, Gary" uniqKey="Gardner G" first="Gary" last="Gardner">Gary Gardner</name><affiliation wicri:level="1"><nlm:affiliation>Department of Horticultural Science, Microbial and Plant Genomics Institute, University of Minnesota, 305 Alderman Hall, 1970 Folwell Ave, St. Paul, MN, 55108, USA. Electronic address: ggardner@umn.edu.</nlm:affiliation><country xml:lang="fr">États-Unis</country><wicri:regionArea>Department of Horticultural Science, Microbial and Plant Genomics Institute, University of Minnesota, 305 Alderman Hall, 1970 Folwell Ave, St. Paul, MN, 55108</wicri:regionArea><wicri:noRegion>55108</wicri:noRegion></affiliation></author><author><name sortKey="Hegeman, Adrian D" sort="Hegeman, Adrian D" uniqKey="Hegeman A" first="Adrian D" last="Hegeman">Adrian D. Hegeman</name><affiliation wicri:level="1"><nlm:affiliation>Department of Horticultural Science, Microbial and Plant Genomics Institute, University of Minnesota, 305 Alderman Hall, 1970 Folwell Ave, St. Paul, MN, 55108, USA. Electronic address: hegem007@umn.edu.</nlm:affiliation><country xml:lang="fr">États-Unis</country><wicri:regionArea>Department of Horticultural Science, Microbial and Plant Genomics Institute, University of Minnesota, 305 Alderman Hall, 1970 Folwell Ave, St. Paul, MN, 55108</wicri:regionArea><wicri:noRegion>55108</wicri:noRegion></affiliation></author><author><name sortKey="Spivak, Marla" sort="Spivak, Marla" uniqKey="Spivak M" first="Marla" last="Spivak">Marla Spivak</name><affiliation wicri:level="1"><nlm:affiliation>Department of Entomology, 219 Hodson Hall, 1980 Folwell Ave, St. Paul, MN, 55108, USA. Electronic address: spiva001@umn.edu.</nlm:affiliation><country xml:lang="fr">États-Unis</country><wicri:regionArea>Department of Entomology, 219 Hodson Hall, 1980 Folwell Ave, St. Paul, MN, 55108</wicri:regionArea><wicri:noRegion>55108</wicri:noRegion></affiliation></author><author><name sortKey="Cohen, Jerry D" sort="Cohen, Jerry D" uniqKey="Cohen J" first="Jerry D" last="Cohen">Jerry D. Cohen</name><affiliation wicri:level="1"><nlm:affiliation>Department of Horticultural Science, Microbial and Plant Genomics Institute, University of Minnesota, 305 Alderman Hall, 1970 Folwell Ave, St. Paul, MN, 55108, USA. Electronic address: cohen047@umn.edu.</nlm:affiliation><country xml:lang="fr">États-Unis</country><wicri:regionArea>Department of Horticultural Science, Microbial and Plant Genomics Institute, University of Minnesota, 305 Alderman Hall, 1970 Folwell Ave, St. Paul, MN, 55108</wicri:regionArea><wicri:noRegion>55108</wicri:noRegion></affiliation></author></analytic><series><title level="j">Phytochemistry</title><idno type="eISSN">1873-3700</idno><imprint><date when="2017" type="published">2017</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Animals (MeSH)</term><term>Anti-Infective Agents (chemistry)</term><term>Ascomycota (drug effects)</term><term>Bees (MeSH)</term><term>Chemical Fractionation (MeSH)</term><term>Flavonols (chemistry)</term><term>Microbial Sensitivity Tests (MeSH)</term><term>Paenibacillus larvae (drug effects)</term><term>Populus (chemistry)</term><term>Propolis (chemistry)</term><term>Resins, Plant (chemistry)</term><term>Structure-Activity Relationship (MeSH)</term></keywords><keywords scheme="KwdFr" xml:lang="fr"><term>Abeilles (MeSH)</term><term>Animaux (MeSH)</term><term>Anti-infectieux (composition chimique)</term><term>Ascomycota (effets des médicaments et des substances chimiques)</term><term>Flavonols (composition chimique)</term><term>Fractionnement chimique (MeSH)</term><term>Paenibacillus larvae (effets des médicaments et des substances chimiques)</term><term>Populus (composition chimique)</term><term>Propolis (composition chimique)</term><term>Relation structure-activité (MeSH)</term><term>Résines végétales (composition chimique)</term><term>Tests de sensibilité microbienne (MeSH)</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Anti-Infective Agents</term><term>Flavonols</term><term>Propolis</term><term>Resins, Plant</term></keywords><keywords scheme="MESH" qualifier="chemistry" xml:lang="en"><term>Populus</term></keywords><keywords scheme="MESH" qualifier="composition chimique" xml:lang="fr"><term>Anti-infectieux</term><term>Flavonols</term><term>Populus</term><term>Propolis</term><term>Résines végétales</term></keywords><keywords scheme="MESH" qualifier="drug effects" xml:lang="en"><term>Ascomycota</term><term>Paenibacillus larvae</term></keywords><keywords scheme="MESH" qualifier="effets des médicaments et des substances chimiques" xml:lang="fr"><term>Ascomycota</term><term>Paenibacillus larvae</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Animals</term><term>Bees</term><term>Chemical Fractionation</term><term>Microbial Sensitivity Tests</term><term>Structure-Activity Relationship</term></keywords><keywords scheme="MESH" xml:lang="fr"><term>Abeilles</term><term>Animaux</term><term>Fractionnement chimique</term><term>Relation structure-activité</term><term>Tests de sensibilité microbienne</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">Honey bees, Apis mellifera, collect antimicrobial plant resins from the environment and deposit them in their nests as propolis. This behavior is of practical concern to beekeepers since the presence of propolis in the hive has a variety of benefits, including the suppression of disease symptoms. To connect the benefits that bees derive from propolis with particular resinous plants, we determined the identity and botanical origin of propolis compounds active against bee pathogens using bioassay-guided fractionation against the bacterium Paenibacillus larvae, the causative agent of American foulbrood. Eleven dihydroflavonols were isolated from propolis collected in Fallon, NV, including pinobanksin-3-octanoate. This hitherto unknown derivative and five other 3-acyl-dihydroflavonols showed inhibitory activity against both P. larvae (IC<sub>50</sub> = 17-68 μM) and Ascosphaera apis (IC<sub>50</sub> = 8-23 μM), the fungal agent of chalkbrood. A structure-activity relationship between acyl group size and antimicrobial activity was found, with longer acyl groups increasing activity against P. larvae and shorter acyl groups increasing activity against A. apis. Finally, it was determined that the isolated 3-acyl-dihydroflavonols originated from Populus fremontii, and further analysis showed these compounds can also be found in other North American Populus spp.</div></front></TEI><pubmed><MedlineCitation Status="MEDLINE" Owner="NLM"><PMID Version="1">28258722</PMID><DateCompleted><Year>2017</Year><Month>05</Month><Day>01</Day></DateCompleted><DateRevised><Year>2017</Year><Month>05</Month><Day>01</Day></DateRevised><Article PubModel="Print-Electronic"><Journal><ISSN IssnType="Electronic">1873-3700</ISSN><JournalIssue CitedMedium="Internet"><Volume>138</Volume><PubDate><Year>2017</Year><Month>Jun</Month></PubDate></JournalIssue><Title>Phytochemistry</Title><ISOAbbreviation>Phytochemistry</ISOAbbreviation></Journal><ArticleTitle>3-Acyl dihydroflavonols from poplar resins collected by honey bees are active against the bee pathogens Paenibacillus larvae and Ascosphaera apis.</ArticleTitle><Pagination><MedlinePgn>83-92</MedlinePgn></Pagination><ELocationID EIdType="pii" ValidYN="Y">S0031-9422(17)30091-2</ELocationID><ELocationID EIdType="doi" ValidYN="Y">10.1016/j.phytochem.2017.02.020</ELocationID><Abstract><AbstractText>Honey bees, Apis mellifera, collect antimicrobial plant resins from the environment and deposit them in their nests as propolis. This behavior is of practical concern to beekeepers since the presence of propolis in the hive has a variety of benefits, including the suppression of disease symptoms. To connect the benefits that bees derive from propolis with particular resinous plants, we determined the identity and botanical origin of propolis compounds active against bee pathogens using bioassay-guided fractionation against the bacterium Paenibacillus larvae, the causative agent of American foulbrood. Eleven dihydroflavonols were isolated from propolis collected in Fallon, NV, including pinobanksin-3-octanoate. This hitherto unknown derivative and five other 3-acyl-dihydroflavonols showed inhibitory activity against both P. larvae (IC<sub>50</sub> = 17-68 μM) and Ascosphaera apis (IC<sub>50</sub> = 8-23 μM), the fungal agent of chalkbrood. A structure-activity relationship between acyl group size and antimicrobial activity was found, with longer acyl groups increasing activity against P. larvae and shorter acyl groups increasing activity against A. apis. Finally, it was determined that the isolated 3-acyl-dihydroflavonols originated from Populus fremontii, and further analysis showed these compounds can also be found in other North American Populus spp.</AbstractText><CopyrightInformation>Copyright © 2017 Elsevier Ltd. All rights reserved.</CopyrightInformation></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Wilson</LastName><ForeName>Michael B</ForeName><Initials>MB</Initials><AffiliationInfo><Affiliation>Department of Horticultural Science, Microbial and Plant Genomics Institute, University of Minnesota, 305 Alderman Hall, 1970 Folwell Ave, St. Paul, MN, 55108, USA; Department of Entomology, 219 Hodson Hall, 1980 Folwell Ave, St. Paul, MN, 55108, USA. Electronic address: wils0888@umn.edu.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Pawlus</LastName><ForeName>Alison D</ForeName><Initials>AD</Initials><AffiliationInfo><Affiliation>Department of Horticultural Science, Microbial and Plant Genomics Institute, University of Minnesota, 305 Alderman Hall, 1970 Folwell Ave, St. Paul, MN, 55108, USA; Aveda Corporation, 4000 Pheasant Ridge Dr. NE, Blaine, MN, 55449, USA. Electronic address: apawlus@aveda.com.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Brinkman</LastName><ForeName>Doug</ForeName><Initials>D</Initials><AffiliationInfo><Affiliation>Department of Horticultural Science, Microbial and Plant Genomics Institute, University of Minnesota, 305 Alderman Hall, 1970 Folwell Ave, St. Paul, MN, 55108, USA. Electronic address: brin0094@umn.edu.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Gardner</LastName><ForeName>Gary</ForeName><Initials>G</Initials><AffiliationInfo><Affiliation>Department of Horticultural Science, Microbial and Plant Genomics Institute, University of Minnesota, 305 Alderman Hall, 1970 Folwell Ave, St. Paul, MN, 55108, USA. Electronic address: ggardner@umn.edu.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Hegeman</LastName><ForeName>Adrian D</ForeName><Initials>AD</Initials><AffiliationInfo><Affiliation>Department of Horticultural Science, Microbial and Plant Genomics Institute, University of Minnesota, 305 Alderman Hall, 1970 Folwell Ave, St. Paul, MN, 55108, USA. Electronic address: hegem007@umn.edu.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Spivak</LastName><ForeName>Marla</ForeName><Initials>M</Initials><AffiliationInfo><Affiliation>Department of Entomology, 219 Hodson Hall, 1980 Folwell Ave, St. Paul, MN, 55108, USA. Electronic address: spiva001@umn.edu.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Cohen</LastName><ForeName>Jerry D</ForeName><Initials>JD</Initials><AffiliationInfo><Affiliation>Department of Horticultural Science, Microbial and Plant Genomics Institute, University of Minnesota, 305 Alderman Hall, 1970 Folwell Ave, St. Paul, MN, 55108, USA. Electronic address: cohen047@umn.edu.</Affiliation></AffiliationInfo></Author></AuthorList><Language>eng</Language><PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType></PublicationTypeList><ArticleDate DateType="Electronic"><Year>2017</Year><Month>03</Month><Day>01</Day></ArticleDate></Article><MedlineJournalInfo><Country>England</Country><MedlineTA>Phytochemistry</MedlineTA><NlmUniqueID>0151434</NlmUniqueID><ISSNLinking>0031-9422</ISSNLinking></MedlineJournalInfo><ChemicalList><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D000890">Anti-Infective Agents</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D044948">Flavonols</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D012116">Resins, Plant</NameOfSubstance></Chemical><Chemical><RegistryNumber>9009-62-5</RegistryNumber><NameOfSubstance UI="D011429">Propolis</NameOfSubstance></Chemical></ChemicalList><CitationSubset>IM</CitationSubset><MeshHeadingList><MeshHeading><DescriptorName UI="D000818" MajorTopicYN="N">Animals</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D000890" MajorTopicYN="N">Anti-Infective Agents</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="Y">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D001203" MajorTopicYN="N">Ascomycota</DescriptorName><QualifierName UI="Q000187" MajorTopicYN="Y">drug effects</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D001516" MajorTopicYN="Y">Bees</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D005591" MajorTopicYN="N">Chemical Fractionation</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D044948" MajorTopicYN="N">Flavonols</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D008826" MajorTopicYN="N">Microbial Sensitivity Tests</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D000070059" MajorTopicYN="N">Paenibacillus larvae</DescriptorName><QualifierName UI="Q000187" MajorTopicYN="Y">drug effects</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D032107" MajorTopicYN="N">Populus</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="Y">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D011429" MajorTopicYN="N">Propolis</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D012116" MajorTopicYN="N">Resins, Plant</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="Y">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D013329" MajorTopicYN="N">Structure-Activity Relationship</DescriptorName></MeshHeading></MeshHeadingList><KeywordList Owner="NOTNLM"><Keyword MajorTopicYN="N">Antimicrobial activity</Keyword><Keyword MajorTopicYN="N">Ascospharea apis</Keyword><Keyword MajorTopicYN="N">Dihydroflavonol</Keyword><Keyword MajorTopicYN="N">Honey bees (Apis mellifera)</Keyword><Keyword MajorTopicYN="N">Paenibacillus larvae</Keyword><Keyword MajorTopicYN="N">Plant resins</Keyword><Keyword MajorTopicYN="N">Populus</Keyword><Keyword MajorTopicYN="N">Propolis</Keyword><Keyword MajorTopicYN="N">Salicaceae</Keyword></KeywordList></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="received"><Year>2016</Year><Month>09</Month><Day>02</Day></PubMedPubDate><PubMedPubDate PubStatus="revised"><Year>2017</Year><Month>02</Month><Day>09</Day></PubMedPubDate><PubMedPubDate PubStatus="accepted"><Year>2017</Year><Month>02</Month><Day>15</Day></PubMedPubDate><PubMedPubDate PubStatus="pubmed"><Year>2017</Year><Month>3</Month><Day>5</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="medline"><Year>2017</Year><Month>5</Month><Day>2</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="entrez"><Year>2017</Year><Month>3</Month><Day>5</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate></History><PublicationStatus>ppublish</PublicationStatus><ArticleIdList><ArticleId IdType="pubmed">28258722</ArticleId><ArticleId IdType="pii">S0031-9422(17)30091-2</ArticleId><ArticleId IdType="doi">10.1016/j.phytochem.2017.02.020</ArticleId></ArticleIdList></PubmedData></pubmed><affiliations><list><country><li>États-Unis</li></country></list><tree><country name="États-Unis"><noRegion><name sortKey="Wilson, Michael B" sort="Wilson, Michael B" uniqKey="Wilson M" first="Michael B" last="Wilson">Michael B. Wilson</name></noRegion><name sortKey="Brinkman, Doug" sort="Brinkman, Doug" uniqKey="Brinkman D" first="Doug" last="Brinkman">Doug Brinkman</name><name sortKey="Cohen, Jerry D" sort="Cohen, Jerry D" uniqKey="Cohen J" first="Jerry D" last="Cohen">Jerry D. Cohen</name><name sortKey="Gardner, Gary" sort="Gardner, Gary" uniqKey="Gardner G" first="Gary" last="Gardner">Gary Gardner</name><name sortKey="Hegeman, Adrian D" sort="Hegeman, Adrian D" uniqKey="Hegeman A" first="Adrian D" last="Hegeman">Adrian D. Hegeman</name><name sortKey="Pawlus, Alison D" sort="Pawlus, Alison D" uniqKey="Pawlus A" first="Alison D" last="Pawlus">Alison D. Pawlus</name><name sortKey="Spivak, Marla" sort="Spivak, Marla" uniqKey="Spivak M" first="Marla" last="Spivak">Marla Spivak</name></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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|texte= 3-Acyl dihydroflavonols from poplar resins collected by honey bees are active against the bee pathogens Paenibacillus larvae and Ascosphaera apis.
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