Structure elucidation of anti-methicillin resistant Staphylococcus aureus (MRSA) flavonoids from balsam poplar buds.
Identifieur interne : 001655 ( Main/Exploration ); précédent : 001654; suivant : 001656Structure elucidation of anti-methicillin resistant Staphylococcus aureus (MRSA) flavonoids from balsam poplar buds.
Auteurs : François Simard [Canada] ; Charles Gauthier [Canada] ; Jean Legault [Canada] ; Serge Lavoie [Canada] ; Vakhtang Mshvildadze [Canada] ; André Pichette [Canada]Source :
- Bioorganic & medicinal chemistry [ 1464-3391 ] ; 2016.
Descripteurs français
- KwdFr :
- Antibactériens (biosynthèse), Antibactériens (composition chimique), Antibactériens (isolement et purification), Antibactériens (pharmacologie), Cinnamates (composition chimique), Cinnamates (isolement et purification), Cinnamates (pharmacologie), Flavonoïdes (biosynthèse), Flavonoïdes (composition chimique), Flavonoïdes (isolement et purification), Flavonoïdes (pharmacologie), Gentamicine (pharmacologie), Modèles moléculaires (MeSH), Populus (composition chimique), Relation structure-activité (MeSH), Staphylococcus aureus résistant à la méticilline (effets des médicaments et des substances chimiques), Staphylococcus aureus résistant à la méticilline (isolement et purification), Stéréoisomérie (MeSH).
- MESH :
- biosynthèse : Antibactériens, Flavonoïdes.
- composition chimique : Antibactériens, Cinnamates, Flavonoïdes, Populus.
- effets des médicaments et des substances chimiques : Staphylococcus aureus résistant à la méticilline.
- isolement et purification : Antibactériens, Cinnamates, Flavonoïdes, Staphylococcus aureus résistant à la méticilline.
- pharmacologie : Antibactériens, Cinnamates, Flavonoïdes, Gentamicine.
- Modèles moléculaires, Relation structure-activité, Stéréoisomérie.
English descriptors
- KwdEn :
- Anti-Bacterial Agents (biosynthesis), Anti-Bacterial Agents (chemistry), Anti-Bacterial Agents (isolation & purification), Anti-Bacterial Agents (pharmacology), Cinnamates (chemistry), Cinnamates (isolation & purification), Cinnamates (pharmacology), Flavonoids (biosynthesis), Flavonoids (chemistry), Flavonoids (isolation & purification), Flavonoids (pharmacology), Gentamicins (pharmacology), Methicillin-Resistant Staphylococcus aureus (drug effects), Methicillin-Resistant Staphylococcus aureus (isolation & purification), Models, Molecular (MeSH), Populus (chemistry), Stereoisomerism (MeSH), Structure-Activity Relationship (MeSH).
- MESH :
- chemical , biosynthesis : Anti-Bacterial Agents, Flavonoids.
- chemical , chemistry : Anti-Bacterial Agents, Cinnamates, Flavonoids.
- chemical , isolation & purification : Anti-Bacterial Agents, Cinnamates, Flavonoids.
- chemical , pharmacology : Anti-Bacterial Agents, Cinnamates, Flavonoids, Gentamicins.
- chemistry : Populus.
- drug effects : Methicillin-Resistant Staphylococcus aureus.
- isolation & purification : Methicillin-Resistant Staphylococcus aureus.
- Models, Molecular, Stereoisomerism, Structure-Activity Relationship.
Abstract
There is nowadays an urgent need for developing novel generations of antibiotic agents due to the increased resistance of pathogenic bacteria. As a rich reservoir of structurally diverse compounds, plant species hold promise in this regard. Within this framework, we isolated a unique series of antibacterial flavonoids, named balsacones N-U, featuring multiple cinnamyl chains on the flavan skeleton. The structures of these compounds, isolated as racemates, were determined using extensive 1D and 2D NMR analysis in tandem with HRMS. Balsacones N-U along with previously isolated balsacones A-M were evaluated for their antibacterial activity against clinical isolates of methicillin resistant Staphylococcus aureus (MRSA). Several of the tested balsacones were potent anti-MRSA agents showing MIC values in the low micromolar range. Structure-activity relationships study highlighted some important parameters involved in the antibacterial activity of balsacones such as the presence of cinnamyl and cinnamoyl chains at the C-3 and C-8 positions of the flavan skeleton, respectively. These results suggest that balsacones could represent a potential novel class of naturally occurring anti-MRSA agents.
DOI: 10.1016/j.bmc.2016.07.009
PubMed: 27436809
Affiliations:
Links toward previous steps (curation, corpus...)
Le document en format XML
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Electronic address: andre_pichette@uqac.ca.</nlm:affiliation><country xml:lang="fr">Canada</country><wicri:regionArea>Laboratoire LASEVE, Département des Sciences Fondamentales, Université du Québec à Chicoutimi, 555, boul. de l'Université, Chicoutimi (Québec) G7H 2B1</wicri:regionArea><wicri:noRegion>Chicoutimi (Québec) G7H 2B1</wicri:noRegion></affiliation></author></analytic><series><title level="j">Bioorganic & medicinal chemistry</title><idno type="eISSN">1464-3391</idno><imprint><date when="2016" type="published">2016</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Anti-Bacterial Agents (biosynthesis)</term><term>Anti-Bacterial Agents (chemistry)</term><term>Anti-Bacterial Agents (isolation & purification)</term><term>Anti-Bacterial Agents (pharmacology)</term><term>Cinnamates (chemistry)</term><term>Cinnamates (isolation & purification)</term><term>Cinnamates (pharmacology)</term><term>Flavonoids (biosynthesis)</term><term>Flavonoids (chemistry)</term><term>Flavonoids (isolation & purification)</term><term>Flavonoids (pharmacology)</term><term>Gentamicins (pharmacology)</term><term>Methicillin-Resistant Staphylococcus aureus (drug effects)</term><term>Methicillin-Resistant Staphylococcus aureus (isolation & purification)</term><term>Models, Molecular (MeSH)</term><term>Populus (chemistry)</term><term>Stereoisomerism (MeSH)</term><term>Structure-Activity Relationship (MeSH)</term></keywords><keywords scheme="KwdFr" xml:lang="fr"><term>Antibactériens (biosynthèse)</term><term>Antibactériens (composition chimique)</term><term>Antibactériens (isolement et purification)</term><term>Antibactériens (pharmacologie)</term><term>Cinnamates (composition chimique)</term><term>Cinnamates (isolement et purification)</term><term>Cinnamates (pharmacologie)</term><term>Flavonoïdes (biosynthèse)</term><term>Flavonoïdes (composition chimique)</term><term>Flavonoïdes (isolement et purification)</term><term>Flavonoïdes (pharmacologie)</term><term>Gentamicine (pharmacologie)</term><term>Modèles moléculaires (MeSH)</term><term>Populus (composition chimique)</term><term>Relation structure-activité (MeSH)</term><term>Staphylococcus aureus résistant à la méticilline (effets des médicaments et des substances chimiques)</term><term>Staphylococcus aureus résistant à la méticilline (isolement et purification)</term><term>Stéréoisomérie (MeSH)</term></keywords><keywords scheme="MESH" type="chemical" qualifier="biosynthesis" xml:lang="en"><term>Anti-Bacterial Agents</term><term>Flavonoids</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Anti-Bacterial Agents</term><term>Cinnamates</term><term>Flavonoids</term></keywords><keywords scheme="MESH" type="chemical" qualifier="isolation & purification" xml:lang="en"><term>Anti-Bacterial Agents</term><term>Cinnamates</term><term>Flavonoids</term></keywords><keywords scheme="MESH" type="chemical" qualifier="pharmacology" xml:lang="en"><term>Anti-Bacterial Agents</term><term>Cinnamates</term><term>Flavonoids</term><term>Gentamicins</term></keywords><keywords scheme="MESH" qualifier="biosynthèse" xml:lang="fr"><term>Antibactériens</term><term>Flavonoïdes</term></keywords><keywords scheme="MESH" qualifier="chemistry" xml:lang="en"><term>Populus</term></keywords><keywords scheme="MESH" qualifier="composition chimique" xml:lang="fr"><term>Antibactériens</term><term>Cinnamates</term><term>Flavonoïdes</term><term>Populus</term></keywords><keywords scheme="MESH" qualifier="drug effects" xml:lang="en"><term>Methicillin-Resistant Staphylococcus aureus</term></keywords><keywords scheme="MESH" qualifier="effets des médicaments et des substances chimiques" xml:lang="fr"><term>Staphylococcus aureus résistant à la méticilline</term></keywords><keywords scheme="MESH" qualifier="isolation & purification" xml:lang="en"><term>Methicillin-Resistant Staphylococcus aureus</term></keywords><keywords scheme="MESH" qualifier="isolement et purification" xml:lang="fr"><term>Antibactériens</term><term>Cinnamates</term><term>Flavonoïdes</term><term>Staphylococcus aureus résistant à la méticilline</term></keywords><keywords scheme="MESH" qualifier="pharmacologie" xml:lang="fr"><term>Antibactériens</term><term>Cinnamates</term><term>Flavonoïdes</term><term>Gentamicine</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Models, Molecular</term><term>Stereoisomerism</term><term>Structure-Activity Relationship</term></keywords><keywords scheme="MESH" xml:lang="fr"><term>Modèles moléculaires</term><term>Relation structure-activité</term><term>Stéréoisomérie</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">There is nowadays an urgent need for developing novel generations of antibiotic agents due to the increased resistance of pathogenic bacteria. As a rich reservoir of structurally diverse compounds, plant species hold promise in this regard. Within this framework, we isolated a unique series of antibacterial flavonoids, named balsacones N-U, featuring multiple cinnamyl chains on the flavan skeleton. The structures of these compounds, isolated as racemates, were determined using extensive 1D and 2D NMR analysis in tandem with HRMS. Balsacones N-U along with previously isolated balsacones A-M were evaluated for their antibacterial activity against clinical isolates of methicillin resistant Staphylococcus aureus (MRSA). Several of the tested balsacones were potent anti-MRSA agents showing MIC values in the low micromolar range. Structure-activity relationships study highlighted some important parameters involved in the antibacterial activity of balsacones such as the presence of cinnamyl and cinnamoyl chains at the C-3 and C-8 positions of the flavan skeleton, respectively. These results suggest that balsacones could represent a potential novel class of naturally occurring anti-MRSA agents.</div></front></TEI><pubmed><MedlineCitation Status="MEDLINE" Owner="NLM"><PMID Version="1">27436809</PMID><DateCompleted><Year>2017</Year><Month>07</Month><Day>26</Day></DateCompleted><DateRevised><Year>2017</Year><Month>12</Month><Day>07</Day></DateRevised><Article PubModel="Print-Electronic"><Journal><ISSN IssnType="Electronic">1464-3391</ISSN><JournalIssue CitedMedium="Internet"><Volume>24</Volume><Issue>18</Issue><PubDate><Year>2016</Year><Month>09</Month><Day>15</Day></PubDate></JournalIssue><Title>Bioorganic & medicinal chemistry</Title><ISOAbbreviation>Bioorg Med Chem</ISOAbbreviation></Journal><ArticleTitle>Structure elucidation of anti-methicillin resistant Staphylococcus aureus (MRSA) flavonoids from balsam poplar buds.</ArticleTitle><Pagination><MedlinePgn>4188-4198</MedlinePgn></Pagination><ELocationID EIdType="pii" ValidYN="Y">S0968-0896(16)30501-6</ELocationID><ELocationID EIdType="doi" ValidYN="Y">10.1016/j.bmc.2016.07.009</ELocationID><Abstract><AbstractText>There is nowadays an urgent need for developing novel generations of antibiotic agents due to the increased resistance of pathogenic bacteria. As a rich reservoir of structurally diverse compounds, plant species hold promise in this regard. Within this framework, we isolated a unique series of antibacterial flavonoids, named balsacones N-U, featuring multiple cinnamyl chains on the flavan skeleton. The structures of these compounds, isolated as racemates, were determined using extensive 1D and 2D NMR analysis in tandem with HRMS. Balsacones N-U along with previously isolated balsacones A-M were evaluated for their antibacterial activity against clinical isolates of methicillin resistant Staphylococcus aureus (MRSA). Several of the tested balsacones were potent anti-MRSA agents showing MIC values in the low micromolar range. Structure-activity relationships study highlighted some important parameters involved in the antibacterial activity of balsacones such as the presence of cinnamyl and cinnamoyl chains at the C-3 and C-8 positions of the flavan skeleton, respectively. These results suggest that balsacones could represent a potential novel class of naturally occurring anti-MRSA agents.</AbstractText><CopyrightInformation>Copyright © 2016. Published by Elsevier Ltd.</CopyrightInformation></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Simard</LastName><ForeName>François</ForeName><Initials>F</Initials><AffiliationInfo><Affiliation>Laboratoire LASEVE, Département des Sciences Fondamentales, Université du Québec à Chicoutimi, 555, boul. de l'Université, Chicoutimi (Québec) G7H 2B1, Canada.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Gauthier</LastName><ForeName>Charles</ForeName><Initials>C</Initials><AffiliationInfo><Affiliation>Laboratoire LASEVE, Département des Sciences Fondamentales, Université du Québec à Chicoutimi, 555, boul. de l'Université, Chicoutimi (Québec) G7H 2B1, Canada; INRS-Institut Armand-Frappier, Université du Québec, 531 boul. des Prairies, Laval (Québec) H7V 1B7, Canada.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Legault</LastName><ForeName>Jean</ForeName><Initials>J</Initials><AffiliationInfo><Affiliation>Laboratoire LASEVE, Département des Sciences Fondamentales, Université du Québec à Chicoutimi, 555, boul. de l'Université, Chicoutimi (Québec) G7H 2B1, Canada.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Lavoie</LastName><ForeName>Serge</ForeName><Initials>S</Initials><AffiliationInfo><Affiliation>Laboratoire LASEVE, Département des Sciences Fondamentales, Université du Québec à Chicoutimi, 555, boul. de l'Université, Chicoutimi (Québec) G7H 2B1, Canada.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Mshvildadze</LastName><ForeName>Vakhtang</ForeName><Initials>V</Initials><AffiliationInfo><Affiliation>Laboratoire LASEVE, Département des Sciences Fondamentales, Université du Québec à Chicoutimi, 555, boul. de l'Université, Chicoutimi (Québec) G7H 2B1, Canada.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Pichette</LastName><ForeName>André</ForeName><Initials>A</Initials><AffiliationInfo><Affiliation>Laboratoire LASEVE, Département des Sciences Fondamentales, Université du Québec à Chicoutimi, 555, boul. de l'Université, Chicoutimi (Québec) G7H 2B1, Canada. Electronic address: andre_pichette@uqac.ca.</Affiliation></AffiliationInfo></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>2016</Year><Month>07</Month><Day>06</Day></ArticleDate></Article><MedlineJournalInfo><Country>England</Country><MedlineTA>Bioorg Med Chem</MedlineTA><NlmUniqueID>9413298</NlmUniqueID><ISSNLinking>0968-0896</ISSNLinking></MedlineJournalInfo><ChemicalList><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D000900">Anti-Bacterial Agents</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D002934">Cinnamates</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D005419">Flavonoids</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D005839">Gentamicins</NameOfSubstance></Chemical></ChemicalList><CitationSubset>IM</CitationSubset><MeshHeadingList><MeshHeading><DescriptorName UI="D000900" MajorTopicYN="N">Anti-Bacterial Agents</DescriptorName><QualifierName UI="Q000096" MajorTopicYN="N">biosynthesis</QualifierName><QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName><QualifierName UI="Q000302" MajorTopicYN="N">isolation & purification</QualifierName><QualifierName UI="Q000494" MajorTopicYN="Y">pharmacology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D002934" MajorTopicYN="N">Cinnamates</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName><QualifierName UI="Q000302" MajorTopicYN="N">isolation & purification</QualifierName><QualifierName UI="Q000494" MajorTopicYN="Y">pharmacology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D005419" MajorTopicYN="N">Flavonoids</DescriptorName><QualifierName UI="Q000096" MajorTopicYN="N">biosynthesis</QualifierName><QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName><QualifierName UI="Q000302" MajorTopicYN="N">isolation & purification</QualifierName><QualifierName UI="Q000494" MajorTopicYN="Y">pharmacology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D005839" MajorTopicYN="N">Gentamicins</DescriptorName><QualifierName UI="Q000494" MajorTopicYN="N">pharmacology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D055624" MajorTopicYN="N">Methicillin-Resistant Staphylococcus aureus</DescriptorName><QualifierName UI="Q000187" MajorTopicYN="Y">drug effects</QualifierName><QualifierName UI="Q000302" MajorTopicYN="N">isolation & purification</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D008958" MajorTopicYN="N">Models, Molecular</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D032107" MajorTopicYN="N">Populus</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="Y">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D013237" MajorTopicYN="N">Stereoisomerism</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D013329" MajorTopicYN="N">Structure-Activity Relationship</DescriptorName></MeshHeading></MeshHeadingList><KeywordList Owner="NOTNLM"><Keyword MajorTopicYN="Y">Anti-MRSA</Keyword><Keyword MajorTopicYN="Y">Antibacterial activity</Keyword><Keyword MajorTopicYN="Y">Balsacones</Keyword><Keyword MajorTopicYN="Y">Dihydrochalcones</Keyword><Keyword MajorTopicYN="Y">Flavonoids</Keyword><Keyword MajorTopicYN="Y">Structure–activity relationships</Keyword></KeywordList></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="received"><Year>2016</Year><Month>05</Month><Day>09</Day></PubMedPubDate><PubMedPubDate PubStatus="revised"><Year>2016</Year><Month>07</Month><Day>04</Day></PubMedPubDate><PubMedPubDate PubStatus="accepted"><Year>2016</Year><Month>07</Month><Day>05</Day></PubMedPubDate><PubMedPubDate PubStatus="entrez"><Year>2016</Year><Month>7</Month><Day>21</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="pubmed"><Year>2016</Year><Month>7</Month><Day>21</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="medline"><Year>2017</Year><Month>7</Month><Day>27</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate></History><PublicationStatus>ppublish</PublicationStatus><ArticleIdList><ArticleId IdType="pubmed">27436809</ArticleId><ArticleId IdType="pii">S0968-0896(16)30501-6</ArticleId><ArticleId IdType="doi">10.1016/j.bmc.2016.07.009</ArticleId></ArticleIdList></PubmedData></pubmed><affiliations><list><country><li>Canada</li></country></list><tree><country name="Canada"><noRegion><name sortKey="Simard, Francois" sort="Simard, Francois" uniqKey="Simard F" first="François" last="Simard">François Simard</name></noRegion><name sortKey="Gauthier, Charles" sort="Gauthier, Charles" uniqKey="Gauthier C" first="Charles" last="Gauthier">Charles Gauthier</name><name sortKey="Lavoie, Serge" sort="Lavoie, Serge" uniqKey="Lavoie S" first="Serge" last="Lavoie">Serge Lavoie</name><name sortKey="Legault, Jean" sort="Legault, Jean" uniqKey="Legault J" first="Jean" last="Legault">Jean Legault</name><name sortKey="Mshvildadze, Vakhtang" sort="Mshvildadze, Vakhtang" uniqKey="Mshvildadze V" first="Vakhtang" last="Mshvildadze">Vakhtang Mshvildadze</name><name sortKey="Pichette, Andre" sort="Pichette, Andre" uniqKey="Pichette A" first="André" last="Pichette">André Pichette</name></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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