Antibacterial Balsacones J-M, Hydroxycinnamoylated Dihydrochalcones from Populus balsamifera Buds.
Identifieur interne : 001F00 ( Main/Exploration ); précédent : 001E99; suivant : 001F01Antibacterial Balsacones J-M, Hydroxycinnamoylated Dihydrochalcones from Populus balsamifera Buds.
Auteurs : François Simard ; Charles Gauthier [France] ; Éric Chiasson ; Serge Lavoie ; Vakhtang Mshvildadze ; Jean Legault ; André PichetteSource :
- Journal of natural products [ 1520-6025 ] ; 2015.
Descripteurs français
- KwdFr :
- Antibactériens (composition chimique), Antibactériens (isolement et purification), Antibactériens (pharmacologie), Canada (MeSH), Chalcones (composition chimique), Chalcones (isolement et purification), Chalcones (pharmacologie), Chromatographie en phase liquide à haute performance (MeSH), Concentration inhibitrice 50 (MeSH), Conformation moléculaire (MeSH), Cristallographie aux rayons X (MeSH), Fibroblastes (effets des médicaments et des substances chimiques), Humains (MeSH), Populus (composition chimique), Résonance magnétique nucléaire biomoléculaire (MeSH), Staphylococcus aureus (effets des médicaments et des substances chimiques), Structure moléculaire (MeSH), Stéréoisomérie (MeSH), Tests de criblage d'agents antitumoraux (MeSH).
- MESH :
- composition chimique : Antibactériens, Chalcones, Populus.
- effets des médicaments et des substances chimiques : Fibroblastes, Staphylococcus aureus.
- isolement et purification : Antibactériens, Chalcones.
- pharmacologie : Antibactériens, Chalcones.
- Canada, Chromatographie en phase liquide à haute performance, Concentration inhibitrice 50, Conformation moléculaire, Cristallographie aux rayons X, Humains, Résonance magnétique nucléaire biomoléculaire, Structure moléculaire, Stéréoisomérie, Tests de criblage d'agents antitumoraux.
- Wicri :
- geographic : Canada.
English descriptors
- KwdEn :
- Anti-Bacterial Agents (chemistry), Anti-Bacterial Agents (isolation & purification), Anti-Bacterial Agents (pharmacology), Canada (MeSH), Chalcones (chemistry), Chalcones (isolation & purification), Chalcones (pharmacology), Chromatography, High Pressure Liquid (MeSH), Crystallography, X-Ray (MeSH), Drug Screening Assays, Antitumor (MeSH), Fibroblasts (drug effects), Humans (MeSH), Inhibitory Concentration 50 (MeSH), Molecular Conformation (MeSH), Molecular Structure (MeSH), Nuclear Magnetic Resonance, Biomolecular (MeSH), Populus (chemistry), Staphylococcus aureus (drug effects), Stereoisomerism (MeSH).
- MESH :
- chemical , chemistry : Anti-Bacterial Agents, Chalcones.
- chemical , isolation & purification : Anti-Bacterial Agents, Chalcones.
- chemical , pharmacology : Anti-Bacterial Agents, Chalcones.
- geographic : Canada.
- chemistry : Populus.
- drug effects : Fibroblasts, Staphylococcus aureus.
- Chromatography, High Pressure Liquid, Crystallography, X-Ray, Drug Screening Assays, Antitumor, Humans, Inhibitory Concentration 50, Molecular Conformation, Molecular Structure, Nuclear Magnetic Resonance, Biomolecular, Stereoisomerism.
Abstract
A phytochemical investigation of buds from the hardwood tree Populus balsamifera led to the isolation of six new cinnamoylated dihydrochalcones as pairs of racemates and one as a racemic mixture along with the known compound iryantherin-D (2), the absolute configuration of which was determined for the first time. The structures of balsacones J (1), K (3), L (4), and M (5) were elucidated on the basis of spectroscopic data (1D and 2D NMR, IR, and MS). Chiral HPLC separations were carried out, and the absolute configuration of the isolated enantiomers unambiguously established via X-ray diffraction analyses and electron circular dichroism spectroscopic data. Each of the purified enantiomers exhibited potent in vitro antibacterial activity against Staphylococcus aureus with IC50 values ranging from 0.61 to 6 μM.
DOI: 10.1021/acs.jnatprod.5b00155
PubMed: 25927817
Affiliations:
Links toward previous steps (curation, corpus...)
Le document en format XML
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first="André" last="Pichette">André Pichette</name><affiliation><nlm:affiliation>†Chaire de Recherche sur les Agents Anticancéreux d'Origine Naturelle, Laboratoire LASEVE, Département des Sciences Fondamentales, Université du Québec à Chicoutimi, 555 Boulevard de l'Université, Chicoutimi, Québec, Canada, G7H 2B1.</nlm:affiliation><wicri:noCountry code="subField">G7H 2B1</wicri:noCountry></affiliation></author></analytic><series><title level="j">Journal of natural products</title><idno type="eISSN">1520-6025</idno><imprint><date when="2015" type="published">2015</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Anti-Bacterial Agents (chemistry)</term><term>Anti-Bacterial Agents (isolation & purification)</term><term>Anti-Bacterial Agents (pharmacology)</term><term>Canada (MeSH)</term><term>Chalcones (chemistry)</term><term>Chalcones (isolation & purification)</term><term>Chalcones (pharmacology)</term><term>Chromatography, High Pressure Liquid (MeSH)</term><term>Crystallography, X-Ray (MeSH)</term><term>Drug Screening Assays, Antitumor (MeSH)</term><term>Fibroblasts (drug effects)</term><term>Humans (MeSH)</term><term>Inhibitory Concentration 50 (MeSH)</term><term>Molecular Conformation (MeSH)</term><term>Molecular Structure (MeSH)</term><term>Nuclear Magnetic Resonance, Biomolecular (MeSH)</term><term>Populus (chemistry)</term><term>Staphylococcus aureus (drug effects)</term><term>Stereoisomerism (MeSH)</term></keywords><keywords scheme="KwdFr" xml:lang="fr"><term>Antibactériens (composition chimique)</term><term>Antibactériens (isolement et purification)</term><term>Antibactériens (pharmacologie)</term><term>Canada (MeSH)</term><term>Chalcones (composition chimique)</term><term>Chalcones (isolement et purification)</term><term>Chalcones (pharmacologie)</term><term>Chromatographie en phase liquide à haute performance (MeSH)</term><term>Concentration inhibitrice 50 (MeSH)</term><term>Conformation moléculaire (MeSH)</term><term>Cristallographie aux rayons X (MeSH)</term><term>Fibroblastes (effets des médicaments et des substances chimiques)</term><term>Humains (MeSH)</term><term>Populus (composition chimique)</term><term>Résonance magnétique nucléaire biomoléculaire (MeSH)</term><term>Staphylococcus aureus (effets des médicaments et des substances chimiques)</term><term>Structure moléculaire (MeSH)</term><term>Stéréoisomérie (MeSH)</term><term>Tests de criblage d'agents antitumoraux (MeSH)</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Anti-Bacterial Agents</term><term>Chalcones</term></keywords><keywords scheme="MESH" type="chemical" qualifier="isolation & purification" xml:lang="en"><term>Anti-Bacterial Agents</term><term>Chalcones</term></keywords><keywords scheme="MESH" type="chemical" qualifier="pharmacology" xml:lang="en"><term>Anti-Bacterial Agents</term><term>Chalcones</term></keywords><keywords scheme="MESH" type="geographic" xml:lang="en"><term>Canada</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>Chalcones</term><term>Populus</term></keywords><keywords scheme="MESH" qualifier="drug effects" xml:lang="en"><term>Fibroblasts</term><term>Staphylococcus aureus</term></keywords><keywords scheme="MESH" qualifier="effets des médicaments et des substances chimiques" xml:lang="fr"><term>Fibroblastes</term><term>Staphylococcus aureus</term></keywords><keywords scheme="MESH" qualifier="isolement et purification" xml:lang="fr"><term>Antibactériens</term><term>Chalcones</term></keywords><keywords scheme="MESH" qualifier="pharmacologie" xml:lang="fr"><term>Antibactériens</term><term>Chalcones</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Chromatography, High Pressure Liquid</term><term>Crystallography, X-Ray</term><term>Drug Screening Assays, Antitumor</term><term>Humans</term><term>Inhibitory Concentration 50</term><term>Molecular Conformation</term><term>Molecular Structure</term><term>Nuclear Magnetic Resonance, Biomolecular</term><term>Stereoisomerism</term></keywords><keywords scheme="MESH" xml:lang="fr"><term>Canada</term><term>Chromatographie en phase liquide à haute performance</term><term>Concentration inhibitrice 50</term><term>Conformation moléculaire</term><term>Cristallographie aux rayons X</term><term>Humains</term><term>Résonance magnétique nucléaire biomoléculaire</term><term>Structure moléculaire</term><term>Stéréoisomérie</term><term>Tests de criblage d'agents antitumoraux</term></keywords><keywords scheme="Wicri" type="geographic" xml:lang="fr"><term>Canada</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">A phytochemical investigation of buds from the hardwood tree Populus balsamifera led to the isolation of six new cinnamoylated dihydrochalcones as pairs of racemates and one as a racemic mixture along with the known compound iryantherin-D (2), the absolute configuration of which was determined for the first time. The structures of balsacones J (1), K (3), L (4), and M (5) were elucidated on the basis of spectroscopic data (1D and 2D NMR, IR, and MS). Chiral HPLC separations were carried out, and the absolute configuration of the isolated enantiomers unambiguously established via X-ray diffraction analyses and electron circular dichroism spectroscopic data. Each of the purified enantiomers exhibited potent in vitro antibacterial activity against Staphylococcus aureus with IC50 values ranging from 0.61 to 6 μM. </div></front></TEI><pubmed><MedlineCitation Status="MEDLINE" Owner="NLM"><PMID Version="1">25927817</PMID><DateCompleted><Year>2015</Year><Month>08</Month><Day>10</Day></DateCompleted><DateRevised><Year>2015</Year><Month>11</Month><Day>19</Day></DateRevised><Article PubModel="Print-Electronic"><Journal><ISSN IssnType="Electronic">1520-6025</ISSN><JournalIssue CitedMedium="Internet"><Volume>78</Volume><Issue>5</Issue><PubDate><Year>2015</Year><Month>May</Month><Day>22</Day></PubDate></JournalIssue><Title>Journal of natural products</Title><ISOAbbreviation>J Nat Prod</ISOAbbreviation></Journal><ArticleTitle>Antibacterial Balsacones J-M, Hydroxycinnamoylated Dihydrochalcones from Populus balsamifera Buds.</ArticleTitle><Pagination><MedlinePgn>1147-53</MedlinePgn></Pagination><ELocationID EIdType="doi" ValidYN="Y">10.1021/acs.jnatprod.5b00155</ELocationID><Abstract><AbstractText>A phytochemical investigation of buds from the hardwood tree Populus balsamifera led to the isolation of six new cinnamoylated dihydrochalcones as pairs of racemates and one as a racemic mixture along with the known compound iryantherin-D (2), the absolute configuration of which was determined for the first time. The structures of balsacones J (1), K (3), L (4), and M (5) were elucidated on the basis of spectroscopic data (1D and 2D NMR, IR, and MS). Chiral HPLC separations were carried out, and the absolute configuration of the isolated enantiomers unambiguously established via X-ray diffraction analyses and electron circular dichroism spectroscopic data. Each of the purified enantiomers exhibited potent in vitro antibacterial activity against Staphylococcus aureus with IC50 values ranging from 0.61 to 6 μM. </AbstractText></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Simard</LastName><ForeName>François</ForeName><Initials>F</Initials><AffiliationInfo><Affiliation>†Chaire de Recherche sur les Agents Anticancéreux d'Origine Naturelle, Laboratoire LASEVE, Département des Sciences Fondamentales, Université du Québec à Chicoutimi, 555 Boulevard de l'Université, Chicoutimi, Québec, Canada, G7H 2B1.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Gauthier</LastName><ForeName>Charles</ForeName><Initials>C</Initials><AffiliationInfo><Affiliation>†Chaire de Recherche sur les Agents Anticancéreux d'Origine Naturelle, Laboratoire LASEVE, Département des Sciences Fondamentales, Université du Québec à Chicoutimi, 555 Boulevard de l'Université, Chicoutimi, Québec, Canada, G7H 2B1.</Affiliation></AffiliationInfo><AffiliationInfo><Affiliation>‡Institut de Chimie IC2MP, CNRS-UMR 7285, Équipe Synthèse Organique, Université de Poitiers, 4 Rue Michel Brunet, 86073 Poitiers Cedex-9, France.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Chiasson</LastName><ForeName>Éric</ForeName><Initials>É</Initials><AffiliationInfo><Affiliation>†Chaire de Recherche sur les Agents Anticancéreux d'Origine Naturelle, Laboratoire LASEVE, Département des Sciences Fondamentales, Université du Québec à Chicoutimi, 555 Boulevard de l'Université, Chicoutimi, Québec, Canada, G7H 2B1.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Lavoie</LastName><ForeName>Serge</ForeName><Initials>S</Initials><AffiliationInfo><Affiliation>†Chaire de Recherche sur les Agents Anticancéreux d'Origine Naturelle, Laboratoire LASEVE, Département des Sciences Fondamentales, Université du Québec à Chicoutimi, 555 Boulevard de l'Université, Chicoutimi, Québec, Canada, G7H 2B1.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Mshvildadze</LastName><ForeName>Vakhtang</ForeName><Initials>V</Initials><AffiliationInfo><Affiliation>†Chaire de Recherche sur les Agents Anticancéreux d'Origine Naturelle, Laboratoire LASEVE, Département des Sciences Fondamentales, Université du Québec à Chicoutimi, 555 Boulevard de l'Université, Chicoutimi, Québec, Canada, G7H 2B1.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Legault</LastName><ForeName>Jean</ForeName><Initials>J</Initials><AffiliationInfo><Affiliation>†Chaire de Recherche sur les Agents Anticancéreux d'Origine Naturelle, Laboratoire LASEVE, Département des Sciences Fondamentales, Université du Québec à Chicoutimi, 555 Boulevard de l'Université, Chicoutimi, Québec, Canada, G7H 2B1.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Pichette</LastName><ForeName>André</ForeName><Initials>A</Initials><AffiliationInfo><Affiliation>†Chaire de Recherche sur les Agents Anticancéreux d'Origine Naturelle, Laboratoire LASEVE, Département des Sciences Fondamentales, Université du Québec à Chicoutimi, 555 Boulevard de l'Université, Chicoutimi, Québec, Canada, G7H 2B1.</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>2015</Year><Month>04</Month><Day>30</Day></ArticleDate></Article><MedlineJournalInfo><Country>United States</Country><MedlineTA>J Nat Prod</MedlineTA><NlmUniqueID>7906882</NlmUniqueID><ISSNLinking>0163-3864</ISSNLinking></MedlineJournalInfo><ChemicalList><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D000900">Anti-Bacterial Agents</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D047188">Chalcones</NameOfSubstance></Chemical><Chemical><RegistryNumber>H5W525SX7Q</RegistryNumber><NameOfSubstance UI="C015812">dihydrochalcone</NameOfSubstance></Chemical></ChemicalList><CitationSubset>IM</CitationSubset><MeshHeadingList><MeshHeading><DescriptorName UI="D000900" MajorTopicYN="N">Anti-Bacterial Agents</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName><QualifierName UI="Q000302" MajorTopicYN="Y">isolation & purification</QualifierName><QualifierName UI="Q000494" MajorTopicYN="Y">pharmacology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D002170" MajorTopicYN="N" Type="Geographic">Canada</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D047188" MajorTopicYN="N">Chalcones</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName><QualifierName UI="Q000302" MajorTopicYN="Y">isolation & purification</QualifierName><QualifierName UI="Q000494" MajorTopicYN="Y">pharmacology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D002851" MajorTopicYN="N">Chromatography, High Pressure Liquid</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D018360" MajorTopicYN="N">Crystallography, X-Ray</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D004354" MajorTopicYN="N">Drug Screening Assays, Antitumor</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D005347" MajorTopicYN="N">Fibroblasts</DescriptorName><QualifierName UI="Q000187" MajorTopicYN="N">drug effects</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D006801" MajorTopicYN="N">Humans</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D020128" MajorTopicYN="N">Inhibitory Concentration 50</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D008968" MajorTopicYN="N">Molecular Conformation</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D015394" MajorTopicYN="N">Molecular Structure</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D019906" MajorTopicYN="N">Nuclear Magnetic Resonance, Biomolecular</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D032107" MajorTopicYN="N">Populus</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="Y">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D013211" MajorTopicYN="N">Staphylococcus aureus</DescriptorName><QualifierName UI="Q000187" MajorTopicYN="N">drug effects</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D013237" MajorTopicYN="N">Stereoisomerism</DescriptorName></MeshHeading></MeshHeadingList></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="entrez"><Year>2015</Year><Month>5</Month><Day>1</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="pubmed"><Year>2015</Year><Month>5</Month><Day>1</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="medline"><Year>2015</Year><Month>8</Month><Day>11</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate></History><PublicationStatus>ppublish</PublicationStatus><ArticleIdList><ArticleId IdType="pubmed">25927817</ArticleId><ArticleId IdType="doi">10.1021/acs.jnatprod.5b00155</ArticleId></ArticleIdList></PubmedData></pubmed><affiliations><list><country><li>France</li></country><region><li>Nouvelle-Aquitaine</li><li>Poitou-Charentes</li></region><settlement><li>Poitiers</li></settlement><orgName><li>Université de Poitiers</li></orgName></list><tree><noCountry><name sortKey="Chiasson, Eric" sort="Chiasson, Eric" uniqKey="Chiasson E" first="Éric" last="Chiasson">Éric Chiasson</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><name sortKey="Simard, Francois" sort="Simard, Francois" uniqKey="Simard F" first="François" last="Simard">François Simard</name></noCountry><country name="France"><region name="Nouvelle-Aquitaine"><name sortKey="Gauthier, Charles" sort="Gauthier, Charles" uniqKey="Gauthier C" first="Charles" last="Gauthier">Charles Gauthier</name></region></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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