The absolute configuration of salicortin, HCH-salicortin and tremulacin from Populus trichocarpa × deltoides Beaupré.
Identifieur interne : 001B13 ( Main/Exploration ); précédent : 001B12; suivant : 001B14The absolute configuration of salicortin, HCH-salicortin and tremulacin from Populus trichocarpa × deltoides Beaupré.
Auteurs : Felix Feistel [Allemagne] ; Christian Paetz [Allemagne] ; Sybille Lorenz [Allemagne] ; Bernd Schneider [Allemagne]Source :
- Molecules (Basel, Switzerland) [ 1420-3049 ] ; 2015.
Descripteurs français
- KwdFr :
- Acides cyclohexanecarboxyliques (composition chimique), Dichroïsme circulaire (MeSH), Feuilles de plante (composition chimique), Glucosides (composition chimique), Glucosides (isolement et purification), Populus (composition chimique), Salicaceae (classification), Salicaceae (composition chimique), Spectrométrie de masse (MeSH), Structure moléculaire (MeSH).
- MESH :
- composition chimique : Acides cyclohexanecarboxyliques, Feuilles de plante, Glucosides, Populus, Salicaceae.
- isolement et purification : Glucosides.
- Dichroïsme circulaire, Spectrométrie de masse, Structure moléculaire.
English descriptors
- KwdEn :
- MESH :
- chemical , chemistry : Cyclohexanecarboxylic Acids, Glucosides.
- chemical , isolation & purification : Glucosides.
- chemistry : Plant Leaves, Populus, Salicaceae.
- classification : Salicaceae.
- Circular Dichroism, Mass Spectrometry, Molecular Structure.
Abstract
The absolute configuration of salicortin, HCH-salicortin and tremulacin, isolated from leaves of Populus trichocarpa × deltoides Beaupré, was determined by comparing spectroscopic data of these compounds with those of idescarpin, isolated from leaves of Idesia polycarpa. All compounds were characterized by nuclear magnetic resonance spectroscopy, high-resolution mass spectrometry, and circular dichroism spectroscopy. It was found that the hydroxy cyclohexenonoyl (HCH) moiety in all compounds is (S)-configured. In addition, it was shown that leaves of Idesia polycarpa contain high amounts of (-)-idescarpin (1.1%, based on dry weight).
DOI: 10.3390/molecules20045566
PubMed: 25830788
PubMed Central: PMC6272461
Affiliations:
Links toward previous steps (curation, corpus...)
Le document en format XML
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07745</wicri:noRegion></affiliation></author><author><name sortKey="Paetz, Christian" sort="Paetz, Christian" uniqKey="Paetz C" first="Christian" last="Paetz">Christian Paetz</name><affiliation wicri:level="1"><nlm:affiliation>Max Planck Institute for Chemical Ecology, Hans-Knöll-Straße 8, Jena 07745, Germany. cpaetz@ice.mpg.de.</nlm:affiliation><country xml:lang="fr">Allemagne</country><wicri:regionArea>Max Planck Institute for Chemical Ecology, Hans-Knöll-Straße 8, Jena 07745</wicri:regionArea><wicri:noRegion>07745</wicri:noRegion><wicri:noRegion>07745</wicri:noRegion><wicri:noRegion>Jena 07745</wicri:noRegion></affiliation></author><author><name sortKey="Lorenz, Sybille" sort="Lorenz, Sybille" uniqKey="Lorenz S" first="Sybille" last="Lorenz">Sybille Lorenz</name><affiliation wicri:level="1"><nlm:affiliation>Max Planck Institute for Chemical Ecology, Hans-Knöll-Straße 8, Jena 07745, Germany. lorenz@ice.mpg.de.</nlm:affiliation><country 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type="eISSN">1420-3049</idno><imprint><date when="2015" type="published">2015</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Circular Dichroism (MeSH)</term><term>Cyclohexanecarboxylic Acids (chemistry)</term><term>Glucosides (chemistry)</term><term>Glucosides (isolation & purification)</term><term>Mass Spectrometry (MeSH)</term><term>Molecular Structure (MeSH)</term><term>Plant Leaves (chemistry)</term><term>Populus (chemistry)</term><term>Salicaceae (chemistry)</term><term>Salicaceae (classification)</term></keywords><keywords scheme="KwdFr" xml:lang="fr"><term>Acides cyclohexanecarboxyliques (composition chimique)</term><term>Dichroïsme circulaire (MeSH)</term><term>Feuilles de plante (composition chimique)</term><term>Glucosides (composition chimique)</term><term>Glucosides (isolement et purification)</term><term>Populus (composition chimique)</term><term>Salicaceae (classification)</term><term>Salicaceae (composition chimique)</term><term>Spectrométrie de masse (MeSH)</term><term>Structure moléculaire (MeSH)</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Cyclohexanecarboxylic Acids</term><term>Glucosides</term></keywords><keywords scheme="MESH" type="chemical" qualifier="isolation & purification" xml:lang="en"><term>Glucosides</term></keywords><keywords scheme="MESH" qualifier="chemistry" xml:lang="en"><term>Plant Leaves</term><term>Populus</term><term>Salicaceae</term></keywords><keywords scheme="MESH" qualifier="classification" xml:lang="en"><term>Salicaceae</term></keywords><keywords scheme="MESH" qualifier="composition chimique" xml:lang="fr"><term>Acides cyclohexanecarboxyliques</term><term>Feuilles de plante</term><term>Glucosides</term><term>Populus</term><term>Salicaceae</term></keywords><keywords scheme="MESH" qualifier="isolement et purification" xml:lang="fr"><term>Glucosides</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Circular Dichroism</term><term>Mass Spectrometry</term><term>Molecular Structure</term></keywords><keywords scheme="MESH" xml:lang="fr"><term>Dichroïsme circulaire</term><term>Spectrométrie de masse</term><term>Structure moléculaire</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">The absolute configuration of salicortin, HCH-salicortin and tremulacin, isolated from leaves of Populus trichocarpa × deltoides Beaupré, was determined by comparing spectroscopic data of these compounds with those of idescarpin, isolated from leaves of Idesia polycarpa. All compounds were characterized by nuclear magnetic resonance spectroscopy, high-resolution mass spectrometry, and circular dichroism spectroscopy. It was found that the hydroxy cyclohexenonoyl (HCH) moiety in all compounds is (S)-configured. In addition, it was shown that leaves of Idesia polycarpa contain high amounts of (-)-idescarpin (1.1%, based on dry weight). </div></front></TEI><pubmed><MedlineCitation Status="MEDLINE" Owner="NLM"><PMID Version="1">25830788</PMID><DateCompleted><Year>2016</Year><Month>01</Month><Day>15</Day></DateCompleted><DateRevised><Year>2018</Year><Month>12</Month><Day>07</Day></DateRevised><Article PubModel="Electronic"><Journal><ISSN IssnType="Electronic">1420-3049</ISSN><JournalIssue CitedMedium="Internet"><Volume>20</Volume><Issue>4</Issue><PubDate><Year>2015</Year><Month>Mar</Month><Day>30</Day></PubDate></JournalIssue><Title>Molecules (Basel, Switzerland)</Title><ISOAbbreviation>Molecules</ISOAbbreviation></Journal><ArticleTitle>The absolute configuration of salicortin, HCH-salicortin and tremulacin from Populus trichocarpa × deltoides Beaupré.</ArticleTitle><Pagination><MedlinePgn>5566-73</MedlinePgn></Pagination><ELocationID EIdType="doi" ValidYN="Y">10.3390/molecules20045566</ELocationID><Abstract><AbstractText>The absolute configuration of salicortin, HCH-salicortin and tremulacin, isolated from leaves of Populus trichocarpa × deltoides Beaupré, was determined by comparing spectroscopic data of these compounds with those of idescarpin, isolated from leaves of Idesia polycarpa. All compounds were characterized by nuclear magnetic resonance spectroscopy, high-resolution mass spectrometry, and circular dichroism spectroscopy. It was found that the hydroxy cyclohexenonoyl (HCH) moiety in all compounds is (S)-configured. In addition, it was shown that leaves of Idesia polycarpa contain high amounts of (-)-idescarpin (1.1%, based on dry weight). </AbstractText></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Feistel</LastName><ForeName>Felix</ForeName><Initials>F</Initials><AffiliationInfo><Affiliation>Max Planck Institute for Chemical Ecology, Hans-Knöll-Straße 8, Jena 07745, Germany. ffeistel@ice.mpg.de.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Paetz</LastName><ForeName>Christian</ForeName><Initials>C</Initials><AffiliationInfo><Affiliation>Max Planck Institute for Chemical Ecology, Hans-Knöll-Straße 8, Jena 07745, Germany. cpaetz@ice.mpg.de.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Lorenz</LastName><ForeName>Sybille</ForeName><Initials>S</Initials><AffiliationInfo><Affiliation>Max Planck Institute for Chemical Ecology, Hans-Knöll-Straße 8, Jena 07745, Germany. lorenz@ice.mpg.de.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Schneider</LastName><ForeName>Bernd</ForeName><Initials>B</Initials><AffiliationInfo><Affiliation>Max Planck Institute for Chemical Ecology, Hans-Knöll-Straße 8, Jena 07745, Germany. schneider@ice.mpg.de.</Affiliation></AffiliationInfo></Author></AuthorList><Language>eng</Language><PublicationTypeList><PublicationType UI="D003160">Comparative Study</PublicationType><PublicationType UI="D016428">Journal Article</PublicationType></PublicationTypeList><ArticleDate DateType="Electronic"><Year>2015</Year><Month>03</Month><Day>30</Day></ArticleDate></Article><MedlineJournalInfo><Country>Switzerland</Country><MedlineTA>Molecules</MedlineTA><NlmUniqueID>100964009</NlmUniqueID><ISSNLinking>1420-3049</ISSNLinking></MedlineJournalInfo><ChemicalList><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D003509">Cyclohexanecarboxylic Acids</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D005960">Glucosides</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="C584753">idescarpin</NameOfSubstance></Chemical><Chemical><RegistryNumber>29836-40-6</RegistryNumber><NameOfSubstance UI="C095421">tremulacin</NameOfSubstance></Chemical><Chemical><RegistryNumber>YI29948E0Q</RegistryNumber><NameOfSubstance UI="C113068">salicortin</NameOfSubstance></Chemical></ChemicalList><CitationSubset>IM</CitationSubset><MeshHeadingList><MeshHeading><DescriptorName UI="D002942" MajorTopicYN="N">Circular Dichroism</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D003509" MajorTopicYN="N">Cyclohexanecarboxylic Acids</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="Y">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D005960" MajorTopicYN="N">Glucosides</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="Y">chemistry</QualifierName><QualifierName UI="Q000302" MajorTopicYN="N">isolation & purification</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D013058" MajorTopicYN="N">Mass Spectrometry</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D015394" MajorTopicYN="N">Molecular Structure</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D018515" MajorTopicYN="N">Plant Leaves</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D032107" MajorTopicYN="N">Populus</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D031308" MajorTopicYN="N">Salicaceae</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="Y">chemistry</QualifierName><QualifierName UI="Q000145" MajorTopicYN="N">classification</QualifierName></MeshHeading></MeshHeadingList></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="received"><Year>2015</Year><Month>02</Month><Day>03</Day></PubMedPubDate><PubMedPubDate PubStatus="revised"><Year>2015</Year><Month>03</Month><Day>20</Day></PubMedPubDate><PubMedPubDate PubStatus="accepted"><Year>2015</Year><Month>03</Month><Day>26</Day></PubMedPubDate><PubMedPubDate PubStatus="entrez"><Year>2015</Year><Month>4</Month><Day>2</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="pubmed"><Year>2015</Year><Month>4</Month><Day>2</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="medline"><Year>2016</Year><Month>1</Month><Day>16</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate></History><PublicationStatus>epublish</PublicationStatus><ArticleIdList><ArticleId IdType="pubmed">25830788</ArticleId><ArticleId IdType="pii">molecules20045566</ArticleId><ArticleId IdType="doi">10.3390/molecules20045566</ArticleId><ArticleId IdType="pmc">PMC6272461</ArticleId></ArticleIdList><ReferenceList><Reference><Citation>J Nat Prod. 2006 Sep;69(9):1300-4</Citation><ArticleIdList><ArticleId IdType="pubmed">16989523</ArticleId></ArticleIdList></Reference><Reference><Citation>J Chem Ecol. 2010 Mar;36(3):286-97</Citation><ArticleIdList><ArticleId IdType="pubmed">20177744</ArticleId></ArticleIdList></Reference><Reference><Citation>Physiol Plant. 2001 Aug;112(4):552-558</Citation><ArticleIdList><ArticleId IdType="pubmed">11473716</ArticleId></ArticleIdList></Reference><Reference><Citation>Phytochemistry. 2011 Sep;72(13):1497-509</Citation><ArticleIdList><ArticleId IdType="pubmed">21376356</ArticleId></ArticleIdList></Reference><Reference><Citation>J Chem Ecol. 1989 Sep;15(9):2335-46</Citation><ArticleIdList><ArticleId IdType="pubmed">24272421</ArticleId></ArticleIdList></Reference><Reference><Citation>Biol Rev Camb Philos Soc. 2014 Aug;89(3):531-51</Citation><ArticleIdList><ArticleId IdType="pubmed">25165798</ArticleId></ArticleIdList></Reference><Reference><Citation>Planta Med. 2007 Feb;73(2):167-9</Citation><ArticleIdList><ArticleId IdType="pubmed">17128390</ArticleId></ArticleIdList></Reference><Reference><Citation>Molecules. 2013 Aug 30;18(9):10484-96</Citation><ArticleIdList><ArticleId IdType="pubmed">23999723</ArticleId></ArticleIdList></Reference><Reference><Citation>Bioorg Med Chem Lett. 2013 Jun 1;23(11):3170-4</Citation><ArticleIdList><ArticleId IdType="pubmed">23628332</ArticleId></ArticleIdList></Reference><Reference><Citation>New Phytol. 2014 Jul;203(2):607-19</Citation><ArticleIdList><ArticleId IdType="pubmed">24739022</ArticleId></ArticleIdList></Reference><Reference><Citation>Planta Med. 2010 Oct;76(14):1519-24</Citation><ArticleIdList><ArticleId IdType="pubmed">20301058</ArticleId></ArticleIdList></Reference><Reference><Citation>J Nat Prod. 2010 Jun 25;73(6):1126-32</Citation><ArticleIdList><ArticleId IdType="pubmed">20509666</ArticleId></ArticleIdList></Reference></ReferenceList></PubmedData></pubmed><affiliations><list><country><li>Allemagne</li></country></list><tree><country name="Allemagne"><noRegion><name sortKey="Feistel, Felix" sort="Feistel, Felix" uniqKey="Feistel F" first="Felix" last="Feistel">Felix Feistel</name></noRegion><name sortKey="Lorenz, Sybille" sort="Lorenz, Sybille" uniqKey="Lorenz S" first="Sybille" last="Lorenz">Sybille Lorenz</name><name sortKey="Paetz, Christian" sort="Paetz, Christian" uniqKey="Paetz C" first="Christian" last="Paetz">Christian Paetz</name><name sortKey="Schneider, Bernd" sort="Schneider, Bernd" uniqKey="Schneider B" first="Bernd" last="Schneider">Bernd Schneider</name></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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