Sulfated flavanones and dihydroflavonols from willow.
Identifieur interne : 000064 ( Main/Exploration ); précédent : 000063; suivant : 000065Sulfated flavanones and dihydroflavonols from willow.
Auteurs : Clarice Noleto-Dias [Royaume-Uni] ; Claudia Harflett [Royaume-Uni] ; Michael H. Beale [Royaume-Uni] ; Jane L. Ward [Royaume-Uni]Source :
- Phytochemistry letters [ 1874-3900 ] ; 2020.
Abstract
Phytochemical profiling of a hybrid species of willow, Salix × alberti L. (S. integra Thunb. × Salix suchowensis W.C. Cheng ex G.Zhu) revealed four sulfated flavonoids, which were then isolated from young stem tissue. The structures of dihydroflavonols (flavanonols) taxifolin-7-sulfate (1) and dihydrokaempferol-7-sulfate (2) and flavanones, eridictyol-7-sulfate (3) and naringenin-7-sulfate (4) were elucidated through NMR spectroscopy and high-resolution mass spectrometry. The identified sulfated flavanones and dihydroflavonols have not been previously seen in plants, but the former have been partially characterised as metabolites in mammalian metabolism of dietary flavonoids. In addition to providing full spectroscopic characterisation of these metabolites for the first time, we also compared the in vitro antioxidant properties, via the DPPH radical scavenging assay, of the parent and sulfated flavanones, which showed that 7-sulfation of taxifolin and eriodictyol attenuates but does not remove anti-oxidant activity.
DOI: 10.1016/j.phytol.2019.11.008
PubMed: 32025274
PubMed Central: PMC6988443
Affiliations:
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Beale</name><affiliation wicri:level="1"><nlm:affiliation>Department of Computational and Analytical Sciences, Rothamsted Research, West Common, Harpenden, Hertfordshire, AL5 2JQ, UK.</nlm:affiliation><country xml:lang="fr">Royaume-Uni</country><wicri:regionArea>Department of Computational and Analytical Sciences, Rothamsted Research, West Common, Harpenden, Hertfordshire, AL5 2JQ</wicri:regionArea><wicri:noRegion>AL5 2JQ</wicri:noRegion></affiliation></author><author><name sortKey="Ward, Jane L" sort="Ward, Jane L" uniqKey="Ward J" first="Jane L" last="Ward">Jane L. 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Beale</name><affiliation wicri:level="1"><nlm:affiliation>Department of Computational and Analytical Sciences, Rothamsted Research, West Common, Harpenden, Hertfordshire, AL5 2JQ, UK.</nlm:affiliation><country xml:lang="fr">Royaume-Uni</country><wicri:regionArea>Department of Computational and Analytical Sciences, Rothamsted Research, West Common, Harpenden, Hertfordshire, AL5 2JQ</wicri:regionArea><wicri:noRegion>AL5 2JQ</wicri:noRegion></affiliation></author><author><name sortKey="Ward, Jane L" sort="Ward, Jane L" uniqKey="Ward J" first="Jane L" last="Ward">Jane L. Ward</name><affiliation wicri:level="1"><nlm:affiliation>Department of Computational and Analytical Sciences, Rothamsted Research, West Common, Harpenden, Hertfordshire, AL5 2JQ, UK.</nlm:affiliation><country xml:lang="fr">Royaume-Uni</country><wicri:regionArea>Department of Computational and Analytical Sciences, Rothamsted Research, West Common, Harpenden, Hertfordshire, AL5 2JQ</wicri:regionArea><wicri:noRegion>AL5 2JQ</wicri:noRegion></affiliation></author></analytic><series><title level="j">Phytochemistry letters</title><idno type="ISSN">1874-3900</idno><imprint><date when="2020" type="published">2020</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">Phytochemical profiling of a hybrid species of willow, <i>Salix</i> × <i>alberti</i> L. (<i>S. integra</i> Thunb. × <i>Salix suchowensis</i> W.C. Cheng ex G.Zhu) revealed four sulfated flavonoids, which were then isolated from young stem tissue. The structures of dihydroflavonols (flavanonols) taxifolin-7-sulfate <b>(1)</b> and dihydrokaempferol-7-sulfate <b>(2)</b> and flavanones, eridictyol-7-sulfate <b>(3)</b> and naringenin-7-sulfate <b>(4)</b> were elucidated through NMR spectroscopy and high-resolution mass spectrometry. The identified sulfated flavanones and dihydroflavonols have not been previously seen in plants, but the former have been partially characterised as metabolites in mammalian metabolism of dietary flavonoids. In addition to providing full spectroscopic characterisation of these metabolites for the first time, we also compared the <i>in vitro</i> antioxidant properties, <i>via</i> the DPPH radical scavenging assay, of the parent and sulfated flavanones, which showed that 7-sulfation of taxifolin and eriodictyol attenuates but does not remove anti-oxidant activity.</div></front></TEI><pubmed><MedlineCitation Status="PubMed-not-MEDLINE" Owner="NLM"><PMID Version="1">32025274</PMID><DateRevised><Year>2020</Year><Month>10</Month><Day>10</Day></DateRevised><Article PubModel="Print"><Journal><ISSN IssnType="Print">1874-3900</ISSN><JournalIssue CitedMedium="Print"><Volume>35</Volume><PubDate><Year>2020</Year><Month>Feb</Month></PubDate></JournalIssue><Title>Phytochemistry letters</Title><ISOAbbreviation>Phytochem Lett</ISOAbbreviation></Journal><ArticleTitle>Sulfated flavanones and dihydroflavonols from willow.</ArticleTitle><Pagination><MedlinePgn>88-93</MedlinePgn></Pagination><ELocationID EIdType="doi" ValidYN="Y">10.1016/j.phytol.2019.11.008</ELocationID><Abstract><AbstractText>Phytochemical profiling of a hybrid species of willow, <i>Salix</i> × <i>alberti</i> L. (<i>S. integra</i> Thunb. × <i>Salix suchowensis</i> W.C. Cheng ex G.Zhu) revealed four sulfated flavonoids, which were then isolated from young stem tissue. The structures of dihydroflavonols (flavanonols) taxifolin-7-sulfate <b>(1)</b> and dihydrokaempferol-7-sulfate <b>(2)</b> and flavanones, eridictyol-7-sulfate <b>(3)</b> and naringenin-7-sulfate <b>(4)</b> were elucidated through NMR spectroscopy and high-resolution mass spectrometry. The identified sulfated flavanones and dihydroflavonols have not been previously seen in plants, but the former have been partially characterised as metabolites in mammalian metabolism of dietary flavonoids. In addition to providing full spectroscopic characterisation of these metabolites for the first time, we also compared the <i>in vitro</i> antioxidant properties, <i>via</i> the DPPH radical scavenging assay, of the parent and sulfated flavanones, which showed that 7-sulfation of taxifolin and eriodictyol attenuates but does not remove anti-oxidant activity.</AbstractText><CopyrightInformation>© 2019 Rothamsted Research Ltd.</CopyrightInformation></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Noleto-Dias</LastName><ForeName>Clarice</ForeName><Initials>C</Initials><AffiliationInfo><Affiliation>Department of Computational and Analytical Sciences, Rothamsted Research, West Common, Harpenden, Hertfordshire, AL5 2JQ, UK.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Harflett</LastName><ForeName>Claudia</ForeName><Initials>C</Initials><AffiliationInfo><Affiliation>Department of Computational and Analytical Sciences, Rothamsted Research, West Common, Harpenden, Hertfordshire, AL5 2JQ, UK.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Beale</LastName><ForeName>Michael H</ForeName><Initials>MH</Initials><AffiliationInfo><Affiliation>Department of Computational and Analytical Sciences, Rothamsted Research, West Common, Harpenden, Hertfordshire, AL5 2JQ, UK.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Ward</LastName><ForeName>Jane L</ForeName><Initials>JL</Initials><AffiliationInfo><Affiliation>Department of Computational and Analytical Sciences, Rothamsted Research, West Common, Harpenden, Hertfordshire, AL5 2JQ, UK.</Affiliation></AffiliationInfo></Author></AuthorList><Language>eng</Language><PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType></PublicationTypeList></Article><MedlineJournalInfo><Country>Netherlands</Country><MedlineTA>Phytochem Lett</MedlineTA><NlmUniqueID>101513432</NlmUniqueID><ISSNLinking>1874-3900</ISSNLinking></MedlineJournalInfo><KeywordList Owner="NOTNLM"><Keyword MajorTopicYN="N">Antioxidant</Keyword><Keyword MajorTopicYN="N">S. × alberti L. (S. integra Thunb. × S. suchowensis) hybrid</Keyword><Keyword MajorTopicYN="N">Salicaceae</Keyword><Keyword MajorTopicYN="N">Sulfated dihydroflavonols</Keyword><Keyword MajorTopicYN="N">Sulfated flavanones</Keyword><Keyword MajorTopicYN="N">Willow</Keyword></KeywordList></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="entrez"><Year>2020</Year><Month>2</Month><Day>7</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="pubmed"><Year>2020</Year><Month>2</Month><Day>7</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="medline"><Year>2020</Year><Month>2</Month><Day>7</Day><Hour>6</Hour><Minute>1</Minute></PubMedPubDate></History><PublicationStatus>ppublish</PublicationStatus><ArticleIdList><ArticleId IdType="pubmed">32025274</ArticleId><ArticleId IdType="doi">10.1016/j.phytol.2019.11.008</ArticleId><ArticleId IdType="pii">S1874-3900(19)30741-4</ArticleId><ArticleId IdType="pmc">PMC6988443</ArticleId></ArticleIdList><pmc-dir>pmcsd</pmc-dir>
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