Phenolic Glycosides from the Twigs of Salix glandulosa.
Identifieur interne : 001059 ( Main/Corpus ); précédent : 001058; suivant : 001060Phenolic Glycosides from the Twigs of Salix glandulosa.
Auteurs : Chung Sub Kim ; Oh Wook Kwon ; Sun Yeou Kim ; Sang Un Choi ; Jae Yoon Kim ; Ji Young Han ; Soo Im Choi ; Jong Gil Choi ; Ki Hyun Kim ; Kang Ro LeeSource :
- Journal of natural products [ 1520-6025 ] ; 2014.
English descriptors
- KwdEn :
- Animals (MeSH), Glycosides (chemistry), Glycosides (isolation & purification), Glycosides (pharmacology), Lipopolysaccharides (pharmacology), Macrophages (drug effects), Mice (MeSH), Molecular Structure (MeSH), Nitric Oxide (biosynthesis), Nuclear Magnetic Resonance, Biomolecular (MeSH), Phenols (chemistry), Phenols (isolation & purification), Phenols (pharmacology), Plant Stems (chemistry), Plants, Medicinal (chemistry), Republic of Korea (MeSH), Salix (chemistry), Stereoisomerism (MeSH).
- MESH :
- chemical , biosynthesis : Nitric Oxide.
- chemical , chemistry : Glycosides, Phenols.
- chemical , isolation & purification : Glycosides, Phenols.
- chemical , pharmacology : Glycosides, Lipopolysaccharides, Phenols.
- geographic : Republic of Korea.
- chemistry : Plant Stems, Plants, Medicinal, Salix.
- drug effects : Macrophages.
- Animals, Mice, Molecular Structure, Nuclear Magnetic Resonance, Biomolecular, Stereoisomerism.
Abstract
As a part of an ongoing search for bioactive constituents from Korean medicinal plants, the phytochemical investigations of the twigs of Salix glandulosa afforded 12 new phenolic glycosides (1-12) and a known analogue (13). The structures of 1-13 were characterized by a combination of NMR methods ((1)H and (13)C NMR, (1)H-(1)H COSY, HMQC, and HMBC), chemical hydrolysis, and GC/MS. The absolute configuration of 13 [(1R,2S)-2-hydroxycyclohexyl-2'-O-trans-p-coumaroyl-β-d-glucopyranoside] was determined for the first time. Compounds 1-3, 6, and 7 exhibited inhibitory effects on nitric oxide production in lipopolysaccharide-activated murine microglial cells (IC50 values in the range 6.6-20.5 μM).
DOI: 10.1021/np500488v
PubMed: 25098650
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pubmed:25098650Le document en format XML
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Ltd. , 909 Chung-anginnotech Intellectual Industry Center, Seongnam 432-807, Republic of Korea.</nlm:affiliation></affiliation></author><author><name sortKey="Han, Ji Young" sort="Han, Ji Young" uniqKey="Han J" first="Ji Young" last="Han">Ji Young Han</name><affiliation><nlm:affiliation>YD Global Life Science Co. Ltd. , 909 Chung-anginnotech Intellectual Industry Center, Seongnam 432-807, Republic of Korea.</nlm:affiliation></affiliation></author><author><name sortKey="Choi, Soo Im" sort="Choi, Soo Im" uniqKey="Choi S" first="Soo Im" last="Choi">Soo Im Choi</name><affiliation><nlm:affiliation>YD Global Life Science Co. Ltd. , 909 Chung-anginnotech Intellectual Industry Center, Seongnam 432-807, Republic of Korea.</nlm:affiliation></affiliation></author><author><name sortKey="Choi, Jong Gil" sort="Choi, Jong Gil" uniqKey="Choi J" first="Jong Gil" last="Choi">Jong Gil Choi</name><affiliation><nlm:affiliation>YD Global Life Science Co. Ltd. , 909 Chung-anginnotech Intellectual Industry Center, Seongnam 432-807, Republic of Korea.</nlm:affiliation></affiliation></author><author><name sortKey="Kim, Ki Hyun" sort="Kim, Ki Hyun" uniqKey="Kim K" first="Ki Hyun" last="Kim">Ki Hyun Kim</name><affiliation><nlm:affiliation>Natural Products Laboratory, School of Pharmacy, Sungkyunkwan University , Suwon 440-746, Republic of Korea.</nlm:affiliation></affiliation></author><author><name sortKey="Lee, Kang Ro" sort="Lee, Kang Ro" uniqKey="Lee K" first="Kang Ro" last="Lee">Kang Ro Lee</name><affiliation><nlm:affiliation>Natural Products Laboratory, School of Pharmacy, Sungkyunkwan University , Suwon 440-746, Republic of Korea.</nlm:affiliation></affiliation></author></analytic><series><title level="j">Journal of natural products</title><idno type="eISSN">1520-6025</idno><imprint><date when="2014" type="published">2014</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Animals (MeSH)</term><term>Glycosides (chemistry)</term><term>Glycosides (isolation & purification)</term><term>Glycosides (pharmacology)</term><term>Lipopolysaccharides (pharmacology)</term><term>Macrophages (drug effects)</term><term>Mice (MeSH)</term><term>Molecular Structure (MeSH)</term><term>Nitric Oxide (biosynthesis)</term><term>Nuclear Magnetic Resonance, Biomolecular (MeSH)</term><term>Phenols (chemistry)</term><term>Phenols (isolation & purification)</term><term>Phenols (pharmacology)</term><term>Plant Stems (chemistry)</term><term>Plants, Medicinal (chemistry)</term><term>Republic of Korea (MeSH)</term><term>Salix (chemistry)</term><term>Stereoisomerism (MeSH)</term></keywords><keywords scheme="MESH" type="chemical" qualifier="biosynthesis" xml:lang="en"><term>Nitric Oxide</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Glycosides</term><term>Phenols</term></keywords><keywords scheme="MESH" type="chemical" qualifier="isolation & purification" xml:lang="en"><term>Glycosides</term><term>Phenols</term></keywords><keywords scheme="MESH" type="chemical" qualifier="pharmacology" xml:lang="en"><term>Glycosides</term><term>Lipopolysaccharides</term><term>Phenols</term></keywords><keywords scheme="MESH" type="geographic" xml:lang="en"><term>Republic of Korea</term></keywords><keywords scheme="MESH" qualifier="chemistry" xml:lang="en"><term>Plant Stems</term><term>Plants, Medicinal</term><term>Salix</term></keywords><keywords scheme="MESH" qualifier="drug effects" xml:lang="en"><term>Macrophages</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Animals</term><term>Mice</term><term>Molecular Structure</term><term>Nuclear Magnetic Resonance, Biomolecular</term><term>Stereoisomerism</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">As a part of an ongoing search for bioactive constituents from Korean medicinal plants, the phytochemical investigations of the twigs of Salix glandulosa afforded 12 new phenolic glycosides (1-12) and a known analogue (13). The structures of 1-13 were characterized by a combination of NMR methods ((1)H and (13)C NMR, (1)H-(1)H COSY, HMQC, and HMBC), chemical hydrolysis, and GC/MS. The absolute configuration of 13 [(1R,2S)-2-hydroxycyclohexyl-2'-O-trans-p-coumaroyl-β-d-glucopyranoside] was determined for the first time. Compounds 1-3, 6, and 7 exhibited inhibitory effects on nitric oxide production in lipopolysaccharide-activated murine microglial cells (IC50 values in the range 6.6-20.5 μM). </div></front></TEI><pubmed><MedlineCitation Status="MEDLINE" Owner="NLM"><PMID Version="1">25098650</PMID><DateCompleted><Year>2015</Year><Month>10</Month><Day>16</Day></DateCompleted><DateRevised><Year>2015</Year><Month>09</Month><Day>09</Day></DateRevised><Article PubModel="Print-Electronic"><Journal><ISSN IssnType="Electronic">1520-6025</ISSN><JournalIssue CitedMedium="Internet"><Volume>77</Volume><Issue>8</Issue><PubDate><Year>2014</Year><Month>Aug</Month><Day>22</Day></PubDate></JournalIssue><Title>Journal of natural products</Title><ISOAbbreviation>J Nat Prod</ISOAbbreviation></Journal><ArticleTitle>Phenolic Glycosides from the Twigs of Salix glandulosa.</ArticleTitle><Pagination><MedlinePgn>1955-61</MedlinePgn></Pagination><ELocationID EIdType="doi" ValidYN="Y">10.1021/np500488v</ELocationID><Abstract><AbstractText>As a part of an ongoing search for bioactive constituents from Korean medicinal plants, the phytochemical investigations of the twigs of Salix glandulosa afforded 12 new phenolic glycosides (1-12) and a known analogue (13). The structures of 1-13 were characterized by a combination of NMR methods ((1)H and (13)C NMR, (1)H-(1)H COSY, HMQC, and HMBC), chemical hydrolysis, and GC/MS. The absolute configuration of 13 [(1R,2S)-2-hydroxycyclohexyl-2'-O-trans-p-coumaroyl-β-d-glucopyranoside] was determined for the first time. Compounds 1-3, 6, and 7 exhibited inhibitory effects on nitric oxide production in lipopolysaccharide-activated murine microglial cells (IC50 values in the range 6.6-20.5 μM). </AbstractText></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Kim</LastName><ForeName>Chung Sub</ForeName><Initials>CS</Initials><AffiliationInfo><Affiliation>Natural Products Laboratory, School of Pharmacy, Sungkyunkwan University , Suwon 440-746, Republic of Korea.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Kwon</LastName><ForeName>Oh Wook</ForeName><Initials>OW</Initials><AffiliationInfo><Affiliation>Graduate School of East-West Medical Science, Kyung Hee University , Yongin 446-701, Republic of Korea.</Affiliation></AffiliationInfo><AffiliationInfo><Affiliation>Gachon Institute of Pharmaceutical Science, Gachon University , Incheon, 406-799, Republic of Korea.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Kim</LastName><ForeName>Sun Yeou</ForeName><Initials>SY</Initials><AffiliationInfo><Affiliation>Gachon Institute of Pharmaceutical Science, Gachon University , Incheon, 406-799, Republic of Korea.</Affiliation></AffiliationInfo><AffiliationInfo><Affiliation>College of Pharmacy, Gachon University , Incheon 406-799, Republic of Korea.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Choi</LastName><ForeName>Sang Un</ForeName><Initials>SU</Initials><AffiliationInfo><Affiliation>Korea Research Institute of Chemical Technology , Daejeon 305-343, Republic of Korea.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Kim</LastName><ForeName>Jae Yoon</ForeName><Initials>JY</Initials><AffiliationInfo><Affiliation>YD Global Life Science Co. Ltd. , 909 Chung-anginnotech Intellectual Industry Center, Seongnam 432-807, Republic of Korea.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Han</LastName><ForeName>Ji Young</ForeName><Initials>JY</Initials><AffiliationInfo><Affiliation>YD Global Life Science Co. Ltd. , 909 Chung-anginnotech Intellectual Industry Center, Seongnam 432-807, Republic of Korea.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Choi</LastName><ForeName>Soo Im</ForeName><Initials>SI</Initials><AffiliationInfo><Affiliation>YD Global Life Science Co. Ltd. , 909 Chung-anginnotech Intellectual Industry Center, Seongnam 432-807, Republic of Korea.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Choi</LastName><ForeName>Jong Gil</ForeName><Initials>JG</Initials><AffiliationInfo><Affiliation>YD Global Life Science Co. Ltd. , 909 Chung-anginnotech Intellectual Industry Center, Seongnam 432-807, Republic of Korea.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Kim</LastName><ForeName>Ki Hyun</ForeName><Initials>KH</Initials><AffiliationInfo><Affiliation>Natural Products Laboratory, School of Pharmacy, Sungkyunkwan University , Suwon 440-746, Republic of Korea.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Lee</LastName><ForeName>Kang Ro</ForeName><Initials>KR</Initials><AffiliationInfo><Affiliation>Natural Products Laboratory, School of Pharmacy, Sungkyunkwan University , Suwon 440-746, Republic of Korea.</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>2014</Year><Month>08</Month><Day>06</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="D006027">Glycosides</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D008070">Lipopolysaccharides</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D010636">Phenols</NameOfSubstance></Chemical><Chemical><RegistryNumber>31C4KY9ESH</RegistryNumber><NameOfSubstance UI="D009569">Nitric Oxide</NameOfSubstance></Chemical></ChemicalList><CitationSubset>IM</CitationSubset><MeshHeadingList><MeshHeading><DescriptorName UI="D000818" MajorTopicYN="N">Animals</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D006027" MajorTopicYN="N">Glycosides</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName><QualifierName UI="Q000302" MajorTopicYN="Y">isolation & purification</QualifierName><QualifierName UI="Q000494" MajorTopicYN="N">pharmacology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D008070" MajorTopicYN="N">Lipopolysaccharides</DescriptorName><QualifierName UI="Q000494" MajorTopicYN="N">pharmacology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D008264" MajorTopicYN="N">Macrophages</DescriptorName><QualifierName UI="Q000187" MajorTopicYN="N">drug effects</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D051379" MajorTopicYN="N">Mice</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D015394" MajorTopicYN="N">Molecular Structure</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D009569" MajorTopicYN="N">Nitric Oxide</DescriptorName><QualifierName UI="Q000096" MajorTopicYN="N">biosynthesis</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D019906" MajorTopicYN="N">Nuclear Magnetic Resonance, Biomolecular</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D010636" MajorTopicYN="N">Phenols</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName><QualifierName UI="Q000302" MajorTopicYN="Y">isolation & purification</QualifierName><QualifierName UI="Q000494" MajorTopicYN="N">pharmacology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D018547" MajorTopicYN="N">Plant Stems</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D010946" MajorTopicYN="N">Plants, Medicinal</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="Y">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D056910" MajorTopicYN="N" Type="Geographic">Republic of Korea</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D032108" MajorTopicYN="N">Salix</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="Y">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D013237" MajorTopicYN="N">Stereoisomerism</DescriptorName></MeshHeading></MeshHeadingList></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="entrez"><Year>2014</Year><Month>8</Month><Day>8</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="pubmed"><Year>2014</Year><Month>8</Month><Day>8</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="medline"><Year>2015</Year><Month>10</Month><Day>17</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate></History><PublicationStatus>ppublish</PublicationStatus><ArticleIdList><ArticleId IdType="pubmed">25098650</ArticleId><ArticleId IdType="doi">10.1021/np500488v</ArticleId></ArticleIdList></PubmedData></pubmed></record>Pour manipuler ce document sous Unix (Dilib)
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