SrasV1, Ncbi, Merge, bibRecord, 002A42

Isolation, synthesis and anti-hepatitis B virus evaluation of p-hydroxyacetophenone derivatives from Artemisia capillaris.

Identifieur interne : 002A42 ( Ncbi/Merge ); précédent : 002A41; suivant : 002A43

Isolation, synthesis and anti-hepatitis B virus evaluation of p-hydroxyacetophenone derivatives from Artemisia capillaris.

Auteurs : Yong Zhao [République populaire de Chine] ; Chang-An Geng [République populaire de Chine] ; Hao Chen [République populaire de Chine] ; Yun-Bao Ma [République populaire de Chine] ; Xiao-Yan Huang [République populaire de Chine] ; Tuan-Wu Cao [République populaire de Chine] ; Kang He [République populaire de Chine] ; Hao Wang [République populaire de Chine] ; Xue-Mei Zhang [République populaire de Chine] ; Ji-Jun Chen [République populaire de Chine]

Source :

Bioorganic & medicinal chemistry letters [ 1464-3405 ] ; 2015.

RBID : pubmed:25737008

Descripteurs français

KwdFr :
- Acétophénones (), Acétophénones (isolement et purification), Acétophénones (pharmacologie), Antigènes de surface du virus de l'hépatite B (), Antiviraux (), Antiviraux (isolement et purification), Antiviraux (pharmacologie), Artemisia (), Relation dose-effet des médicaments, Relation structure-activité, Structure moléculaire, Tests de sensibilité microbienne, Virus de l'hépatite B ().
MESH :
- isolement et purification : Acétophénones, Antiviraux.
- pharmacologie : Acétophénones, Antiviraux.
- Acétophénones, Antigènes de surface du virus de l'hépatite B, Antiviraux, Artemisia, Relation dose-effet des médicaments, Relation structure-activité, Structure moléculaire, Tests de sensibilité microbienne, Virus de l'hépatite B.

English descriptors

KwdEn :
- Acetophenones (chemistry), Acetophenones (isolation & purification), Acetophenones (pharmacology), Antiviral Agents (chemistry), Antiviral Agents (isolation & purification), Antiviral Agents (pharmacology), Artemisia (chemistry), Dose-Response Relationship, Drug, Hepatitis B Surface Antigens (drug effects), Hepatitis B virus (drug effects), Microbial Sensitivity Tests, Molecular Structure, Structure-Activity Relationship.
MESH :
- chemical , chemistry : Acetophenones, Antiviral Agents.
- chemical , drug effects : Hepatitis B Surface Antigens.
- chemical , isolation & purification : Acetophenones, Antiviral Agents.
- chemical , pharmacology : Acetophenones, Antiviral Agents.
- chemistry : Artemisia.
- drug effects : Hepatitis B virus.
- Dose-Response Relationship, Drug, Microbial Sensitivity Tests, Molecular Structure, Structure-Activity Relationship.

Abstract

p-Hydroxyacetophenone (p-HAP), as a main hepatoprotective and choleretic constituent of Artemisia capillaris, was revealed with anti-hepatitis B virus (HBV) effects in recent investigation. In addition to p-HAP, four derivatives of p-HAP were also isolated from A. capillaris by various chromatographic methods. Subsequent structural modification on p-HAP and its glycoside led to the synthesis of 28 additional derivatives, of which 13 compounds showed activity inhibiting hepatitis B surface antigen (HBsAg) secretion; and 18 compounds possessed inhibition on HBV DNA replication. The primary structure-activity relationships (SARs) suggested that the conjugated derivatives of p-HAP glycoside and substituted cinnamic acids (2a-2i) obviously enhanced the activity against HBV DNA replication with IC50 values ranged from 5.8 to 74.4 μM.

DOI: 10.1016/j.bmcl.2015.02.024
PubMed: 25737008

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Le document en format XML

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<term>Antiviral Agents (isolation & purification)</term>
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<term>Antiviraux (pharmacologie)</term>
<term>Artemisia ()</term>
<term>Relation dose-effet des médicaments</term>
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<term>Tests de sensibilité microbienne</term>
<term>Virus de l'hépatite B ()</term>
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<front><div type="abstract" xml:lang="en">p-Hydroxyacetophenone (p-HAP), as a main hepatoprotective and choleretic constituent of Artemisia capillaris, was revealed with anti-hepatitis B virus (HBV) effects in recent investigation. In addition to p-HAP, four derivatives of p-HAP were also isolated from A. capillaris by various chromatographic methods. Subsequent structural modification on p-HAP and its glycoside led to the synthesis of 28 additional derivatives, of which 13 compounds showed activity inhibiting hepatitis B surface antigen (HBsAg) secretion; and 18 compounds possessed inhibition on HBV DNA replication. The primary structure-activity relationships (SARs) suggested that the conjugated derivatives of p-HAP glycoside and substituted cinnamic acids (2a-2i) obviously enhanced the activity against HBV DNA replication with IC50 values ranged from 5.8 to 74.4 μM.</div>
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<Title>Bioorganic & medicinal chemistry letters</Title>
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<ArticleTitle>Isolation, synthesis and anti-hepatitis B virus evaluation of p-hydroxyacetophenone derivatives from Artemisia capillaris.</ArticleTitle>
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<Abstract><AbstractText>p-Hydroxyacetophenone (p-HAP), as a main hepatoprotective and choleretic constituent of Artemisia capillaris, was revealed with anti-hepatitis B virus (HBV) effects in recent investigation. In addition to p-HAP, four derivatives of p-HAP were also isolated from A. capillaris by various chromatographic methods. Subsequent structural modification on p-HAP and its glycoside led to the synthesis of 28 additional derivatives, of which 13 compounds showed activity inhibiting hepatitis B surface antigen (HBsAg) secretion; and 18 compounds possessed inhibition on HBV DNA replication. The primary structure-activity relationships (SARs) suggested that the conjugated derivatives of p-HAP glycoside and substituted cinnamic acids (2a-2i) obviously enhanced the activity against HBV DNA replication with IC50 values ranged from 5.8 to 74.4 μM.</AbstractText>
<CopyrightInformation>Copyright © 2015 Elsevier Ltd. All rights reserved.</CopyrightInformation>
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<AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Zhao</LastName>
<ForeName>Yong</ForeName>
<Initials>Y</Initials>
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<Author ValidYN="Y"><LastName>Chen</LastName>
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<Author ValidYN="Y"><LastName>Huang</LastName>
<ForeName>Xiao-Yan</ForeName>
<Initials>XY</Initials>
<AffiliationInfo><Affiliation>State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, PR China.</Affiliation>
</AffiliationInfo>
</Author>
<Author ValidYN="Y"><LastName>Cao</LastName>
<ForeName>Tuan-Wu</ForeName>
<Initials>TW</Initials>
<AffiliationInfo><Affiliation>State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, PR China.</Affiliation>
</AffiliationInfo>
</Author>
<Author ValidYN="Y"><LastName>He</LastName>
<ForeName>Kang</ForeName>
<Initials>K</Initials>
<AffiliationInfo><Affiliation>State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, PR China.</Affiliation>
</AffiliationInfo>
</Author>
<Author ValidYN="Y"><LastName>Wang</LastName>
<ForeName>Hao</ForeName>
<Initials>H</Initials>
<AffiliationInfo><Affiliation>State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, PR China.</Affiliation>
</AffiliationInfo>
</Author>
<Author ValidYN="Y"><LastName>Zhang</LastName>
<ForeName>Xue-Mei</ForeName>
<Initials>XM</Initials>
<AffiliationInfo><Affiliation>State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, PR China.</Affiliation>
</AffiliationInfo>
</Author>
<Author ValidYN="Y"><LastName>Chen</LastName>
<ForeName>Ji-Jun</ForeName>
<Initials>JJ</Initials>
<AffiliationInfo><Affiliation>State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, PR China. Electronic address: chenjj@mail.kib.ac.cn.</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>02</Month>
<Day>18</Day>
</ArticleDate>
</Article>
<MedlineJournalInfo><Country>England</Country>
<MedlineTA>Bioorg Med Chem Lett</MedlineTA>
<NlmUniqueID>9107377</NlmUniqueID>
<ISSNLinking>0960-894X</ISSNLinking>
</MedlineJournalInfo>
<ChemicalList><Chemical><RegistryNumber>0</RegistryNumber>
<NameOfSubstance UI="D000098">Acetophenones</NameOfSubstance>
</Chemical>
<Chemical><RegistryNumber>0</RegistryNumber>
<NameOfSubstance UI="D000998">Antiviral Agents</NameOfSubstance>
</Chemical>
<Chemical><RegistryNumber>0</RegistryNumber>
<NameOfSubstance UI="D006514">Hepatitis B Surface Antigens</NameOfSubstance>
</Chemical>
<Chemical><RegistryNumber>G1L3HT4CMH</RegistryNumber>
<NameOfSubstance UI="C031335">4-hydroxyacetophenone</NameOfSubstance>
</Chemical>
</ChemicalList>
<CitationSubset>IM</CitationSubset>
<MeshHeadingList><MeshHeading><DescriptorName UI="D000098" MajorTopicYN="N">Acetophenones</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="D000998" MajorTopicYN="N">Antiviral Agents</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="D019306" MajorTopicYN="N">Artemisia</DescriptorName>
<QualifierName UI="Q000737" MajorTopicYN="Y">chemistry</QualifierName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D004305" MajorTopicYN="N">Dose-Response Relationship, Drug</DescriptorName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D006514" MajorTopicYN="N">Hepatitis B Surface Antigens</DescriptorName>
<QualifierName UI="Q000187" MajorTopicYN="N">drug effects</QualifierName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D006515" MajorTopicYN="N">Hepatitis B virus</DescriptorName>
<QualifierName UI="Q000187" MajorTopicYN="Y">drug effects</QualifierName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D008826" MajorTopicYN="N">Microbial Sensitivity Tests</DescriptorName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D015394" MajorTopicYN="N">Molecular Structure</DescriptorName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D013329" MajorTopicYN="N">Structure-Activity Relationship</DescriptorName>
</MeshHeading>
</MeshHeadingList>
<KeywordList Owner="NOTNLM"><Keyword MajorTopicYN="N">Anti-HBV activity</Keyword>
<Keyword MajorTopicYN="N">Artemisia capillaris</Keyword>
<Keyword MajorTopicYN="N">Structure–activity relationships</Keyword>
<Keyword MajorTopicYN="N">p-Hydroxyacetophenone derivatives</Keyword>
</KeywordList>
</MedlineCitation>
<PubmedData><History><PubMedPubDate PubStatus="received"><Year>2014</Year>
<Month>12</Month>
<Day>15</Day>
</PubMedPubDate>
<PubMedPubDate PubStatus="revised"><Year>2015</Year>
<Month>01</Month>
<Day>31</Day>
</PubMedPubDate>
<PubMedPubDate PubStatus="accepted"><Year>2015</Year>
<Month>02</Month>
<Day>10</Day>
</PubMedPubDate>
<PubMedPubDate PubStatus="entrez"><Year>2015</Year>
<Month>3</Month>
<Day>5</Day>
<Hour>6</Hour>
<Minute>0</Minute>
</PubMedPubDate>
<PubMedPubDate PubStatus="pubmed"><Year>2015</Year>
<Month>3</Month>
<Day>5</Day>
<Hour>6</Hour>
<Minute>0</Minute>
</PubMedPubDate>
<PubMedPubDate PubStatus="medline"><Year>2015</Year>
<Month>12</Month>
<Day>22</Day>
<Hour>6</Hour>
<Minute>0</Minute>
</PubMedPubDate>
</History>
<PublicationStatus>ppublish</PublicationStatus>
<ArticleIdList><ArticleId IdType="pubmed">25737008</ArticleId>
<ArticleId IdType="pii">S0960-894X(15)00131-6</ArticleId>
<ArticleId IdType="doi">10.1016/j.bmcl.2015.02.024</ArticleId>
</ArticleIdList>
</PubmedData>
</pubmed>
<affiliations><list><country><li>République populaire de Chine</li>
</country>
</list>
<tree><country name="République populaire de Chine"><noRegion><name sortKey="Zhao, Yong" sort="Zhao, Yong" uniqKey="Zhao Y" first="Yong" last="Zhao">Yong Zhao</name>
</noRegion>
<name sortKey="Cao, Tuan Wu" sort="Cao, Tuan Wu" uniqKey="Cao T" first="Tuan-Wu" last="Cao">Tuan-Wu Cao</name>
<name sortKey="Chen, Hao" sort="Chen, Hao" uniqKey="Chen H" first="Hao" last="Chen">Hao Chen</name>
<name sortKey="Chen, Ji Jun" sort="Chen, Ji Jun" uniqKey="Chen J" first="Ji-Jun" last="Chen">Ji-Jun Chen</name>
<name sortKey="Geng, Chang An" sort="Geng, Chang An" uniqKey="Geng C" first="Chang-An" last="Geng">Chang-An Geng</name>
<name sortKey="He, Kang" sort="He, Kang" uniqKey="He K" first="Kang" last="He">Kang He</name>
<name sortKey="Huang, Xiao Yan" sort="Huang, Xiao Yan" uniqKey="Huang X" first="Xiao-Yan" last="Huang">Xiao-Yan Huang</name>
<name sortKey="Ma, Yun Bao" sort="Ma, Yun Bao" uniqKey="Ma Y" first="Yun-Bao" last="Ma">Yun-Bao Ma</name>
<name sortKey="Wang, Hao" sort="Wang, Hao" uniqKey="Wang H" first="Hao" last="Wang">Hao Wang</name>
<name sortKey="Zhang, Xue Mei" sort="Zhang, Xue Mei" uniqKey="Zhang X" first="Xue-Mei" last="Zhang">Xue-Mei Zhang</name>
</country>
</tree>
</affiliations>
</record>

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Isolation, synthesis and anti-hepatitis B virus evaluation of p-hydroxyacetophenone derivatives from Artemisia capillaris.

Isolation, synthesis and anti-hepatitis B virus evaluation of p-hydroxyacetophenone derivatives from Artemisia capillaris.

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