Biological evaluation of anti-influenza viral activity of semi-synthetic catechin derivatives.
Identifieur interne : 000277 ( PubMed/Corpus ); précédent : 000276; suivant : 000278Biological evaluation of anti-influenza viral activity of semi-synthetic catechin derivatives.
Auteurs : Jae Min Song ; Ki Duk Park ; Kwang Hee Lee ; Young Ho Byun ; Ju Hee Park ; Sung Han Kim ; Jae Hong Kim ; Baik Lin SeongSource :
- Antiviral research [ 0166-3542 ] ; 2007.
English descriptors
- KwdEn :
- Amantadine (pharmacology), Animals, Catechin (analogs & derivatives), Catechin (chemical synthesis), Catechin (chemistry), Catechin (pharmacology), Cell Line, Chickens, Dogs, Drug Evaluation, Preclinical, Eggs (virology), Hemagglutination Inhibition Tests, Influenza A Virus, H1N1 Subtype (drug effects), Influenza A Virus, H2N2 Subtype (drug effects), Influenza A Virus, H3N2 Subtype (drug effects), Influenza A Virus, H9N2 Subtype (drug effects), Influenza B virus (drug effects), Molecular Structure, Oseltamivir (pharmacology), Structure-Activity Relationship, Viral Plaque Assay, Virus Attachment (drug effects), Virus Internalization (drug effects), Virus Replication (drug effects).
- MESH :
- chemical , analogs & derivatives : Catechin.
- chemical , chemical synthesis : Catechin.
- chemical , chemistry : Catechin.
- chemical , pharmacology : Amantadine, Catechin, Oseltamivir.
- drug effects : Influenza A Virus, H1N1 Subtype, Influenza A Virus, H2N2 Subtype, Influenza A Virus, H3N2 Subtype, Influenza A Virus, H9N2 Subtype, Influenza B virus, Virus Attachment, Virus Internalization, Virus Replication.
- virology : Eggs.
- Animals, Cell Line, Chickens, Dogs, Drug Evaluation, Preclinical, Hemagglutination Inhibition Tests, Molecular Structure, Structure-Activity Relationship, Viral Plaque Assay.
Abstract
Catechin derivatives with different alkyl chain length and aromatic ring substitutions at the 3-hydroxyl group were synthesized from epigallocatechin (EGC) and (+)-catechin (C) and their anti-influenza viral activity were evaluated in vitro and in ovo. Pronounced antiviral activity was observed for derivatives carrying moderate chain length (7-9 carbons) as compared to those with aromatic rings, whereas the 5'-hydroxyl group of the trihydroxy benzyl moiety did not significantly contribute to antiviral activity. The derivatives exerted inhibitory effects for all six influenza subtypes tested including three major types of currently circulating human influenza viruses (A/H1N1, A/H3N2 and B type), H2N2 and H9N2 avian influenza virus. The compounds strongly inhibited adsorption of the viruses on red blood cell (RBC). They also restricted the growth of avian influenza virus in ovo with minimum inhibition concentration (MIC) of 5-10 microM far exceeding the neuraminidase (NA) inhibitor oseltamivir or M2 proton channel inhibitor amantadine. The antiviral activity appears to be mediated by interaction with hemagglutinin (HA)/viral membrane rendering HA less fusogenic at the initial stage of infection. The broad spectrum activity against various subtypes of influenza viruses may complement the limitations of current antivirals and contribute for managing potentially emerging influenza pandemic. The structure-activity data of catechin derivatives may usefully guideline future research endeavors for applying green tea catechins as alternative anti-viral agents.
DOI: 10.1016/j.antiviral.2007.07.001
PubMed: 17709148
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pubmed:17709148Le document en format XML
<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">Biological evaluation of anti-influenza viral activity of semi-synthetic catechin derivatives.</title><author><name sortKey="Song, Jae Min" sort="Song, Jae Min" uniqKey="Song J" first="Jae Min" last="Song">Jae Min Song</name><affiliation><nlm:affiliation>Department of Biotechnology, College of Engineering, Yonsei University, Seoul, South Korea.</nlm:affiliation></affiliation></author><author><name sortKey="Park, Ki Duk" sort="Park, Ki Duk" uniqKey="Park K" first="Ki Duk" last="Park">Ki Duk Park</name></author><author><name sortKey="Lee, Kwang Hee" sort="Lee, Kwang Hee" uniqKey="Lee K" first="Kwang Hee" last="Lee">Kwang Hee Lee</name></author><author><name sortKey="Byun, Young Ho" sort="Byun, Young Ho" uniqKey="Byun Y" first="Young Ho" last="Byun">Young Ho Byun</name></author><author><name sortKey="Park, Ju Hee" sort="Park, Ju Hee" uniqKey="Park J" first="Ju Hee" last="Park">Ju Hee Park</name></author><author><name sortKey="Kim, Sung Han" sort="Kim, Sung Han" uniqKey="Kim S" first="Sung Han" last="Kim">Sung Han Kim</name></author><author><name sortKey="Kim, Jae Hong" sort="Kim, Jae Hong" uniqKey="Kim J" first="Jae Hong" last="Kim">Jae Hong Kim</name></author><author><name sortKey="Seong, Baik Lin" sort="Seong, Baik Lin" uniqKey="Seong B" first="Baik Lin" last="Seong">Baik Lin Seong</name></author></titleStmt><publicationStmt><idno type="wicri:source">PubMed</idno><date when="2007">2007</date><idno type="RBID">pubmed:17709148</idno><idno type="pmid">17709148</idno><idno type="doi">10.1016/j.antiviral.2007.07.001</idno><idno type="wicri:Area/PubMed/Corpus">000277</idno><idno type="wicri:explorRef" wicri:stream="PubMed" wicri:step="Corpus" wicri:corpus="PubMed">000277</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en">Biological evaluation of anti-influenza viral activity of semi-synthetic catechin derivatives.</title><author><name sortKey="Song, Jae Min" sort="Song, Jae Min" uniqKey="Song J" first="Jae Min" last="Song">Jae Min Song</name><affiliation><nlm:affiliation>Department of Biotechnology, College of Engineering, Yonsei University, Seoul, South Korea.</nlm:affiliation></affiliation></author><author><name sortKey="Park, Ki Duk" sort="Park, Ki Duk" uniqKey="Park K" first="Ki Duk" last="Park">Ki Duk Park</name></author><author><name sortKey="Lee, Kwang Hee" sort="Lee, Kwang Hee" uniqKey="Lee K" first="Kwang Hee" last="Lee">Kwang Hee Lee</name></author><author><name sortKey="Byun, Young Ho" sort="Byun, Young Ho" uniqKey="Byun Y" first="Young Ho" last="Byun">Young Ho Byun</name></author><author><name sortKey="Park, Ju Hee" sort="Park, Ju Hee" uniqKey="Park J" first="Ju Hee" last="Park">Ju Hee Park</name></author><author><name sortKey="Kim, Sung Han" sort="Kim, Sung Han" uniqKey="Kim S" first="Sung Han" last="Kim">Sung Han Kim</name></author><author><name sortKey="Kim, Jae Hong" sort="Kim, Jae Hong" uniqKey="Kim J" first="Jae Hong" last="Kim">Jae Hong Kim</name></author><author><name sortKey="Seong, Baik Lin" sort="Seong, Baik Lin" uniqKey="Seong B" first="Baik Lin" last="Seong">Baik Lin Seong</name></author></analytic><series><title level="j">Antiviral research</title><idno type="ISSN">0166-3542</idno><imprint><date when="2007" type="published">2007</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Amantadine (pharmacology)</term><term>Animals</term><term>Catechin (analogs & derivatives)</term><term>Catechin (chemical synthesis)</term><term>Catechin (chemistry)</term><term>Catechin (pharmacology)</term><term>Cell Line</term><term>Chickens</term><term>Dogs</term><term>Drug Evaluation, Preclinical</term><term>Eggs (virology)</term><term>Hemagglutination Inhibition Tests</term><term>Influenza A Virus, H1N1 Subtype (drug effects)</term><term>Influenza A Virus, H2N2 Subtype (drug effects)</term><term>Influenza A Virus, H3N2 Subtype (drug effects)</term><term>Influenza A Virus, H9N2 Subtype (drug effects)</term><term>Influenza B virus (drug effects)</term><term>Molecular Structure</term><term>Oseltamivir (pharmacology)</term><term>Structure-Activity Relationship</term><term>Viral Plaque Assay</term><term>Virus Attachment (drug effects)</term><term>Virus Internalization (drug effects)</term><term>Virus Replication (drug effects)</term></keywords><keywords scheme="MESH" type="chemical" qualifier="analogs & derivatives" xml:lang="en"><term>Catechin</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemical synthesis" xml:lang="en"><term>Catechin</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Catechin</term></keywords><keywords scheme="MESH" type="chemical" qualifier="pharmacology" xml:lang="en"><term>Amantadine</term><term>Catechin</term><term>Oseltamivir</term></keywords><keywords scheme="MESH" qualifier="drug effects" xml:lang="en"><term>Influenza A Virus, H1N1 Subtype</term><term>Influenza A Virus, H2N2 Subtype</term><term>Influenza A Virus, H3N2 Subtype</term><term>Influenza A Virus, H9N2 Subtype</term><term>Influenza B virus</term><term>Virus Attachment</term><term>Virus Internalization</term><term>Virus Replication</term></keywords><keywords scheme="MESH" qualifier="virology" xml:lang="en"><term>Eggs</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Animals</term><term>Cell Line</term><term>Chickens</term><term>Dogs</term><term>Drug Evaluation, Preclinical</term><term>Hemagglutination Inhibition Tests</term><term>Molecular Structure</term><term>Structure-Activity Relationship</term><term>Viral Plaque Assay</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">Catechin derivatives with different alkyl chain length and aromatic ring substitutions at the 3-hydroxyl group were synthesized from epigallocatechin (EGC) and (+)-catechin (C) and their anti-influenza viral activity were evaluated in vitro and in ovo. Pronounced antiviral activity was observed for derivatives carrying moderate chain length (7-9 carbons) as compared to those with aromatic rings, whereas the 5'-hydroxyl group of the trihydroxy benzyl moiety did not significantly contribute to antiviral activity. The derivatives exerted inhibitory effects for all six influenza subtypes tested including three major types of currently circulating human influenza viruses (A/H1N1, A/H3N2 and B type), H2N2 and H9N2 avian influenza virus. The compounds strongly inhibited adsorption of the viruses on red blood cell (RBC). They also restricted the growth of avian influenza virus in ovo with minimum inhibition concentration (MIC) of 5-10 microM far exceeding the neuraminidase (NA) inhibitor oseltamivir or M2 proton channel inhibitor amantadine. The antiviral activity appears to be mediated by interaction with hemagglutinin (HA)/viral membrane rendering HA less fusogenic at the initial stage of infection. The broad spectrum activity against various subtypes of influenza viruses may complement the limitations of current antivirals and contribute for managing potentially emerging influenza pandemic. The structure-activity data of catechin derivatives may usefully guideline future research endeavors for applying green tea catechins as alternative anti-viral agents.</div></front></TEI><pubmed><MedlineCitation Status="MEDLINE" Owner="NLM"><PMID Version="1">17709148</PMID><DateCompleted><Year>2007</Year><Month>11</Month><Day>27</Day></DateCompleted><DateRevised><Year>2013</Year><Month>11</Month><Day>21</Day></DateRevised><Article PubModel="Print-Electronic"><Journal><ISSN IssnType="Print">0166-3542</ISSN><JournalIssue CitedMedium="Print"><Volume>76</Volume><Issue>2</Issue><PubDate><Year>2007</Year><Month>Nov</Month></PubDate></JournalIssue><Title>Antiviral research</Title><ISOAbbreviation>Antiviral Res.</ISOAbbreviation></Journal><ArticleTitle>Biological evaluation of anti-influenza viral activity of semi-synthetic catechin derivatives.</ArticleTitle><Pagination><MedlinePgn>178-85</MedlinePgn></Pagination><Abstract><AbstractText>Catechin derivatives with different alkyl chain length and aromatic ring substitutions at the 3-hydroxyl group were synthesized from epigallocatechin (EGC) and (+)-catechin (C) and their anti-influenza viral activity were evaluated in vitro and in ovo. Pronounced antiviral activity was observed for derivatives carrying moderate chain length (7-9 carbons) as compared to those with aromatic rings, whereas the 5'-hydroxyl group of the trihydroxy benzyl moiety did not significantly contribute to antiviral activity. The derivatives exerted inhibitory effects for all six influenza subtypes tested including three major types of currently circulating human influenza viruses (A/H1N1, A/H3N2 and B type), H2N2 and H9N2 avian influenza virus. The compounds strongly inhibited adsorption of the viruses on red blood cell (RBC). They also restricted the growth of avian influenza virus in ovo with minimum inhibition concentration (MIC) of 5-10 microM far exceeding the neuraminidase (NA) inhibitor oseltamivir or M2 proton channel inhibitor amantadine. The antiviral activity appears to be mediated by interaction with hemagglutinin (HA)/viral membrane rendering HA less fusogenic at the initial stage of infection. The broad spectrum activity against various subtypes of influenza viruses may complement the limitations of current antivirals and contribute for managing potentially emerging influenza pandemic. The structure-activity data of catechin derivatives may usefully guideline future research endeavors for applying green tea catechins as alternative anti-viral agents.</AbstractText></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Song</LastName><ForeName>Jae Min</ForeName><Initials>JM</Initials><AffiliationInfo><Affiliation>Department of Biotechnology, College of Engineering, Yonsei University, Seoul, South Korea.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Park</LastName><ForeName>Ki Duk</ForeName><Initials>KD</Initials></Author><Author ValidYN="Y"><LastName>Lee</LastName><ForeName>Kwang Hee</ForeName><Initials>KH</Initials></Author><Author ValidYN="Y"><LastName>Byun</LastName><ForeName>Young Ho</ForeName><Initials>YH</Initials></Author><Author ValidYN="Y"><LastName>Park</LastName><ForeName>Ju Hee</ForeName><Initials>JH</Initials></Author><Author ValidYN="Y"><LastName>Kim</LastName><ForeName>Sung Han</ForeName><Initials>SH</Initials></Author><Author ValidYN="Y"><LastName>Kim</LastName><ForeName>Jae Hong</ForeName><Initials>JH</Initials></Author><Author ValidYN="Y"><LastName>Seong</LastName><ForeName>Baik Lin</ForeName><Initials>BL</Initials></Author></AuthorList><Language>eng</Language><PublicationTypeList><PublicationType UI="D003160">Comparative Study</PublicationType><PublicationType UI="D016428">Journal Article</PublicationType></PublicationTypeList><ArticleDate DateType="Electronic"><Year>2007</Year><Month>08</Month><Day>01</Day></ArticleDate></Article><MedlineJournalInfo><Country>Netherlands</Country><MedlineTA>Antiviral Res</MedlineTA><NlmUniqueID>8109699</NlmUniqueID><ISSNLinking>0166-3542</ISSNLinking></MedlineJournalInfo><ChemicalList><Chemical><RegistryNumber>20O93L6F9H</RegistryNumber><NameOfSubstance UI="D053139">Oseltamivir</NameOfSubstance></Chemical><Chemical><RegistryNumber>8R1V1STN48</RegistryNumber><NameOfSubstance UI="D002392">Catechin</NameOfSubstance></Chemical><Chemical><RegistryNumber>BF4C9Z1J53</RegistryNumber><NameOfSubstance UI="D000547">Amantadine</NameOfSubstance></Chemical></ChemicalList><CitationSubset>IM</CitationSubset><MeshHeadingList><MeshHeading><DescriptorName UI="D000547" MajorTopicYN="N">Amantadine</DescriptorName><QualifierName UI="Q000494" MajorTopicYN="N">pharmacology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D000818" MajorTopicYN="N">Animals</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D002392" MajorTopicYN="N">Catechin</DescriptorName><QualifierName UI="Q000031" MajorTopicYN="Y">analogs & derivatives</QualifierName><QualifierName UI="Q000138" MajorTopicYN="N">chemical synthesis</QualifierName><QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName><QualifierName UI="Q000494" MajorTopicYN="Y">pharmacology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D002460" MajorTopicYN="N">Cell Line</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D002645" MajorTopicYN="N">Chickens</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D004285" MajorTopicYN="N">Dogs</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D004353" MajorTopicYN="N">Drug Evaluation, Preclinical</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D004531" MajorTopicYN="N">Eggs</DescriptorName><QualifierName UI="Q000821" MajorTopicYN="N">virology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D006385" MajorTopicYN="N">Hemagglutination Inhibition Tests</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D053118" MajorTopicYN="N">Influenza A Virus, H1N1 Subtype</DescriptorName><QualifierName UI="Q000187" MajorTopicYN="Y">drug effects</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D053121" MajorTopicYN="N">Influenza A Virus, H2N2 Subtype</DescriptorName><QualifierName UI="Q000187" MajorTopicYN="Y">drug effects</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D053122" MajorTopicYN="N">Influenza A Virus, H3N2 Subtype</DescriptorName><QualifierName UI="Q000187" MajorTopicYN="Y">drug effects</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D053127" MajorTopicYN="N">Influenza A Virus, H9N2 Subtype</DescriptorName><QualifierName UI="Q000187" MajorTopicYN="Y">drug effects</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D009981" MajorTopicYN="N">Influenza B virus</DescriptorName><QualifierName UI="Q000187" MajorTopicYN="Y">drug effects</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D015394" MajorTopicYN="N">Molecular Structure</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D053139" MajorTopicYN="N">Oseltamivir</DescriptorName><QualifierName UI="Q000494" MajorTopicYN="N">pharmacology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D013329" MajorTopicYN="N">Structure-Activity Relationship</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D010948" MajorTopicYN="N">Viral Plaque Assay</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D053585" MajorTopicYN="N">Virus Attachment</DescriptorName><QualifierName UI="Q000187" MajorTopicYN="N">drug effects</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D053586" MajorTopicYN="N">Virus Internalization</DescriptorName><QualifierName UI="Q000187" MajorTopicYN="N">drug effects</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D014779" MajorTopicYN="N">Virus Replication</DescriptorName><QualifierName UI="Q000187" MajorTopicYN="N">drug effects</QualifierName></MeshHeading></MeshHeadingList></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="received"><Year>2007</Year><Month>04</Month><Day>23</Day></PubMedPubDate><PubMedPubDate PubStatus="revised"><Year>2007</Year><Month>07</Month><Day>03</Day></PubMedPubDate><PubMedPubDate PubStatus="accepted"><Year>2007</Year><Month>07</Month><Day>05</Day></PubMedPubDate><PubMedPubDate PubStatus="pubmed"><Year>2007</Year><Month>8</Month><Day>22</Day><Hour>9</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="medline"><Year>2007</Year><Month>12</Month><Day>6</Day><Hour>9</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="entrez"><Year>2007</Year><Month>8</Month><Day>22</Day><Hour>9</Hour><Minute>0</Minute></PubMedPubDate></History><PublicationStatus>ppublish</PublicationStatus><ArticleIdList><ArticleId IdType="pubmed">17709148</ArticleId><ArticleId IdType="pii">S0166-3542(07)00371-3</ArticleId><ArticleId IdType="doi">10.1016/j.antiviral.2007.07.001</ArticleId></ArticleIdList></PubmedData></pubmed></record>Pour manipuler ce document sous Unix (Dilib)
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