Biological evaluation of anti-influenza viral activity of semi-synthetic catechin derivatives
Identifieur interne : 001454 ( Main/Exploration ); précédent : 001453; suivant : 001455Biological evaluation of anti-influenza viral activity of semi-synthetic catechin derivatives
Auteurs : JAE MIN SONG [Corée du Sud] ; KI DUK PARK [Corée du Sud] ; KWANG HEE LEE [Corée du Sud] ; YOUNG HO BYUN [Corée du Sud] ; JU HEE PARK [Corée du Sud] ; SUNG HAN KIM [Corée du Sud] ; JAE HONG KIM [Corée du Sud] ; BAIK LIN SEONG [Corée du Sud]Source :
- Antiviral research [ 0166-3542 ] ; 2007.
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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 μM 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.
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SONG</name><affiliation wicri:level="3"><inist:fA14 i1="01"><s1>Department of Biotechnology, College of Engineering, Yonsei University</s1><s2>Seoul</s2><s3>KOR</s3><sZ>1 aut.</sZ><sZ>2 aut.</sZ><sZ>3 aut.</sZ><sZ>4 aut.</sZ><sZ>5 aut.</sZ><sZ>8 aut.</sZ></inist:fA14><country>Corée du Sud</country><placeName><settlement type="city">Séoul</settlement><region type="capital">Région capitale de Séoul</region></placeName></affiliation></author><author><name sortKey="Ki Duk Park" sort="Ki Duk Park" uniqKey="Ki Duk Park" last="Ki Duk Park">KI DUK PARK</name><affiliation wicri:level="3"><inist:fA14 i1="01"><s1>Department of Biotechnology, College of Engineering, Yonsei University</s1><s2>Seoul</s2><s3>KOR</s3><sZ>1 aut.</sZ><sZ>2 aut.</sZ><sZ>3 aut.</sZ><sZ>4 aut.</sZ><sZ>5 aut.</sZ><sZ>8 aut.</sZ></inist:fA14><country>Corée du Sud</country><placeName><settlement type="city">Séoul</settlement><region type="capital">Région capitale de Séoul</region></placeName></affiliation></author><author><name sortKey="Kwang Hee Lee" sort="Kwang Hee Lee" uniqKey="Kwang Hee Lee" last="Kwang Hee Lee">KWANG HEE LEE</name><affiliation wicri:level="3"><inist:fA14 i1="01"><s1>Department of Biotechnology, College of Engineering, Yonsei University</s1><s2>Seoul</s2><s3>KOR</s3><sZ>1 aut.</sZ><sZ>2 aut.</sZ><sZ>3 aut.</sZ><sZ>4 aut.</sZ><sZ>5 aut.</sZ><sZ>8 aut.</sZ></inist:fA14><country>Corée du Sud</country><placeName><settlement type="city">Séoul</settlement><region type="capital">Région capitale de Séoul</region></placeName></affiliation></author><author><name sortKey="Young Ho Byun" sort="Young Ho Byun" uniqKey="Young Ho Byun" last="Young Ho Byun">YOUNG HO BYUN</name><affiliation wicri:level="3"><inist:fA14 i1="01"><s1>Department of Biotechnology, College of Engineering, Yonsei University</s1><s2>Seoul</s2><s3>KOR</s3><sZ>1 aut.</sZ><sZ>2 aut.</sZ><sZ>3 aut.</sZ><sZ>4 aut.</sZ><sZ>5 aut.</sZ><sZ>8 aut.</sZ></inist:fA14><country>Corée du Sud</country><placeName><settlement type="city">Séoul</settlement><region type="capital">Région capitale de Séoul</region></placeName></affiliation></author><author><name sortKey="Ju Hee Park" sort="Ju Hee Park" uniqKey="Ju Hee Park" last="Ju Hee Park">JU HEE PARK</name><affiliation wicri:level="3"><inist:fA14 i1="01"><s1>Department of Biotechnology, College of Engineering, Yonsei University</s1><s2>Seoul</s2><s3>KOR</s3><sZ>1 aut.</sZ><sZ>2 aut.</sZ><sZ>3 aut.</sZ><sZ>4 aut.</sZ><sZ>5 aut.</sZ><sZ>8 aut.</sZ></inist:fA14><country>Corée du Sud</country><placeName><settlement type="city">Séoul</settlement><region type="capital">Région capitale de Séoul</region></placeName></affiliation></author><author><name sortKey="Sung Han Kim" sort="Sung Han Kim" uniqKey="Sung Han Kim" last="Sung Han Kim">SUNG HAN KIM</name><affiliation wicri:level="3"><inist:fA14 i1="02"><s1>Nutrex Technology, Seocho 3-dong</s1><s2>Seocho-gu, Seoul</s2><s3>KOR</s3><sZ>6 aut.</sZ></inist:fA14><country>Corée du Sud</country><placeName><settlement type="city">Séoul</settlement><region type="capital">Région capitale de Séoul</region></placeName></affiliation></author><author><name sortKey="Jae Hong Kim" sort="Jae Hong Kim" uniqKey="Jae Hong Kim" last="Jae Hong Kim">JAE HONG KIM</name><affiliation wicri:level="4"><inist:fA14 i1="03"><s1>College of Veterinary Medicine, Seoul National University</s1><s2>Seoul</s2><s3>KOR</s3><sZ>7 aut.</sZ></inist:fA14><country>Corée du Sud</country><placeName><settlement type="city">Séoul</settlement><region type="capital">Région capitale de Séoul</region></placeName><orgName type="university">Université nationale de Séoul</orgName></affiliation></author><author><name sortKey="Baik Lin Seong" sort="Baik Lin Seong" uniqKey="Baik Lin Seong" last="Baik Lin Seong">BAIK LIN SEONG</name><affiliation wicri:level="3"><inist:fA14 i1="01"><s1>Department of Biotechnology, College of Engineering, Yonsei University</s1><s2>Seoul</s2><s3>KOR</s3><sZ>1 aut.</sZ><sZ>2 aut.</sZ><sZ>3 aut.</sZ><sZ>4 aut.</sZ><sZ>5 aut.</sZ><sZ>8 aut.</sZ></inist:fA14><country>Corée du Sud</country><placeName><settlement type="city">Séoul</settlement><region type="capital">Région capitale de Séoul</region></placeName></affiliation><affiliation wicri:level="3"><inist:fA14 i1="04"><s1>Protheon, Yonsei Engineering Complex, Shinchon-dong</s1><s2>Seodaemungu, Seoul</s2><s3>KOR</s3><sZ>8 aut.</sZ></inist:fA14><country>Corée du Sud</country><placeName><settlement type="city">Séoul</settlement><region type="capital">Région capitale de Séoul</region></placeName></affiliation></author></analytic><series><title level="j" type="main">Antiviral research</title><title level="j" type="abbreviated">Antivir. res.</title><idno type="ISSN">0166-3542</idno><imprint><date when="2007">2007</date></imprint></series></biblStruct></sourceDesc><seriesStmt><title level="j" type="main">Antiviral research</title><title level="j" type="abbreviated">Antivir. res.</title><idno type="ISSN">0166-3542</idno></seriesStmt></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Antiviral</term><term>Avian influenzavirus</term><term>Catechin</term><term>Flavonoid</term><term>Hemagglutinin</term><term>In vitro</term><term>Influenza</term><term>Influenzavirus</term><term>Mechanism of action</term><term>Polyphenol</term><term>Structure activity relation</term></keywords><keywords scheme="Pascal" xml:lang="fr"><term>Relation structure activité</term><term>Grippe</term><term>Flavonoïde</term><term>Polyphénol</term><term>Catéchine</term><term>Influenzavirus</term><term>Hémagglutinine</term><term>Antiviral</term><term>In vitro</term><term>Mécanisme action</term><term>Influenzavirus aviaire</term><term>Catéchine dérivé</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 μM 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><affiliations><list><country><li>Corée du Sud</li></country><region><li>Région capitale de Séoul</li></region><settlement><li>Séoul</li></settlement><orgName><li>Université nationale de Séoul</li></orgName></list><tree><country name="Corée du Sud"><region name="Région capitale de Séoul"><name sortKey="Jae Min Song" sort="Jae Min Song" uniqKey="Jae Min Song" last="Jae Min Song">JAE MIN SONG</name></region><name sortKey="Baik Lin Seong" sort="Baik Lin Seong" uniqKey="Baik Lin Seong" last="Baik Lin Seong">BAIK LIN SEONG</name><name sortKey="Baik Lin Seong" sort="Baik Lin Seong" uniqKey="Baik Lin Seong" last="Baik Lin Seong">BAIK LIN SEONG</name><name sortKey="Jae Hong Kim" sort="Jae Hong Kim" uniqKey="Jae Hong Kim" last="Jae Hong Kim">JAE HONG KIM</name><name sortKey="Ju Hee Park" sort="Ju Hee Park" uniqKey="Ju Hee Park" last="Ju Hee Park">JU HEE PARK</name><name sortKey="Ki Duk Park" sort="Ki Duk Park" uniqKey="Ki Duk Park" last="Ki Duk Park">KI DUK PARK</name><name sortKey="Kwang Hee Lee" sort="Kwang Hee Lee" uniqKey="Kwang Hee Lee" last="Kwang Hee Lee">KWANG HEE LEE</name><name sortKey="Sung Han Kim" sort="Sung Han Kim" uniqKey="Sung Han Kim" last="Sung Han Kim">SUNG HAN KIM</name><name sortKey="Young Ho Byun" sort="Young Ho Byun" uniqKey="Young Ho Byun" last="Young Ho Byun">YOUNG HO BYUN</name></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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