SARS-CoV 3CLpro inhibitory effects of quinone-methide triterpenes from Tripterygium regelii
Identifieur interne : 002923 ( Main/Exploration ); précédent : 002922; suivant : 002924SARS-CoV 3CLpro inhibitory effects of quinone-methide triterpenes from Tripterygium regelii
Auteurs : YOUNG BAE RYU [Corée du Sud] ; Su-Jin Park [Corée du Sud] ; YOUNG MIN KIM [Corée du Sud] ; Ju-Yeon Lee [Corée du Sud] ; WOO DUCK SEO [Corée du Sud] ; JONG SUN CHANG [Corée du Sud] ; KI HUN PARK [Corée du Sud] ; Mun-Chual Rho [Corée du Sud] ; WOO SONG LEE [Corée du Sud]Source :
- Bioorganic & medicinal chemistry letters : (Print) [ 0960-894X ] ; 2010.
Descripteurs français
- Pascal (Inist)
- Virus syndrome respiratoire aigu sévère, Quinométhane, Triterpène, Isolement, Ecorce, Analyse structurale, Cétol, Acide carboxylique, Ester, Cétone, Activité biologique, In vitro, Site fixation, Modèle moléculaire, Energie liaison, Inhibiteur protease, Cysteine endopeptidases, Plante médicinale, Terpénoïde, Celastraceae, Origine végétale, Modélisation, Propriété thermodynamique, Inhibiteur enzyme, Antiviral, Pharmacognosie, Tripterygium, Celastrol, Triptérine, Tingénone, Iguesterin, pristimerin, Tripterygium regelii, Friedélane dérivé.
- Wicri :
- topic : Plante médicinale.
English descriptors
- KwdEn :
- Antiviral, Bark, Binding energy, Binding site, Biological activity, Carboxylic acid, Celastraceae, Cysteine endopeptidases, Enzyme inhibitor, Ester, In vitro, Isolation, Ketol, Ketone, Medicinal plant, Modeling, Molecular model, Pharmacognosy, Plant origin, Protease inhibitor, Quinonemethide, Severe acute respiratory syndrome virus, Structural analysis, Terpenoid, Thermodynamic properties, Triterpene.
Abstract
Quinone-methide triterpenes, celastrol (1), pristimerin (2), tingenone (3), and iguesterin (4) were isolated from Triterygium regelii and dihydrocelastrol (5) was synthesized by hydrogenation under palladium catalyst. Isolated quinone-methide triterpenes (1-4) and 5 were evaluated for SARS-CoV 3CLpro inhibitory activities and showed potent inhibitory activities with IC50 values of 10.3, 5.5, 9.9, and 2.6 μM, respectively, whereas the corresponding 5 having phenol moiety was observed in low activity (IC50 = 21.7 μM). As a result, quinone-methide moiety in A-ring and more hydrophobic E-ring assist to exhibit potent activity. Also, all quinone-methide triterpenes 1-4 have proven to be competitive by the kinetic analysis.
Affiliations:
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Ltd, 377-1 Yeongcheon-ri, Dongtan-myeon</s1><s2>Hwaseong, Gyeonggi-do 445-813</s2><s3>KOR</s3><sZ>4 aut.</sZ></inist:fA14><country>Corée du Sud</country><wicri:noRegion>Hwaseong, Gyeonggi-do 445-813</wicri:noRegion></affiliation></author><author><name sortKey="Woo Duck Seo" sort="Woo Duck Seo" uniqKey="Woo Duck Seo" last="Woo Duck Seo">WOO DUCK SEO</name><affiliation wicri:level="1"><inist:fA14 i1="04"><s1>Department of Functional Crop, NICS, RDA</s1><s2>Miryang 627-803</s2><s3>KOR</s3><sZ>5 aut.</sZ></inist:fA14><country>Corée du Sud</country><wicri:noRegion>Miryang 627-803</wicri:noRegion></affiliation></author><author><name sortKey="Jong Sun Chang" sort="Jong Sun Chang" uniqKey="Jong Sun Chang" last="Jong Sun Chang">JONG SUN CHANG</name><affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Eco-Friendly Biomaterial Research Center, Korea Research Institute of Bioscience and Biotechnology</s1><s2>Jeongeup 580-185</s2><s3>KOR</s3><sZ>1 aut.</sZ><sZ>2 aut.</sZ><sZ>3 aut.</sZ><sZ>6 aut.</sZ><sZ>8 aut.</sZ><sZ>9 aut.</sZ></inist:fA14><country>Corée du Sud</country><wicri:noRegion>Jeongeup 580-185</wicri:noRegion></affiliation></author><author><name sortKey="Ki Hun Park" sort="Ki Hun Park" uniqKey="Ki Hun Park" last="Ki Hun Park">KI HUN PARK</name><affiliation wicri:level="1"><inist:fA14 i1="02"><s1>Division of Applied Life Science (BK 21 Program), EB-NCRC, Graduate School of Gyeongsang National University</s1><s2>Jinju 660-701</s2><s3>KOR</s3><sZ>7 aut.</sZ></inist:fA14><country>Corée du Sud</country><wicri:noRegion>Jinju 660-701</wicri:noRegion></affiliation></author><author><name sortKey="Rho, Mun Chual" sort="Rho, Mun Chual" uniqKey="Rho M" first="Mun-Chual" last="Rho">Mun-Chual Rho</name><affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Eco-Friendly Biomaterial Research Center, Korea Research Institute of Bioscience and Biotechnology</s1><s2>Jeongeup 580-185</s2><s3>KOR</s3><sZ>1 aut.</sZ><sZ>2 aut.</sZ><sZ>3 aut.</sZ><sZ>6 aut.</sZ><sZ>8 aut.</sZ><sZ>9 aut.</sZ></inist:fA14><country>Corée du Sud</country><wicri:noRegion>Jeongeup 580-185</wicri:noRegion></affiliation></author><author><name sortKey="Woo Song Lee" sort="Woo Song Lee" uniqKey="Woo Song Lee" last="Woo Song Lee">WOO SONG LEE</name><affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Eco-Friendly Biomaterial Research Center, Korea Research Institute of Bioscience and Biotechnology</s1><s2>Jeongeup 580-185</s2><s3>KOR</s3><sZ>1 aut.</sZ><sZ>2 aut.</sZ><sZ>3 aut.</sZ><sZ>6 aut.</sZ><sZ>8 aut.</sZ><sZ>9 aut.</sZ></inist:fA14><country>Corée du Sud</country><wicri:noRegion>Jeongeup 580-185</wicri:noRegion></affiliation></author></analytic><series><title level="j" type="main">Bioorganic & medicinal chemistry letters : (Print)</title><title level="j" type="abbreviated">Bioorg. med. chem. lett. : (Print)</title><idno type="ISSN">0960-894X</idno><imprint><date when="2010">2010</date></imprint></series></biblStruct></sourceDesc><seriesStmt><title level="j" type="main">Bioorganic & medicinal chemistry letters : (Print)</title><title level="j" type="abbreviated">Bioorg. med. chem. lett. : (Print)</title><idno type="ISSN">0960-894X</idno></seriesStmt></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Antiviral</term><term>Bark</term><term>Binding energy</term><term>Binding site</term><term>Biological activity</term><term>Carboxylic acid</term><term>Celastraceae</term><term>Cysteine endopeptidases</term><term>Enzyme inhibitor</term><term>Ester</term><term>In vitro</term><term>Isolation</term><term>Ketol</term><term>Ketone</term><term>Medicinal plant</term><term>Modeling</term><term>Molecular model</term><term>Pharmacognosy</term><term>Plant origin</term><term>Protease inhibitor</term><term>Quinonemethide</term><term>Severe acute respiratory syndrome virus</term><term>Structural analysis</term><term>Terpenoid</term><term>Thermodynamic properties</term><term>Triterpene</term></keywords><keywords scheme="Pascal" xml:lang="fr"><term>Virus syndrome respiratoire aigu sévère</term><term>Quinométhane</term><term>Triterpène</term><term>Isolement</term><term>Ecorce</term><term>Analyse structurale</term><term>Cétol</term><term>Acide carboxylique</term><term>Ester</term><term>Cétone</term><term>Activité biologique</term><term>In vitro</term><term>Site fixation</term><term>Modèle moléculaire</term><term>Energie liaison</term><term>Inhibiteur protease</term><term>Cysteine endopeptidases</term><term>Plante médicinale</term><term>Terpénoïde</term><term>Celastraceae</term><term>Origine végétale</term><term>Modélisation</term><term>Propriété thermodynamique</term><term>Inhibiteur enzyme</term><term>Antiviral</term><term>Pharmacognosie</term><term>Tripterygium</term><term>Celastrol</term><term>Triptérine</term><term>Tingénone</term><term>Iguesterin</term><term>pristimerin</term><term>Tripterygium regelii</term><term>Friedélane dérivé</term></keywords><keywords scheme="Wicri" type="topic" xml:lang="fr"><term>Plante médicinale</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">Quinone-methide triterpenes, celastrol (1), pristimerin (2), tingenone (3), and iguesterin (4) were isolated from Triterygium regelii and dihydrocelastrol (5) was synthesized by hydrogenation under palladium catalyst. Isolated quinone-methide triterpenes (1-4) and 5 were evaluated for SARS-CoV 3CL<sup>pro</sup> inhibitory activities and showed potent inhibitory activities with IC<sub>50</sub> values of 10.3, 5.5, 9.9, and 2.6 μM, respectively, whereas the corresponding 5 having phenol moiety was observed in low activity (IC<sub>50</sub> = 21.7 μM). As a result, quinone-methide moiety in A-ring and more hydrophobic E-ring assist to exhibit potent activity. Also, all quinone-methide triterpenes 1-4 have proven to be competitive by the kinetic analysis.</div></front></TEI><affiliations><list><country><li>Corée du Sud</li></country></list><tree><country name="Corée du Sud"><noRegion><name sortKey="Young Bae Ryu" sort="Young Bae Ryu" uniqKey="Young Bae Ryu" last="Young Bae Ryu">YOUNG BAE RYU</name></noRegion><name sortKey="Jong Sun Chang" sort="Jong Sun Chang" uniqKey="Jong Sun Chang" last="Jong Sun Chang">JONG SUN CHANG</name><name sortKey="Ki Hun Park" sort="Ki Hun Park" uniqKey="Ki Hun Park" last="Ki Hun Park">KI HUN PARK</name><name sortKey="Lee, Ju Yeon" sort="Lee, Ju Yeon" uniqKey="Lee J" first="Ju-Yeon" last="Lee">Ju-Yeon Lee</name><name sortKey="Park, Su Jin" sort="Park, Su Jin" uniqKey="Park S" first="Su-Jin" last="Park">Su-Jin Park</name><name sortKey="Rho, Mun Chual" sort="Rho, Mun Chual" uniqKey="Rho M" first="Mun-Chual" last="Rho">Mun-Chual Rho</name><name sortKey="Woo Duck Seo" sort="Woo Duck Seo" uniqKey="Woo Duck Seo" last="Woo Duck Seo">WOO DUCK SEO</name><name sortKey="Woo Song Lee" sort="Woo Song Lee" uniqKey="Woo Song Lee" last="Woo Song Lee">WOO SONG LEE</name><name sortKey="Young Min Kim" sort="Young Min Kim" uniqKey="Young Min Kim" last="Young Min Kim">YOUNG MIN KIM</name></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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