Biflavonoids from Torreya nucifera displaying SARS-CoV 3CL(pro) inhibition.
Identifieur interne : 002577 ( Main/Exploration ); précédent : 002576; suivant : 002578Biflavonoids from Torreya nucifera displaying SARS-CoV 3CL(pro) inhibition.
Auteurs : Young Bae Ryu [Corée du Sud] ; Hyung Jae Jeong ; Jang Hoon Kim ; Young Min Kim ; Ji-Young Park ; Doman Kim ; Thi Thanh Hanh Nguyen ; Su-Jin Park ; Jong Sun Chang ; Ki Hun Park ; Mun-Chual Rho ; Woo Song LeeSource :
- Bioorganic & medicinal chemistry [ 1464-3391 ] ; 2010.
Descripteurs français
- KwdFr :
- Apigénine (), Apigénine (pharmacologie), Biflavonoïdes (), Biflavonoïdes (isolement et purification), Biflavonoïdes (pharmacologie), Cysteine endopeptidases (métabolisme), Domaine catalytique, Feuilles de plante (), Inhibiteurs de protéases (), Inhibiteurs de protéases (isolement et purification), Inhibiteurs de protéases (pharmacologie), Lutéoline (), Lutéoline (pharmacologie), Protéines virales (antagonistes et inhibiteurs), Protéines virales (métabolisme), Quercétine (), Quercétine (pharmacologie), Relation structure-activité, Simulation numérique, Sites de fixation, Taxaceae (), Transfert d'énergie par résonance de fluorescence, Virus du SRAS (enzymologie).
- MESH :
- antagonistes et inhibiteurs : Protéines virales.
- enzymologie : Virus du SRAS.
- isolement et purification : Biflavonoïdes, Inhibiteurs de protéases.
- métabolisme : Cysteine endopeptidases, Protéines virales.
- pharmacologie : Apigénine, Biflavonoïdes, Inhibiteurs de protéases, Lutéoline, Quercétine.
- Apigénine, Biflavonoïdes, Domaine catalytique, Feuilles de plante, Inhibiteurs de protéases, Lutéoline, Quercétine, Relation structure-activité, Simulation numérique, Sites de fixation, Taxaceae, Transfert d'énergie par résonance de fluorescence.
English descriptors
- KwdEn :
- Apigenin (chemistry), Apigenin (pharmacology), Biflavonoids (chemistry), Biflavonoids (isolation & purification), Biflavonoids (pharmacology), Binding Sites, Catalytic Domain, Computer Simulation, Cysteine Endopeptidases (metabolism), Fluorescence Resonance Energy Transfer, Luteolin (chemistry), Luteolin (pharmacology), Plant Leaves (chemistry), Protease Inhibitors (chemistry), Protease Inhibitors (isolation & purification), Protease Inhibitors (pharmacology), Quercetin (chemistry), Quercetin (pharmacology), SARS Virus (enzymology), Structure-Activity Relationship, Taxaceae (chemistry), Viral Proteins (antagonists & inhibitors), Viral Proteins (metabolism).
- MESH :
- chemical , antagonists & inhibitors : Viral Proteins.
- chemical , chemistry : Apigenin, Biflavonoids, Luteolin, Protease Inhibitors, Quercetin.
- chemical , isolation & purification : Biflavonoids, Protease Inhibitors.
- chemical , metabolism : Cysteine Endopeptidases, Viral Proteins.
- chemical , pharmacology : Apigenin, Biflavonoids, Luteolin, Protease Inhibitors, Quercetin.
- chemistry : Plant Leaves, Taxaceae.
- enzymology : SARS Virus.
- Binding Sites, Catalytic Domain, Computer Simulation, Fluorescence Resonance Energy Transfer, Structure-Activity Relationship.
Abstract
As part of our search for botanical sources of SARS-CoV 3CL(pro) inhibitors, we selected Torreya nucifera, which is traditionally used as a medicinal plant in Asia. The ethanol extract of T. nucifera leaves exhibited good SARS-CoV 3CL(pro) inhibitory activity (62% at 100μg/mL). Following bioactivity-guided fractionation, eight diterpenoids (1-8) and four biflavonoids (9-12) were isolated and evaluated for SARS-CoV 3CL(pro) inhibition using fluorescence resonance energy transfer analysis. Of these compounds, the biflavone amentoflavone (9) (IC(50)=8.3μM) showed most potent 3CL(pro) inhibitory effect. Three additional authentic flavones (apigenin, luteolin and quercetin) were tested to establish the basic structure-activity relationship of biflavones. Apigenin, luteolin, and quercetin inhibited 3CL(pro) activity with IC(50) values of 280.8, 20.2, and 23.8μM, respectively. Values of binding energy obtained in a molecular docking study supported the results of enzymatic assays. More potent activity appeared to be associated with the presence of an apigenin moiety at position C-3' of flavones, as biflavone had an effect on 3CL(pro) inhibitory activity.
DOI: 10.1016/j.bmc.2010.09.035
PubMed: 20934345
Affiliations:
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Bioscience and Biotechnology, Jeongeup 580-185</wicri:regionArea><wicri:noRegion>Jeongeup 580-185</wicri:noRegion></affiliation></author><author><name sortKey="Jeong, Hyung Jae" sort="Jeong, Hyung Jae" uniqKey="Jeong H" first="Hyung Jae" last="Jeong">Hyung Jae Jeong</name></author><author><name sortKey="Kim, Jang Hoon" sort="Kim, Jang Hoon" uniqKey="Kim J" first="Jang Hoon" last="Kim">Jang Hoon Kim</name></author><author><name sortKey="Kim, Young Min" sort="Kim, Young Min" uniqKey="Kim Y" first="Young Min" last="Kim">Young Min Kim</name></author><author><name sortKey="Park, Ji Young" sort="Park, Ji Young" uniqKey="Park J" first="Ji-Young" last="Park">Ji-Young Park</name></author><author><name sortKey="Kim, Doman" sort="Kim, Doman" uniqKey="Kim D" first="Doman" last="Kim">Doman Kim</name></author><author><name sortKey="Nguyen, Thi Thanh Hanh" sort="Nguyen, Thi Thanh Hanh" uniqKey="Nguyen T" first="Thi Thanh Hanh" last="Nguyen">Thi Thanh Hanh Nguyen</name></author><author><name 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(pharmacologie)</term><term>Biflavonoïdes ()</term><term>Biflavonoïdes (isolement et purification)</term><term>Biflavonoïdes (pharmacologie)</term><term>Cysteine endopeptidases (métabolisme)</term><term>Domaine catalytique</term><term>Feuilles de plante ()</term><term>Inhibiteurs de protéases ()</term><term>Inhibiteurs de protéases (isolement et purification)</term><term>Inhibiteurs de protéases (pharmacologie)</term><term>Lutéoline ()</term><term>Lutéoline (pharmacologie)</term><term>Protéines virales (antagonistes et inhibiteurs)</term><term>Protéines virales (métabolisme)</term><term>Quercétine ()</term><term>Quercétine (pharmacologie)</term><term>Relation structure-activité</term><term>Simulation numérique</term><term>Sites de fixation</term><term>Taxaceae ()</term><term>Transfert d'énergie par résonance de fluorescence</term><term>Virus du SRAS (enzymologie)</term></keywords><keywords scheme="MESH" type="chemical" qualifier="antagonists & inhibitors" xml:lang="en"><term>Viral Proteins</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Apigenin</term><term>Biflavonoids</term><term>Luteolin</term><term>Protease Inhibitors</term><term>Quercetin</term></keywords><keywords scheme="MESH" type="chemical" qualifier="isolation & purification" xml:lang="en"><term>Biflavonoids</term><term>Protease Inhibitors</term></keywords><keywords scheme="MESH" type="chemical" qualifier="metabolism" xml:lang="en"><term>Cysteine Endopeptidases</term><term>Viral Proteins</term></keywords><keywords scheme="MESH" type="chemical" qualifier="pharmacology" xml:lang="en"><term>Apigenin</term><term>Biflavonoids</term><term>Luteolin</term><term>Protease Inhibitors</term><term>Quercetin</term></keywords><keywords scheme="MESH" qualifier="antagonistes et inhibiteurs" xml:lang="fr"><term>Protéines virales</term></keywords><keywords scheme="MESH" qualifier="chemistry" xml:lang="en"><term>Plant Leaves</term><term>Taxaceae</term></keywords><keywords scheme="MESH" qualifier="enzymologie" xml:lang="fr"><term>Virus du SRAS</term></keywords><keywords scheme="MESH" qualifier="enzymology" xml:lang="en"><term>SARS Virus</term></keywords><keywords scheme="MESH" qualifier="isolement et purification" xml:lang="fr"><term>Biflavonoïdes</term><term>Inhibiteurs de protéases</term></keywords><keywords scheme="MESH" qualifier="métabolisme" xml:lang="fr"><term>Cysteine endopeptidases</term><term>Protéines virales</term></keywords><keywords scheme="MESH" qualifier="pharmacologie" xml:lang="fr"><term>Apigénine</term><term>Biflavonoïdes</term><term>Inhibiteurs de protéases</term><term>Lutéoline</term><term>Quercétine</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Binding Sites</term><term>Catalytic Domain</term><term>Computer Simulation</term><term>Fluorescence Resonance Energy Transfer</term><term>Structure-Activity Relationship</term></keywords><keywords scheme="MESH" xml:lang="fr"><term>Apigénine</term><term>Biflavonoïdes</term><term>Domaine catalytique</term><term>Feuilles de plante</term><term>Inhibiteurs de protéases</term><term>Lutéoline</term><term>Quercétine</term><term>Relation structure-activité</term><term>Simulation numérique</term><term>Sites de fixation</term><term>Taxaceae</term><term>Transfert d'énergie par résonance de fluorescence</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">As part of our search for botanical sources of SARS-CoV 3CL(pro) inhibitors, we selected Torreya nucifera, which is traditionally used as a medicinal plant in Asia. The ethanol extract of T. nucifera leaves exhibited good SARS-CoV 3CL(pro) inhibitory activity (62% at 100μg/mL). Following bioactivity-guided fractionation, eight diterpenoids (1-8) and four biflavonoids (9-12) were isolated and evaluated for SARS-CoV 3CL(pro) inhibition using fluorescence resonance energy transfer analysis. Of these compounds, the biflavone amentoflavone (9) (IC(50)=8.3μM) showed most potent 3CL(pro) inhibitory effect. Three additional authentic flavones (apigenin, luteolin and quercetin) were tested to establish the basic structure-activity relationship of biflavones. Apigenin, luteolin, and quercetin inhibited 3CL(pro) activity with IC(50) values of 280.8, 20.2, and 23.8μM, respectively. Values of binding energy obtained in a molecular docking study supported the results of enzymatic assays. More potent activity appeared to be associated with the presence of an apigenin moiety at position C-3' of flavones, as biflavone had an effect on 3CL(pro) inhibitory activity.</div></front></TEI><affiliations><list><country><li>Corée du Sud</li></country></list><tree><noCountry><name sortKey="Chang, Jong Sun" sort="Chang, Jong Sun" uniqKey="Chang J" first="Jong Sun" last="Chang">Jong Sun Chang</name><name sortKey="Jeong, Hyung Jae" sort="Jeong, Hyung Jae" uniqKey="Jeong H" first="Hyung Jae" last="Jeong">Hyung Jae Jeong</name><name sortKey="Kim, Doman" sort="Kim, Doman" uniqKey="Kim D" first="Doman" last="Kim">Doman Kim</name><name sortKey="Kim, Jang Hoon" sort="Kim, Jang Hoon" uniqKey="Kim J" first="Jang Hoon" last="Kim">Jang Hoon Kim</name><name sortKey="Kim, Young Min" sort="Kim, Young Min" uniqKey="Kim Y" first="Young Min" last="Kim">Young Min Kim</name><name sortKey="Lee, Woo Song" sort="Lee, Woo Song" uniqKey="Lee W" first="Woo Song" last="Lee">Woo Song Lee</name><name sortKey="Nguyen, Thi Thanh Hanh" sort="Nguyen, Thi Thanh Hanh" uniqKey="Nguyen T" first="Thi Thanh Hanh" last="Nguyen">Thi Thanh Hanh Nguyen</name><name sortKey="Park, Ji Young" sort="Park, Ji Young" uniqKey="Park J" first="Ji-Young" last="Park">Ji-Young Park</name><name sortKey="Park, Ki Hun" sort="Park, Ki Hun" uniqKey="Park K" first="Ki Hun" last="Park">Ki Hun Park</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></noCountry><country name="Corée du Sud"><noRegion><name sortKey="Ryu, Young Bae" sort="Ryu, Young Bae" uniqKey="Ryu Y" first="Young Bae" last="Ryu">Young Bae Ryu</name></noRegion></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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