Papain-like protease (PLpro) inhibitory effects of cinnamic amides from Tribulus terrestris fruits.
Identifieur interne : 001604 ( Main/Exploration ); précédent : 001603; suivant : 001605Papain-like protease (PLpro) inhibitory effects of cinnamic amides from Tribulus terrestris fruits.
Auteurs : Yeong Hun Song ; Dae Wook Kim ; Marcus John Curtis-Long ; Heung Joo Yuk ; Yan Wang ; Ningning Zhuang ; Kon Ho Lee ; Kwon Seok Jeon ; Ki Hun ParkSource :
- Biological & pharmaceutical bulletin [ 1347-5215 ] ; 2014.
Descripteurs français
- KwdFr :
- Amides, Cinnamates (isolement et purification), Cinnamates (pharmacologie), Cinnamates (usage thérapeutique), Cinétique, Concentration inhibitrice 50, Cysteine endopeptidases (génétique), Escherichia coli (génétique), Extraits de plantes (), Fruit (), Humains, Inhibiteurs de la cystéine protéinase (isolement et purification), Inhibiteurs de la cystéine protéinase (pharmacologie), Inhibiteurs de la cystéine protéinase (usage thérapeutique), Protéines virales (antagonistes et inhibiteurs), Protéines virales (génétique), Relation dose-effet des médicaments, Relation structure-activité, Structure moléculaire, Syndrome respiratoire aigu sévère (traitement médicamenteux), Syndrome respiratoire aigu sévère (virologie), Tribulus (), Virus du SRAS (enzymologie).
- MESH :
- antagonistes et inhibiteurs : Protéines virales.
- enzymologie : Virus du SRAS.
- génétique : Cysteine endopeptidases, Escherichia coli, Protéines virales.
- isolement et purification : Cinnamates, Inhibiteurs de la cystéine protéinase.
- pharmacologie : Cinnamates, Inhibiteurs de la cystéine protéinase.
- traitement médicamenteux : Syndrome respiratoire aigu sévère.
- usage thérapeutique : Cinnamates, Inhibiteurs de la cystéine protéinase.
- virologie : Syndrome respiratoire aigu sévère.
- Amides, Cinétique, Concentration inhibitrice 50, Extraits de plantes, Fruit, Humains, Relation dose-effet des médicaments, Relation structure-activité, Structure moléculaire, Tribulus.
English descriptors
- KwdEn :
- Amides, Cinnamates (isolation & purification), Cinnamates (pharmacology), Cinnamates (therapeutic use), Cysteine Endopeptidases (genetics), Cysteine Proteinase Inhibitors (isolation & purification), Cysteine Proteinase Inhibitors (pharmacology), Cysteine Proteinase Inhibitors (therapeutic use), Dose-Response Relationship, Drug, Escherichia coli (genetics), Fruit (chemistry), Humans, Inhibitory Concentration 50, Kinetics, Molecular Structure, Plant Extracts (chemistry), SARS Virus (enzymology), Severe Acute Respiratory Syndrome (drug therapy), Severe Acute Respiratory Syndrome (virology), Structure-Activity Relationship, Tribulus (chemistry), Viral Proteins (antagonists & inhibitors), Viral Proteins (genetics).
- MESH :
- chemical , antagonists & inhibitors : Viral Proteins.
- chemical , chemistry : Plant Extracts.
- chemical , genetics : Cysteine Endopeptidases, Viral Proteins.
- chemical , isolation & purification : Cinnamates, Cysteine Proteinase Inhibitors.
- chemical , pharmacology : Cinnamates, Cysteine Proteinase Inhibitors.
- chemical , therapeutic use : Cinnamates, Cysteine Proteinase Inhibitors.
- chemical : Amides.
- chemistry : Fruit, Tribulus.
- drug therapy : Severe Acute Respiratory Syndrome.
- enzymology : SARS Virus.
- genetics : Escherichia coli.
- virology : Severe Acute Respiratory Syndrome.
- Dose-Response Relationship, Drug, Humans, Inhibitory Concentration 50, Kinetics, Molecular Structure, Structure-Activity Relationship.
Abstract
Tribulus terrestris fruits are well known for their usage in pharmaceutical preparations and food supplements. The methanol extract of T. terrestris fruits showed potent inhibition against the papain-like protease (PLpro), an essential proteolylic enzyme for protection to pathogenic virus and bacteria. Subsequent bioactivity-guided fractionation of this extract led to six cinnamic amides (1-6) and ferulic acid (7). Compound 6 emerged as new compound possessing the very rare carbinolamide motif. These compounds (1-7) were evaluated for severe acute respiratory syndrome coronavirus (SARS-CoV) PLpro inhibitory activity to identify their potencies and kinetic behavior. Compounds (1-6) displayed significant inhibitory activity with IC50 values in the range 15.8-70.1 µM. The new cinnamic amide 6 was found to be most potent inhibitor with an IC50 of 15.8 µM. In kinetic studies, all inhibitors exhibited mixed type inhibition. Furthermore, the most active PLpro inhibitors (1-6) were proven to be present in the native fruits in high quantities by HPLC chromatogram and liquid chromatography with diode array detection and electrospray ionization mass spectrometry (LC-DAD-ESI/MS).
DOI: 10.1248/bpb.b14-00026
PubMed: 24882413
Affiliations:
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last="Yuk">Heung Joo Yuk</name></author><author><name sortKey="Wang, Yan" sort="Wang, Yan" uniqKey="Wang Y" first="Yan" last="Wang">Yan Wang</name></author><author><name sortKey="Zhuang, Ningning" sort="Zhuang, Ningning" uniqKey="Zhuang N" first="Ningning" last="Zhuang">Ningning Zhuang</name></author><author><name sortKey="Lee, Kon Ho" sort="Lee, Kon Ho" uniqKey="Lee K" first="Kon Ho" last="Lee">Kon Ho Lee</name></author><author><name sortKey="Jeon, Kwon Seok" sort="Jeon, Kwon Seok" uniqKey="Jeon K" first="Kwon Seok" last="Jeon">Kwon Seok Jeon</name></author><author><name sortKey="Park, Ki Hun" sort="Park, Ki Hun" uniqKey="Park K" first="Ki Hun" last="Park">Ki Hun Park</name></author></titleStmt><publicationStmt><idno type="wicri:source">PubMed</idno><date when="2014">2014</date><idno type="RBID">pubmed:24882413</idno><idno type="pmid">24882413</idno><idno type="doi">10.1248/bpb.b14-00026</idno><idno type="wicri:Area/PubMed/Corpus">000F87</idno><idno type="wicri:explorRef" 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Song</name><affiliation><nlm:affiliation>Division of Applied Life Science (BK21 plus), IALS, Graduate School of GyeongSang National University.</nlm:affiliation><wicri:noCountry code="subField">Graduate School of GyeongSang National University</wicri:noCountry></affiliation></author><author><name sortKey="Kim, Dae Wook" sort="Kim, Dae Wook" uniqKey="Kim D" first="Dae Wook" last="Kim">Dae Wook Kim</name></author><author><name sortKey="Curtis Long, Marcus John" sort="Curtis Long, Marcus John" uniqKey="Curtis Long M" first="Marcus John" last="Curtis-Long">Marcus John Curtis-Long</name></author><author><name sortKey="Yuk, Heung Joo" sort="Yuk, Heung Joo" uniqKey="Yuk H" first="Heung Joo" last="Yuk">Heung Joo Yuk</name></author><author><name sortKey="Wang, Yan" sort="Wang, Yan" uniqKey="Wang Y" first="Yan" last="Wang">Yan Wang</name></author><author><name sortKey="Zhuang, Ningning" sort="Zhuang, Ningning" uniqKey="Zhuang N" first="Ningning" last="Zhuang">Ningning Zhuang</name></author><author><name sortKey="Lee, Kon Ho" sort="Lee, Kon Ho" uniqKey="Lee K" first="Kon Ho" last="Lee">Kon Ho Lee</name></author><author><name sortKey="Jeon, Kwon Seok" sort="Jeon, Kwon Seok" uniqKey="Jeon K" first="Kwon Seok" last="Jeon">Kwon Seok Jeon</name></author><author><name sortKey="Park, Ki Hun" sort="Park, Ki Hun" uniqKey="Park K" first="Ki Hun" last="Park">Ki Hun Park</name></author></analytic><series><title level="j">Biological & pharmaceutical bulletin</title><idno type="eISSN">1347-5215</idno><imprint><date when="2014" type="published">2014</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Amides</term><term>Cinnamates (isolation & purification)</term><term>Cinnamates (pharmacology)</term><term>Cinnamates (therapeutic use)</term><term>Cysteine Endopeptidases (genetics)</term><term>Cysteine Proteinase Inhibitors (isolation & purification)</term><term>Cysteine Proteinase Inhibitors (pharmacology)</term><term>Cysteine Proteinase Inhibitors (therapeutic use)</term><term>Dose-Response Relationship, Drug</term><term>Escherichia coli (genetics)</term><term>Fruit (chemistry)</term><term>Humans</term><term>Inhibitory Concentration 50</term><term>Kinetics</term><term>Molecular Structure</term><term>Plant Extracts (chemistry)</term><term>SARS Virus (enzymology)</term><term>Severe Acute Respiratory Syndrome (drug therapy)</term><term>Severe Acute Respiratory Syndrome (virology)</term><term>Structure-Activity Relationship</term><term>Tribulus (chemistry)</term><term>Viral Proteins (antagonists & inhibitors)</term><term>Viral Proteins (genetics)</term></keywords><keywords scheme="KwdFr" xml:lang="fr"><term>Amides</term><term>Cinnamates (isolement et purification)</term><term>Cinnamates (pharmacologie)</term><term>Cinnamates (usage thérapeutique)</term><term>Cinétique</term><term>Concentration inhibitrice 50</term><term>Cysteine endopeptidases (génétique)</term><term>Escherichia coli (génétique)</term><term>Extraits de plantes ()</term><term>Fruit ()</term><term>Humains</term><term>Inhibiteurs de la cystéine protéinase (isolement et purification)</term><term>Inhibiteurs de la cystéine protéinase (pharmacologie)</term><term>Inhibiteurs de la cystéine protéinase (usage thérapeutique)</term><term>Protéines virales (antagonistes et inhibiteurs)</term><term>Protéines virales (génétique)</term><term>Relation dose-effet des médicaments</term><term>Relation structure-activité</term><term>Structure moléculaire</term><term>Syndrome respiratoire aigu sévère (traitement médicamenteux)</term><term>Syndrome respiratoire aigu sévère (virologie)</term><term>Tribulus ()</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>Plant Extracts</term></keywords><keywords scheme="MESH" type="chemical" qualifier="genetics" xml:lang="en"><term>Cysteine Endopeptidases</term><term>Viral Proteins</term></keywords><keywords scheme="MESH" type="chemical" qualifier="isolation & purification" xml:lang="en"><term>Cinnamates</term><term>Cysteine Proteinase Inhibitors</term></keywords><keywords scheme="MESH" type="chemical" qualifier="pharmacology" xml:lang="en"><term>Cinnamates</term><term>Cysteine Proteinase Inhibitors</term></keywords><keywords scheme="MESH" type="chemical" qualifier="therapeutic use" xml:lang="en"><term>Cinnamates</term><term>Cysteine Proteinase Inhibitors</term></keywords><keywords scheme="MESH" type="chemical" xml:lang="en"><term>Amides</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>Fruit</term><term>Tribulus</term></keywords><keywords scheme="MESH" qualifier="drug therapy" xml:lang="en"><term>Severe Acute Respiratory Syndrome</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="genetics" xml:lang="en"><term>Escherichia coli</term></keywords><keywords scheme="MESH" qualifier="génétique" xml:lang="fr"><term>Cysteine endopeptidases</term><term>Escherichia coli</term><term>Protéines virales</term></keywords><keywords scheme="MESH" qualifier="isolement et purification" xml:lang="fr"><term>Cinnamates</term><term>Inhibiteurs de la cystéine protéinase</term></keywords><keywords scheme="MESH" qualifier="pharmacologie" xml:lang="fr"><term>Cinnamates</term><term>Inhibiteurs de la cystéine protéinase</term></keywords><keywords scheme="MESH" qualifier="traitement médicamenteux" xml:lang="fr"><term>Syndrome respiratoire aigu sévère</term></keywords><keywords scheme="MESH" qualifier="usage thérapeutique" xml:lang="fr"><term>Cinnamates</term><term>Inhibiteurs de la cystéine protéinase</term></keywords><keywords scheme="MESH" qualifier="virologie" xml:lang="fr"><term>Syndrome respiratoire aigu sévère</term></keywords><keywords scheme="MESH" qualifier="virology" xml:lang="en"><term>Severe Acute Respiratory Syndrome</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Dose-Response Relationship, Drug</term><term>Humans</term><term>Inhibitory Concentration 50</term><term>Kinetics</term><term>Molecular Structure</term><term>Structure-Activity Relationship</term></keywords><keywords scheme="MESH" xml:lang="fr"><term>Amides</term><term>Cinétique</term><term>Concentration inhibitrice 50</term><term>Extraits de plantes</term><term>Fruit</term><term>Humains</term><term>Relation dose-effet des médicaments</term><term>Relation structure-activité</term><term>Structure moléculaire</term><term>Tribulus</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">Tribulus terrestris fruits are well known for their usage in pharmaceutical preparations and food supplements. The methanol extract of T. terrestris fruits showed potent inhibition against the papain-like protease (PLpro), an essential proteolylic enzyme for protection to pathogenic virus and bacteria. Subsequent bioactivity-guided fractionation of this extract led to six cinnamic amides (1-6) and ferulic acid (7). Compound 6 emerged as new compound possessing the very rare carbinolamide motif. These compounds (1-7) were evaluated for severe acute respiratory syndrome coronavirus (SARS-CoV) PLpro inhibitory activity to identify their potencies and kinetic behavior. Compounds (1-6) displayed significant inhibitory activity with IC50 values in the range 15.8-70.1 µM. The new cinnamic amide 6 was found to be most potent inhibitor with an IC50 of 15.8 µM. In kinetic studies, all inhibitors exhibited mixed type inhibition. Furthermore, the most active PLpro inhibitors (1-6) were proven to be present in the native fruits in high quantities by HPLC chromatogram and liquid chromatography with diode array detection and electrospray ionization mass spectrometry (LC-DAD-ESI/MS). </div></front></TEI><affiliations><list></list><tree><noCountry><name sortKey="Curtis Long, Marcus John" sort="Curtis Long, Marcus John" uniqKey="Curtis Long M" first="Marcus John" last="Curtis-Long">Marcus John Curtis-Long</name><name sortKey="Jeon, Kwon Seok" sort="Jeon, Kwon Seok" uniqKey="Jeon K" first="Kwon Seok" last="Jeon">Kwon Seok Jeon</name><name sortKey="Kim, Dae Wook" sort="Kim, Dae Wook" uniqKey="Kim D" first="Dae Wook" last="Kim">Dae Wook Kim</name><name sortKey="Lee, Kon Ho" sort="Lee, Kon Ho" uniqKey="Lee K" first="Kon Ho" last="Lee">Kon Ho Lee</name><name sortKey="Park, Ki Hun" sort="Park, Ki Hun" uniqKey="Park K" first="Ki Hun" last="Park">Ki Hun Park</name><name sortKey="Song, Yeong Hun" sort="Song, Yeong Hun" uniqKey="Song Y" first="Yeong Hun" last="Song">Yeong Hun Song</name><name sortKey="Wang, Yan" sort="Wang, Yan" uniqKey="Wang Y" first="Yan" last="Wang">Yan Wang</name><name sortKey="Yuk, Heung Joo" sort="Yuk, Heung Joo" uniqKey="Yuk H" first="Heung Joo" last="Yuk">Heung Joo Yuk</name><name sortKey="Zhuang, Ningning" sort="Zhuang, Ningning" uniqKey="Zhuang N" first="Ningning" last="Zhuang">Ningning Zhuang</name></noCountry></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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