Papain-like protease (PLpro) inhibitory effects of cinnamic amides from Tribulus terrestris fruits.
Identifieur interne : 002897 ( Ncbi/Curation ); précédent : 002896; suivant : 002898Papain-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
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Yeong Hun Song<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>
Le document en format XML
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<series><title level="j">Biological & pharmaceutical bulletin</title>
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<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>
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<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>
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<keywords scheme="MESH" type="chemical" qualifier="antagonists & inhibitors" xml:lang="en"><term>Viral Proteins</term>
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<keywords scheme="MESH" type="chemical" qualifier="genetics" xml:lang="en"><term>Cysteine Endopeptidases</term>
<term>Viral Proteins</term>
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<term>Cysteine Proteinase Inhibitors</term>
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<keywords scheme="MESH" type="chemical" qualifier="pharmacology" xml:lang="en"><term>Cinnamates</term>
<term>Cysteine Proteinase Inhibitors</term>
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<term>Cysteine Proteinase Inhibitors</term>
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<keywords scheme="MESH" qualifier="antagonistes et inhibiteurs" xml:lang="fr"><term>Protéines virales</term>
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<term>Tribulus</term>
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<keywords scheme="MESH" qualifier="drug therapy" xml:lang="en"><term>Severe Acute Respiratory Syndrome</term>
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<term>Escherichia coli</term>
<term>Protéines virales</term>
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<term>Inhibiteurs de la cystéine protéinase</term>
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<term>Inhibiteurs de la cystéine protéinase</term>
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<term>Inhibiteurs de la cystéine protéinase</term>
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<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>
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<term>Cinétique</term>
<term>Concentration inhibitrice 50</term>
<term>Extraits de plantes</term>
<term>Fruit</term>
<term>Humains</term>
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<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>
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