Papain-like protease (PLpro) inhibitory effects of cinnamic amides from Tribulus terrestris fruits.
Identifieur interne : 000F87 ( PubMed/Corpus ); précédent : 000F86; suivant : 000F88Papain-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.
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
Links to Exploration step
pubmed:24882413Le document en format XML
<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">Papain-like protease (PLpro) inhibitory effects of cinnamic amides from Tribulus terrestris fruits.</title><author><name sortKey="Song, Yeong Hun" sort="Song, Yeong Hun" uniqKey="Song Y" first="Yeong Hun" last="Song">Yeong Hun Song</name><affiliation><nlm:affiliation>Division of Applied Life Science (BK21 plus), IALS, Graduate School of GyeongSang National University.</nlm:affiliation></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></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" wicri:stream="PubMed" wicri:step="Corpus" 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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="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="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="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="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></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><pubmed><MedlineCitation Status="MEDLINE" Owner="NLM"><PMID Version="1">24882413</PMID><DateCompleted><Year>2015</Year><Month>01</Month><Day>20</Day></DateCompleted><DateRevised><Year>2020</Year><Month>03</Month><Day>25</Day></DateRevised><Article PubModel="Print"><Journal><ISSN IssnType="Electronic">1347-5215</ISSN><JournalIssue CitedMedium="Internet"><Volume>37</Volume><Issue>6</Issue><PubDate><Year>2014</Year></PubDate></JournalIssue><Title>Biological & pharmaceutical bulletin</Title><ISOAbbreviation>Biol. Pharm. Bull.</ISOAbbreviation></Journal><ArticleTitle>Papain-like protease (PLpro) inhibitory effects of cinnamic amides from Tribulus terrestris fruits.</ArticleTitle><Pagination><MedlinePgn>1021-8</MedlinePgn></Pagination><Abstract><AbstractText>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). </AbstractText></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Song</LastName><ForeName>Yeong Hun</ForeName><Initials>YH</Initials><AffiliationInfo><Affiliation>Division of Applied Life Science (BK21 plus), IALS, Graduate School of GyeongSang National University.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Kim</LastName><ForeName>Dae Wook</ForeName><Initials>DW</Initials></Author><Author ValidYN="Y"><LastName>Curtis-Long</LastName><ForeName>Marcus John</ForeName><Initials>MJ</Initials></Author><Author ValidYN="Y"><LastName>Yuk</LastName><ForeName>Heung Joo</ForeName><Initials>HJ</Initials></Author><Author ValidYN="Y"><LastName>Wang</LastName><ForeName>Yan</ForeName><Initials>Y</Initials></Author><Author ValidYN="Y"><LastName>Zhuang</LastName><ForeName>Ningning</ForeName><Initials>N</Initials></Author><Author ValidYN="Y"><LastName>Lee</LastName><ForeName>Kon Ho</ForeName><Initials>KH</Initials></Author><Author ValidYN="Y"><LastName>Jeon</LastName><ForeName>Kwon Seok</ForeName><Initials>KS</Initials></Author><Author ValidYN="Y"><LastName>Park</LastName><ForeName>Ki Hun</ForeName><Initials>KH</Initials></Author></AuthorList><Language>eng</Language><GrantList CompleteYN="Y"><Grant><Agency>Howard Hughes Medical Institute</Agency><Country>United States</Country></Grant></GrantList><PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType><PublicationType UI="D013485">Research Support, Non-U.S. Gov't</PublicationType></PublicationTypeList></Article><MedlineJournalInfo><Country>Japan</Country><MedlineTA>Biol Pharm Bull</MedlineTA><NlmUniqueID>9311984</NlmUniqueID><ISSNLinking>0918-6158</ISSNLinking></MedlineJournalInfo><ChemicalList><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D000577">Amides</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D002934">Cinnamates</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D015853">Cysteine Proteinase Inhibitors</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D010936">Plant Extracts</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D014764">Viral Proteins</NameOfSubstance></Chemical><Chemical><RegistryNumber>EC 3.4.22.-</RegistryNumber><NameOfSubstance UI="C099456">3C-like proteinase, Coronavirus</NameOfSubstance></Chemical><Chemical><RegistryNumber>EC 3.4.22.-</RegistryNumber><NameOfSubstance UI="D003546">Cysteine Endopeptidases</NameOfSubstance></Chemical></ChemicalList><CitationSubset>IM</CitationSubset><MeshHeadingList><MeshHeading><DescriptorName UI="D000577" MajorTopicYN="N">Amides</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D002934" MajorTopicYN="N">Cinnamates</DescriptorName><QualifierName UI="Q000302" MajorTopicYN="N">isolation & purification</QualifierName><QualifierName UI="Q000494" MajorTopicYN="Y">pharmacology</QualifierName><QualifierName UI="Q000627" MajorTopicYN="N">therapeutic use</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D003546" MajorTopicYN="N">Cysteine Endopeptidases</DescriptorName><QualifierName UI="Q000235" MajorTopicYN="N">genetics</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D015853" MajorTopicYN="N">Cysteine Proteinase Inhibitors</DescriptorName><QualifierName UI="Q000302" MajorTopicYN="N">isolation & purification</QualifierName><QualifierName UI="Q000494" MajorTopicYN="Y">pharmacology</QualifierName><QualifierName UI="Q000627" MajorTopicYN="N">therapeutic use</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D004305" MajorTopicYN="N">Dose-Response Relationship, Drug</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D004926" MajorTopicYN="N">Escherichia coli</DescriptorName><QualifierName UI="Q000235" MajorTopicYN="N">genetics</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D005638" MajorTopicYN="N">Fruit</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D006801" MajorTopicYN="N">Humans</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D020128" MajorTopicYN="N">Inhibitory Concentration 50</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D007700" MajorTopicYN="N">Kinetics</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D015394" MajorTopicYN="N">Molecular Structure</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D010936" MajorTopicYN="N">Plant Extracts</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="Y">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D045473" MajorTopicYN="N">SARS Virus</DescriptorName><QualifierName UI="Q000201" MajorTopicYN="N">enzymology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D045169" MajorTopicYN="N">Severe Acute Respiratory Syndrome</DescriptorName><QualifierName UI="Q000188" MajorTopicYN="N">drug therapy</QualifierName><QualifierName UI="Q000821" MajorTopicYN="N">virology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D013329" MajorTopicYN="N">Structure-Activity Relationship</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D032444" MajorTopicYN="N">Tribulus</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="Y">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D014764" MajorTopicYN="N">Viral Proteins</DescriptorName><QualifierName UI="Q000037" MajorTopicYN="Y">antagonists & inhibitors</QualifierName><QualifierName UI="Q000235" MajorTopicYN="N">genetics</QualifierName></MeshHeading></MeshHeadingList></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="entrez"><Year>2014</Year><Month>6</Month><Day>3</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="pubmed"><Year>2014</Year><Month>6</Month><Day>3</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="medline"><Year>2015</Year><Month>1</Month><Day>21</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate></History><PublicationStatus>ppublish</PublicationStatus><ArticleIdList><ArticleId IdType="pubmed">24882413</ArticleId><ArticleId IdType="pii">DN/JST.JSTAGE/bpb/b14-00026</ArticleId><ArticleId IdType="doi">10.1248/bpb.b14-00026</ArticleId></ArticleIdList></PubmedData></pubmed></record>Pour manipuler ce document sous Unix (Dilib)
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