In vitro anti-influenza virus activities of a new lignan glycoside from the latex of Calotropis gigantea
A new lignan glycoside, (+)-pinoresinol 4-O-[6″-O-vanilloyl]-β-D-glucopyranoside (1) and two known phenolic compounds, 6'-O-vanilloyltachioside (2) and 6'-O-vanilloylisotachioside (3) were isolated from the latex of Calotropis gigantea (Asclepiadaceae). The structure of the new compound wa...
Gespeichert in:
Veröffentlicht in: | PloS one 2014-08, Vol.9 (8), p.e104544-e104544 |
---|---|
Hauptverfasser: | , , , , , , , , |
Format: | Artikel |
Sprache: | eng |
Schlagworte: | |
Online-Zugang: | Volltext |
Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
container_end_page | e104544 |
---|---|
container_issue | 8 |
container_start_page | e104544 |
container_title | PloS one |
container_volume | 9 |
creator | Parhira, Supawadee Yang, Zi-Feng Zhu, Guo-Yuan Chen, Qiao-Lian Zhou, Bei-Xian Wang, Yu-Tao Liu, Liang Bai, Li-Ping Jiang, Zhi-Hong |
description | A new lignan glycoside, (+)-pinoresinol 4-O-[6″-O-vanilloyl]-β-D-glucopyranoside (1) and two known phenolic compounds, 6'-O-vanilloyltachioside (2) and 6'-O-vanilloylisotachioside (3) were isolated from the latex of Calotropis gigantea (Asclepiadaceae). The structure of the new compound was elucidated by using spectroscopic and chemical methods. Three isolates (1-3) and one authentic compound, (+)-pinoresinol 4-O-β-D-glucopyranoside, were screened for A/PR/8/34 (H1N1) inhibitory activity by cytopathic effect (CPE) inhibition assay on MDCK cells. Compound 1 showed inhibitory activity against A/PR/8/34 (H1N1). In sharp contrast, the other three compounds (2, 3 and (+)-pinoresinol 4-O-β-D-glucopyranoside) did not show such activity. An analysis of structure-activity relationship between 1 and (+)-pinoresinol 4-O-β-D-glucopyranoside revealed that the presence of a vanilloyl group in the sugar moiety of 1 is crucial for its anti-influenza virus activity. Compound 1 was further evaluated for in vitro inhibitory activities against a panel of human and avian influenza viruses by CPE inhibition assay. It showed inhibitory effect against human influenza viruses in both subtypes A and B (IC50 values around 13.4-39.8 µM with SI values of 3.7-11.4), while had no effect on avian influenza viruses. Its antiviral activity against human influenza viruses subtype A was further confirmed by plaque reduction assay. The time course assay indicated that 1 exerts its antiviral activity at the early stage of viral replication. A mechanistic study showed that 1 efficiently inhibited influenza virus-induced activation of NF-κB pathway in a dose-dependent manner, but had no effect on virus-induced activation of Raf/MEK/ERK pathway. Further studies demonstrated that nuclear translocation of transcription factor NF-κB induced by influenza virus was significantly blocked by 1, meanwhile, nuclear export of viral ribonucleoproteins was also effectively inhibited. These findings suggest that this new lignan glycoside from Calotropis gigantea, may have therapeutic potential in influenza virus infection through inhibition of NF-κB pathway and viral ribonucleoproteins nuclear export. |
doi_str_mv | 10.1371/journal.pone.0104544 |
format | Article |
fullrecord | <record><control><sourceid>gale_plos_</sourceid><recordid>TN_cdi_plos_journals_2014077704</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><galeid>A418708540</galeid><doaj_id>oai_doaj_org_article_eb092fe8e33a456db524a746680c2d12</doaj_id><sourcerecordid>A418708540</sourcerecordid><originalsourceid>FETCH-LOGICAL-c758t-c37c1b1cbcb2f214b4798a08aaf337ffca71421e6619f249f95c03ecfa8c06443</originalsourceid><addsrcrecordid>eNqNk1trFDEUxwdRbK1-A9GAIPqwa25zexHK4mWhUPD2Gs5kktks2WSbzFTrpzfjTsuO9EHykHDyO_9Dzj8ny54TvCSsJO-2fggO7HLvnVpignnO-YPslNSMLgqK2cOj80n2JMYtxjmriuJxdkJzginG-DTbrB26Nn3wCFxvFsZpOyj3G1IwDBGB7E26NioirxEgp34iazoHDnX2RvpoWoV08DvUbxSy0KtfI7gC65Pm3kTUmS4pK3iaPdJgo3o27WfZ948fvq0-Ly4uP61X5xcLWeZVv5CslKQhspEN1ZTwhpd1BbgC0IyVWksoCadEFQWpNeW1rnOJmZIaKokLztlZ9vKgu7c-iqlJUVBMOC7LEo_E-kC0HrZiH8wOwo3wYMTfgA-dgNAbaZVQDa6pVpViDHhetE1OOZS8KCosaUto0no_VRuanWqlcn0AOxOd3zizEZ2_FpzQnBKSBN5MAsFfDSr2YmeiVNaCU36IguQ5TW4XxVjr1T_o_a-bqA7SA5KfyQiQo6g456QqcZVznKjlPVRardoZmX6UNik-S3g7S0hM8rrvYIhRrL9--X_28secfX3EbhTYfhO9HXrjXZyD_ADK4GMMSt81mWAxDsRtN8Q4EGIaiJT24tigu6TbCWB_AF9fBa4</addsrcrecordid><sourcetype>Open Website</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2014077704</pqid></control><display><type>article</type><title>In vitro anti-influenza virus activities of a new lignan glycoside from the latex of Calotropis gigantea</title><source>MEDLINE</source><source>DOAJ Directory of Open Access Journals</source><source>Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals</source><source>PubMed Central</source><source>Free Full-Text Journals in Chemistry</source><source>Public Library of Science (PLoS)</source><creator>Parhira, Supawadee ; Yang, Zi-Feng ; Zhu, Guo-Yuan ; Chen, Qiao-Lian ; Zhou, Bei-Xian ; Wang, Yu-Tao ; Liu, Liang ; Bai, Li-Ping ; Jiang, Zhi-Hong</creator><contributor>Jin, Dong-Yan</contributor><creatorcontrib>Parhira, Supawadee ; Yang, Zi-Feng ; Zhu, Guo-Yuan ; Chen, Qiao-Lian ; Zhou, Bei-Xian ; Wang, Yu-Tao ; Liu, Liang ; Bai, Li-Ping ; Jiang, Zhi-Hong ; Jin, Dong-Yan</creatorcontrib><description>A new lignan glycoside, (+)-pinoresinol 4-O-[6″-O-vanilloyl]-β-D-glucopyranoside (1) and two known phenolic compounds, 6'-O-vanilloyltachioside (2) and 6'-O-vanilloylisotachioside (3) were isolated from the latex of Calotropis gigantea (Asclepiadaceae). The structure of the new compound was elucidated by using spectroscopic and chemical methods. Three isolates (1-3) and one authentic compound, (+)-pinoresinol 4-O-β-D-glucopyranoside, were screened for A/PR/8/34 (H1N1) inhibitory activity by cytopathic effect (CPE) inhibition assay on MDCK cells. Compound 1 showed inhibitory activity against A/PR/8/34 (H1N1). In sharp contrast, the other three compounds (2, 3 and (+)-pinoresinol 4-O-β-D-glucopyranoside) did not show such activity. An analysis of structure-activity relationship between 1 and (+)-pinoresinol 4-O-β-D-glucopyranoside revealed that the presence of a vanilloyl group in the sugar moiety of 1 is crucial for its anti-influenza virus activity. Compound 1 was further evaluated for in vitro inhibitory activities against a panel of human and avian influenza viruses by CPE inhibition assay. It showed inhibitory effect against human influenza viruses in both subtypes A and B (IC50 values around 13.4-39.8 µM with SI values of 3.7-11.4), while had no effect on avian influenza viruses. Its antiviral activity against human influenza viruses subtype A was further confirmed by plaque reduction assay. The time course assay indicated that 1 exerts its antiviral activity at the early stage of viral replication. A mechanistic study showed that 1 efficiently inhibited influenza virus-induced activation of NF-κB pathway in a dose-dependent manner, but had no effect on virus-induced activation of Raf/MEK/ERK pathway. Further studies demonstrated that nuclear translocation of transcription factor NF-κB induced by influenza virus was significantly blocked by 1, meanwhile, nuclear export of viral ribonucleoproteins was also effectively inhibited. These findings suggest that this new lignan glycoside from Calotropis gigantea, may have therapeutic potential in influenza virus infection through inhibition of NF-κB pathway and viral ribonucleoproteins nuclear export.</description><identifier>ISSN: 1932-6203</identifier><identifier>EISSN: 1932-6203</identifier><identifier>DOI: 10.1371/journal.pone.0104544</identifier><identifier>PMID: 25102000</identifier><language>eng</language><publisher>United States: Public Library of Science</publisher><subject>Activation ; Analysis ; Animals ; Antiviral activity ; Antiviral Agents - chemistry ; Antiviral Agents - isolation & purification ; Antiviral Agents - pharmacology ; Assaying ; Avian flu ; Biology and Life Sciences ; Calotropis gigantea ; Chromatography ; Dogs ; Embryophyta - chemistry ; Exports ; Fourier transforms ; Gene expression ; Glycosides ; Glycosides - chemistry ; Glycosides - isolation & purification ; Glycosides - pharmacology ; Health aspects ; Hospitals ; Humans ; Infections ; Influenza ; Influenza A Virus, H1N1 Subtype - physiology ; Influenza viruses ; Inhibition ; Kinases ; Laboratories ; Latex ; Latex - chemistry ; Lignans - chemistry ; Lignans - isolation & purification ; Lignans - pharmacology ; Madin Darby Canine Kidney Cells ; Medicine ; Metabolic pathways ; NF-κB protein ; Nuclear transport ; Orthomyxoviridae Infections - drug therapy ; Pandemics ; Phenolic compounds ; Phenols ; Physical Sciences ; Quality ; Respiratory diseases ; Ribonucleoproteins ; Science ; Sugar ; Translocation ; Viral infections ; Virus replication ; Virus Replication - drug effects ; Viruses</subject><ispartof>PloS one, 2014-08, Vol.9 (8), p.e104544-e104544</ispartof><rights>COPYRIGHT 2014 Public Library of Science</rights><rights>2014 Parhira et al. This is an open-access article distributed under the terms of the Creative Commons Attribution License: http://creativecommons.org/licenses/by/4.0/ (the “License”), which permits unrestricted use, distribution, and reproduction in any medium, provided the original author and source are credited. Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License.</rights><rights>2014 Parhira et al 2014 Parhira et al</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c758t-c37c1b1cbcb2f214b4798a08aaf337ffca71421e6619f249f95c03ecfa8c06443</citedby><cites>FETCH-LOGICAL-c758t-c37c1b1cbcb2f214b4798a08aaf337ffca71421e6619f249f95c03ecfa8c06443</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC4125211/pdf/$$EPDF$$P50$$Gpubmedcentral$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC4125211/$$EHTML$$P50$$Gpubmedcentral$$Hfree_for_read</linktohtml><link.rule.ids>230,314,723,776,780,860,881,2096,2915,23845,27901,27902,53766,53768,79343,79344</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/25102000$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><contributor>Jin, Dong-Yan</contributor><creatorcontrib>Parhira, Supawadee</creatorcontrib><creatorcontrib>Yang, Zi-Feng</creatorcontrib><creatorcontrib>Zhu, Guo-Yuan</creatorcontrib><creatorcontrib>Chen, Qiao-Lian</creatorcontrib><creatorcontrib>Zhou, Bei-Xian</creatorcontrib><creatorcontrib>Wang, Yu-Tao</creatorcontrib><creatorcontrib>Liu, Liang</creatorcontrib><creatorcontrib>Bai, Li-Ping</creatorcontrib><creatorcontrib>Jiang, Zhi-Hong</creatorcontrib><title>In vitro anti-influenza virus activities of a new lignan glycoside from the latex of Calotropis gigantea</title><title>PloS one</title><addtitle>PLoS One</addtitle><description>A new lignan glycoside, (+)-pinoresinol 4-O-[6″-O-vanilloyl]-β-D-glucopyranoside (1) and two known phenolic compounds, 6'-O-vanilloyltachioside (2) and 6'-O-vanilloylisotachioside (3) were isolated from the latex of Calotropis gigantea (Asclepiadaceae). The structure of the new compound was elucidated by using spectroscopic and chemical methods. Three isolates (1-3) and one authentic compound, (+)-pinoresinol 4-O-β-D-glucopyranoside, were screened for A/PR/8/34 (H1N1) inhibitory activity by cytopathic effect (CPE) inhibition assay on MDCK cells. Compound 1 showed inhibitory activity against A/PR/8/34 (H1N1). In sharp contrast, the other three compounds (2, 3 and (+)-pinoresinol 4-O-β-D-glucopyranoside) did not show such activity. An analysis of structure-activity relationship between 1 and (+)-pinoresinol 4-O-β-D-glucopyranoside revealed that the presence of a vanilloyl group in the sugar moiety of 1 is crucial for its anti-influenza virus activity. Compound 1 was further evaluated for in vitro inhibitory activities against a panel of human and avian influenza viruses by CPE inhibition assay. It showed inhibitory effect against human influenza viruses in both subtypes A and B (IC50 values around 13.4-39.8 µM with SI values of 3.7-11.4), while had no effect on avian influenza viruses. Its antiviral activity against human influenza viruses subtype A was further confirmed by plaque reduction assay. The time course assay indicated that 1 exerts its antiviral activity at the early stage of viral replication. A mechanistic study showed that 1 efficiently inhibited influenza virus-induced activation of NF-κB pathway in a dose-dependent manner, but had no effect on virus-induced activation of Raf/MEK/ERK pathway. Further studies demonstrated that nuclear translocation of transcription factor NF-κB induced by influenza virus was significantly blocked by 1, meanwhile, nuclear export of viral ribonucleoproteins was also effectively inhibited. These findings suggest that this new lignan glycoside from Calotropis gigantea, may have therapeutic potential in influenza virus infection through inhibition of NF-κB pathway and viral ribonucleoproteins nuclear export.</description><subject>Activation</subject><subject>Analysis</subject><subject>Animals</subject><subject>Antiviral activity</subject><subject>Antiviral Agents - chemistry</subject><subject>Antiviral Agents - isolation & purification</subject><subject>Antiviral Agents - pharmacology</subject><subject>Assaying</subject><subject>Avian flu</subject><subject>Biology and Life Sciences</subject><subject>Calotropis gigantea</subject><subject>Chromatography</subject><subject>Dogs</subject><subject>Embryophyta - chemistry</subject><subject>Exports</subject><subject>Fourier transforms</subject><subject>Gene expression</subject><subject>Glycosides</subject><subject>Glycosides - chemistry</subject><subject>Glycosides - isolation & purification</subject><subject>Glycosides - pharmacology</subject><subject>Health aspects</subject><subject>Hospitals</subject><subject>Humans</subject><subject>Infections</subject><subject>Influenza</subject><subject>Influenza A Virus, H1N1 Subtype - physiology</subject><subject>Influenza viruses</subject><subject>Inhibition</subject><subject>Kinases</subject><subject>Laboratories</subject><subject>Latex</subject><subject>Latex - chemistry</subject><subject>Lignans - chemistry</subject><subject>Lignans - isolation & purification</subject><subject>Lignans - pharmacology</subject><subject>Madin Darby Canine Kidney Cells</subject><subject>Medicine</subject><subject>Metabolic pathways</subject><subject>NF-κB protein</subject><subject>Nuclear transport</subject><subject>Orthomyxoviridae Infections - drug therapy</subject><subject>Pandemics</subject><subject>Phenolic compounds</subject><subject>Phenols</subject><subject>Physical Sciences</subject><subject>Quality</subject><subject>Respiratory diseases</subject><subject>Ribonucleoproteins</subject><subject>Science</subject><subject>Sugar</subject><subject>Translocation</subject><subject>Viral infections</subject><subject>Virus replication</subject><subject>Virus Replication - drug effects</subject><subject>Viruses</subject><issn>1932-6203</issn><issn>1932-6203</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><sourceid>BENPR</sourceid><sourceid>DOA</sourceid><recordid>eNqNk1trFDEUxwdRbK1-A9GAIPqwa25zexHK4mWhUPD2Gs5kktks2WSbzFTrpzfjTsuO9EHykHDyO_9Dzj8ny54TvCSsJO-2fggO7HLvnVpignnO-YPslNSMLgqK2cOj80n2JMYtxjmriuJxdkJzginG-DTbrB26Nn3wCFxvFsZpOyj3G1IwDBGB7E26NioirxEgp34iazoHDnX2RvpoWoV08DvUbxSy0KtfI7gC65Pm3kTUmS4pK3iaPdJgo3o27WfZ948fvq0-Ly4uP61X5xcLWeZVv5CslKQhspEN1ZTwhpd1BbgC0IyVWksoCadEFQWpNeW1rnOJmZIaKokLztlZ9vKgu7c-iqlJUVBMOC7LEo_E-kC0HrZiH8wOwo3wYMTfgA-dgNAbaZVQDa6pVpViDHhetE1OOZS8KCosaUto0no_VRuanWqlcn0AOxOd3zizEZ2_FpzQnBKSBN5MAsFfDSr2YmeiVNaCU36IguQ5TW4XxVjr1T_o_a-bqA7SA5KfyQiQo6g456QqcZVznKjlPVRardoZmX6UNik-S3g7S0hM8rrvYIhRrL9--X_28secfX3EbhTYfhO9HXrjXZyD_ADK4GMMSt81mWAxDsRtN8Q4EGIaiJT24tigu6TbCWB_AF9fBa4</recordid><startdate>20140807</startdate><enddate>20140807</enddate><creator>Parhira, Supawadee</creator><creator>Yang, Zi-Feng</creator><creator>Zhu, Guo-Yuan</creator><creator>Chen, Qiao-Lian</creator><creator>Zhou, Bei-Xian</creator><creator>Wang, Yu-Tao</creator><creator>Liu, Liang</creator><creator>Bai, Li-Ping</creator><creator>Jiang, Zhi-Hong</creator><general>Public Library of Science</general><general>Public Library of Science (PLoS)</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>IOV</scope><scope>ISR</scope><scope>3V.</scope><scope>7QG</scope><scope>7QL</scope><scope>7QO</scope><scope>7RV</scope><scope>7SN</scope><scope>7SS</scope><scope>7T5</scope><scope>7TG</scope><scope>7TM</scope><scope>7U9</scope><scope>7X2</scope><scope>7X7</scope><scope>7XB</scope><scope>88E</scope><scope>8AO</scope><scope>8C1</scope><scope>8FD</scope><scope>8FE</scope><scope>8FG</scope><scope>8FH</scope><scope>8FI</scope><scope>8FJ</scope><scope>8FK</scope><scope>ABJCF</scope><scope>ABUWG</scope><scope>AEUYN</scope><scope>AFKRA</scope><scope>ARAPS</scope><scope>ATCPS</scope><scope>AZQEC</scope><scope>BBNVY</scope><scope>BENPR</scope><scope>BGLVJ</scope><scope>BHPHI</scope><scope>C1K</scope><scope>CCPQU</scope><scope>D1I</scope><scope>DWQXO</scope><scope>FR3</scope><scope>FYUFA</scope><scope>GHDGH</scope><scope>GNUQQ</scope><scope>H94</scope><scope>HCIFZ</scope><scope>K9.</scope><scope>KB.</scope><scope>KB0</scope><scope>KL.</scope><scope>L6V</scope><scope>LK8</scope><scope>M0K</scope><scope>M0S</scope><scope>M1P</scope><scope>M7N</scope><scope>M7P</scope><scope>M7S</scope><scope>NAPCQ</scope><scope>P5Z</scope><scope>P62</scope><scope>P64</scope><scope>PATMY</scope><scope>PDBOC</scope><scope>PIMPY</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>PTHSS</scope><scope>PYCSY</scope><scope>RC3</scope><scope>7X8</scope><scope>5PM</scope><scope>DOA</scope></search><sort><creationdate>20140807</creationdate><title>In vitro anti-influenza virus activities of a new lignan glycoside from the latex of Calotropis gigantea</title><author>Parhira, Supawadee ; Yang, Zi-Feng ; Zhu, Guo-Yuan ; Chen, Qiao-Lian ; Zhou, Bei-Xian ; Wang, Yu-Tao ; Liu, Liang ; Bai, Li-Ping ; Jiang, Zhi-Hong</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c758t-c37c1b1cbcb2f214b4798a08aaf337ffca71421e6619f249f95c03ecfa8c06443</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><topic>Activation</topic><topic>Analysis</topic><topic>Animals</topic><topic>Antiviral activity</topic><topic>Antiviral Agents - chemistry</topic><topic>Antiviral Agents - isolation & purification</topic><topic>Antiviral Agents - pharmacology</topic><topic>Assaying</topic><topic>Avian flu</topic><topic>Biology and Life Sciences</topic><topic>Calotropis gigantea</topic><topic>Chromatography</topic><topic>Dogs</topic><topic>Embryophyta - chemistry</topic><topic>Exports</topic><topic>Fourier transforms</topic><topic>Gene expression</topic><topic>Glycosides</topic><topic>Glycosides - chemistry</topic><topic>Glycosides - isolation & purification</topic><topic>Glycosides - pharmacology</topic><topic>Health aspects</topic><topic>Hospitals</topic><topic>Humans</topic><topic>Infections</topic><topic>Influenza</topic><topic>Influenza A Virus, H1N1 Subtype - physiology</topic><topic>Influenza viruses</topic><topic>Inhibition</topic><topic>Kinases</topic><topic>Laboratories</topic><topic>Latex</topic><topic>Latex - chemistry</topic><topic>Lignans - chemistry</topic><topic>Lignans - isolation & purification</topic><topic>Lignans - pharmacology</topic><topic>Madin Darby Canine Kidney Cells</topic><topic>Medicine</topic><topic>Metabolic pathways</topic><topic>NF-κB protein</topic><topic>Nuclear transport</topic><topic>Orthomyxoviridae Infections - drug therapy</topic><topic>Pandemics</topic><topic>Phenolic compounds</topic><topic>Phenols</topic><topic>Physical Sciences</topic><topic>Quality</topic><topic>Respiratory diseases</topic><topic>Ribonucleoproteins</topic><topic>Science</topic><topic>Sugar</topic><topic>Translocation</topic><topic>Viral infections</topic><topic>Virus replication</topic><topic>Virus Replication - drug effects</topic><topic>Viruses</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Parhira, Supawadee</creatorcontrib><creatorcontrib>Yang, Zi-Feng</creatorcontrib><creatorcontrib>Zhu, Guo-Yuan</creatorcontrib><creatorcontrib>Chen, Qiao-Lian</creatorcontrib><creatorcontrib>Zhou, Bei-Xian</creatorcontrib><creatorcontrib>Wang, Yu-Tao</creatorcontrib><creatorcontrib>Liu, Liang</creatorcontrib><creatorcontrib>Bai, Li-Ping</creatorcontrib><creatorcontrib>Jiang, Zhi-Hong</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Gale In Context: Opposing Viewpoints</collection><collection>Gale In Context: Science</collection><collection>ProQuest Central (Corporate)</collection><collection>Animal Behavior Abstracts</collection><collection>Bacteriology Abstracts (Microbiology B)</collection><collection>Biotechnology Research Abstracts</collection><collection>Nursing & Allied Health Database</collection><collection>Ecology Abstracts</collection><collection>Entomology Abstracts (Full archive)</collection><collection>Immunology Abstracts</collection><collection>Meteorological & Geoastrophysical Abstracts</collection><collection>Nucleic Acids Abstracts</collection><collection>Virology and AIDS Abstracts</collection><collection>Agricultural Science Collection</collection><collection>Health & Medical Collection</collection><collection>ProQuest Central (purchase pre-March 2016)</collection><collection>Medical Database (Alumni Edition)</collection><collection>ProQuest Pharma Collection</collection><collection>Public Health Database</collection><collection>Technology Research Database</collection><collection>ProQuest SciTech Collection</collection><collection>ProQuest Technology Collection</collection><collection>ProQuest Natural Science Collection</collection><collection>Hospital Premium Collection</collection><collection>Hospital Premium Collection (Alumni Edition)</collection><collection>ProQuest Central (Alumni) (purchase pre-March 2016)</collection><collection>Materials Science & Engineering Collection</collection><collection>ProQuest Central (Alumni Edition)</collection><collection>ProQuest One Sustainability</collection><collection>ProQuest Central UK/Ireland</collection><collection>Advanced Technologies & Aerospace Collection</collection><collection>Agricultural & Environmental Science Collection</collection><collection>ProQuest Central Essentials</collection><collection>Biological Science Collection</collection><collection>ProQuest Central</collection><collection>Technology Collection</collection><collection>Natural Science Collection</collection><collection>Environmental Sciences and Pollution Management</collection><collection>ProQuest One Community College</collection><collection>ProQuest Materials Science Collection</collection><collection>ProQuest Central Korea</collection><collection>Engineering Research Database</collection><collection>Health Research Premium Collection</collection><collection>Health Research Premium Collection (Alumni)</collection><collection>ProQuest Central Student</collection><collection>AIDS and Cancer Research Abstracts</collection><collection>SciTech Premium Collection</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>Materials Science Database</collection><collection>Nursing & Allied Health Database (Alumni Edition)</collection><collection>Meteorological & Geoastrophysical Abstracts - Academic</collection><collection>ProQuest Engineering Collection</collection><collection>ProQuest Biological Science Collection</collection><collection>Agricultural Science Database</collection><collection>Health & Medical Collection (Alumni Edition)</collection><collection>Medical Database</collection><collection>Algology Mycology and Protozoology Abstracts (Microbiology C)</collection><collection>Biological Science Database</collection><collection>Engineering Database</collection><collection>Nursing & Allied Health Premium</collection><collection>Advanced Technologies & Aerospace Database</collection><collection>ProQuest Advanced Technologies & Aerospace Collection</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>Environmental Science Database</collection><collection>Materials Science Collection</collection><collection>Publicly Available Content Database</collection><collection>ProQuest One Academic Eastern Edition (DO NOT USE)</collection><collection>ProQuest One Academic</collection><collection>ProQuest One Academic UKI Edition</collection><collection>Engineering Collection</collection><collection>Environmental Science Collection</collection><collection>Genetics Abstracts</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><collection>DOAJ Directory of Open Access Journals</collection><jtitle>PloS one</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Parhira, Supawadee</au><au>Yang, Zi-Feng</au><au>Zhu, Guo-Yuan</au><au>Chen, Qiao-Lian</au><au>Zhou, Bei-Xian</au><au>Wang, Yu-Tao</au><au>Liu, Liang</au><au>Bai, Li-Ping</au><au>Jiang, Zhi-Hong</au><au>Jin, Dong-Yan</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>In vitro anti-influenza virus activities of a new lignan glycoside from the latex of Calotropis gigantea</atitle><jtitle>PloS one</jtitle><addtitle>PLoS One</addtitle><date>2014-08-07</date><risdate>2014</risdate><volume>9</volume><issue>8</issue><spage>e104544</spage><epage>e104544</epage><pages>e104544-e104544</pages><issn>1932-6203</issn><eissn>1932-6203</eissn><abstract>A new lignan glycoside, (+)-pinoresinol 4-O-[6″-O-vanilloyl]-β-D-glucopyranoside (1) and two known phenolic compounds, 6'-O-vanilloyltachioside (2) and 6'-O-vanilloylisotachioside (3) were isolated from the latex of Calotropis gigantea (Asclepiadaceae). The structure of the new compound was elucidated by using spectroscopic and chemical methods. Three isolates (1-3) and one authentic compound, (+)-pinoresinol 4-O-β-D-glucopyranoside, were screened for A/PR/8/34 (H1N1) inhibitory activity by cytopathic effect (CPE) inhibition assay on MDCK cells. Compound 1 showed inhibitory activity against A/PR/8/34 (H1N1). In sharp contrast, the other three compounds (2, 3 and (+)-pinoresinol 4-O-β-D-glucopyranoside) did not show such activity. An analysis of structure-activity relationship between 1 and (+)-pinoresinol 4-O-β-D-glucopyranoside revealed that the presence of a vanilloyl group in the sugar moiety of 1 is crucial for its anti-influenza virus activity. Compound 1 was further evaluated for in vitro inhibitory activities against a panel of human and avian influenza viruses by CPE inhibition assay. It showed inhibitory effect against human influenza viruses in both subtypes A and B (IC50 values around 13.4-39.8 µM with SI values of 3.7-11.4), while had no effect on avian influenza viruses. Its antiviral activity against human influenza viruses subtype A was further confirmed by plaque reduction assay. The time course assay indicated that 1 exerts its antiviral activity at the early stage of viral replication. A mechanistic study showed that 1 efficiently inhibited influenza virus-induced activation of NF-κB pathway in a dose-dependent manner, but had no effect on virus-induced activation of Raf/MEK/ERK pathway. Further studies demonstrated that nuclear translocation of transcription factor NF-κB induced by influenza virus was significantly blocked by 1, meanwhile, nuclear export of viral ribonucleoproteins was also effectively inhibited. These findings suggest that this new lignan glycoside from Calotropis gigantea, may have therapeutic potential in influenza virus infection through inhibition of NF-κB pathway and viral ribonucleoproteins nuclear export.</abstract><cop>United States</cop><pub>Public Library of Science</pub><pmid>25102000</pmid><doi>10.1371/journal.pone.0104544</doi><oa>free_for_read</oa></addata></record> |
fulltext | fulltext |
identifier | ISSN: 1932-6203 |
ispartof | PloS one, 2014-08, Vol.9 (8), p.e104544-e104544 |
issn | 1932-6203 1932-6203 |
language | eng |
recordid | cdi_plos_journals_2014077704 |
source | MEDLINE; DOAJ Directory of Open Access Journals; Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals; PubMed Central; Free Full-Text Journals in Chemistry; Public Library of Science (PLoS) |
subjects | Activation Analysis Animals Antiviral activity Antiviral Agents - chemistry Antiviral Agents - isolation & purification Antiviral Agents - pharmacology Assaying Avian flu Biology and Life Sciences Calotropis gigantea Chromatography Dogs Embryophyta - chemistry Exports Fourier transforms Gene expression Glycosides Glycosides - chemistry Glycosides - isolation & purification Glycosides - pharmacology Health aspects Hospitals Humans Infections Influenza Influenza A Virus, H1N1 Subtype - physiology Influenza viruses Inhibition Kinases Laboratories Latex Latex - chemistry Lignans - chemistry Lignans - isolation & purification Lignans - pharmacology Madin Darby Canine Kidney Cells Medicine Metabolic pathways NF-κB protein Nuclear transport Orthomyxoviridae Infections - drug therapy Pandemics Phenolic compounds Phenols Physical Sciences Quality Respiratory diseases Ribonucleoproteins Science Sugar Translocation Viral infections Virus replication Virus Replication - drug effects Viruses |
title | In vitro anti-influenza virus activities of a new lignan glycoside from the latex of Calotropis gigantea |
url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-29T19%3A47%3A23IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-gale_plos_&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=In%20vitro%20anti-influenza%20virus%20activities%20of%20a%20new%20lignan%20glycoside%20from%20the%20latex%20of%20Calotropis%20gigantea&rft.jtitle=PloS%20one&rft.au=Parhira,%20Supawadee&rft.date=2014-08-07&rft.volume=9&rft.issue=8&rft.spage=e104544&rft.epage=e104544&rft.pages=e104544-e104544&rft.issn=1932-6203&rft.eissn=1932-6203&rft_id=info:doi/10.1371/journal.pone.0104544&rft_dat=%3Cgale_plos_%3EA418708540%3C/gale_plos_%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=2014077704&rft_id=info:pmid/25102000&rft_galeid=A418708540&rft_doaj_id=oai_doaj_org_article_eb092fe8e33a456db524a746680c2d12&rfr_iscdi=true |