Sylviside, a Diterpene Glucoside Derivative from Gnaphalium sylvaticum
A new diterpene glucoside (1), named sylviside, was isolated from the aerial parts of Gnaphalium sylvaticum. Its structure was elucidated as 2β,15α,20α-trihydroxy-19,20-dicarboxy-ent-kaur-16-ene 2β-O-(2‘-angelate)-β-d-glucopyranoside, on the basis of spectroscopic analysis (1H NMR, 13C NMR, HMQC, HM...
Gespeichert in:
| Veröffentlicht in: | Journal of natural products (Washington, D.C.) D.C.), 2006-03, Vol.69 (3), p.394-396 |
|---|---|
| Hauptverfasser: | , , , , , , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 396 |
|---|---|
| container_issue | 3 |
| container_start_page | 394 |
| container_title | Journal of natural products (Washington, D.C.) |
| container_volume | 69 |
| creator | Konopleva, Mira M Matławska, Irena Wojcińska, Małgorzata Ahmed Rybczyńska, Maria Paszel, Anna Ohta, Shinji Hirata, Toshifumi Bylka, Wiesława Mabry, Tom J Cannon, John F |
| description | A new diterpene glucoside (1), named sylviside, was isolated from the aerial parts of Gnaphalium sylvaticum. Its structure was elucidated as 2β,15α,20α-trihydroxy-19,20-dicarboxy-ent-kaur-16-ene 2β-O-(2‘-angelate)-β-d-glucopyranoside, on the basis of spectroscopic analysis (1H NMR, 13C NMR, HMQC, HMBC, NOESY), and was confirmed by X-ray crystallographic analysis. Sylviside (1) displayed weak cytotoxicity against HeLa WT (human epitheloid cervical carcinoma) cells and was also evaluated for its effects on reversing multidrug resistance in HeLa cells overexpressing MDR1. |
| doi_str_mv | 10.1021/np050144x |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_67799121</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>67799121</sourcerecordid><originalsourceid>FETCH-LOGICAL-a405t-cb7996817238c79d16fbe1d685f0d253d72905cba84b8b46e5b60c50bb4445e63</originalsourceid><addsrcrecordid>eNpt0E1v1DAQBmALgehSOPAHIBeQkAiMvybOEbV0i7QSSNuKo2U7DrjkCztZtf8er3bVvXCy5Hk8M34JeU3hEwVGPw8TSKBC3D8hKyoZlAhMPiUroMhLrlCckRcp3QEAh1o-J2cUJTIl2IpcbR-6XUih8R8LU1yG2cfJD75Yd4sb99fFpY9hZ-aw80Ubx75YD2b6bbqw9EXKb3PFLf1L8qw1XfKvjuc5ub36enNxXW6-r79dfNmURoCcS2erukZFK8aVq-qGYms9bVDJFhomeVOxGqSzRgmrrEAvLYKTYK0QQnrk5-T9oe8Ux7-LT7PuQ3K-68zgxyVprPIAymiGHw7QxTGl6Fs9xdCb-KAp6H1o-jG0bN8cmy62981JHlPK4N0RmORM10YzuJBOrkIUUu23Kw8upNnfP9ZN_JMX45XUNz-2WvLNzwqvQavs3x58a0ZtfsXc83bLgHKgUCOiOk02Lum7cYlDTvc_X_gHiMOXiQ</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>67799121</pqid></control><display><type>article</type><title>Sylviside, a Diterpene Glucoside Derivative from Gnaphalium sylvaticum</title><source>MEDLINE</source><source>ACS Journals: American Chemical Society Web Editions</source><creator>Konopleva, Mira M ; Matławska, Irena ; Wojcińska, Małgorzata ; Ahmed ; Rybczyńska, Maria ; Paszel, Anna ; Ohta, Shinji ; Hirata, Toshifumi ; Bylka, Wiesława ; Mabry, Tom J ; Cannon, John F</creator><creatorcontrib>Konopleva, Mira M ; Matławska, Irena ; Wojcińska, Małgorzata ; Ahmed ; Rybczyńska, Maria ; Paszel, Anna ; Ohta, Shinji ; Hirata, Toshifumi ; Bylka, Wiesława ; Mabry, Tom J ; Cannon, John F</creatorcontrib><description>A new diterpene glucoside (1), named sylviside, was isolated from the aerial parts of Gnaphalium sylvaticum. Its structure was elucidated as 2β,15α,20α-trihydroxy-19,20-dicarboxy-ent-kaur-16-ene 2β-O-(2‘-angelate)-β-d-glucopyranoside, on the basis of spectroscopic analysis (1H NMR, 13C NMR, HMQC, HMBC, NOESY), and was confirmed by X-ray crystallographic analysis. Sylviside (1) displayed weak cytotoxicity against HeLa WT (human epitheloid cervical carcinoma) cells and was also evaluated for its effects on reversing multidrug resistance in HeLa cells overexpressing MDR1.</description><identifier>ISSN: 0163-3864</identifier><identifier>EISSN: 1520-6025</identifier><identifier>DOI: 10.1021/np050144x</identifier><identifier>PMID: 16562842</identifier><identifier>CODEN: JNPRDF</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>anticarcinogenic activity ; Antineoplastic Agents, Phytogenic - chemistry ; Antineoplastic Agents, Phytogenic - isolation & purification ; Antineoplastic Agents, Phytogenic - pharmacology ; Asteraceae ; Biological and medical sciences ; chemical structure ; Crystallography, X-Ray ; cultured cells ; cytotoxicity ; Diterpenes - chemistry ; Diterpenes - isolation & purification ; Diterpenes - pharmacology ; diterpenoids ; Drug Resistance, Multiple ; Drug Screening Assays, Antitumor ; General pharmacology ; Genes, MDR - drug effects ; glucosides ; Glucosides - chemistry ; Glucosides - isolation & purification ; Glucosides - pharmacology ; Gnaphalium ; Gnaphalium - chemistry ; Gnaphalium sylvaticum ; HeLa Cells ; Humans ; Medical sciences ; medicinal plants ; Molecular Conformation ; Molecular Structure ; Pharmacognosy. Homeopathy. Health food ; Pharmacology. Drug treatments ; phytochemicals ; plant extracts ; Plants, Medicinal - chemistry ; Republic of Belarus ; spectral analysis ; stereochemistry ; sylviside</subject><ispartof>Journal of natural products (Washington, D.C.), 2006-03, Vol.69 (3), p.394-396</ispartof><rights>Copyright © 2006 American Chemical Society and American Society of Pharmacognosy</rights><rights>2006 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a405t-cb7996817238c79d16fbe1d685f0d253d72905cba84b8b46e5b60c50bb4445e63</citedby><cites>FETCH-LOGICAL-a405t-cb7996817238c79d16fbe1d685f0d253d72905cba84b8b46e5b60c50bb4445e63</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/np050144x$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/np050144x$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=17664586$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/16562842$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Konopleva, Mira M</creatorcontrib><creatorcontrib>Matławska, Irena</creatorcontrib><creatorcontrib>Wojcińska, Małgorzata</creatorcontrib><creatorcontrib>Ahmed</creatorcontrib><creatorcontrib>Rybczyńska, Maria</creatorcontrib><creatorcontrib>Paszel, Anna</creatorcontrib><creatorcontrib>Ohta, Shinji</creatorcontrib><creatorcontrib>Hirata, Toshifumi</creatorcontrib><creatorcontrib>Bylka, Wiesława</creatorcontrib><creatorcontrib>Mabry, Tom J</creatorcontrib><creatorcontrib>Cannon, John F</creatorcontrib><title>Sylviside, a Diterpene Glucoside Derivative from Gnaphalium sylvaticum</title><title>Journal of natural products (Washington, D.C.)</title><addtitle>J. Nat. Prod</addtitle><description>A new diterpene glucoside (1), named sylviside, was isolated from the aerial parts of Gnaphalium sylvaticum. Its structure was elucidated as 2β,15α,20α-trihydroxy-19,20-dicarboxy-ent-kaur-16-ene 2β-O-(2‘-angelate)-β-d-glucopyranoside, on the basis of spectroscopic analysis (1H NMR, 13C NMR, HMQC, HMBC, NOESY), and was confirmed by X-ray crystallographic analysis. Sylviside (1) displayed weak cytotoxicity against HeLa WT (human epitheloid cervical carcinoma) cells and was also evaluated for its effects on reversing multidrug resistance in HeLa cells overexpressing MDR1.</description><subject>anticarcinogenic activity</subject><subject>Antineoplastic Agents, Phytogenic - chemistry</subject><subject>Antineoplastic Agents, Phytogenic - isolation & purification</subject><subject>Antineoplastic Agents, Phytogenic - pharmacology</subject><subject>Asteraceae</subject><subject>Biological and medical sciences</subject><subject>chemical structure</subject><subject>Crystallography, X-Ray</subject><subject>cultured cells</subject><subject>cytotoxicity</subject><subject>Diterpenes - chemistry</subject><subject>Diterpenes - isolation & purification</subject><subject>Diterpenes - pharmacology</subject><subject>diterpenoids</subject><subject>Drug Resistance, Multiple</subject><subject>Drug Screening Assays, Antitumor</subject><subject>General pharmacology</subject><subject>Genes, MDR - drug effects</subject><subject>glucosides</subject><subject>Glucosides - chemistry</subject><subject>Glucosides - isolation & purification</subject><subject>Glucosides - pharmacology</subject><subject>Gnaphalium</subject><subject>Gnaphalium - chemistry</subject><subject>Gnaphalium sylvaticum</subject><subject>HeLa Cells</subject><subject>Humans</subject><subject>Medical sciences</subject><subject>medicinal plants</subject><subject>Molecular Conformation</subject><subject>Molecular Structure</subject><subject>Pharmacognosy. Homeopathy. Health food</subject><subject>Pharmacology. Drug treatments</subject><subject>phytochemicals</subject><subject>plant extracts</subject><subject>Plants, Medicinal - chemistry</subject><subject>Republic of Belarus</subject><subject>spectral analysis</subject><subject>stereochemistry</subject><subject>sylviside</subject><issn>0163-3864</issn><issn>1520-6025</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2006</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpt0E1v1DAQBmALgehSOPAHIBeQkAiMvybOEbV0i7QSSNuKo2U7DrjkCztZtf8er3bVvXCy5Hk8M34JeU3hEwVGPw8TSKBC3D8hKyoZlAhMPiUroMhLrlCckRcp3QEAh1o-J2cUJTIl2IpcbR-6XUih8R8LU1yG2cfJD75Yd4sb99fFpY9hZ-aw80Ubx75YD2b6bbqw9EXKb3PFLf1L8qw1XfKvjuc5ub36enNxXW6-r79dfNmURoCcS2erukZFK8aVq-qGYms9bVDJFhomeVOxGqSzRgmrrEAvLYKTYK0QQnrk5-T9oe8Ux7-LT7PuQ3K-68zgxyVprPIAymiGHw7QxTGl6Fs9xdCb-KAp6H1o-jG0bN8cmy62981JHlPK4N0RmORM10YzuJBOrkIUUu23Kw8upNnfP9ZN_JMX45XUNz-2WvLNzwqvQavs3x58a0ZtfsXc83bLgHKgUCOiOk02Lum7cYlDTvc_X_gHiMOXiQ</recordid><startdate>20060301</startdate><enddate>20060301</enddate><creator>Konopleva, Mira M</creator><creator>Matławska, Irena</creator><creator>Wojcińska, Małgorzata</creator><creator>Ahmed</creator><creator>Rybczyńska, Maria</creator><creator>Paszel, Anna</creator><creator>Ohta, Shinji</creator><creator>Hirata, Toshifumi</creator><creator>Bylka, Wiesława</creator><creator>Mabry, Tom J</creator><creator>Cannon, John F</creator><general>American Chemical Society</general><general>American Society of Pharmacognosy</general><scope>FBQ</scope><scope>BSCLL</scope><scope>IQODW</scope><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>7X8</scope></search><sort><creationdate>20060301</creationdate><title>Sylviside, a Diterpene Glucoside Derivative from Gnaphalium sylvaticum</title><author>Konopleva, Mira M ; Matławska, Irena ; Wojcińska, Małgorzata ; Ahmed ; Rybczyńska, Maria ; Paszel, Anna ; Ohta, Shinji ; Hirata, Toshifumi ; Bylka, Wiesława ; Mabry, Tom J ; Cannon, John F</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a405t-cb7996817238c79d16fbe1d685f0d253d72905cba84b8b46e5b60c50bb4445e63</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2006</creationdate><topic>anticarcinogenic activity</topic><topic>Antineoplastic Agents, Phytogenic - chemistry</topic><topic>Antineoplastic Agents, Phytogenic - isolation & purification</topic><topic>Antineoplastic Agents, Phytogenic - pharmacology</topic><topic>Asteraceae</topic><topic>Biological and medical sciences</topic><topic>chemical structure</topic><topic>Crystallography, X-Ray</topic><topic>cultured cells</topic><topic>cytotoxicity</topic><topic>Diterpenes - chemistry</topic><topic>Diterpenes - isolation & purification</topic><topic>Diterpenes - pharmacology</topic><topic>diterpenoids</topic><topic>Drug Resistance, Multiple</topic><topic>Drug Screening Assays, Antitumor</topic><topic>General pharmacology</topic><topic>Genes, MDR - drug effects</topic><topic>glucosides</topic><topic>Glucosides - chemistry</topic><topic>Glucosides - isolation & purification</topic><topic>Glucosides - pharmacology</topic><topic>Gnaphalium</topic><topic>Gnaphalium - chemistry</topic><topic>Gnaphalium sylvaticum</topic><topic>HeLa Cells</topic><topic>Humans</topic><topic>Medical sciences</topic><topic>medicinal plants</topic><topic>Molecular Conformation</topic><topic>Molecular Structure</topic><topic>Pharmacognosy. Homeopathy. Health food</topic><topic>Pharmacology. Drug treatments</topic><topic>phytochemicals</topic><topic>plant extracts</topic><topic>Plants, Medicinal - chemistry</topic><topic>Republic of Belarus</topic><topic>spectral analysis</topic><topic>stereochemistry</topic><topic>sylviside</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Konopleva, Mira M</creatorcontrib><creatorcontrib>Matławska, Irena</creatorcontrib><creatorcontrib>Wojcińska, Małgorzata</creatorcontrib><creatorcontrib>Ahmed</creatorcontrib><creatorcontrib>Rybczyńska, Maria</creatorcontrib><creatorcontrib>Paszel, Anna</creatorcontrib><creatorcontrib>Ohta, Shinji</creatorcontrib><creatorcontrib>Hirata, Toshifumi</creatorcontrib><creatorcontrib>Bylka, Wiesława</creatorcontrib><creatorcontrib>Mabry, Tom J</creatorcontrib><creatorcontrib>Cannon, John F</creatorcontrib><collection>AGRIS</collection><collection>Istex</collection><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of natural products (Washington, D.C.)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Konopleva, Mira M</au><au>Matławska, Irena</au><au>Wojcińska, Małgorzata</au><au>Ahmed</au><au>Rybczyńska, Maria</au><au>Paszel, Anna</au><au>Ohta, Shinji</au><au>Hirata, Toshifumi</au><au>Bylka, Wiesława</au><au>Mabry, Tom J</au><au>Cannon, John F</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Sylviside, a Diterpene Glucoside Derivative from Gnaphalium sylvaticum</atitle><jtitle>Journal of natural products (Washington, D.C.)</jtitle><addtitle>J. Nat. Prod</addtitle><date>2006-03-01</date><risdate>2006</risdate><volume>69</volume><issue>3</issue><spage>394</spage><epage>396</epage><pages>394-396</pages><issn>0163-3864</issn><eissn>1520-6025</eissn><coden>JNPRDF</coden><abstract>A new diterpene glucoside (1), named sylviside, was isolated from the aerial parts of Gnaphalium sylvaticum. Its structure was elucidated as 2β,15α,20α-trihydroxy-19,20-dicarboxy-ent-kaur-16-ene 2β-O-(2‘-angelate)-β-d-glucopyranoside, on the basis of spectroscopic analysis (1H NMR, 13C NMR, HMQC, HMBC, NOESY), and was confirmed by X-ray crystallographic analysis. Sylviside (1) displayed weak cytotoxicity against HeLa WT (human epitheloid cervical carcinoma) cells and was also evaluated for its effects on reversing multidrug resistance in HeLa cells overexpressing MDR1.</abstract><cop>Washington, DC</cop><cop>Glendale, AZ</cop><pub>American Chemical Society</pub><pmid>16562842</pmid><doi>10.1021/np050144x</doi><tpages>3</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0163-3864 |
| ispartof | Journal of natural products (Washington, D.C.), 2006-03, Vol.69 (3), p.394-396 |
| issn | 0163-3864 1520-6025 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_67799121 |
| source | MEDLINE; ACS Journals: American Chemical Society Web Editions |
| subjects | anticarcinogenic activity Antineoplastic Agents, Phytogenic - chemistry Antineoplastic Agents, Phytogenic - isolation & purification Antineoplastic Agents, Phytogenic - pharmacology Asteraceae Biological and medical sciences chemical structure Crystallography, X-Ray cultured cells cytotoxicity Diterpenes - chemistry Diterpenes - isolation & purification Diterpenes - pharmacology diterpenoids Drug Resistance, Multiple Drug Screening Assays, Antitumor General pharmacology Genes, MDR - drug effects glucosides Glucosides - chemistry Glucosides - isolation & purification Glucosides - pharmacology Gnaphalium Gnaphalium - chemistry Gnaphalium sylvaticum HeLa Cells Humans Medical sciences medicinal plants Molecular Conformation Molecular Structure Pharmacognosy. Homeopathy. Health food Pharmacology. Drug treatments phytochemicals plant extracts Plants, Medicinal - chemistry Republic of Belarus spectral analysis stereochemistry sylviside |
| title | Sylviside, a Diterpene Glucoside Derivative from Gnaphalium sylvaticum |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-01T09%3A08%3A27IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Sylviside,%20a%20Diterpene%20Glucoside%20Derivative%20from%20Gnaphalium%20sylvaticum&rft.jtitle=Journal%20of%20natural%20products%20(Washington,%20D.C.)&rft.au=Konopleva,%20Mira%20M&rft.date=2006-03-01&rft.volume=69&rft.issue=3&rft.spage=394&rft.epage=396&rft.pages=394-396&rft.issn=0163-3864&rft.eissn=1520-6025&rft.coden=JNPRDF&rft_id=info:doi/10.1021/np050144x&rft_dat=%3Cproquest_cross%3E67799121%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=67799121&rft_id=info:pmid/16562842&rfr_iscdi=true |