A Dimeric Sesquiterpenoid from a Malaysian Meiogyne as a New Inhibitor of Bcl-xL/BakBH3 Domain Peptide Interaction
In an effort to find potent inhibitors of the antiapoptotic protein Bcl-xL, a systematic in vitro evaluation was undertaken on 1470 Malaysian plant extracts. The ethyl acetate extract obtained from the bark of Meiogyne cylindrocarpa was selected for its interaction with the Bcl-xL/Bak association. B...
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| Veröffentlicht in: | Journal of natural products (Washington, D.C.) D.C.), 2009-03, Vol.72 (3), p.480-483 |
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| creator | Litaudon, Marc Bousserouel, Hadjira Awang, Khalijah Nosjean, Olivier Martin, Marie-Thérèse Dau, Marie Elise Tran Huu Hadi, Hamid A Boutin, Jean A Sévenet, Thierry Guéritte, Françoise |
| description | In an effort to find potent inhibitors of the antiapoptotic protein Bcl-xL, a systematic in vitro evaluation was undertaken on 1470 Malaysian plant extracts. The ethyl acetate extract obtained from the bark of Meiogyne cylindrocarpa was selected for its interaction with the Bcl-xL/Bak association. Bioassay-guided purification of this species led to the isolation of two new dimeric sesquiterpenoids (1 and 2) possessing an unprecedented substituted cis-decalin carbon skeleton. Meiogynin A (1) showed the strongest activity with a K i of 10.8 ± 3.1 μM. |
| doi_str_mv | 10.1021/np8006292 |
| format | Article |
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The ethyl acetate extract obtained from the bark of Meiogyne cylindrocarpa was selected for its interaction with the Bcl-xL/Bak association. Bioassay-guided purification of this species led to the isolation of two new dimeric sesquiterpenoids (1 and 2) possessing an unprecedented substituted cis-decalin carbon skeleton. Meiogynin A (1) showed the strongest activity with a K i of 10.8 ± 3.1 μM.</description><identifier>ISSN: 0163-3864</identifier><identifier>EISSN: 1520-6025</identifier><identifier>DOI: 10.1021/np8006292</identifier><identifier>PMID: 19161318</identifier><identifier>CODEN: JNPRDF</identifier><language>eng</language><publisher>Northbrook, IL: American Chemical Society and American Society of Pharmacognosy</publisher><subject>Annonaceae ; anticarcinogenic activity ; biochemical pathways ; Biological and medical sciences ; Cellular Biology ; chemical structure ; cytotoxicity ; General pharmacology ; Life Sciences ; Malaysia ; Medical sciences ; medicinal properties ; Meiogyne cylindrocarpa ; meiogynin ; Molecular Structure ; Pharmacognosy. Homeopathy. Health food ; Pharmacology. Drug treatments ; Plant Bark - chemistry ; Proto-Oncogene Proteins c-bcl-2 - antagonists & inhibitors ; Sesquiterpenes - chemistry ; Sesquiterpenes - isolation & purification ; Sesquiterpenes - pharmacology ; sesquiterpenoids ; spectral analysis ; stereochemistry ; Stereoisomerism</subject><ispartof>Journal of natural products (Washington, D.C.), 2009-03, Vol.72 (3), p.480-483</ispartof><rights>Copyright © 2009 American Chemical Society and American Society of Pharmacognosy</rights><rights>2009 INIST-CNRS</rights><rights>Distributed under a Creative Commons Attribution 4.0 International License</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a402t-2f933d977ccf59f026c42c196be0215d0ec44773767b61abedd8131dee35d8f13</citedby><cites>FETCH-LOGICAL-a402t-2f933d977ccf59f026c42c196be0215d0ec44773767b61abedd8131dee35d8f13</cites><orcidid>0000-0002-0877-8234</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/np8006292$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/np8006292$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>230,314,776,780,881,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=21366897$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/19161318$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink><backlink>$$Uhttps://hal.science/hal-00377470$$DView record in HAL$$Hfree_for_read</backlink></links><search><creatorcontrib>Litaudon, Marc</creatorcontrib><creatorcontrib>Bousserouel, Hadjira</creatorcontrib><creatorcontrib>Awang, Khalijah</creatorcontrib><creatorcontrib>Nosjean, Olivier</creatorcontrib><creatorcontrib>Martin, Marie-Thérèse</creatorcontrib><creatorcontrib>Dau, Marie Elise Tran Huu</creatorcontrib><creatorcontrib>Hadi, Hamid A</creatorcontrib><creatorcontrib>Boutin, Jean A</creatorcontrib><creatorcontrib>Sévenet, Thierry</creatorcontrib><creatorcontrib>Guéritte, Françoise</creatorcontrib><title>A Dimeric Sesquiterpenoid from a Malaysian Meiogyne as a New Inhibitor of Bcl-xL/BakBH3 Domain Peptide Interaction</title><title>Journal of natural products (Washington, D.C.)</title><addtitle>J. Nat. Prod</addtitle><description>In an effort to find potent inhibitors of the antiapoptotic protein Bcl-xL, a systematic in vitro evaluation was undertaken on 1470 Malaysian plant extracts. The ethyl acetate extract obtained from the bark of Meiogyne cylindrocarpa was selected for its interaction with the Bcl-xL/Bak association. Bioassay-guided purification of this species led to the isolation of two new dimeric sesquiterpenoids (1 and 2) possessing an unprecedented substituted cis-decalin carbon skeleton. Meiogynin A (1) showed the strongest activity with a K i of 10.8 ± 3.1 μM.</description><subject>Annonaceae</subject><subject>anticarcinogenic activity</subject><subject>biochemical pathways</subject><subject>Biological and medical sciences</subject><subject>Cellular Biology</subject><subject>chemical structure</subject><subject>cytotoxicity</subject><subject>General pharmacology</subject><subject>Life Sciences</subject><subject>Malaysia</subject><subject>Medical sciences</subject><subject>medicinal properties</subject><subject>Meiogyne cylindrocarpa</subject><subject>meiogynin</subject><subject>Molecular Structure</subject><subject>Pharmacognosy. Homeopathy. Health food</subject><subject>Pharmacology. Drug treatments</subject><subject>Plant Bark - chemistry</subject><subject>Proto-Oncogene Proteins c-bcl-2 - antagonists & inhibitors</subject><subject>Sesquiterpenes - chemistry</subject><subject>Sesquiterpenes - isolation & purification</subject><subject>Sesquiterpenes - pharmacology</subject><subject>sesquiterpenoids</subject><subject>spectral analysis</subject><subject>stereochemistry</subject><subject>Stereoisomerism</subject><issn>0163-3864</issn><issn>1520-6025</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2009</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkU1vEzEQhi0EomnhwB8AXyrEYak_du3dY9ICqZQCUunZmnjt1mXX3tq7lPx7HCVKLpxGGj16NPO-CL2j5DMljF74oSZEsIa9QDNaMVIIwqqXaEao4AWvRXmCTlN6JIRw0lSv0QltqKCc1jMU5_jK9SY6jW9NeprcaOJgfHAttjH0GPANdLBJDjy-MS7cb7zBkPL-u3nG1_7Brd0YIg4WL3RX_F1dLOD3YsnxVejBefzTDKNrTSazGPTogn-DXlnoknm7n2fo7uuXX5fLYvXj2_XlfFVASdhYMNtw3jZSam2rxhImdMk0bcTa5J-rlhhdllJyKeRaUFibtq3zT60xvGprS_kZ-rTzPkCnhuh6iBsVwKnlfKW2uxyHlKUkf7bsxx07xPA0mTSq3iVtug68CVNSknPR1IySo1XHkFI09qCmRG3bUIc2Mvt-b53WvWmP5D7-DJzvAUgaOhvBa5cOHKNciLqRmfuw4ywEBfcxM3e3jFC-bZjVZXk0gU7qMUzR52j_c9I_HeOkQA</recordid><startdate>20090327</startdate><enddate>20090327</enddate><creator>Litaudon, Marc</creator><creator>Bousserouel, Hadjira</creator><creator>Awang, Khalijah</creator><creator>Nosjean, Olivier</creator><creator>Martin, Marie-Thérèse</creator><creator>Dau, Marie Elise Tran Huu</creator><creator>Hadi, Hamid A</creator><creator>Boutin, Jean A</creator><creator>Sévenet, Thierry</creator><creator>Guéritte, Françoise</creator><general>American Chemical Society and American Society of Pharmacognosy</general><general>American Society of Pharmacognosy</general><general>American Chemical Society</general><scope>FBQ</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><scope>1XC</scope><orcidid>https://orcid.org/0000-0002-0877-8234</orcidid></search><sort><creationdate>20090327</creationdate><title>A Dimeric Sesquiterpenoid from a Malaysian Meiogyne as a New Inhibitor of Bcl-xL/BakBH3 Domain Peptide Interaction</title><author>Litaudon, Marc ; Bousserouel, Hadjira ; Awang, Khalijah ; Nosjean, Olivier ; Martin, Marie-Thérèse ; Dau, Marie Elise Tran Huu ; Hadi, Hamid A ; Boutin, Jean A ; Sévenet, Thierry ; Guéritte, Françoise</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a402t-2f933d977ccf59f026c42c196be0215d0ec44773767b61abedd8131dee35d8f13</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2009</creationdate><topic>Annonaceae</topic><topic>anticarcinogenic activity</topic><topic>biochemical pathways</topic><topic>Biological and medical sciences</topic><topic>Cellular Biology</topic><topic>chemical structure</topic><topic>cytotoxicity</topic><topic>General pharmacology</topic><topic>Life Sciences</topic><topic>Malaysia</topic><topic>Medical sciences</topic><topic>medicinal properties</topic><topic>Meiogyne cylindrocarpa</topic><topic>meiogynin</topic><topic>Molecular Structure</topic><topic>Pharmacognosy. Homeopathy. Health food</topic><topic>Pharmacology. Drug treatments</topic><topic>Plant Bark - chemistry</topic><topic>Proto-Oncogene Proteins c-bcl-2 - antagonists & inhibitors</topic><topic>Sesquiterpenes - chemistry</topic><topic>Sesquiterpenes - isolation & purification</topic><topic>Sesquiterpenes - pharmacology</topic><topic>sesquiterpenoids</topic><topic>spectral analysis</topic><topic>stereochemistry</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Litaudon, Marc</creatorcontrib><creatorcontrib>Bousserouel, Hadjira</creatorcontrib><creatorcontrib>Awang, Khalijah</creatorcontrib><creatorcontrib>Nosjean, Olivier</creatorcontrib><creatorcontrib>Martin, Marie-Thérèse</creatorcontrib><creatorcontrib>Dau, Marie Elise Tran Huu</creatorcontrib><creatorcontrib>Hadi, Hamid A</creatorcontrib><creatorcontrib>Boutin, Jean A</creatorcontrib><creatorcontrib>Sévenet, Thierry</creatorcontrib><creatorcontrib>Guéritte, Françoise</creatorcontrib><collection>AGRIS</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><collection>Hyper Article en Ligne (HAL)</collection><jtitle>Journal of natural products (Washington, D.C.)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Litaudon, Marc</au><au>Bousserouel, Hadjira</au><au>Awang, Khalijah</au><au>Nosjean, Olivier</au><au>Martin, Marie-Thérèse</au><au>Dau, Marie Elise Tran Huu</au><au>Hadi, Hamid A</au><au>Boutin, Jean A</au><au>Sévenet, Thierry</au><au>Guéritte, Françoise</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A Dimeric Sesquiterpenoid from a Malaysian Meiogyne as a New Inhibitor of Bcl-xL/BakBH3 Domain Peptide Interaction</atitle><jtitle>Journal of natural products (Washington, D.C.)</jtitle><addtitle>J. Nat. Prod</addtitle><date>2009-03-27</date><risdate>2009</risdate><volume>72</volume><issue>3</issue><spage>480</spage><epage>483</epage><pages>480-483</pages><issn>0163-3864</issn><eissn>1520-6025</eissn><coden>JNPRDF</coden><abstract>In an effort to find potent inhibitors of the antiapoptotic protein Bcl-xL, a systematic in vitro evaluation was undertaken on 1470 Malaysian plant extracts. The ethyl acetate extract obtained from the bark of Meiogyne cylindrocarpa was selected for its interaction with the Bcl-xL/Bak association. Bioassay-guided purification of this species led to the isolation of two new dimeric sesquiterpenoids (1 and 2) possessing an unprecedented substituted cis-decalin carbon skeleton. Meiogynin A (1) showed the strongest activity with a K i of 10.8 ± 3.1 μM.</abstract><cop>Northbrook, IL</cop><pub>American Chemical Society and American Society of Pharmacognosy</pub><pmid>19161318</pmid><doi>10.1021/np8006292</doi><tpages>4</tpages><orcidid>https://orcid.org/0000-0002-0877-8234</orcidid></addata></record> |
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| ispartof | Journal of natural products (Washington, D.C.), 2009-03, Vol.72 (3), p.480-483 |
| issn | 0163-3864 1520-6025 |
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| source | ACS Publications; MEDLINE |
| subjects | Annonaceae anticarcinogenic activity biochemical pathways Biological and medical sciences Cellular Biology chemical structure cytotoxicity General pharmacology Life Sciences Malaysia Medical sciences medicinal properties Meiogyne cylindrocarpa meiogynin Molecular Structure Pharmacognosy. Homeopathy. Health food Pharmacology. Drug treatments Plant Bark - chemistry Proto-Oncogene Proteins c-bcl-2 - antagonists & inhibitors Sesquiterpenes - chemistry Sesquiterpenes - isolation & purification Sesquiterpenes - pharmacology sesquiterpenoids spectral analysis stereochemistry Stereoisomerism |
| title | A Dimeric Sesquiterpenoid from a Malaysian Meiogyne as a New Inhibitor of Bcl-xL/BakBH3 Domain Peptide Interaction |
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