Antiviral chlorinated daphnane diterpenoid orthoesters from the bark and wood of Trigonostemon cherrieri
The chemical investigation of the bark and wood of Trigonostemon cherrieri (Euphorbiaceae) led to the isolation of ten chlorinated daphnane diterpenoid orthoesters (DDO) named trigocherrins A–F (1–6) and trigocherriolides A–D (7–10). Several DDO exhibited strong antiviral activity against chinkungun...
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| Veröffentlicht in: | Phytochemistry (Oxford) 2012-12, Vol.84, p.160-168 |
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| creator | Allard, Pierre-Marie Leyssen, Pieter Martin, Marie-Thérèse Bourjot, Mélanie Dumontet, Vincent Eydoux, Cécilia Guillemot, Jean-Claude Canard, Bruno Poullain, Cyril Guéritte, Françoise Litaudon, Marc |
| description | The chemical investigation of the bark and wood of Trigonostemon cherrieri (Euphorbiaceae) led to the isolation of ten chlorinated daphnane diterpenoid orthoesters (DDO) named trigocherrins A–F (1–6) and trigocherriolides A–D (7–10). Several DDO exhibited strong antiviral activity against chinkungunya, Sindbis and Semliki forest virus. [Display omitted]
► Ten daphnane diterpenoid orthoesters were isolated from Trigonostemon cherrieri. ► They all possess a mono- or dichlorovinyl group on the daphnane core. ► They were isolated using bioassay-guided and LC/MS-guided fractionations. ► They are a class of non-nucleosidic inhibitor of the DENV NS5 RdRp. ► They showed strong antiviral activity against CHIK, Sindbis and Semliki forest virus.
The chemical study of the bark and the wood of Trigonostemon cherrieri, a rare endemic plant of New Caledonia, led to the isolation of a series of highly oxygenated daphnane diterpenoid orthoesters (DDO) bearing an uncommon chlorinated moiety: trigocherrins A–F and trigocherriolides A–D. Herein, we describe the isolation and structure elucidation of the DDO (trigocherrins B–F and trigocherriolides A–D). We also report the antiviral activity of trigocherrins A, B and F (1, 2 and 6) and trigocherriolides A, B and C (7–9) against various emerging pathogens: chikungunya virus (CHIKV), Sindbis virus (SINV), Semliki forest virus (SFV) and dengue virus (DENV). |
| doi_str_mv | 10.1016/j.phytochem.2012.07.023 |
| format | Article |
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► Ten daphnane diterpenoid orthoesters were isolated from Trigonostemon cherrieri. ► They all possess a mono- or dichlorovinyl group on the daphnane core. ► They were isolated using bioassay-guided and LC/MS-guided fractionations. ► They are a class of non-nucleosidic inhibitor of the DENV NS5 RdRp. ► They showed strong antiviral activity against CHIK, Sindbis and Semliki forest virus.
The chemical study of the bark and the wood of Trigonostemon cherrieri, a rare endemic plant of New Caledonia, led to the isolation of a series of highly oxygenated daphnane diterpenoid orthoesters (DDO) bearing an uncommon chlorinated moiety: trigocherrins A–F and trigocherriolides A–D. Herein, we describe the isolation and structure elucidation of the DDO (trigocherrins B–F and trigocherriolides A–D). We also report the antiviral activity of trigocherrins A, B and F (1, 2 and 6) and trigocherriolides A, B and C (7–9) against various emerging pathogens: chikungunya virus (CHIKV), Sindbis virus (SINV), Semliki forest virus (SFV) and dengue virus (DENV).</description><identifier>ISSN: 0031-9422</identifier><identifier>EISSN: 1873-3700</identifier><identifier>DOI: 10.1016/j.phytochem.2012.07.023</identifier><identifier>PMID: 22938995</identifier><language>eng</language><publisher>England: Elsevier Ltd</publisher><subject>Antiviral ; Antiviral Agents - chemistry ; Antiviral Agents - isolation & purification ; Antiviral Agents - pharmacology ; antiviral properties ; bark ; Chemical Sciences ; Chikungunya virus ; Chikungunya virus - drug effects ; Chlorinated diterpenes ; chlorination ; Daphnane ; Dengue virus ; Dengue Virus - drug effects ; Diterpenes - chemistry ; Diterpenes - isolation & purification ; Diterpenes - pharmacology ; diterpenoids ; Esters - chemistry ; Esters - isolation & purification ; Esters - pharmacology ; Euphorbiaceae ; Euphorbiaceae - chemistry ; indigenous species ; Microbial Sensitivity Tests ; Molecular Conformation ; Organic chemistry ; pathogens ; Plant Bark - chemistry ; plants (botany) ; Semliki Forest virus ; Semliki forest virus - drug effects ; Sindbis virus ; Sindbis Virus - drug effects ; Trigocherrin ; Trigocherriolide ; Trigonostemon cherrieri ; wood ; Wood - chemistry</subject><ispartof>Phytochemistry (Oxford), 2012-12, Vol.84, p.160-168</ispartof><rights>2012 Elsevier Ltd</rights><rights>Copyright © 2012 Elsevier Ltd. All rights reserved.</rights><rights>Distributed under a Creative Commons Attribution 4.0 International License</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c528t-26511dafcaaf223b951f3acdcaa6bbc1ec8e73b12d6a9db712a49c1721655ee93</citedby><cites>FETCH-LOGICAL-c528t-26511dafcaaf223b951f3acdcaa6bbc1ec8e73b12d6a9db712a49c1721655ee93</cites><orcidid>0000-0003-3330-3457 ; 0000-0003-4181-592X ; 0000-0002-0877-8234 ; 0000-0003-3389-2191 ; 0000-0003-4924-1991</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.phytochem.2012.07.023$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>230,314,780,784,885,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/22938995$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink><backlink>$$Uhttps://hal.science/hal-00769790$$DView record in HAL$$Hfree_for_read</backlink></links><search><creatorcontrib>Allard, Pierre-Marie</creatorcontrib><creatorcontrib>Leyssen, Pieter</creatorcontrib><creatorcontrib>Martin, Marie-Thérèse</creatorcontrib><creatorcontrib>Bourjot, Mélanie</creatorcontrib><creatorcontrib>Dumontet, Vincent</creatorcontrib><creatorcontrib>Eydoux, Cécilia</creatorcontrib><creatorcontrib>Guillemot, Jean-Claude</creatorcontrib><creatorcontrib>Canard, Bruno</creatorcontrib><creatorcontrib>Poullain, Cyril</creatorcontrib><creatorcontrib>Guéritte, Françoise</creatorcontrib><creatorcontrib>Litaudon, Marc</creatorcontrib><title>Antiviral chlorinated daphnane diterpenoid orthoesters from the bark and wood of Trigonostemon cherrieri</title><title>Phytochemistry (Oxford)</title><addtitle>Phytochemistry</addtitle><description>The chemical investigation of the bark and wood of Trigonostemon cherrieri (Euphorbiaceae) led to the isolation of ten chlorinated daphnane diterpenoid orthoesters (DDO) named trigocherrins A–F (1–6) and trigocherriolides A–D (7–10). Several DDO exhibited strong antiviral activity against chinkungunya, Sindbis and Semliki forest virus. [Display omitted]
► Ten daphnane diterpenoid orthoesters were isolated from Trigonostemon cherrieri. ► They all possess a mono- or dichlorovinyl group on the daphnane core. ► They were isolated using bioassay-guided and LC/MS-guided fractionations. ► They are a class of non-nucleosidic inhibitor of the DENV NS5 RdRp. ► They showed strong antiviral activity against CHIK, Sindbis and Semliki forest virus.
The chemical study of the bark and the wood of Trigonostemon cherrieri, a rare endemic plant of New Caledonia, led to the isolation of a series of highly oxygenated daphnane diterpenoid orthoesters (DDO) bearing an uncommon chlorinated moiety: trigocherrins A–F and trigocherriolides A–D. Herein, we describe the isolation and structure elucidation of the DDO (trigocherrins B–F and trigocherriolides A–D). We also report the antiviral activity of trigocherrins A, B and F (1, 2 and 6) and trigocherriolides A, B and C (7–9) against various emerging pathogens: chikungunya virus (CHIKV), Sindbis virus (SINV), Semliki forest virus (SFV) and dengue virus (DENV).</description><subject>Antiviral</subject><subject>Antiviral Agents - chemistry</subject><subject>Antiviral Agents - isolation & purification</subject><subject>Antiviral Agents - pharmacology</subject><subject>antiviral properties</subject><subject>bark</subject><subject>Chemical Sciences</subject><subject>Chikungunya virus</subject><subject>Chikungunya virus - drug effects</subject><subject>Chlorinated diterpenes</subject><subject>chlorination</subject><subject>Daphnane</subject><subject>Dengue virus</subject><subject>Dengue Virus - drug effects</subject><subject>Diterpenes - chemistry</subject><subject>Diterpenes - isolation & purification</subject><subject>Diterpenes - pharmacology</subject><subject>diterpenoids</subject><subject>Esters - chemistry</subject><subject>Esters - isolation & purification</subject><subject>Esters - pharmacology</subject><subject>Euphorbiaceae</subject><subject>Euphorbiaceae - chemistry</subject><subject>indigenous species</subject><subject>Microbial Sensitivity Tests</subject><subject>Molecular Conformation</subject><subject>Organic chemistry</subject><subject>pathogens</subject><subject>Plant Bark - chemistry</subject><subject>plants (botany)</subject><subject>Semliki Forest virus</subject><subject>Semliki forest virus - drug effects</subject><subject>Sindbis virus</subject><subject>Sindbis Virus - drug effects</subject><subject>Trigocherrin</subject><subject>Trigocherriolide</subject><subject>Trigonostemon cherrieri</subject><subject>wood</subject><subject>Wood - chemistry</subject><issn>0031-9422</issn><issn>1873-3700</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkUFv1DAQhSMEokvhL1Af4ZAwdtZ2fFxVQJFW4kB7thx70nhJ4sXOLuq_x1HKXnuyZvTN85t5RXFDoaJAxZdDdeyf5mB7HCsGlFUgK2D1q2JDG1mXtQR4XWwAalqqLWNXxbuUDgDAuRBviyvGVN0oxTdFv5tmf_bRDMT2Q4h-MjM64syxn8yExPkZ4xGn4B0Jce4DptxIpIthJHOPpDXxNzGTI39DyEhH7qN_DFPI2BimLIoxeoz-ffGmM0PCD8_vdfHw7ev97V25__n9x-1uX1rOmrlkglPqTGeN6RirW8VpVxvrci3a1lK0Dcq6pcwJo1wrKTNbZalkVHCOqOrr4vOq25tBH6MfTXzSwXh9t9vrpQcghZIKzjSzn1b2GMOfU95Mjz5ZHIa8eTglTVnDQTEQ8mWUsq3kcgsio3JFbQwpRewuNijoJT190Jf09JKeBqlzenny4_Mnp3ZEd5n7H1cGblagM0Gbx-iTfviVFfgSrRBy8blbCcw3PufD62Q9Thadj2hn7YJ_0cY_BZi6nA</recordid><startdate>20121201</startdate><enddate>20121201</enddate><creator>Allard, Pierre-Marie</creator><creator>Leyssen, Pieter</creator><creator>Martin, Marie-Thérèse</creator><creator>Bourjot, Mélanie</creator><creator>Dumontet, Vincent</creator><creator>Eydoux, Cécilia</creator><creator>Guillemot, Jean-Claude</creator><creator>Canard, Bruno</creator><creator>Poullain, Cyril</creator><creator>Guéritte, Françoise</creator><creator>Litaudon, Marc</creator><general>Elsevier Ltd</general><general>Elsevier</general><scope>FBQ</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>7T7</scope><scope>7U9</scope><scope>8FD</scope><scope>C1K</scope><scope>F1W</scope><scope>FR3</scope><scope>H94</scope><scope>H95</scope><scope>H97</scope><scope>L.G</scope><scope>P64</scope><scope>1XC</scope><orcidid>https://orcid.org/0000-0003-3330-3457</orcidid><orcidid>https://orcid.org/0000-0003-4181-592X</orcidid><orcidid>https://orcid.org/0000-0002-0877-8234</orcidid><orcidid>https://orcid.org/0000-0003-3389-2191</orcidid><orcidid>https://orcid.org/0000-0003-4924-1991</orcidid></search><sort><creationdate>20121201</creationdate><title>Antiviral chlorinated daphnane diterpenoid orthoesters from the bark and wood of Trigonostemon cherrieri</title><author>Allard, Pierre-Marie ; Leyssen, Pieter ; Martin, Marie-Thérèse ; Bourjot, Mélanie ; Dumontet, Vincent ; Eydoux, Cécilia ; Guillemot, Jean-Claude ; Canard, Bruno ; Poullain, Cyril ; Guéritte, Françoise ; Litaudon, Marc</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c528t-26511dafcaaf223b951f3acdcaa6bbc1ec8e73b12d6a9db712a49c1721655ee93</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>Antiviral</topic><topic>Antiviral Agents - chemistry</topic><topic>Antiviral Agents - isolation & purification</topic><topic>Antiviral Agents - pharmacology</topic><topic>antiviral properties</topic><topic>bark</topic><topic>Chemical Sciences</topic><topic>Chikungunya virus</topic><topic>Chikungunya virus - drug effects</topic><topic>Chlorinated diterpenes</topic><topic>chlorination</topic><topic>Daphnane</topic><topic>Dengue virus</topic><topic>Dengue Virus - drug effects</topic><topic>Diterpenes - chemistry</topic><topic>Diterpenes - isolation & purification</topic><topic>Diterpenes - pharmacology</topic><topic>diterpenoids</topic><topic>Esters - chemistry</topic><topic>Esters - isolation & purification</topic><topic>Esters - pharmacology</topic><topic>Euphorbiaceae</topic><topic>Euphorbiaceae - chemistry</topic><topic>indigenous species</topic><topic>Microbial Sensitivity Tests</topic><topic>Molecular Conformation</topic><topic>Organic chemistry</topic><topic>pathogens</topic><topic>Plant Bark - chemistry</topic><topic>plants (botany)</topic><topic>Semliki Forest virus</topic><topic>Semliki forest virus - drug effects</topic><topic>Sindbis virus</topic><topic>Sindbis Virus - drug effects</topic><topic>Trigocherrin</topic><topic>Trigocherriolide</topic><topic>Trigonostemon cherrieri</topic><topic>wood</topic><topic>Wood - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Allard, Pierre-Marie</creatorcontrib><creatorcontrib>Leyssen, Pieter</creatorcontrib><creatorcontrib>Martin, Marie-Thérèse</creatorcontrib><creatorcontrib>Bourjot, Mélanie</creatorcontrib><creatorcontrib>Dumontet, Vincent</creatorcontrib><creatorcontrib>Eydoux, Cécilia</creatorcontrib><creatorcontrib>Guillemot, Jean-Claude</creatorcontrib><creatorcontrib>Canard, Bruno</creatorcontrib><creatorcontrib>Poullain, Cyril</creatorcontrib><creatorcontrib>Guéritte, Françoise</creatorcontrib><creatorcontrib>Litaudon, Marc</creatorcontrib><collection>AGRIS</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>Industrial and Applied Microbiology Abstracts (Microbiology A)</collection><collection>Virology and AIDS Abstracts</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>ASFA: Aquatic Sciences and Fisheries Abstracts</collection><collection>Engineering Research Database</collection><collection>AIDS and Cancer Research Abstracts</collection><collection>Aquatic Science & Fisheries Abstracts (ASFA) 1: Biological Sciences & Living Resources</collection><collection>Aquatic Science & Fisheries Abstracts (ASFA) 3: Aquatic Pollution & Environmental Quality</collection><collection>Aquatic Science & Fisheries Abstracts (ASFA) Professional</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>Hyper Article en Ligne (HAL)</collection><jtitle>Phytochemistry (Oxford)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Allard, Pierre-Marie</au><au>Leyssen, Pieter</au><au>Martin, Marie-Thérèse</au><au>Bourjot, Mélanie</au><au>Dumontet, Vincent</au><au>Eydoux, Cécilia</au><au>Guillemot, Jean-Claude</au><au>Canard, Bruno</au><au>Poullain, Cyril</au><au>Guéritte, Françoise</au><au>Litaudon, Marc</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Antiviral chlorinated daphnane diterpenoid orthoesters from the bark and wood of Trigonostemon cherrieri</atitle><jtitle>Phytochemistry (Oxford)</jtitle><addtitle>Phytochemistry</addtitle><date>2012-12-01</date><risdate>2012</risdate><volume>84</volume><spage>160</spage><epage>168</epage><pages>160-168</pages><issn>0031-9422</issn><eissn>1873-3700</eissn><abstract>The chemical investigation of the bark and wood of Trigonostemon cherrieri (Euphorbiaceae) led to the isolation of ten chlorinated daphnane diterpenoid orthoesters (DDO) named trigocherrins A–F (1–6) and trigocherriolides A–D (7–10). Several DDO exhibited strong antiviral activity against chinkungunya, Sindbis and Semliki forest virus. [Display omitted]
► Ten daphnane diterpenoid orthoesters were isolated from Trigonostemon cherrieri. ► They all possess a mono- or dichlorovinyl group on the daphnane core. ► They were isolated using bioassay-guided and LC/MS-guided fractionations. ► They are a class of non-nucleosidic inhibitor of the DENV NS5 RdRp. ► They showed strong antiviral activity against CHIK, Sindbis and Semliki forest virus.
The chemical study of the bark and the wood of Trigonostemon cherrieri, a rare endemic plant of New Caledonia, led to the isolation of a series of highly oxygenated daphnane diterpenoid orthoesters (DDO) bearing an uncommon chlorinated moiety: trigocherrins A–F and trigocherriolides A–D. Herein, we describe the isolation and structure elucidation of the DDO (trigocherrins B–F and trigocherriolides A–D). We also report the antiviral activity of trigocherrins A, B and F (1, 2 and 6) and trigocherriolides A, B and C (7–9) against various emerging pathogens: chikungunya virus (CHIKV), Sindbis virus (SINV), Semliki forest virus (SFV) and dengue virus (DENV).</abstract><cop>England</cop><pub>Elsevier Ltd</pub><pmid>22938995</pmid><doi>10.1016/j.phytochem.2012.07.023</doi><tpages>9</tpages><orcidid>https://orcid.org/0000-0003-3330-3457</orcidid><orcidid>https://orcid.org/0000-0003-4181-592X</orcidid><orcidid>https://orcid.org/0000-0002-0877-8234</orcidid><orcidid>https://orcid.org/0000-0003-3389-2191</orcidid><orcidid>https://orcid.org/0000-0003-4924-1991</orcidid></addata></record> |
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| subjects | Antiviral Antiviral Agents - chemistry Antiviral Agents - isolation & purification Antiviral Agents - pharmacology antiviral properties bark Chemical Sciences Chikungunya virus Chikungunya virus - drug effects Chlorinated diterpenes chlorination Daphnane Dengue virus Dengue Virus - drug effects Diterpenes - chemistry Diterpenes - isolation & purification Diterpenes - pharmacology diterpenoids Esters - chemistry Esters - isolation & purification Esters - pharmacology Euphorbiaceae Euphorbiaceae - chemistry indigenous species Microbial Sensitivity Tests Molecular Conformation Organic chemistry pathogens Plant Bark - chemistry plants (botany) Semliki Forest virus Semliki forest virus - drug effects Sindbis virus Sindbis Virus - drug effects Trigocherrin Trigocherriolide Trigonostemon cherrieri wood Wood - chemistry |
| title | Antiviral chlorinated daphnane diterpenoid orthoesters from the bark and wood of Trigonostemon cherrieri |
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