Isolation of Thuridillins D–F, Diterpene Metabolites from the Australian Sacoglossan Mollusk Thuridilla splendens; Relative Configuration of the Epoxylactone Ring
This first chemical study of the sacoglossan mollusk Thuridilla splendens from Mooloolaba, South East Queensland, has resulted in the isolation of three new metabolites, thuridillins D–F (1–3), and one known metabolite, thuridillin A (4). Thuridillin D (1) was isolated by conventional flash chromato...
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| Veröffentlicht in: | Journal of natural products (Washington, D.C.) D.C.), 2012-09, Vol.75 (9), p.1618-1624 |
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| container_title | Journal of natural products (Washington, D.C.) |
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| creator | Somerville, Michael J Katavic, Peter L Lambert, Lynette K Pierens, Gregory K Blanchfield, Joanne T Cimino, Guido Mollo, Ernesto Gavagnin, Margherita Banwell, Martin G Garson, Mary J |
| description | This first chemical study of the sacoglossan mollusk Thuridilla splendens from Mooloolaba, South East Queensland, has resulted in the isolation of three new metabolites, thuridillins D–F (1–3), and one known metabolite, thuridillin A (4). Thuridillin D (1) was isolated by conventional flash chromatography on silica gel, while a mixture of thuridillins E (2) and F (3) was obtained by PTLC on AgNO3-impregnated silica gel. Thuridillins D–F were determined to be structurally related to thuridillin B (5); 1 possessed a hydroxy group at C-11, and 2 and 3 were Δ10,11- and Δ11,12-isomers, respectively. HSQC-HECADE NMR data, together with conformational analysis, NOESY experiments, and 1H–1H coupling studies enabled assignment of the individual relative configurations of the epoxylactone, the 2,5-diacetoxy-2,5-dihydrofuran, and cyclohexyl moieties within thuridillin D (1). |
| doi_str_mv | 10.1021/np300442s |
| format | Article |
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Thuridillin D (1) was isolated by conventional flash chromatography on silica gel, while a mixture of thuridillins E (2) and F (3) was obtained by PTLC on AgNO3-impregnated silica gel. Thuridillins D–F were determined to be structurally related to thuridillin B (5); 1 possessed a hydroxy group at C-11, and 2 and 3 were Δ10,11- and Δ11,12-isomers, respectively. HSQC-HECADE NMR data, together with conformational analysis, NOESY experiments, and 1H–1H coupling studies enabled assignment of the individual relative configurations of the epoxylactone, the 2,5-diacetoxy-2,5-dihydrofuran, and cyclohexyl moieties within thuridillin D (1).</description><identifier>ISSN: 0163-3864</identifier><identifier>EISSN: 1520-6025</identifier><identifier>DOI: 10.1021/np300442s</identifier><identifier>PMID: 22988884</identifier><language>eng</language><publisher>United States: American Chemical Society and American Society of Pharmacognosy</publisher><subject>Animals ; Australia ; Diterpenes - chemistry ; Diterpenes - isolation & purification ; Epoxy Compounds - chemistry ; Lactones - chemistry ; Magnetic Resonance Spectroscopy ; Molecular Structure ; Mollusca ; Mollusca - chemistry ; Nuclear Magnetic Resonance, Biomolecular - methods</subject><ispartof>Journal of natural products (Washington, D.C.), 2012-09, Vol.75 (9), p.1618-1624</ispartof><rights>Copyright © 2012 American Chemical Society and American Society of Pharmacognosy</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a348t-8f91fe6d50b1e89d7b00d18691daf48d9c3799f3048808f93c9aaacda451007f3</citedby><cites>FETCH-LOGICAL-a348t-8f91fe6d50b1e89d7b00d18691daf48d9c3799f3048808f93c9aaacda451007f3</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/np300442s$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/np300442s$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2763,27075,27923,27924,56737,56787</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/22988884$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Somerville, Michael J</creatorcontrib><creatorcontrib>Katavic, Peter L</creatorcontrib><creatorcontrib>Lambert, Lynette K</creatorcontrib><creatorcontrib>Pierens, Gregory K</creatorcontrib><creatorcontrib>Blanchfield, Joanne T</creatorcontrib><creatorcontrib>Cimino, Guido</creatorcontrib><creatorcontrib>Mollo, Ernesto</creatorcontrib><creatorcontrib>Gavagnin, Margherita</creatorcontrib><creatorcontrib>Banwell, Martin G</creatorcontrib><creatorcontrib>Garson, Mary J</creatorcontrib><title>Isolation of Thuridillins D–F, Diterpene Metabolites from the Australian Sacoglossan Mollusk Thuridilla splendens; Relative Configuration of the Epoxylactone Ring</title><title>Journal of natural products (Washington, D.C.)</title><addtitle>J. Nat. Prod</addtitle><description>This first chemical study of the sacoglossan mollusk Thuridilla splendens from Mooloolaba, South East Queensland, has resulted in the isolation of three new metabolites, thuridillins D–F (1–3), and one known metabolite, thuridillin A (4). Thuridillin D (1) was isolated by conventional flash chromatography on silica gel, while a mixture of thuridillins E (2) and F (3) was obtained by PTLC on AgNO3-impregnated silica gel. Thuridillins D–F were determined to be structurally related to thuridillin B (5); 1 possessed a hydroxy group at C-11, and 2 and 3 were Δ10,11- and Δ11,12-isomers, respectively. HSQC-HECADE NMR data, together with conformational analysis, NOESY experiments, and 1H–1H coupling studies enabled assignment of the individual relative configurations of the epoxylactone, the 2,5-diacetoxy-2,5-dihydrofuran, and cyclohexyl moieties within thuridillin D (1).</description><subject>Animals</subject><subject>Australia</subject><subject>Diterpenes - chemistry</subject><subject>Diterpenes - isolation & purification</subject><subject>Epoxy Compounds - chemistry</subject><subject>Lactones - chemistry</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Molecular Structure</subject><subject>Mollusca</subject><subject>Mollusca - chemistry</subject><subject>Nuclear Magnetic Resonance, Biomolecular - methods</subject><issn>0163-3864</issn><issn>1520-6025</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkcFu1DAQhi0EokvhwAsgX5BAIjCOncQWp2rbQqVWSKWcI29sb128dvAkiN54B16BJ-NJ8GrLckFiLh5Ln74ZzU_IUwavGdTsTRw5gBA13iML1tRQtVA398kCWMsrLltxQB4h3gAAB9U8JAd1rWQpsSA_zzAFPfkUaXL06nrO3vgQfER6_Ov7j9NX9NhPNo82WnphJ71KofyRupw2dLq29GjGKevgdaQf9ZDWISGW_iKFMOPnv0ZNcQw2GhvxLb2025lfLV2m6Px6zvsNtsqTMX27DXqYUhl66eP6MXngdED75O49JJ9OT66W76vzD-_OlkfnleZCTpV0ijnbmgZWzEpluhWAYbJVzGgnpFED75RyHISUUGA-KK31YLRoGEDn-CF5sfOOOX2ZLU79xuNgy_LRphl71squ7SSA_D8Kkgne1fUWfblDh1xuk63rx-w3Ot8WqN_m1-_zK-yzO-282lizJ_8EVoDnO0AP2N-kOcdykH-IfgNodaWW</recordid><startdate>20120928</startdate><enddate>20120928</enddate><creator>Somerville, Michael J</creator><creator>Katavic, Peter L</creator><creator>Lambert, Lynette K</creator><creator>Pierens, Gregory K</creator><creator>Blanchfield, Joanne T</creator><creator>Cimino, Guido</creator><creator>Mollo, Ernesto</creator><creator>Gavagnin, Margherita</creator><creator>Banwell, Martin G</creator><creator>Garson, Mary J</creator><general>American Chemical Society and American Society of Pharmacognosy</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>7X8</scope><scope>7TN</scope><scope>F1W</scope><scope>H95</scope><scope>L.G</scope></search><sort><creationdate>20120928</creationdate><title>Isolation of Thuridillins D–F, Diterpene Metabolites from the Australian Sacoglossan Mollusk Thuridilla splendens; Relative Configuration of the Epoxylactone Ring</title><author>Somerville, Michael J ; Katavic, Peter L ; Lambert, Lynette K ; Pierens, Gregory K ; Blanchfield, Joanne T ; Cimino, Guido ; Mollo, Ernesto ; Gavagnin, Margherita ; Banwell, Martin G ; Garson, Mary J</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a348t-8f91fe6d50b1e89d7b00d18691daf48d9c3799f3048808f93c9aaacda451007f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>Animals</topic><topic>Australia</topic><topic>Diterpenes - chemistry</topic><topic>Diterpenes - isolation & purification</topic><topic>Epoxy Compounds - chemistry</topic><topic>Lactones - chemistry</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Molecular Structure</topic><topic>Mollusca</topic><topic>Mollusca - chemistry</topic><topic>Nuclear Magnetic Resonance, Biomolecular - methods</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Somerville, Michael J</creatorcontrib><creatorcontrib>Katavic, Peter L</creatorcontrib><creatorcontrib>Lambert, Lynette K</creatorcontrib><creatorcontrib>Pierens, Gregory K</creatorcontrib><creatorcontrib>Blanchfield, Joanne T</creatorcontrib><creatorcontrib>Cimino, Guido</creatorcontrib><creatorcontrib>Mollo, Ernesto</creatorcontrib><creatorcontrib>Gavagnin, Margherita</creatorcontrib><creatorcontrib>Banwell, Martin G</creatorcontrib><creatorcontrib>Garson, Mary J</creatorcontrib><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>Oceanic Abstracts</collection><collection>ASFA: Aquatic Sciences and Fisheries Abstracts</collection><collection>Aquatic Science & Fisheries Abstracts (ASFA) 1: Biological Sciences & Living Resources</collection><collection>Aquatic Science & Fisheries Abstracts (ASFA) Professional</collection><jtitle>Journal of natural products (Washington, D.C.)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Somerville, Michael J</au><au>Katavic, Peter L</au><au>Lambert, Lynette K</au><au>Pierens, Gregory K</au><au>Blanchfield, Joanne T</au><au>Cimino, Guido</au><au>Mollo, Ernesto</au><au>Gavagnin, Margherita</au><au>Banwell, Martin G</au><au>Garson, Mary J</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Isolation of Thuridillins D–F, Diterpene Metabolites from the Australian Sacoglossan Mollusk Thuridilla splendens; 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Nat. Prod</addtitle><date>2012-09-28</date><risdate>2012</risdate><volume>75</volume><issue>9</issue><spage>1618</spage><epage>1624</epage><pages>1618-1624</pages><issn>0163-3864</issn><eissn>1520-6025</eissn><abstract>This first chemical study of the sacoglossan mollusk Thuridilla splendens from Mooloolaba, South East Queensland, has resulted in the isolation of three new metabolites, thuridillins D–F (1–3), and one known metabolite, thuridillin A (4). Thuridillin D (1) was isolated by conventional flash chromatography on silica gel, while a mixture of thuridillins E (2) and F (3) was obtained by PTLC on AgNO3-impregnated silica gel. Thuridillins D–F were determined to be structurally related to thuridillin B (5); 1 possessed a hydroxy group at C-11, and 2 and 3 were Δ10,11- and Δ11,12-isomers, respectively. HSQC-HECADE NMR data, together with conformational analysis, NOESY experiments, and 1H–1H coupling studies enabled assignment of the individual relative configurations of the epoxylactone, the 2,5-diacetoxy-2,5-dihydrofuran, and cyclohexyl moieties within thuridillin D (1).</abstract><cop>United States</cop><pub>American Chemical Society and American Society of Pharmacognosy</pub><pmid>22988884</pmid><doi>10.1021/np300442s</doi><tpages>7</tpages></addata></record> |
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| ispartof | Journal of natural products (Washington, D.C.), 2012-09, Vol.75 (9), p.1618-1624 |
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| source | MEDLINE; ACS Publications |
| subjects | Animals Australia Diterpenes - chemistry Diterpenes - isolation & purification Epoxy Compounds - chemistry Lactones - chemistry Magnetic Resonance Spectroscopy Molecular Structure Mollusca Mollusca - chemistry Nuclear Magnetic Resonance, Biomolecular - methods |
| title | Isolation of Thuridillins D–F, Diterpene Metabolites from the Australian Sacoglossan Mollusk Thuridilla splendens; Relative Configuration of the Epoxylactone Ring |
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