Rearranged Diterpenes and Norditerpenes from Three Australian Goniobranchus Mollusks
Three new norditerpenes (1, 6, and 7) and four diterpenes (2–5) with extensively rearranged carbon skeletons have been characterized from Australian nudibranchs. The relative configuration of the cyclopropyl-containing verrielactone (1) from Goniobranchus verrieri was suggested by spectroscopic anal...
Gespeichert in:
| Veröffentlicht in: | Journal of natural products (Washington, D.C.) D.C.), 2016-03, Vol.79 (3), p.477-483 |
|---|---|
| Hauptverfasser: | , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 483 |
|---|---|
| container_issue | 3 |
| container_start_page | 477 |
| container_title | Journal of natural products (Washington, D.C.) |
| container_volume | 79 |
| creator | White, Andrew M Pierens, Gregory K Forster, Louise C Winters, Anne E Cheney, Karen L Garson, Mary J |
| description | Three new norditerpenes (1, 6, and 7) and four diterpenes (2–5) with extensively rearranged carbon skeletons have been characterized from Australian nudibranchs. The relative configuration of the cyclopropyl-containing verrielactone (1) from Goniobranchus verrieri was suggested by spectroscopic analysis at 500 MHz informed by a combination of molecular modeling and DFT calculations. The nudibranchs G. splendidus and G. cf. splendidus provided 2–7, for which the structures and stereochemistry were deduced by 2D NMR studies at either 500 or 700 MHz. Each of the seven terpenoids exhibited a carbon skeleton modified from one of the tetrahydroaplysulphurin, spongionellin, or gracilane series of terpenes. A biosynthetic pathway to terpenes 1–7 from spongialactone is proposed. |
| doi_str_mv | 10.1021/acs.jnatprod.5b00866 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_1776089819</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>1776089819</sourcerecordid><originalsourceid>FETCH-LOGICAL-a348t-ae45fd41d743e7fad9a4d84deacd3de4d554d1f9e46f5c48dbf4276cab259ef43</originalsourceid><addsrcrecordid>eNp9kMtOwzAQRS0EouXxBwhlySbFdmzHWVYFClIBCZW15cRjmpLYxU4W_D2BtrBjNdLonjuag9AFwROCKbnWVZysne42wZsJLzGWQhygMeEUpwJTfojGmIgszaRgI3QS4xpjnOGCH6MRFaKQNKdjtHwBHYJ2b2CSm7qDsAEHMdHOJE8-mL-NDb5NlqsAkEz72AXd1Nolc-9qXw58tepj8uibpo_v8QwdWd1EON_NU_R6d7uc3aeL5_nDbLpIdcZkl2pg3BpGTM4yyK02hWZGMgO6MpkBZjhnhtgCmLC8YtKUltFcVLqkvADLslN0te0dHHz0EDvV1rGCptEOfB8VyXOBZSFJMUTZNloFH2MAqzahbnX4VASrb59q8Kn2PtXO54Bd7i70ZQvmF9oLHAJ4G_jBfR_c8PD_nV-FSIfs</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1776089819</pqid></control><display><type>article</type><title>Rearranged Diterpenes and Norditerpenes from Three Australian Goniobranchus Mollusks</title><source>MEDLINE</source><source>American Chemical Society Journals</source><creator>White, Andrew M ; Pierens, Gregory K ; Forster, Louise C ; Winters, Anne E ; Cheney, Karen L ; Garson, Mary J</creator><creatorcontrib>White, Andrew M ; Pierens, Gregory K ; Forster, Louise C ; Winters, Anne E ; Cheney, Karen L ; Garson, Mary J</creatorcontrib><description>Three new norditerpenes (1, 6, and 7) and four diterpenes (2–5) with extensively rearranged carbon skeletons have been characterized from Australian nudibranchs. The relative configuration of the cyclopropyl-containing verrielactone (1) from Goniobranchus verrieri was suggested by spectroscopic analysis at 500 MHz informed by a combination of molecular modeling and DFT calculations. The nudibranchs G. splendidus and G. cf. splendidus provided 2–7, for which the structures and stereochemistry were deduced by 2D NMR studies at either 500 or 700 MHz. Each of the seven terpenoids exhibited a carbon skeleton modified from one of the tetrahydroaplysulphurin, spongionellin, or gracilane series of terpenes. A biosynthetic pathway to terpenes 1–7 from spongialactone is proposed.</description><identifier>ISSN: 0163-3864</identifier><identifier>EISSN: 1520-6025</identifier><identifier>DOI: 10.1021/acs.jnatprod.5b00866</identifier><identifier>PMID: 26698272</identifier><language>eng</language><publisher>United States: American Chemical Society and American Society of Pharmacognosy</publisher><subject>Animals ; Australia ; Diterpenes - chemistry ; Diterpenes - isolation & purification ; Gastropoda - chemistry ; Molecular Structure ; Nuclear Magnetic Resonance, Biomolecular ; Terpenes - chemistry</subject><ispartof>Journal of natural products (Washington, D.C.), 2016-03, Vol.79 (3), p.477-483</ispartof><rights>Copyright © 2015 American Chemical Society and American Society of Pharmacognosy</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a348t-ae45fd41d743e7fad9a4d84deacd3de4d554d1f9e46f5c48dbf4276cab259ef43</citedby><cites>FETCH-LOGICAL-a348t-ae45fd41d743e7fad9a4d84deacd3de4d554d1f9e46f5c48dbf4276cab259ef43</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/acs.jnatprod.5b00866$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acs.jnatprod.5b00866$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/26698272$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>White, Andrew M</creatorcontrib><creatorcontrib>Pierens, Gregory K</creatorcontrib><creatorcontrib>Forster, Louise C</creatorcontrib><creatorcontrib>Winters, Anne E</creatorcontrib><creatorcontrib>Cheney, Karen L</creatorcontrib><creatorcontrib>Garson, Mary J</creatorcontrib><title>Rearranged Diterpenes and Norditerpenes from Three Australian Goniobranchus Mollusks</title><title>Journal of natural products (Washington, D.C.)</title><addtitle>J. Nat. Prod</addtitle><description>Three new norditerpenes (1, 6, and 7) and four diterpenes (2–5) with extensively rearranged carbon skeletons have been characterized from Australian nudibranchs. The relative configuration of the cyclopropyl-containing verrielactone (1) from Goniobranchus verrieri was suggested by spectroscopic analysis at 500 MHz informed by a combination of molecular modeling and DFT calculations. The nudibranchs G. splendidus and G. cf. splendidus provided 2–7, for which the structures and stereochemistry were deduced by 2D NMR studies at either 500 or 700 MHz. Each of the seven terpenoids exhibited a carbon skeleton modified from one of the tetrahydroaplysulphurin, spongionellin, or gracilane series of terpenes. A biosynthetic pathway to terpenes 1–7 from spongialactone is proposed.</description><subject>Animals</subject><subject>Australia</subject><subject>Diterpenes - chemistry</subject><subject>Diterpenes - isolation & purification</subject><subject>Gastropoda - chemistry</subject><subject>Molecular Structure</subject><subject>Nuclear Magnetic Resonance, Biomolecular</subject><subject>Terpenes - chemistry</subject><issn>0163-3864</issn><issn>1520-6025</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kMtOwzAQRS0EouXxBwhlySbFdmzHWVYFClIBCZW15cRjmpLYxU4W_D2BtrBjNdLonjuag9AFwROCKbnWVZysne42wZsJLzGWQhygMeEUpwJTfojGmIgszaRgI3QS4xpjnOGCH6MRFaKQNKdjtHwBHYJ2b2CSm7qDsAEHMdHOJE8-mL-NDb5NlqsAkEz72AXd1Nolc-9qXw58tepj8uibpo_v8QwdWd1EON_NU_R6d7uc3aeL5_nDbLpIdcZkl2pg3BpGTM4yyK02hWZGMgO6MpkBZjhnhtgCmLC8YtKUltFcVLqkvADLslN0te0dHHz0EDvV1rGCptEOfB8VyXOBZSFJMUTZNloFH2MAqzahbnX4VASrb59q8Kn2PtXO54Bd7i70ZQvmF9oLHAJ4G_jBfR_c8PD_nV-FSIfs</recordid><startdate>20160325</startdate><enddate>20160325</enddate><creator>White, Andrew M</creator><creator>Pierens, Gregory K</creator><creator>Forster, Louise C</creator><creator>Winters, Anne E</creator><creator>Cheney, Karen L</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></search><sort><creationdate>20160325</creationdate><title>Rearranged Diterpenes and Norditerpenes from Three Australian Goniobranchus Mollusks</title><author>White, Andrew M ; Pierens, Gregory K ; Forster, Louise C ; Winters, Anne E ; Cheney, Karen L ; Garson, Mary J</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a348t-ae45fd41d743e7fad9a4d84deacd3de4d554d1f9e46f5c48dbf4276cab259ef43</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>Animals</topic><topic>Australia</topic><topic>Diterpenes - chemistry</topic><topic>Diterpenes - isolation & purification</topic><topic>Gastropoda - chemistry</topic><topic>Molecular Structure</topic><topic>Nuclear Magnetic Resonance, Biomolecular</topic><topic>Terpenes - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>White, Andrew M</creatorcontrib><creatorcontrib>Pierens, Gregory K</creatorcontrib><creatorcontrib>Forster, Louise C</creatorcontrib><creatorcontrib>Winters, Anne E</creatorcontrib><creatorcontrib>Cheney, Karen L</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><jtitle>Journal of natural products (Washington, D.C.)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>White, Andrew M</au><au>Pierens, Gregory K</au><au>Forster, Louise C</au><au>Winters, Anne E</au><au>Cheney, Karen L</au><au>Garson, Mary J</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Rearranged Diterpenes and Norditerpenes from Three Australian Goniobranchus Mollusks</atitle><jtitle>Journal of natural products (Washington, D.C.)</jtitle><addtitle>J. Nat. Prod</addtitle><date>2016-03-25</date><risdate>2016</risdate><volume>79</volume><issue>3</issue><spage>477</spage><epage>483</epage><pages>477-483</pages><issn>0163-3864</issn><eissn>1520-6025</eissn><abstract>Three new norditerpenes (1, 6, and 7) and four diterpenes (2–5) with extensively rearranged carbon skeletons have been characterized from Australian nudibranchs. The relative configuration of the cyclopropyl-containing verrielactone (1) from Goniobranchus verrieri was suggested by spectroscopic analysis at 500 MHz informed by a combination of molecular modeling and DFT calculations. The nudibranchs G. splendidus and G. cf. splendidus provided 2–7, for which the structures and stereochemistry were deduced by 2D NMR studies at either 500 or 700 MHz. Each of the seven terpenoids exhibited a carbon skeleton modified from one of the tetrahydroaplysulphurin, spongionellin, or gracilane series of terpenes. A biosynthetic pathway to terpenes 1–7 from spongialactone is proposed.</abstract><cop>United States</cop><pub>American Chemical Society and American Society of Pharmacognosy</pub><pmid>26698272</pmid><doi>10.1021/acs.jnatprod.5b00866</doi><tpages>7</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0163-3864 |
| ispartof | Journal of natural products (Washington, D.C.), 2016-03, Vol.79 (3), p.477-483 |
| issn | 0163-3864 1520-6025 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_1776089819 |
| source | MEDLINE; American Chemical Society Journals |
| subjects | Animals Australia Diterpenes - chemistry Diterpenes - isolation & purification Gastropoda - chemistry Molecular Structure Nuclear Magnetic Resonance, Biomolecular Terpenes - chemistry |
| title | Rearranged Diterpenes and Norditerpenes from Three Australian Goniobranchus Mollusks |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-03T06%3A56%3A13IST&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=Rearranged%20Diterpenes%20and%20Norditerpenes%20from%20Three%20Australian%20Goniobranchus%20Mollusks&rft.jtitle=Journal%20of%20natural%20products%20(Washington,%20D.C.)&rft.au=White,%20Andrew%20M&rft.date=2016-03-25&rft.volume=79&rft.issue=3&rft.spage=477&rft.epage=483&rft.pages=477-483&rft.issn=0163-3864&rft.eissn=1520-6025&rft_id=info:doi/10.1021/acs.jnatprod.5b00866&rft_dat=%3Cproquest_cross%3E1776089819%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=1776089819&rft_id=info:pmid/26698272&rfr_iscdi=true |