Brominated Aromatic Furanones and Related Esters from the Ascidian Synoicum sp
Nine new compounds, tris-aromatic furanones (1, 2, 3a, 3b, and 4) and related bis-aromatic diesters (5a, 5b, 6a, and 6b), are described from the ascidian Synoicum sp. collected off the coast of Chuja-do, Korea. The structures of these compounds, designated as cadiolides E and G–I (1–4) and synoilide...
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| Veröffentlicht in: | Journal of natural products (Washington, D.C.) D.C.), 2012-12, Vol.75 (12), p.2055-2061 |
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| container_issue | 12 |
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| container_title | Journal of natural products (Washington, D.C.) |
| container_volume | 75 |
| creator | Won, Tae Hyung Jeon, Ju-eun Kim, Seong-Hwan Lee, So-Hyoung Rho, Boon Jo Oh, Dong-Chan Oh, Ki-Bong Shin, Jongheon |
| description | Nine new compounds, tris-aromatic furanones (1, 2, 3a, 3b, and 4) and related bis-aromatic diesters (5a, 5b, 6a, and 6b), are described from the ascidian Synoicum sp. collected off the coast of Chuja-do, Korea. The structures of these compounds, designated as cadiolides E and G–I (1–4) and synoilides A and B (5 and 6), were determined by extensive spectroscopic analyses. The absolute configuration at the asymmetric center of cadiolide G (2) was assigned by ECD analysis. Of these new compounds, cadiolide I and the synoilides possess unprecedented carbon skeletons. Several of these compounds exhibited significant inhibition against diverse bacterial strains as well as moderate inhibition against the enzymes sortase A, isocitrate lyase, and Na+/K+-ATPase. |
| doi_str_mv | 10.1021/np3005562 |
| format | Article |
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The structures of these compounds, designated as cadiolides E and G–I (1–4) and synoilides A and B (5 and 6), were determined by extensive spectroscopic analyses. The absolute configuration at the asymmetric center of cadiolide G (2) was assigned by ECD analysis. Of these new compounds, cadiolide I and the synoilides possess unprecedented carbon skeletons. Several of these compounds exhibited significant inhibition against diverse bacterial strains as well as moderate inhibition against the enzymes sortase A, isocitrate lyase, and Na+/K+-ATPase.</description><identifier>ISSN: 0163-3864</identifier><identifier>EISSN: 1520-6025</identifier><identifier>DOI: 10.1021/np3005562</identifier><identifier>PMID: 23145909</identifier><language>eng</language><publisher>United States: American Chemical Society and American Society of Pharmacognosy</publisher><subject><![CDATA[Aminoacyltransferases - antagonists & inhibitors ; Animals ; Bacterial Proteins - antagonists & inhibitors ; Cysteine Endopeptidases ; Drug Screening Assays, Antitumor ; Esters ; Furans - chemistry ; Furans - isolation & purification ; Furans - pharmacology ; Hydrocarbons, Brominated - chemistry ; Hydrocarbons, Brominated - isolation & purification ; Hydrocarbons, Brominated - pharmacology ; Isocitrate Lyase - antagonists & inhibitors ; Microbial Sensitivity Tests ; Molecular Structure ; Republic of Korea ; Sodium-Potassium-Exchanging ATPase - antagonists & inhibitors ; Staphylococcus aureus - drug effects ; Urochordata - chemistry]]></subject><ispartof>Journal of natural products (Washington, D.C.), 2012-12, Vol.75 (12), p.2055-2061</ispartof><rights>Copyright © 2012 American Chemical Society and American Society of Pharmacognosy</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a315t-cf57beb56d11a69a0fdcb808bfedede0d90919441eb1b9a29fad3df416211bc73</citedby><cites>FETCH-LOGICAL-a315t-cf57beb56d11a69a0fdcb808bfedede0d90919441eb1b9a29fad3df416211bc73</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/np3005562$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/np3005562$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/23145909$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Won, Tae Hyung</creatorcontrib><creatorcontrib>Jeon, Ju-eun</creatorcontrib><creatorcontrib>Kim, Seong-Hwan</creatorcontrib><creatorcontrib>Lee, So-Hyoung</creatorcontrib><creatorcontrib>Rho, Boon Jo</creatorcontrib><creatorcontrib>Oh, Dong-Chan</creatorcontrib><creatorcontrib>Oh, Ki-Bong</creatorcontrib><creatorcontrib>Shin, Jongheon</creatorcontrib><title>Brominated Aromatic Furanones and Related Esters from the Ascidian Synoicum sp</title><title>Journal of natural products (Washington, D.C.)</title><addtitle>J. Nat. Prod</addtitle><description>Nine new compounds, tris-aromatic furanones (1, 2, 3a, 3b, and 4) and related bis-aromatic diesters (5a, 5b, 6a, and 6b), are described from the ascidian Synoicum sp. collected off the coast of Chuja-do, Korea. The structures of these compounds, designated as cadiolides E and G–I (1–4) and synoilides A and B (5 and 6), were determined by extensive spectroscopic analyses. The absolute configuration at the asymmetric center of cadiolide G (2) was assigned by ECD analysis. Of these new compounds, cadiolide I and the synoilides possess unprecedented carbon skeletons. Several of these compounds exhibited significant inhibition against diverse bacterial strains as well as moderate inhibition against the enzymes sortase A, isocitrate lyase, and Na+/K+-ATPase.</description><subject>Aminoacyltransferases - antagonists & inhibitors</subject><subject>Animals</subject><subject>Bacterial Proteins - antagonists & inhibitors</subject><subject>Cysteine Endopeptidases</subject><subject>Drug Screening Assays, Antitumor</subject><subject>Esters</subject><subject>Furans - chemistry</subject><subject>Furans - isolation & purification</subject><subject>Furans - pharmacology</subject><subject>Hydrocarbons, Brominated - chemistry</subject><subject>Hydrocarbons, Brominated - isolation & purification</subject><subject>Hydrocarbons, Brominated - pharmacology</subject><subject>Isocitrate Lyase - antagonists & inhibitors</subject><subject>Microbial Sensitivity Tests</subject><subject>Molecular Structure</subject><subject>Republic of Korea</subject><subject>Sodium-Potassium-Exchanging ATPase - antagonists & inhibitors</subject><subject>Staphylococcus aureus - drug effects</subject><subject>Urochordata - chemistry</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>eNptkE1Lw0AQhhdRbK0e_AOyF0EP0ZlsdtMca2lVKAp-nMN-YiTZ1N3k0H9vtLUnmcMMzMPLzEPIOcINQoq3fs0AOBfpARkjTyERkPJDMgYULGFTkY3ISYyfAMCg4MdklDLMeAHFmDzdhbapvOysobNhlF2l6bIP0rfeRiq9oS-2_l0vYmdDpG6gaPdh6SzqylTS09eNbyvdNzSuT8mRk3W0Z7s-Ie_Lxdv8IVk93z_OZ6tEMuRdoh3PlVVcGEQpCgnOaDWFqXLWDAVmuA2LLEOrUBUyLZw0zLgMRYqodM4m5Gqbuw7tV29jVzZV1LaupbdtH0tMc5ajEAgDer1FdWhjDNaV61A1MmxKhPJHX7nXN7AXu9heNdbsyT9fA3C5BaSO5WfbBz98-U_QN8ujdmg</recordid><startdate>20121228</startdate><enddate>20121228</enddate><creator>Won, Tae Hyung</creator><creator>Jeon, Ju-eun</creator><creator>Kim, Seong-Hwan</creator><creator>Lee, So-Hyoung</creator><creator>Rho, Boon Jo</creator><creator>Oh, Dong-Chan</creator><creator>Oh, Ki-Bong</creator><creator>Shin, Jongheon</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>20121228</creationdate><title>Brominated Aromatic Furanones and Related Esters from the Ascidian Synoicum sp</title><author>Won, Tae Hyung ; Jeon, Ju-eun ; Kim, Seong-Hwan ; Lee, So-Hyoung ; Rho, Boon Jo ; Oh, Dong-Chan ; Oh, Ki-Bong ; Shin, Jongheon</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a315t-cf57beb56d11a69a0fdcb808bfedede0d90919441eb1b9a29fad3df416211bc73</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>Aminoacyltransferases - antagonists & inhibitors</topic><topic>Animals</topic><topic>Bacterial Proteins - antagonists & inhibitors</topic><topic>Cysteine Endopeptidases</topic><topic>Drug Screening Assays, Antitumor</topic><topic>Esters</topic><topic>Furans - chemistry</topic><topic>Furans - isolation & purification</topic><topic>Furans - pharmacology</topic><topic>Hydrocarbons, Brominated - chemistry</topic><topic>Hydrocarbons, Brominated - isolation & purification</topic><topic>Hydrocarbons, Brominated - pharmacology</topic><topic>Isocitrate Lyase - antagonists & inhibitors</topic><topic>Microbial Sensitivity Tests</topic><topic>Molecular Structure</topic><topic>Republic of Korea</topic><topic>Sodium-Potassium-Exchanging ATPase - antagonists & inhibitors</topic><topic>Staphylococcus aureus - drug effects</topic><topic>Urochordata - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Won, Tae Hyung</creatorcontrib><creatorcontrib>Jeon, Ju-eun</creatorcontrib><creatorcontrib>Kim, Seong-Hwan</creatorcontrib><creatorcontrib>Lee, So-Hyoung</creatorcontrib><creatorcontrib>Rho, Boon Jo</creatorcontrib><creatorcontrib>Oh, Dong-Chan</creatorcontrib><creatorcontrib>Oh, Ki-Bong</creatorcontrib><creatorcontrib>Shin, Jongheon</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>Won, Tae Hyung</au><au>Jeon, Ju-eun</au><au>Kim, Seong-Hwan</au><au>Lee, So-Hyoung</au><au>Rho, Boon Jo</au><au>Oh, Dong-Chan</au><au>Oh, Ki-Bong</au><au>Shin, Jongheon</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Brominated Aromatic Furanones and Related Esters from the Ascidian Synoicum sp</atitle><jtitle>Journal of natural products (Washington, D.C.)</jtitle><addtitle>J. Nat. Prod</addtitle><date>2012-12-28</date><risdate>2012</risdate><volume>75</volume><issue>12</issue><spage>2055</spage><epage>2061</epage><pages>2055-2061</pages><issn>0163-3864</issn><eissn>1520-6025</eissn><abstract>Nine new compounds, tris-aromatic furanones (1, 2, 3a, 3b, and 4) and related bis-aromatic diesters (5a, 5b, 6a, and 6b), are described from the ascidian Synoicum sp. collected off the coast of Chuja-do, Korea. The structures of these compounds, designated as cadiolides E and G–I (1–4) and synoilides A and B (5 and 6), were determined by extensive spectroscopic analyses. The absolute configuration at the asymmetric center of cadiolide G (2) was assigned by ECD analysis. Of these new compounds, cadiolide I and the synoilides possess unprecedented carbon skeletons. Several of these compounds exhibited significant inhibition against diverse bacterial strains as well as moderate inhibition against the enzymes sortase A, isocitrate lyase, and Na+/K+-ATPase.</abstract><cop>United States</cop><pub>American Chemical Society and American Society of Pharmacognosy</pub><pmid>23145909</pmid><doi>10.1021/np3005562</doi><tpages>7</tpages></addata></record> |
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| subjects | Aminoacyltransferases - antagonists & inhibitors Animals Bacterial Proteins - antagonists & inhibitors Cysteine Endopeptidases Drug Screening Assays, Antitumor Esters Furans - chemistry Furans - isolation & purification Furans - pharmacology Hydrocarbons, Brominated - chemistry Hydrocarbons, Brominated - isolation & purification Hydrocarbons, Brominated - pharmacology Isocitrate Lyase - antagonists & inhibitors Microbial Sensitivity Tests Molecular Structure Republic of Korea Sodium-Potassium-Exchanging ATPase - antagonists & inhibitors Staphylococcus aureus - drug effects Urochordata - chemistry |
| title | Brominated Aromatic Furanones and Related Esters from the Ascidian Synoicum sp |
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