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Bioactive briarane diterpenoids from the South China Sea gorgonian Dichotella gemmacea
Six new briarane diterpenoids, gemmacolides T–Y (1–6), were isolated together with three known analogues from the South China Sea gorgonian Dichotella gemmacea. Compounds 3 and 6 showed potent growth inhibition towards tumor cell lines of A549 and MG63, being stronger than the positive control of ad...
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| Published in: | Bioorganic & medicinal chemistry letters 2012-07, Vol.22 (13), p.4368-4372 |
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| Main Authors: | , , , , , , , , |
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| cites | cdi_FETCH-LOGICAL-c443t-66dac012f76738b11cd9d927b4d7ae8c504d3ec830ce85e4f0d501fa747e383c3 |
| container_end_page | 4372 |
| container_issue | 13 |
| container_start_page | 4368 |
| container_title | Bioorganic & medicinal chemistry letters |
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| creator | Li, Cui La, Ming-Ping Tang, Hua Pan, Wei-Hua Sun, Peng Krohn, Karsten Yi, Yang-Hua Li, Ling Zhang, Wen |
| description | Six new briarane diterpenoids, gemmacolides T–Y (1–6), were isolated together with three known analogues from the South China Sea gorgonian Dichotella gemmacea. Compounds 3 and 6 showed potent growth inhibition towards tumor cell lines of A549 and MG63, being stronger than the positive control of adriamycin. These compounds also exhibited weak antimicrobial activity.
Six new briarane diterpenoids, gemmacolides T–Y (1–6), were isolated together with three known analogs, juncenolide J (7), praelolide (8), and junceellolide C (9), from the South China Sea gorgonian Dichotella gemmacea. The structures of the new compounds were elucidated by detailed spectroscopic analysis and comparison with reported data. The absolute configuration was suggested based on biosynthetic considerations. In an in vitro bioassay, compounds 3 and 6 showed potent growth inhibition towards tumor cell lines of A549 and MG63, being stronger than the positive control of adriamycin. These compounds also exhibited weak antimicrobial activity against the bacterium Escherichia coli and the fungi Microbotryum violaceum and Septoria tritici. |
| doi_str_mv | 10.1016/j.bmcl.2012.05.001 |
| format | article |
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Six new briarane diterpenoids, gemmacolides T–Y (1–6), were isolated together with three known analogs, juncenolide J (7), praelolide (8), and junceellolide C (9), from the South China Sea gorgonian Dichotella gemmacea. The structures of the new compounds were elucidated by detailed spectroscopic analysis and comparison with reported data. The absolute configuration was suggested based on biosynthetic considerations. In an in vitro bioassay, compounds 3 and 6 showed potent growth inhibition towards tumor cell lines of A549 and MG63, being stronger than the positive control of adriamycin. These compounds also exhibited weak antimicrobial activity against the bacterium Escherichia coli and the fungi Microbotryum violaceum and Septoria tritici.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/j.bmcl.2012.05.001</identifier><identifier>PMID: 22647719</identifier><language>eng</language><publisher>Amsterdam: Elsevier Ltd</publisher><subject>Absolute configuration ; Animals ; Anthozoa - chemistry ; Anti-Infective Agents - chemistry ; Anti-Infective Agents - isolation & purification ; Anti-Infective Agents - pharmacology ; anti-infective properties ; Apoptosis - drug effects ; bacteria ; bioassays ; Biological activity ; Biological and medical sciences ; Briarane diterpenoids ; Cell Line, Tumor ; chemistry ; China ; Dichotella gemmacea ; Diterpenes - chemistry ; Diterpenes - isolation & purification ; Diterpenes - pharmacology ; diterpenoids ; doxorubicin ; Escherichia coli ; Escherichia coli - drug effects ; fungi ; Fungi - drug effects ; General pharmacology ; Gorgonian ; growth retardation ; Heterocyclic Compounds, 4 or More Rings - chemistry ; Heterocyclic Compounds, 4 or More Rings - isolation & purification ; Heterocyclic Compounds, 4 or More Rings - pharmacology ; Humans ; Magnetic Resonance Spectroscopy ; Medical sciences ; Molecular Conformation ; Mycosphaerella graminicola ; Oceans and Seas ; Pharmacognosy. Homeopathy. Health food ; Pharmacology. Drug treatments ; spectroscopy ; Structure elucidation ; Ustilago violacea</subject><ispartof>Bioorganic & medicinal chemistry letters, 2012-07, Vol.22 (13), p.4368-4372</ispartof><rights>2012 Elsevier Ltd</rights><rights>2015 INIST-CNRS</rights><rights>Copyright © 2012 Elsevier Ltd. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c443t-66dac012f76738b11cd9d927b4d7ae8c504d3ec830ce85e4f0d501fa747e383c3</citedby><cites>FETCH-LOGICAL-c443t-66dac012f76738b11cd9d927b4d7ae8c504d3ec830ce85e4f0d501fa747e383c3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27923,27924</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=26093714$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/22647719$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Li, Cui</creatorcontrib><creatorcontrib>La, Ming-Ping</creatorcontrib><creatorcontrib>Tang, Hua</creatorcontrib><creatorcontrib>Pan, Wei-Hua</creatorcontrib><creatorcontrib>Sun, Peng</creatorcontrib><creatorcontrib>Krohn, Karsten</creatorcontrib><creatorcontrib>Yi, Yang-Hua</creatorcontrib><creatorcontrib>Li, Ling</creatorcontrib><creatorcontrib>Zhang, Wen</creatorcontrib><title>Bioactive briarane diterpenoids from the South China Sea gorgonian Dichotella gemmacea</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>Six new briarane diterpenoids, gemmacolides T–Y (1–6), were isolated together with three known analogues from the South China Sea gorgonian Dichotella gemmacea. Compounds 3 and 6 showed potent growth inhibition towards tumor cell lines of A549 and MG63, being stronger than the positive control of adriamycin. These compounds also exhibited weak antimicrobial activity.
Six new briarane diterpenoids, gemmacolides T–Y (1–6), were isolated together with three known analogs, juncenolide J (7), praelolide (8), and junceellolide C (9), from the South China Sea gorgonian Dichotella gemmacea. The structures of the new compounds were elucidated by detailed spectroscopic analysis and comparison with reported data. The absolute configuration was suggested based on biosynthetic considerations. In an in vitro bioassay, compounds 3 and 6 showed potent growth inhibition towards tumor cell lines of A549 and MG63, being stronger than the positive control of adriamycin. These compounds also exhibited weak antimicrobial activity against the bacterium Escherichia coli and the fungi Microbotryum violaceum and Septoria tritici.</description><subject>Absolute configuration</subject><subject>Animals</subject><subject>Anthozoa - chemistry</subject><subject>Anti-Infective Agents - chemistry</subject><subject>Anti-Infective Agents - isolation & purification</subject><subject>Anti-Infective Agents - pharmacology</subject><subject>anti-infective properties</subject><subject>Apoptosis - drug effects</subject><subject>bacteria</subject><subject>bioassays</subject><subject>Biological activity</subject><subject>Biological and medical sciences</subject><subject>Briarane diterpenoids</subject><subject>Cell Line, Tumor</subject><subject>chemistry</subject><subject>China</subject><subject>Dichotella gemmacea</subject><subject>Diterpenes - chemistry</subject><subject>Diterpenes - isolation & purification</subject><subject>Diterpenes - pharmacology</subject><subject>diterpenoids</subject><subject>doxorubicin</subject><subject>Escherichia coli</subject><subject>Escherichia coli - drug effects</subject><subject>fungi</subject><subject>Fungi - drug effects</subject><subject>General pharmacology</subject><subject>Gorgonian</subject><subject>growth retardation</subject><subject>Heterocyclic Compounds, 4 or More Rings - chemistry</subject><subject>Heterocyclic Compounds, 4 or More Rings - isolation & purification</subject><subject>Heterocyclic Compounds, 4 or More Rings - pharmacology</subject><subject>Humans</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Medical sciences</subject><subject>Molecular Conformation</subject><subject>Mycosphaerella graminicola</subject><subject>Oceans and Seas</subject><subject>Pharmacognosy. Homeopathy. Health food</subject><subject>Pharmacology. Drug treatments</subject><subject>spectroscopy</subject><subject>Structure elucidation</subject><subject>Ustilago violacea</subject><issn>0960-894X</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><recordid>eNqN0E2P0zAQBmALgdiy8Ac4QC5IXJIdfyR2JC5QPnallTiURdwsx560rpK42OlK--9x1AI3xMmS9czMq5eQlxQqCrS52lfdaIeKAWUV1BUAfURWVDSi5ALqx2QFbQOlasWPC_IspX0GAoR4Si4Ya4SUtF2R7x98MHb291h00ZtoJiycnzEecArepaKPYSzmHRabcJx3xXrnJ1Ns0BTbELdh8mYqPnq7CzMOQ_7EcTQWzXPypDdDwhfn95Lcff70bX1d3n79crN-f1taIfhcNo0zNsfvZSO56ii1rnUtk51w0qCyNQjH0SoOFlWNogdXA-2NFBK54pZfkrenvYcYfh4xzXr0yS5RJgzHpClwoZgCyf-DMlCsVbTNlJ2ojSGliL0-RD-a-JCRXqrXe71Ur5fqNdQ6N5uHXp33H7sR3Z-R311n8OYMTLJm6HPX1qe_roGWSyqye31yvQnabGM2d5t8qV6u5Igsi3cngbnae49RJ-txsuh8RDtrF_y_kv4CIBOqVQ</recordid><startdate>20120701</startdate><enddate>20120701</enddate><creator>Li, Cui</creator><creator>La, Ming-Ping</creator><creator>Tang, Hua</creator><creator>Pan, Wei-Hua</creator><creator>Sun, Peng</creator><creator>Krohn, Karsten</creator><creator>Yi, Yang-Hua</creator><creator>Li, Ling</creator><creator>Zhang, Wen</creator><general>Elsevier Ltd</general><general>Elsevier</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>7QO</scope><scope>8FD</scope><scope>FR3</scope><scope>M7N</scope><scope>P64</scope></search><sort><creationdate>20120701</creationdate><title>Bioactive briarane diterpenoids from the South China Sea gorgonian Dichotella gemmacea</title><author>Li, Cui ; La, Ming-Ping ; Tang, Hua ; Pan, Wei-Hua ; Sun, Peng ; Krohn, Karsten ; Yi, Yang-Hua ; Li, Ling ; Zhang, Wen</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c443t-66dac012f76738b11cd9d927b4d7ae8c504d3ec830ce85e4f0d501fa747e383c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>Absolute configuration</topic><topic>Animals</topic><topic>Anthozoa - chemistry</topic><topic>Anti-Infective Agents - chemistry</topic><topic>Anti-Infective Agents - isolation & purification</topic><topic>Anti-Infective Agents - pharmacology</topic><topic>anti-infective properties</topic><topic>Apoptosis - drug effects</topic><topic>bacteria</topic><topic>bioassays</topic><topic>Biological activity</topic><topic>Biological and medical sciences</topic><topic>Briarane diterpenoids</topic><topic>Cell Line, Tumor</topic><topic>chemistry</topic><topic>China</topic><topic>Dichotella gemmacea</topic><topic>Diterpenes - chemistry</topic><topic>Diterpenes - isolation & purification</topic><topic>Diterpenes - pharmacology</topic><topic>diterpenoids</topic><topic>doxorubicin</topic><topic>Escherichia coli</topic><topic>Escherichia coli - drug effects</topic><topic>fungi</topic><topic>Fungi - drug effects</topic><topic>General pharmacology</topic><topic>Gorgonian</topic><topic>growth retardation</topic><topic>Heterocyclic Compounds, 4 or More Rings - chemistry</topic><topic>Heterocyclic Compounds, 4 or More Rings - isolation & purification</topic><topic>Heterocyclic Compounds, 4 or More Rings - pharmacology</topic><topic>Humans</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Medical sciences</topic><topic>Molecular Conformation</topic><topic>Mycosphaerella graminicola</topic><topic>Oceans and Seas</topic><topic>Pharmacognosy. Homeopathy. Health food</topic><topic>Pharmacology. Drug treatments</topic><topic>spectroscopy</topic><topic>Structure elucidation</topic><topic>Ustilago violacea</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Li, Cui</creatorcontrib><creatorcontrib>La, Ming-Ping</creatorcontrib><creatorcontrib>Tang, Hua</creatorcontrib><creatorcontrib>Pan, Wei-Hua</creatorcontrib><creatorcontrib>Sun, Peng</creatorcontrib><creatorcontrib>Krohn, Karsten</creatorcontrib><creatorcontrib>Yi, Yang-Hua</creatorcontrib><creatorcontrib>Li, Ling</creatorcontrib><creatorcontrib>Zhang, Wen</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>Biotechnology Research Abstracts</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Algology Mycology and Protozoology Abstracts (Microbiology C)</collection><collection>Biotechnology and BioEngineering Abstracts</collection><jtitle>Bioorganic & medicinal chemistry letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Li, Cui</au><au>La, Ming-Ping</au><au>Tang, Hua</au><au>Pan, Wei-Hua</au><au>Sun, Peng</au><au>Krohn, Karsten</au><au>Yi, Yang-Hua</au><au>Li, Ling</au><au>Zhang, Wen</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Bioactive briarane diterpenoids from the South China Sea gorgonian Dichotella gemmacea</atitle><jtitle>Bioorganic & medicinal chemistry letters</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2012-07-01</date><risdate>2012</risdate><volume>22</volume><issue>13</issue><spage>4368</spage><epage>4372</epage><pages>4368-4372</pages><issn>0960-894X</issn><eissn>1464-3405</eissn><abstract>Six new briarane diterpenoids, gemmacolides T–Y (1–6), were isolated together with three known analogues from the South China Sea gorgonian Dichotella gemmacea. Compounds 3 and 6 showed potent growth inhibition towards tumor cell lines of A549 and MG63, being stronger than the positive control of adriamycin. These compounds also exhibited weak antimicrobial activity.
Six new briarane diterpenoids, gemmacolides T–Y (1–6), were isolated together with three known analogs, juncenolide J (7), praelolide (8), and junceellolide C (9), from the South China Sea gorgonian Dichotella gemmacea. The structures of the new compounds were elucidated by detailed spectroscopic analysis and comparison with reported data. The absolute configuration was suggested based on biosynthetic considerations. In an in vitro bioassay, compounds 3 and 6 showed potent growth inhibition towards tumor cell lines of A549 and MG63, being stronger than the positive control of adriamycin. These compounds also exhibited weak antimicrobial activity against the bacterium Escherichia coli and the fungi Microbotryum violaceum and Septoria tritici.</abstract><cop>Amsterdam</cop><pub>Elsevier Ltd</pub><pmid>22647719</pmid><doi>10.1016/j.bmcl.2012.05.001</doi><tpages>5</tpages></addata></record> |
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| subjects | Absolute configuration Animals Anthozoa - chemistry Anti-Infective Agents - chemistry Anti-Infective Agents - isolation & purification Anti-Infective Agents - pharmacology anti-infective properties Apoptosis - drug effects bacteria bioassays Biological activity Biological and medical sciences Briarane diterpenoids Cell Line, Tumor chemistry China Dichotella gemmacea Diterpenes - chemistry Diterpenes - isolation & purification Diterpenes - pharmacology diterpenoids doxorubicin Escherichia coli Escherichia coli - drug effects fungi Fungi - drug effects General pharmacology Gorgonian growth retardation Heterocyclic Compounds, 4 or More Rings - chemistry Heterocyclic Compounds, 4 or More Rings - isolation & purification Heterocyclic Compounds, 4 or More Rings - pharmacology Humans Magnetic Resonance Spectroscopy Medical sciences Molecular Conformation Mycosphaerella graminicola Oceans and Seas Pharmacognosy. Homeopathy. Health food Pharmacology. Drug treatments spectroscopy Structure elucidation Ustilago violacea |
| title | Bioactive briarane diterpenoids from the South China Sea gorgonian Dichotella gemmacea |
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