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Denigrins A-C: new antitubercular 3,4-diarylpyrrole alkaloids from Dendrilla nigra
Chemical diversity is vital to antitubercular drug discovery as it ensures a novel bioactivity profile. Marine sponges have so far provided more than 1000 new bioactive molecules. Ethyl acetate extract of the marine sponge Dendrilla nigra on bioactivity-guided screening yielded three new compounds d...
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| Published in: | Natural product research 2014-06, Vol.28 (12), p.888-894 |
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| Main Authors: | , , , , , , , |
| Format: | Article |
| Language: | English |
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| cites | cdi_FETCH-LOGICAL-c466t-c6e54d218d96dd7fa893b8693fc7aea2c8ee0d5ec4ee84d66d6e0393a65486b93 |
| container_end_page | 894 |
| container_issue | 12 |
| container_start_page | 888 |
| container_title | Natural product research |
| container_volume | 28 |
| creator | Murali Krishna Kumar, Muthyala Devilal Naik, Jarpula Satyavathi, Kancherla Ramana, Hechhu Raghuveer Varma, Pemmadi Purna Nagasree, Kurre Smitha, Desaraju Venkata Rao, Desaraju |
| description | Chemical diversity is vital to antitubercular drug discovery as it ensures a novel bioactivity profile. Marine sponges have so far provided more than 1000 new bioactive molecules. Ethyl acetate extract of the marine sponge Dendrilla nigra on bioactivity-guided screening yielded three new compounds denigrins A-C, with potent antitubercular activity. Spectral and chemical analyses confirmed that these three compounds belong to the 3,4-diaryl pyrrole alkaloid category. The presence of monohydroxy substitution on benzene rings is not very common in lamellarin and related 3,4-diaryl pyrrole alkaloids isolated from marine invertebrates. Among these, denigrin C showed highest potency (minimum inhibitory concentration 4 μg/mL) against Mycobacterium tuberculosis H37Rv. |
| doi_str_mv | 10.1080/14786419.2014.891112 |
| format | article |
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Marine sponges have so far provided more than 1000 new bioactive molecules. Ethyl acetate extract of the marine sponge Dendrilla nigra on bioactivity-guided screening yielded three new compounds denigrins A-C, with potent antitubercular activity. Spectral and chemical analyses confirmed that these three compounds belong to the 3,4-diaryl pyrrole alkaloid category. The presence of monohydroxy substitution on benzene rings is not very common in lamellarin and related 3,4-diaryl pyrrole alkaloids isolated from marine invertebrates. Among these, denigrin C showed highest potency (minimum inhibitory concentration 4 μg/mL) against Mycobacterium tuberculosis H37Rv.</description><identifier>ISSN: 1478-6419</identifier><identifier>EISSN: 1478-6427</identifier><identifier>DOI: 10.1080/14786419.2014.891112</identifier><identifier>PMID: 24650250</identifier><language>eng</language><publisher>England: Taylor & Francis</publisher><subject>3,4-diarylpyrrole alkaloids ; Alkaloids - chemistry ; Alkaloids - isolation & purification ; Alkaloids - pharmacology ; Animals ; Anti-Bacterial Agents - pharmacology ; antitubercular ; Antitubercular Agents - chemistry ; Antitubercular Agents - isolation & purification ; Antitubercular Agents - pharmacology ; Aspergillus niger - drug effects ; Bacillus subtilis - drug effects ; Candida albicans - drug effects ; Dendrilla nigra ; Escherichia coli - drug effects ; India ; Marine Biology ; marine sponge ; Microbial Sensitivity Tests ; Mycobacterium tuberculosis ; Mycobacterium tuberculosis - drug effects ; Nuclear Magnetic Resonance, Biomolecular ; Oceans and Seas ; Porifera - chemistry ; Pseudomonas aeruginosa - drug effects ; Pyrroles - chemistry ; Pyrroles - isolation & purification ; Pyrroles - pharmacology ; Staphylococcus aureus - drug effects</subject><ispartof>Natural product research, 2014-06, Vol.28 (12), p.888-894</ispartof><rights>2014 Taylor & Francis 2014</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c466t-c6e54d218d96dd7fa893b8693fc7aea2c8ee0d5ec4ee84d66d6e0393a65486b93</citedby><cites>FETCH-LOGICAL-c466t-c6e54d218d96dd7fa893b8693fc7aea2c8ee0d5ec4ee84d66d6e0393a65486b93</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/24650250$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Murali Krishna Kumar, Muthyala</creatorcontrib><creatorcontrib>Devilal Naik, Jarpula</creatorcontrib><creatorcontrib>Satyavathi, Kancherla</creatorcontrib><creatorcontrib>Ramana, Hechhu</creatorcontrib><creatorcontrib>Raghuveer Varma, Pemmadi</creatorcontrib><creatorcontrib>Purna Nagasree, Kurre</creatorcontrib><creatorcontrib>Smitha, Desaraju</creatorcontrib><creatorcontrib>Venkata Rao, Desaraju</creatorcontrib><title>Denigrins A-C: new antitubercular 3,4-diarylpyrrole alkaloids from Dendrilla nigra</title><title>Natural product research</title><addtitle>Nat Prod Res</addtitle><description>Chemical diversity is vital to antitubercular drug discovery as it ensures a novel bioactivity profile. Marine sponges have so far provided more than 1000 new bioactive molecules. Ethyl acetate extract of the marine sponge Dendrilla nigra on bioactivity-guided screening yielded three new compounds denigrins A-C, with potent antitubercular activity. Spectral and chemical analyses confirmed that these three compounds belong to the 3,4-diaryl pyrrole alkaloid category. The presence of monohydroxy substitution on benzene rings is not very common in lamellarin and related 3,4-diaryl pyrrole alkaloids isolated from marine invertebrates. Among these, denigrin C showed highest potency (minimum inhibitory concentration 4 μg/mL) against Mycobacterium tuberculosis H37Rv.</description><subject>3,4-diarylpyrrole alkaloids</subject><subject>Alkaloids - chemistry</subject><subject>Alkaloids - isolation & purification</subject><subject>Alkaloids - pharmacology</subject><subject>Animals</subject><subject>Anti-Bacterial Agents - pharmacology</subject><subject>antitubercular</subject><subject>Antitubercular Agents - chemistry</subject><subject>Antitubercular Agents - isolation & purification</subject><subject>Antitubercular Agents - pharmacology</subject><subject>Aspergillus niger - drug effects</subject><subject>Bacillus subtilis - drug effects</subject><subject>Candida albicans - drug effects</subject><subject>Dendrilla nigra</subject><subject>Escherichia coli - drug effects</subject><subject>India</subject><subject>Marine Biology</subject><subject>marine sponge</subject><subject>Microbial Sensitivity Tests</subject><subject>Mycobacterium tuberculosis</subject><subject>Mycobacterium tuberculosis - drug effects</subject><subject>Nuclear Magnetic Resonance, Biomolecular</subject><subject>Oceans and Seas</subject><subject>Porifera - chemistry</subject><subject>Pseudomonas aeruginosa - drug effects</subject><subject>Pyrroles - chemistry</subject><subject>Pyrroles - isolation & purification</subject><subject>Pyrroles - pharmacology</subject><subject>Staphylococcus aureus - drug effects</subject><issn>1478-6419</issn><issn>1478-6427</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><recordid>eNqFkE1LAzEQhoMoVqv_QGSPHtyaZJM060VK_YSCIHoOaTIr0eymJruU_nu39OOopwnDM-9MHoQuCB4RLPENYWMpGClHFBM2kiUhhB6gk3U7F4yOD_dvUg7QaUpfGFPCOT9GA8oEx5TjE_R2D437jK5J2SSf3mYNLDPdtK7t5hBN53XMimuWW6fjyi9WMQYPmfbf2gdnU1bFUGd9hI3Oe52to_QZOqq0T3C-rUP08fjwPn3OZ69PL9PJLDdMiDY3AjizlEhbCmvHlZZlMZeiLCoz1qCpkQDYcjAMQDIrhBWAi7LQgjMp5mUxRFeb3EUMPx2kVtUuGejvaCB0SZEeFJJIhv9HOS1YL5WKHmUb1MSQUoRKLaKr-98rgtVavNqJV2vxaiO-H7vcbujmNdj90M50D9xtANdUIdZ6GaK3qtUrH2IVdWNcUsWfK34BdBCRSw</recordid><startdate>20140618</startdate><enddate>20140618</enddate><creator>Murali Krishna Kumar, Muthyala</creator><creator>Devilal Naik, Jarpula</creator><creator>Satyavathi, Kancherla</creator><creator>Ramana, Hechhu</creator><creator>Raghuveer Varma, Pemmadi</creator><creator>Purna Nagasree, Kurre</creator><creator>Smitha, Desaraju</creator><creator>Venkata Rao, Desaraju</creator><general>Taylor & Francis</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>7QO</scope><scope>7TN</scope><scope>8FD</scope><scope>F1W</scope><scope>FR3</scope><scope>H95</scope><scope>L.G</scope><scope>P64</scope></search><sort><creationdate>20140618</creationdate><title>Denigrins A-C: new antitubercular 3,4-diarylpyrrole alkaloids from Dendrilla nigra</title><author>Murali Krishna Kumar, Muthyala ; Devilal Naik, Jarpula ; Satyavathi, Kancherla ; Ramana, Hechhu ; Raghuveer Varma, Pemmadi ; Purna Nagasree, Kurre ; Smitha, Desaraju ; Venkata Rao, Desaraju</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c466t-c6e54d218d96dd7fa893b8693fc7aea2c8ee0d5ec4ee84d66d6e0393a65486b93</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><topic>3,4-diarylpyrrole alkaloids</topic><topic>Alkaloids - chemistry</topic><topic>Alkaloids - isolation & purification</topic><topic>Alkaloids - pharmacology</topic><topic>Animals</topic><topic>Anti-Bacterial Agents - pharmacology</topic><topic>antitubercular</topic><topic>Antitubercular Agents - chemistry</topic><topic>Antitubercular Agents - isolation & purification</topic><topic>Antitubercular Agents - pharmacology</topic><topic>Aspergillus niger - drug effects</topic><topic>Bacillus subtilis - drug effects</topic><topic>Candida albicans - drug effects</topic><topic>Dendrilla nigra</topic><topic>Escherichia coli - drug effects</topic><topic>India</topic><topic>Marine Biology</topic><topic>marine sponge</topic><topic>Microbial Sensitivity Tests</topic><topic>Mycobacterium tuberculosis</topic><topic>Mycobacterium tuberculosis - drug effects</topic><topic>Nuclear Magnetic Resonance, Biomolecular</topic><topic>Oceans and Seas</topic><topic>Porifera - chemistry</topic><topic>Pseudomonas aeruginosa - drug effects</topic><topic>Pyrroles - chemistry</topic><topic>Pyrroles - isolation & purification</topic><topic>Pyrroles - pharmacology</topic><topic>Staphylococcus aureus - drug effects</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Murali Krishna Kumar, Muthyala</creatorcontrib><creatorcontrib>Devilal Naik, Jarpula</creatorcontrib><creatorcontrib>Satyavathi, Kancherla</creatorcontrib><creatorcontrib>Ramana, Hechhu</creatorcontrib><creatorcontrib>Raghuveer Varma, Pemmadi</creatorcontrib><creatorcontrib>Purna Nagasree, Kurre</creatorcontrib><creatorcontrib>Smitha, Desaraju</creatorcontrib><creatorcontrib>Venkata Rao, Desaraju</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>Biotechnology Research Abstracts</collection><collection>Oceanic Abstracts</collection><collection>Technology Research Database</collection><collection>ASFA: Aquatic Sciences and Fisheries Abstracts</collection><collection>Engineering Research Database</collection><collection>Aquatic Science & Fisheries Abstracts (ASFA) 1: Biological Sciences & Living Resources</collection><collection>Aquatic Science & Fisheries Abstracts (ASFA) Professional</collection><collection>Biotechnology and BioEngineering Abstracts</collection><jtitle>Natural product research</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Murali Krishna Kumar, Muthyala</au><au>Devilal Naik, Jarpula</au><au>Satyavathi, Kancherla</au><au>Ramana, Hechhu</au><au>Raghuveer Varma, Pemmadi</au><au>Purna Nagasree, Kurre</au><au>Smitha, Desaraju</au><au>Venkata Rao, Desaraju</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Denigrins A-C: new antitubercular 3,4-diarylpyrrole alkaloids from Dendrilla nigra</atitle><jtitle>Natural product research</jtitle><addtitle>Nat Prod Res</addtitle><date>2014-06-18</date><risdate>2014</risdate><volume>28</volume><issue>12</issue><spage>888</spage><epage>894</epage><pages>888-894</pages><issn>1478-6419</issn><eissn>1478-6427</eissn><abstract>Chemical diversity is vital to antitubercular drug discovery as it ensures a novel bioactivity profile. Marine sponges have so far provided more than 1000 new bioactive molecules. Ethyl acetate extract of the marine sponge Dendrilla nigra on bioactivity-guided screening yielded three new compounds denigrins A-C, with potent antitubercular activity. Spectral and chemical analyses confirmed that these three compounds belong to the 3,4-diaryl pyrrole alkaloid category. The presence of monohydroxy substitution on benzene rings is not very common in lamellarin and related 3,4-diaryl pyrrole alkaloids isolated from marine invertebrates. Among these, denigrin C showed highest potency (minimum inhibitory concentration 4 μg/mL) against Mycobacterium tuberculosis H37Rv.</abstract><cop>England</cop><pub>Taylor & Francis</pub><pmid>24650250</pmid><doi>10.1080/14786419.2014.891112</doi><tpages>7</tpages></addata></record> |
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| identifier | ISSN: 1478-6419 |
| ispartof | Natural product research, 2014-06, Vol.28 (12), p.888-894 |
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| language | eng |
| recordid | cdi_crossref_primary_10_1080_14786419_2014_891112 |
| source | Taylor and Francis Science and Technology Collection |
| subjects | 3,4-diarylpyrrole alkaloids Alkaloids - chemistry Alkaloids - isolation & purification Alkaloids - pharmacology Animals Anti-Bacterial Agents - pharmacology antitubercular Antitubercular Agents - chemistry Antitubercular Agents - isolation & purification Antitubercular Agents - pharmacology Aspergillus niger - drug effects Bacillus subtilis - drug effects Candida albicans - drug effects Dendrilla nigra Escherichia coli - drug effects India Marine Biology marine sponge Microbial Sensitivity Tests Mycobacterium tuberculosis Mycobacterium tuberculosis - drug effects Nuclear Magnetic Resonance, Biomolecular Oceans and Seas Porifera - chemistry Pseudomonas aeruginosa - drug effects Pyrroles - chemistry Pyrroles - isolation & purification Pyrroles - pharmacology Staphylococcus aureus - drug effects |
| title | Denigrins A-C: new antitubercular 3,4-diarylpyrrole alkaloids from Dendrilla nigra |
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