Antimycobacterial brominated metabolites from two species of marine sponges
Abstract A screening of 500 crude extracts of marine invertebrates against the growth of MYCOBACTERIUM TUBERCULOSIS H37Rv yielded MeOH extracts of the sponges APLYSINA CAULIFORMIS and PACHYCHALINA sp. with significant activity. Further bioassay-guided fractionation of both crude extracts led to the...
Gespeichert in:
| Veröffentlicht in: | Planta medica 2006-04, Vol.72 (5), p.437-441 |
|---|---|
| Hauptverfasser: | , , , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 441 |
|---|---|
| container_issue | 5 |
| container_start_page | 437 |
| container_title | Planta medica |
| container_volume | 72 |
| creator | Oliveira, M.F. de Oliveira, J.H.H.L. de Galetti, F.C.S Souza, A.O. de Silva, C.L Hajdu, E Peixinho, S Berlinck, R.G.S |
| description | Abstract
A screening of 500 crude extracts of marine invertebrates against the growth of MYCOBACTERIUM TUBERCULOSIS H37Rv yielded MeOH extracts of the sponges APLYSINA CAULIFORMIS and PACHYCHALINA sp. with significant activity. Further bioassay-guided fractionation of both crude extracts led to the isolation of four bromine-containing metabolites. The known (+)-fistularin-3 (1) and 11-deoxyfistularin-3 (2), and the new compound 2-(3-amino-2,4-dibromo-6-hydroxyphenyl)acetic acid (3) were isolated from the sponge A. CAULIFORMIS, while the new bromotyrosine-derived 3-(3,5-dibromo-4-methoxyphenyl)-2-methoxy-N-methylpropan-1-ammonium (4) was isolated from PACHYCHALINA sp. Compound 4 exhibited weak antimycobacterial activity while compounds 1 - 3 displayed activity against MYCOBACTERIUM TUBERCULOSIS H37Rv, with MICs of 7.1, 7.3 and 49 μM, respectively. Compounds 1 and 2 also exhibited low cytotoxicity against J744 macrophages, indicating that both 1 and 2 are interesting leads for the development of new anti-tuberculosis agents. |
| doi_str_mv | 10.1055/s-2005-916239 |
| format | Article |
| fullrecord | <record><control><sourceid>pubmed_pasca</sourceid><recordid>TN_cdi_pubmed_primary_16557458</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>16557458</sourcerecordid><originalsourceid>FETCH-LOGICAL-c383t-1bd608cf40888c2c70e1a4ada8628311f657542fae571deaee0be6d617c016c3</originalsourceid><addsrcrecordid>eNpFkElLxEAQhRtRdFyOXjUXb0arekvnOIgbCh4cz02nU9GWLEM6g_jv7SGKp4KPj8erx9gpwhWCUtcx5wAqL1FzUe6wBUpR5sA57rIFgOA5lFIcsMMYPwFQlgD77AC1UoVUZsGelv0Uum8_VM5PNAbXZtU4dKF3E9VZR5OrhjZMFLMm4Wz6GrK4Jh8SGJqsc2PoKZGhf6d4zPYa10Y6-b1HbHV3u7p5yJ9f7h9vls-5F0ZMOVa1BuMbCcYYz30BhE662hnNjUBstCqU5I0jVWBNjggq0rXGwgNqL47Y2Ry73lQd1XY9htTj2_49lYSLX8FF79pmdL0P8d8rtNaSy-Rdzt70Eagj-zlsxj4Vtwh2u62NdrutnbdN-vmsN26w7n1MkW-vHFAAgtGgQPwAMFdyyg</addsrcrecordid><sourcetype>Index Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype></control><display><type>article</type><title>Antimycobacterial brominated metabolites from two species of marine sponges</title><source>MEDLINE</source><source>Thieme Connect Journals</source><creator>Oliveira, M.F. de ; Oliveira, J.H.H.L. de ; Galetti, F.C.S ; Souza, A.O. de ; Silva, C.L ; Hajdu, E ; Peixinho, S ; Berlinck, R.G.S</creator><creatorcontrib>Oliveira, M.F. de ; Oliveira, J.H.H.L. de ; Galetti, F.C.S ; Souza, A.O. de ; Silva, C.L ; Hajdu, E ; Peixinho, S ; Berlinck, R.G.S</creatorcontrib><description>Abstract
A screening of 500 crude extracts of marine invertebrates against the growth of MYCOBACTERIUM TUBERCULOSIS H37Rv yielded MeOH extracts of the sponges APLYSINA CAULIFORMIS and PACHYCHALINA sp. with significant activity. Further bioassay-guided fractionation of both crude extracts led to the isolation of four bromine-containing metabolites. The known (+)-fistularin-3 (1) and 11-deoxyfistularin-3 (2), and the new compound 2-(3-amino-2,4-dibromo-6-hydroxyphenyl)acetic acid (3) were isolated from the sponge A. CAULIFORMIS, while the new bromotyrosine-derived 3-(3,5-dibromo-4-methoxyphenyl)-2-methoxy-N-methylpropan-1-ammonium (4) was isolated from PACHYCHALINA sp. Compound 4 exhibited weak antimycobacterial activity while compounds 1 - 3 displayed activity against MYCOBACTERIUM TUBERCULOSIS H37Rv, with MICs of 7.1, 7.3 and 49 μM, respectively. Compounds 1 and 2 also exhibited low cytotoxicity against J744 macrophages, indicating that both 1 and 2 are interesting leads for the development of new anti-tuberculosis agents.</description><identifier>ISSN: 0032-0943</identifier><identifier>EISSN: 1439-0221</identifier><identifier>DOI: 10.1055/s-2005-916239</identifier><identifier>PMID: 16557458</identifier><identifier>CODEN: PLMEAA</identifier><language>eng</language><publisher>Stuttgart: Thieme</publisher><subject>animal pathogenic bacteria ; Animals ; Anti-Bacterial Agents - administration & dosage ; Anti-Bacterial Agents - pharmacology ; Anti-Bacterial Agents - therapeutic use ; antibacterial properties ; Aplysina cauliformis ; azoles ; Biological and medical sciences ; deoxyfistularin ; fistularin ; General pharmacology ; human health ; Humans ; Inhibitory Concentration 50 ; Macrophages - drug effects ; Medical sciences ; Microbial Sensitivity Tests ; Mycobacterium tuberculosis ; Mycobacterium tuberculosis - drug effects ; Original Paper ; Pachychalina ; Pharmacognosy. Homeopathy. Health food ; Pharmacology. Drug treatments ; phenylacetic acid ; Phytotherapy ; Porifera ; Porifera - metabolism</subject><ispartof>Planta medica, 2006-04, Vol.72 (5), p.437-441</ispartof><rights>Georg Thieme Verlag KG Stuttgart · New York</rights><rights>2006 INIST-CNRS</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c383t-1bd608cf40888c2c70e1a4ada8628311f657542fae571deaee0be6d617c016c3</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-2005-916239.pdf$$EPDF$$P50$$Gthieme$$H</linktopdf><linktohtml>$$Uhttps://www.thieme-connect.de/products/ejournals/html/10.1055/s-2005-916239$$EHTML$$P50$$Gthieme$$H</linktohtml><link.rule.ids>314,777,781,3005,27905,27906,54540,54541</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=17666424$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/16557458$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Oliveira, M.F. de</creatorcontrib><creatorcontrib>Oliveira, J.H.H.L. de</creatorcontrib><creatorcontrib>Galetti, F.C.S</creatorcontrib><creatorcontrib>Souza, A.O. de</creatorcontrib><creatorcontrib>Silva, C.L</creatorcontrib><creatorcontrib>Hajdu, E</creatorcontrib><creatorcontrib>Peixinho, S</creatorcontrib><creatorcontrib>Berlinck, R.G.S</creatorcontrib><title>Antimycobacterial brominated metabolites from two species of marine sponges</title><title>Planta medica</title><addtitle>Planta Med</addtitle><description>Abstract
A screening of 500 crude extracts of marine invertebrates against the growth of MYCOBACTERIUM TUBERCULOSIS H37Rv yielded MeOH extracts of the sponges APLYSINA CAULIFORMIS and PACHYCHALINA sp. with significant activity. Further bioassay-guided fractionation of both crude extracts led to the isolation of four bromine-containing metabolites. The known (+)-fistularin-3 (1) and 11-deoxyfistularin-3 (2), and the new compound 2-(3-amino-2,4-dibromo-6-hydroxyphenyl)acetic acid (3) were isolated from the sponge A. CAULIFORMIS, while the new bromotyrosine-derived 3-(3,5-dibromo-4-methoxyphenyl)-2-methoxy-N-methylpropan-1-ammonium (4) was isolated from PACHYCHALINA sp. Compound 4 exhibited weak antimycobacterial activity while compounds 1 - 3 displayed activity against MYCOBACTERIUM TUBERCULOSIS H37Rv, with MICs of 7.1, 7.3 and 49 μM, respectively. Compounds 1 and 2 also exhibited low cytotoxicity against J744 macrophages, indicating that both 1 and 2 are interesting leads for the development of new anti-tuberculosis agents.</description><subject>animal pathogenic bacteria</subject><subject>Animals</subject><subject>Anti-Bacterial Agents - administration & dosage</subject><subject>Anti-Bacterial Agents - pharmacology</subject><subject>Anti-Bacterial Agents - therapeutic use</subject><subject>antibacterial properties</subject><subject>Aplysina cauliformis</subject><subject>azoles</subject><subject>Biological and medical sciences</subject><subject>deoxyfistularin</subject><subject>fistularin</subject><subject>General pharmacology</subject><subject>human health</subject><subject>Humans</subject><subject>Inhibitory Concentration 50</subject><subject>Macrophages - drug effects</subject><subject>Medical sciences</subject><subject>Microbial Sensitivity Tests</subject><subject>Mycobacterium tuberculosis</subject><subject>Mycobacterium tuberculosis - drug effects</subject><subject>Original Paper</subject><subject>Pachychalina</subject><subject>Pharmacognosy. Homeopathy. Health food</subject><subject>Pharmacology. Drug treatments</subject><subject>phenylacetic acid</subject><subject>Phytotherapy</subject><subject>Porifera</subject><subject>Porifera - metabolism</subject><issn>0032-0943</issn><issn>1439-0221</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2006</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpFkElLxEAQhRtRdFyOXjUXb0arekvnOIgbCh4cz02nU9GWLEM6g_jv7SGKp4KPj8erx9gpwhWCUtcx5wAqL1FzUe6wBUpR5sA57rIFgOA5lFIcsMMYPwFQlgD77AC1UoVUZsGelv0Uum8_VM5PNAbXZtU4dKF3E9VZR5OrhjZMFLMm4Wz6GrK4Jh8SGJqsc2PoKZGhf6d4zPYa10Y6-b1HbHV3u7p5yJ9f7h9vls-5F0ZMOVa1BuMbCcYYz30BhE662hnNjUBstCqU5I0jVWBNjggq0rXGwgNqL47Y2Ry73lQd1XY9htTj2_49lYSLX8FF79pmdL0P8d8rtNaSy-Rdzt70Eagj-zlsxj4Vtwh2u62NdrutnbdN-vmsN26w7n1MkW-vHFAAgtGgQPwAMFdyyg</recordid><startdate>20060401</startdate><enddate>20060401</enddate><creator>Oliveira, M.F. de</creator><creator>Oliveira, J.H.H.L. de</creator><creator>Galetti, F.C.S</creator><creator>Souza, A.O. de</creator><creator>Silva, C.L</creator><creator>Hajdu, E</creator><creator>Peixinho, S</creator><creator>Berlinck, R.G.S</creator><general>Thieme</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></search><sort><creationdate>20060401</creationdate><title>Antimycobacterial brominated metabolites from two species of marine sponges</title><author>Oliveira, M.F. de ; Oliveira, J.H.H.L. de ; Galetti, F.C.S ; Souza, A.O. de ; Silva, C.L ; Hajdu, E ; Peixinho, S ; Berlinck, R.G.S</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c383t-1bd608cf40888c2c70e1a4ada8628311f657542fae571deaee0be6d617c016c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2006</creationdate><topic>animal pathogenic bacteria</topic><topic>Animals</topic><topic>Anti-Bacterial Agents - administration & dosage</topic><topic>Anti-Bacterial Agents - pharmacology</topic><topic>Anti-Bacterial Agents - therapeutic use</topic><topic>antibacterial properties</topic><topic>Aplysina cauliformis</topic><topic>azoles</topic><topic>Biological and medical sciences</topic><topic>deoxyfistularin</topic><topic>fistularin</topic><topic>General pharmacology</topic><topic>human health</topic><topic>Humans</topic><topic>Inhibitory Concentration 50</topic><topic>Macrophages - drug effects</topic><topic>Medical sciences</topic><topic>Microbial Sensitivity Tests</topic><topic>Mycobacterium tuberculosis</topic><topic>Mycobacterium tuberculosis - drug effects</topic><topic>Original Paper</topic><topic>Pachychalina</topic><topic>Pharmacognosy. Homeopathy. Health food</topic><topic>Pharmacology. Drug treatments</topic><topic>phenylacetic acid</topic><topic>Phytotherapy</topic><topic>Porifera</topic><topic>Porifera - metabolism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Oliveira, M.F. de</creatorcontrib><creatorcontrib>Oliveira, J.H.H.L. de</creatorcontrib><creatorcontrib>Galetti, F.C.S</creatorcontrib><creatorcontrib>Souza, A.O. de</creatorcontrib><creatorcontrib>Silva, C.L</creatorcontrib><creatorcontrib>Hajdu, E</creatorcontrib><creatorcontrib>Peixinho, S</creatorcontrib><creatorcontrib>Berlinck, R.G.S</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><jtitle>Planta medica</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Oliveira, M.F. de</au><au>Oliveira, J.H.H.L. de</au><au>Galetti, F.C.S</au><au>Souza, A.O. de</au><au>Silva, C.L</au><au>Hajdu, E</au><au>Peixinho, S</au><au>Berlinck, R.G.S</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Antimycobacterial brominated metabolites from two species of marine sponges</atitle><jtitle>Planta medica</jtitle><addtitle>Planta Med</addtitle><date>2006-04-01</date><risdate>2006</risdate><volume>72</volume><issue>5</issue><spage>437</spage><epage>441</epage><pages>437-441</pages><issn>0032-0943</issn><eissn>1439-0221</eissn><coden>PLMEAA</coden><abstract>Abstract
A screening of 500 crude extracts of marine invertebrates against the growth of MYCOBACTERIUM TUBERCULOSIS H37Rv yielded MeOH extracts of the sponges APLYSINA CAULIFORMIS and PACHYCHALINA sp. with significant activity. Further bioassay-guided fractionation of both crude extracts led to the isolation of four bromine-containing metabolites. The known (+)-fistularin-3 (1) and 11-deoxyfistularin-3 (2), and the new compound 2-(3-amino-2,4-dibromo-6-hydroxyphenyl)acetic acid (3) were isolated from the sponge A. CAULIFORMIS, while the new bromotyrosine-derived 3-(3,5-dibromo-4-methoxyphenyl)-2-methoxy-N-methylpropan-1-ammonium (4) was isolated from PACHYCHALINA sp. Compound 4 exhibited weak antimycobacterial activity while compounds 1 - 3 displayed activity against MYCOBACTERIUM TUBERCULOSIS H37Rv, with MICs of 7.1, 7.3 and 49 μM, respectively. Compounds 1 and 2 also exhibited low cytotoxicity against J744 macrophages, indicating that both 1 and 2 are interesting leads for the development of new anti-tuberculosis agents.</abstract><cop>Stuttgart</cop><cop>New York, NY</cop><pub>Thieme</pub><pmid>16557458</pmid><doi>10.1055/s-2005-916239</doi><tpages>5</tpages><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0032-0943 |
| ispartof | Planta medica, 2006-04, Vol.72 (5), p.437-441 |
| issn | 0032-0943 1439-0221 |
| language | eng |
| recordid | cdi_pubmed_primary_16557458 |
| source | MEDLINE; Thieme Connect Journals |
| subjects | animal pathogenic bacteria Animals Anti-Bacterial Agents - administration & dosage Anti-Bacterial Agents - pharmacology Anti-Bacterial Agents - therapeutic use antibacterial properties Aplysina cauliformis azoles Biological and medical sciences deoxyfistularin fistularin General pharmacology human health Humans Inhibitory Concentration 50 Macrophages - drug effects Medical sciences Microbial Sensitivity Tests Mycobacterium tuberculosis Mycobacterium tuberculosis - drug effects Original Paper Pachychalina Pharmacognosy. Homeopathy. Health food Pharmacology. Drug treatments phenylacetic acid Phytotherapy Porifera Porifera - metabolism |
| title | Antimycobacterial brominated metabolites from two species of marine sponges |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-18T05%3A38%3A17IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-pubmed_pasca&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Antimycobacterial%20brominated%20metabolites%20from%20two%20species%20of%20marine%20sponges&rft.jtitle=Planta%20medica&rft.au=Oliveira,%20M.F.%20de&rft.date=2006-04-01&rft.volume=72&rft.issue=5&rft.spage=437&rft.epage=441&rft.pages=437-441&rft.issn=0032-0943&rft.eissn=1439-0221&rft.coden=PLMEAA&rft_id=info:doi/10.1055/s-2005-916239&rft_dat=%3Cpubmed_pasca%3E16557458%3C/pubmed_pasca%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_id=info:pmid/16557458&rfr_iscdi=true |