Antibacterial modified diketopiperazines from two ascidians of the genus Didemnum
Autor(a) principal: | |
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Data de Publicação: | 2009 |
Outros Autores: | , , , , , , , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Journal of the Brazilian Chemical Society (Online) |
Texto Completo: | http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532009000400014 |
Resumo: | The chemical investigation of the crude extract of an ascidian of the genus Didemnumled to the isolation of the modified diketopiperazine rodriguesines A (1) and (2) as a mixture of homologues, which could be identified by analysis of spectroscopic data including MS/MS experiments. The investigation of a second Didemnumsp. led to the isolation of N-acetyl-rodriguesine A (3) and N-acetyl-rodriguesine B (4). The absolute configuration of compounds 1and 2could be established by hydrolysis and Marfey's analysis and comparison with literature data reported for compound 3, previously obtained as a synthetic product. The mixture of 1and 2displayed moderate antibiotic activity against a clinical isolate of Streptococcus mutansand against S. mutansUA159 and Staphylococcus aureusATCC6538. |
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Antibacterial modified diketopiperazines from two ascidians of the genus Didemnumascidianmarinediketopiperazineabsolute configurationantibioticThe chemical investigation of the crude extract of an ascidian of the genus Didemnumled to the isolation of the modified diketopiperazine rodriguesines A (1) and (2) as a mixture of homologues, which could be identified by analysis of spectroscopic data including MS/MS experiments. The investigation of a second Didemnumsp. led to the isolation of N-acetyl-rodriguesine A (3) and N-acetyl-rodriguesine B (4). The absolute configuration of compounds 1and 2could be established by hydrolysis and Marfey's analysis and comparison with literature data reported for compound 3, previously obtained as a synthetic product. The mixture of 1and 2displayed moderate antibiotic activity against a clinical isolate of Streptococcus mutansand against S. mutansUA159 and Staphylococcus aureusATCC6538.Sociedade Brasileira de Química2009-01-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532009000400014Journal of the Brazilian Chemical Society v.20 n.4 2009reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.1590/S0103-50532009000400014info:eu-repo/semantics/openAccessKossuga,Miriam H.Lira,Simone P.McHugh,ShaynaTorres,Yohandra R.Lima,Bruna A.Gonçalves,ReginaldoVeloso,KatyuscyaFerreira,Antonio G.Rocha,Rosana M.Berlinck,Roberto G. S.eng2009-06-10T00:00:00Zoai:scielo:S0103-50532009000400014Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2009-06-10T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false |
dc.title.none.fl_str_mv |
Antibacterial modified diketopiperazines from two ascidians of the genus Didemnum |
title |
Antibacterial modified diketopiperazines from two ascidians of the genus Didemnum |
spellingShingle |
Antibacterial modified diketopiperazines from two ascidians of the genus Didemnum Kossuga,Miriam H. ascidian marine diketopiperazine absolute configuration antibiotic |
title_short |
Antibacterial modified diketopiperazines from two ascidians of the genus Didemnum |
title_full |
Antibacterial modified diketopiperazines from two ascidians of the genus Didemnum |
title_fullStr |
Antibacterial modified diketopiperazines from two ascidians of the genus Didemnum |
title_full_unstemmed |
Antibacterial modified diketopiperazines from two ascidians of the genus Didemnum |
title_sort |
Antibacterial modified diketopiperazines from two ascidians of the genus Didemnum |
author |
Kossuga,Miriam H. |
author_facet |
Kossuga,Miriam H. Lira,Simone P. McHugh,Shayna Torres,Yohandra R. Lima,Bruna A. Gonçalves,Reginaldo Veloso,Katyuscya Ferreira,Antonio G. Rocha,Rosana M. Berlinck,Roberto G. S. |
author_role |
author |
author2 |
Lira,Simone P. McHugh,Shayna Torres,Yohandra R. Lima,Bruna A. Gonçalves,Reginaldo Veloso,Katyuscya Ferreira,Antonio G. Rocha,Rosana M. Berlinck,Roberto G. S. |
author2_role |
author author author author author author author author author |
dc.contributor.author.fl_str_mv |
Kossuga,Miriam H. Lira,Simone P. McHugh,Shayna Torres,Yohandra R. Lima,Bruna A. Gonçalves,Reginaldo Veloso,Katyuscya Ferreira,Antonio G. Rocha,Rosana M. Berlinck,Roberto G. S. |
dc.subject.por.fl_str_mv |
ascidian marine diketopiperazine absolute configuration antibiotic |
topic |
ascidian marine diketopiperazine absolute configuration antibiotic |
description |
The chemical investigation of the crude extract of an ascidian of the genus Didemnumled to the isolation of the modified diketopiperazine rodriguesines A (1) and (2) as a mixture of homologues, which could be identified by analysis of spectroscopic data including MS/MS experiments. The investigation of a second Didemnumsp. led to the isolation of N-acetyl-rodriguesine A (3) and N-acetyl-rodriguesine B (4). The absolute configuration of compounds 1and 2could be established by hydrolysis and Marfey's analysis and comparison with literature data reported for compound 3, previously obtained as a synthetic product. The mixture of 1and 2displayed moderate antibiotic activity against a clinical isolate of Streptococcus mutansand against S. mutansUA159 and Staphylococcus aureusATCC6538. |
publishDate |
2009 |
dc.date.none.fl_str_mv |
2009-01-01 |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/article |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
format |
article |
status_str |
publishedVersion |
dc.identifier.uri.fl_str_mv |
http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532009000400014 |
url |
http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532009000400014 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
10.1590/S0103-50532009000400014 |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
dc.format.none.fl_str_mv |
text/html |
dc.publisher.none.fl_str_mv |
Sociedade Brasileira de Química |
publisher.none.fl_str_mv |
Sociedade Brasileira de Química |
dc.source.none.fl_str_mv |
Journal of the Brazilian Chemical Society v.20 n.4 2009 reponame:Journal of the Brazilian Chemical Society (Online) instname:Sociedade Brasileira de Química (SBQ) instacron:SBQ |
instname_str |
Sociedade Brasileira de Química (SBQ) |
instacron_str |
SBQ |
institution |
SBQ |
reponame_str |
Journal of the Brazilian Chemical Society (Online) |
collection |
Journal of the Brazilian Chemical Society (Online) |
repository.name.fl_str_mv |
Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ) |
repository.mail.fl_str_mv |
||office@jbcs.sbq.org.br |
_version_ |
1750318169823641600 |