Antiparasitic bromotyrosine derivatives from the Caribbean marine sponge Aiolochroia crassa
Autor(a) principal: | |
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Data de Publicação: | 2012 |
Outros Autores: | , , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Química Nova (Online) |
Texto Completo: | http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0100-40422012000600023 |
Resumo: | Six bromotyrosine-derived compounds were isolated from the Caribbean marine sponge Aiolochroia crassa: 3-bromo-5-hydroxy-O-methyltyrosine (1), 3-bromo-N,N,N-trimethyltyrosinium (2), 3-bromo-N,N,N,O-tetramethyltyrosinium (3), 3,5-dibromo-N,N,N-trimethyltyrosinium (4), 3,5-dibromo-N,N,N,O-tetramethyltyrosinium (5), and aeroplysinin-1 (6). Structural determination was performed using NMR, MS and comparison with literature data. All isolated compounds were screened for their in vitro activity against Leishmania panamensis, Plasmodium falciparum and Trypanosoma cruzi. Compound 4 showed selective antiparasitic activity against Leishmania and Plasmodium parasites. This is the first report of compounds 1, 4 and 5 in the sponge A. crassa and the first biological activity reports for compounds 2-4. This work shows that bromotyrosines are potential antiparasitic agents. |
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Antiparasitic bromotyrosine derivatives from the Caribbean marine sponge Aiolochroia crassabromotyrosinesAiolochroia crassaantiparasitic activitySix bromotyrosine-derived compounds were isolated from the Caribbean marine sponge Aiolochroia crassa: 3-bromo-5-hydroxy-O-methyltyrosine (1), 3-bromo-N,N,N-trimethyltyrosinium (2), 3-bromo-N,N,N,O-tetramethyltyrosinium (3), 3,5-dibromo-N,N,N-trimethyltyrosinium (4), 3,5-dibromo-N,N,N,O-tetramethyltyrosinium (5), and aeroplysinin-1 (6). Structural determination was performed using NMR, MS and comparison with literature data. All isolated compounds were screened for their in vitro activity against Leishmania panamensis, Plasmodium falciparum and Trypanosoma cruzi. Compound 4 showed selective antiparasitic activity against Leishmania and Plasmodium parasites. This is the first report of compounds 1, 4 and 5 in the sponge A. crassa and the first biological activity reports for compounds 2-4. This work shows that bromotyrosines are potential antiparasitic agents.Sociedade Brasileira de Química2012-01-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0100-40422012000600023Química Nova v.35 n.6 2012reponame:Química Nova (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.1590/S0100-40422012000600023info:eu-repo/semantics/openAccessGaleano,ElkinMartínez,AlejandroThomas,Olivier P.Robledo,SaraMunoz,Dianaeng2012-07-25T00:00:00Zoai:scielo:S0100-40422012000600023Revistahttps://www.scielo.br/j/qn/ONGhttps://old.scielo.br/oai/scielo-oai.phpquimicanova@sbq.org.br1678-70640100-4042opendoar:2012-07-25T00:00Química Nova (Online) - Sociedade Brasileira de Química (SBQ)false |
dc.title.none.fl_str_mv |
Antiparasitic bromotyrosine derivatives from the Caribbean marine sponge Aiolochroia crassa |
title |
Antiparasitic bromotyrosine derivatives from the Caribbean marine sponge Aiolochroia crassa |
spellingShingle |
Antiparasitic bromotyrosine derivatives from the Caribbean marine sponge Aiolochroia crassa Galeano,Elkin bromotyrosines Aiolochroia crassa antiparasitic activity |
title_short |
Antiparasitic bromotyrosine derivatives from the Caribbean marine sponge Aiolochroia crassa |
title_full |
Antiparasitic bromotyrosine derivatives from the Caribbean marine sponge Aiolochroia crassa |
title_fullStr |
Antiparasitic bromotyrosine derivatives from the Caribbean marine sponge Aiolochroia crassa |
title_full_unstemmed |
Antiparasitic bromotyrosine derivatives from the Caribbean marine sponge Aiolochroia crassa |
title_sort |
Antiparasitic bromotyrosine derivatives from the Caribbean marine sponge Aiolochroia crassa |
author |
Galeano,Elkin |
author_facet |
Galeano,Elkin Martínez,Alejandro Thomas,Olivier P. Robledo,Sara Munoz,Diana |
author_role |
author |
author2 |
Martínez,Alejandro Thomas,Olivier P. Robledo,Sara Munoz,Diana |
author2_role |
author author author author |
dc.contributor.author.fl_str_mv |
Galeano,Elkin Martínez,Alejandro Thomas,Olivier P. Robledo,Sara Munoz,Diana |
dc.subject.por.fl_str_mv |
bromotyrosines Aiolochroia crassa antiparasitic activity |
topic |
bromotyrosines Aiolochroia crassa antiparasitic activity |
description |
Six bromotyrosine-derived compounds were isolated from the Caribbean marine sponge Aiolochroia crassa: 3-bromo-5-hydroxy-O-methyltyrosine (1), 3-bromo-N,N,N-trimethyltyrosinium (2), 3-bromo-N,N,N,O-tetramethyltyrosinium (3), 3,5-dibromo-N,N,N-trimethyltyrosinium (4), 3,5-dibromo-N,N,N,O-tetramethyltyrosinium (5), and aeroplysinin-1 (6). Structural determination was performed using NMR, MS and comparison with literature data. All isolated compounds were screened for their in vitro activity against Leishmania panamensis, Plasmodium falciparum and Trypanosoma cruzi. Compound 4 showed selective antiparasitic activity against Leishmania and Plasmodium parasites. This is the first report of compounds 1, 4 and 5 in the sponge A. crassa and the first biological activity reports for compounds 2-4. This work shows that bromotyrosines are potential antiparasitic agents. |
publishDate |
2012 |
dc.date.none.fl_str_mv |
2012-01-01 |
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=S0100-40422012000600023 |
url |
http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0100-40422012000600023 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
10.1590/S0100-40422012000600023 |
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 |
Química Nova v.35 n.6 2012 reponame:Química Nova (Online) instname:Sociedade Brasileira de Química (SBQ) instacron:SBQ |
instname_str |
Sociedade Brasileira de Química (SBQ) |
instacron_str |
SBQ |
institution |
SBQ |
reponame_str |
Química Nova (Online) |
collection |
Química Nova (Online) |
repository.name.fl_str_mv |
Química Nova (Online) - Sociedade Brasileira de Química (SBQ) |
repository.mail.fl_str_mv |
quimicanova@sbq.org.br |
_version_ |
1750318113559150592 |