Xymarginatin: a new acetogenin inhibitor of mitochondrial electron transport from Xylopia emarginata Mart., Annonaceae
Autor(a) principal: | |
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Data de Publicação: | 2009 |
Outros Autores: | , , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Revista Brasileira de Farmacognosia (Online) |
Texto Completo: | http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0102-695X2009000600013 |
Resumo: | A new Annonaceous acetogenin, xymarginatin (1), was isolated from the twigs of Xyliopia emarginata Mart. (Annonaceae) by bioactivity-directed fractionation using lethality to brine shrimp. The compound 1 represents a linear C-35 Annonaceous acetogenin, lacking either tetrahydrofuran (THF) or epoxide rings, bearing a keto group at C-10, and possessing two cis-double bonds separated by two methylenes units. The structure of 1 was elucidated by ¹H and 13C-NMR, COSY, HMBC, HMQC and HRMS. The ability to inhibit the mitochondrial respiratory chain of Xymarginatin (1) was tested in a rat liver mitochondrial oxygen uptake assay, with IC50 value of 1720 nM; Rotenone as a positive control gave IC50 34.8 nM. The toxicity of compound 1 against Artemia salina Leach gave LC50 of 127 μg/mL. |
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Xymarginatin: a new acetogenin inhibitor of mitochondrial electron transport from Xylopia emarginata Mart., AnnonaceaeXylopia emarginataAnnocaceaeacetogeninelectron transportA new Annonaceous acetogenin, xymarginatin (1), was isolated from the twigs of Xyliopia emarginata Mart. (Annonaceae) by bioactivity-directed fractionation using lethality to brine shrimp. The compound 1 represents a linear C-35 Annonaceous acetogenin, lacking either tetrahydrofuran (THF) or epoxide rings, bearing a keto group at C-10, and possessing two cis-double bonds separated by two methylenes units. The structure of 1 was elucidated by ¹H and 13C-NMR, COSY, HMBC, HMQC and HRMS. The ability to inhibit the mitochondrial respiratory chain of Xymarginatin (1) was tested in a rat liver mitochondrial oxygen uptake assay, with IC50 value of 1720 nM; Rotenone as a positive control gave IC50 34.8 nM. The toxicity of compound 1 against Artemia salina Leach gave LC50 of 127 μg/mL.Sociedade Brasileira de Farmacognosia2009-12-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0102-695X2009000600013Revista Brasileira de Farmacognosia v.19 n.4 2009reponame:Revista Brasileira de Farmacognosia (Online)instname:Sociedade Brasileira de Farmacognosia (SBFgnosia)instacron:SBFGNOSIA10.1590/S0102-695X2009000600013info:eu-repo/semantics/openAccessColman-Saizarbitoria,TrinaMontilla,LindaRodriguez,MariaCastillo,AníbalHasegawa,Masahisaeng2010-05-19T00:00:00Zoai:scielo:S0102-695X2009000600013Revistahttp://www.sbfgnosia.org.br/revista/https://old.scielo.br/oai/scielo-oai.phprbgnosia@ltf.ufpb.br1981-528X0102-695Xopendoar:2010-05-19T00:00Revista Brasileira de Farmacognosia (Online) - Sociedade Brasileira de Farmacognosia (SBFgnosia)false |
dc.title.none.fl_str_mv |
Xymarginatin: a new acetogenin inhibitor of mitochondrial electron transport from Xylopia emarginata Mart., Annonaceae |
title |
Xymarginatin: a new acetogenin inhibitor of mitochondrial electron transport from Xylopia emarginata Mart., Annonaceae |
spellingShingle |
Xymarginatin: a new acetogenin inhibitor of mitochondrial electron transport from Xylopia emarginata Mart., Annonaceae Colman-Saizarbitoria,Trina Xylopia emarginata Annocaceae acetogenin electron transport |
title_short |
Xymarginatin: a new acetogenin inhibitor of mitochondrial electron transport from Xylopia emarginata Mart., Annonaceae |
title_full |
Xymarginatin: a new acetogenin inhibitor of mitochondrial electron transport from Xylopia emarginata Mart., Annonaceae |
title_fullStr |
Xymarginatin: a new acetogenin inhibitor of mitochondrial electron transport from Xylopia emarginata Mart., Annonaceae |
title_full_unstemmed |
Xymarginatin: a new acetogenin inhibitor of mitochondrial electron transport from Xylopia emarginata Mart., Annonaceae |
title_sort |
Xymarginatin: a new acetogenin inhibitor of mitochondrial electron transport from Xylopia emarginata Mart., Annonaceae |
author |
Colman-Saizarbitoria,Trina |
author_facet |
Colman-Saizarbitoria,Trina Montilla,Linda Rodriguez,Maria Castillo,Aníbal Hasegawa,Masahisa |
author_role |
author |
author2 |
Montilla,Linda Rodriguez,Maria Castillo,Aníbal Hasegawa,Masahisa |
author2_role |
author author author author |
dc.contributor.author.fl_str_mv |
Colman-Saizarbitoria,Trina Montilla,Linda Rodriguez,Maria Castillo,Aníbal Hasegawa,Masahisa |
dc.subject.por.fl_str_mv |
Xylopia emarginata Annocaceae acetogenin electron transport |
topic |
Xylopia emarginata Annocaceae acetogenin electron transport |
description |
A new Annonaceous acetogenin, xymarginatin (1), was isolated from the twigs of Xyliopia emarginata Mart. (Annonaceae) by bioactivity-directed fractionation using lethality to brine shrimp. The compound 1 represents a linear C-35 Annonaceous acetogenin, lacking either tetrahydrofuran (THF) or epoxide rings, bearing a keto group at C-10, and possessing two cis-double bonds separated by two methylenes units. The structure of 1 was elucidated by ¹H and 13C-NMR, COSY, HMBC, HMQC and HRMS. The ability to inhibit the mitochondrial respiratory chain of Xymarginatin (1) was tested in a rat liver mitochondrial oxygen uptake assay, with IC50 value of 1720 nM; Rotenone as a positive control gave IC50 34.8 nM. The toxicity of compound 1 against Artemia salina Leach gave LC50 of 127 μg/mL. |
publishDate |
2009 |
dc.date.none.fl_str_mv |
2009-12-01 |
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=S0102-695X2009000600013 |
url |
http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0102-695X2009000600013 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
10.1590/S0102-695X2009000600013 |
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 Farmacognosia |
publisher.none.fl_str_mv |
Sociedade Brasileira de Farmacognosia |
dc.source.none.fl_str_mv |
Revista Brasileira de Farmacognosia v.19 n.4 2009 reponame:Revista Brasileira de Farmacognosia (Online) instname:Sociedade Brasileira de Farmacognosia (SBFgnosia) instacron:SBFGNOSIA |
instname_str |
Sociedade Brasileira de Farmacognosia (SBFgnosia) |
instacron_str |
SBFGNOSIA |
institution |
SBFGNOSIA |
reponame_str |
Revista Brasileira de Farmacognosia (Online) |
collection |
Revista Brasileira de Farmacognosia (Online) |
repository.name.fl_str_mv |
Revista Brasileira de Farmacognosia (Online) - Sociedade Brasileira de Farmacognosia (SBFgnosia) |
repository.mail.fl_str_mv |
rbgnosia@ltf.ufpb.br |
_version_ |
1752122463874973696 |