Xymarginatin: a new acetogenin inhibitor of mitochondrial electron transport from Xylopia emarginata Mart., Annonaceae

Detalhes bibliográficos
Autor(a) principal: Colman-Saizarbitoria,Trina
Data de Publicação: 2009
Outros Autores: Montilla,Linda, Rodriguez,Maria, Castillo,Aníbal, Hasegawa,Masahisa
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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spelling 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
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