Bioactive Indole Alkaloids from Croton echioides

Detalhes bibliográficos
Autor(a) principal: Novello,Claudio R.
Data de Publicação: 2016
Outros Autores: Marques,Luís C., Pires,Murilo E., Kutschenco,Ana P., Nakamura,Celso V., Nocchi,Samara, Sarragiotto,Maria H., Mello,João C. P.
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=S0103-50532016001202203
Resumo: Bioguided fractionation of a hydroethanolic extract from the stem bark of Croton echioides Baill. led to isolation of the new indole alkaloid N-trans-feruloyl-3,5-dihydroxyindolin-2-one as a stereoisomeric mixture and the known alkaloids N-trans-p-coumaroyl-tryptamine, N-trans-p-coumaroyl-5-hydroxytryptamine, N-trans-4-methoxy-cinnamoyl-5-hydroxytryptamine, N-trans-feruloyl-5-hydroxytryptamine (moschamine), from the ethyl acetate fraction. The flavonoids 3-o-methyl kaempferol, 3-o-methyl quercetin, 3,7-di-o-methyl quercetin and 3,3'-di-o-methyl quercetin, together with the benzoic acid derivatives 4-hydroxybenzoic acid, 4-hydroxy-3-methoxybenzoic acid and 4-hydroxy-3,5-dimethoxybenzoic acid were also isolated. Alkaloids and the flavonoids showed strong antioxidant properties in vitro radical scavenging assay (2,2-diphenyl-1-picrylhydrazyl, DPPH), with IC50 values ranging from 9.2 to 17.5 µmol L-1, lower than those of the positive control Trolox (IC50 = 17.9 µmol L-1). Alkaloids showed cytotoxic activity against the HCT-116 human cancer cell line, with IC50 values ranging from 86.8 to 210.7 µmol L-1. Compound N-trans-4-methoxy-cinnamoyl-5-hydroxytryptamine was the most active, with an IC50 value of 86.8 µmol L-1.
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spelling Bioactive Indole Alkaloids from Croton echioidesCroton echioidesEuphorbiaceaeindole alkaloidcytotoxic activityantioxidant activityBioguided fractionation of a hydroethanolic extract from the stem bark of Croton echioides Baill. led to isolation of the new indole alkaloid N-trans-feruloyl-3,5-dihydroxyindolin-2-one as a stereoisomeric mixture and the known alkaloids N-trans-p-coumaroyl-tryptamine, N-trans-p-coumaroyl-5-hydroxytryptamine, N-trans-4-methoxy-cinnamoyl-5-hydroxytryptamine, N-trans-feruloyl-5-hydroxytryptamine (moschamine), from the ethyl acetate fraction. The flavonoids 3-o-methyl kaempferol, 3-o-methyl quercetin, 3,7-di-o-methyl quercetin and 3,3'-di-o-methyl quercetin, together with the benzoic acid derivatives 4-hydroxybenzoic acid, 4-hydroxy-3-methoxybenzoic acid and 4-hydroxy-3,5-dimethoxybenzoic acid were also isolated. Alkaloids and the flavonoids showed strong antioxidant properties in vitro radical scavenging assay (2,2-diphenyl-1-picrylhydrazyl, DPPH), with IC50 values ranging from 9.2 to 17.5 µmol L-1, lower than those of the positive control Trolox (IC50 = 17.9 µmol L-1). Alkaloids showed cytotoxic activity against the HCT-116 human cancer cell line, with IC50 values ranging from 86.8 to 210.7 µmol L-1. Compound N-trans-4-methoxy-cinnamoyl-5-hydroxytryptamine was the most active, with an IC50 value of 86.8 µmol L-1.Sociedade Brasileira de Química2016-12-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532016001202203Journal of the Brazilian Chemical Society v.27 n.12 2016reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.5935/0103-5053.20160112info:eu-repo/semantics/openAccessNovello,Claudio R.Marques,Luís C.Pires,Murilo E.Kutschenco,Ana P.Nakamura,Celso V.Nocchi,SamaraSarragiotto,Maria H.Mello,João C. P.eng2016-12-01T00:00:00Zoai:scielo:S0103-50532016001202203Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2016-12-01T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false
dc.title.none.fl_str_mv Bioactive Indole Alkaloids from Croton echioides
title Bioactive Indole Alkaloids from Croton echioides
spellingShingle Bioactive Indole Alkaloids from Croton echioides
Novello,Claudio R.
Croton echioides
Euphorbiaceae
indole alkaloid
cytotoxic activity
antioxidant activity
title_short Bioactive Indole Alkaloids from Croton echioides
title_full Bioactive Indole Alkaloids from Croton echioides
title_fullStr Bioactive Indole Alkaloids from Croton echioides
title_full_unstemmed Bioactive Indole Alkaloids from Croton echioides
title_sort Bioactive Indole Alkaloids from Croton echioides
author Novello,Claudio R.
author_facet Novello,Claudio R.
Marques,Luís C.
Pires,Murilo E.
Kutschenco,Ana P.
Nakamura,Celso V.
Nocchi,Samara
Sarragiotto,Maria H.
Mello,João C. P.
author_role author
author2 Marques,Luís C.
Pires,Murilo E.
Kutschenco,Ana P.
Nakamura,Celso V.
Nocchi,Samara
Sarragiotto,Maria H.
Mello,João C. P.
author2_role author
author
author
author
author
author
author
dc.contributor.author.fl_str_mv Novello,Claudio R.
Marques,Luís C.
Pires,Murilo E.
Kutschenco,Ana P.
Nakamura,Celso V.
Nocchi,Samara
Sarragiotto,Maria H.
Mello,João C. P.
dc.subject.por.fl_str_mv Croton echioides
Euphorbiaceae
indole alkaloid
cytotoxic activity
antioxidant activity
topic Croton echioides
Euphorbiaceae
indole alkaloid
cytotoxic activity
antioxidant activity
description Bioguided fractionation of a hydroethanolic extract from the stem bark of Croton echioides Baill. led to isolation of the new indole alkaloid N-trans-feruloyl-3,5-dihydroxyindolin-2-one as a stereoisomeric mixture and the known alkaloids N-trans-p-coumaroyl-tryptamine, N-trans-p-coumaroyl-5-hydroxytryptamine, N-trans-4-methoxy-cinnamoyl-5-hydroxytryptamine, N-trans-feruloyl-5-hydroxytryptamine (moschamine), from the ethyl acetate fraction. The flavonoids 3-o-methyl kaempferol, 3-o-methyl quercetin, 3,7-di-o-methyl quercetin and 3,3'-di-o-methyl quercetin, together with the benzoic acid derivatives 4-hydroxybenzoic acid, 4-hydroxy-3-methoxybenzoic acid and 4-hydroxy-3,5-dimethoxybenzoic acid were also isolated. Alkaloids and the flavonoids showed strong antioxidant properties in vitro radical scavenging assay (2,2-diphenyl-1-picrylhydrazyl, DPPH), with IC50 values ranging from 9.2 to 17.5 µmol L-1, lower than those of the positive control Trolox (IC50 = 17.9 µmol L-1). Alkaloids showed cytotoxic activity against the HCT-116 human cancer cell line, with IC50 values ranging from 86.8 to 210.7 µmol L-1. Compound N-trans-4-methoxy-cinnamoyl-5-hydroxytryptamine was the most active, with an IC50 value of 86.8 µmol L-1.
publishDate 2016
dc.date.none.fl_str_mv 2016-12-01
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
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status_str publishedVersion
dc.identifier.uri.fl_str_mv http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532016001202203
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dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 10.5935/0103-5053.20160112
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
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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.27 n.12 2016
reponame:Journal of the Brazilian Chemical Society (Online)
instname:Sociedade Brasileira de Química (SBQ)
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instname_str Sociedade Brasileira de Química (SBQ)
instacron_str SBQ
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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
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