Bioactive Indole Alkaloids from Croton echioides
Autor(a) principal: | |
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Data de Publicação: | 2016 |
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=S0103-50532016001202203 |
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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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 |
format |
article |
status_str |
publishedVersion |
dc.identifier.uri.fl_str_mv |
http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532016001202203 |
url |
http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532016001202203 |
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 |
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.27 n.12 2016 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 |
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1750318179084664832 |