ALKALOIDS FROM LEAVES OF GUATTERIA POGONOPUS (ANNONACEAE) AND THEIR CYTOTOXICITIES

Detalhes bibliográficos
Autor(a) principal: Santos,Maria de Fátima C.
Data de Publicação: 2018
Outros Autores: Fontes,José Eraldo N., Dutra,Lívia M., Bomfim,Larissa M., Costa,Cinara O. D., Moraes,Valéria R. S., Barison,Andersson, Soares,Milena B. P., Silva,Felipe Moura A. da, Almeida,Jackson R. G. da Silva, Koolen,Héctor H. F., Bezerra,Daniel P., Costa,Emmanoel Vilaça
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Química Nova (Online)
Texto Completo: http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0100-40422018000800884
Resumo: The phytochemical investigation of the alkaloid-rich fraction obtained from the leaves of Guatteria pogonopus Mart. (Annonaceae) allowed the isolation and identification for the first time in this species of: (+)-nornuciferine (1), a mixture of 1 and (+)-anonaine (2), (+)-isocorydine (3), (+)-nuciferine (4), (+)-roemerine (5), (-)-tetrahydropseudocolumbamine (6), a mixture of 6, liriodenine (9) and lysicamine (10), a mixture of 1,2,9-trimethoxy-10-hydroxyaporphine (7) and bulbocapnine (8), 9, 10, and (+)-N-methyllindicarpine (11). Compounds 6, 7, 8, and 11 have not been previously reported in the family Annonaceae. Furthermore, the formerly synthetic 1,2,9-trimethoxyaporfin-10-ol (7) is described for the first time as a natural aporphine alkaloid herein. The chemical structures were established by 1D and 2D NMR as well as in comparison with data previously reported in the literature. The cytotoxic activity of the alkaloids was evaluated against tumor (B16-F10, HepG2, HL-60, and K562) and non-tumor (PBMC) cell lines. Alkaloid 1 presented significant activity against HepG2 cell lines with IC50 of 9.60 µmol L-1 while the mixture of 6, 9 and 10 displayed strong cytotoxic activity against HL-60 and K562 cell lines with IC50 values of 3.41 an 8.50 µmol L-1, respectively.
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spelling ALKALOIDS FROM LEAVES OF GUATTERIA POGONOPUS (ANNONACEAE) AND THEIR CYTOTOXICITIESalkaloidsGuatteria pogonopusleavesAnnonaceaeNMRcytotoxicityThe phytochemical investigation of the alkaloid-rich fraction obtained from the leaves of Guatteria pogonopus Mart. (Annonaceae) allowed the isolation and identification for the first time in this species of: (+)-nornuciferine (1), a mixture of 1 and (+)-anonaine (2), (+)-isocorydine (3), (+)-nuciferine (4), (+)-roemerine (5), (-)-tetrahydropseudocolumbamine (6), a mixture of 6, liriodenine (9) and lysicamine (10), a mixture of 1,2,9-trimethoxy-10-hydroxyaporphine (7) and bulbocapnine (8), 9, 10, and (+)-N-methyllindicarpine (11). Compounds 6, 7, 8, and 11 have not been previously reported in the family Annonaceae. Furthermore, the formerly synthetic 1,2,9-trimethoxyaporfin-10-ol (7) is described for the first time as a natural aporphine alkaloid herein. The chemical structures were established by 1D and 2D NMR as well as in comparison with data previously reported in the literature. The cytotoxic activity of the alkaloids was evaluated against tumor (B16-F10, HepG2, HL-60, and K562) and non-tumor (PBMC) cell lines. Alkaloid 1 presented significant activity against HepG2 cell lines with IC50 of 9.60 µmol L-1 while the mixture of 6, 9 and 10 displayed strong cytotoxic activity against HL-60 and K562 cell lines with IC50 values of 3.41 an 8.50 µmol L-1, respectively.Sociedade Brasileira de Química2018-08-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0100-40422018000800884Química Nova v.41 n.8 2018reponame:Química Nova (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.21577/0100-4042.20170258info:eu-repo/semantics/openAccessSantos,Maria de Fátima C.Fontes,José Eraldo N.Dutra,Lívia M.Bomfim,Larissa M.Costa,Cinara O. D.Moraes,Valéria R. S.Barison,AnderssonSoares,Milena B. P.Silva,Felipe Moura A. daAlmeida,Jackson R. G. da SilvaKoolen,Héctor H. F.Bezerra,Daniel P.Costa,Emmanoel Vilaçaeng2018-10-16T00:00:00Zoai:scielo:S0100-40422018000800884Revistahttps://www.scielo.br/j/qn/ONGhttps://old.scielo.br/oai/scielo-oai.phpquimicanova@sbq.org.br1678-70640100-4042opendoar:2018-10-16T00:00Química Nova (Online) - Sociedade Brasileira de Química (SBQ)false
dc.title.none.fl_str_mv ALKALOIDS FROM LEAVES OF GUATTERIA POGONOPUS (ANNONACEAE) AND THEIR CYTOTOXICITIES
title ALKALOIDS FROM LEAVES OF GUATTERIA POGONOPUS (ANNONACEAE) AND THEIR CYTOTOXICITIES
spellingShingle ALKALOIDS FROM LEAVES OF GUATTERIA POGONOPUS (ANNONACEAE) AND THEIR CYTOTOXICITIES
Santos,Maria de Fátima C.
alkaloids
Guatteria pogonopus
leaves
Annonaceae
NMR
cytotoxicity
title_short ALKALOIDS FROM LEAVES OF GUATTERIA POGONOPUS (ANNONACEAE) AND THEIR CYTOTOXICITIES
title_full ALKALOIDS FROM LEAVES OF GUATTERIA POGONOPUS (ANNONACEAE) AND THEIR CYTOTOXICITIES
title_fullStr ALKALOIDS FROM LEAVES OF GUATTERIA POGONOPUS (ANNONACEAE) AND THEIR CYTOTOXICITIES
title_full_unstemmed ALKALOIDS FROM LEAVES OF GUATTERIA POGONOPUS (ANNONACEAE) AND THEIR CYTOTOXICITIES
title_sort ALKALOIDS FROM LEAVES OF GUATTERIA POGONOPUS (ANNONACEAE) AND THEIR CYTOTOXICITIES
author Santos,Maria de Fátima C.
author_facet Santos,Maria de Fátima C.
Fontes,José Eraldo N.
Dutra,Lívia M.
Bomfim,Larissa M.
Costa,Cinara O. D.
Moraes,Valéria R. S.
Barison,Andersson
Soares,Milena B. P.
Silva,Felipe Moura A. da
Almeida,Jackson R. G. da Silva
Koolen,Héctor H. F.
Bezerra,Daniel P.
Costa,Emmanoel Vilaça
author_role author
author2 Fontes,José Eraldo N.
Dutra,Lívia M.
Bomfim,Larissa M.
Costa,Cinara O. D.
Moraes,Valéria R. S.
Barison,Andersson
Soares,Milena B. P.
Silva,Felipe Moura A. da
Almeida,Jackson R. G. da Silva
Koolen,Héctor H. F.
Bezerra,Daniel P.
Costa,Emmanoel Vilaça
author2_role author
author
author
author
author
author
author
author
author
author
author
author
dc.contributor.author.fl_str_mv Santos,Maria de Fátima C.
Fontes,José Eraldo N.
Dutra,Lívia M.
Bomfim,Larissa M.
Costa,Cinara O. D.
Moraes,Valéria R. S.
Barison,Andersson
Soares,Milena B. P.
Silva,Felipe Moura A. da
Almeida,Jackson R. G. da Silva
Koolen,Héctor H. F.
Bezerra,Daniel P.
Costa,Emmanoel Vilaça
dc.subject.por.fl_str_mv alkaloids
Guatteria pogonopus
leaves
Annonaceae
NMR
cytotoxicity
topic alkaloids
Guatteria pogonopus
leaves
Annonaceae
NMR
cytotoxicity
description The phytochemical investigation of the alkaloid-rich fraction obtained from the leaves of Guatteria pogonopus Mart. (Annonaceae) allowed the isolation and identification for the first time in this species of: (+)-nornuciferine (1), a mixture of 1 and (+)-anonaine (2), (+)-isocorydine (3), (+)-nuciferine (4), (+)-roemerine (5), (-)-tetrahydropseudocolumbamine (6), a mixture of 6, liriodenine (9) and lysicamine (10), a mixture of 1,2,9-trimethoxy-10-hydroxyaporphine (7) and bulbocapnine (8), 9, 10, and (+)-N-methyllindicarpine (11). Compounds 6, 7, 8, and 11 have not been previously reported in the family Annonaceae. Furthermore, the formerly synthetic 1,2,9-trimethoxyaporfin-10-ol (7) is described for the first time as a natural aporphine alkaloid herein. The chemical structures were established by 1D and 2D NMR as well as in comparison with data previously reported in the literature. The cytotoxic activity of the alkaloids was evaluated against tumor (B16-F10, HepG2, HL-60, and K562) and non-tumor (PBMC) cell lines. Alkaloid 1 presented significant activity against HepG2 cell lines with IC50 of 9.60 µmol L-1 while the mixture of 6, 9 and 10 displayed strong cytotoxic activity against HL-60 and K562 cell lines with IC50 values of 3.41 an 8.50 µmol L-1, respectively.
publishDate 2018
dc.date.none.fl_str_mv 2018-08-01
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=S0100-40422018000800884
url http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0100-40422018000800884
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 10.21577/0100-4042.20170258
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.41 n.8 2018
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
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