ALKALOIDS FROM LEAVES OF GUATTERIA POGONOPUS (ANNONACEAE) AND THEIR CYTOTOXICITIES
Autor(a) principal: | |
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Data de Publicação: | 2018 |
Outros Autores: | , , , , , , , , , , , |
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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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 |
_version_ |
1750318119217266688 |