Bioactive alkaloids and phenolic Hippeastrum solandriflorum (Lindl.) - Amaryllidaceae
Autor(a) principal: | |
---|---|
Data de Publicação: | 2014 |
Tipo de documento: | Dissertação |
Idioma: | por |
Título da fonte: | Biblioteca Digital de Teses e Dissertações da UFC |
Texto Completo: | http://www.teses.ufc.br/tde_busca/arquivo.php?codArquivo=13544 |
Resumo: | This work describes the phytochemical study of Hippeastrum solandriflorum(Amaryllidaceae)aiming the isolation and structural elucidation of new bioactive compounds, as well as its pharmacological investigation. The chemical investigation realized with the EtOH extract from bulbs, through chromatographic methods, including HPLC (reverse phase), resulting inthe isolation of ten compounds: a furan derivative: 5-(hydroxymethyl)furan-2-carbaldehyde(HS-1), two phenolic derivatives: piscidic acid (HS-2), eucomic acid (HS-3), and seven isoquinoline alkaloids: narciclasin ( HS-4), 2α-hydroxypseudolycorin (HS-5), 10α-hydroxy homolycorin (HS-6), galantamin (HS-7), sanguinin (HS-8),N-oxid galantamin (HS-9) andnarcissidin (HS10). The alkaloids (HS-5) and (HS-6) are being reported for the first time inthe literature, while the other ones have been isolated for the first time in the investigated species. The structures of all isolated compounds were determined based on spectrometricmethods (IR, HRMS, NMR 1H and13Câ1D and 2D), besides comparison with published data. The cytotoxic potential of all alkaloids were evaluated against several tumor cell lines:colon (HCT-116), leukemia (HL-60), ovary (OVCAR-8) and brain (SF-295) showing IC50ranging from 0.01 to 35.7 μM. |
id |
UFC_9fdd0e4182586fc82a4a14648ac8e237 |
---|---|
oai_identifier_str |
oai:www.teses.ufc.br:9027 |
network_acronym_str |
UFC |
network_name_str |
Biblioteca Digital de Teses e Dissertações da UFC |
spelling |
info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesisBioactive alkaloids and phenolic Hippeastrum solandriflorum (Lindl.) - AmaryllidaceaeAlcalÃides bioativos e fenÃlicos de Hippeastrum solandriflorum (Lindl.) - Amaryllidaceae2014-10-31Maria da ConceiÃÃo de Menezes Torres03888817471http://lattes.cnpq.br/7638517746936259 Telma Leda Gomes de Lemos04511700320http://buscatextual.cnpq.br/buscatextual/visualizacv.jsp?id=K4783204Z7Kirley Marques Canuto78980496320http://lattes.cnpq.br/805107961310889202871015333http://lattes.cnpq.br/0906720026527644Kaline Rodrigues CarvalhoUniversidade Federal do CearÃPrograma de PÃs-GraduaÃÃo em QuÃmica UFCBRAmaryllidaceae Hippeastrum solandriflorumAlcalÃides isoquinolÃnicosAtividade citotÃxicaAmaryllidaceae Hippeastrum solandriflorumIsoquinoline alkaloidsCytotoxic activityQUIMICA DOS PRODUTOS NATURAISThis work describes the phytochemical study of Hippeastrum solandriflorum(Amaryllidaceae)aiming the isolation and structural elucidation of new bioactive compounds, as well as its pharmacological investigation. The chemical investigation realized with the EtOH extract from bulbs, through chromatographic methods, including HPLC (reverse phase), resulting inthe isolation of ten compounds: a furan derivative: 5-(hydroxymethyl)furan-2-carbaldehyde(HS-1), two phenolic derivatives: piscidic acid (HS-2), eucomic acid (HS-3), and seven isoquinoline alkaloids: narciclasin ( HS-4), 2α-hydroxypseudolycorin (HS-5), 10α-hydroxy homolycorin (HS-6), galantamin (HS-7), sanguinin (HS-8),N-oxid galantamin (HS-9) andnarcissidin (HS10). The alkaloids (HS-5) and (HS-6) are being reported for the first time inthe literature, while the other ones have been isolated for the first time in the investigated species. The structures of all isolated compounds were determined based on spectrometricmethods (IR, HRMS, NMR 1H and13Câ1D and 2D), besides comparison with published data. The cytotoxic potential of all alkaloids were evaluated against several tumor cell lines:colon (HCT-116), leukemia (HL-60), ovary (OVCAR-8) and brain (SF-295) showing IC50ranging from 0.01 to 35.7 μM.Este trabalho descreve o estudo fitoquÃmico de Hippeastrum solandriflorum (Amaryllidaceae) visando o isolamento e elucidaÃÃo estrutural de novos constituintes quÃmicos bioativos, bem como o estudo farmacolÃgico dos compostos obtidos. A investigaÃÃo quÃmica realizada com o extrato etanÃlico dos bulbos, atravÃs de mÃtodos cromatogrÃficos, incluindo CLAE (fase reversa), resultou no isolamento e identificaÃÃo de dez substÃncias, sendo um derivado do furano: 5-(hidroximetil)furan-2-carbaldeido (HS-1), dois derivados fenÃlicos: acido piscidico(HS-2), acido eucÃmico (HS-3) e sete alcaloides isoquinolÃnicos: Narciclasina (HS-4), 2α-hidroxipseudolicorina (HS-5), 10αhidroxi-homolicorina (HS-6), Galantamina (HS-7), Sanguinina (HS-8),N-oxido galantamina (HS-9), Narcissidina (HS-10). Os alcaloides (HS-5)e (HS-6) esta sendo relatado pela primeira vez na literatura e os demais como sendo inÃditos na espÃcie estudada. As substÃncias isoladas tiveram suas estruturas elucidadas por mÃtodos espectromÃtricos (IV, IES-EM e RMN de1H e13C 1D e 2D), alÃm de comparaÃÃo com dados da literatura. O potencial citotÃxicodos alcaloides isolados foi avaliado frente Ãs linhagens decÃlulas tumorais humanas: cÃlon (HCT-116), leucemia (HL-60), ovÃrio (OVCAR-8) e cÃrebro (SF-295) mostrando valores IC50 variando 0,01â35,7 μM.http://www.teses.ufc.br/tde_busca/arquivo.php?codArquivo=13544application/pdfinfo:eu-repo/semantics/openAccessporreponame:Biblioteca Digital de Teses e Dissertações da UFCinstname:Universidade Federal do Cearáinstacron:UFC2019-01-21T11:26:49Zmail@mail.com - |
dc.title.en.fl_str_mv |
Bioactive alkaloids and phenolic Hippeastrum solandriflorum (Lindl.) - Amaryllidaceae |
dc.title.alternative.pt.fl_str_mv |
AlcalÃides bioativos e fenÃlicos de Hippeastrum solandriflorum (Lindl.) - Amaryllidaceae |
title |
Bioactive alkaloids and phenolic Hippeastrum solandriflorum (Lindl.) - Amaryllidaceae |
spellingShingle |
Bioactive alkaloids and phenolic Hippeastrum solandriflorum (Lindl.) - Amaryllidaceae Kaline Rodrigues Carvalho Amaryllidaceae Hippeastrum solandriflorum AlcalÃides isoquinolÃnicos Atividade citotÃxica Amaryllidaceae Hippeastrum solandriflorum Isoquinoline alkaloids Cytotoxic activity QUIMICA DOS PRODUTOS NATURAIS |
title_short |
Bioactive alkaloids and phenolic Hippeastrum solandriflorum (Lindl.) - Amaryllidaceae |
title_full |
Bioactive alkaloids and phenolic Hippeastrum solandriflorum (Lindl.) - Amaryllidaceae |
title_fullStr |
Bioactive alkaloids and phenolic Hippeastrum solandriflorum (Lindl.) - Amaryllidaceae |
title_full_unstemmed |
Bioactive alkaloids and phenolic Hippeastrum solandriflorum (Lindl.) - Amaryllidaceae |
title_sort |
Bioactive alkaloids and phenolic Hippeastrum solandriflorum (Lindl.) - Amaryllidaceae |
author |
Kaline Rodrigues Carvalho |
author_facet |
Kaline Rodrigues Carvalho |
author_role |
author |
dc.contributor.advisor1.fl_str_mv |
Maria da ConceiÃÃo de Menezes Torres |
dc.contributor.advisor1ID.fl_str_mv |
03888817471 |
dc.contributor.advisor1Lattes.fl_str_mv |
http://lattes.cnpq.br/7638517746936259 |
dc.contributor.referee1.fl_str_mv |
Telma Leda Gomes de Lemos |
dc.contributor.referee1ID.fl_str_mv |
04511700320 |
dc.contributor.referee1Lattes.fl_str_mv |
http://buscatextual.cnpq.br/buscatextual/visualizacv.jsp?id=K4783204Z7 |
dc.contributor.referee2.fl_str_mv |
Kirley Marques Canuto |
dc.contributor.referee2ID.fl_str_mv |
78980496320 |
dc.contributor.referee2Lattes.fl_str_mv |
http://lattes.cnpq.br/8051079613108892 |
dc.contributor.authorID.fl_str_mv |
02871015333 |
dc.contributor.authorLattes.fl_str_mv |
http://lattes.cnpq.br/0906720026527644 |
dc.contributor.author.fl_str_mv |
Kaline Rodrigues Carvalho |
contributor_str_mv |
Maria da ConceiÃÃo de Menezes Torres Telma Leda Gomes de Lemos Kirley Marques Canuto |
dc.subject.por.fl_str_mv |
Amaryllidaceae Hippeastrum solandriflorum AlcalÃides isoquinolÃnicos Atividade citotÃxica |
topic |
Amaryllidaceae Hippeastrum solandriflorum AlcalÃides isoquinolÃnicos Atividade citotÃxica Amaryllidaceae Hippeastrum solandriflorum Isoquinoline alkaloids Cytotoxic activity QUIMICA DOS PRODUTOS NATURAIS |
dc.subject.eng.fl_str_mv |
Amaryllidaceae Hippeastrum solandriflorum Isoquinoline alkaloids Cytotoxic activity |
dc.subject.cnpq.fl_str_mv |
QUIMICA DOS PRODUTOS NATURAIS |
dc.description.abstract.por.fl_txt_mv |
This work describes the phytochemical study of Hippeastrum solandriflorum(Amaryllidaceae)aiming the isolation and structural elucidation of new bioactive compounds, as well as its pharmacological investigation. The chemical investigation realized with the EtOH extract from bulbs, through chromatographic methods, including HPLC (reverse phase), resulting inthe isolation of ten compounds: a furan derivative: 5-(hydroxymethyl)furan-2-carbaldehyde(HS-1), two phenolic derivatives: piscidic acid (HS-2), eucomic acid (HS-3), and seven isoquinoline alkaloids: narciclasin ( HS-4), 2α-hydroxypseudolycorin (HS-5), 10α-hydroxy homolycorin (HS-6), galantamin (HS-7), sanguinin (HS-8),N-oxid galantamin (HS-9) andnarcissidin (HS10). The alkaloids (HS-5) and (HS-6) are being reported for the first time inthe literature, while the other ones have been isolated for the first time in the investigated species. The structures of all isolated compounds were determined based on spectrometricmethods (IR, HRMS, NMR 1H and13Câ1D and 2D), besides comparison with published data. The cytotoxic potential of all alkaloids were evaluated against several tumor cell lines:colon (HCT-116), leukemia (HL-60), ovary (OVCAR-8) and brain (SF-295) showing IC50ranging from 0.01 to 35.7 μM. Este trabalho descreve o estudo fitoquÃmico de Hippeastrum solandriflorum (Amaryllidaceae) visando o isolamento e elucidaÃÃo estrutural de novos constituintes quÃmicos bioativos, bem como o estudo farmacolÃgico dos compostos obtidos. A investigaÃÃo quÃmica realizada com o extrato etanÃlico dos bulbos, atravÃs de mÃtodos cromatogrÃficos, incluindo CLAE (fase reversa), resultou no isolamento e identificaÃÃo de dez substÃncias, sendo um derivado do furano: 5-(hidroximetil)furan-2-carbaldeido (HS-1), dois derivados fenÃlicos: acido piscidico(HS-2), acido eucÃmico (HS-3) e sete alcaloides isoquinolÃnicos: Narciclasina (HS-4), 2α-hidroxipseudolicorina (HS-5), 10αhidroxi-homolicorina (HS-6), Galantamina (HS-7), Sanguinina (HS-8),N-oxido galantamina (HS-9), Narcissidina (HS-10). Os alcaloides (HS-5)e (HS-6) esta sendo relatado pela primeira vez na literatura e os demais como sendo inÃditos na espÃcie estudada. As substÃncias isoladas tiveram suas estruturas elucidadas por mÃtodos espectromÃtricos (IV, IES-EM e RMN de1H e13C 1D e 2D), alÃm de comparaÃÃo com dados da literatura. O potencial citotÃxicodos alcaloides isolados foi avaliado frente Ãs linhagens decÃlulas tumorais humanas: cÃlon (HCT-116), leucemia (HL-60), ovÃrio (OVCAR-8) e cÃrebro (SF-295) mostrando valores IC50 variando 0,01â35,7 μM. |
description |
This work describes the phytochemical study of Hippeastrum solandriflorum(Amaryllidaceae)aiming the isolation and structural elucidation of new bioactive compounds, as well as its pharmacological investigation. The chemical investigation realized with the EtOH extract from bulbs, through chromatographic methods, including HPLC (reverse phase), resulting inthe isolation of ten compounds: a furan derivative: 5-(hydroxymethyl)furan-2-carbaldehyde(HS-1), two phenolic derivatives: piscidic acid (HS-2), eucomic acid (HS-3), and seven isoquinoline alkaloids: narciclasin ( HS-4), 2α-hydroxypseudolycorin (HS-5), 10α-hydroxy homolycorin (HS-6), galantamin (HS-7), sanguinin (HS-8),N-oxid galantamin (HS-9) andnarcissidin (HS10). The alkaloids (HS-5) and (HS-6) are being reported for the first time inthe literature, while the other ones have been isolated for the first time in the investigated species. The structures of all isolated compounds were determined based on spectrometricmethods (IR, HRMS, NMR 1H and13Câ1D and 2D), besides comparison with published data. The cytotoxic potential of all alkaloids were evaluated against several tumor cell lines:colon (HCT-116), leukemia (HL-60), ovary (OVCAR-8) and brain (SF-295) showing IC50ranging from 0.01 to 35.7 μM. |
publishDate |
2014 |
dc.date.issued.fl_str_mv |
2014-10-31 |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/masterThesis |
status_str |
publishedVersion |
format |
masterThesis |
dc.identifier.uri.fl_str_mv |
http://www.teses.ufc.br/tde_busca/arquivo.php?codArquivo=13544 |
url |
http://www.teses.ufc.br/tde_busca/arquivo.php?codArquivo=13544 |
dc.language.iso.fl_str_mv |
por |
language |
por |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
dc.format.none.fl_str_mv |
application/pdf |
dc.publisher.none.fl_str_mv |
Universidade Federal do Cearà |
dc.publisher.program.fl_str_mv |
Programa de PÃs-GraduaÃÃo em QuÃmica |
dc.publisher.initials.fl_str_mv |
UFC |
dc.publisher.country.fl_str_mv |
BR |
publisher.none.fl_str_mv |
Universidade Federal do Cearà |
dc.source.none.fl_str_mv |
reponame:Biblioteca Digital de Teses e Dissertações da UFC instname:Universidade Federal do Ceará instacron:UFC |
reponame_str |
Biblioteca Digital de Teses e Dissertações da UFC |
collection |
Biblioteca Digital de Teses e Dissertações da UFC |
instname_str |
Universidade Federal do Ceará |
instacron_str |
UFC |
institution |
UFC |
repository.name.fl_str_mv |
-
|
repository.mail.fl_str_mv |
mail@mail.com |
_version_ |
1643295199880806400 |