Bioactive alkaloids and phenolic Hippeastrum solandriflorum (Lindl.) - Amaryllidaceae

Detalhes bibliográficos
Autor(a) principal: Kaline Rodrigues Carvalho
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.
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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 CearÃ
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 CearÃ
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
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