Alcaloides isoquinolínicos isolados das partes aéreas de Worsleya procera (Lem.) Traub (Amaryllidaceae)
Autor(a) principal: | |
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Data de Publicação: | 2016 |
Tipo de documento: | Dissertação |
Idioma: | por |
Título da fonte: | Repositório Institucional da Universidade Federal do Espírito Santo (riUfes) |
Texto Completo: | http://repositorio.ufes.br/handle/10/7319 |
Resumo: | Many natural compounds have shown interesting biological and pharmacological activities and are considered important targets and one of the largest sources of new drugs, used directly or indirectly as a starting point for developing new drugs. Of plant compounds with biological potency, the alkaloids present in the Amaryllidaceae family are especially effective, for example, the alkaloid galanthamine, a selective, reversible and competitive inhibitor of the enzyme acetylcholinesterase and is marketed for the treatment of Alzheimer's disease. No study of chemical and biological characterization of the plant Worsleya procera(Lem.)Traub (Amaryllidaceae) was found in the literature and thus, for the purpose of phytochemical characterization of this plant, various chromatographic techniques were used in their extracts for the isolation and identification of alkaloids. As a result, 19 alkaloids and a mixture of two epimers alkaloids (18and 19)were isolatedfrom the aerial parts of W. procera: 3-epimacronine (1),albomaculine (2), lycorine (3), galanthine (4), tazettine (5), hippeastrine (6), O-methyllycorenine (7), 7-methoxy-O-methyllycorenina (8), homolycorine (9), 8-O-demethylhomolycorine (10), trisphaeridine (11), haemanthamine (12), 8-O-demethyl-O-methyllycorenine (13), ismine (14), 6-O-methylpretazettine (15), pretazettine (16), alkaloidwith skeleton type haemanthamine(17), haemanthidine (18), 6-epihaemanthidine (19), 8-O-demethyl-2a-hydroxyhomolycorine (20) e N-fomylismine (21), where their structures could be elucidated by the 1H NMR technique one-and two-dimensional, in compared with literature data. The alkaloid 8-O-demethyl-2a-hydroxyhomolycorineis reported for the first time from natural source.Nineisolated alkaloids(Tazettine, 3-epimacronine, albomaculine, lycorine, galanthine,hippeastrine, O-methyllycorenine, 7-methoxy-O-methyllycorenina and 8-O-demethylhomolycorine) were evaluated for antimicrobial activity, with all weak activity when compared to posivito control.The GC-MS technique proved to be a rapid and efficient technical alkaloids identification, since the analysis results of W.proceraplantextractsfound that the majority were alkaloids 22with skeleton homolicorina type, skeleton lycorinetype and skeletontazetina type, which was confirmed by the total mass of alkaloid obtained |
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Borges, Warley de SouzaMoraes, Carolina TorresCunha Neto, Álvaro2018-08-01T21:36:53Z2018-08-012018-08-01T21:36:53Z2016-10-24Many natural compounds have shown interesting biological and pharmacological activities and are considered important targets and one of the largest sources of new drugs, used directly or indirectly as a starting point for developing new drugs. Of plant compounds with biological potency, the alkaloids present in the Amaryllidaceae family are especially effective, for example, the alkaloid galanthamine, a selective, reversible and competitive inhibitor of the enzyme acetylcholinesterase and is marketed for the treatment of Alzheimer's disease. No study of chemical and biological characterization of the plant Worsleya procera(Lem.)Traub (Amaryllidaceae) was found in the literature and thus, for the purpose of phytochemical characterization of this plant, various chromatographic techniques were used in their extracts for the isolation and identification of alkaloids. As a result, 19 alkaloids and a mixture of two epimers alkaloids (18and 19)were isolatedfrom the aerial parts of W. procera: 3-epimacronine (1),albomaculine (2), lycorine (3), galanthine (4), tazettine (5), hippeastrine (6), O-methyllycorenine (7), 7-methoxy-O-methyllycorenina (8), homolycorine (9), 8-O-demethylhomolycorine (10), trisphaeridine (11), haemanthamine (12), 8-O-demethyl-O-methyllycorenine (13), ismine (14), 6-O-methylpretazettine (15), pretazettine (16), alkaloidwith skeleton type haemanthamine(17), haemanthidine (18), 6-epihaemanthidine (19), 8-O-demethyl-2a-hydroxyhomolycorine (20) e N-fomylismine (21), where their structures could be elucidated by the 1H NMR technique one-and two-dimensional, in compared with literature data. The alkaloid 8-O-demethyl-2a-hydroxyhomolycorineis reported for the first time from natural source.Nineisolated alkaloids(Tazettine, 3-epimacronine, albomaculine, lycorine, galanthine,hippeastrine, O-methyllycorenine, 7-methoxy-O-methyllycorenina and 8-O-demethylhomolycorine) were evaluated for antimicrobial activity, with all weak activity when compared to posivito control.The GC-MS technique proved to be a rapid and efficient technical alkaloids identification, since the analysis results of W.proceraplantextractsfound that the majority were alkaloids 22with skeleton homolicorina type, skeleton lycorinetype and skeletontazetina type, which was confirmed by the total mass of alkaloid obtainedMuitos compostos naturais têm apresentado interessantes atividades biológicas e farmacológicas, sendo considerados alvos importantes e uma das maiores fontes de novos fármacos, usados diretamente ou indiretamente, como ponto de partida para o desenvolvimento de novos medicamentos. Dos compostos vegetais com potencial biológico, os alcaloides presentes na família Amaryllidaceae são especialmente efetivos, como por exemplo, o alcaloide galantamina, um inibidor seletivo, reversível e competitivo da enzima acetilcolinesterase, sendo comercializado para o tratamento da doença de Alzheimer. Nenhum estudo de caracterização química e biológica da planta Worsleya procera (Lem.) Traub (Amaryllidaceae) foi encontrado na literatura e desta forma, com o objetivo de caracterização fitoquímica desta planta, diversas técnicas cromatográficas foram empregadas em seus extratos para o isolamento e identificação dos alcaloides. Como resultado, foram isolados 19 alcaloides e uma mistura de dois alcaloides epímeros (18 e 19) a partir das partes aéreas de W. procera: 3-epimacronina (1), albomaculina (2), licorina (3), galantina (4), tazetina (5), hippeastrina (6), O-metillicorenina (7), 7-metoxi-O-metillicorenina (8), homolicorina (9), 8-O-desmetilhomolicorina (10), trisfaeridina (11), haemantamina (12), 8-O-desmetil-O-metillicorenina (13), ismina (14), 6-O-metilpretazetina (15), pretazetina (16), alcaloide com esqueleto do tipo haemantamina (17), haemantidina (18), 6-epihaemantidina (19), 8-O-desmetil-2α-hidroxihomolicorina (20) e N-fomilismina (21), onde suas estruturas foram elucidadas através da técnica de RMN de 1H uno e bidimencional e em comparação com dados da literatura. O alcaloide 8-O-desmetil-2α-hidroxihomolicorina (20) é relatado pela primeira vez a partir de fonte natural. Nove alcaloides isolados (Tazetina, 3-epimacronina, albomaculina, licorina, galantina, hippeastrina, O-metillicorenina, 7-metoxi-O-metillicorenina e 8-O-desmetilhomolicorina) foram avaliados quanto a atividade antimicrobiana, apresentando todos atividade fraca, quando comparado ao controle posivito. A técnica de CG-EM mostrou ser uma técnica rápida e eficiente de identificação de alcaloides, uma vez que, os resultados das análises dos extratos da planta 20 W.procera verificaram que os alcaloides majoritários eram os alcaloides com esqueleto do tipo homolicorina, esqueleto com tipo licorina e esqueleto do tipo tazetina, o que foi confirmado pelas massas totais dos alcaloides obtidosTextMORAES, Carolina Torres. Alcaloides isoquinolínicos isolados das partes aéreas de Worsleya procera (Lem.) Traub (Amaryllidaceae). 2016. 186 f. Dissertação (Mestrado em Química) – Universidade Federal do Espírito Santo, Centro de Ciências Exatas, Vitória, 2016.http://repositorio.ufes.br/handle/10/7319porUniversidade Federal do Espírito SantoMestrado em QuímicaPrograma de Pós-Graduação em QuímicaUFESBRCentro de Ciências ExatasAlkaloidsPhytochemistryWorsleya proceraAmaryllidaceaeFitoquímicaAlcalóidesAmarilidáceaQuímica vegetalQuímica54Alcaloides isoquinolínicos isolados das partes aéreas de Worsleya procera (Lem.) Traub (Amaryllidaceae)info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesisinfo:eu-repo/semantics/openAccessreponame:Repositório Institucional da Universidade Federal do Espírito Santo (riUfes)instname:Universidade Federal do Espírito Santo (UFES)instacron:UFESORIGINALDissertação FINAL Carolina PDF (1).pdfapplication/pdf4291486http://repositorio.ufes.br/bitstreams/bb3d9ca0-5be6-4c4e-9436-b8d34503f835/download59f56d25bee7b93746d0354c4cf930afMD5110/73192024-06-28 17:52:29.406oai:repositorio.ufes.br:10/7319http://repositorio.ufes.brRepositório InstitucionalPUBhttp://repositorio.ufes.br/oai/requestopendoar:21082024-06-28T17:52:29Repositório Institucional da Universidade Federal do Espírito Santo (riUfes) - Universidade Federal do Espírito Santo (UFES)false |
dc.title.none.fl_str_mv |
Alcaloides isoquinolínicos isolados das partes aéreas de Worsleya procera (Lem.) Traub (Amaryllidaceae) |
title |
Alcaloides isoquinolínicos isolados das partes aéreas de Worsleya procera (Lem.) Traub (Amaryllidaceae) |
spellingShingle |
Alcaloides isoquinolínicos isolados das partes aéreas de Worsleya procera (Lem.) Traub (Amaryllidaceae) Moraes, Carolina Torres Alkaloids Phytochemistry Worsleya procera Amaryllidaceae Fitoquímica Química Alcalóides Amarilidácea Química vegetal 54 |
title_short |
Alcaloides isoquinolínicos isolados das partes aéreas de Worsleya procera (Lem.) Traub (Amaryllidaceae) |
title_full |
Alcaloides isoquinolínicos isolados das partes aéreas de Worsleya procera (Lem.) Traub (Amaryllidaceae) |
title_fullStr |
Alcaloides isoquinolínicos isolados das partes aéreas de Worsleya procera (Lem.) Traub (Amaryllidaceae) |
title_full_unstemmed |
Alcaloides isoquinolínicos isolados das partes aéreas de Worsleya procera (Lem.) Traub (Amaryllidaceae) |
title_sort |
Alcaloides isoquinolínicos isolados das partes aéreas de Worsleya procera (Lem.) Traub (Amaryllidaceae) |
author |
Moraes, Carolina Torres |
author_facet |
Moraes, Carolina Torres |
author_role |
author |
dc.contributor.advisor1.fl_str_mv |
Borges, Warley de Souza |
dc.contributor.author.fl_str_mv |
Moraes, Carolina Torres |
dc.contributor.referee1.fl_str_mv |
Cunha Neto, Álvaro |
contributor_str_mv |
Borges, Warley de Souza Cunha Neto, Álvaro |
dc.subject.eng.fl_str_mv |
Alkaloids Phytochemistry |
topic |
Alkaloids Phytochemistry Worsleya procera Amaryllidaceae Fitoquímica Química Alcalóides Amarilidácea Química vegetal 54 |
dc.subject.por.fl_str_mv |
Worsleya procera Amaryllidaceae Fitoquímica |
dc.subject.cnpq.fl_str_mv |
Química |
dc.subject.br-rjbn.none.fl_str_mv |
Alcalóides Amarilidácea Química vegetal |
dc.subject.udc.none.fl_str_mv |
54 |
description |
Many natural compounds have shown interesting biological and pharmacological activities and are considered important targets and one of the largest sources of new drugs, used directly or indirectly as a starting point for developing new drugs. Of plant compounds with biological potency, the alkaloids present in the Amaryllidaceae family are especially effective, for example, the alkaloid galanthamine, a selective, reversible and competitive inhibitor of the enzyme acetylcholinesterase and is marketed for the treatment of Alzheimer's disease. No study of chemical and biological characterization of the plant Worsleya procera(Lem.)Traub (Amaryllidaceae) was found in the literature and thus, for the purpose of phytochemical characterization of this plant, various chromatographic techniques were used in their extracts for the isolation and identification of alkaloids. As a result, 19 alkaloids and a mixture of two epimers alkaloids (18and 19)were isolatedfrom the aerial parts of W. procera: 3-epimacronine (1),albomaculine (2), lycorine (3), galanthine (4), tazettine (5), hippeastrine (6), O-methyllycorenine (7), 7-methoxy-O-methyllycorenina (8), homolycorine (9), 8-O-demethylhomolycorine (10), trisphaeridine (11), haemanthamine (12), 8-O-demethyl-O-methyllycorenine (13), ismine (14), 6-O-methylpretazettine (15), pretazettine (16), alkaloidwith skeleton type haemanthamine(17), haemanthidine (18), 6-epihaemanthidine (19), 8-O-demethyl-2a-hydroxyhomolycorine (20) e N-fomylismine (21), where their structures could be elucidated by the 1H NMR technique one-and two-dimensional, in compared with literature data. The alkaloid 8-O-demethyl-2a-hydroxyhomolycorineis reported for the first time from natural source.Nineisolated alkaloids(Tazettine, 3-epimacronine, albomaculine, lycorine, galanthine,hippeastrine, O-methyllycorenine, 7-methoxy-O-methyllycorenina and 8-O-demethylhomolycorine) were evaluated for antimicrobial activity, with all weak activity when compared to posivito control.The GC-MS technique proved to be a rapid and efficient technical alkaloids identification, since the analysis results of W.proceraplantextractsfound that the majority were alkaloids 22with skeleton homolicorina type, skeleton lycorinetype and skeletontazetina type, which was confirmed by the total mass of alkaloid obtained |
publishDate |
2016 |
dc.date.issued.fl_str_mv |
2016-10-24 |
dc.date.accessioned.fl_str_mv |
2018-08-01T21:36:53Z |
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2018-08-01 2018-08-01T21:36:53Z |
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info:eu-repo/semantics/publishedVersion |
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info:eu-repo/semantics/masterThesis |
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masterThesis |
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publishedVersion |
dc.identifier.citation.fl_str_mv |
MORAES, Carolina Torres. Alcaloides isoquinolínicos isolados das partes aéreas de Worsleya procera (Lem.) Traub (Amaryllidaceae). 2016. 186 f. Dissertação (Mestrado em Química) – Universidade Federal do Espírito Santo, Centro de Ciências Exatas, Vitória, 2016. |
dc.identifier.uri.fl_str_mv |
http://repositorio.ufes.br/handle/10/7319 |
identifier_str_mv |
MORAES, Carolina Torres. Alcaloides isoquinolínicos isolados das partes aéreas de Worsleya procera (Lem.) Traub (Amaryllidaceae). 2016. 186 f. Dissertação (Mestrado em Química) – Universidade Federal do Espírito Santo, Centro de Ciências Exatas, Vitória, 2016. |
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Universidade Federal do Espírito Santo Mestrado em Química |
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Universidade Federal do Espírito Santo Mestrado em Química |
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