Estudo químico em alcaloides de Hippeastrum reginae (L.) Herb. (Amaryllidaceae)

Detalhes bibliográficos
Autor(a) principal: Oliveira, Marcos Vinícius Lacerda de
Data de Publicação: 2017
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/10/8354
Resumo: Objectives: The main objective of the present work was to carry out a chemical study on alkaloids of the species Hippeastrum reginae, promoting the isolation and characterization of these compounds. Methods: The plant was separated in bulbs and leaves for the extraction with methanol. After this step, the acid-base extraction and then the partition with solvents of different polarities were made to obtain the fractions enriched in alkaloids. The enriched fractions were initially analyzed by gas chromatography coupled to mass spectrometry (GC/MS) and then fractionated by chromatographic techniques such as Sephadex exclusion column, column chromatography and preparative thin layer chromatography. For the isolation of some alkaloids, high performance liquid chromatography (HPLC) and for the identification of the nuclear magnetic resonance (NMR) technique were used. Results: The CG/MS analyze of the extracts evidenced the presence of 11 alkaloids, of which four had no fragmentation pattern compatible with the alkaloid library, and may be unpublished in the literature. Eighteen alkaloids of Amaryllidaceae were isolated, most of them belonging to the homolycorine class. Of these compounds, six new alkaloids of Amaryllidaceae were identified, four of which were fully elucidated (2--methoxy-7-hydroxyhomolycorine, 2--7-dihydroxyhomolycorine, 2-- methoxyhomolycorine and 2-α-hydroxyalbomaculine), while Two (7-hydroxyhomolycorine and N-oxide albomaculine) analyzes were performed for 1H-NMR and high resolution masses. Conclusion: The H. reginae plant had a high alkaloid content and 18 compounds were isolated. Albomaculine and 2--7- dimethoxyhomolycorine alkaloids were the most abundant in GC / MS analysis. Six alkaloids not found in the literature were identified in this work and show a great potential for the discovery of new active compounds.
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spelling Borges, Warley de SouzaOliveira, Marcos Vinícius Lacerda deCunha Neto, ÁlvaroVieira, Paulo Cezar2018-08-01T23:27:54Z2018-08-012018-08-01T23:27:54Z2017-03-20Objectives: The main objective of the present work was to carry out a chemical study on alkaloids of the species Hippeastrum reginae, promoting the isolation and characterization of these compounds. Methods: The plant was separated in bulbs and leaves for the extraction with methanol. After this step, the acid-base extraction and then the partition with solvents of different polarities were made to obtain the fractions enriched in alkaloids. The enriched fractions were initially analyzed by gas chromatography coupled to mass spectrometry (GC/MS) and then fractionated by chromatographic techniques such as Sephadex exclusion column, column chromatography and preparative thin layer chromatography. For the isolation of some alkaloids, high performance liquid chromatography (HPLC) and for the identification of the nuclear magnetic resonance (NMR) technique were used. Results: The CG/MS analyze of the extracts evidenced the presence of 11 alkaloids, of which four had no fragmentation pattern compatible with the alkaloid library, and may be unpublished in the literature. Eighteen alkaloids of Amaryllidaceae were isolated, most of them belonging to the homolycorine class. Of these compounds, six new alkaloids of Amaryllidaceae were identified, four of which were fully elucidated (2--methoxy-7-hydroxyhomolycorine, 2--7-dihydroxyhomolycorine, 2-- methoxyhomolycorine and 2-α-hydroxyalbomaculine), while Two (7-hydroxyhomolycorine and N-oxide albomaculine) analyzes were performed for 1H-NMR and high resolution masses. Conclusion: The H. reginae plant had a high alkaloid content and 18 compounds were isolated. Albomaculine and 2--7- dimethoxyhomolycorine alkaloids were the most abundant in GC / MS analysis. Six alkaloids not found in the literature were identified in this work and show a great potential for the discovery of new active compounds.O presente trabalho teve como principal objetivo realizar o estudo químico em alcaloides da espécie Hippeastrum reginae, promovendo o isolamento e caracterização destes compostos. Métodos: A planta foi separada em bulbos e folhas para a realização da extração com metanol. Após esta etapa foi feita a extração ácido-base e em seguida a partição com solventes de diferentes polaridades para a obtenção das frações enriquecidas em alcaloides. As frações enriquecidas foram inicialmente analisadas por cromatografia gasosa acoplada à espectrometria de massas (CG/EM) e em seguida fracionadas através de técnicas cromatográficas, como coluna de exclusão Sephadex, cromatografia em coluna e cromatografia em camada delgada preparativa. Para o isolamento de alguns alcaloides foi utilizada a cromatografia líquida de alta eficiência (CLAE) e para a identificação a técnica de ressonância magnética nuclear (RMN). Resultados: A análise de CG/EM dos extratos evidenciou a presença de 11 alcaloides, sendo que destes compostos, quatro não apresentaram padrão de fragmentação compatível com a biblioteca de alcaloides do professor Dr. Jaume Bastida, podendo ser inéditos na literatura. Foram isolados 18 alcaloides de Amaryllidaceae, sendo a maioria pertencente à classe das homolicorinas. Destes compostos, foram identificados seis novos alcaloides de Amaryllidaceae, dos quais quatro foram completamente elucidados (2--metoxi-7-hidroxihomolicorina, 2--7-dihidroxihomolicorina, 2--metoxihomolicorina e 2-α-hidroxialbomaculina), enquanto para dois (7-hidroxihomolicorina e albomaculina N-óxido) foram feitas as análises de RMN de 1H e massas de alta resolução. Conclusão: A planta H. reginae apresentou um alto teor de alcaloides, sendo isolados 18 compostos. Os alcaloides albomaculina e 2--7-dimetoxihomolicorina foram os mais abundantes na análise de CG/EM. Seis alcaloides não encontrados na literatura foram identificados neste trabalho e evidenciam um grande potencial para a descoberta de novos compostos ativos.Texthttp://repositorio.ufes.br/handle/10/8354porUniversidade Federal do Espírito SantoMestrado em Ciências FarmacêuticasPrograma de Pós-Graduação em Ciências FarmacêuticasUFESBRCentro de Ciências da SaúdeHomolycorineAlkaloidsLiliaceaeAmaryllidaceaeHippeastrum reginaeHomolicorinaAlcalóidesFarmacêuticosAmarilidáceaFarmácia615Estudo químico em alcaloides de Hippeastrum reginae (L.) Herb. (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:UFESORIGINALtese_9419_DISSERTAÇÃO DE MESTRADO MARCOS_PPGCFar UFES.pdfapplication/pdf7850283http://repositorio.ufes.br/bitstreams/30a9d51a-47ae-4b79-9c64-206eaa05c171/download8ff896271f1e735acb64634a95ccccc6MD5110/83542024-07-16 17:05:52.521oai:repositorio.ufes.br:10/8354http://repositorio.ufes.brRepositório InstitucionalPUBhttp://repositorio.ufes.br/oai/requestopendoar:21082024-10-15T17:57:28.584523Repositório Institucional da Universidade Federal do Espírito Santo (riUfes) - Universidade Federal do Espírito Santo (UFES)false
dc.title.none.fl_str_mv Estudo químico em alcaloides de Hippeastrum reginae (L.) Herb. (Amaryllidaceae)
title Estudo químico em alcaloides de Hippeastrum reginae (L.) Herb. (Amaryllidaceae)
spellingShingle Estudo químico em alcaloides de Hippeastrum reginae (L.) Herb. (Amaryllidaceae)
Oliveira, Marcos Vinícius Lacerda de
Homolycorine
Alkaloids
Liliaceae
Amaryllidaceae
Hippeastrum reginae
Homolicorina
Farmácia
Alcalóides
Farmacêuticos
Amarilidácea
615
title_short Estudo químico em alcaloides de Hippeastrum reginae (L.) Herb. (Amaryllidaceae)
title_full Estudo químico em alcaloides de Hippeastrum reginae (L.) Herb. (Amaryllidaceae)
title_fullStr Estudo químico em alcaloides de Hippeastrum reginae (L.) Herb. (Amaryllidaceae)
title_full_unstemmed Estudo químico em alcaloides de Hippeastrum reginae (L.) Herb. (Amaryllidaceae)
title_sort Estudo químico em alcaloides de Hippeastrum reginae (L.) Herb. (Amaryllidaceae)
author Oliveira, Marcos Vinícius Lacerda de
author_facet Oliveira, Marcos Vinícius Lacerda de
author_role author
dc.contributor.advisor1.fl_str_mv Borges, Warley de Souza
dc.contributor.author.fl_str_mv Oliveira, Marcos Vinícius Lacerda de
dc.contributor.referee1.fl_str_mv Cunha Neto, Álvaro
dc.contributor.referee2.fl_str_mv Vieira, Paulo Cezar
contributor_str_mv Borges, Warley de Souza
Cunha Neto, Álvaro
Vieira, Paulo Cezar
dc.subject.eng.fl_str_mv Homolycorine
Alkaloids
topic Homolycorine
Alkaloids
Liliaceae
Amaryllidaceae
Hippeastrum reginae
Homolicorina
Farmácia
Alcalóides
Farmacêuticos
Amarilidácea
615
dc.subject.por.fl_str_mv Liliaceae
Amaryllidaceae
Hippeastrum reginae
Homolicorina
dc.subject.cnpq.fl_str_mv Farmácia
dc.subject.br-rjbn.none.fl_str_mv Alcalóides
Farmacêuticos
Amarilidácea
dc.subject.udc.none.fl_str_mv 615
description Objectives: The main objective of the present work was to carry out a chemical study on alkaloids of the species Hippeastrum reginae, promoting the isolation and characterization of these compounds. Methods: The plant was separated in bulbs and leaves for the extraction with methanol. After this step, the acid-base extraction and then the partition with solvents of different polarities were made to obtain the fractions enriched in alkaloids. The enriched fractions were initially analyzed by gas chromatography coupled to mass spectrometry (GC/MS) and then fractionated by chromatographic techniques such as Sephadex exclusion column, column chromatography and preparative thin layer chromatography. For the isolation of some alkaloids, high performance liquid chromatography (HPLC) and for the identification of the nuclear magnetic resonance (NMR) technique were used. Results: The CG/MS analyze of the extracts evidenced the presence of 11 alkaloids, of which four had no fragmentation pattern compatible with the alkaloid library, and may be unpublished in the literature. Eighteen alkaloids of Amaryllidaceae were isolated, most of them belonging to the homolycorine class. Of these compounds, six new alkaloids of Amaryllidaceae were identified, four of which were fully elucidated (2--methoxy-7-hydroxyhomolycorine, 2--7-dihydroxyhomolycorine, 2-- methoxyhomolycorine and 2-α-hydroxyalbomaculine), while Two (7-hydroxyhomolycorine and N-oxide albomaculine) analyzes were performed for 1H-NMR and high resolution masses. Conclusion: The H. reginae plant had a high alkaloid content and 18 compounds were isolated. Albomaculine and 2--7- dimethoxyhomolycorine alkaloids were the most abundant in GC / MS analysis. Six alkaloids not found in the literature were identified in this work and show a great potential for the discovery of new active compounds.
publishDate 2017
dc.date.issued.fl_str_mv 2017-03-20
dc.date.accessioned.fl_str_mv 2018-08-01T23:27:54Z
dc.date.available.fl_str_mv 2018-08-01
2018-08-01T23:27:54Z
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dc.type.driver.fl_str_mv info:eu-repo/semantics/masterThesis
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dc.format.none.fl_str_mv Text
dc.publisher.none.fl_str_mv Universidade Federal do Espírito Santo
Mestrado em Ciências Farmacêuticas
dc.publisher.program.fl_str_mv Programa de Pós-Graduação em Ciências Farmacêuticas
dc.publisher.initials.fl_str_mv UFES
dc.publisher.country.fl_str_mv BR
dc.publisher.department.fl_str_mv Centro de Ciências da Saúde
publisher.none.fl_str_mv Universidade Federal do Espírito Santo
Mestrado em Ciências Farmacêuticas
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