Estudo fitoquímico de Hippeastrum diniz-cruziae Dutilh & Semir e Hippeastrum glaucescens (Mart.) Herb. (Amaryllidaceae)

Detalhes bibliográficos
Autor(a) principal: Santos, Vanessa Dias dos
Data de Publicação: 2019
Tipo de documento: Tese
Idioma: por
Título da fonte: Repositório Institucional da Universidade Federal do Espírito Santo (riUfes)
Texto Completo: http://repositorio.ufes.br/handle/10/13412
Resumo: The interest in the study of the Amaryllidaceae family is related by yours relevant chemical and biological potential that has presented over the years. The objective of this work is the isolation and characterization of alkaloids present in two Brazilian species, Hippeastrum diniz-cruziae (leaves, bulbs and roots) and Hippeastrum glaucescens (bulbs). Initially, an acid-base extraction was performed in the methanolic extracts and liquid-liquid partition of the vegetal parts, obtaining the acid AcOEt and alkaloid enriched fractions. These extracts were analyzed by GC-MS and indicated to Hippeastrum diniz-cruziae 39 known alkaloids and 24 unidentified compounds. For Hippeastrum glaucescens 12 known alkaloids and 9 unknown compounds were identified. These extracts were subjected to various chromatographic separation techniques in order to isolate and purify these compounds. As a result, 5 Hippeastrum diniz-cruziae alkaloids were isolated: cruzinine (I), 7-deoxy-narciclasine (II), licoryne (III), pseudolycorine (IV) and ungiminorine (V), with cruzinine being an unpublished alkaloid of the type homolicorin, elucidated by GC-MS, one and two-dimensional NMR, Circular Dichroism and, mainly, X-ray Crystallography. This compound presented a unique characteristic within Amaryllidaceae alkaloids, evidenced by the stereochemistry of positions H-1 and H-10b. Fractions of Hippeastrum glaucescens resulted in 20 alkaloids: 2α-7-dimethoxyhomolicorine N-oxide (VI), 7-Methoxy-O-methylillorenine N oxide (VII), Candimine N-oxide (VIII), N-oxide albamaculine (IX), 2α methoxyhomolycorine (XX), 2α-hydroxyhomolycorine (XXI), albomaculine (XXII), 2α hydroxyalbomaculine (XIII), 2α, 7-dimethoxyhomolycorine (XIV), 7-Methoxy-O methyllicorine (XV), candimine (XVI), hyppeastrine (XVII), haemantidine (XVIII), 6 epihaemantidine (XIX), 11-hydroxyvitatine (XX), tazetine (XXI), pretazetine (XXII), 3 epimachrine (XXIII), trisfaeridine (XXIV) and ismine (XXV), compounds (XI), (XVIII), (XIX) and (XXII) being obtained in three mixtures. The compounds (VI), (VII) and (VIII) were isolated for the first time in this study, being identified by 1H NMR and high resolution masses. for the compound (VII) also high resolution masses. Previous studies of Hippeastrum glaucescens have indicated relevant alkaloid and biological potential, with potential inhibitory enzyme acetylcholinesterase. For Hippeastrum diniz-cruziae this is the first phytochemical study performed, and its previous report has reported its high moebicide power and low toxicity. In this sense, this evidence 26 gives great relevance in the continuation of the respective chemical and biological studies with the respective species.
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spelling Borges, Warley de Souzahttps://orcid.org/0000000344751028http://lattes.cnpq.br/9742402285970429Santos, Vanessa Dias doshttps://orcid.org/http://lattes.cnpq.br/3852118255704584Neto, Alvaro Cunhahttps://orcid.org/http://lattes.cnpq.br/7448379486432052Franca, Hildegardo Seiberthttps://orcid.org/http://lattes.cnpq.br/1284874997224988Kuster, Ricardo Machadohttps://orcid.org/0000000289615348http://lattes.cnpq.br/41498149067863662024-05-29T22:11:10Z2024-05-29T22:11:10Z2019-08-28The interest in the study of the Amaryllidaceae family is related by yours relevant chemical and biological potential that has presented over the years. The objective of this work is the isolation and characterization of alkaloids present in two Brazilian species, Hippeastrum diniz-cruziae (leaves, bulbs and roots) and Hippeastrum glaucescens (bulbs). Initially, an acid-base extraction was performed in the methanolic extracts and liquid-liquid partition of the vegetal parts, obtaining the acid AcOEt and alkaloid enriched fractions. These extracts were analyzed by GC-MS and indicated to Hippeastrum diniz-cruziae 39 known alkaloids and 24 unidentified compounds. For Hippeastrum glaucescens 12 known alkaloids and 9 unknown compounds were identified. These extracts were subjected to various chromatographic separation techniques in order to isolate and purify these compounds. As a result, 5 Hippeastrum diniz-cruziae alkaloids were isolated: cruzinine (I), 7-deoxy-narciclasine (II), licoryne (III), pseudolycorine (IV) and ungiminorine (V), with cruzinine being an unpublished alkaloid of the type homolicorin, elucidated by GC-MS, one and two-dimensional NMR, Circular Dichroism and, mainly, X-ray Crystallography. This compound presented a unique characteristic within Amaryllidaceae alkaloids, evidenced by the stereochemistry of positions H-1 and H-10b. Fractions of Hippeastrum glaucescens resulted in 20 alkaloids: 2α-7-dimethoxyhomolicorine N-oxide (VI), 7-Methoxy-O-methylillorenine N oxide (VII), Candimine N-oxide (VIII), N-oxide albamaculine (IX), 2α methoxyhomolycorine (XX), 2α-hydroxyhomolycorine (XXI), albomaculine (XXII), 2α hydroxyalbomaculine (XIII), 2α, 7-dimethoxyhomolycorine (XIV), 7-Methoxy-O methyllicorine (XV), candimine (XVI), hyppeastrine (XVII), haemantidine (XVIII), 6 epihaemantidine (XIX), 11-hydroxyvitatine (XX), tazetine (XXI), pretazetine (XXII), 3 epimachrine (XXIII), trisfaeridine (XXIV) and ismine (XXV), compounds (XI), (XVIII), (XIX) and (XXII) being obtained in three mixtures. The compounds (VI), (VII) and (VIII) were isolated for the first time in this study, being identified by 1H NMR and high resolution masses. for the compound (VII) also high resolution masses. Previous studies of Hippeastrum glaucescens have indicated relevant alkaloid and biological potential, with potential inhibitory enzyme acetylcholinesterase. For Hippeastrum diniz-cruziae this is the first phytochemical study performed, and its previous report has reported its high moebicide power and low toxicity. In this sense, this evidence 26 gives great relevance in the continuation of the respective chemical and biological studies with the respective species.O interesse pelo estudo da família Amaryllidaceae está relacionado ao seu relevante potencial químico e biológico que tem apresentado ao longo dos anos. O trabalho em questão, tem por objetivo o isolamento e a caracterização dos alcaloides presentes em duas espécies brasileiras, o Hippeastrum diniz-cruziae (folhas, bulbos e raízes) e o Hippeastrum glaucescens (bulbos). Inicialmente foi realizada uma extração ácido-base nos extratos metanólicos e partição líquido-líquido das partes vegetais, obtendo-se as frações de AcOEt ácido e frações enriquecidos em alcaloides. Esses extratos foram analisados por CG-EM e detectaram para o Hippeastrum diniz-cruziae 39 alcaloides conhecidos e 24 compostos não identificados pela biblioteca de alcaloides, para o Hippeastrum glaucescens foram detectados 12 alcaloides conhecidos e 9 compostos desconhecidos. Esses extratos obtidos foram submetidos a variadas técnicas cromatográficas de separação, a fim de isolar e purificar os mesmos. Como resultado, foram isolados 5 alcaloides de Hippeastrum diniz-cruziae: cruzinina (I), 7-deoxi-narciclasina (II), licorina (III), pseudolicorina (IV) e ungiminorina (V), sendo a cruzinina um alcaloide inédito do tipo homolicorina, elucidado por meio de CG-EM, RMN uni e bidimensional, Dicroísmo Circular e, principalmente, Cristalografia de Raios-X. Este composto apresentou uma característica única dentro dos alcaloides de Amaryllidaceae, evidenciada pela estereoquímica das posições H-1 e H-10b. Os fracionamentos do Hippeastrum glaucescens levaram a obtenção de 20 alcaloides: 2α-7-dimetóxihomolicorina N óxido (VI), 7-Metoxi-O-metillicorenina N-óxido (VII), Candimina N-óxido (VIII), albomaculina N-óxido (IX), 2α-metoxihomolicorina (XX), 2α-hidroxihomolicorina (XXI), albomaculina (XXII), 2α-hidroxialbomaculina (XIII), 2α,7-dimetóxihomolicorina (XIV), 7-Metoxi-O-metillicorenina (XV), candimina (XVI), hippeastrina (XVII), haemantidina (XVIII), 6-epihaemantidina (XIX), 11-hidroxivitatina (XX), tazetina (XXI), pretazetina (XXII), 3-epimacronina (XXIII), trisfaeridina (XXIV) e ismina (XXV), sendo os compostos (XI), (XVIII), (XIX) e (XXII) obtidos em três misturas. Os compostos (VI), (VII) e (VIII) foram isolados pela primeira vez nesse trabalho, sendo identificados por RMN de 1H e massas de alta resolução, sendo necessário para a sua completa elucidação estrutural as demais análises de RMN e/ou massas de alta resolução. Estudos anteriores do Hippeastrum glaucescens indicaram relevante potencial alcaloídico e biológico, com potencial inibitório da enzima 24 acetilcolinesterase. Para o Hippeastrum diniz-cruziae este é o primeiro estudo fitoquímico realizado. Neste sentido, estas evidências conferem grande relevância na continuação dos respectivos estudos químicos e biológicos com ambas as espécies.Fundação de Amparo à Pesquisa do Espírito Santo (FAPES)Fundação Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES)Texthttp://repositorio.ufes.br/handle/10/13412porUniversidade Federal do Espírito SantoDoutorado em QuímicaPrograma de Pós-Graduação em QuímicaUFESBRCentro de Ciências Exatassubject.br-rjbnQuímicaAmaryllidaceaeHippeastrum diniz cruziaeHippeastrum glaucescens;AlcaloidesRMNCG-EMNMRCG-MSAlkaloidsEstudo fitoquímico de Hippeastrum diniz-cruziae Dutilh & Semir e Hippeastrum glaucescens (Mart.) Herb. (Amaryllidaceae)Phytochemical study of Hippeastrum diniz-cruziae Dutilh & Semir and Hippeastrum glaucescens (Mart.) Herb. (Amaryllidaceae)info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/doctoralThesisinfo:eu-repo/semantics/openAccessreponame:Repositório Institucional da Universidade Federal do Espírito Santo (riUfes)instname:Universidade Federal do Espírito Santo (UFES)instacron:UFESORIGINALVanessaDiasdosSantos-2019-Tese.pdfapplication/pdf9387197http://repositorio.ufes.br/bitstreams/e138ec83-5245-4e6c-82aa-a68894a4b3ff/downloadcb6493d1be683d3133eaff301823bb93MD5110/134122024-08-05 20:15:36.228oai:repositorio.ufes.br:10/13412http://repositorio.ufes.brRepositório InstitucionalPUBhttp://repositorio.ufes.br/oai/requestopendoar:21082024-10-15T17:59:30.571498Repositório Institucional da Universidade Federal do Espírito Santo (riUfes) - Universidade Federal do Espírito Santo (UFES)false
dc.title.none.fl_str_mv Estudo fitoquímico de Hippeastrum diniz-cruziae Dutilh & Semir e Hippeastrum glaucescens (Mart.) Herb. (Amaryllidaceae)
dc.title.alternative.none.fl_str_mv Phytochemical study of Hippeastrum diniz-cruziae Dutilh & Semir and Hippeastrum glaucescens (Mart.) Herb. (Amaryllidaceae)
title Estudo fitoquímico de Hippeastrum diniz-cruziae Dutilh & Semir e Hippeastrum glaucescens (Mart.) Herb. (Amaryllidaceae)
spellingShingle Estudo fitoquímico de Hippeastrum diniz-cruziae Dutilh & Semir e Hippeastrum glaucescens (Mart.) Herb. (Amaryllidaceae)
Santos, Vanessa Dias dos
Química
Amaryllidaceae
Hippeastrum diniz cruziae
Hippeastrum glaucescens;
Alcaloides
RMN
CG-EM
NMR
CG-MS
Alkaloids
subject.br-rjbn
title_short Estudo fitoquímico de Hippeastrum diniz-cruziae Dutilh & Semir e Hippeastrum glaucescens (Mart.) Herb. (Amaryllidaceae)
title_full Estudo fitoquímico de Hippeastrum diniz-cruziae Dutilh & Semir e Hippeastrum glaucescens (Mart.) Herb. (Amaryllidaceae)
title_fullStr Estudo fitoquímico de Hippeastrum diniz-cruziae Dutilh & Semir e Hippeastrum glaucescens (Mart.) Herb. (Amaryllidaceae)
title_full_unstemmed Estudo fitoquímico de Hippeastrum diniz-cruziae Dutilh & Semir e Hippeastrum glaucescens (Mart.) Herb. (Amaryllidaceae)
title_sort Estudo fitoquímico de Hippeastrum diniz-cruziae Dutilh & Semir e Hippeastrum glaucescens (Mart.) Herb. (Amaryllidaceae)
author Santos, Vanessa Dias dos
author_facet Santos, Vanessa Dias dos
author_role author
dc.contributor.authorID.none.fl_str_mv https://orcid.org/
dc.contributor.authorLattes.none.fl_str_mv http://lattes.cnpq.br/3852118255704584
dc.contributor.advisor1.fl_str_mv Borges, Warley de Souza
dc.contributor.advisor1ID.fl_str_mv https://orcid.org/0000000344751028
dc.contributor.advisor1Lattes.fl_str_mv http://lattes.cnpq.br/9742402285970429
dc.contributor.author.fl_str_mv Santos, Vanessa Dias dos
dc.contributor.referee1.fl_str_mv Neto, Alvaro Cunha
dc.contributor.referee1ID.fl_str_mv https://orcid.org/
dc.contributor.referee1Lattes.fl_str_mv http://lattes.cnpq.br/7448379486432052
dc.contributor.referee2.fl_str_mv Franca, Hildegardo Seibert
dc.contributor.referee2ID.fl_str_mv https://orcid.org/
dc.contributor.referee2Lattes.fl_str_mv http://lattes.cnpq.br/1284874997224988
dc.contributor.referee3.fl_str_mv Kuster, Ricardo Machado
dc.contributor.referee3ID.fl_str_mv https://orcid.org/0000000289615348
dc.contributor.referee3Lattes.fl_str_mv http://lattes.cnpq.br/4149814906786366
contributor_str_mv Borges, Warley de Souza
Neto, Alvaro Cunha
Franca, Hildegardo Seibert
Kuster, Ricardo Machado
dc.subject.cnpq.fl_str_mv Química
topic Química
Amaryllidaceae
Hippeastrum diniz cruziae
Hippeastrum glaucescens;
Alcaloides
RMN
CG-EM
NMR
CG-MS
Alkaloids
subject.br-rjbn
dc.subject.por.fl_str_mv Amaryllidaceae
Hippeastrum diniz cruziae
Hippeastrum glaucescens;
Alcaloides
RMN
CG-EM
NMR
CG-MS
Alkaloids
dc.subject.br-rjbn.none.fl_str_mv subject.br-rjbn
description The interest in the study of the Amaryllidaceae family is related by yours relevant chemical and biological potential that has presented over the years. The objective of this work is the isolation and characterization of alkaloids present in two Brazilian species, Hippeastrum diniz-cruziae (leaves, bulbs and roots) and Hippeastrum glaucescens (bulbs). Initially, an acid-base extraction was performed in the methanolic extracts and liquid-liquid partition of the vegetal parts, obtaining the acid AcOEt and alkaloid enriched fractions. These extracts were analyzed by GC-MS and indicated to Hippeastrum diniz-cruziae 39 known alkaloids and 24 unidentified compounds. For Hippeastrum glaucescens 12 known alkaloids and 9 unknown compounds were identified. These extracts were subjected to various chromatographic separation techniques in order to isolate and purify these compounds. As a result, 5 Hippeastrum diniz-cruziae alkaloids were isolated: cruzinine (I), 7-deoxy-narciclasine (II), licoryne (III), pseudolycorine (IV) and ungiminorine (V), with cruzinine being an unpublished alkaloid of the type homolicorin, elucidated by GC-MS, one and two-dimensional NMR, Circular Dichroism and, mainly, X-ray Crystallography. This compound presented a unique characteristic within Amaryllidaceae alkaloids, evidenced by the stereochemistry of positions H-1 and H-10b. Fractions of Hippeastrum glaucescens resulted in 20 alkaloids: 2α-7-dimethoxyhomolicorine N-oxide (VI), 7-Methoxy-O-methylillorenine N oxide (VII), Candimine N-oxide (VIII), N-oxide albamaculine (IX), 2α methoxyhomolycorine (XX), 2α-hydroxyhomolycorine (XXI), albomaculine (XXII), 2α hydroxyalbomaculine (XIII), 2α, 7-dimethoxyhomolycorine (XIV), 7-Methoxy-O methyllicorine (XV), candimine (XVI), hyppeastrine (XVII), haemantidine (XVIII), 6 epihaemantidine (XIX), 11-hydroxyvitatine (XX), tazetine (XXI), pretazetine (XXII), 3 epimachrine (XXIII), trisfaeridine (XXIV) and ismine (XXV), compounds (XI), (XVIII), (XIX) and (XXII) being obtained in three mixtures. The compounds (VI), (VII) and (VIII) were isolated for the first time in this study, being identified by 1H NMR and high resolution masses. for the compound (VII) also high resolution masses. Previous studies of Hippeastrum glaucescens have indicated relevant alkaloid and biological potential, with potential inhibitory enzyme acetylcholinesterase. For Hippeastrum diniz-cruziae this is the first phytochemical study performed, and its previous report has reported its high moebicide power and low toxicity. In this sense, this evidence 26 gives great relevance in the continuation of the respective chemical and biological studies with the respective species.
publishDate 2019
dc.date.issued.fl_str_mv 2019-08-28
dc.date.accessioned.fl_str_mv 2024-05-29T22:11:10Z
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dc.publisher.none.fl_str_mv Universidade Federal do Espírito Santo
Doutorado em Química
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dc.publisher.country.fl_str_mv BR
dc.publisher.department.fl_str_mv Centro de Ciências Exatas
publisher.none.fl_str_mv Universidade Federal do Espírito Santo
Doutorado em Química
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