Estudo químico e farmacológico de Acnistus arborescens L. Schlecht e Physalis angulata L.

Detalhes bibliográficos
Ano de defesa: 2006
Autor(a) principal: Veras, Maria Leopoldina
Orientador(a): Pessoa, Otília Deusdênia Loiola
Banca de defesa: Não Informado pela instituição
Tipo de documento: Tese
Tipo de acesso: Acesso aberto
Idioma: por
Instituição de defesa: Não Informado pela instituição
Programa de Pós-Graduação: Não Informado pela instituição
Departamento: Não Informado pela instituição
País: Não Informado pela instituição
Área do conhecimento CNPq:
Link de acesso: http://repositorio.ufc.br/handle/riufc/74192
Resumo: The present work describes the results of chemical and pharmacological studies of Physalis angulata and Acnistus arborescens (Solanaceae). The bioguided investigation of the ethanol extract from aerial parts of P. angulata resulted in the isolation and characterization of five withasteroids, which were identified as physalins B, D, E, F and 5a-ethoxi,6(3-hydroxy- 5,6-dihydrophysalin B. Of the ethanol extract from leaves of A. arborescens. The dichloromethane fraction from was responsible for the activity and its chemical investigation resulted in the isolation of nine compounds, including a new ceramide, and five withasteroids characterized as withaphysalin M, N, O, (17S,20R,22R)-5113,6,13:18,20-diepoxy-4/3,18- dihydroxy-1-oxovitan-2,24-dienolide and (17S,20R,22R)-5 [3,613: 18,20-diepoxy-4 p,18- dihydroxy-1 -oxovita-24-enolide. 3:18,20-diepoxy-4(3,18- hydroxy-1-oxovita-24-enolide. From the ethanol extract of the stems, a new ceramide together with the known compounds betulinic acid, docosanoic acid and a mixture of sitosterol and stimasterol, including their respective glucosides were isolated. The structures of all compounds were determined by IR, MS, and 111 and 13C NMR (1D and 2D) analyses. The in vitro cytotoxicity of physalins and withaphysalins was evaluated using a panel of nine tumor cell lines: CEM (lymphocyte leukemia), HL-60 (promyelicytic leukemia), HCT-8 (colon), MCF-7 (breast), B-16 (murine skin), PC-3 (prostate), MDA-MB-231 (breast), MDAMB-435 (breast) and K-562 (erytroleukemia). Except for physalin E and withaphysalin N, all compounds showed considerable citotoxicity. The physalins B and D showed in vivo antitumor activity, on sarcoma 180. In addition, the antimitotic effect of all physalins and withaphysalins was determined through sea urchin eggs assay (Lytechinus variegatus).
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spelling Veras, Maria LeopoldinaPessoa, Otília Deusdênia Loiola2023-09-05T13:55:19Z2023-09-05T13:55:19Z2006VERAS, Maria Leopoldina. Estudo químico e farmacológico de Acnistus arborescens L. Schlecht e Physalis angulata L.. 2006. Tese (doutorado em Química Orgânica) - Universidade Federal do Ceará, Fortaleza, 2006.http://repositorio.ufc.br/handle/riufc/74192The present work describes the results of chemical and pharmacological studies of Physalis angulata and Acnistus arborescens (Solanaceae). The bioguided investigation of the ethanol extract from aerial parts of P. angulata resulted in the isolation and characterization of five withasteroids, which were identified as physalins B, D, E, F and 5a-ethoxi,6(3-hydroxy- 5,6-dihydrophysalin B. Of the ethanol extract from leaves of A. arborescens. The dichloromethane fraction from was responsible for the activity and its chemical investigation resulted in the isolation of nine compounds, including a new ceramide, and five withasteroids characterized as withaphysalin M, N, O, (17S,20R,22R)-5113,6,13:18,20-diepoxy-4/3,18- dihydroxy-1-oxovitan-2,24-dienolide and (17S,20R,22R)-5 [3,613: 18,20-diepoxy-4 p,18- dihydroxy-1 -oxovita-24-enolide. 3:18,20-diepoxy-4(3,18- hydroxy-1-oxovita-24-enolide. From the ethanol extract of the stems, a new ceramide together with the known compounds betulinic acid, docosanoic acid and a mixture of sitosterol and stimasterol, including their respective glucosides were isolated. The structures of all compounds were determined by IR, MS, and 111 and 13C NMR (1D and 2D) analyses. The in vitro cytotoxicity of physalins and withaphysalins was evaluated using a panel of nine tumor cell lines: CEM (lymphocyte leukemia), HL-60 (promyelicytic leukemia), HCT-8 (colon), MCF-7 (breast), B-16 (murine skin), PC-3 (prostate), MDA-MB-231 (breast), MDAMB-435 (breast) and K-562 (erytroleukemia). Except for physalin E and withaphysalin N, all compounds showed considerable citotoxicity. The physalins B and D showed in vivo antitumor activity, on sarcoma 180. In addition, the antimitotic effect of all physalins and withaphysalins was determined through sea urchin eggs assay (Lytechinus variegatus).O presente trabalho descreve o estudo químico e farmacológico de exemplares das espécies Physalis angulata e Acnistus arborescens, ambas pertencentes à família Solanaceae. Das frações ativas, diclorometano e acetato de etila, ambas provenientes do extrato etanólico da parte aérea de P. angulata foram isoladas as fisalinas B, D, E, F e 5a-etóxi-6(3-hidroxi-5,6- diidrofisalina B. Com o objetivo de estabelecer uma possível relação estrutura atividade, alguns derivados foram preparados a partir da fisalina 5a-etóxi-6j3-hidroxi-5,6-diidrofisalina B. O extrato etanólico das folhas de A. arborescens também apresentou elevada citotoxicidade. Desse extrato, a fração diclorometano foi identificada como sendo a responsável pela atividade citotóxica. A prospecção química dessa fração resultou no isolamento de nove compostos, entre os quais, uma nova ceramida e cinco vitasteróides, caracterizados como sendo as vitafisalinas M, N, 0, (17S,20R,22R)-5/3,6/3:18,20-diepóxi- 4/3,18-diidroxi-l-oxovitan-2,24-dienolido e (17S,20R,22R)-5(3,6(3:18,20-diepóxi-4f3,18- diidroxi-l-oxovita-24-enolido. Do extrato etanólico dos talos de A. arborescens, foi também obtido uma nova ceramida, além de compostos conhecidos como o ácido betulínico, o ácido dodecosanóico e as misturas dos fitosteróides sitosterol e estigmasterol, livres e em suas respectivas formas glicosiladas. A elucidação estrutural de todos os compostos isolados neste trabalho envolveu o uso de técnicas espectrométricas como IV, EM e RMN 'H e '3C (1D e 2D), além de comparação com dados da literatura. O potencial citotóxico in vitro de todas as fisalinas e vitafisalinas, foi avaliado utilizando um painel constituído de várias linhagens de células tumorais: CEM (leucemia linfocítica), HL-60 (leucemia mieloblástica aguda), HCT-8 (cólon), MCF-7 (mama), B-16 (pele), PC-3 (próstata), MDA-MB-231 (mama), MDA-MB- 435 (mama) e K-562 (leucemia mielogênica crônica). Exceto a fisalina E e a vitafisalina N, todas as demais fisalinas apresentaram elevada atividade citotóxica. As fisalinas B e D apresentaram atividade antitumoral in vivo, sobre sarcoma 180, transplantado em camundongo Mus musculus Swiss. A atividade antimitótica desses metabólitos foi também avaliada sobre ovos de Lytechinus variegatus (ouriço-do-mar).Estudo químico e farmacológico de Acnistus arborescens L. Schlecht e Physalis angulata L.info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/doctoralThesisPhysalis angulataAcnistus arborescensFisalinasVitafisalinasVitasteróidesCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICAinfo:eu-repo/semantics/openAccessporreponame:Repositório Institucional da Universidade Federal do Ceará (UFC)instname:Universidade Federal do Ceará (UFC)instacron:UFChttp://lattes.cnpq.br/6718407996891614http://lattes.cnpq.br/03506187005128642006ORIGINAL2006_tese_mlveras.pdf2006_tese_mlveras.pdfapplication/pdf263914611http://repositorio.ufc.br/bitstream/riufc/74192/1/2006_tese_mlveras.pdf7f0d5e4f8bec90f45da64a332c5998e8MD51LICENSElicense.txtlicense.txttext/plain; charset=utf-81748http://repositorio.ufc.br/bitstream/riufc/74192/2/license.txt8a4605be74aa9ea9d79846c1fba20a33MD52riufc/741922023-09-05 10:55:20.183oai:repositorio.ufc.br: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Repositório InstitucionalPUBhttp://www.repositorio.ufc.br/ri-oai/requestbu@ufc.br || repositorio@ufc.bropendoar:2023-09-05T13:55:20Repositório Institucional da Universidade Federal do Ceará (UFC) - Universidade Federal do Ceará (UFC)false
dc.title.pt_BR.fl_str_mv Estudo químico e farmacológico de Acnistus arborescens L. Schlecht e Physalis angulata L.
title Estudo químico e farmacológico de Acnistus arborescens L. Schlecht e Physalis angulata L.
spellingShingle Estudo químico e farmacológico de Acnistus arborescens L. Schlecht e Physalis angulata L.
Veras, Maria Leopoldina
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
Physalis angulata
Acnistus arborescens
Fisalinas
Vitafisalinas
Vitasteróides
title_short Estudo químico e farmacológico de Acnistus arborescens L. Schlecht e Physalis angulata L.
title_full Estudo químico e farmacológico de Acnistus arborescens L. Schlecht e Physalis angulata L.
title_fullStr Estudo químico e farmacológico de Acnistus arborescens L. Schlecht e Physalis angulata L.
title_full_unstemmed Estudo químico e farmacológico de Acnistus arborescens L. Schlecht e Physalis angulata L.
title_sort Estudo químico e farmacológico de Acnistus arborescens L. Schlecht e Physalis angulata L.
author Veras, Maria Leopoldina
author_facet Veras, Maria Leopoldina
author_role author
dc.contributor.author.fl_str_mv Veras, Maria Leopoldina
dc.contributor.advisor1.fl_str_mv Pessoa, Otília Deusdênia Loiola
contributor_str_mv Pessoa, Otília Deusdênia Loiola
dc.subject.cnpq.fl_str_mv CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
topic CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
Physalis angulata
Acnistus arborescens
Fisalinas
Vitafisalinas
Vitasteróides
dc.subject.ptbr.pt_BR.fl_str_mv Physalis angulata
Acnistus arborescens
Fisalinas
Vitafisalinas
Vitasteróides
description The present work describes the results of chemical and pharmacological studies of Physalis angulata and Acnistus arborescens (Solanaceae). The bioguided investigation of the ethanol extract from aerial parts of P. angulata resulted in the isolation and characterization of five withasteroids, which were identified as physalins B, D, E, F and 5a-ethoxi,6(3-hydroxy- 5,6-dihydrophysalin B. Of the ethanol extract from leaves of A. arborescens. The dichloromethane fraction from was responsible for the activity and its chemical investigation resulted in the isolation of nine compounds, including a new ceramide, and five withasteroids characterized as withaphysalin M, N, O, (17S,20R,22R)-5113,6,13:18,20-diepoxy-4/3,18- dihydroxy-1-oxovitan-2,24-dienolide and (17S,20R,22R)-5 [3,613: 18,20-diepoxy-4 p,18- dihydroxy-1 -oxovita-24-enolide. 3:18,20-diepoxy-4(3,18- hydroxy-1-oxovita-24-enolide. From the ethanol extract of the stems, a new ceramide together with the known compounds betulinic acid, docosanoic acid and a mixture of sitosterol and stimasterol, including their respective glucosides were isolated. The structures of all compounds were determined by IR, MS, and 111 and 13C NMR (1D and 2D) analyses. The in vitro cytotoxicity of physalins and withaphysalins was evaluated using a panel of nine tumor cell lines: CEM (lymphocyte leukemia), HL-60 (promyelicytic leukemia), HCT-8 (colon), MCF-7 (breast), B-16 (murine skin), PC-3 (prostate), MDA-MB-231 (breast), MDAMB-435 (breast) and K-562 (erytroleukemia). Except for physalin E and withaphysalin N, all compounds showed considerable citotoxicity. The physalins B and D showed in vivo antitumor activity, on sarcoma 180. In addition, the antimitotic effect of all physalins and withaphysalins was determined through sea urchin eggs assay (Lytechinus variegatus).
publishDate 2006
dc.date.issued.fl_str_mv 2006
dc.date.accessioned.fl_str_mv 2023-09-05T13:55:19Z
dc.date.available.fl_str_mv 2023-09-05T13:55:19Z
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
dc.type.driver.fl_str_mv info:eu-repo/semantics/doctoralThesis
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dc.identifier.citation.fl_str_mv VERAS, Maria Leopoldina. Estudo químico e farmacológico de Acnistus arborescens L. Schlecht e Physalis angulata L.. 2006. Tese (doutorado em Química Orgânica) - Universidade Federal do Ceará, Fortaleza, 2006.
dc.identifier.uri.fl_str_mv http://repositorio.ufc.br/handle/riufc/74192
identifier_str_mv VERAS, Maria Leopoldina. Estudo químico e farmacológico de Acnistus arborescens L. Schlecht e Physalis angulata L.. 2006. Tese (doutorado em Química Orgânica) - Universidade Federal do Ceará, Fortaleza, 2006.
url http://repositorio.ufc.br/handle/riufc/74192
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