Estudo químico e farmacológico de Acnistus arborescens L. Schlecht e Physalis angulata L.
| Ano de defesa: | 2006 |
|---|---|
| Autor(a) principal: | |
| Orientador(a): | |
| Banca de defesa: | |
| 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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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). |
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2006 |
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2006 |
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2023-09-05T13:55:19Z |
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2023-09-05T13:55:19Z |
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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. |
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http://repositorio.ufc.br/handle/riufc/74192 |
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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. |
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