Estudo fitoquímico de Conchocarpus marginatus (Rutaceae), e avaliação do potencial biológico dos compostos isolados
Autor(a) principal: | |
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Data de Publicação: | 2013 |
Tipo de documento: | Dissertação |
Idioma: | por |
Título da fonte: | Repositório Institucional da UFSCAR |
Texto Completo: | https://repositorio.ufscar.br/handle/ufscar/6561 |
Resumo: | The specie Conchocarpus marginatus is native from Espírito Santo. This plant, that was recently reclassified by PIRANI e KALLUNKI, does not show chemical or biological data in literature yet. In this way, the phytochemical study of Co. marginatus described in this work, aim to contributed to chemosystematic of Rutaceae family, and a better classification of this genus in the family. The study allowed the isolation and identification of 12 substances, and were found mainly alkaloids derived from antranilic acid. They are: 2-phenyl-1- methyl-quinolin-4-one (11), 2-phenyl-1-methyl-7-methoxy-quinolin-4-one (12), 1-hydroxy-3-methoxy-N-metilacridone (6), Arborinine (7), Methyl-arborinine (8), 1-hydroxy-3,6-dimethoxy-N-metilacridone (10), 1,2,3,6-tetramethoxyacridone (9), 1,2,3,6-tetramethoxy-N-metilacridone (4) e 1-hydroxy-2,3,6- trimethoxy-N-metilacridone (5). The last four substances are new structures. Two different biological assays were performed with some isolated compounds. Assays in vitro of chlorophyll inhibition were performed in chloroplasts isolated from spinach leaves, aiming to found models to new photosynthesis inhibitor herbicides, by study of Chl a fluorescence. Substances isolated from Co. marginatus analysed in this assay were active, and the substance 9 was the most active in Chl a fluorescence measures. This result indicates that this molecule could damage the OEC complex and one of his action site is located in FSII, binding to Qa environment. In cytotoxic assays, the substance 6 is the more promising molecule against cancerígenas MCF-7 (breast adenocarcinoma), NCI-460 (non-small cell lung cancer) and A375-C5 (melanoma) cancer cells, showing respectively GJ50 values of 25, 20 e 22 μM. |
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Bellete, Barbara SayuriSilva, Maria Fátima das Graças Fernandes dahttp://lattes.cnpq.br/0457632122660653http://lattes.cnpq.br/58936339987015971534d8de-7711-4c54-aa21-d3f31cc17f372016-06-02T20:36:46Z2013-09-052016-06-02T20:36:46Z2013-03-27BELLETE, Barbara Sayuri. Phytochemical study of Conchocarpus marginatus (RUTACEAE), and evaluation of biological potential from isolated compounds. 2013. 204 f. Dissertação (Mestrado em Ciências Exatas e da Terra) - Universidade Federal de São Carlos, São Carlos, 2013.https://repositorio.ufscar.br/handle/ufscar/6561The specie Conchocarpus marginatus is native from Espírito Santo. This plant, that was recently reclassified by PIRANI e KALLUNKI, does not show chemical or biological data in literature yet. In this way, the phytochemical study of Co. marginatus described in this work, aim to contributed to chemosystematic of Rutaceae family, and a better classification of this genus in the family. The study allowed the isolation and identification of 12 substances, and were found mainly alkaloids derived from antranilic acid. They are: 2-phenyl-1- methyl-quinolin-4-one (11), 2-phenyl-1-methyl-7-methoxy-quinolin-4-one (12), 1-hydroxy-3-methoxy-N-metilacridone (6), Arborinine (7), Methyl-arborinine (8), 1-hydroxy-3,6-dimethoxy-N-metilacridone (10), 1,2,3,6-tetramethoxyacridone (9), 1,2,3,6-tetramethoxy-N-metilacridone (4) e 1-hydroxy-2,3,6- trimethoxy-N-metilacridone (5). The last four substances are new structures. Two different biological assays were performed with some isolated compounds. Assays in vitro of chlorophyll inhibition were performed in chloroplasts isolated from spinach leaves, aiming to found models to new photosynthesis inhibitor herbicides, by study of Chl a fluorescence. Substances isolated from Co. marginatus analysed in this assay were active, and the substance 9 was the most active in Chl a fluorescence measures. This result indicates that this molecule could damage the OEC complex and one of his action site is located in FSII, binding to Qa environment. In cytotoxic assays, the substance 6 is the more promising molecule against cancerígenas MCF-7 (breast adenocarcinoma), NCI-460 (non-small cell lung cancer) and A375-C5 (melanoma) cancer cells, showing respectively GJ50 values of 25, 20 e 22 μM.A espécie Conchocarpus marginatus é nativa do Espírito Santo. Esta planta, que foi reclassificada em 1998 por PIRANI e KALLUNKI, ainda não apresenta dados químicos ou biológicos na literatura. Desta forma, o estudo fitoquímico de Conchocarpus marginatus descrito neste trabalho, visa contribuir com a quimiossistemática da família Rutaceae e também com a melhor classificação do gênero dentro da mesma. O estudo desta espécie levou ao isolamento e identificação de 12 substâncias, onde foram encontrados principalmente alcalóides derivados do ácido antranílico, sendo estes o 2-fenil-1-metil-quinolin- 4-ona (11), 2-fenil-1-metil-7-metoxi-quinolin-4-ona (12), 1-hidroxi-3-metoxi-Nmetilacridona (6), Arborinina (7), Metil-arborinina (8), 1-hidroxi-3,6-dimetoxi- N-metilacridona (10), 1,2,3,6-tetrametoxi-acridona (9), 1,2,3,6-tetrametoxi-Nmetilacridona (4) e 1-hidroxi-2,3,6-trimetoxi-N-metilacridona (5). Destes, os quatro últimos alcalóides acridônicos citados são estruturas novas. Dois diferentes ensaios biológicos foram realizados com alguns dos compostos isolados. Com o objetivo de se encontrar modelos para novos herbicidas inibidores da fotossíntese, foram realizados ensaios in vitro de inibição da fotossíntese, em cloroplastos isolados das folhas de espinafre, através do estudo de fluorescência da Clorofila a (Chl a). As substâncias isoladas de Conchocarpus marginatus testadas frente a este ensaio se mostraram todas ativas, sendo a substância 9 a que se apresentou potencialmente mais ativa nas medidas de fluorescência Chl a. Esse resultado indica que esta causaria dano ao complexo OEC e um de seus sítios de ação está localizado sobre o FSII, prendendo-se ao ambiente de QA. Nos ensaios citotóxicos, a substância 6 se apresentou como a mais promissora contra as células cancerígenas MCF-7 (adenocarcinoma da mama), NCI-460 (câncer de pulmão) e A375-C5 (cancro de melanoma), apresentando valores de GI50 de 25, 20 e 22 μM, respectivamente.Financiadora de Estudos e Projetosapplication/pdfporUniversidade Federal de São CarlosPrograma de Pós-Graduação em Química - PPGQUFSCarBRQuímica orgânicaConchocarpus marginatusAlcalóides acridônicosFitoquímicaCIENCIAS EXATAS E DA TERRA::QUIMICAEstudo fitoquímico de Conchocarpus marginatus (Rutaceae), e avaliação do potencial biológico dos compostos isoladosPhytochemical study of Conchocarpus marginatus (RUTACEAE), and evaluation of biological potential from isolated compoundsinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesis-1-124b0ac94-885a-4e7b-b93a-7cad21b9592einfo:eu-repo/semantics/openAccessreponame:Repositório Institucional da UFSCARinstname:Universidade Federal de São Carlos (UFSCAR)instacron:UFSCARORIGINAL5349.pdfapplication/pdf6996225https://repositorio.ufscar.br/bitstream/ufscar/6561/1/5349.pdf58705c45ef0e50d30f35cd6392ce7c15MD51TEXT5349.pdf.txt5349.pdf.txtExtracted texttext/plain0https://repositorio.ufscar.br/bitstream/ufscar/6561/4/5349.pdf.txtd41d8cd98f00b204e9800998ecf8427eMD54THUMBNAIL5349.pdf.jpg5349.pdf.jpgIM Thumbnailimage/jpeg9730https://repositorio.ufscar.br/bitstream/ufscar/6561/5/5349.pdf.jpged5cc4df216504dba5ef2f68546fb4a6MD55ufscar/65612023-09-18 18:31:52.232oai:repositorio.ufscar.br:ufscar/6561Repositório InstitucionalPUBhttps://repositorio.ufscar.br/oai/requestopendoar:43222023-09-18T18:31:52Repositório Institucional da UFSCAR - Universidade Federal de São Carlos (UFSCAR)false |
dc.title.por.fl_str_mv |
Estudo fitoquímico de Conchocarpus marginatus (Rutaceae), e avaliação do potencial biológico dos compostos isolados |
dc.title.alternative.eng.fl_str_mv |
Phytochemical study of Conchocarpus marginatus (RUTACEAE), and evaluation of biological potential from isolated compounds |
title |
Estudo fitoquímico de Conchocarpus marginatus (Rutaceae), e avaliação do potencial biológico dos compostos isolados |
spellingShingle |
Estudo fitoquímico de Conchocarpus marginatus (Rutaceae), e avaliação do potencial biológico dos compostos isolados Bellete, Barbara Sayuri Química orgânica Conchocarpus marginatus Alcalóides acridônicos Fitoquímica CIENCIAS EXATAS E DA TERRA::QUIMICA |
title_short |
Estudo fitoquímico de Conchocarpus marginatus (Rutaceae), e avaliação do potencial biológico dos compostos isolados |
title_full |
Estudo fitoquímico de Conchocarpus marginatus (Rutaceae), e avaliação do potencial biológico dos compostos isolados |
title_fullStr |
Estudo fitoquímico de Conchocarpus marginatus (Rutaceae), e avaliação do potencial biológico dos compostos isolados |
title_full_unstemmed |
Estudo fitoquímico de Conchocarpus marginatus (Rutaceae), e avaliação do potencial biológico dos compostos isolados |
title_sort |
Estudo fitoquímico de Conchocarpus marginatus (Rutaceae), e avaliação do potencial biológico dos compostos isolados |
author |
Bellete, Barbara Sayuri |
author_facet |
Bellete, Barbara Sayuri |
author_role |
author |
dc.contributor.authorlattes.por.fl_str_mv |
http://lattes.cnpq.br/5893633998701597 |
dc.contributor.author.fl_str_mv |
Bellete, Barbara Sayuri |
dc.contributor.advisor1.fl_str_mv |
Silva, Maria Fátima das Graças Fernandes da |
dc.contributor.advisor1Lattes.fl_str_mv |
http://lattes.cnpq.br/0457632122660653 |
dc.contributor.authorID.fl_str_mv |
1534d8de-7711-4c54-aa21-d3f31cc17f37 |
contributor_str_mv |
Silva, Maria Fátima das Graças Fernandes da |
dc.subject.por.fl_str_mv |
Química orgânica Conchocarpus marginatus Alcalóides acridônicos Fitoquímica |
topic |
Química orgânica Conchocarpus marginatus Alcalóides acridônicos Fitoquímica CIENCIAS EXATAS E DA TERRA::QUIMICA |
dc.subject.cnpq.fl_str_mv |
CIENCIAS EXATAS E DA TERRA::QUIMICA |
description |
The specie Conchocarpus marginatus is native from Espírito Santo. This plant, that was recently reclassified by PIRANI e KALLUNKI, does not show chemical or biological data in literature yet. In this way, the phytochemical study of Co. marginatus described in this work, aim to contributed to chemosystematic of Rutaceae family, and a better classification of this genus in the family. The study allowed the isolation and identification of 12 substances, and were found mainly alkaloids derived from antranilic acid. They are: 2-phenyl-1- methyl-quinolin-4-one (11), 2-phenyl-1-methyl-7-methoxy-quinolin-4-one (12), 1-hydroxy-3-methoxy-N-metilacridone (6), Arborinine (7), Methyl-arborinine (8), 1-hydroxy-3,6-dimethoxy-N-metilacridone (10), 1,2,3,6-tetramethoxyacridone (9), 1,2,3,6-tetramethoxy-N-metilacridone (4) e 1-hydroxy-2,3,6- trimethoxy-N-metilacridone (5). The last four substances are new structures. Two different biological assays were performed with some isolated compounds. Assays in vitro of chlorophyll inhibition were performed in chloroplasts isolated from spinach leaves, aiming to found models to new photosynthesis inhibitor herbicides, by study of Chl a fluorescence. Substances isolated from Co. marginatus analysed in this assay were active, and the substance 9 was the most active in Chl a fluorescence measures. This result indicates that this molecule could damage the OEC complex and one of his action site is located in FSII, binding to Qa environment. In cytotoxic assays, the substance 6 is the more promising molecule against cancerígenas MCF-7 (breast adenocarcinoma), NCI-460 (non-small cell lung cancer) and A375-C5 (melanoma) cancer cells, showing respectively GJ50 values of 25, 20 e 22 μM. |
publishDate |
2013 |
dc.date.available.fl_str_mv |
2013-09-05 2016-06-02T20:36:46Z |
dc.date.issued.fl_str_mv |
2013-03-27 |
dc.date.accessioned.fl_str_mv |
2016-06-02T20:36:46Z |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/masterThesis |
format |
masterThesis |
status_str |
publishedVersion |
dc.identifier.citation.fl_str_mv |
BELLETE, Barbara Sayuri. Phytochemical study of Conchocarpus marginatus (RUTACEAE), and evaluation of biological potential from isolated compounds. 2013. 204 f. Dissertação (Mestrado em Ciências Exatas e da Terra) - Universidade Federal de São Carlos, São Carlos, 2013. |
dc.identifier.uri.fl_str_mv |
https://repositorio.ufscar.br/handle/ufscar/6561 |
identifier_str_mv |
BELLETE, Barbara Sayuri. Phytochemical study of Conchocarpus marginatus (RUTACEAE), and evaluation of biological potential from isolated compounds. 2013. 204 f. Dissertação (Mestrado em Ciências Exatas e da Terra) - Universidade Federal de São Carlos, São Carlos, 2013. |
url |
https://repositorio.ufscar.br/handle/ufscar/6561 |
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por |
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info:eu-repo/semantics/openAccess |
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openAccess |
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Universidade Federal de São Carlos |
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Programa de Pós-Graduação em Química - PPGQ |
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UFSCar |
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BR |
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Universidade Federal de São Carlos |
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