Estudo fitoquímico de Conchocarpus marginatus (Rutaceae), e avaliação do potencial biológico dos compostos isolados

Detalhes bibliográficos
Autor(a) principal: Bellete, Barbara Sayuri
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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spelling 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
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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.
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