Estudo quimiossistemático de espécies de Hortia (Rutaceae) e busca de fungicidas à Guignardia citricarpa

Detalhes bibliográficos
Autor(a) principal: Freitas, Samya Danielle Lima de
Data de Publicação: 2010
Tipo de documento: Dissertação
Idioma: por
Título da fonte: Repositório Institucional da UFSCAR
Texto Completo: https://repositorio.ufscar.br/handle/ufscar/6477
Resumo: The classification of the Hortia genus, belonging to the Rutaceae, is ambiguous. Hortia, which has been placed in Cusparieae by De Candolle in 1824, in the most recent morphological classification of Engler in 1931 it belongs to Toddalieae. More recently, Silva and colleagues classified again Hortia in Cusparieae. However, the phytochemical study of the species from Hortia genus still not allow classify correctly it inside the family. Thus, the phytochemical study of Hortia described in this paper aims to contribute with the chemosystematics of the Rutaceae and with the best classification of the genus inside the family. The study of the species H. oreadica, H. brasiliana and H. superba led to the isolation and identification of 11 substances, the alkaloids N-methyl-4- methoxy-quinolin-2-one (01), integriquinolone (02), new in the genus Hortia, rutaecarpine (03), the coumarins scoparone (04) xanthotoxin (05), which were first described in the species H. superba, isopimpinellin (06), new in the genus Hortia, 5- chloro-8-methoxy-furanocoumarin (07), new in the literature, prangol (08) and heraclenol (09), and the flavonoids isosakuranetin (10) and neoponcirin (11), the latter being new in the genus Hortia. The presence of metabolites such as alkaloids, coumarins and flavonoids confirm that Hortia belongs to the Rutaceae family, even so are not clear its accurate positioning. Some of the isolated compounds were tested against the inhibition of Guignardia citricarpa following two methods of inhibition assays. One based on inhibition of G. citricarpa in vitro against growth mycelial, by the method of incorporation into the culture medium. The other based on the inhibition test to G. citricarpa in vitro on spore germination and appressorium formation by the method of germination of spores on plates of polystyrene. The first methodology only evaluated the inhibition of the formation of mycelia and it is not directly involved in the infection process of plants, already the second one evaluated the inhibition of reproductive structures of microorganisms (spores), responsible for the infection process. The average growth mycelial for all substances tested revealed the alkaloid N-methyl-4-methoxy-2-quinolin-2-one (100 μg.mL-1) as the most effective among all the substances tested. As the inhibition front of spore germination and appressorium formation, the results were quite satisfactory, the coumarin scoparone (100 μg.mL-1) showed 96% of inhibition spore germination and 99% for the formation of appressorium, the alkaloid N-methyl-4-methoxy-2-quinolin-2-one (100 μg.mL-1) with 83% and 91%, and the flavonoid isosakuranetin (100 μg.mL-1) with 71,4% and 80%, respectively. Therefore, from this study it was found that some natural products with antifungal activity revealed important sources in the discovery of new products free of toxicity and effective as a fungicide.
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spelling Freitas, Samya Danielle Lima deSilva, Maria Fátima das Graças Fernandes dahttp://lattes.cnpq.br/0457632122660653http://lattes.cnpq.br/7961603023838547d0b49acb-584d-4154-ab1c-68ca07f3cfd22016-06-02T20:36:28Z2010-11-252016-06-02T20:36:28Z2010-08-26FREITAS, Samya Danielle Lima de. Chemosystematic study of species of Hortia (Rutaceae) and search of fungicides to Guignardia citricarpa. 2010. 143 f. Dissertação (Mestrado em Ciências Exatas e da Terra) - Universidade Federal de São Carlos, São Carlos, 2010.https://repositorio.ufscar.br/handle/ufscar/6477The classification of the Hortia genus, belonging to the Rutaceae, is ambiguous. Hortia, which has been placed in Cusparieae by De Candolle in 1824, in the most recent morphological classification of Engler in 1931 it belongs to Toddalieae. More recently, Silva and colleagues classified again Hortia in Cusparieae. However, the phytochemical study of the species from Hortia genus still not allow classify correctly it inside the family. Thus, the phytochemical study of Hortia described in this paper aims to contribute with the chemosystematics of the Rutaceae and with the best classification of the genus inside the family. The study of the species H. oreadica, H. brasiliana and H. superba led to the isolation and identification of 11 substances, the alkaloids N-methyl-4- methoxy-quinolin-2-one (01), integriquinolone (02), new in the genus Hortia, rutaecarpine (03), the coumarins scoparone (04) xanthotoxin (05), which were first described in the species H. superba, isopimpinellin (06), new in the genus Hortia, 5- chloro-8-methoxy-furanocoumarin (07), new in the literature, prangol (08) and heraclenol (09), and the flavonoids isosakuranetin (10) and neoponcirin (11), the latter being new in the genus Hortia. The presence of metabolites such as alkaloids, coumarins and flavonoids confirm that Hortia belongs to the Rutaceae family, even so are not clear its accurate positioning. Some of the isolated compounds were tested against the inhibition of Guignardia citricarpa following two methods of inhibition assays. One based on inhibition of G. citricarpa in vitro against growth mycelial, by the method of incorporation into the culture medium. The other based on the inhibition test to G. citricarpa in vitro on spore germination and appressorium formation by the method of germination of spores on plates of polystyrene. The first methodology only evaluated the inhibition of the formation of mycelia and it is not directly involved in the infection process of plants, already the second one evaluated the inhibition of reproductive structures of microorganisms (spores), responsible for the infection process. The average growth mycelial for all substances tested revealed the alkaloid N-methyl-4-methoxy-2-quinolin-2-one (100 μg.mL-1) as the most effective among all the substances tested. As the inhibition front of spore germination and appressorium formation, the results were quite satisfactory, the coumarin scoparone (100 μg.mL-1) showed 96% of inhibition spore germination and 99% for the formation of appressorium, the alkaloid N-methyl-4-methoxy-2-quinolin-2-one (100 μg.mL-1) with 83% and 91%, and the flavonoid isosakuranetin (100 μg.mL-1) with 71,4% and 80%, respectively. Therefore, from this study it was found that some natural products with antifungal activity revealed important sources in the discovery of new products free of toxicity and effective as a fungicide.A classificação do gênero Hortia dentro da família Rutaceae é duvidosa. Hortia, que já foi posicionada em Cusparieae por De Candolle em 1824, na mais recente classificação morfológica de Engler em 1931 pertence a Toddalieae. Mais recentemente da Silva e colaboradores voltam a propor Hortia em Cusparieae. Contudo, o estudo fitoquímico das espécies do gênero Hortia ainda não permitem classificá-la corretamente dentro da família. Desta forma, o estudo fitoquímico de Hortia descrito neste trabalho, visa contribuir com a quimiossistemática da família Rutaceae e também com a melhor classificação do gênero dentro da mesma. O estudo das espécies H. oreadica, H. brasiliana e H. superba levou ao isolamento e identificação de 11 substâncias, sendo os alcalóides N-metil-4-metoxi-2-quinolona (01), integriquinolona (02), inédita no gênero Hortia e a rutaecarpina (03), as cumarinas escoparona (04), xantotoxina (05), sendo estas descritas pela primeira vez na espécie H. superba, isopimpenilina (06), inédita no gênero Hortia, 5-cloro-8-metoxi-furanocumarina (07), inédita na literatura, prangol (08) e heraclenol (09), e os flavonóides isosakuranetina (10) e neoponcirina (11), sendo este último inédito no gênero Hortia. A presença de metabólitos como alcalóides, cumarinas e flavonóides vêm a confirmar que Hortia pertence à família Rutaceae, embora não esteja claro seu exato posicionamento dentro da mesma. Alguns dos compostos isolados foram avaliados frente à inibição do desenvolvimento de Guignardia citricarpa, seguindo duas metodologias de ensaios de inibição, uma baseada no ensaio de inibição de G. citricarpa in vitro frente ao crescimento micelial, pelo método de incorporação ao meio de cultura e a outra, baseada no ensaio de inibição de G. citricarpa in vitro frente à germinação de esporos e formação de apressórios, pelo método de germinação de esporos em placa de poliestireno. Foram submetidas à ambos os ensaios de inibição as substâncias: N-metil-4-metoxi-2-quinolona, escoparona, prangol e isosakuranetina, as quais foram avaliadas quanto sua atividade antifúngica, porém a primeira metodologia avaliou a inibição apenas da formação de micélios, e estes não estão envolvidos diretamente com o processo de infecção das plantas, já a segunda metodologia avaliou a inibição de estruturas reprodutivas do microrganismo (os esporos), responsável pelo processo de infecção. Foram calculadas as médias de crescimento micelial para todas as substâncias testadas, revelando o alcalóide Nmetil- 4-metoxi-2-quinolona (100 μg.mL-1) como o mais eficaz dentre todas as substâncias ensaiadas. Quanto a inibição frente à germinação de esporos e formação de apressórios, os resultados foram bastante satisfatórios, a cumarina escoparona (100 μg.mL-1) apresentou inibição de 96% para a germinação de esporos e 99% para a formação de apressórios, o alcalóide N-metil-4-metoxi-2- quinolona (100 μg.mL-1) com 83% e 91%, e o flavonóide isosakuranetina (100 μg.mL-1) com 71,4% e 80%, respectivamente. Portanto, a partir deste trabalho verificou-se que alguns produtos naturais com potencial antifúngico revelaram importantes fontes na descoberta de novos produtos livres de toxicidade e eficaz como fungicidaUniversidade Federal de Sao Carlosapplication/pdfporUniversidade Federal de São CarlosPrograma de Pós-Graduação em Química - PPGQUFSCarBRProdutos naturaisQuimiossistemáticaHortiaRutaceaeGuignardia citricarpaMancha preta dos citrosCIENCIAS EXATAS E DA TERRA::QUIMICA::QUIMICA ORGANICA::QUIMICA DOS PRODUTOS NATURAISEstudo quimiossistemático de espécies de Hortia (Rutaceae) e busca de fungicidas à Guignardia citricarpaChemosystematic study of species of Hortia (Rutaceae) and search of fungicides to Guignardia citricarpainfo: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:UFSCARORIGINAL3312.pdfapplication/pdf4327625https://repositorio.ufscar.br/bitstream/ufscar/6477/1/3312.pdfaf69914851f0a422fc453d6719c75b20MD51THUMBNAIL3312.pdf.jpg3312.pdf.jpgIM Thumbnailimage/jpeg9685https://repositorio.ufscar.br/bitstream/ufscar/6477/2/3312.pdf.jpg61f49dd34a3773d957eb9ae51c07f559MD52ufscar/64772023-09-18 18:31:11.756oai:repositorio.ufscar.br:ufscar/6477Repositório InstitucionalPUBhttps://repositorio.ufscar.br/oai/requestopendoar:43222023-09-18T18:31:11Repositório Institucional da UFSCAR - Universidade Federal de São Carlos (UFSCAR)false
dc.title.por.fl_str_mv Estudo quimiossistemático de espécies de Hortia (Rutaceae) e busca de fungicidas à Guignardia citricarpa
dc.title.alternative.eng.fl_str_mv Chemosystematic study of species of Hortia (Rutaceae) and search of fungicides to Guignardia citricarpa
title Estudo quimiossistemático de espécies de Hortia (Rutaceae) e busca de fungicidas à Guignardia citricarpa
spellingShingle Estudo quimiossistemático de espécies de Hortia (Rutaceae) e busca de fungicidas à Guignardia citricarpa
Freitas, Samya Danielle Lima de
Produtos naturais
Quimiossistemática
Hortia
Rutaceae
Guignardia citricarpa
Mancha preta dos citros
CIENCIAS EXATAS E DA TERRA::QUIMICA::QUIMICA ORGANICA::QUIMICA DOS PRODUTOS NATURAIS
title_short Estudo quimiossistemático de espécies de Hortia (Rutaceae) e busca de fungicidas à Guignardia citricarpa
title_full Estudo quimiossistemático de espécies de Hortia (Rutaceae) e busca de fungicidas à Guignardia citricarpa
title_fullStr Estudo quimiossistemático de espécies de Hortia (Rutaceae) e busca de fungicidas à Guignardia citricarpa
title_full_unstemmed Estudo quimiossistemático de espécies de Hortia (Rutaceae) e busca de fungicidas à Guignardia citricarpa
title_sort Estudo quimiossistemático de espécies de Hortia (Rutaceae) e busca de fungicidas à Guignardia citricarpa
author Freitas, Samya Danielle Lima de
author_facet Freitas, Samya Danielle Lima de
author_role author
dc.contributor.authorlattes.por.fl_str_mv http://lattes.cnpq.br/7961603023838547
dc.contributor.author.fl_str_mv Freitas, Samya Danielle Lima de
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 d0b49acb-584d-4154-ab1c-68ca07f3cfd2
contributor_str_mv Silva, Maria Fátima das Graças Fernandes da
dc.subject.por.fl_str_mv Produtos naturais
Quimiossistemática
Hortia
Rutaceae
Guignardia citricarpa
Mancha preta dos citros
topic Produtos naturais
Quimiossistemática
Hortia
Rutaceae
Guignardia citricarpa
Mancha preta dos citros
CIENCIAS EXATAS E DA TERRA::QUIMICA::QUIMICA ORGANICA::QUIMICA DOS PRODUTOS NATURAIS
dc.subject.cnpq.fl_str_mv CIENCIAS EXATAS E DA TERRA::QUIMICA::QUIMICA ORGANICA::QUIMICA DOS PRODUTOS NATURAIS
description The classification of the Hortia genus, belonging to the Rutaceae, is ambiguous. Hortia, which has been placed in Cusparieae by De Candolle in 1824, in the most recent morphological classification of Engler in 1931 it belongs to Toddalieae. More recently, Silva and colleagues classified again Hortia in Cusparieae. However, the phytochemical study of the species from Hortia genus still not allow classify correctly it inside the family. Thus, the phytochemical study of Hortia described in this paper aims to contribute with the chemosystematics of the Rutaceae and with the best classification of the genus inside the family. The study of the species H. oreadica, H. brasiliana and H. superba led to the isolation and identification of 11 substances, the alkaloids N-methyl-4- methoxy-quinolin-2-one (01), integriquinolone (02), new in the genus Hortia, rutaecarpine (03), the coumarins scoparone (04) xanthotoxin (05), which were first described in the species H. superba, isopimpinellin (06), new in the genus Hortia, 5- chloro-8-methoxy-furanocoumarin (07), new in the literature, prangol (08) and heraclenol (09), and the flavonoids isosakuranetin (10) and neoponcirin (11), the latter being new in the genus Hortia. The presence of metabolites such as alkaloids, coumarins and flavonoids confirm that Hortia belongs to the Rutaceae family, even so are not clear its accurate positioning. Some of the isolated compounds were tested against the inhibition of Guignardia citricarpa following two methods of inhibition assays. One based on inhibition of G. citricarpa in vitro against growth mycelial, by the method of incorporation into the culture medium. The other based on the inhibition test to G. citricarpa in vitro on spore germination and appressorium formation by the method of germination of spores on plates of polystyrene. The first methodology only evaluated the inhibition of the formation of mycelia and it is not directly involved in the infection process of plants, already the second one evaluated the inhibition of reproductive structures of microorganisms (spores), responsible for the infection process. The average growth mycelial for all substances tested revealed the alkaloid N-methyl-4-methoxy-2-quinolin-2-one (100 μg.mL-1) as the most effective among all the substances tested. As the inhibition front of spore germination and appressorium formation, the results were quite satisfactory, the coumarin scoparone (100 μg.mL-1) showed 96% of inhibition spore germination and 99% for the formation of appressorium, the alkaloid N-methyl-4-methoxy-2-quinolin-2-one (100 μg.mL-1) with 83% and 91%, and the flavonoid isosakuranetin (100 μg.mL-1) with 71,4% and 80%, respectively. Therefore, from this study it was found that some natural products with antifungal activity revealed important sources in the discovery of new products free of toxicity and effective as a fungicide.
publishDate 2010
dc.date.available.fl_str_mv 2010-11-25
2016-06-02T20:36:28Z
dc.date.issued.fl_str_mv 2010-08-26
dc.date.accessioned.fl_str_mv 2016-06-02T20:36:28Z
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dc.identifier.citation.fl_str_mv FREITAS, Samya Danielle Lima de. Chemosystematic study of species of Hortia (Rutaceae) and search of fungicides to Guignardia citricarpa. 2010. 143 f. Dissertação (Mestrado em Ciências Exatas e da Terra) - Universidade Federal de São Carlos, São Carlos, 2010.
dc.identifier.uri.fl_str_mv https://repositorio.ufscar.br/handle/ufscar/6477
identifier_str_mv FREITAS, Samya Danielle Lima de. Chemosystematic study of species of Hortia (Rutaceae) and search of fungicides to Guignardia citricarpa. 2010. 143 f. Dissertação (Mestrado em Ciências Exatas e da Terra) - Universidade Federal de São Carlos, São Carlos, 2010.
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