Estudo fitoquímico biomonitorado de Duguetia lanceolata e Lithraea molleoides no controle de pragas agrícolas e processos de nanoencapsulamento

Detalhes bibliográficos
Autor(a) principal: Domingues, Vanessa de Cássia
Data de Publicação: 2016
Tipo de documento: Tese
Idioma: por
Título da fonte: Repositório Institucional da UFSCAR
Texto Completo: https://repositorio.ufscar.br/handle/ufscar/14357
Resumo: Leafcutter ants and maize weevil are responsible for great losses in Brazilian agriculture due to the difficult control of these pests. Natural products are becoming increasingly important, mainly in the search for non-toxic chemical compounds to humans, animals and environment and that can bio-rationally control agricultural pests’ behavior, such as insects and fungi. Different methods and new strategies have been the subject of studies to provide propositions for pest control. Among them, the search in nature for new compounds with insecticide and fungicide potential, as well as a synthesis of natural products derivatives with these properties. Accordingly, this study aimed the search of active fractions and compounds as regards the leafcutter ants Atta sexdens rubropilosa, its symbiotic fungus Leucoagaricus gongylophorus and Sitophilus zeamais, as known as maize weevil. Through bio-monitored phytochemical studies of the extracts of the plant parts of Duguetia lanceolata (Annonaceae) and Lithraea molleoides (Anacardeaceae), fractions with potential for pest control were found. The present study led to the isolation/identification of 19 substances, including some insecticide and fungicide emphasis. Current studies have been looking for new technologies for active ingredients application and nanoencapsulation seems to be a technique with great potential since systems for controlled release of substances controlling the stability of chemical actives can be found in it. Therefore, the other aspect of this work is related to the development of nanocapsules from biodegradable polymers for the nanoencapsulation of cedrelone, isolated from Trichilia catigua, as well as some semi-syntheses with the cedrelone limonoid, in the search of cedrelone derivatives to be tested on ants and fungi in order to enhance their fungicide and insecticide activities. For the large-scale isolation of cedrelone, present in T. catigua, the CCC technique (countercurrent chromatography) has proved to be successful, with some advantages, such as solvent and time savings, reproducibility and total sample recovery. During the development of formulations for nanoencapsulation, the nanoprecipitation technique proved to be both viable and reproducible for encapsulation. All formulations were stable and with high encapsulation efficiency. For cedrelone derivatives, cedrelone mesylate, propionate cedrelone and cedrelone acetate were synthesized and cedrelone propionate and cedrelone acetate showed great fungicide/insecticide potential against leafcutter ants.
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spelling Domingues, Vanessa de CássiaFernandes, João Batistahttp://lattes.cnpq.br/2691336077459602http://lattes.cnpq.br/3062709553451994ed44bb15-98fb-4c13-ad76-9482b8f5690a2021-06-09T21:04:42Z2021-06-09T21:04:42Z2016-04-29DOMINGUES, Vanessa de Cássia. Estudo fitoquímico biomonitorado de Duguetia lanceolata e Lithraea molleoides no controle de pragas agrícolas e processos de nanoencapsulamento. 2016. Tese (Doutorado em Química) – Universidade Federal de São Carlos, São Carlos, 2016. Disponível em: https://repositorio.ufscar.br/handle/ufscar/14357.https://repositorio.ufscar.br/handle/ufscar/14357Leafcutter ants and maize weevil are responsible for great losses in Brazilian agriculture due to the difficult control of these pests. Natural products are becoming increasingly important, mainly in the search for non-toxic chemical compounds to humans, animals and environment and that can bio-rationally control agricultural pests’ behavior, such as insects and fungi. Different methods and new strategies have been the subject of studies to provide propositions for pest control. Among them, the search in nature for new compounds with insecticide and fungicide potential, as well as a synthesis of natural products derivatives with these properties. Accordingly, this study aimed the search of active fractions and compounds as regards the leafcutter ants Atta sexdens rubropilosa, its symbiotic fungus Leucoagaricus gongylophorus and Sitophilus zeamais, as known as maize weevil. Through bio-monitored phytochemical studies of the extracts of the plant parts of Duguetia lanceolata (Annonaceae) and Lithraea molleoides (Anacardeaceae), fractions with potential for pest control were found. The present study led to the isolation/identification of 19 substances, including some insecticide and fungicide emphasis. Current studies have been looking for new technologies for active ingredients application and nanoencapsulation seems to be a technique with great potential since systems for controlled release of substances controlling the stability of chemical actives can be found in it. Therefore, the other aspect of this work is related to the development of nanocapsules from biodegradable polymers for the nanoencapsulation of cedrelone, isolated from Trichilia catigua, as well as some semi-syntheses with the cedrelone limonoid, in the search of cedrelone derivatives to be tested on ants and fungi in order to enhance their fungicide and insecticide activities. For the large-scale isolation of cedrelone, present in T. catigua, the CCC technique (countercurrent chromatography) has proved to be successful, with some advantages, such as solvent and time savings, reproducibility and total sample recovery. During the development of formulations for nanoencapsulation, the nanoprecipitation technique proved to be both viable and reproducible for encapsulation. All formulations were stable and with high encapsulation efficiency. For cedrelone derivatives, cedrelone mesylate, propionate cedrelone and cedrelone acetate were synthesized and cedrelone propionate and cedrelone acetate showed great fungicide/insecticide potential against leafcutter ants.As formigas cortadeiras e o gorgulho do milho são responsáveis por grandes prejuízos na agricultura brasileira devido ao difícil controle destas pragas. Produtos naturais vêm conquistando grande importância, principalmente na busca de compostos químicos que não sejam tóxicos aos homens, aos animais e ao meio ambiente e que possam controlar biorracionalmente o comportamento de pragas agrícolas, como insetos e fungos. Diferentes métodos e novas estratégias têm sido alvo de estudos em busca de propostas para o controle de pragas. Dentre elas, destaca-se a busca na natureza de novos compostos com potencial inseticida e fungicida, bem como a síntese de derivados de produtos naturais com estas propriedades. Nesta perspectiva, este trabalho visou a busca de compostos e frações ativas frente às formigas cortadeiras Atta sexdens rubropilosa, o seu fungo simbionte Leucoagaricus gongylophorus e Sitophilus zeamais, também conhecido como gorgulho-do-milho. Através de estudos fitoquímicos biomonitorados dos extratos das partes de vegetais de Duguetia lanceolata (Annonaceae) e Lithraea molleoides (Anacardeaceae), verificou-se frações com potencial no controle de pragas. Este estudo levou ao isolamento/identificação de 19 substâncias, incluindo algumas com destaque inseticida/fungicida. Atualmente, estudos vêm buscando novas tecnologias para aplicação de princípios ativos e o nanoencapsulamento vem demonstrando ser uma técnica com grande potencial, visto que podemos encontrar sistemas de liberação controlada de substâncias controlando a estabilidade dos ativos. Portanto, a outra vertente do trabalho está relacionada ao desenvolvimento de nanocápsulas a partir de polímeros biodegradáveis para nanoencapsulação da cedrelona isolada de Trichilia catigua, bem como algumas semi-sínteses com limonoide cedrelona, na busca de análogos a serem ensaiados nas formigas e fungos a fim de potencializar a atividade fungicida e inseticida. Para o isolamento em larga escala da cedrelona, presente em T.catigua, a técnica de CCC (cromatografia em contracorrente) se mostrou eficiente, com diferenciais, tais como economia de solvente e tempo, reprodutibilidade e recuperação total das amostras. No desenvolvimento de formulações para nanoencapsulamento da cedrelona, a técnica de nanoprecipitação mostrou-se viável e reprodutível para encapsulamento. Todas as formulações se mostraram estáveis, com alta eficiência de encapsulamento. Para os análogos da cedrelona, foram sintetizados o mesilato de cedrelona, o propionato de cerelona e o acetato de cedrelona. Dentre eles, o propionato de cerelona e o acetato de cedrelona foram os que apresentaram grande potencial fungicida/inseticida contra as formigas cortadeiras.Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)FAPESP: 2010/18303-1porUniversidade Federal de São CarlosCâmpus São CarlosPrograma de Pós-Graduação em Química - PPGQUFSCarAttribution-NonCommercial-NoDerivs 3.0 Brazilhttp://creativecommons.org/licenses/by-nc-nd/3.0/br/info:eu-repo/semantics/openAccessQuímica orgânicaProdutos naturaisNanoformulaçõesControle de insetos pragasDuguetia lanceolataLithraea molleoidesAtta sexdens rubropilosaLeucoagaricus gongylophorusCromatografiaNanoencapsulationNatural productsSitophilus zeamaisOrganic chemistryChromatographyCIENCIAS EXATAS E DA TERRA::QUIMICA::QUIMICA ORGANICA::QUIMICA DOS PRODUTOS NATURAISEstudo fitoquímico biomonitorado de Duguetia lanceolata e Lithraea molleoides no controle de pragas agrícolas e processos de nanoencapsulamentoBiomonitored phytochemical study of Duguetia lanceolata and Lithraea molleoides in agricultural pest control and nanoencapsulation processesinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/doctoralThesis600600f08d89b4-2b31-4e90-9be7-b86a7c15645creponame:Repositório Institucional da UFSCARinstname:Universidade Federal de São Carlos (UFSCAR)instacron:UFSCARORIGINALTESE VCD.pdfTESE VCD.pdfTese de Doutoradoapplication/pdf6091912https://repositorio.ufscar.br/bitstream/ufscar/14357/1/TESE%20%20VCD.pdf095f45cb648af454e60447caa520b0b4MD51Carta encaminhamento.pdfCarta encaminhamento.pdfapplication/pdf479121https://repositorio.ufscar.br/bitstream/ufscar/14357/3/Carta%20encaminhamento.pdfa8fe92125fc6cbe003290689a5b25ed8MD53CC-LICENSElicense_rdflicense_rdfapplication/rdf+xml; charset=utf-8811https://repositorio.ufscar.br/bitstream/ufscar/14357/4/license_rdfe39d27027a6cc9cb039ad269a5db8e34MD54TEXTTESE VCD.pdf.txtTESE VCD.pdf.txtExtracted texttext/plain402452https://repositorio.ufscar.br/bitstream/ufscar/14357/5/TESE%20%20VCD.pdf.txte7b41692e0fea3c2612c01438b0fe644MD55Carta encaminhamento.pdf.txtCarta encaminhamento.pdf.txtExtracted texttext/plain1428https://repositorio.ufscar.br/bitstream/ufscar/14357/7/Carta%20encaminhamento.pdf.txt5e9ee98b6847a7180a0f9734e5162819MD57THUMBNAILTESE VCD.pdf.jpgTESE VCD.pdf.jpgIM Thumbnailimage/jpeg10873https://repositorio.ufscar.br/bitstream/ufscar/14357/6/TESE%20%20VCD.pdf.jpga651789e502621c2200a15dee14902bcMD56Carta encaminhamento.pdf.jpgCarta encaminhamento.pdf.jpgIM Thumbnailimage/jpeg12702https://repositorio.ufscar.br/bitstream/ufscar/14357/8/Carta%20encaminhamento.pdf.jpgcbfba413e6be18dec8da6ed5fc7a5c95MD58ufscar/143572023-09-18 18:32:11.59oai:repositorio.ufscar.br:ufscar/14357Repositório InstitucionalPUBhttps://repositorio.ufscar.br/oai/requestopendoar:43222023-09-18T18:32:11Repositório Institucional da UFSCAR - Universidade Federal de São Carlos (UFSCAR)false
dc.title.por.fl_str_mv Estudo fitoquímico biomonitorado de Duguetia lanceolata e Lithraea molleoides no controle de pragas agrícolas e processos de nanoencapsulamento
dc.title.alternative.eng.fl_str_mv Biomonitored phytochemical study of Duguetia lanceolata and Lithraea molleoides in agricultural pest control and nanoencapsulation processes
title Estudo fitoquímico biomonitorado de Duguetia lanceolata e Lithraea molleoides no controle de pragas agrícolas e processos de nanoencapsulamento
spellingShingle Estudo fitoquímico biomonitorado de Duguetia lanceolata e Lithraea molleoides no controle de pragas agrícolas e processos de nanoencapsulamento
Domingues, Vanessa de Cássia
Química orgânica
Produtos naturais
Nanoformulações
Controle de insetos pragas
Duguetia lanceolata
Lithraea molleoides
Atta sexdens rubropilosa
Leucoagaricus gongylophorus
Cromatografia
Nanoencapsulation
Natural products
Sitophilus zeamais
Organic chemistry
Chromatography
CIENCIAS EXATAS E DA TERRA::QUIMICA::QUIMICA ORGANICA::QUIMICA DOS PRODUTOS NATURAIS
title_short Estudo fitoquímico biomonitorado de Duguetia lanceolata e Lithraea molleoides no controle de pragas agrícolas e processos de nanoencapsulamento
title_full Estudo fitoquímico biomonitorado de Duguetia lanceolata e Lithraea molleoides no controle de pragas agrícolas e processos de nanoencapsulamento
title_fullStr Estudo fitoquímico biomonitorado de Duguetia lanceolata e Lithraea molleoides no controle de pragas agrícolas e processos de nanoencapsulamento
title_full_unstemmed Estudo fitoquímico biomonitorado de Duguetia lanceolata e Lithraea molleoides no controle de pragas agrícolas e processos de nanoencapsulamento
title_sort Estudo fitoquímico biomonitorado de Duguetia lanceolata e Lithraea molleoides no controle de pragas agrícolas e processos de nanoencapsulamento
author Domingues, Vanessa de Cássia
author_facet Domingues, Vanessa de Cássia
author_role author
dc.contributor.authorlattes.por.fl_str_mv http://lattes.cnpq.br/3062709553451994
dc.contributor.author.fl_str_mv Domingues, Vanessa de Cássia
dc.contributor.advisor1.fl_str_mv Fernandes, João Batista
dc.contributor.advisor1Lattes.fl_str_mv http://lattes.cnpq.br/2691336077459602
dc.contributor.authorID.fl_str_mv ed44bb15-98fb-4c13-ad76-9482b8f5690a
contributor_str_mv Fernandes, João Batista
dc.subject.por.fl_str_mv Química orgânica
Produtos naturais
Nanoformulações
Controle de insetos pragas
Duguetia lanceolata
Lithraea molleoides
Atta sexdens rubropilosa
Leucoagaricus gongylophorus
Cromatografia
topic Química orgânica
Produtos naturais
Nanoformulações
Controle de insetos pragas
Duguetia lanceolata
Lithraea molleoides
Atta sexdens rubropilosa
Leucoagaricus gongylophorus
Cromatografia
Nanoencapsulation
Natural products
Sitophilus zeamais
Organic chemistry
Chromatography
CIENCIAS EXATAS E DA TERRA::QUIMICA::QUIMICA ORGANICA::QUIMICA DOS PRODUTOS NATURAIS
dc.subject.eng.fl_str_mv Nanoencapsulation
Natural products
Sitophilus zeamais
Organic chemistry
Chromatography
dc.subject.cnpq.fl_str_mv CIENCIAS EXATAS E DA TERRA::QUIMICA::QUIMICA ORGANICA::QUIMICA DOS PRODUTOS NATURAIS
description Leafcutter ants and maize weevil are responsible for great losses in Brazilian agriculture due to the difficult control of these pests. Natural products are becoming increasingly important, mainly in the search for non-toxic chemical compounds to humans, animals and environment and that can bio-rationally control agricultural pests’ behavior, such as insects and fungi. Different methods and new strategies have been the subject of studies to provide propositions for pest control. Among them, the search in nature for new compounds with insecticide and fungicide potential, as well as a synthesis of natural products derivatives with these properties. Accordingly, this study aimed the search of active fractions and compounds as regards the leafcutter ants Atta sexdens rubropilosa, its symbiotic fungus Leucoagaricus gongylophorus and Sitophilus zeamais, as known as maize weevil. Through bio-monitored phytochemical studies of the extracts of the plant parts of Duguetia lanceolata (Annonaceae) and Lithraea molleoides (Anacardeaceae), fractions with potential for pest control were found. The present study led to the isolation/identification of 19 substances, including some insecticide and fungicide emphasis. Current studies have been looking for new technologies for active ingredients application and nanoencapsulation seems to be a technique with great potential since systems for controlled release of substances controlling the stability of chemical actives can be found in it. Therefore, the other aspect of this work is related to the development of nanocapsules from biodegradable polymers for the nanoencapsulation of cedrelone, isolated from Trichilia catigua, as well as some semi-syntheses with the cedrelone limonoid, in the search of cedrelone derivatives to be tested on ants and fungi in order to enhance their fungicide and insecticide activities. For the large-scale isolation of cedrelone, present in T. catigua, the CCC technique (countercurrent chromatography) has proved to be successful, with some advantages, such as solvent and time savings, reproducibility and total sample recovery. During the development of formulations for nanoencapsulation, the nanoprecipitation technique proved to be both viable and reproducible for encapsulation. All formulations were stable and with high encapsulation efficiency. For cedrelone derivatives, cedrelone mesylate, propionate cedrelone and cedrelone acetate were synthesized and cedrelone propionate and cedrelone acetate showed great fungicide/insecticide potential against leafcutter ants.
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dc.date.issued.fl_str_mv 2016-04-29
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dc.identifier.citation.fl_str_mv DOMINGUES, Vanessa de Cássia. Estudo fitoquímico biomonitorado de Duguetia lanceolata e Lithraea molleoides no controle de pragas agrícolas e processos de nanoencapsulamento. 2016. Tese (Doutorado em Química) – Universidade Federal de São Carlos, São Carlos, 2016. Disponível em: https://repositorio.ufscar.br/handle/ufscar/14357.
dc.identifier.uri.fl_str_mv https://repositorio.ufscar.br/handle/ufscar/14357
identifier_str_mv DOMINGUES, Vanessa de Cássia. Estudo fitoquímico biomonitorado de Duguetia lanceolata e Lithraea molleoides no controle de pragas agrícolas e processos de nanoencapsulamento. 2016. Tese (Doutorado em Química) – Universidade Federal de São Carlos, São Carlos, 2016. Disponível em: https://repositorio.ufscar.br/handle/ufscar/14357.
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