Síntese e avaliação da fitotoxicidade de novas lactonas sesquiterpênicas

Detalhes bibliográficos
Autor(a) principal: Arantes, Francisco Frederico Pelinson
Data de Publicação: 2007
Tipo de documento: Dissertação
Idioma: por
Título da fonte: LOCUS Repositório Institucional da UFV
Texto Completo: http://locus.ufv.br/handle/123456789/2167
Resumo: Sesquiterpene lactones represent an important group of secondary metabolites of the Asteraceae family. As the availability of natural sesquiterpene lactones is very limited, being many times insufficient for detailed studies of their bioactivity, the present investigation had as objective the synthesis of sesquiterpene lactones derivatives from α-santonin, aiming studies about the biological structure-activity relationship and the discovery of new compounds with potential herbicide activity. In this present work eleven compounds were synthesized [20]-[30], five among them are unknown. These compounds were prepared by different types of reactions including photochemistry, reduction, oxidation and esterification reactions. When α-santonin [9] was irradiated with high pressure mercury lamp, using anhydrous acetic acid as solvent in borosilicate reactor, 10α- acetoxy-3-oxo-1,7αH,6,11βH-guai-4-en-6,12-olide [20] was obtained, in 26% yield. Using acetic acid/water mixture 1:1 v/v, keeping the other conditions, the iso-foto-santonic acid [21] and the 10α-hydroxy-3-oxo-1,7αH,6,11βH-guai-4-en-6,12-olide [22] were obtained in 44% and 32% yields, respectively. When the α-santonine was submitted to the photochemistry reaction in a quartz reactor, using low pressure mercury lamp as source of ultraviolet radiation and acetonitrile as solvent, the lumisantonin [23] was produced in 83% yield. The compounds [20] and [22] were submitted to the reduction reaction with sodium borohydride, obtaining 10α-acetoxy-3β-hidroxy-1,7αH,6,11βH-guai-4-en-6,12-olide [28] and the 3β,10α-hydroxy-1,7αH,6,11βH-guai-4-en-6,12-olide [30] in 86% and 72% yields, respectively. To obtain 10α-acetoxy-3β-crotonoil-1,7αH,6,11βH-guai-4-en-6,12-olide [29] (63%), the compound [28] reacted with crotonoil chloride, in the presence of pyridine. The 3-oxo-7αH,6βH-eudesma-1,4,11-trien-6,12-olide [25] was obtained in 72% yield and, it was prepared by the initial reaction of the α-santonine with phenyl selenium chloride (PhSeCl) and subsequent oxidation with hydrogen peroxide (H2O2). Then, the lactone [25] was submitted to the photochemistry reaction in a quartz reactor, using anhydrous acetic acid as solvent, and the compounds 10α-acetoxy-3-oxo-1,7αH,6βH-guai-4,11-dien-6,12-olide [26] and 11,13 deidrolumisantonin [27] were obtained in 4,5% and 18% yields, respectively. The compounds [20] and [30] were submitted to biological assays to evaluate their activities on the germination and on the radicular growth of cucumber (Cucumis sativus) and sorghum plants (Sorghum bicolor x Sorghum sudanensis). Amongst all evaluated compounds, the compound [20] was the one that presented higher activity on the radicular growth of the cucumber and sorghum plantules, being inhibitions of 53,5% and 66,7% observed, respectively. Low or no significant inhibitory activity was observed on the germination of the cucumber and sorghum seeds.
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spelling Arantes, Francisco Frederico Pelinsonhttp://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4772431H0Demuner, Antônio Jacintohttp://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4783217D3Barbosa, Luiz Claudio de Almeidahttp://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4781106J2Alvarenga, Elson Santiago dehttp://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4784664Y6Fernandes, Sergio Antôniohttp://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4760152Y5Paula, Vanderlúcia Fonseca dehttp://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4723796T62015-03-26T13:00:39Z2007-07-232015-03-26T13:00:39Z2007-02-16ARANTES, Francisco Frederico Pelinson. Synthesis and evaluation of the phytotoxicity of new sesquiterpe lactones. 2007. 147 f. Dissertação (Mestrado em Agroquímica analítica; Agroquímica inorgânica e Físico-química; Agroquímica orgânica) - Universidade Federal de Viçosa, Viçosa, 2007.http://locus.ufv.br/handle/123456789/2167Sesquiterpene lactones represent an important group of secondary metabolites of the Asteraceae family. As the availability of natural sesquiterpene lactones is very limited, being many times insufficient for detailed studies of their bioactivity, the present investigation had as objective the synthesis of sesquiterpene lactones derivatives from α-santonin, aiming studies about the biological structure-activity relationship and the discovery of new compounds with potential herbicide activity. In this present work eleven compounds were synthesized [20]-[30], five among them are unknown. These compounds were prepared by different types of reactions including photochemistry, reduction, oxidation and esterification reactions. When α-santonin [9] was irradiated with high pressure mercury lamp, using anhydrous acetic acid as solvent in borosilicate reactor, 10α- acetoxy-3-oxo-1,7αH,6,11βH-guai-4-en-6,12-olide [20] was obtained, in 26% yield. Using acetic acid/water mixture 1:1 v/v, keeping the other conditions, the iso-foto-santonic acid [21] and the 10α-hydroxy-3-oxo-1,7αH,6,11βH-guai-4-en-6,12-olide [22] were obtained in 44% and 32% yields, respectively. When the α-santonine was submitted to the photochemistry reaction in a quartz reactor, using low pressure mercury lamp as source of ultraviolet radiation and acetonitrile as solvent, the lumisantonin [23] was produced in 83% yield. The compounds [20] and [22] were submitted to the reduction reaction with sodium borohydride, obtaining 10α-acetoxy-3β-hidroxy-1,7αH,6,11βH-guai-4-en-6,12-olide [28] and the 3β,10α-hydroxy-1,7αH,6,11βH-guai-4-en-6,12-olide [30] in 86% and 72% yields, respectively. To obtain 10α-acetoxy-3β-crotonoil-1,7αH,6,11βH-guai-4-en-6,12-olide [29] (63%), the compound [28] reacted with crotonoil chloride, in the presence of pyridine. The 3-oxo-7αH,6βH-eudesma-1,4,11-trien-6,12-olide [25] was obtained in 72% yield and, it was prepared by the initial reaction of the α-santonine with phenyl selenium chloride (PhSeCl) and subsequent oxidation with hydrogen peroxide (H2O2). Then, the lactone [25] was submitted to the photochemistry reaction in a quartz reactor, using anhydrous acetic acid as solvent, and the compounds 10α-acetoxy-3-oxo-1,7αH,6βH-guai-4,11-dien-6,12-olide [26] and 11,13 deidrolumisantonin [27] were obtained in 4,5% and 18% yields, respectively. The compounds [20] and [30] were submitted to biological assays to evaluate their activities on the germination and on the radicular growth of cucumber (Cucumis sativus) and sorghum plants (Sorghum bicolor x Sorghum sudanensis). Amongst all evaluated compounds, the compound [20] was the one that presented higher activity on the radicular growth of the cucumber and sorghum plantules, being inhibitions of 53,5% and 66,7% observed, respectively. Low or no significant inhibitory activity was observed on the germination of the cucumber and sorghum seeds.Lactonas sesquiterpênicas representam um importante grupo de metabólitos secundários da família Asteraceae. Como a disponibilidade de lactonas sesquiterpênicas naturais é muito limitada, sendo muitas vezes insuficiente para estudos detalhados de suas bioatividades, esse trabalho tem como objetivo a síntese de lactonas sesquiterpênicas derivadas da α-santonina, visando estudos sobre a correlação estrutura-atividade biológica e a descoberta de novos compostos com potencial atividade herbicida. Foram obtidos onze compostos [20] [30], dentre os quais cinco são inéditos. Esses compostos foram preparados através de diferentes tipos de reações (reação fotoquímica, reação de redução, de oxidação e de esterificação). Ao se irradiar a α-santonina [9] com lâmpada de mercúrio de alta pressão, utilizando-se ácido acético anidro como solvente e reator de borossilicato, foi obtido o 10α-acetoxi-3-oxo-1,7αH,6,11βH-guaia-4-en-6,12- olídeo [20], com 26% de rendimento. Ao se utilizar a mistura de solventes ácido acético/água 1:1, mantendo-se as demais condições, foram obtidos o ácido isofotossantônico [21] e o 10α-hidroxi-3-oxo-1,7αH,6,11βH-guaia-4-en-6,12-olídeo [22] com rendimentos de 44% e 32%, respectivamente. Quando a α-santonina foi submetida à reação fotoquímica em reator de quartzo, utilizando-se lâmpadas de mercúrio de baixa pressão como fonte de radiação de luz ultravioleta e acetonitrila como solvente, a lumissantonina [23] foi produzida com 83%. Os compostos [20] e [22] foram submetidos à reação de redução com boroidreto de sódio, sendo obtidos o 10α-acetoxi-3β-hidroxi-1,7αH,6,11βH-guaia-4-en-6,12-olídeo [28] e o 3β,10α-hidroxi-1,7αH,6,11βH-guaia-4-en-6,12-olídeo [30] com rendimentos de 86% e 72%, respectivamente. Para a obtenção do 10α-acetoxi-3β-crotonoil-1,7αH,6,11βH-guaia-4-en-6,12-olídeo [29] (63%), reagiu-se o composto [28] com cloreto de crotonoíla, em presença de piridina. O 3-oxo-7αH,6βH-eudesma-1,4,11-trien-6,12-olídeo [25], obtido com um rendimento de 72%, foi preparado pela reação inicial da α-santonina com cloreto de fenilselênio (PhSeCl) e posterior oxidação com peróxido de hidrogênio (H2O2). A lactona [25] foi então submetida à reação fotoquímica em reator de quartzo, utilizando-se ácido acético anidro como solvente, sendo obtidos os compostos 10α-acetoxi-3-oxo-1,7αH,6βH-guaia-4,11-dien-6,12-olídeo [26] e 11,13 deidrolumissantonina [27] com rendimentos de 4,5 % e 18%, respectivamente. Os compostos [20] [30] foram submetidos a ensaios biológicos para avaliar suas atividades sobre a germinação e o crescimento radicular de pepino (Cucumis sativus) e sorgo (Sorghum bicolor x Sorghum sudanensis). Dentre os compostos avaliados, o que apresentou maior atividade sobre o crescimento radicular das plântulas de pepino e sorgo foi o composto [20], sendo observadas inibições de 53,5% e 66,7%, respectivamente. Baixa ou nenhuma atividade inibitória sobre a germinação das sementes de pepino e sorgo foi observada.Fundação de Amparo a Pesquisa do Estado de Minas Geraisapplication/pdfporUniversidade Federal de ViçosaMestrado em AgroquímicaUFVBRAgroquímica analítica; Agroquímica inorgânica e Físico-química; Agroquímica orgânicaα-santoninaHerbicidaLactonas sesquiterpênicasα-santonineHerbicideSesquiterpe lactonesCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA::QUIMICA ORGANICASíntese e avaliação da fitotoxicidade de novas lactonas sesquiterpênicasSynthesis and evaluation of the phytotoxicity of new sesquiterpe lactonesinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesisinfo:eu-repo/semantics/openAccessreponame:LOCUS Repositório Institucional da UFVinstname:Universidade Federal de Viçosa (UFV)instacron:UFVORIGINALtexto completo.pdfapplication/pdf5454987https://locus.ufv.br//bitstream/123456789/2167/1/texto%20completo.pdf4120176faf71829e2ae56d2cbe75fa21MD51THUMBNAILtexto completo.pdf.jpgtexto completo.pdf.jpgIM Thumbnailimage/jpeg3768https://locus.ufv.br//bitstream/123456789/2167/2/texto%20completo.pdf.jpg3c17566d22011f76bf52e66b8db2331aMD52123456789/21672017-10-06 15:24:13.607oai:locus.ufv.br:123456789/2167Repositório InstitucionalPUBhttps://www.locus.ufv.br/oai/requestfabiojreis@ufv.bropendoar:21452017-10-06T18:24:13LOCUS Repositório Institucional da UFV - Universidade Federal de Viçosa (UFV)false
dc.title.por.fl_str_mv Síntese e avaliação da fitotoxicidade de novas lactonas sesquiterpênicas
dc.title.alternative.eng.fl_str_mv Synthesis and evaluation of the phytotoxicity of new sesquiterpe lactones
title Síntese e avaliação da fitotoxicidade de novas lactonas sesquiterpênicas
spellingShingle Síntese e avaliação da fitotoxicidade de novas lactonas sesquiterpênicas
Arantes, Francisco Frederico Pelinson
α-santonina
Herbicida
Lactonas sesquiterpênicas
α-santonine
Herbicide
Sesquiterpe lactones
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA::QUIMICA ORGANICA
title_short Síntese e avaliação da fitotoxicidade de novas lactonas sesquiterpênicas
title_full Síntese e avaliação da fitotoxicidade de novas lactonas sesquiterpênicas
title_fullStr Síntese e avaliação da fitotoxicidade de novas lactonas sesquiterpênicas
title_full_unstemmed Síntese e avaliação da fitotoxicidade de novas lactonas sesquiterpênicas
title_sort Síntese e avaliação da fitotoxicidade de novas lactonas sesquiterpênicas
author Arantes, Francisco Frederico Pelinson
author_facet Arantes, Francisco Frederico Pelinson
author_role author
dc.contributor.authorLattes.por.fl_str_mv http://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4772431H0
dc.contributor.author.fl_str_mv Arantes, Francisco Frederico Pelinson
dc.contributor.advisor-co1.fl_str_mv Demuner, Antônio Jacinto
dc.contributor.advisor-co1Lattes.fl_str_mv http://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4783217D3
dc.contributor.advisor1.fl_str_mv Barbosa, Luiz Claudio de Almeida
dc.contributor.advisor1Lattes.fl_str_mv http://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4781106J2
dc.contributor.referee1.fl_str_mv Alvarenga, Elson Santiago de
dc.contributor.referee1Lattes.fl_str_mv http://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4784664Y6
dc.contributor.referee2.fl_str_mv Fernandes, Sergio Antônio
dc.contributor.referee2Lattes.fl_str_mv http://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4760152Y5
dc.contributor.referee3.fl_str_mv Paula, Vanderlúcia Fonseca de
dc.contributor.referee3Lattes.fl_str_mv http://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4723796T6
contributor_str_mv Demuner, Antônio Jacinto
Barbosa, Luiz Claudio de Almeida
Alvarenga, Elson Santiago de
Fernandes, Sergio Antônio
Paula, Vanderlúcia Fonseca de
dc.subject.por.fl_str_mv α-santonina
Herbicida
Lactonas sesquiterpênicas
topic α-santonina
Herbicida
Lactonas sesquiterpênicas
α-santonine
Herbicide
Sesquiterpe lactones
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA::QUIMICA ORGANICA
dc.subject.eng.fl_str_mv α-santonine
Herbicide
Sesquiterpe lactones
dc.subject.cnpq.fl_str_mv CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA::QUIMICA ORGANICA
description Sesquiterpene lactones represent an important group of secondary metabolites of the Asteraceae family. As the availability of natural sesquiterpene lactones is very limited, being many times insufficient for detailed studies of their bioactivity, the present investigation had as objective the synthesis of sesquiterpene lactones derivatives from α-santonin, aiming studies about the biological structure-activity relationship and the discovery of new compounds with potential herbicide activity. In this present work eleven compounds were synthesized [20]-[30], five among them are unknown. These compounds were prepared by different types of reactions including photochemistry, reduction, oxidation and esterification reactions. When α-santonin [9] was irradiated with high pressure mercury lamp, using anhydrous acetic acid as solvent in borosilicate reactor, 10α- acetoxy-3-oxo-1,7αH,6,11βH-guai-4-en-6,12-olide [20] was obtained, in 26% yield. Using acetic acid/water mixture 1:1 v/v, keeping the other conditions, the iso-foto-santonic acid [21] and the 10α-hydroxy-3-oxo-1,7αH,6,11βH-guai-4-en-6,12-olide [22] were obtained in 44% and 32% yields, respectively. When the α-santonine was submitted to the photochemistry reaction in a quartz reactor, using low pressure mercury lamp as source of ultraviolet radiation and acetonitrile as solvent, the lumisantonin [23] was produced in 83% yield. The compounds [20] and [22] were submitted to the reduction reaction with sodium borohydride, obtaining 10α-acetoxy-3β-hidroxy-1,7αH,6,11βH-guai-4-en-6,12-olide [28] and the 3β,10α-hydroxy-1,7αH,6,11βH-guai-4-en-6,12-olide [30] in 86% and 72% yields, respectively. To obtain 10α-acetoxy-3β-crotonoil-1,7αH,6,11βH-guai-4-en-6,12-olide [29] (63%), the compound [28] reacted with crotonoil chloride, in the presence of pyridine. The 3-oxo-7αH,6βH-eudesma-1,4,11-trien-6,12-olide [25] was obtained in 72% yield and, it was prepared by the initial reaction of the α-santonine with phenyl selenium chloride (PhSeCl) and subsequent oxidation with hydrogen peroxide (H2O2). Then, the lactone [25] was submitted to the photochemistry reaction in a quartz reactor, using anhydrous acetic acid as solvent, and the compounds 10α-acetoxy-3-oxo-1,7αH,6βH-guai-4,11-dien-6,12-olide [26] and 11,13 deidrolumisantonin [27] were obtained in 4,5% and 18% yields, respectively. The compounds [20] and [30] were submitted to biological assays to evaluate their activities on the germination and on the radicular growth of cucumber (Cucumis sativus) and sorghum plants (Sorghum bicolor x Sorghum sudanensis). Amongst all evaluated compounds, the compound [20] was the one that presented higher activity on the radicular growth of the cucumber and sorghum plantules, being inhibitions of 53,5% and 66,7% observed, respectively. Low or no significant inhibitory activity was observed on the germination of the cucumber and sorghum seeds.
publishDate 2007
dc.date.available.fl_str_mv 2007-07-23
2015-03-26T13:00:39Z
dc.date.issued.fl_str_mv 2007-02-16
dc.date.accessioned.fl_str_mv 2015-03-26T13:00:39Z
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
dc.type.driver.fl_str_mv info:eu-repo/semantics/masterThesis
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status_str publishedVersion
dc.identifier.citation.fl_str_mv ARANTES, Francisco Frederico Pelinson. Synthesis and evaluation of the phytotoxicity of new sesquiterpe lactones. 2007. 147 f. Dissertação (Mestrado em Agroquímica analítica; Agroquímica inorgânica e Físico-química; Agroquímica orgânica) - Universidade Federal de Viçosa, Viçosa, 2007.
dc.identifier.uri.fl_str_mv http://locus.ufv.br/handle/123456789/2167
identifier_str_mv ARANTES, Francisco Frederico Pelinson. Synthesis and evaluation of the phytotoxicity of new sesquiterpe lactones. 2007. 147 f. Dissertação (Mestrado em Agroquímica analítica; Agroquímica inorgânica e Físico-química; Agroquímica orgânica) - Universidade Federal de Viçosa, Viçosa, 2007.
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dc.publisher.country.fl_str_mv BR
dc.publisher.department.fl_str_mv Agroquímica analítica; Agroquímica inorgânica e Físico-química; Agroquímica orgânica
publisher.none.fl_str_mv Universidade Federal de Viçosa
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