Síntese e fitotoxicidade de ozonídeos substituídos derivados de 8-oxabiciclo[3.2.1]oct-6-en-3-onas

Detalhes bibliográficos
Autor(a) principal: Cusati, Raphael Campos
Data de Publicação: 2008
Tipo de documento: Dissertação
Idioma: por
Título da fonte: LOCUS Repositório Institucional da UFV
Texto Completo: http://locus.ufv.br/handle/123456789/2070
Resumo: Artemisinin is a sesquiterpene lactone isolated from the leaves of Artemisia annua L. It has been demonstrated that this lactone exhibits phytotoxic activity against various monocotyledonous and dicotyledonous species. The observed biological activity has been associated with the presence of the endoperoxide moiety in the structure of this compound. In the present investigation, a series of ozonides, possessing the endoperoxide moiety, was synthesized and evaluate in terms of their phytotoxic activities. The ozonides were prepared from substitutes 8-oxabicyclo[3.2.1]oct-6-en-3-ones, which were obtained via [4+3] cycloaddition between oxyallyl carbocations and pertinent furans. The carbocations, in turns, were generated in situ from the 2,7-dibromocycloheptanone, 2,4-dibromopentan-3-one e 3,5-dibromoheptan-4-one. Eigth ozonides were synthesizes namely ozonide of (1α,6α,2β,5β)- 12-oxatricyclo-[4.4.1.12,5]-dodec-3-en-11-one (50%), ozonide of 2-methyl-(1α,6α,2β,5β)-12-oxatricyclo- [4.4.1.12,5]-dodec-3-en-11-one (37%), ozonide of 2-ethyl- (1α,6α,2β,5β)-12-oxatricyclo-[4.4.1.12,5]-dodec-3-en-11- one (42%), ozonide of 2,3-dimethyl-(1α,6α,2β,5β)-12- oxatricyclo-[4.4.1.12,5]-dodec-3-en-11-one (28%), ozonide of 2,5-dimethyl-(1α,6α,2β,5β)-12-oxatricyclo-[4.4.1.12,5]- dodec-3-en-11-one (55%), ozonide of 2-acetyl-(1α, 6α, 2β, 5β)-12-oxatricyclo-[4.4.1.12,5]-dodec-3-en-11-one (24%), ozonide of 2,6,9 α,11 α-tetramethyl-12-oxatricyclo[6.3.1.03,8] dodec-2-en-10-one (92%) and ozonide of 9 α,11 α-diethyl-2,6-dimethyl-12-oxatricyclo[6.3.1.03,8]dodec-2- en-10-one (76%). The phytotoxic activity of the synthesized ozonides as well as the cycloadduct precursors, was evaluated against sorghum (Sorghum bicolor L.) and cucumber (Cucumis sativus L.), at 5.0 x 10-4 mol L-1. Among the oxabicyclos, the most phytotoxic substance was 2-acetyl- (1α, 6α, 2β, 5β)-12-oxatricyclo-[4.4.1.12,5]-dodec-3-en- 11-one, inhibiting the root growth of cucumber and sorghum by 82.1% and88.5%, respectively. Concerning the ozonides, the best result was achieved with compound ozonide of 2,3- dimethyl-(1α, 6α, 2β, 5β)-12-oxatricyclo-[4.4.1.12,5]-dodec- 3-en-11-one which inhibited root growth of cucumber and sorghum by 84.2% and 80.2%, respectively.
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spelling Cusati, Raphael Camposhttp://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4759334Z3Demuner, Antônio Jacintohttp://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4783217D3Barbosa, Luiz Claudio de Almeidahttp://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4781106J2Maltha, Célia Regina álvareshttp://lattes.cnpq.br/7346715444030145Teixeira, Róbson Ricardohttp://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4723796H8Silva, Antônio Alberto dahttp://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4787739T6Silva, Sílvia Ribeiro de Souza ehttp://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4766262P72015-03-26T13:00:12Z2009-07-032015-03-26T13:00:12Z2008-12-12CUSATI, Raphael Campos. Synthesis and phytotoxic activity of substitutes ozonides derivatives of the 8-oxabicyclo[3.2.1]oct-6-en-3-ones. 2008. 141 f. Dissertação (Mestrado em Agroquímica analítica; Agroquímica inorgânica e Físico-química; Agroquímica orgânica) - Universidade Federal de Viçosa, Viçosa, 2008.http://locus.ufv.br/handle/123456789/2070Artemisinin is a sesquiterpene lactone isolated from the leaves of Artemisia annua L. It has been demonstrated that this lactone exhibits phytotoxic activity against various monocotyledonous and dicotyledonous species. The observed biological activity has been associated with the presence of the endoperoxide moiety in the structure of this compound. In the present investigation, a series of ozonides, possessing the endoperoxide moiety, was synthesized and evaluate in terms of their phytotoxic activities. The ozonides were prepared from substitutes 8-oxabicyclo[3.2.1]oct-6-en-3-ones, which were obtained via [4+3] cycloaddition between oxyallyl carbocations and pertinent furans. The carbocations, in turns, were generated in situ from the 2,7-dibromocycloheptanone, 2,4-dibromopentan-3-one e 3,5-dibromoheptan-4-one. Eigth ozonides were synthesizes namely ozonide of (1α,6α,2β,5β)- 12-oxatricyclo-[4.4.1.12,5]-dodec-3-en-11-one (50%), ozonide of 2-methyl-(1α,6α,2β,5β)-12-oxatricyclo- [4.4.1.12,5]-dodec-3-en-11-one (37%), ozonide of 2-ethyl- (1α,6α,2β,5β)-12-oxatricyclo-[4.4.1.12,5]-dodec-3-en-11- one (42%), ozonide of 2,3-dimethyl-(1α,6α,2β,5β)-12- oxatricyclo-[4.4.1.12,5]-dodec-3-en-11-one (28%), ozonide of 2,5-dimethyl-(1α,6α,2β,5β)-12-oxatricyclo-[4.4.1.12,5]- dodec-3-en-11-one (55%), ozonide of 2-acetyl-(1α, 6α, 2β, 5β)-12-oxatricyclo-[4.4.1.12,5]-dodec-3-en-11-one (24%), ozonide of 2,6,9 α,11 α-tetramethyl-12-oxatricyclo[6.3.1.03,8] dodec-2-en-10-one (92%) and ozonide of 9 α,11 α-diethyl-2,6-dimethyl-12-oxatricyclo[6.3.1.03,8]dodec-2- en-10-one (76%). The phytotoxic activity of the synthesized ozonides as well as the cycloadduct precursors, was evaluated against sorghum (Sorghum bicolor L.) and cucumber (Cucumis sativus L.), at 5.0 x 10-4 mol L-1. Among the oxabicyclos, the most phytotoxic substance was 2-acetyl- (1α, 6α, 2β, 5β)-12-oxatricyclo-[4.4.1.12,5]-dodec-3-en- 11-one, inhibiting the root growth of cucumber and sorghum by 82.1% and88.5%, respectively. Concerning the ozonides, the best result was achieved with compound ozonide of 2,3- dimethyl-(1α, 6α, 2β, 5β)-12-oxatricyclo-[4.4.1.12,5]-dodec- 3-en-11-one which inhibited root growth of cucumber and sorghum by 84.2% and 80.2%, respectively.A artemisinina é uma lactona sesquiterpênica isolada das folhas de Artemisia annua L. Já foi demonstrado que essa lactona apresenta atividade fitotóxica contra várias espécies de plantas monocotiledôneas e dicotiledôneas. Essa atividade biológica observada tem sido associada à presença da ligação endoperóxido na estrutura desse composto. No presente trabalho, uma série de ozonídeos, possuindo a ligação endoperóxido, foi sintetizada e avaliada em termos de suas atividades fitotóxicas. Os ozonídeos foram preparados a partir de 8-oxabiciclo[3.2.1]oct-6-en-3-ona substituídos, que foram obtidos via reação de cicloadição [4+3] entre cátions oxialílicos e diferentes furanos. Os carbocátions, por sua vez, foram gerados in situ a partir da 2,7-dibromocicloeptanona, 2,4-dibromopentan-3-ona e 3,5-dibromoeptan-4-ona. Oito ozonídeos foram sintetizados: ozonídeo do (1α,6α,2β,5β)-12- oxatriciclo-[4.4.1.12,5]-dodec-3-en-11-ona (50%), ozonídeo do 2-metil-(1α,6α,2β,5β)-12-oxatriciclo-[4.4.1.12,5]-dodec- 3-en-11-ona (37%), ozonídeo do 2-etil-(1α,6α,2β,5β)-12- oxatriciclo-[4.4.1.12,5]-dodec-3-en-11-ona (42%), ozonídeo do 2,3-dimetil-(1α,6α,2β,5β)-12-oxatriciclo-[4.4.1.12,5]- dodec-3-en-11-ona (28%), ozonídeo do 2,5-dimetil- (1α,6α,2β,5β)-12-oxatriciclo-[4.4.1.12,5]-dodec-3-en-11- ona (55%), ozonídeo do 2-acetil-(1α,6α,2β,5β)-12-oxatriciclo- [4.4.1.12,5]-dodec-3-en-11-ona (24%), ozonídeo do 2,6,9 α,11 α-tetrametil-12-oxatriciclo[6.3.1.03,8]dodec-2-en-10- ona (92%) e ozonídeo do 9 α,11 α-dietil-2,6-dimetil-12- oxatriciclo[6.3.1.03,8]dodec-2-en-10-ona (76%). A potencial fitotoxicidade dos ozonídeos sintetizados, bem como dos cicloadutos que deram origem a estes ozonídeos, foram avaliadas no tocante a habilidade desses inibirem a germinação de sementes, o crescimento radicular, e da parte aérea de plântulas de sorgo (Sorghum bicolor L.) e de pepino (Cucumis sativus L.), na concentração de 5,0 x 10-4 mol L-1. Entre os oxabiciclos, o composto que apresentou maior fitotoxicidade foi a 2-acetil-(1α,6α,2β,5β)-12-oxatriciclo- [4.4.1.12,5]-dodec-3-en-11-ona, inibindo o crescimento radicular de pepino e sorgo em 82,1 e 88,5%, respectivamente. Entre os ozonídeos, a maior atividade fitotóxica foi provocada pelo ozonídeo do 2,3-dimetil- (1α,6α,2β,5β)-12-oxatriciclo-[4.4.1.12,5]-dodec-3-en-11-ona que inibiu o crescimento de plântulas de pepino em 84,2% e de sorgo em 80,2%.Fundação de Amparo a Pesquisa do Estado de Minas Geraisapplication/pdfporUniversidade Federal de ViçosaMestrado em AgroquímicaUFVBRAgroquímica analítica; Agroquímica inorgânica e Físico-química; Agroquímica orgânicaCátion oxialílicoCicloadição [4+3]OzonídeosFitotoxicidadeOxyallyl carbocations[4+3] cycloaditionOzonidesPhytotoxicityCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA::QUIMICA ANALITICASíntese e fitotoxicidade de ozonídeos substituídos derivados de 8-oxabiciclo[3.2.1]oct-6-en-3-onasSynthesis and phytotoxic activity of substitutes ozonides derivatives of the 8-oxabicyclo[3.2.1]oct-6-en-3-onesinfo: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/pdf3156987https://locus.ufv.br//bitstream/123456789/2070/1/texto%20completo.pdfd026e3b8caf2e996493c2490943c6070MD51TEXTtexto completo.pdf.txttexto completo.pdf.txtExtracted texttext/plain149905https://locus.ufv.br//bitstream/123456789/2070/2/texto%20completo.pdf.txt5aebfe2041434ad3e4b4bb6398000490MD52THUMBNAILtexto completo.pdf.jpgtexto completo.pdf.jpgIM Thumbnailimage/jpeg3594https://locus.ufv.br//bitstream/123456789/2070/3/texto%20completo.pdf.jpg82e36d3b5bd2ead24dc7675092699d0eMD53123456789/20702016-04-07 23:20:30.173oai:locus.ufv.br:123456789/2070Repositório InstitucionalPUBhttps://www.locus.ufv.br/oai/requestfabiojreis@ufv.bropendoar:21452016-04-08T02:20:30LOCUS Repositório Institucional da UFV - Universidade Federal de Viçosa (UFV)false
dc.title.por.fl_str_mv Síntese e fitotoxicidade de ozonídeos substituídos derivados de 8-oxabiciclo[3.2.1]oct-6-en-3-onas
dc.title.alternative.eng.fl_str_mv Synthesis and phytotoxic activity of substitutes ozonides derivatives of the 8-oxabicyclo[3.2.1]oct-6-en-3-ones
title Síntese e fitotoxicidade de ozonídeos substituídos derivados de 8-oxabiciclo[3.2.1]oct-6-en-3-onas
spellingShingle Síntese e fitotoxicidade de ozonídeos substituídos derivados de 8-oxabiciclo[3.2.1]oct-6-en-3-onas
Cusati, Raphael Campos
Cátion oxialílico
Cicloadição [4+3]
Ozonídeos
Fitotoxicidade
Oxyallyl carbocations
[4+3] cycloadition
Ozonides
Phytotoxicity
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA::QUIMICA ANALITICA
title_short Síntese e fitotoxicidade de ozonídeos substituídos derivados de 8-oxabiciclo[3.2.1]oct-6-en-3-onas
title_full Síntese e fitotoxicidade de ozonídeos substituídos derivados de 8-oxabiciclo[3.2.1]oct-6-en-3-onas
title_fullStr Síntese e fitotoxicidade de ozonídeos substituídos derivados de 8-oxabiciclo[3.2.1]oct-6-en-3-onas
title_full_unstemmed Síntese e fitotoxicidade de ozonídeos substituídos derivados de 8-oxabiciclo[3.2.1]oct-6-en-3-onas
title_sort Síntese e fitotoxicidade de ozonídeos substituídos derivados de 8-oxabiciclo[3.2.1]oct-6-en-3-onas
author Cusati, Raphael Campos
author_facet Cusati, Raphael Campos
author_role author
dc.contributor.authorLattes.por.fl_str_mv http://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4759334Z3
dc.contributor.author.fl_str_mv Cusati, Raphael Campos
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.advisor-co2.fl_str_mv Barbosa, Luiz Claudio de Almeida
dc.contributor.advisor-co2Lattes.fl_str_mv http://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4781106J2
dc.contributor.advisor1.fl_str_mv Maltha, Célia Regina álvares
dc.contributor.advisor1Lattes.fl_str_mv http://lattes.cnpq.br/7346715444030145
dc.contributor.referee1.fl_str_mv Teixeira, Róbson Ricardo
dc.contributor.referee1Lattes.fl_str_mv http://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4723796H8
dc.contributor.referee2.fl_str_mv Silva, Antônio Alberto da
dc.contributor.referee2Lattes.fl_str_mv http://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4787739T6
dc.contributor.referee3.fl_str_mv Silva, Sílvia Ribeiro de Souza e
dc.contributor.referee3Lattes.fl_str_mv http://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4766262P7
contributor_str_mv Demuner, Antônio Jacinto
Barbosa, Luiz Claudio de Almeida
Maltha, Célia Regina álvares
Teixeira, Róbson Ricardo
Silva, Antônio Alberto da
Silva, Sílvia Ribeiro de Souza e
dc.subject.por.fl_str_mv Cátion oxialílico
Cicloadição [4+3]
Ozonídeos
Fitotoxicidade
topic Cátion oxialílico
Cicloadição [4+3]
Ozonídeos
Fitotoxicidade
Oxyallyl carbocations
[4+3] cycloadition
Ozonides
Phytotoxicity
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA::QUIMICA ANALITICA
dc.subject.eng.fl_str_mv Oxyallyl carbocations
[4+3] cycloadition
Ozonides
Phytotoxicity
dc.subject.cnpq.fl_str_mv CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA::QUIMICA ANALITICA
description Artemisinin is a sesquiterpene lactone isolated from the leaves of Artemisia annua L. It has been demonstrated that this lactone exhibits phytotoxic activity against various monocotyledonous and dicotyledonous species. The observed biological activity has been associated with the presence of the endoperoxide moiety in the structure of this compound. In the present investigation, a series of ozonides, possessing the endoperoxide moiety, was synthesized and evaluate in terms of their phytotoxic activities. The ozonides were prepared from substitutes 8-oxabicyclo[3.2.1]oct-6-en-3-ones, which were obtained via [4+3] cycloaddition between oxyallyl carbocations and pertinent furans. The carbocations, in turns, were generated in situ from the 2,7-dibromocycloheptanone, 2,4-dibromopentan-3-one e 3,5-dibromoheptan-4-one. Eigth ozonides were synthesizes namely ozonide of (1α,6α,2β,5β)- 12-oxatricyclo-[4.4.1.12,5]-dodec-3-en-11-one (50%), ozonide of 2-methyl-(1α,6α,2β,5β)-12-oxatricyclo- [4.4.1.12,5]-dodec-3-en-11-one (37%), ozonide of 2-ethyl- (1α,6α,2β,5β)-12-oxatricyclo-[4.4.1.12,5]-dodec-3-en-11- one (42%), ozonide of 2,3-dimethyl-(1α,6α,2β,5β)-12- oxatricyclo-[4.4.1.12,5]-dodec-3-en-11-one (28%), ozonide of 2,5-dimethyl-(1α,6α,2β,5β)-12-oxatricyclo-[4.4.1.12,5]- dodec-3-en-11-one (55%), ozonide of 2-acetyl-(1α, 6α, 2β, 5β)-12-oxatricyclo-[4.4.1.12,5]-dodec-3-en-11-one (24%), ozonide of 2,6,9 α,11 α-tetramethyl-12-oxatricyclo[6.3.1.03,8] dodec-2-en-10-one (92%) and ozonide of 9 α,11 α-diethyl-2,6-dimethyl-12-oxatricyclo[6.3.1.03,8]dodec-2- en-10-one (76%). The phytotoxic activity of the synthesized ozonides as well as the cycloadduct precursors, was evaluated against sorghum (Sorghum bicolor L.) and cucumber (Cucumis sativus L.), at 5.0 x 10-4 mol L-1. Among the oxabicyclos, the most phytotoxic substance was 2-acetyl- (1α, 6α, 2β, 5β)-12-oxatricyclo-[4.4.1.12,5]-dodec-3-en- 11-one, inhibiting the root growth of cucumber and sorghum by 82.1% and88.5%, respectively. Concerning the ozonides, the best result was achieved with compound ozonide of 2,3- dimethyl-(1α, 6α, 2β, 5β)-12-oxatricyclo-[4.4.1.12,5]-dodec- 3-en-11-one which inhibited root growth of cucumber and sorghum by 84.2% and 80.2%, respectively.
publishDate 2008
dc.date.issued.fl_str_mv 2008-12-12
dc.date.available.fl_str_mv 2009-07-03
2015-03-26T13:00:12Z
dc.date.accessioned.fl_str_mv 2015-03-26T13:00:12Z
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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dc.identifier.citation.fl_str_mv CUSATI, Raphael Campos. Synthesis and phytotoxic activity of substitutes ozonides derivatives of the 8-oxabicyclo[3.2.1]oct-6-en-3-ones. 2008. 141 f. Dissertação (Mestrado em Agroquímica analítica; Agroquímica inorgânica e Físico-química; Agroquímica orgânica) - Universidade Federal de Viçosa, Viçosa, 2008.
dc.identifier.uri.fl_str_mv http://locus.ufv.br/handle/123456789/2070
identifier_str_mv CUSATI, Raphael Campos. Synthesis and phytotoxic activity of substitutes ozonides derivatives of the 8-oxabicyclo[3.2.1]oct-6-en-3-ones. 2008. 141 f. Dissertação (Mestrado em Agroquímica analítica; Agroquímica inorgânica e Físico-química; Agroquímica orgânica) - Universidade Federal de Viçosa, Viçosa, 2008.
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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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