Constituintes qu?micos e a atividade biol?gica de Eupatorium macrocephalum Less. (Aster?cea) e Annona dioica ST Hill. (Annon?ceae): uma contribui??o ao estudo de plantas medicinais no Paraguay
Autor(a) principal: | |
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Data de Publicação: | 2007 |
Tipo de documento: | Tese |
Idioma: | por |
Título da fonte: | Biblioteca Digital de Teses e Dissertações da UFRRJ |
Texto Completo: | https://tede.ufrrj.br/jspui/handle/tede/34 |
Resumo: | Eupatorium macrocephalum Less (Asteraceae) and Annona dioica (Annonaceae) are distributed throughout South America and have long been used as paraguayan folk medicine. The present work relates the chemical investigation of the extracts of Eupatorium macrocephalum Less (colleted in Dpto. Central-Paraguay) which resulted in the isolation and identification of twenty compounds: six triterpenoids; lupeol and lupeol acetate (the main chemical components), taraxasterol and taraxasterol acetate together with a- and b-amiryn; six steroids; stigmasterol, sitosterol, epinasterol, 3-O-b- D-glicopyranosylstigmasterol, 3-O-b-D-glicopyranosylepinasterol and 3-O-b-Dglicopyranosylsitosterol; one diterpenoid, -9,15-diidroxikauren-3-O-b-D-glicopiranosyl; one flavonoid, 3 ,4 ,5-triidroxi-6,7-dimetoxiflavone and six ?c. cynnamyc derivates. The methanolic extract from the leaves of Annona dioica specimens collected in the cerrado of Horqueta city (Dpto. Concepci?n-Paraguay) led to the isolation and identification of nine compounds: four flavonoids: kaempferol, 3-O-[3 ,6 -di-O-phydroxycynnamoyl]- b-galactopyranosyl-kaempferol, 6 -O-p-hydroxycinnamoil-b- galactopyranosyl-kaempferol and 3-O-b-galactopyranosyl-kaempferol. Three steroids, sitosterol, stigmasterol and 3-O-b-D-glicopyranosylsitosterol.The CHCl3 extract from the root furnished two acetogenines, one known as motrilin and a new isomer epimotriline. The structures were established using. IV, Mass and NMR spectral data, including 2D NMR experiments of natural substances or by the comparison of spectral and physical data with those described in the literature. Biological tests using the brine shrimp lethality test in Artemia salina Leach for screening with all extract revealed good activity so for A. dioica extracts. The cytotoxic effects of the flavonoids and flavonoidic fractions (FF) were evaluated by MTT (3-(4,5- dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) assay against Ehrlich carcinoma cells. The inhibitory action on DNA-topoisomerase I and II of all the flavonoids was evaluated by relaxation assays on pBR322 plasmid DNA. The obtained fractions of the metanolic extract of the roots were submitted the screening of activity antitumoral in vitro in lineages of cells human tumorais [MDAMB435, HCT8, HL60 and SF295]. The results showed activity of all of the fractions tested in at least one of the lineages used in the screening. |
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Braz Filho, Raimundo070.100.018-04http://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4783518E6Carvalho, M?rio Geraldo de257.152.327-91http://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4783195U9052.242.277-20http://lattes.cnpq.br/5744415641833528Vega, Maria Raquel Garcia2016-04-26T13:58:10Z2008-05-272007-03-19VEGA, Maria Raquel Garcia. Constituintes qu?micos e a atividade biol?gica de Eupatorium macrocephalum Less. (Aster?cea) e Annona dioica ST Hill. (Annon?ceae): uma contribui??o ao estudo de plantas medicinais no Paraguay. 2007. 109 f. Tese (Doutorado em Qu?mica Org?nica) - Instituto de Ci?ncias Exatas, Universidade Federal Rural do Rio de Janeiro, Serop?dica - RJ, 2007.https://tede.ufrrj.br/jspui/handle/tede/34Eupatorium macrocephalum Less (Asteraceae) and Annona dioica (Annonaceae) are distributed throughout South America and have long been used as paraguayan folk medicine. The present work relates the chemical investigation of the extracts of Eupatorium macrocephalum Less (colleted in Dpto. Central-Paraguay) which resulted in the isolation and identification of twenty compounds: six triterpenoids; lupeol and lupeol acetate (the main chemical components), taraxasterol and taraxasterol acetate together with a- and b-amiryn; six steroids; stigmasterol, sitosterol, epinasterol, 3-O-b- D-glicopyranosylstigmasterol, 3-O-b-D-glicopyranosylepinasterol and 3-O-b-Dglicopyranosylsitosterol; one diterpenoid, -9,15-diidroxikauren-3-O-b-D-glicopiranosyl; one flavonoid, 3 ,4 ,5-triidroxi-6,7-dimetoxiflavone and six ?c. cynnamyc derivates. The methanolic extract from the leaves of Annona dioica specimens collected in the cerrado of Horqueta city (Dpto. Concepci?n-Paraguay) led to the isolation and identification of nine compounds: four flavonoids: kaempferol, 3-O-[3 ,6 -di-O-phydroxycynnamoyl]- b-galactopyranosyl-kaempferol, 6 -O-p-hydroxycinnamoil-b- galactopyranosyl-kaempferol and 3-O-b-galactopyranosyl-kaempferol. Three steroids, sitosterol, stigmasterol and 3-O-b-D-glicopyranosylsitosterol.The CHCl3 extract from the root furnished two acetogenines, one known as motrilin and a new isomer epimotriline. The structures were established using. IV, Mass and NMR spectral data, including 2D NMR experiments of natural substances or by the comparison of spectral and physical data with those described in the literature. Biological tests using the brine shrimp lethality test in Artemia salina Leach for screening with all extract revealed good activity so for A. dioica extracts. The cytotoxic effects of the flavonoids and flavonoidic fractions (FF) were evaluated by MTT (3-(4,5- dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) assay against Ehrlich carcinoma cells. The inhibitory action on DNA-topoisomerase I and II of all the flavonoids was evaluated by relaxation assays on pBR322 plasmid DNA. The obtained fractions of the metanolic extract of the roots were submitted the screening of activity antitumoral in vitro in lineages of cells human tumorais [MDAMB435, HCT8, HL60 and SF295]. The results showed activity of all of the fractions tested in at least one of the lineages used in the screening.Eupatorium macrocephalum Less (Asteraceae) e Annona dioica (Annonaceae) s?o arbustos de grande dispers?o na Am?rica do Sul e largamente usados na medicina popular no Paraguai. O presente trabalho relata o estudo qu?mico de extratos de Eupatorium macrocephalum Less. (coletada no Dpto. Central Paraguay) que levou ao isolamento e identifica??o de vinte subst?ncias; seis triterpenos: acetato de lupeoila e lupeol (constituintes majorit?rios), taraxasterol e acetato de taraxasterila alem de a- e b- amirina; seis ester?ides: estigmasterol, sitosterol, epinasterol, 3-O-b-D-glicopiranosil estigmasterol, 3-O-b-D-glicopiranosil epinasterol e 3-O-b-D-glicopiranosil sitosterol; um diterpeno: (-) 9,15-diidroxicauran-19-ato de b-D-glicopiranosila; um flavon?ide: 3 ,4 ,5-triidroxi-6,7-dimetoxiflavona e seis derivados do ?cido cin?mico. Estudo qu?mico do extrato metan?lico das folhas de um esp?cime de Annona dioica coletada no cerrado de Horqueta (Dpto. de Concepci?n, Paraguay) conduziu ao isolamento e ? identifica??o de nove subst?ncias; quatro flavon?ides: canferol, 3-O- [3 ,6 -di-O-p-hidroxicinamoil]-b-galactopiranosil-canferol, 6 -O-p-hidroxicinamoil-b- D-galactopiranosil-canferol e 3-O-b-D-galactopiranosil-canferol; al?m da mistura de sitosterol + estigmasterol e do 3-O-b-D-glicopiranosil sitosterol. Do extrato em clorof?rmio das ra?zes obteve-se duas acetogeninas sendo uma delas in?dita na literatura. Todas as subst?ncias isoladas s?o descritas pela primeira vez para as respectivas esp?cies vegetais.As elucida??es estruturais basearam-se na an?lise de dados espectrom?tricos, principalmente RMN 1H e 13 C, uni e bidimensionais, alem de CGEM, EMAR e compara??o com dados da literatura.Foram realizados ensaios de toxidade frente a Artemia salina Leach com extratos das plantas em estudo. Os resultados mostraram atividade significativa apenas em extratos de A. di?ica. As fra??es obtidas a partir destes extratos e os flavon?ides isolados tiveram a atividade citot?xica avaliada utilizando-se c?lulas do carcinoma de Erhlich bem como avalia??o da inibi??o da enzima humana DNA-Topoissomerase I e II. As fra??es obtidas do extrato metan?lico das ra?zes foram submetidas a triagem de atividade antitumoral in vitro em linhagens de c?lulas tumorais humanas [MDA-MB435, HCT8, HL60 e SF295]. Os resultados mostraram atividade de todas as fra??es testadas em pelo menos uma das linhagens utilizadas na triagem.Made available in DSpace on 2016-04-26T13:58:10Z (GMT). No. of bitstreams: 1 2007 - Maria Raquel Garcia Vega.pdf: 9733903 bytes, checksum: e53bea53c44309442e243153d34107d6 (MD5) Previous issue date: 2007-03-19CNPq - Conselho Nacional de Desenvolvimento Cient?fico e Tecnol?gicoapplication/pdfhttps://tede.ufrrj.br/retrieve/3555/2007-%20Maria%20Raquel%20Garcia%20Vega.pdf.jpghttps://tede.ufrrj.br/retrieve/12244/2007%20-%20Maria%20Raquel%20Garcia%20Vega.pdf.jpghttps://tede.ufrrj.br/retrieve/17596/2007%20-%20Maria%20Raquel%20Garcia%20Vega.pdf.jpghttps://tede.ufrrj.br/retrieve/23936/2007%20-%20Maria%20Raquel%20Garcia%20Vega.pdf.jpghttps://tede.ufrrj.br/retrieve/30298/2007%20-%20Maria%20Raquel%20Garcia%20Vega.pdf.jpghttps://tede.ufrrj.br/retrieve/36640/2007%20-%20Maria%20Raquel%20Garcia%20Vega.pdf.jpghttps://tede.ufrrj.br/retrieve/43028/2007%20-%20Maria%20Raquel%20Garcia%20Vega.pdf.jpghttps://tede.ufrrj.br/retrieve/49424/2007%20-%20Maria%20Raquel%20Garcia%20Vega.pdf.jpghttps://tede.ufrrj.br/retrieve/55866/2007%20-%20Maria%20Raquel%20Garcia%20Vega.pdf.jpgporUniversidade Federal Rural do Rio de JaneiroPrograma de P?s-Gradua??o em Qu?micaUFRRJBrasilInstituto de Ci?ncias Exatasplantas medicinaisatividade biol?gicaEupatorium macrocephalumAnnona di?icaterpen?idesflavon?idesQu?micaConstituintes qu?micos e a atividade biol?gica de Eupatorium macrocephalum Less. (Aster?cea) e Annona dioica ST Hill. 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dc.title.por.fl_str_mv |
Constituintes qu?micos e a atividade biol?gica de Eupatorium macrocephalum Less. (Aster?cea) e Annona dioica ST Hill. (Annon?ceae): uma contribui??o ao estudo de plantas medicinais no Paraguay |
title |
Constituintes qu?micos e a atividade biol?gica de Eupatorium macrocephalum Less. (Aster?cea) e Annona dioica ST Hill. (Annon?ceae): uma contribui??o ao estudo de plantas medicinais no Paraguay |
spellingShingle |
Constituintes qu?micos e a atividade biol?gica de Eupatorium macrocephalum Less. (Aster?cea) e Annona dioica ST Hill. (Annon?ceae): uma contribui??o ao estudo de plantas medicinais no Paraguay Vega, Maria Raquel Garcia plantas medicinais atividade biol?gica Eupatorium macrocephalum Annona di?ica terpen?ides flavon?ides Qu?mica |
title_short |
Constituintes qu?micos e a atividade biol?gica de Eupatorium macrocephalum Less. (Aster?cea) e Annona dioica ST Hill. (Annon?ceae): uma contribui??o ao estudo de plantas medicinais no Paraguay |
title_full |
Constituintes qu?micos e a atividade biol?gica de Eupatorium macrocephalum Less. (Aster?cea) e Annona dioica ST Hill. (Annon?ceae): uma contribui??o ao estudo de plantas medicinais no Paraguay |
title_fullStr |
Constituintes qu?micos e a atividade biol?gica de Eupatorium macrocephalum Less. (Aster?cea) e Annona dioica ST Hill. (Annon?ceae): uma contribui??o ao estudo de plantas medicinais no Paraguay |
title_full_unstemmed |
Constituintes qu?micos e a atividade biol?gica de Eupatorium macrocephalum Less. (Aster?cea) e Annona dioica ST Hill. (Annon?ceae): uma contribui??o ao estudo de plantas medicinais no Paraguay |
title_sort |
Constituintes qu?micos e a atividade biol?gica de Eupatorium macrocephalum Less. (Aster?cea) e Annona dioica ST Hill. (Annon?ceae): uma contribui??o ao estudo de plantas medicinais no Paraguay |
author |
Vega, Maria Raquel Garcia |
author_facet |
Vega, Maria Raquel Garcia |
author_role |
author |
dc.contributor.advisor1.fl_str_mv |
Braz Filho, Raimundo |
dc.contributor.advisor1ID.fl_str_mv |
070.100.018-04 |
dc.contributor.advisor1Lattes.fl_str_mv |
http://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4783518E6 |
dc.contributor.advisor-co1.fl_str_mv |
Carvalho, M?rio Geraldo de |
dc.contributor.advisor-co1ID.fl_str_mv |
257.152.327-91 |
dc.contributor.advisor-co1Lattes.fl_str_mv |
http://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4783195U9 |
dc.contributor.authorID.fl_str_mv |
052.242.277-20 |
dc.contributor.authorLattes.fl_str_mv |
http://lattes.cnpq.br/5744415641833528 |
dc.contributor.author.fl_str_mv |
Vega, Maria Raquel Garcia |
contributor_str_mv |
Braz Filho, Raimundo Carvalho, M?rio Geraldo de |
dc.subject.por.fl_str_mv |
plantas medicinais atividade biol?gica Eupatorium macrocephalum Annona di?ica terpen?ides flavon?ides |
topic |
plantas medicinais atividade biol?gica Eupatorium macrocephalum Annona di?ica terpen?ides flavon?ides Qu?mica |
dc.subject.cnpq.fl_str_mv |
Qu?mica |
description |
Eupatorium macrocephalum Less (Asteraceae) and Annona dioica (Annonaceae) are distributed throughout South America and have long been used as paraguayan folk medicine. The present work relates the chemical investigation of the extracts of Eupatorium macrocephalum Less (colleted in Dpto. Central-Paraguay) which resulted in the isolation and identification of twenty compounds: six triterpenoids; lupeol and lupeol acetate (the main chemical components), taraxasterol and taraxasterol acetate together with a- and b-amiryn; six steroids; stigmasterol, sitosterol, epinasterol, 3-O-b- D-glicopyranosylstigmasterol, 3-O-b-D-glicopyranosylepinasterol and 3-O-b-Dglicopyranosylsitosterol; one diterpenoid, -9,15-diidroxikauren-3-O-b-D-glicopiranosyl; one flavonoid, 3 ,4 ,5-triidroxi-6,7-dimetoxiflavone and six ?c. cynnamyc derivates. The methanolic extract from the leaves of Annona dioica specimens collected in the cerrado of Horqueta city (Dpto. Concepci?n-Paraguay) led to the isolation and identification of nine compounds: four flavonoids: kaempferol, 3-O-[3 ,6 -di-O-phydroxycynnamoyl]- b-galactopyranosyl-kaempferol, 6 -O-p-hydroxycinnamoil-b- galactopyranosyl-kaempferol and 3-O-b-galactopyranosyl-kaempferol. Three steroids, sitosterol, stigmasterol and 3-O-b-D-glicopyranosylsitosterol.The CHCl3 extract from the root furnished two acetogenines, one known as motrilin and a new isomer epimotriline. The structures were established using. IV, Mass and NMR spectral data, including 2D NMR experiments of natural substances or by the comparison of spectral and physical data with those described in the literature. Biological tests using the brine shrimp lethality test in Artemia salina Leach for screening with all extract revealed good activity so for A. dioica extracts. The cytotoxic effects of the flavonoids and flavonoidic fractions (FF) were evaluated by MTT (3-(4,5- dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) assay against Ehrlich carcinoma cells. The inhibitory action on DNA-topoisomerase I and II of all the flavonoids was evaluated by relaxation assays on pBR322 plasmid DNA. The obtained fractions of the metanolic extract of the roots were submitted the screening of activity antitumoral in vitro in lineages of cells human tumorais [MDAMB435, HCT8, HL60 and SF295]. The results showed activity of all of the fractions tested in at least one of the lineages used in the screening. |
publishDate |
2007 |
dc.date.issued.fl_str_mv |
2007-03-19 |
dc.date.available.fl_str_mv |
2008-05-27 |
dc.date.accessioned.fl_str_mv |
2016-04-26T13:58:10Z |
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info:eu-repo/semantics/publishedVersion |
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info:eu-repo/semantics/doctoralThesis |
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VEGA, Maria Raquel Garcia. Constituintes qu?micos e a atividade biol?gica de Eupatorium macrocephalum Less. (Aster?cea) e Annona dioica ST Hill. (Annon?ceae): uma contribui??o ao estudo de plantas medicinais no Paraguay. 2007. 109 f. Tese (Doutorado em Qu?mica Org?nica) - Instituto de Ci?ncias Exatas, Universidade Federal Rural do Rio de Janeiro, Serop?dica - RJ, 2007. |
dc.identifier.uri.fl_str_mv |
https://tede.ufrrj.br/jspui/handle/tede/34 |
identifier_str_mv |
VEGA, Maria Raquel Garcia. Constituintes qu?micos e a atividade biol?gica de Eupatorium macrocephalum Less. (Aster?cea) e Annona dioica ST Hill. (Annon?ceae): uma contribui??o ao estudo de plantas medicinais no Paraguay. 2007. 109 f. Tese (Doutorado em Qu?mica Org?nica) - Instituto de Ci?ncias Exatas, Universidade Federal Rural do Rio de Janeiro, Serop?dica - RJ, 2007. |
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Universidade Federal Rural do Rio de Janeiro |
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UFRRJ |
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Instituto de Ci?ncias Exatas |
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Universidade Federal Rural do Rio de Janeiro |
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