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

Detalhes bibliográficos
Autor(a) principal: Vega, Maria Raquel Garcia
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.
id UFRRJ-1_25b104f7492de374041fd50a4bcc2b05
oai_identifier_str oai:localhost:tede/34
network_acronym_str UFRRJ-1
network_name_str Biblioteca Digital de Teses e Dissertações da UFRRJ
repository_id_str
spelling 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. (Annon?ceae): uma contribui??o ao estudo de plantas medicinais no Paraguayinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/doctoralThesisinfo:eu-repo/semantics/openAccessreponame:Biblioteca Digital de Teses e Dissertações da UFRRJinstname:Universidade Federal Rural do Rio de Janeiro (UFRRJ)instacron:UFRRJTHUMBNAIL2007 - Maria Raquel Garcia Vega.pdf.jpg2007 - Maria Raquel Garcia Vega.pdf.jpgimage/jpeg4674http://localhost:8080/tede/bitstream/tede/34/20/2007+-+Maria+Raquel+Garcia+Vega.pdf.jpgb39a26471a1c62f3bb40e165683019dfMD520TEXT2007 - Maria Raquel Garcia Vega.pdf.txt2007 - Maria Raquel Garcia Vega.pdf.txttext/plain96611http://localhost:8080/tede/bitstream/tede/34/19/2007+-+Maria+Raquel+Garcia+Vega.pdf.txt933c6ae04b28a58a559e97fce207cff4MD519ORIGINAL2007 - Maria Raquel Garcia Vega.pdf2007 - Maria Raquel Garcia Vega.pdfapplication/pdf2893008http://localhost:8080/tede/bitstream/tede/34/4/2007+-+Maria+Raquel+Garcia+Vega.pdfd5e4db4242d2c4b814bf62f96afb17bcMD54tede/342022-06-13 11:19:40.733oai:localhost:tede/34Biblioteca Digital de Teses e Dissertaçõeshttps://tede.ufrrj.br/PUBhttps://tede.ufrrj.br/oai/requestbibliot@ufrrj.br||bibliot@ufrrj.bropendoar:2022-06-13T14:19:40Biblioteca Digital de Teses e Dissertações da UFRRJ - Universidade Federal Rural do Rio de Janeiro (UFRRJ)false
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
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
dc.type.driver.fl_str_mv info:eu-repo/semantics/doctoralThesis
format doctoralThesis
status_str publishedVersion
dc.identifier.citation.fl_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.
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.
url https://tede.ufrrj.br/jspui/handle/tede/34
dc.language.iso.fl_str_mv por
language por
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv Universidade Federal Rural do Rio de Janeiro
dc.publisher.program.fl_str_mv Programa de P?s-Gradua??o em Qu?mica
dc.publisher.initials.fl_str_mv UFRRJ
dc.publisher.country.fl_str_mv Brasil
dc.publisher.department.fl_str_mv Instituto de Ci?ncias Exatas
publisher.none.fl_str_mv Universidade Federal Rural do Rio de Janeiro
dc.source.none.fl_str_mv reponame:Biblioteca Digital de Teses e Dissertações da UFRRJ
instname:Universidade Federal Rural do Rio de Janeiro (UFRRJ)
instacron:UFRRJ
instname_str Universidade Federal Rural do Rio de Janeiro (UFRRJ)
instacron_str UFRRJ
institution UFRRJ
reponame_str Biblioteca Digital de Teses e Dissertações da UFRRJ
collection Biblioteca Digital de Teses e Dissertações da UFRRJ
bitstream.url.fl_str_mv http://localhost:8080/tede/bitstream/tede/34/20/2007+-+Maria+Raquel+Garcia+Vega.pdf.jpg
http://localhost:8080/tede/bitstream/tede/34/19/2007+-+Maria+Raquel+Garcia+Vega.pdf.txt
http://localhost:8080/tede/bitstream/tede/34/4/2007+-+Maria+Raquel+Garcia+Vega.pdf
bitstream.checksum.fl_str_mv b39a26471a1c62f3bb40e165683019df
933c6ae04b28a58a559e97fce207cff4
d5e4db4242d2c4b814bf62f96afb17bc
bitstream.checksumAlgorithm.fl_str_mv MD5
MD5
MD5
repository.name.fl_str_mv Biblioteca Digital de Teses e Dissertações da UFRRJ - Universidade Federal Rural do Rio de Janeiro (UFRRJ)
repository.mail.fl_str_mv bibliot@ufrrj.br||bibliot@ufrrj.br
_version_ 1800313449000992768