Alcalóides de Rutaceae: química e atividade biológica.

Detalhes bibliográficos
Autor(a) principal: Andrade, Márcio Roberto de
Data de Publicação: 2003
Tipo de documento: Tese
Idioma: por
Título da fonte: Repositório Institucional da UFSCAR
Texto Completo: https://repositorio.ufscar.br/handle/ufscar/6368
Resumo: This work describes the phytochemical study of two plant species Galipea bracteata and Ravenia infelix belonging to the family Rutaceae, aiming the isolation and structure determination of componds from leaves and branches of these plants. This work is also directed to the search of trypanocidal and leishmanicidal compounds from these plants. The following models were used to check the biological activities of the isolated compounds: antiparasitc activity - trypomastigote form of Trypanosoma cruzi in vitro , enzymatic inhibitory activity on gGAPDH (Glyceraldeyde 3- phosphate dehidrogenase) of T. cruzi and enzymatic inhibitory activity on APRT (Adheninephosphoribosyl- transferase) of Leishmania tarentolae. The leaves extract of G. bracteata afforded tirtheen quinoline alkaloids. Among these compounds seven have been described for the first time: 2-(3 ,4 -methylenedioxyphenylethyl)quinoline, 4- methoxy-2-(propan-1 -ona)quinoline (inedit), 4-methoxy-2-(1 ,2 -transepoxypentyl) quinoline (inedit), 4-methoxy-2-n-heptylquinoline, 2-(1 ,2 -transepoxypentyl) quinoline (inedit), 4-methoxy-2-(3 ,4 - methylenedioxyphenylethyl)quinoline, 4-methoxy-2-(1 ,2 -trans-epoxypropyl)quinoline (inedit), 4-methoxy-2-n-propylquinoline, 2-n-pentylquinoline, 2-(propan-1 - one)quinoline (inedit), 4-methoxy-2-(pentan-1 -one)quinoline (inedit), 2-(pentan-1 - one)quinoline (inedit), a mixture of steroids campesterol, stigmasterol and sitosterol, one furoquinoline alkaloid evolitrine, a mixture of seco-furoquinoline alkaloids Edimethylrhoifolinate and Z-dimethylrhoifolinate, a pentacylclic triterpene arborinol and norsesquiterpene 3,5-dihydromegastigma-6,7-diene-9-one. From the branches of R. Infelix were isolated the carbazole alkaloids: 3-methylcarbazole and girinimbin, the steroids: 7-oxo-stigmasterol and 7-oxo-sitosterol, the indol 3-carboxaldeheide and mixtures of amides: N-trans and N-cis-feruloyltyramine, and N-trans and-cis-pcumaroyltyramine. The pure compounds had their trypanocidal and leishmanicidal activities determined.
id SCAR_e3fcb05b572e30a78ca4ecf2cfc80e06
oai_identifier_str oai:repositorio.ufscar.br:ufscar/6368
network_acronym_str SCAR
network_name_str Repositório Institucional da UFSCAR
repository_id_str 4322
spelling Andrade, Márcio Roberto deVieira, Paulo Cezarhttp://genos.cnpq.br:12010/dwlattes/owa/prc_imp_cv_int?f_cod=K4781745U2http://genos.cnpq.br:12010/dwlattes/owa/prc_imp_cv_int?f_cod=K4796035T5a151c0a8-d7f0-4946-8860-4cc88a3a2a652016-06-02T20:35:09Z2005-01-312016-06-02T20:35:09Z2003-11-18ANDRADE, Márcio Roberto de. Alkaloids of rutaceae: chemistry and biological activity.. 2003. 216 f. Tese (Doutorado em Ciências Exatas e da Terra) - Universidade Federal de São Carlos, São Carlos, 2003.https://repositorio.ufscar.br/handle/ufscar/6368This work describes the phytochemical study of two plant species Galipea bracteata and Ravenia infelix belonging to the family Rutaceae, aiming the isolation and structure determination of componds from leaves and branches of these plants. This work is also directed to the search of trypanocidal and leishmanicidal compounds from these plants. The following models were used to check the biological activities of the isolated compounds: antiparasitc activity - trypomastigote form of Trypanosoma cruzi in vitro , enzymatic inhibitory activity on gGAPDH (Glyceraldeyde 3- phosphate dehidrogenase) of T. cruzi and enzymatic inhibitory activity on APRT (Adheninephosphoribosyl- transferase) of Leishmania tarentolae. The leaves extract of G. bracteata afforded tirtheen quinoline alkaloids. Among these compounds seven have been described for the first time: 2-(3 ,4 -methylenedioxyphenylethyl)quinoline, 4- methoxy-2-(propan-1 -ona)quinoline (inedit), 4-methoxy-2-(1 ,2 -transepoxypentyl) quinoline (inedit), 4-methoxy-2-n-heptylquinoline, 2-(1 ,2 -transepoxypentyl) quinoline (inedit), 4-methoxy-2-(3 ,4 - methylenedioxyphenylethyl)quinoline, 4-methoxy-2-(1 ,2 -trans-epoxypropyl)quinoline (inedit), 4-methoxy-2-n-propylquinoline, 2-n-pentylquinoline, 2-(propan-1 - one)quinoline (inedit), 4-methoxy-2-(pentan-1 -one)quinoline (inedit), 2-(pentan-1 - one)quinoline (inedit), a mixture of steroids campesterol, stigmasterol and sitosterol, one furoquinoline alkaloid evolitrine, a mixture of seco-furoquinoline alkaloids Edimethylrhoifolinate and Z-dimethylrhoifolinate, a pentacylclic triterpene arborinol and norsesquiterpene 3,5-dihydromegastigma-6,7-diene-9-one. From the branches of R. Infelix were isolated the carbazole alkaloids: 3-methylcarbazole and girinimbin, the steroids: 7-oxo-stigmasterol and 7-oxo-sitosterol, the indol 3-carboxaldeheide and mixtures of amides: N-trans and N-cis-feruloyltyramine, and N-trans and-cis-pcumaroyltyramine. The pure compounds had their trypanocidal and leishmanicidal activities determined.O presente trabalho descreve o estudo fitoquímico de duas espécies de plantas pertencentes à família Rutaceae, no intuito de elucidar estruturas de micromoléculas presentes nas folhas e galhos. O estudo de Galipea bracteata e Ravenia infelix (Rutaceae) está também associado à busca de metabólitos com atividades tripanocida e leishmanicida, através dos seguintes modelos experimentais selecionados para verificação da atividade biológica: atividade antiparasitária forma tripomastigota de Trypanosoma cruzi in vitro , inibição enzimática in vitro (gGAPDH - Gliceraldeído- 3-fosfato-desidrogenase de T. cruzi) e inibição enzimática in vitro (APRT Adenina-fosforribosil-transferase de Leishmania tarantolae). Dos extratos das folhas de Galipea bracteata foram isolados treze alcalóides quinolínicos, dentre estas substâncias sete estão sendo descritas pela primeira vez: 2-(3 ,4 - metilenodioxifeniletil)quinolina, 4-metoxi-2-(propan-1 -ona)quinolina (inédita), 4- metoxi-2-(1 ,2 -trans-epoxipentil)quinolina (inédita), 4-metoxi-2-n-pentilquinolina, 4-metoxi-2-n-heptilquinolina, 2-(1 ,2 -trans-epoxipentil)quinolina (inédita), 4-metoxi-2- (3 ,4 -metilenodioxifeniletil)quinolina, 4-metoxi-2-(1 ,2 -trans-epoxipropil)quinolina (inédita), 4-metoxi-2-n-propilquinolina, 2-n-pentilquinolina, 2-(propan-1 - ona)quinolina (inédita), 4-metoxi-2-(pentan-1 -ona)quinolina (inédita), 2-(pentan-1 - ona)quinolina (inédita), mistura dos esteróides campesterol, estigmasterol e β- sitosterol, um alcalóide furoquinolínico evolitrina, uma mistura de alcalóides seco furoquinolínicos E e Z-rhoifolinato de dimetila, o triterpeno pentacíclico arborinol e o norsesquiterpeno 3,5-diidromegastigma-6,7-dieno-9-ona. Dos galhos de R. infelix foram isolados os alcalóides carbazóis: 3-metilcarbazol e girinimbina, os esteróides: 7-oxo-estigmasterol e 7-oxo-β-sitosterol, o indol: indol-3-carboxaldeído e misturas das amidas N-trans e N-cis-feruloiltiramina e N-trans-p e N-cis-p-cumaroiltiramina. Estas substâncias puras foram submetidas a testes para verificação das atividades tripanocida e leishmanicida.Universidade Federal de Sao Carlosapplication/pdfporUniversidade Federal de São CarlosPrograma de Pós-Graduação em Química - PPGQUFSCarBRQuímica orgânicaRutaceaeAlcalóidesGalipea bracteataRavenia infelixCIENCIAS EXATAS E DA TERRA::QUIMICA::QUIMICA ORGANICAAlcalóides de Rutaceae: química e atividade biológica.Alkaloids of rutaceae: chemistry and biological activity.info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/doctoralThesis-1-174f71c3f-154a-42a0-9eaa-a32f1f60d4c4info:eu-repo/semantics/openAccessreponame:Repositório Institucional da UFSCARinstname:Universidade Federal de São Carlos (UFSCAR)instacron:UFSCARORIGINALTeseMRA.pdfapplication/pdf5275801https://repositorio.ufscar.br/bitstream/ufscar/6368/1/TeseMRA.pdf8e03e586571c9a0adab0d1525691c66aMD51THUMBNAILTeseMRA.pdf.jpgTeseMRA.pdf.jpgIM Thumbnailimage/jpeg9574https://repositorio.ufscar.br/bitstream/ufscar/6368/2/TeseMRA.pdf.jpgbe484eb95f39f46eb03adaa8a78b48f0MD52ufscar/63682023-09-18 18:31:11.182oai:repositorio.ufscar.br:ufscar/6368Repositório InstitucionalPUBhttps://repositorio.ufscar.br/oai/requestopendoar:43222023-09-18T18:31:11Repositório Institucional da UFSCAR - Universidade Federal de São Carlos (UFSCAR)false
dc.title.por.fl_str_mv Alcalóides de Rutaceae: química e atividade biológica.
dc.title.alternative.eng.fl_str_mv Alkaloids of rutaceae: chemistry and biological activity.
title Alcalóides de Rutaceae: química e atividade biológica.
spellingShingle Alcalóides de Rutaceae: química e atividade biológica.
Andrade, Márcio Roberto de
Química orgânica
Rutaceae
Alcalóides
Galipea bracteata
Ravenia infelix
CIENCIAS EXATAS E DA TERRA::QUIMICA::QUIMICA ORGANICA
title_short Alcalóides de Rutaceae: química e atividade biológica.
title_full Alcalóides de Rutaceae: química e atividade biológica.
title_fullStr Alcalóides de Rutaceae: química e atividade biológica.
title_full_unstemmed Alcalóides de Rutaceae: química e atividade biológica.
title_sort Alcalóides de Rutaceae: química e atividade biológica.
author Andrade, Márcio Roberto de
author_facet Andrade, Márcio Roberto de
author_role author
dc.contributor.authorlattes.por.fl_str_mv http://genos.cnpq.br:12010/dwlattes/owa/prc_imp_cv_int?f_cod=K4796035T5
dc.contributor.author.fl_str_mv Andrade, Márcio Roberto de
dc.contributor.advisor1.fl_str_mv Vieira, Paulo Cezar
dc.contributor.advisor1Lattes.fl_str_mv http://genos.cnpq.br:12010/dwlattes/owa/prc_imp_cv_int?f_cod=K4781745U2
dc.contributor.authorID.fl_str_mv a151c0a8-d7f0-4946-8860-4cc88a3a2a65
contributor_str_mv Vieira, Paulo Cezar
dc.subject.por.fl_str_mv Química orgânica
Rutaceae
Alcalóides
Galipea bracteata
Ravenia infelix
topic Química orgânica
Rutaceae
Alcalóides
Galipea bracteata
Ravenia infelix
CIENCIAS EXATAS E DA TERRA::QUIMICA::QUIMICA ORGANICA
dc.subject.cnpq.fl_str_mv CIENCIAS EXATAS E DA TERRA::QUIMICA::QUIMICA ORGANICA
description This work describes the phytochemical study of two plant species Galipea bracteata and Ravenia infelix belonging to the family Rutaceae, aiming the isolation and structure determination of componds from leaves and branches of these plants. This work is also directed to the search of trypanocidal and leishmanicidal compounds from these plants. The following models were used to check the biological activities of the isolated compounds: antiparasitc activity - trypomastigote form of Trypanosoma cruzi in vitro , enzymatic inhibitory activity on gGAPDH (Glyceraldeyde 3- phosphate dehidrogenase) of T. cruzi and enzymatic inhibitory activity on APRT (Adheninephosphoribosyl- transferase) of Leishmania tarentolae. The leaves extract of G. bracteata afforded tirtheen quinoline alkaloids. Among these compounds seven have been described for the first time: 2-(3 ,4 -methylenedioxyphenylethyl)quinoline, 4- methoxy-2-(propan-1 -ona)quinoline (inedit), 4-methoxy-2-(1 ,2 -transepoxypentyl) quinoline (inedit), 4-methoxy-2-n-heptylquinoline, 2-(1 ,2 -transepoxypentyl) quinoline (inedit), 4-methoxy-2-(3 ,4 - methylenedioxyphenylethyl)quinoline, 4-methoxy-2-(1 ,2 -trans-epoxypropyl)quinoline (inedit), 4-methoxy-2-n-propylquinoline, 2-n-pentylquinoline, 2-(propan-1 - one)quinoline (inedit), 4-methoxy-2-(pentan-1 -one)quinoline (inedit), 2-(pentan-1 - one)quinoline (inedit), a mixture of steroids campesterol, stigmasterol and sitosterol, one furoquinoline alkaloid evolitrine, a mixture of seco-furoquinoline alkaloids Edimethylrhoifolinate and Z-dimethylrhoifolinate, a pentacylclic triterpene arborinol and norsesquiterpene 3,5-dihydromegastigma-6,7-diene-9-one. From the branches of R. Infelix were isolated the carbazole alkaloids: 3-methylcarbazole and girinimbin, the steroids: 7-oxo-stigmasterol and 7-oxo-sitosterol, the indol 3-carboxaldeheide and mixtures of amides: N-trans and N-cis-feruloyltyramine, and N-trans and-cis-pcumaroyltyramine. The pure compounds had their trypanocidal and leishmanicidal activities determined.
publishDate 2003
dc.date.issued.fl_str_mv 2003-11-18
dc.date.available.fl_str_mv 2005-01-31
2016-06-02T20:35:09Z
dc.date.accessioned.fl_str_mv 2016-06-02T20:35:09Z
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 ANDRADE, Márcio Roberto de. Alkaloids of rutaceae: chemistry and biological activity.. 2003. 216 f. Tese (Doutorado em Ciências Exatas e da Terra) - Universidade Federal de São Carlos, São Carlos, 2003.
dc.identifier.uri.fl_str_mv https://repositorio.ufscar.br/handle/ufscar/6368
identifier_str_mv ANDRADE, Márcio Roberto de. Alkaloids of rutaceae: chemistry and biological activity.. 2003. 216 f. Tese (Doutorado em Ciências Exatas e da Terra) - Universidade Federal de São Carlos, São Carlos, 2003.
url https://repositorio.ufscar.br/handle/ufscar/6368
dc.language.iso.fl_str_mv por
language por
dc.relation.confidence.fl_str_mv -1
-1
dc.relation.authority.fl_str_mv 74f71c3f-154a-42a0-9eaa-a32f1f60d4c4
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 de São Carlos
dc.publisher.program.fl_str_mv Programa de Pós-Graduação em Química - PPGQ
dc.publisher.initials.fl_str_mv UFSCar
dc.publisher.country.fl_str_mv BR
publisher.none.fl_str_mv Universidade Federal de São Carlos
dc.source.none.fl_str_mv reponame:Repositório Institucional da UFSCAR
instname:Universidade Federal de São Carlos (UFSCAR)
instacron:UFSCAR
instname_str Universidade Federal de São Carlos (UFSCAR)
instacron_str UFSCAR
institution UFSCAR
reponame_str Repositório Institucional da UFSCAR
collection Repositório Institucional da UFSCAR
bitstream.url.fl_str_mv https://repositorio.ufscar.br/bitstream/ufscar/6368/1/TeseMRA.pdf
https://repositorio.ufscar.br/bitstream/ufscar/6368/2/TeseMRA.pdf.jpg
bitstream.checksum.fl_str_mv 8e03e586571c9a0adab0d1525691c66a
be484eb95f39f46eb03adaa8a78b48f0
bitstream.checksumAlgorithm.fl_str_mv MD5
MD5
repository.name.fl_str_mv Repositório Institucional da UFSCAR - Universidade Federal de São Carlos (UFSCAR)
repository.mail.fl_str_mv
_version_ 1802136294294290432