Estudo dos metabólitos secundários de Scutia buxifolia e suas atividades biológicas
Ano de defesa: | 2010 |
---|---|
Autor(a) principal: | |
Orientador(a): | |
Banca de defesa: | , , , |
Tipo de documento: | Tese |
Tipo de acesso: | Acesso aberto |
Idioma: | por |
Instituição de defesa: |
Universidade Federal de Santa Maria
|
Programa de Pós-Graduação: |
Programa de Pós-Graduação em Química
|
Departamento: |
Química
|
País: |
BR
|
Palavras-chave em Português: | |
Área do conhecimento CNPq: | |
Link de acesso: | http://repositorio.ufsm.br/handle/1/4187 |
Resumo: | In this work, four new neutral cycle peptide , scutianenes W (210), X (211), Y (212) and Z (213), have been isolated from Scutia buxifolia Reiss (Rhamnaceae) , along with seven know compounds, four cylopeptide alkaloids, scutianine B (99), scutianine C (100), scutianine D (101), and scutianine E (102), two triterpenoids , ursolic acid (215) and betulic acid (216), and two steroids, β-sitosterol (214) and β-sitosterol glycoside (217). The structures of compounds isolated were established by various spectroscopic techniques, including 1H and 13C NMR, COSY, NOESY, DEPT, HMQC and HMBC experiments, and comparison with authentic samples. Scutianenes W, X and Y are three diastereoisomeric compounds, with a 3- hydroxileucine as a β-hydroxiamino acid unit, which is connected to the styryl fragment via an ether bridge, and a β-phenylserine as a common ring-bonded amino acid. Attached to the amino group of the 3-hydroxiamino acid unit is a side chain trans CO-CH=CH-PH. In its turn, scutianene Z (213) has a phenylserine as the β-hydroxiamino acid unit, isoleucine as a common ring-bonded amino acid and the same side chain trans CO-CH=CH-PH. The stereochemistry of the four new compounds was established from coupling constants between H3/H4 and H-7/H-28, and by differences in chemical shifts of CH-3, CH-4, CH-7 and CH-28, on the 1H and 13C NMR spectra. The absolute stereochemistry of the diastereoisomeric scutianenes X (211) and Y (212), were confirmed by X-ray diffraction analysis of its O-acetyl derivatives. In addition, extracts and compounds isolated were evaluated for its antimicrobial activity against Gram-positive and Gram-negative bacteria and yeasts, and for its Acetylcholinesterase inhibitory activity. |
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2017-03-022017-03-022010-04-16MALDANER, Graciela. Study of the secondary metabolites of Scutia buxifolia and its biological activities . 2010. 201 f. Tese (Doutorado em Química) - Universidade Federal de Santa Maria, Santa Maria, 2010.http://repositorio.ufsm.br/handle/1/4187In this work, four new neutral cycle peptide , scutianenes W (210), X (211), Y (212) and Z (213), have been isolated from Scutia buxifolia Reiss (Rhamnaceae) , along with seven know compounds, four cylopeptide alkaloids, scutianine B (99), scutianine C (100), scutianine D (101), and scutianine E (102), two triterpenoids , ursolic acid (215) and betulic acid (216), and two steroids, β-sitosterol (214) and β-sitosterol glycoside (217). The structures of compounds isolated were established by various spectroscopic techniques, including 1H and 13C NMR, COSY, NOESY, DEPT, HMQC and HMBC experiments, and comparison with authentic samples. Scutianenes W, X and Y are three diastereoisomeric compounds, with a 3- hydroxileucine as a β-hydroxiamino acid unit, which is connected to the styryl fragment via an ether bridge, and a β-phenylserine as a common ring-bonded amino acid. Attached to the amino group of the 3-hydroxiamino acid unit is a side chain trans CO-CH=CH-PH. In its turn, scutianene Z (213) has a phenylserine as the β-hydroxiamino acid unit, isoleucine as a common ring-bonded amino acid and the same side chain trans CO-CH=CH-PH. The stereochemistry of the four new compounds was established from coupling constants between H3/H4 and H-7/H-28, and by differences in chemical shifts of CH-3, CH-4, CH-7 and CH-28, on the 1H and 13C NMR spectra. The absolute stereochemistry of the diastereoisomeric scutianenes X (211) and Y (212), were confirmed by X-ray diffraction analysis of its O-acetyl derivatives. In addition, extracts and compounds isolated were evaluated for its antimicrobial activity against Gram-positive and Gram-negative bacteria and yeasts, and for its Acetylcholinesterase inhibitory activity.Neste trabalho, quatro novos ciclopeptídeos neutros foram isolados de Scutia buxifolia Reiss (Rhamnaceae), scutianenos W (210), X (211), Y (212) e Z (213), juntamente com sete compostos conhecidos, quatro alcalóides ciclopeptídicos, scutianina B (99), scutianina C (100), scutianina D (101) e scutianina (102), dois triterpenos, ácido ursólico (215) e acido betulínico (216) e dois esteróides β-sitosterol (214) e β-sitosterol glicosilado. As estruturas dos compostos isolados foram determinados por várias técnicas espectroscópicas, incluindo experimentos RMN 1H e 13C, COSY, NOESY, DEPT, HMQC e HMBC, e por comparação com amostras autênticas. Scutianenos W, X e Y são três compostos diastereoisoméricos, tendo a com 3-hidroxileucina como a unidade de �-hidroxiaminoácido, que está ligado ao fragmento estirilamina através de uma ligação fenol- éter, e uma unidade β-fenilserina como sendo o β- aminoácido do macrociclo. Ligado ao grupo amino temos uma unidade da cadeia lateral [-COCH = CHPh]. Por sua vez, o scutianeno Z (213) possui uma fenilserina como unidade de β- hidroxiaminoácido, isoleucina como um aminoácido ligado ao macrociclo, ligado ao grupo amino temos uma unidade da cadeia lateral [-CO-CH = CHPh]. A estereoquímica dos quatro novos compostos foi estabelecida a partir de constantes de acoplamento entre H3/H4 e H-7/H-28, e pelas diferenças de deslocamentos químicos do CH-3, CH-4, CH-7 e CH-28, nos espectros de RMN de 1H e 13C. A estereoquímica absoluta dos scutianenos diastereoisoméricos X (211) e Y (212), foram confirmados por análise de difração de raios-X de seus derivados O-acetil. Além disso, extratos e todos os compostos isolados foram avaliados para atividade antimicrobiana frente a bactérias Gram-positivas e gram-negativas e leveduras, e determinada a atividade de inibição da acetilcolinesterase.Conselho Nacional de Desenvolvimento Científico e Tecnológicoapplication/pdfporUniversidade Federal de Santa MariaPrograma de Pós-Graduação em QuímicaUFSMBRQuímicaAlcalóides ciclopeptídicosScutia buxifoliaCiclopeptideos neutrosCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA Estudo dos metabólitos secundários de Scutia buxifolia e suas atividades biológicas Study of the secondary metabolites of Scutia buxifolia and its biological activities info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/doctoralThesisMorel, Ademir Fariashttp://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4783930A8Caro, Miguel Soriano Balpardahttp://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4788537Y2Moura, Neusa Fernandes dehttp://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4792107A9Dalcol, Ionara Irionhttp://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4797864E9Braibante, Mara Elisa Forteshttp://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4788627U5http://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4706171T4Maldaner, Graciela1006000000004003003003003005005008c99befa-f1b3-4afb-98b8-7fab46c3d493d5d3ff0a-484a-4ef7-90ef-17a3b1bfcc03b1967cca-e175-4abf-8b56-23845f27001124bb05e9-ab5c-4992-b51a-839d83a4893311b367fb-0eed-426e-9ab5-e42e52a8d098990091ed-44c1-4e1b-9680-46ffd63eccb3info:eu-repo/semantics/openAccessreponame:Manancial - Repositório Digital da UFSMinstname:Universidade Federal de Santa Maria (UFSM)instacron:UFSMORIGINALMALDANER, GRACIELA.pdfapplication/pdf27124437http://repositorio.ufsm.br/bitstream/1/4187/1/MALDANER%2c%20GRACIELA.pdf5795106852252ba11d7ddc9fe72b3878MD51TEXTMALDANER, GRACIELA.pdf.txtMALDANER, GRACIELA.pdf.txtExtracted texttext/plain281624http://repositorio.ufsm.br/bitstream/1/4187/2/MALDANER%2c%20GRACIELA.pdf.txtaf46ba22a3237aa984b2361755cf75d8MD52THUMBNAILMALDANER, GRACIELA.pdf.jpgMALDANER, GRACIELA.pdf.jpgIM Thumbnailimage/jpeg5439http://repositorio.ufsm.br/bitstream/1/4187/3/MALDANER%2c%20GRACIELA.pdf.jpgbb09dd84e55f7384204ecab836808058MD531/41872017-07-25 11:05:17.045oai:repositorio.ufsm.br:1/4187Repositório Institucionalhttp://repositorio.ufsm.br/PUBhttp://repositorio.ufsm.br/oai/requestopendoar:39132017-07-25T14:05:17Manancial - Repositório Digital da UFSM - Universidade Federal de Santa Maria (UFSM)false |
dc.title.por.fl_str_mv |
Estudo dos metabólitos secundários de Scutia buxifolia e suas atividades biológicas |
dc.title.alternative.eng.fl_str_mv |
Study of the secondary metabolites of Scutia buxifolia and its biological activities |
title |
Estudo dos metabólitos secundários de Scutia buxifolia e suas atividades biológicas |
spellingShingle |
Estudo dos metabólitos secundários de Scutia buxifolia e suas atividades biológicas Maldaner, Graciela Alcalóides ciclopeptídicos Scutia buxifolia Ciclopeptideos neutros CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
title_short |
Estudo dos metabólitos secundários de Scutia buxifolia e suas atividades biológicas |
title_full |
Estudo dos metabólitos secundários de Scutia buxifolia e suas atividades biológicas |
title_fullStr |
Estudo dos metabólitos secundários de Scutia buxifolia e suas atividades biológicas |
title_full_unstemmed |
Estudo dos metabólitos secundários de Scutia buxifolia e suas atividades biológicas |
title_sort |
Estudo dos metabólitos secundários de Scutia buxifolia e suas atividades biológicas |
author |
Maldaner, Graciela |
author_facet |
Maldaner, Graciela |
author_role |
author |
dc.contributor.advisor1.fl_str_mv |
Morel, Ademir Farias |
dc.contributor.advisor1Lattes.fl_str_mv |
http://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4783930A8 |
dc.contributor.referee1.fl_str_mv |
Caro, Miguel Soriano Balparda |
dc.contributor.referee1Lattes.fl_str_mv |
http://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4788537Y2 |
dc.contributor.referee2.fl_str_mv |
Moura, Neusa Fernandes de |
dc.contributor.referee2Lattes.fl_str_mv |
http://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4792107A9 |
dc.contributor.referee3.fl_str_mv |
Dalcol, Ionara Irion |
dc.contributor.referee3Lattes.fl_str_mv |
http://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4797864E9 |
dc.contributor.referee4.fl_str_mv |
Braibante, Mara Elisa Fortes |
dc.contributor.referee4Lattes.fl_str_mv |
http://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4788627U5 |
dc.contributor.authorLattes.fl_str_mv |
http://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4706171T4 |
dc.contributor.author.fl_str_mv |
Maldaner, Graciela |
contributor_str_mv |
Morel, Ademir Farias Caro, Miguel Soriano Balparda Moura, Neusa Fernandes de Dalcol, Ionara Irion Braibante, Mara Elisa Fortes |
dc.subject.por.fl_str_mv |
Alcalóides ciclopeptídicos Scutia buxifolia Ciclopeptideos neutros |
topic |
Alcalóides ciclopeptídicos Scutia buxifolia Ciclopeptideos neutros CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
dc.subject.cnpq.fl_str_mv |
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
description |
In this work, four new neutral cycle peptide , scutianenes W (210), X (211), Y (212) and Z (213), have been isolated from Scutia buxifolia Reiss (Rhamnaceae) , along with seven know compounds, four cylopeptide alkaloids, scutianine B (99), scutianine C (100), scutianine D (101), and scutianine E (102), two triterpenoids , ursolic acid (215) and betulic acid (216), and two steroids, β-sitosterol (214) and β-sitosterol glycoside (217). The structures of compounds isolated were established by various spectroscopic techniques, including 1H and 13C NMR, COSY, NOESY, DEPT, HMQC and HMBC experiments, and comparison with authentic samples. Scutianenes W, X and Y are three diastereoisomeric compounds, with a 3- hydroxileucine as a β-hydroxiamino acid unit, which is connected to the styryl fragment via an ether bridge, and a β-phenylserine as a common ring-bonded amino acid. Attached to the amino group of the 3-hydroxiamino acid unit is a side chain trans CO-CH=CH-PH. In its turn, scutianene Z (213) has a phenylserine as the β-hydroxiamino acid unit, isoleucine as a common ring-bonded amino acid and the same side chain trans CO-CH=CH-PH. The stereochemistry of the four new compounds was established from coupling constants between H3/H4 and H-7/H-28, and by differences in chemical shifts of CH-3, CH-4, CH-7 and CH-28, on the 1H and 13C NMR spectra. The absolute stereochemistry of the diastereoisomeric scutianenes X (211) and Y (212), were confirmed by X-ray diffraction analysis of its O-acetyl derivatives. In addition, extracts and compounds isolated were evaluated for its antimicrobial activity against Gram-positive and Gram-negative bacteria and yeasts, and for its Acetylcholinesterase inhibitory activity. |
publishDate |
2010 |
dc.date.issued.fl_str_mv |
2010-04-16 |
dc.date.accessioned.fl_str_mv |
2017-03-02 |
dc.date.available.fl_str_mv |
2017-03-02 |
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 |
MALDANER, Graciela. Study of the secondary metabolites of Scutia buxifolia and its biological activities . 2010. 201 f. Tese (Doutorado em Química) - Universidade Federal de Santa Maria, Santa Maria, 2010. |
dc.identifier.uri.fl_str_mv |
http://repositorio.ufsm.br/handle/1/4187 |
identifier_str_mv |
MALDANER, Graciela. Study of the secondary metabolites of Scutia buxifolia and its biological activities . 2010. 201 f. Tese (Doutorado em Química) - Universidade Federal de Santa Maria, Santa Maria, 2010. |
url |
http://repositorio.ufsm.br/handle/1/4187 |
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por |
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100600000000 |
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Universidade Federal de Santa Maria |
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UFSM |
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