Psychotria stachyoides: descobertas químicas e estruturais

Detalhes bibliográficos
Ano de defesa: 2009
Autor(a) principal: Pimenta, Antônia Torres Ávila
Orientador(a): Lima, Mary Anne Sousa
Banca de defesa: Não Informado pela instituição
Tipo de documento: Tese
Tipo de acesso: Acesso aberto
Idioma: por
Instituição de defesa: Não Informado pela instituição
Programa de Pós-Graduação: Não Informado pela instituição
Departamento: Não Informado pela instituição
País: Não Informado pela instituição
Palavras-chave em Português:
Link de acesso: http://www.repositorio.ufc.br/handle/riufc/61070
Resumo: In this work we present the phytochemical investigation of stems, leaves and roots of Psychotria stachyoides. The lack of reports on chemical studies with this species led us to this investigation, which brought new data to the chemotaxonomic knowledgement of Psychotria genus. The isolation of six new alkaloids named correantosides A-F corroborated the idea that alkaloids are important chemotaxonomic markers of this genus, and confirmed species of the Heteropsychotria sub-genus as monoterpene indole alkaloids producers. Moreover, the C13 nor-isoprenoid byzantionoside B, the hydroxypyran-2ones tetillapyrone, the triterpenes barbinevic acid and a—amyrine, the quinones alizarin 1-methyl-ether and rubiadine, the coumarin scopoletin and the glycosyl steroids sistosterol and stigmasterol as mixture were isolated. All the isolated compounds are new in the Psychotria genus, with exception of aamyrine and the steroids. The isolation of the chemical constituents were performed by the use of chromatographic techniques, including flash chromatography, thin layer chromatography, preparative chromatography, size exclusion chromatography and preparative high-performance liquid chromatography. The structural characterizations were performed by the use of infrared, mass spectrometry and nuclear magnetic resonance, including one and two-dimensional pulse sequences.
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spelling Pimenta, Antônia Torres ÁvilaLima, Mary Anne Sousa2021-10-08T14:40:27Z2021-10-08T14:40:27Z2009PIMENTA, Antônia Torres Ávila. Psychotria stachyoides: descobertas químicas e estruturais. 2009. 210 f. Tese (Doutorado em Química) - Universidade Federal do Ceará, Fortaleza, 2009.http://www.repositorio.ufc.br/handle/riufc/61070In this work we present the phytochemical investigation of stems, leaves and roots of Psychotria stachyoides. The lack of reports on chemical studies with this species led us to this investigation, which brought new data to the chemotaxonomic knowledgement of Psychotria genus. The isolation of six new alkaloids named correantosides A-F corroborated the idea that alkaloids are important chemotaxonomic markers of this genus, and confirmed species of the Heteropsychotria sub-genus as monoterpene indole alkaloids producers. Moreover, the C13 nor-isoprenoid byzantionoside B, the hydroxypyran-2ones tetillapyrone, the triterpenes barbinevic acid and a—amyrine, the quinones alizarin 1-methyl-ether and rubiadine, the coumarin scopoletin and the glycosyl steroids sistosterol and stigmasterol as mixture were isolated. All the isolated compounds are new in the Psychotria genus, with exception of aamyrine and the steroids. The isolation of the chemical constituents were performed by the use of chromatographic techniques, including flash chromatography, thin layer chromatography, preparative chromatography, size exclusion chromatography and preparative high-performance liquid chromatography. The structural characterizations were performed by the use of infrared, mass spectrometry and nuclear magnetic resonance, including one and two-dimensional pulse sequences.Neste trabalho foi realizada a investigação fitoquimica das folhas, talos e raizes de Psychotria stachyoides. A ausência de dados na literatura a cerca da constituição química desta espécie motivou a realização deste estudo, que adicionou novos elementos para o conhecimento quimiotaxonômico do gênero Psychotria. 0 isolamento de seis alcalóides de caráter inédito na literatura denominados de correantosideos A-F, corroborou os dados que sugerem os alcalóides como importantes marcadores quimiotaxeimicos do gênero, além de comprovar a tendência de espécies do subgênero Heteropsychotria em produzir alcalóides indólicos monoterpenicos. Além disso, foram isolados o C13 nor-Isoprenóide bizantionosida B, a 2-hidroxi-piranona tetilapirona, os triterpenos ácido babinérvico e a-amirina, as quinonas alizarina- 1 -metiléter e rubiadina, a cumarina escopoletina e a mistura de estóides sitosterol e estigmasterol glicosilados. Com exceção da a-amirina e da mistura de esteróides, todas as outras substâncias isoladas possuem caráter inédito no gênero, contribuindo, desta forma, para o conhecimento do perfil químico do mesmo. 0 isolamento dos constituintes químicos foi realizado através do uso de diversas técnicas cromatográficas, como: cromatografia "flash", cromatografia em camada delgada preparativa (CCDP), cromatografia por exclusão molecular em Sephadex LH-20 e cromatografia liquida de alta eficiência (CLAE). Para a caracterização estrutural dos constituintes químicos isolados, foram utilizados infravermelho (IV), espectroscopia de massas, e técnicas uni e bidimensionais de ressonância magnética nuclear (RMN).Psychotria stachyoidesAlcalóides indólicosCromatografiaEspectroscopiaPsychotria stachyoides: descobertas químicas e estruturaisinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/doctoralThesisporreponame:Repositório Institucional da Universidade Federal do Ceará (UFC)instname:Universidade Federal do Ceará (UFC)instacron:UFCinfo:eu-repo/semantics/openAccessLICENSElicense.txtlicense.txttext/plain; charset=utf-81748http://repositorio.ufc.br/bitstream/riufc/61070/2/license.txt8a4605be74aa9ea9d79846c1fba20a33MD52ORIGINAL2009_tese_atapimenta.pdf2009_tese_atapimenta.pdfapplication/pdf25242262http://repositorio.ufc.br/bitstream/riufc/61070/1/2009_tese_atapimenta.pdf22836941e57b95e7226fdb59c57c7504MD51riufc/610702021-10-08 11:40:27.312oai:repositorio.ufc.br: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Repositório InstitucionalPUBhttp://www.repositorio.ufc.br/ri-oai/requestbu@ufc.br || repositorio@ufc.bropendoar:2021-10-08T14:40:27Repositório Institucional da Universidade Federal do Ceará (UFC) - Universidade Federal do Ceará (UFC)false
dc.title.pt_BR.fl_str_mv Psychotria stachyoides: descobertas químicas e estruturais
title Psychotria stachyoides: descobertas químicas e estruturais
spellingShingle Psychotria stachyoides: descobertas químicas e estruturais
Pimenta, Antônia Torres Ávila
Psychotria stachyoides
Alcalóides indólicos
Cromatografia
Espectroscopia
title_short Psychotria stachyoides: descobertas químicas e estruturais
title_full Psychotria stachyoides: descobertas químicas e estruturais
title_fullStr Psychotria stachyoides: descobertas químicas e estruturais
title_full_unstemmed Psychotria stachyoides: descobertas químicas e estruturais
title_sort Psychotria stachyoides: descobertas químicas e estruturais
author Pimenta, Antônia Torres Ávila
author_facet Pimenta, Antônia Torres Ávila
author_role author
dc.contributor.author.fl_str_mv Pimenta, Antônia Torres Ávila
dc.contributor.advisor1.fl_str_mv Lima, Mary Anne Sousa
contributor_str_mv Lima, Mary Anne Sousa
dc.subject.por.fl_str_mv Psychotria stachyoides
Alcalóides indólicos
Cromatografia
Espectroscopia
topic Psychotria stachyoides
Alcalóides indólicos
Cromatografia
Espectroscopia
description In this work we present the phytochemical investigation of stems, leaves and roots of Psychotria stachyoides. The lack of reports on chemical studies with this species led us to this investigation, which brought new data to the chemotaxonomic knowledgement of Psychotria genus. The isolation of six new alkaloids named correantosides A-F corroborated the idea that alkaloids are important chemotaxonomic markers of this genus, and confirmed species of the Heteropsychotria sub-genus as monoterpene indole alkaloids producers. Moreover, the C13 nor-isoprenoid byzantionoside B, the hydroxypyran-2ones tetillapyrone, the triterpenes barbinevic acid and a—amyrine, the quinones alizarin 1-methyl-ether and rubiadine, the coumarin scopoletin and the glycosyl steroids sistosterol and stigmasterol as mixture were isolated. All the isolated compounds are new in the Psychotria genus, with exception of aamyrine and the steroids. The isolation of the chemical constituents were performed by the use of chromatographic techniques, including flash chromatography, thin layer chromatography, preparative chromatography, size exclusion chromatography and preparative high-performance liquid chromatography. The structural characterizations were performed by the use of infrared, mass spectrometry and nuclear magnetic resonance, including one and two-dimensional pulse sequences.
publishDate 2009
dc.date.issued.fl_str_mv 2009
dc.date.accessioned.fl_str_mv 2021-10-08T14:40:27Z
dc.date.available.fl_str_mv 2021-10-08T14:40:27Z
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 PIMENTA, Antônia Torres Ávila. Psychotria stachyoides: descobertas químicas e estruturais. 2009. 210 f. Tese (Doutorado em Química) - Universidade Federal do Ceará, Fortaleza, 2009.
dc.identifier.uri.fl_str_mv http://www.repositorio.ufc.br/handle/riufc/61070
identifier_str_mv PIMENTA, Antônia Torres Ávila. Psychotria stachyoides: descobertas químicas e estruturais. 2009. 210 f. Tese (Doutorado em Química) - Universidade Federal do Ceará, Fortaleza, 2009.
url http://www.repositorio.ufc.br/handle/riufc/61070
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