Psychotria stachyoides: descobertas químicas e estruturais
| Ano de defesa: | 2009 |
|---|---|
| Autor(a) principal: | |
| Orientador(a): | |
| Banca de defesa: | |
| Tipo de documento: | Tese |
| Tipo de acesso: | Acesso aberto |
| Idioma: | por |
| Instituição de defesa: |
Não Informado pela instituição
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| Programa de Pós-Graduação: |
Não Informado pela instituição
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| Departamento: |
Não Informado pela instituição
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| 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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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:riufc/61070Tk9URTogUExBQ0UgWU9VUiBPV04gTElDRU5TRSBIRVJFClRoaXMgc2FtcGxlIGxpY2Vuc2UgaXMgcHJvdmlkZWQgZm9yIGluZm9ybWF0aW9uYWwgcHVycG9zZXMgb25seS4KCk5PTi1FWENMVVNJVkUgRElTVFJJQlVUSU9OIExJQ0VOU0UKCkJ5IHNpZ25pbmcgYW5kIHN1Ym1pdHRpbmcgdGhpcyBsaWNlbnNlLCB5b3UgKHRoZSBhdXRob3Iocykgb3IgY29weXJpZ2h0Cm93bmVyKSBncmFudHMgdG8gRFNwYWNlIFVuaXZlcnNpdHkgKERTVSkgdGhlIG5vbi1leGNsdXNpdmUgcmlnaHQgdG8gcmVwcm9kdWNlLAp0cmFuc2xhdGUgKGFzIGRlZmluZWQgYmVsb3cpLCBhbmQvb3IgZGlzdHJpYnV0ZSB5b3VyIHN1Ym1pc3Npb24gKGluY2x1ZGluZwp0aGUgYWJzdHJhY3QpIHdvcmxkd2lkZSBpbiBwcmludCBhbmQgZWxlY3Ryb25pYyBmb3JtYXQgYW5kIGluIGFueSBtZWRpdW0sCmluY2x1ZGluZyBidXQgbm90IGxpbWl0ZWQgdG8gYXVkaW8gb3IgdmlkZW8uCgpZb3UgYWdyZWUgdGhhdCBEU1UgbWF5LCB3aXRob3V0IGNoYW5naW5nIHRoZSBjb250ZW50LCB0cmFuc2xhdGUgdGhlCnN1Ym1pc3Npb24gdG8gYW55IG1lZGl1bSBvciBmb3JtYXQgZm9yIHRoZSBwdXJwb3NlIG9mIHByZXNlcnZhdGlvbi4KCllvdSBhbHNvIGFncmVlIHRoYXQgRFNVIG1heSBrZWVwIG1vcmUgdGhhbiBvbmUgY29weSBvZiB0aGlzIHN1Ym1pc3Npb24gZm9yCnB1cnBvc2VzIG9mIHNlY3VyaXR5LCBiYWNrLXVwIGFuZCBwcmVzZXJ2YXRpb24uCgpZb3UgcmVwcmVzZW50IHRoYXQgdGhlIHN1Ym1pc3Npb24gaXMgeW91ciBvcmlnaW5hbCB3b3JrLCBhbmQgdGhhdCB5b3UgaGF2ZQp0aGUgcmlnaHQgdG8gZ3JhbnQgdGhlIHJpZ2h0cyBjb250YWluZWQgaW4gdGhpcyBsaWNlbnNlLiBZb3UgYWxzbyByZXByZXNlbnQKdGhhdCB5b3VyIHN1Ym1pc3Npb24gZG9lcyBub3QsIHRvIHRoZSBiZXN0IG9mIHlvdXIga25vd2xlZGdlLCBpbmZyaW5nZSB1cG9uCmFueW9uZSdzIGNvcHlyaWdodC4KCklmIHRoZSBzdWJtaXNzaW9uIGNvbnRhaW5zIG1hdGVyaWFsIGZvciB3aGljaCB5b3UgZG8gbm90IGhvbGQgY29weXJpZ2h0LAp5b3UgcmVwcmVzZW50IHRoYXQgeW91IGhhdmUgb2J0YWluZWQgdGhlIHVucmVzdHJpY3RlZCBwZXJtaXNzaW9uIG9mIHRoZQpjb3B5cmlnaHQgb3duZXIgdG8gZ3JhbnQgRFNVIHRoZSByaWdodHMgcmVxdWlyZWQgYnkgdGhpcyBsaWNlbnNlLCBhbmQgdGhhdApzdWNoIHRoaXJkLXBhcnR5IG93bmVkIG1hdGVyaWFsIGlzIGNsZWFybHkgaWRlbnRpZmllZCBhbmQgYWNrbm93bGVkZ2VkCndpdGhpbiB0aGUgdGV4dCBvciBjb250ZW50IG9mIHRoZSBzdWJtaXNzaW9uLgoKSUYgVEhFIFNVQk1JU1NJT04gSVMgQkFTRUQgVVBPTiBXT1JLIFRIQVQgSEFTIEJFRU4gU1BPTlNPUkVEIE9SIFNVUFBPUlRFRApCWSBBTiBBR0VOQ1kgT1IgT1JHQU5JWkFUSU9OIE9USEVSIFRIQU4gRFNVLCBZT1UgUkVQUkVTRU5UIFRIQVQgWU9VIEhBVkUKRlVMRklMTEVEIEFOWSBSSUdIVCBPRiBSRVZJRVcgT1IgT1RIRVIgT0JMSUdBVElPTlMgUkVRVUlSRUQgQlkgU1VDSApDT05UUkFDVCBPUiBBR1JFRU1FTlQuCgpEU1Ugd2lsbCBjbGVhcmx5IGlkZW50aWZ5IHlvdXIgbmFtZShzKSBhcyB0aGUgYXV0aG9yKHMpIG9yIG93bmVyKHMpIG9mIHRoZQpzdWJtaXNzaW9uLCBhbmQgd2lsbCBub3QgbWFrZSBhbnkgYWx0ZXJhdGlvbiwgb3RoZXIgdGhhbiBhcyBhbGxvd2VkIGJ5IHRoaXMKbGljZW5zZSwgdG8geW91ciBzdWJtaXNzaW9uLgo=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 |
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2009 |
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2021-10-08T14:40:27Z |
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2021-10-08T14:40:27Z |
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info:eu-repo/semantics/publishedVersion |
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info:eu-repo/semantics/doctoralThesis |
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publishedVersion |
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PIMENTA, Antônia Torres Ávila. Psychotria stachyoides: descobertas químicas e estruturais. 2009. 210 f. Tese (Doutorado em Química) - Universidade Federal do Ceará, Fortaleza, 2009. |
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http://www.repositorio.ufc.br/handle/riufc/61070 |
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PIMENTA, Antônia Torres Ávila. Psychotria stachyoides: descobertas químicas e estruturais. 2009. 210 f. Tese (Doutorado em Química) - Universidade Federal do Ceará, Fortaleza, 2009. |
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por |
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