Contribuição química para os voláteis de Aristolochia trilobata e obtenção do acetato de 6-metil-5-hepten-2-ila por biotransformação
Ano de defesa: | 2013 |
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Autor(a) principal: | |
Orientador(a): | |
Banca de defesa: | |
Tipo de documento: | Dissertação |
Tipo de acesso: | Acesso aberto |
Idioma: | por |
Instituição de defesa: |
Não Informado pela instituição
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Programa de Pós-Graduação: |
Pós-Graduação em Química
|
Departamento: |
Não Informado pela instituição
|
País: |
Não Informado pela instituição
|
Palavras-chave em Português: | |
Palavras-chave em Inglês: | |
Área do conhecimento CNPq: | |
Link de acesso: | https://ri.ufs.br/handle/riufs/6035 |
Resumo: | Aristolochia genus consists of about 400 species, among which is the Aristolochia trilobata L. This species is commonly used as medicinal plant by Central and South American people against snakes and scorpions bites in the treatment of stomach pains, cramps and diabetes and for the removal of placental among others. However, there are not studies that reports the chemical components of this plant, therefore, this study intended to identify the volatile chemicals in the oil, and the full characterization of the majority constituent of essential oil and offer a way to obtain it via biotransformation. It was observed that the major component of the essential oil is the (R)-sulcatyl acetate (23.31%), while in the hydrolate the major component is linalool (29.51%). The antinociceptive activity of A. trilobata essential oil and (R)-sulcatyl acetate was evaluated, which showed a strong analgesic activity and did not show any significant motor performance alterations. Two routes were proposed to obtain sulcatyl acetate: one by conventional chemical synthesis and another by biotransformation. For the chemical synthesis sulcatona was used how starting material that was reduced and yielded sulcatol (98%), which was acetylated (83% yield). The route by biotransformation had hao starting material geraniol, being evaluated the ability of the fungus Penicillium oxallicum in the biotransformation from geraniol to sulcatona. It was also evaluated the ability of the fungi Aspergillus niger, Aspergillus sp. P. oxallicum, fungus isolated from Spondias tuberous (umbu) and Passiflora edulis (passion fruit) peel, to reduce sulcatona, resulting in a reduction of different percentage for each medium tested. It was also tested A. niger, Aspergillus sp., P. oxallicum and the fungus isolated from umbu , for sulcatol acetylation with stereoselectivity. The region-/stereoselectivity of the reactions was evaluated by GC/FID chiral, obtaining sulcatone reduction with A. niger, and the stereoselectivity in the racemic sulcatol acetylation catalyzed by Aspergillus sp. was obtained (S)-sulcatyl acetate with isomeric purity, and also obtaining pure (R)-sulcatyl acetate with P. oxallicum. It was possible to observe a mixture of isomers from the reaction catalyzed by the isolated fungus from umbu. |
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Santos, Darlisson de Alexandriahttp://lattes.cnpq.br/7939017634049710Alves, Péricles Barretohttp://lattes.cnpq.br/63380443663408532017-09-27T13:57:17Z2017-09-27T13:57:17Z2013-02-08https://ri.ufs.br/handle/riufs/6035Aristolochia genus consists of about 400 species, among which is the Aristolochia trilobata L. This species is commonly used as medicinal plant by Central and South American people against snakes and scorpions bites in the treatment of stomach pains, cramps and diabetes and for the removal of placental among others. However, there are not studies that reports the chemical components of this plant, therefore, this study intended to identify the volatile chemicals in the oil, and the full characterization of the majority constituent of essential oil and offer a way to obtain it via biotransformation. It was observed that the major component of the essential oil is the (R)-sulcatyl acetate (23.31%), while in the hydrolate the major component is linalool (29.51%). The antinociceptive activity of A. trilobata essential oil and (R)-sulcatyl acetate was evaluated, which showed a strong analgesic activity and did not show any significant motor performance alterations. Two routes were proposed to obtain sulcatyl acetate: one by conventional chemical synthesis and another by biotransformation. For the chemical synthesis sulcatona was used how starting material that was reduced and yielded sulcatol (98%), which was acetylated (83% yield). The route by biotransformation had hao starting material geraniol, being evaluated the ability of the fungus Penicillium oxallicum in the biotransformation from geraniol to sulcatona. It was also evaluated the ability of the fungi Aspergillus niger, Aspergillus sp. P. oxallicum, fungus isolated from Spondias tuberous (umbu) and Passiflora edulis (passion fruit) peel, to reduce sulcatona, resulting in a reduction of different percentage for each medium tested. It was also tested A. niger, Aspergillus sp., P. oxallicum and the fungus isolated from umbu , for sulcatol acetylation with stereoselectivity. The region-/stereoselectivity of the reactions was evaluated by GC/FID chiral, obtaining sulcatone reduction with A. niger, and the stereoselectivity in the racemic sulcatol acetylation catalyzed by Aspergillus sp. was obtained (S)-sulcatyl acetate with isomeric purity, and also obtaining pure (R)-sulcatyl acetate with P. oxallicum. It was possible to observe a mixture of isomers from the reaction catalyzed by the isolated fungus from umbu.O gênero Aristolochia é constituído por aproximadamente 400 espécies, dentre as quais encontra-se a Aristolochia trilobata L. Essa espécie é utilizada na medicina popular nas Américas Central e do Sul contra picadas de cobras e escorpiões, no tratamento de dores estomacais, cólicas e diabetes e para a remoção de placentas, entre outras. No entanto, nenhum trabalho relata os componentes químicos dessa planta e, portanto, o presente trabalho visou a identificação química dos voláteis existentes na mesma, bem como o isolamento, a caracterização e a identificação do constituinte majoritário, R(+)-2-acetil 6-metil-5-hepteno (acetato de sulcatila), com 23,31% presente no óleo essencial. O linalol (29,51%) foi identificado no hidrolato como constituinte majoritário. O óleo essencial e o (R)-acetato de sulcatila tiveram suas atividades antinociceptivas avaliadas em camundongos, os quais apresentaram capacidade de analgesia sem interferir na capacidade motora. Foram realizadas duas propostas para a síntese do acetato sulcatila, uma por síntese convencional e outra por biotransformação. Para a proposta sintética utilizou-se a sulcatona como material de partida, obtendo-se sulcatol (98% de rendimento) a partir da redução, o qual foi acetilado (83% de rendimento). A rota por biotransformação partiu da conversão do geraniol em sulcatona pelo fungo Penicillium oxallicum, sendo avaliado, posteriormente, a capacidade dos fungos Aspergillus niger, Aspergillus sp., P. oxallicum, fungos isolados de Spondias tuberosa (umbu) e das cascas de Passiflora edulis (maracujá) para a redução da sulcatona, obtendo-se a redução com percentuais diferentes para cada meio testado. Foram também realizadas reações de acetilação do sulcatol utilizando os fungos A. niger, Aspergillus sp., P. oxallicum e o fungo isolado do umbu. A régio/estereosseletividade das reações foi avaliada por CG/DIC quiral, sendo possível observar uma regiosseletividade na redução da sulcatona por A. niger e a estereosseletividade na acetilação do sulcatol racêmico catalisada pelo fungo Aspergillus sp., sendo obtido o (S)-acetato de sulcatila com pureza isomérica, e obteve-se o (R)-acetato de sulcatila puro com P. oxallicum, sendo possível também observar uma mistura de isômeros a partir da reação catalisada pelo fungo isolado do umbu.application/pdfporEssências e óleos essenciaisQuímica orgânicaAristolóquiaAristoloquiáceaAristolochia trilobataAcetato de sulcatilaBiotransformaçãoAristolochia trilobataEssential oilSulcatyl acetateBiotransformationCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICAContribuição química para os voláteis de Aristolochia trilobata e obtenção do acetato de 6-metil-5-hepten-2-ila por biotransformaçãoinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesisPós-Graduação em Químicainfo:eu-repo/semantics/openAccessreponame:Repositório Institucional da UFSinstname:Universidade Federal de Sergipe (UFS)instacron:UFSORIGINALDARLISSON_ALEXANDRIA_SANTOS.pdfapplication/pdf3163238https://ri.ufs.br/jspui/bitstream/riufs/6035/1/DARLISSON_ALEXANDRIA_SANTOS.pdf89f1c725efeec0ae22dfaaddf575b391MD51TEXTDARLISSON_ALEXANDRIA_SANTOS.pdf.txtDARLISSON_ALEXANDRIA_SANTOS.pdf.txtExtracted texttext/plain171700https://ri.ufs.br/jspui/bitstream/riufs/6035/2/DARLISSON_ALEXANDRIA_SANTOS.pdf.txt0ce76b00e2315aa2dc157efc678fcc0dMD52THUMBNAILDARLISSON_ALEXANDRIA_SANTOS.pdf.jpgDARLISSON_ALEXANDRIA_SANTOS.pdf.jpgGenerated Thumbnailimage/jpeg1408https://ri.ufs.br/jspui/bitstream/riufs/6035/3/DARLISSON_ALEXANDRIA_SANTOS.pdf.jpg1a9849bbb76246b6ccfec60bc8ae7e88MD53riufs/60352018-01-16 19:33:23.422oai:ufs.br:riufs/6035Repositório InstitucionalPUBhttps://ri.ufs.br/oai/requestrepositorio@academico.ufs.bropendoar:2018-01-16T22:33:23Repositório Institucional da UFS - Universidade Federal de Sergipe (UFS)false |
dc.title.por.fl_str_mv |
Contribuição química para os voláteis de Aristolochia trilobata e obtenção do acetato de 6-metil-5-hepten-2-ila por biotransformação |
title |
Contribuição química para os voláteis de Aristolochia trilobata e obtenção do acetato de 6-metil-5-hepten-2-ila por biotransformação |
spellingShingle |
Contribuição química para os voláteis de Aristolochia trilobata e obtenção do acetato de 6-metil-5-hepten-2-ila por biotransformação Santos, Darlisson de Alexandria Essências e óleos essenciais Química orgânica Aristolóquia Aristoloquiácea Aristolochia trilobata Acetato de sulcatila Biotransformação Aristolochia trilobata Essential oil Sulcatyl acetate Biotransformation CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
title_short |
Contribuição química para os voláteis de Aristolochia trilobata e obtenção do acetato de 6-metil-5-hepten-2-ila por biotransformação |
title_full |
Contribuição química para os voláteis de Aristolochia trilobata e obtenção do acetato de 6-metil-5-hepten-2-ila por biotransformação |
title_fullStr |
Contribuição química para os voláteis de Aristolochia trilobata e obtenção do acetato de 6-metil-5-hepten-2-ila por biotransformação |
title_full_unstemmed |
Contribuição química para os voláteis de Aristolochia trilobata e obtenção do acetato de 6-metil-5-hepten-2-ila por biotransformação |
title_sort |
Contribuição química para os voláteis de Aristolochia trilobata e obtenção do acetato de 6-metil-5-hepten-2-ila por biotransformação |
author |
Santos, Darlisson de Alexandria |
author_facet |
Santos, Darlisson de Alexandria |
author_role |
author |
dc.contributor.author.fl_str_mv |
Santos, Darlisson de Alexandria |
dc.contributor.advisor1Lattes.fl_str_mv |
http://lattes.cnpq.br/7939017634049710 |
dc.contributor.advisor1.fl_str_mv |
Alves, Péricles Barreto |
dc.contributor.authorLattes.fl_str_mv |
http://lattes.cnpq.br/6338044366340853 |
contributor_str_mv |
Alves, Péricles Barreto |
dc.subject.por.fl_str_mv |
Essências e óleos essenciais Química orgânica Aristolóquia Aristoloquiácea Aristolochia trilobata Acetato de sulcatila Biotransformação |
topic |
Essências e óleos essenciais Química orgânica Aristolóquia Aristoloquiácea Aristolochia trilobata Acetato de sulcatila Biotransformação Aristolochia trilobata Essential oil Sulcatyl acetate Biotransformation CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
dc.subject.eng.fl_str_mv |
Aristolochia trilobata Essential oil Sulcatyl acetate Biotransformation |
dc.subject.cnpq.fl_str_mv |
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
description |
Aristolochia genus consists of about 400 species, among which is the Aristolochia trilobata L. This species is commonly used as medicinal plant by Central and South American people against snakes and scorpions bites in the treatment of stomach pains, cramps and diabetes and for the removal of placental among others. However, there are not studies that reports the chemical components of this plant, therefore, this study intended to identify the volatile chemicals in the oil, and the full characterization of the majority constituent of essential oil and offer a way to obtain it via biotransformation. It was observed that the major component of the essential oil is the (R)-sulcatyl acetate (23.31%), while in the hydrolate the major component is linalool (29.51%). The antinociceptive activity of A. trilobata essential oil and (R)-sulcatyl acetate was evaluated, which showed a strong analgesic activity and did not show any significant motor performance alterations. Two routes were proposed to obtain sulcatyl acetate: one by conventional chemical synthesis and another by biotransformation. For the chemical synthesis sulcatona was used how starting material that was reduced and yielded sulcatol (98%), which was acetylated (83% yield). The route by biotransformation had hao starting material geraniol, being evaluated the ability of the fungus Penicillium oxallicum in the biotransformation from geraniol to sulcatona. It was also evaluated the ability of the fungi Aspergillus niger, Aspergillus sp. P. oxallicum, fungus isolated from Spondias tuberous (umbu) and Passiflora edulis (passion fruit) peel, to reduce sulcatona, resulting in a reduction of different percentage for each medium tested. It was also tested A. niger, Aspergillus sp., P. oxallicum and the fungus isolated from umbu , for sulcatol acetylation with stereoselectivity. The region-/stereoselectivity of the reactions was evaluated by GC/FID chiral, obtaining sulcatone reduction with A. niger, and the stereoselectivity in the racemic sulcatol acetylation catalyzed by Aspergillus sp. was obtained (S)-sulcatyl acetate with isomeric purity, and also obtaining pure (R)-sulcatyl acetate with P. oxallicum. It was possible to observe a mixture of isomers from the reaction catalyzed by the isolated fungus from umbu. |
publishDate |
2013 |
dc.date.issued.fl_str_mv |
2013-02-08 |
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2017-09-27T13:57:17Z |
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2017-09-27T13:57:17Z |
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