Obtenção e quantificação de (-)-hinoquinina a partir da transformação microbiana da (-)-cubebina por Aspergillus niger
Autor(a) principal: | |
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Data de Publicação: | 2015 |
Tipo de documento: | Dissertação |
Idioma: | por |
Título da fonte: | Repositório do Centro Universitário Braz Cubas |
Texto Completo: | https://repositorio.cruzeirodosul.edu.br/handle/123456789/972 |
Resumo: | -)-Cubebin is a lignan found in several plant species and has various biological activities already described. In addition, it is used as a starting material for semi-synthesis of other structurally related lignans such as (-) - hinokinin, which is effective against several diseases, highlighting trypanocidal activity. So, the obtainment of this compound is promising based on the fact that the drugs currently on the market are not completely effective and are relatively toxic to the patient. The semi-synthesis of this compound from (-)-cubebin is usually catalyzed by pyridinium chlorochromate, a toxic and polluting reagent. So, due to there being no study of the obtainment of this compound using biotechnological methods, which are considered "green" methods: it promotes the reduction of hazardous wastes to the health of living beings and the environment, this study is aimed at obtaining (-)-hinokinin from biotransformation of (-) - cubebin by Aspergillus niger. So, in the first instance, (-)-cubebin was isolated from dried seeds of Piper cubeba using chromatographic techniques and the time necessary for the complete transformation of the substrate was evaluated. Then, the biotransformation was carried out on a large scale and the extract obtained from fungal transformation was fractionated by chromatographic techniques to obtain (-) - hinokinin. The confirmation of this structure and (-)-cubebin’s was performed by 1H NMR and 13C. For daily quantification of the target product, microbial transformation was performed on small scale and the daily fungal extracts obtained after each day of biotransformation were analysed in HPLC. After the specified period for transformation of the entire substrate, which was equal to 14 days, it was found that the yield was equal to 14.52% and to prove that the quantification performed was reliable, the method used was validated in accordance with the resolution RE 899/2003 of ANVISA. Then, considering the results of this work, it was found that the yield obtained is promising and the method used is a "green" alternative to the way of obtaining (-)-hinokinin from (-)-cubebin. Key-words: (-)-cubebin; (-)-hinokinin; fungal transformation |
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Obtenção e quantificação de (-)-hinoquinina a partir da transformação microbiana da (-)-cubebina por Aspergillus nigerObtainment and quantification of (-)-hinokinin from microbial transformation of (-)-cubebin by Aspergillus niger(-)-cubebina(-)-hinoquininaBiotransformação fúngicaCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA-)-Cubebin is a lignan found in several plant species and has various biological activities already described. In addition, it is used as a starting material for semi-synthesis of other structurally related lignans such as (-) - hinokinin, which is effective against several diseases, highlighting trypanocidal activity. So, the obtainment of this compound is promising based on the fact that the drugs currently on the market are not completely effective and are relatively toxic to the patient. The semi-synthesis of this compound from (-)-cubebin is usually catalyzed by pyridinium chlorochromate, a toxic and polluting reagent. So, due to there being no study of the obtainment of this compound using biotechnological methods, which are considered "green" methods: it promotes the reduction of hazardous wastes to the health of living beings and the environment, this study is aimed at obtaining (-)-hinokinin from biotransformation of (-) - cubebin by Aspergillus niger. So, in the first instance, (-)-cubebin was isolated from dried seeds of Piper cubeba using chromatographic techniques and the time necessary for the complete transformation of the substrate was evaluated. Then, the biotransformation was carried out on a large scale and the extract obtained from fungal transformation was fractionated by chromatographic techniques to obtain (-) - hinokinin. The confirmation of this structure and (-)-cubebin’s was performed by 1H NMR and 13C. For daily quantification of the target product, microbial transformation was performed on small scale and the daily fungal extracts obtained after each day of biotransformation were analysed in HPLC. After the specified period for transformation of the entire substrate, which was equal to 14 days, it was found that the yield was equal to 14.52% and to prove that the quantification performed was reliable, the method used was validated in accordance with the resolution RE 899/2003 of ANVISA. Then, considering the results of this work, it was found that the yield obtained is promising and the method used is a "green" alternative to the way of obtaining (-)-hinokinin from (-)-cubebin. Key-words: (-)-cubebin; (-)-hinokinin; fungal transformationA (-)-cubebina é uma lignana presente em inúmeras espécies vegetais e possui várias atividades biológicas já descritas, além de ser utilizada como material de partida para a semissíntese de outras lignanas estruturalmente relacionadas, como a (-)-hinoquinina, que se provou ser eficaz contra várias moléstias, destacando- se a atividade tripanocida. Assim, a obtenção da (-)-hinoquinina é promissora, pois os medicamentos atualmente no mercado não são completamente eficazes e ainda são relativamente tóxicos para o paciente. A semissíntese desta substância a partir da (-)-cubebina é, usualmente, catalizada por clorocromato de piridínio, um reagente extremamente tóxico e poluente. Considerando-se, então, que nenhum estudo de obtenção deste composto a partir de métodos biotecnológicos, que são considerados métodos “verdes”, ou seja, promovem a diminuição da geração de resíduos nocivos à saúde dos seres vivos e ao meio ambiente, este trabalho teve como objetivo realizar a biotransformação da (-)-cubebina pelo fungo filamentoso Aspergillus niger, visando a obtenção da (-)-hinoquinina a partir deste processo. Então, primeiramente, isolou-se a (-)- cubebina das sementes secas de Piper cubeba através de métodos cromatográficos e avaliou-se o período necessário para a completa transformação do substrato. Após, realizou-se a biotransformação em escala ampliada e o fracionamento do extrato fúngico obtido da transformação microbiana, por técnicas cromatográficas, para a obtenção da (-)-hinoquinina. A confirmação estrutural deste e da (-)-cubebina foi realizada através de RMN de 1H e 13C. Para a quantificação diária do produto visado, realizou-se a transformação microbiana em escala reduzida e, através de uma metodologia em CLAE, analisou-se diariamente o extrato fúngico obtido após cada dia de biotransformação. Após o período determinado para a transformação de todo o substrato, que foi igual a 14 dias, constatou-se que o rendimento obtido foi igual a 14,52% e, para a comprovação de que a quantificação realizada foi confiável, validou-se o método utilizado de acordo com a resolução RE 899/2003 da ANVISA. Considerando-se então os resultados obtidos deste trabalho, constatou-se que o rendimento obtido é promissor e o método utilizado é uma alternativa “verde” para a forma de obtenção da (-)-hinoquinina a partir da (-)-cubebina. Palavras- chave: (-)-cubebina; (-)-hinoquinina; biotransformação fúngicaUniversidade de FrancaBrasilPós-GraduaçãoPrograma de Mestrado em CiênciasUNIFRANAmbrósio, Sérgio Ricardo7942579499577578http://lattes.cnpq.br/7942579499577578Silva, Márcio Luís Andrade e3379459480976790http://lattes.cnpq.br/3379459480976790Vieira, Paula Bruzadelle8852212520543139http://lattes.cnpq.br/8852212520543139Veneziani, Rodrigo Cassio Sola7198067266796866http://lattes.cnpq.br/7198067266796866Arruda, Caroline2020-08-28T17:53:18Z2020-08-28T17:53:18Z2015-03-09info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesisapplication/pdfARRUDA, Caroline. Obtenção e quantificação de (-)hinoquinina a partir da transformação microbiana da (-)-cubebina por Aspergillus niger. França, 2015. 101 f. Dissertação (Mestrado) - Universidade de Franca. 2015.https://repositorio.cruzeirodosul.edu.br/handle/123456789/972porinfo:eu-repo/semantics/openAccessreponame:Repositório do Centro Universitário Braz Cubasinstname:Centro Universitário Braz Cubas (CUB)instacron:CUB2020-08-28T17:54:19Zoai:repositorio.cruzeirodosul.edu.br:123456789/972Repositório InstitucionalPUBhttps://repositorio.brazcubas.edu.br/oai/requestbibli@brazcubas.edu.bropendoar:2020-08-28T17:54:19Repositório do Centro Universitário Braz Cubas - Centro Universitário Braz Cubas (CUB)false |
dc.title.none.fl_str_mv |
Obtenção e quantificação de (-)-hinoquinina a partir da transformação microbiana da (-)-cubebina por Aspergillus niger Obtainment and quantification of (-)-hinokinin from microbial transformation of (-)-cubebin by Aspergillus niger |
title |
Obtenção e quantificação de (-)-hinoquinina a partir da transformação microbiana da (-)-cubebina por Aspergillus niger |
spellingShingle |
Obtenção e quantificação de (-)-hinoquinina a partir da transformação microbiana da (-)-cubebina por Aspergillus niger Arruda, Caroline (-)-cubebina (-)-hinoquinina Biotransformação fúngica CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
title_short |
Obtenção e quantificação de (-)-hinoquinina a partir da transformação microbiana da (-)-cubebina por Aspergillus niger |
title_full |
Obtenção e quantificação de (-)-hinoquinina a partir da transformação microbiana da (-)-cubebina por Aspergillus niger |
title_fullStr |
Obtenção e quantificação de (-)-hinoquinina a partir da transformação microbiana da (-)-cubebina por Aspergillus niger |
title_full_unstemmed |
Obtenção e quantificação de (-)-hinoquinina a partir da transformação microbiana da (-)-cubebina por Aspergillus niger |
title_sort |
Obtenção e quantificação de (-)-hinoquinina a partir da transformação microbiana da (-)-cubebina por Aspergillus niger |
author |
Arruda, Caroline |
author_facet |
Arruda, Caroline |
author_role |
author |
dc.contributor.none.fl_str_mv |
Ambrósio, Sérgio Ricardo 7942579499577578 http://lattes.cnpq.br/7942579499577578 Silva, Márcio Luís Andrade e 3379459480976790 http://lattes.cnpq.br/3379459480976790 Vieira, Paula Bruzadelle 8852212520543139 http://lattes.cnpq.br/8852212520543139 Veneziani, Rodrigo Cassio Sola 7198067266796866 http://lattes.cnpq.br/7198067266796866 |
dc.contributor.author.fl_str_mv |
Arruda, Caroline |
dc.subject.por.fl_str_mv |
(-)-cubebina (-)-hinoquinina Biotransformação fúngica CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
topic |
(-)-cubebina (-)-hinoquinina Biotransformação fúngica CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
description |
-)-Cubebin is a lignan found in several plant species and has various biological activities already described. In addition, it is used as a starting material for semi-synthesis of other structurally related lignans such as (-) - hinokinin, which is effective against several diseases, highlighting trypanocidal activity. So, the obtainment of this compound is promising based on the fact that the drugs currently on the market are not completely effective and are relatively toxic to the patient. The semi-synthesis of this compound from (-)-cubebin is usually catalyzed by pyridinium chlorochromate, a toxic and polluting reagent. So, due to there being no study of the obtainment of this compound using biotechnological methods, which are considered "green" methods: it promotes the reduction of hazardous wastes to the health of living beings and the environment, this study is aimed at obtaining (-)-hinokinin from biotransformation of (-) - cubebin by Aspergillus niger. So, in the first instance, (-)-cubebin was isolated from dried seeds of Piper cubeba using chromatographic techniques and the time necessary for the complete transformation of the substrate was evaluated. Then, the biotransformation was carried out on a large scale and the extract obtained from fungal transformation was fractionated by chromatographic techniques to obtain (-) - hinokinin. The confirmation of this structure and (-)-cubebin’s was performed by 1H NMR and 13C. For daily quantification of the target product, microbial transformation was performed on small scale and the daily fungal extracts obtained after each day of biotransformation were analysed in HPLC. After the specified period for transformation of the entire substrate, which was equal to 14 days, it was found that the yield was equal to 14.52% and to prove that the quantification performed was reliable, the method used was validated in accordance with the resolution RE 899/2003 of ANVISA. Then, considering the results of this work, it was found that the yield obtained is promising and the method used is a "green" alternative to the way of obtaining (-)-hinokinin from (-)-cubebin. Key-words: (-)-cubebin; (-)-hinokinin; fungal transformation |
publishDate |
2015 |
dc.date.none.fl_str_mv |
2015-03-09 2020-08-28T17:53:18Z 2020-08-28T17:53:18Z |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/masterThesis |
format |
masterThesis |
status_str |
publishedVersion |
dc.identifier.uri.fl_str_mv |
ARRUDA, Caroline. Obtenção e quantificação de (-)hinoquinina a partir da transformação microbiana da (-)-cubebina por Aspergillus niger. França, 2015. 101 f. Dissertação (Mestrado) - Universidade de Franca. 2015. https://repositorio.cruzeirodosul.edu.br/handle/123456789/972 |
identifier_str_mv |
ARRUDA, Caroline. Obtenção e quantificação de (-)hinoquinina a partir da transformação microbiana da (-)-cubebina por Aspergillus niger. França, 2015. 101 f. Dissertação (Mestrado) - Universidade de Franca. 2015. |
url |
https://repositorio.cruzeirodosul.edu.br/handle/123456789/972 |
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por |
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info:eu-repo/semantics/openAccess |
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openAccess |
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application/pdf |
dc.publisher.none.fl_str_mv |
Universidade de Franca Brasil Pós-Graduação Programa de Mestrado em Ciências UNIFRAN |
publisher.none.fl_str_mv |
Universidade de Franca Brasil Pós-Graduação Programa de Mestrado em Ciências UNIFRAN |
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reponame:Repositório do Centro Universitário Braz Cubas instname:Centro Universitário Braz Cubas (CUB) instacron:CUB |
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Centro Universitário Braz Cubas (CUB) |
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Repositório do Centro Universitário Braz Cubas |
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Repositório do Centro Universitário Braz Cubas |
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Repositório do Centro Universitário Braz Cubas - Centro Universitário Braz Cubas (CUB) |
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