Obtenção e quantificação de (-)-hinoquinina a partir da transformação microbiana da (-)-cubebina por Aspergillus niger

• Ano de defesa: 2015
• Autor(a) principal: Arruda, Caroline
• Tipo de documento: Dissertação
• Tipo de acesso: Acesso aberto
• Idioma: por
• Instituição de defesa: Universidade de Franca; Brasil; Pós-Graduação; Programa de Mestrado em Ciências; UNIFRAN
• Palavras-chave em Português: (-)-cubebina; (-)-hinoquinina; Biotransformação fúngica; CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
• Link de acesso: https://repositorio.cruzeirodosul.edu.br/handle/123456789/972

-)-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