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
• Autor(a) principal: Santos, Darlisson de Alexandria
• Orientador(a): Alves, Péricles Barreto
• Tipo de documento: Dissertação
• Tipo de acesso: Acesso aberto
• Idioma: por
• Programa de Pós-Graduação: Pós-Graduação em Química
• Palavras-chave em Português: Essências e óleos essenciais; Química orgânica; Aristolóquia; Aristoloquiácea; Aristolochia trilobata; Acetato de sulcatila; Biotransformação
• Palavras-chave em Inglês: Aristolochia trilobata; Essential oil; Sulcatyl acetate; Biotransformation
• Área do conhecimento CNPq: CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
• Link de acesso: https://ri.ufs.br/handle/riufs/6035

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.