Investigação da origem biossintética de cromenos e cromanos em Piper aduncum e Peperomia obtusifolia (Piperaceae)

• Ano de defesa: 2014
• Autor(a) principal: Souza Júnior, Amauri Alves de [UNESP]
• Tipo de documento: Dissertação
• Tipo de acesso: Acesso aberto
• Idioma: por
• Instituição de defesa: Universidade Estadual Paulista (Unesp)
• Palavras-chave em Português: Quimica organica; Biossintese; Espectrometria de massa; Metabólitos; Biosynthesis
• Link de acesso: http://hdl.handle.net/11449/110847

Chromanes and chromenes are secondary metabolites commonly found in species of the genera Piper and Peperomia, belonging to the Piperaceae family. They are characterized by the presence of a benzopyran core showing a benzene ring fused to a pyran ring. This class of compounds is pharmacologically important, since they from shown a broad range of biological activities including antifungal, trypanocidal, antioxidant and anti-parasitic. The benzopyrans isolated from Piper and Peperomia species showed diversity biosynthetic pathways, mainly related to the aromatic moieties. The biosynthesis of Piper species involve the shikimic pathway showing as the first precursor the p-hydroxybenzoic acid, whereas in Peperomia species would be operating the route of acetate. The present work aimed to study the biosynthetic relationship of benzopyrans present in Piper aduncum and Peperomia obtusifolia as well as to determine the metabolic dynamics involved in their formation related to metabolic and enzymatic levels, since the chromenes isolated from Piper aduncum describe well-defined circadian rhythm. Studies of circadian rhythm performed in Peperomia obtusifolia, aiming to follow the formation of chromane 3,4 -dihydro- 5 -hydroxy -2 ,7- dimethyl-8- (3-methyl -2- butenyl) -2 - (4 -methyl -1 ,3- pentadienyl )-2H -1- benzopyran carboxylic acid (4) from P. obtusifolia showed no uniform sigmoidal curve, common to the chromenes isolated from Piper aduncum. The accumulation of the chromane 4 showed a maximum at 18:00 pm, but others peaks of the same concentration were observed at 06:00 am and 15:00 pm, corroborating to establish a random pace. To evaluate the biosynthetic origin of the chromane 4, feeding experiments were conducted using a precursor enriched with stable isotopes (ethyl [2-13C ]-sodium acetate) in the leaves of P. obtusifolia. Experiments were performed using seedlings of P. obtusifolia. The enriched extracts...