REAÇÕES BIOMIMÉTICAS COM METALOPORFIRINAS DE METABÓLITOS SECUNDÁRIOS DAS FOLHAS DE Passiflora edulis var. Flavicarpa DEGENER
Passiflora edulis var. flavicarpa. Isoorientin. Biomimetic oxidation. Salen Catalyst.
Passiflora edulis var. flavicarpa Degener is a plant species popularly known in Brazil as passion fruit and has its widespread use in folk medicine for the treatment of neurological disorders, as well as its proven efficacy against various disorders, which shows its potential for the formulation of herbal medicines. However, the development of an herbal medicine involves several steps, including metabolism and pharmacokinetic studies. Through the biomimetic model with metalloporphyrins, the biotransformation reactions are simulated to characterize the metabolism in vitro and provide several products, which can be subsequently identified as metabolites. Thus, from the extract of P. edulis, through the techniques of column chromatography and HPLC, isoorientin, a flavonoid described in the literature as majority for the species, was isolated. The isoorientin was submitted to reactions catalyzed by the Salen catalyst, and one of its derivatives, the Mn(3-MeOSalen)Cl catalyst, which has not been reported yet in the literature for its use in biomimetic oxidation studies. Three oxidants were tested: PhIO, PhI(OAc2) and mCPBA. The catalyst/oxidant/substrate molar ratios used to perform the assays were 1:10:10, 1:20:20, and 1:30:30. The reaction with m-CPBA at the 1:20:20 ratio showed a higher consumption of the substrate, 61.17% and 60.67% for the Salen catalyst and the Mn-(3-MeOSalen)-Cl after 3 hours of reaction, respectively. The kinetics of the isoorientin oxidation was calculated, demonstrating that it obeys the second-order reaction. Qualitatively, in all the conditions tested for the Salen catalyst, the same products were formed, while for the Mn-(3-MeOSalen)-Cl catalyst a difference was observed when the different oxidants were tested. These results may serve as the basis for the study with other metalloporphyrins, and also to evaluate the safety and efficacy of natural products with potential for the development of herbal medicines.