Biomimetic reactions using metabolitic metalloporphyrin of secondary metabolite from leaves of Passiflora edulis var. Flavicarpa DEGENER
orientina. isoorientina. Mn(3MeOSalen)Cl. catalisador de Jacobsen.
Orientin and isoorientin are c-glycosidic flavonoids and markers of Passiflora edulis var. flavicarpa and other plant species, which are reported in the literature for their various pharmacological properties. However, all these species have a common problem to other drug candidates that is the scarceness in studies about the metabolism and pharmacokinetics of extracts and especially their markers that are essential to prove the safety and efficacy of these new drug candidates. Since biomimetic model using metalloporphyrins development, biotransformation reactions are simulated to characterize the metabolism in vitro and provide several products that may later be identified as metabolites and help to reduce the number of animals needed at this study stage. Thus, orientin and the isoorientin were isolated by classical column chromatography and HPLC from the P. edulis extract. These flavonoids were submitted to reactions with the oxidants m-CPBA and PhIO and catalyzed by the Jacobsen catalyst (Mn (Salen)), an efficient and easily synthesized and purified, in addition to the synthesized Mn (3MeOSalen) Cl catalyst, derived from Salen still unpublished in biomimetic reactions which was characterized with higher oxidation potential. The isoorientin reaction with m-CPBA in the proportion 1:20:20 (catalyst:oxidant:flavonoid) showed a higher consumption of the substrate for both catalysts while he orientin reaction with PhIO in the proportion 1:10:10 presented a higher consumption of the substrate also for both catalysts. The best condition was optimized showing that the isomers, isoorintin and orintin, present different reactivity. Besides, the reaction products, 3 from orientin and 5 from isoorientin, were characterized by LC-MS and LC-MS / MS. These reaction products have not been found in the literature, however the formation of epoxides that are highly reactive and may cause toxicity is highlighted. Thus, this study can serve as a basis for subsequent pharmacological and toxicological studies that confirm the presence of these compounds as phase I metabolites and ensure the safety of the use of plant products that have isoorientin and orientin as markers.