Estudo fitoquímico de Zanthoxylum rigidum Humb. Bonpl. ex Willd (Rutaceae), das raízes de Luxemburgia nolilis Eichl (Ochnaceae) e atividades biológicas

Abstract

This work describes the isolation and structural determination of special metabolites isolated from Zanthoxylum rigidum (Rutaceae) (fruits, branches, leaves and roots), collected in the Pantanal mato-grossense, and roots of Luxemburgia nobilis (Ochnaceae), collected in Ouro Preto-MG. From Zanthoxylum rigidum were obtained a mixture of hydrocarbons and mixture of fatty ester, -sitosterol, stigmasterol, campesterol, 3-O- -D-glucopyranosyl sitosterol, arbutin, dimethylmatairesinol, 3",4"-dimethoxybenzyl-3 ', 4 ', 5 '- trimethoxybenzylbutyrolactone, trans and cis-methylpluviatolide, kaerophyllin, methyl (E)-4- hydroxycinnamate, methyl (Z)-4-hydroxycinnamate, methyl 4-hydroxybenzoate, methyl 4- hydroxyphenylacetate, isoquercetin, hesperidin, N-methylatanine, the alkaloid 6- acetonyldihydrochelerythrine, 2 ,3 ,24-trihydroxy-olean-12-en-28-oic acid, and a new cyclopeptide, cyclo(-Phe-Gly-Ala1-Leu-Ala2-), named cyclozanthoxylane A. From the Luxemburgia nobilis were isolated -sitosterol, stigmasterol, campesterol, -sitostenone, 3-O- -D-glucopyranosyl sitosterol, lophirone B, lophirone K and 2",3"-dihydroochnaflavone. The structural determination was based on the 1D and 2D 1H and 13C NMR, high-resolution mass spectroscopy, GC-MS, IR, circular dichroism, used to define the absolute configuration of the lophirone B. The absolute configurations of the amino acids present in the cyclozanthoxylane A were determined by the adapted Marfey method (using the L-FDAA (Na-(2,4-dinitro-5- fluorophenyl)-L-alaninamide) reagent and HPLC analysis. Besides the spectroscopic study of the interaction between the biflavonoide lophirona B and the bovine seric albumine, some biological activity were evaluated, such as antifeedant of Triatomines with N-methylatanine, 6-acetonyldihydrochelerythrine, tripanocidal with 2 ", 3"-dihydroochnaflavone and its methyl derivative, insecticide in Chrysomya putoria with lophirone K, antiviral against Herpes simplex type I and II and adenovirus 19 with N-methylatanine, 2 ", 3"-dihydroochnaflavone and its methyl derivative.