Metabólitos especiais isolados das raízes de Andira anthelmia (VELL.) MACBR., Andira fraxinifolia BENTH. (Leguminosae) e das folhas de Palicourea coriacea (Cham.) K. Schum. (Rubiacea)

Abstract

The analysis of fractions obtained by solvent partition and chromatographic tecniques of the extracts from the roots of Andira anthelmia, Andira fraxinifolia (Leguminosae) and from the leaves of Palicourea coriacea (Rubiaceae) led to the isolation of chemical constituents which belong to different classes of special metabolites. From the Andira anthelmia were isolated the ursolic acid, biochanin A (5,7-dihydroxy-4’-methoxyisoflavone), calycosin (4’,7- dihydroxy-3’-methoxyisoflavone), genistein (4’,5,7-trihydroxyisoflavone), biochanin A 7-O- β-D-glucopyranoside, biochanina A 7-O-α-L-rhamnopyranosyl-(1 6)- β-D-glucopyranoside, biochanina A 7-O-β-D-apiofuranosyl-(1 5)-β-D-apiofuranosyl-(1 6)-β-D-glucopyranoside and genistein 7-O-β-D-glucopyiranoside, engeletin (rel-2R,3R-4’,5,7-trihydroxy-3-O-α-Lrhamnopyranosylflavanonol), astilbin (rel-2R,3R-3’,4’,5,7, -tetrahydroxy-3-O-α-Lrhamnopyranosylflavanonol), catechin; p-hydroxybenzoic acid and a cerebroside, 1-O-β−Dglicopyranosyl-2-N(2’-hydroxyacyl-cis-en-amide)-cis-alkenyl-3,4-dihydroxy. From the Andira fraxinifolia were isolated β-sitosterol, stigmasterol, β-amyrin, lupeol, a mixture of 3- β-O-acyl-lupeol esters, betulinic acid, 3-β-O-β-D-glucopyranosylsitosterol, biochanin A, pratesein (3’,5,7-trihydroxy-4’-methoxyisoflavone), isoengeletin (rel-2R,3S-4’,5,7, - trihydroxy-3-O-α-L-rhamnopyranosylflavanonol), isoastilbin (rel-2R,3S-3’,4’,5,7- tetrahydroxy-3-O-α-L-rhamnopyranosylflavanonol) and 5,7-dihydroxy-3-O-α-Lrhamnopyranosylchromone. From the leaves of the Palicourea coriacea were isolated the ursolic acid; the alkaloid calycanthine; allantoin; 2-hydroxy-3-methylanthraquinone; besides the esters, (E) methyl 4-hydroxy-3,5-dimethoxycinnamate, methyl (E)-4-hydroxy-3- methoxycinnamate, methyl (E)-4-hydroxycinnamate, methyl (Z)-4-hydroxycinnamate, methyl-4-hydroxy-3,5-dimethoxybenzoate and methyl-4-methoxybenzoate. The structures were identified by the IR, MS and NMR 1H and 13C spectra data analysis, including special 1D and 2D techniques of the natural substances and some derivatives. The treatment of the isoflavone biochanin A with diazomethane followed by the reaction with I2/KOH in methanol yield two new isoflavone derivatives: rel-2R,3S-2,3,7,4'-tetramethoxy-6,8- diiodineisoflavanone and rel-2R,3S-2,3,7,4'-tetramethoxy-8-iodineisoflavanona. The antihelminthic activity with Andira anthelmia and the antioxidant activity assay with Andira anthelmia and Andira fraxinifolia species were tested