Chemical Constituents of the Bark of Dipteryx alata Vogel, an Active Species against Bothrops jararacussu Venom.

The effect of four sub-extracts prepared from the lyophilized hydroalcoholic bark of Dipteryx alata (Leguminosae-Papilionoideae) dissolved in a methanol-water (80:20) mixture through a liquid-liquid partition procedure has been investigated against the neuromuscular blockade of the venom of the snake Bothrops jararacussu. The active CH2Cl2 sub-extract has been extensively analyzed for its chemical constituents, resulting in the isolation of four lupane-type triterpenoids: lupeol (1), lupenone (2), 28-hydroxylup-20(29)-en-3-one (3), betulin (4), nine isoflavonoids: 8-O-methylretusin (5), 7-hydroxy- 5,6,4′-trimethoxyisoflavone (6), afrormosin (8), 7-hydroxy-8,3′,4′-trimethoxyisoflavone (9), 7,3′-dihydroxy-8,4′-dimethoxyisoflavone (10), odoratin (11), 7,8,3′-trihydroxy-4′-methoxyisoflavone (13), 7,8,3′-trihydroxy-6,4′-dimethoxyisoflavone (15), dipteryxin (17), one chalcone: isoliquiritigenin (7), one aurone: sulfuretin (14) and three phenolic compounds: vanillic acid (12), vanillin (16), and protocatechuic acid (18). Their chemical structures were elucidated on the basis of spectroscopic analysis, including HRMS, 1Dand 2D-NMR techniques. [ABSTRACT FROM AUTHOR]