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Chemical Constituents of the Bark of Dipteryx alata Vogel, an Active Species against Bothrops jararacussu Venom
Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Campus "Miguel de Unamuno", Salamanca University, E-37007 Salamanca, Spain
Sorocaba University, UNISO, Rodovia Raposo Tavares km 92.5, 18023-000, Sorocaba, SP, Brazil
Methodist University of Piracicaba, Rodovia do Açúcar km 156, 13400-911, Piracicaba, SP, Brazil
Federal University of Tocantins, Av. NS 15 ALC NO 14, 109 Norte, 77001-090, Porto Nacional, TO, Brazil
* Author to whom correspondence should be addressed.
Received: 25 September 2010; in revised form: 4 November 2010 / Accepted: 10 November 2010 / Published: 12 November 2010
Abstract: 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, 1D- and 2D-NMR techniques.
Keywords: Dipteryx alata; Leguminosae-Papilionoideae; isoflavone; Bothrops jararacussu; snake venom; neutralization
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Puebla, P.; Oshima-Franco, Y.; Franco, L.M.; Santos, M.G.D.; Silva, R.V.; Rubem-Mauro, L.; Feliciano, A.S. Chemical Constituents of the Bark of Dipteryx alata Vogel, an Active Species against Bothrops jararacussu Venom. Molecules 2010, 15, 8193-8204.
Puebla P, Oshima-Franco Y, Franco LM, Santos MGD, Silva RV, Rubem-Mauro L, Feliciano AS. Chemical Constituents of the Bark of Dipteryx alata Vogel, an Active Species against Bothrops jararacussu Venom. Molecules. 2010; 15(11):8193-8204.
Puebla, Pilar; Oshima-Franco, Yoko; Franco, Luiz M.; Santos, Marcio G. Dos; Silva, Renata V. da; Rubem-Mauro, Leandro; Feliciano, Arturo San. 2010. "Chemical Constituents of the Bark of Dipteryx alata Vogel, an Active Species against Bothrops jararacussu Venom." Molecules 15, no. 11: 8193-8204.