Produção Nacional
Two new prenylated isoflavones from Deguelia costata
2019; Elsevier BV; Volume: 30; Linguagem: Inglês
10.1016/j.phytol.2019.02.018
ISSN1876-7486
AutoresBruno Brito Lemes, Lilian da Silva Miguêz, Rebeca Lopes Santos, João Carlos da Rocha Bastos Serafim, Juliana M. Figueiredo, Islam Farias Tavares, Madson de Godoi Pereira, Edson de Jesus Marquês, Florisvaldo da Silva Ramos, Ramon dos Santos El-Bachá, Alany Ingrid Ribeiro, Maria Fátima das Graças Fernandes da Silva, Lourdes Cardoso de Souza Neta,
Tópico(s)Biological Activity of Diterpenoids and Biflavonoids
ResumoPhytochemical investigation of the roots, leaves and stems of Deguelia costata resulted in the isolation of two new prenylated isoflavones, 5,5"-dihydroxy-4'-methoxy-6",6"-dimethyl-4",5"-dihydropyrano [2",3":7,8]isoflavone (1), and 5-hydroxy-4'-methoxy-5"-hydroxyisopropyl-4",5"-dihydrofurano[2",3":7,8]isoflavone (2), together with nine known compounds, 4'-O-methylderrone (3), 4'-O-methylalpinumisoflavone (4); 5-hydroxy-3',4'-dimethoxy-2",2"-dimethylpyrano[5",6":7,6]isoflavone (5), gancaonin M (6), robustin (7), isorobustin (8), scandenin (9), lupeol (10), and betulinic acid (11). The structures of 1 and 2 were determined by analyses of their spectroscopic data [1H, 13C NMR, HSQC and HMBC] and mass spectrometry. The cytotoxicity of 4'-methylderrone (3), scandenin (9), lupeol (10), and betulinic acid (11) were evaluated on C6 glioma cells. Among them, betulinic acid (11) presented a cytotoxic effect on rat C6 glioma cells with an IC50 value of 38.0 μM. The total flavonoid content of dichloromethane extract from leaves, the most enriched in isoflavones, was obtained using the AlCl3 method (80.07 ± 1.55 μg Quercetin g−1 dry extract). This new study reveals the potential of D. costata as a source of new isoflavones, as well as the promising cytotoxic effect of betulinic acid on C6 glioma cells.
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