Two new prenylated isoflavones from Deguelia costata

Publication date: April 2019Source: Phytochemistry Letters, Volume 30Author(s): Bruno Brito Lemes, Lilian da Silva Miguêz, Rebeca Lopes Santos, João Carlos da Rocha Bastos Serafim, Juliana Medrado Ribeiro Figueiredo, Islam Farias Tavares, Madson de Godoi Pereira, Edson de Jesus Marquês, Florisvaldo da Silva Ramos, Ramon Santos El-Bachá, Alany Ingrid Ribeiro, Maria Fátima das Graças Fernandes da Silva, Lourdes Cardoso de Souza NetaAbstractPhytochemical 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 ext...
Source: Phytochemistry Letters - Category: Chemistry Source Type: research