STRUCTURAL REASSIGNMENT OF EPIERYTHRATIDINE, AN ALKALOID FROM Erythrinafusca, BASED ON NMR STUDIES AND COMPUTATIONAL METHODS

Journal of The Chilean Chemical Society

SOTO-DELGADO, JORGE¹  ARECHE, CARLOS²  ITURRIAGA-VÁSQUEZ, PATRICIO²  GARCÍA-BELTRÁN, OLIMPO²  CASSELS, BRUCE K² 

[1] Universidad Andres Bello, Santiago, Chile;University of Chile, Santiago, Chile

关键词: Erythrina alkaloids;    Erythrina fusca;    epierythratidine;    1H NMR;    13C NMR;    2D NMR;    GIAO/DFT methods;   

DOI  :  10.4067/S0717-97072012000300027

学科分类：化学（综合）

来源: Sociedad Chilena de Quimica

【 摘 要 】

The diene Erythrina alkaloids erysotrine (1), erysodine (2), erythraline (3), erytharbine (4), and erysotrine N-oxide (5), plus the hydroxylated dihydro derivative of 1, epierythratidine (6) were isolated from seeds of Erythrina fusca Lour., and their 1H and 13C NMR spectra were completely assigned using 2D experiments (H-H COSY, HMQC, HMBC and H-H NOESY). Our assignments for 1-5 agree well with the literature, but the present work shows that the published interpretation of the spectra of 6 must be revised. A combined study based on NMR data and quantum-mechanical calculations using DFT/GIAO indicate that 6 is the correct structure of epierythratidine.

【 授权许可】

Unknown