STRUCTURAL REASSIGNMENT OF EPIERYTHRATIDINE, AN ALKALOID FROM Erythrinafusca, BASED ON NMR STUDIES AND COMPUTATIONAL METHODS
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...
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| Autores principales: | , , , , |
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| Lenguaje: | English |
| Publicado: |
Sociedad Chilena de Química
2012
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| Materias: | |
| Acceso en línea: | http://www.scielo.cl/scielo.php?script=sci_arttext&pid=S0717-97072012000300027 |
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| Sumario: | 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. |
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