The diene Erythrina alkaloids erysotrine (1), erysodine (2), erythraline (3), erytharbine (4), and erysotrine N-oxide (5), plus the hydroxylated dihydro derivative of I, epierythratidine (6) were isolated from seeds of Erythrina fusca Lour., and their H-1 and C-13 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.
%0 Journal Article
%1 RN71
%A Garcia-Beltran, O.
%A Soto-Delgado, J.
%A Iturriaga-Vasquez, P.
%A Areche, C.
%A Cassels, B.K.
%D 2012
%J Journal of the Chilean Chemical Society
%K 2d alkaloids, c-13 chemical-shifts, configuration, dqcauchile elucidation, epierythratidine, erythrina fusca, giao, giao/dft h-1 methods, nmr, spectroscopy
%N 3
%P 1323-1327
%R 10.4067/S0717-97072012000300027
%T Structural Reassignment of Epierythratidine, an Alkaloid from Erythrina Fusca, Based on Nmr Studies and Computational Methods
%U /brokenurl#<Go to ISI>://WOS:000309315300027
%V 57
%X The diene Erythrina alkaloids erysotrine (1), erysodine (2), erythraline (3), erytharbine (4), and erysotrine N-oxide (5), plus the hydroxylated dihydro derivative of I, epierythratidine (6) were isolated from seeds of Erythrina fusca Lour., and their H-1 and C-13 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.
@article{RN71,
abstract = {The diene Erythrina alkaloids erysotrine (1), erysodine (2), erythraline (3), erytharbine (4), and erysotrine N-oxide (5), plus the hydroxylated dihydro derivative of I, epierythratidine (6) were isolated from seeds of Erythrina fusca Lour., and their H-1 and C-13 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.},
added-at = {2019-12-04T03:57:35.000+0100},
author = {Garcia-Beltran, O. and Soto-Delgado, J. and Iturriaga-Vasquez, P. and Areche, C. and Cassels, B.K.},
biburl = {https://www.bibsonomy.org/bibtex/29759cb24334f7c9b583fb488c6c4cc4f/dqcauchile},
doi = {10.4067/S0717-97072012000300027},
interhash = {8780ec71e6871bcf88727f2d6e326fd2},
intrahash = {9759cb24334f7c9b583fb488c6c4cc4f},
issn = {0717-9707},
journal = {Journal of the Chilean Chemical Society},
keywords = {2d alkaloids, c-13 chemical-shifts, configuration, dqcauchile elucidation, epierythratidine, erythrina fusca, giao, giao/dft h-1 methods, nmr, spectroscopy},
number = 3,
pages = {1323-1327},
timestamp = {2019-12-04T03:58:17.000+0100},
title = {Structural Reassignment of Epierythratidine, an Alkaloid from Erythrina Fusca, Based on Nmr Studies and Computational Methods},
type = {Journal Article},
url = {/brokenurl#<Go to ISI>://WOS:000309315300027},
volume = 57,
year = 2012
}