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:	GARCÍA-BELTRÁN,OLIMPO, SOTO-DELGADO,JORGE, ITURRIAGA-VÁSQUEZ,PATRICIO, ARECHE,CARLOS, CASSELS,BRUCE K
Lenguaje:	English
Publicado:	Sociedad Chilena de Química 2012
Materias:	Erythrina alkaloids Erythrina fusca epierythratidine ¹H NMR 13C NMR 2D NMR GIAO/DFT methods
Acceso en línea:	http://www.scielo.cl/scielo.php?script=sci_arttext&pid=S0717-97072012000300027
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spelling	oai:scielo:S0717-970720120003000272019-02-19STRUCTURAL REASSIGNMENT OF EPIERYTHRATIDINE, AN ALKALOID FROM Erythrinafusca, BASED ON NMR STUDIES AND COMPUTATIONAL METHODSGARCÍA-BELTRÁN,OLIMPOSOTO-DELGADO,JORGEITURRIAGA-VÁSQUEZ,PATRICIOARECHE,CARLOSCASSELS,BRUCE K Erythrina alkaloids Erythrina fusca epierythratidine ¹H NMR 13C NMR 2D NMR GIAO/DFT 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 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.info:eu-repo/semantics/openAccessSociedad Chilena de QuímicaJournal of the Chilean Chemical Society v.57 n.3 20122012-01-01text/htmlhttp://www.scielo.cl/scielo.php?script=sci_arttext&pid=S0717-97072012000300027en10.4067/S0717-97072012000300027
institution	Scielo Chile
collection	Scielo Chile
language	English
topic	Erythrina alkaloids Erythrina fusca epierythratidine ¹H NMR 13C NMR 2D NMR GIAO/DFT methods
spellingShingle	Erythrina alkaloids Erythrina fusca epierythratidine ¹H NMR 13C NMR 2D NMR GIAO/DFT methods GARCÍA-BELTRÁN,OLIMPO SOTO-DELGADO,JORGE ITURRIAGA-VÁSQUEZ,PATRICIO ARECHE,CARLOS CASSELS,BRUCE K STRUCTURAL REASSIGNMENT OF EPIERYTHRATIDINE, AN ALKALOID FROM Erythrinafusca, BASED ON NMR STUDIES AND COMPUTATIONAL METHODS
description	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.
author	GARCÍA-BELTRÁN,OLIMPO SOTO-DELGADO,JORGE ITURRIAGA-VÁSQUEZ,PATRICIO ARECHE,CARLOS CASSELS,BRUCE K
author_facet	GARCÍA-BELTRÁN,OLIMPO SOTO-DELGADO,JORGE ITURRIAGA-VÁSQUEZ,PATRICIO ARECHE,CARLOS CASSELS,BRUCE K
author_sort	GARCÍA-BELTRÁN,OLIMPO
title	STRUCTURAL REASSIGNMENT OF EPIERYTHRATIDINE, AN ALKALOID FROM Erythrinafusca, BASED ON NMR STUDIES AND COMPUTATIONAL METHODS
title_short	STRUCTURAL REASSIGNMENT OF EPIERYTHRATIDINE, AN ALKALOID FROM Erythrinafusca, BASED ON NMR STUDIES AND COMPUTATIONAL METHODS
title_full	STRUCTURAL REASSIGNMENT OF EPIERYTHRATIDINE, AN ALKALOID FROM Erythrinafusca, BASED ON NMR STUDIES AND COMPUTATIONAL METHODS
title_fullStr	STRUCTURAL REASSIGNMENT OF EPIERYTHRATIDINE, AN ALKALOID FROM Erythrinafusca, BASED ON NMR STUDIES AND COMPUTATIONAL METHODS
title_full_unstemmed	STRUCTURAL REASSIGNMENT OF EPIERYTHRATIDINE, AN ALKALOID FROM Erythrinafusca, BASED ON NMR STUDIES AND COMPUTATIONAL METHODS
title_sort	structural reassignment of epierythratidine, an alkaloid from erythrinafusca, based on nmr studies and computational methods
publisher	Sociedad Chilena de Química
publishDate	2012
url	http://www.scielo.cl/scielo.php?script=sci_arttext&pid=S0717-97072012000300027
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STRUCTURAL REASSIGNMENT OF EPIERYTHRATIDINE, AN ALKALOID FROM Erythrinafusca, BASED ON NMR STUDIES AND COMPUTATIONAL METHODS

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