Structural reassignment of epierythratidine, an alkaloid from Erythrina fusca, based on NMR studies and computational methods

Olimpo García-Beltrán, Jorge Soto-Delgado, Patricio Iturriaga-Vásquez, Carlos Areche, Bruce K. Cassels

Resultado de la investigación: Article

3 Citas (Scopus)

Resumen

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.

Idioma originalEnglish
Páginas (desde-hasta)1323-1327
Número de páginas5
PublicaciónJournal of the Chilean Chemical Society
Volumen57
N.º3
EstadoPublished - 2012

Huella dactilar

Computational methods
Alkaloids
Nuclear magnetic resonance
Discrete Fourier transforms
Oxides
Seed
Derivatives
Experiments
vitamin B 12 factor III
erythraline
erysodine

ASJC Scopus subject areas

  • Chemistry(all)

Citar esto

García-Beltrán, Olimpo ; Soto-Delgado, Jorge ; Iturriaga-Vásquez, Patricio ; Areche, Carlos ; Cassels, Bruce K. / Structural reassignment of epierythratidine, an alkaloid from Erythrina fusca, based on NMR studies and computational methods. En: Journal of the Chilean Chemical Society. 2012 ; Vol. 57, N.º 3. pp. 1323-1327.
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title = "Structural reassignment of epierythratidine, an alkaloid from Erythrina fusca, based on NMR studies and computational methods",
abstract = "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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Structural reassignment of epierythratidine, an alkaloid from Erythrina fusca, based on NMR studies and computational methods. / García-Beltrán, Olimpo; Soto-Delgado, Jorge; Iturriaga-Vásquez, Patricio; Areche, Carlos; Cassels, Bruce K.

En: Journal of the Chilean Chemical Society, Vol. 57, N.º 3, 2012, p. 1323-1327.

Resultado de la investigación: Article

TY - JOUR

T1 - Structural reassignment of epierythratidine, an alkaloid from Erythrina fusca, based on NMR studies and computational methods

AU - García-Beltrán, Olimpo

AU - Soto-Delgado, Jorge

AU - Iturriaga-Vásquez, Patricio

AU - Areche, Carlos

AU - Cassels, Bruce K.

PY - 2012

Y1 - 2012

N2 - 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.

AB - 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.

KW - 2D NMR

KW - C NMR

KW - H NMR

KW - Epierythratidine

KW - Erythrina alkaloids

KW - Erythrina fusca

KW - GIAO/DFT methods

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JO - Journal of the Chilean Chemical Society

JF - Journal of the Chilean Chemical Society

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