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

Research output: Contribution to journalArticlepeer-review

8 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)1323-1327
Number of pages5
JournalJournal of the Chilean Chemical Society
Volume57
Issue number3
DOIs
Publication statusPublished - 2012

Keywords

  • 2D NMR
  • Epierythratidine
  • Erythrina alkaloids
  • Erythrina fusca
  • GIAO/DFT methods

ASJC Scopus subject areas

  • Chemistry(all)

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