Journal of Crystallographic and Spectroscopic Research

, Volume 23, Issue 12, pp 1005–1011

X-ray structure and13C NMR assignments of indole alkaloids fromAspidosperma cruenta

  • J. K. Harper
  • N. K. Dalley
  • N. L. Owen
  • S. G. Wood
  • R. G. Gates
Article

Abstract

The leaf tissue ofAspidosperma cruenta was studied for alkaloid content. Two alkaloids were isolated and shown by a combination of MS, X-ray, and high field NMR analysis to be obscurinervine and obscurinervidine. X-ray analysis of obscurinervine provided the first quantitative structural information on this compound. Obscurinervine (C25H30N2O5) crystallized in the monoclinic space groupP21 with unit cell parametersa=12.863(3)Å,b=9.646(2)Å,c=18.484(3)Å,β=105.14(5)°,V=2213.8(8)Å3,Dc=1.316 Mg/m3, andZ=4. The structure was solved by direct methods and refined toR=0.054 for 3468 observed reflections. The 2D INADEQUATE NMR experiment provided the first13C chemical shift assignments for obscurinervine. Nineteen of the 2313C-13C connections present were detected. Corresponding13C assignments for obscurinervidine were made by comparison to the spectrum of obscurinervine. The average natural concentrations of the alkaloids were determined to be 0.780% (obscurinervine) and 0.737% (obscurinervidine) by HPLC analysis. Obscurinervine was tested for antiviral and cytotoxic effects. Noin vitro activity was observed.

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Copyright information

© Plenum Publishing Corporation 1993

Authors and Affiliations

  • J. K. Harper
    • 1
  • N. K. Dalley
    • 1
  • N. L. Owen
    • 1
  • S. G. Wood
    • 2
  • R. G. Gates
    • 2
  1. 1.Department of ChemistryBrigham Young UniversityProvo Utah
  2. 2.Department of Botany and Range ScienceBrigham Young UniversityProvo Utah

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