Application of Lanthanide Shift Reagent to the 1H-NMR Assignments of Acridone Alkaloids

Sio Hong Lam, Hsin Yi Hung, Ping Chung Kuo, Daih Huang Kuo, Fu An Chen, Tian Shung Wu

Research output: Contribution to journalArticlepeer-review

Abstract

This study investigates the application of the paramagnetic shift reagent tris(dipivaloylmethanato)-europium(III) in NMR spectral studies of permethoxyacridone alkaloids (1-3) and pyranoacridone alkaloids (4-6). The induced chemical shifts (∆δ) of all protons were observed for the same molecule, and were compared to deduce the positions resulting from the distance nearby the Eu(dpm)3. Assignment of the H-2, H-4 and H-8 of polysubstituted acridones could be distinguished based on the least-squares method of lanthanide-induced shifts plotted against the mole ratios of Eu(dpm)3 to the substrate. The developed method is not only potentially useful for determining the planar structures of polysubstituted compounds, such as acridones, anthraquinones, xanthones, flavonoids, and phenanthrenes, but also applicable for their stereochemistry.

Original languageEnglish
JournalMolecules (Basel, Switzerland)
Volume25
Issue number22
DOIs
Publication statusPublished - 2020 Nov 17

All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Chemistry (miscellaneous)
  • Molecular Medicine
  • Pharmaceutical Science
  • Drug Discovery
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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