NMR study of fumarprotocetraric acid, a complex lichen depsidone derivative from Cladonia furcata

Bao Ning Su, Muriel Cuendet, Dejan Nikolic, Hördur Kristinsson, Kristín Ingólfsdóttir, Richard B. Van Breemen, Harry H.S. Fong, John M. Pezzuto, A. Douglas Kinghorn*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

11 Citations (Scopus)

Abstract

A lichen depsidone derivative, fumarprotocetraric acid, was obtained as the major constituent of Cladonia furcata (Huds.) Schrad. collected in Iceland. In the 1H NMR spectrum (in DMSO-d6) of this compound, the trans double bond proton signals of the fumaryl unit appeared as overlapping singlets. To confirm the presence of a trans double bond in the molecule, fumarprotocetraric acid was treated with triethylamine. The 1H NMR spectrum of the resultant triethylamine salt displayed a pair of clear doublets with coupling constants of 15.7 Hz, which are characteristic of a trans double bond. Unambiguous 1H and 13C NMR spectral data for both fumarprotocetraric acid and its triethylamine salt were assigned for the first time based on the interpretation of their 2D NMR (HMQC, HMBC and NOESY) spectra.

Original languageEnglish
Pages (from-to)391-394
Number of pages4
JournalMagnetic Resonance in Chemistry
Volume41
Issue number5
DOIs
Publication statusPublished - 1 May 2003

Other keywords

  • 2D NMR
  • C NMR
  • H NMR
  • Cladonia furcata
  • Depsidone derivative
  • Fumarprotocetraric acid
  • Lichen
  • NMR
  • trans double bond
  • Triethylamine salt

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