Computer-Aided 13C NMR Chemical Profiling of Crude Natural Extracts without Fractionation

J Nat Prod. 2017 May 26;80(5):1387-1396. doi: 10.1021/acs.jnatprod.6b01063. Epub 2017 Apr 17.

Abstract

A computer-aided, 13C NMR-based dereplication method is presented for the chemical profiling of natural extracts without any fractionation. An algorithm was developed in order to compare the 13C NMR chemical shifts obtained from a single routine spectrum with a set of predicted NMR data stored in a natural metabolite database. The algorithm evaluates the quality of the matching between experimental and predicted data by calculating a score function and returns the list of metabolites that are most likely to be present in the studied extract. The proof of principle of the method is demonstrated on a crude alkaloid extract obtained from the leaves of Peumus boldus, resulting in the identification of eight alkaloids, including isocorydine, rogersine, boldine, reticuline, coclaurine, laurotetanine, N-methylcoclaurine, and norisocorydine, as well as three monoterpenes, namely, p-cymene, eucalyptol, and α-terpinene. The results were compared to those obtained with other methods, either involving a fractionation step before the chemical profiling process or using mass spectrometry detection in the infusion mode or coupled to gas chromatography.

MeSH terms

  • Alkaloids / analysis*
  • Alkaloids / chemistry
  • Aporphines / chemistry*
  • Carbon-13 Magnetic Resonance Spectroscopy / methods*
  • Cyclohexane Monoterpenes
  • Cymenes
  • Mass Spectrometry
  • Molecular Structure
  • Monoterpenes / analysis*
  • Monoterpenes / chemistry*
  • Peumus / chemistry*
  • Plant Extracts / analysis
  • Plant Extracts / chemistry
  • Plant Leaves / chemistry*

Substances

  • Alkaloids
  • Aporphines
  • Cyclohexane Monoterpenes
  • Cymenes
  • Monoterpenes
  • Plant Extracts
  • 4-cymene
  • isocorydine
  • gamma-terpinene
  • laurotetanine