Natures chiral catalyst and anti-malarial agent: Isolation and structure elucidation of cinchonine and quinine from cinchona calisaya

  • Carroll A
  • Kavanagh D
  • McGovern F
 et al. 
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Abstract

Nature is a well-recognized source of compounds of interest, but access
is often an issue. One pertinent example is the cinchona alkaloids from
the bark of Cinchona calisaya. In this experiment, students at the
third-year undergraduate level undertake the selective isolation and
characterization of two of the four main alkaloids present in the bark.
Beginning with powdered bark, acid-base extraction, followed by
selective crystallization, serves to yield cinchonine, nature's chiral
catalyst, from the complex mixture. Slow crystallization provides
suitable quality crystals for X-ray analysis. Students readily
appreciate the three-dimensional nature of this chiral catalyst, which
aids subsequent NMR spectroscopic analysis. Manipulation of the mother
liquor by thin-layer and flash column chromatographic techniques proves
a simple but elegant method to furnish quinine, nature's anti-malarial
agent. Both alkaloids are treated to an intensive structure elucidation
workshop comprising 1- and 2-dimensional NMR, infrared, and mass
spectrometry. The method is economical, polished, and robust, bringing
the student on a journey from crude plant material to medicinally
important natural products in three, 2-h laboratory sessions. Moreover,
questions in the student handout and model answers in instructor's
notes, respectively, require that students engage further in topics
associated with the context of this practical.

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Authors

  • Anne Marie Carroll

  • David J. Kavanagh

  • Fiona P. McGovern

  • Joe W. Reilly

  • John J. Walsh

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