Nature's migraine treatment: isolation and structure elucidation of parthenolide from tanacetum parthenium

• Autores: Emma L. Walsh, Siobhan Ashe, John J. Walsh
• Localización: Journal of chemical education, ISSN 0021-9584, Vol. 89, Nº 1, 2012, págs. 134-137
• Idioma: inglés
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• Resumen

  • The purpose of this experiment is to provide students with the essential skills and knowledge required to perform the extraction, isolation, and structural elucidation of parthenolide from Tanacetum parthenium or feverfew. Students are introduced to a background of the traditional medicinal uses of parthenolide, while more modern applications of parthenolide are also presented. Clinical data supporting the use of feverfew in the treatment of migraine is presented. Methods outlining the accurate extraction and isolation of parthenolide from the powdered, dried flowering tops of feverfew are described. The experiment allows students to acquire and use such skills as extraction, flash column chromatography, and thin-layer chromatography. Structural elucidation is carried out on parthenolide using techniques such as infrared (IR) spectroscopy, high-resolution mass spectrometry (HRMS), and nuclear magnetic resonance (NMR) spectroscopy. Nuclear Overhauser enhancement spectroscopy (NOESY) and X-ray crystallography are employed to establish the three-dimensional conformation of the structure. The student can isolate parthenolide with an approximate yield of 0.2% and the experiment can be completed over two 3-h laboratory sessions. Finally, questions are provided in the student handout, requiring that students engage further in topics associated with the context of this practical.