Egger, M. and Pellett, P. and Nickl, K. and Geiger, S. and Graetz, S. and Seifert, R. and Heilmann, J. and König, B. (2008) Synthesis and Cannabinoid Receptor Activity of Ketoalkenes from Echinacea pallida and Non-natural Analogues. Chem. Eur. J. 14, 10978 - 10984.
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Despite its popularity and widespread use, the efficacy of Echinacea products remains unclear and controversial. Among the various compounds isolated from Echinacea, ketoalkenes and ketoalkenynes exclusively found in the pale purple coneflower (E. pallida) are major components of the extracts. In contrast to E. purpurea alkamides, these compounds have not been synthesized and studied for immunostimulatory effects. We present a practical and useful synthetic approach to the ketoalkenes using palladium-catalyzed cross-coupling reactions and the pharmaceutical results at the human cannabinoid receptors. The synthetic route developed provides overall good yields for the ketoalkenes and is applicable to other natural products with similar 1,4-diene motifs. No significant activity was observed at either receptor, indicating that the ketoalkenes from E. pallida are not responsible for immunomodulatory effects mediated via the cannabinergic system. However, newly synthesized non-natural analogues showed micro-molar potency at both cannabinoid receptors.
|Institutions:||Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Burkhard König|
Chemistry and Pharmacy > Institute of Pharmacy
|Projects:||GRK 760, Graduiertenkolleg Medizinische Chemie|
|Keywords:||cannabinoid receptors · cross-coupling · Echinacea pallida · palladium · total synthesis|
|Subjects:||500 Science > 540 Chemistry & allied sciences|
|Refereed:||Yes, this version has been refereed|
|Created at the University of Regensburg:||Yes|
|Deposited On:||05 Mar 2009 10:55|
|Last Modified:||08 Nov 2010 12:31|