Liver Enzyme-Mediated Oxidation of Echinacea purpurea Alkylamides: Production of Novel Metabolites and Changes in Immunomodulatory Activity

UNCG Author/Contributor (non-UNCG co-authors, if there are any, appear on document)
Nadja B. Cech, Patricia A. Sullivan Distinguished Professor of Chemistry (Creator)
Gregory M. Raner, Associate Professor and Graduate Director (Creator)
The University of North Carolina at Greensboro (UNCG )
Web Site:

Abstract: The medicinal plant Echinacea is widely used to treat upper respiratory infections and is reported to stimulate the human immune system. A major constituent class of Echinacea, the alkyl-amides, has immunomodulatory effects. Recent studies show that alkylamides are oxidized by cytochrome P450 enzymes, but the immunomodulatory activity of these products is unknown. The objectives of this study were to characterize the products formed by incubation of an Echinacea extract and an isolated alkylamide with human liver microsomes, and to evaluate the influence of Echinacea alkylamides and metabolites on cytokine production by Jurkat human T cells. A novel class of carboxylic acid alkylamide metabolites was identified and shown to be the major constituents present after 2-h incubation of alkylamides with human liver microsomes. Echinacea alkylamides suppressed 1L-2 secretion by stimulated T cells, and this effect was significantly lessened upon oxidation of the alkylamides to carboxylic acids and hydroxylated metabolites. These findings highlight the importance of considering the influence of liver enzyme metabolism when evaluating the immunomodulatory effects of alkyl-amides.

Additional Information

Planta Medica, 72(15), 1372-1377 (2006).
Language: English
Date: 2006
Echinacea purpurea Asteraceae, alkylamides, alkamides, cytochrome P450, metabolism, T-lymphocytes, interleukin-2 (IL-2)

Email this document to