Antiprotozoal activity of Achillea ptarmica (Asteraceae) and its main alkamide constituents.
In the course of our ongoing screening of plants of the family Asteraceae for antiprotozoal activity, a CH2Cl2-extract from the flowering aerial parts of Achillea ptarmica L. (sneezewort yarrow) was found to be active in vitro against Trypanosoma brucei rhodesiense (IC50 = 0.67 µg/mL) and Plasmodium falciparum (IC50 = 6.6 μg/mL). Bioassay guided fractionation led to the isolation and identification of five alkamides from the most active fractions. Pellitorine and 8,9-Z-dehyropellitorine are the main components of the extract. Beside these olefinic acid amides, four alkamides with diene-diyne structures were isolated. All alkamides were tested for antiprotozoal activity in vitro. Pellitorine was the most active compound so far within this study against P. falciparum (IC50 = 3.3 µg/mL), while 8,9-Z-dehydropellitorine was most active against T. b. rhodesiense (IC50 = 2.0 µg/mL). The activity of pure pellitorine against Plasmodium is higher than that of the crude extract and thus explains the activity of the latter. None of the isolated alkamides, however, was as active against T. b. rhodesiense as the crude extract whose antitrypanosomal activity must therfore be due to a synergistic effect of the isolated compounds or to more active yet to be identified constituents.
Institut für Pharmazeutische Biologie und Phytochemie (IPBP), University of Münster, PharmaCampus, Corrensstraße 48, Münster D-48149, Germany. julia.althaus@uni-muenster.de.
Julia B
JB
Althaus
Swiss Tropical and Public Health Institute (Swiss TPH), Socinstraße 57, Basel CH-4002, Switzerland. Marcel.Kaiser@unibas.ch.
Marcel
M
Kaiser
Swiss Tropical and Public Health Institute (Swiss TPH), Socinstraße 57, Basel CH-4002, Switzerland. Reto.Brun@unibas.ch.
Reto
R
Brun
Institut für Pharmazeutische Biologie und Phytochemie (IPBP), University of Münster, PharmaCampus, Corrensstraße 48, Münster D-48149, Germany. thomschm@uni-muenster.de.
Thomas J
TJ
Schmidt
D031162:Achillea; D000981:Antiprotozoal Agents / Q000737:chemistry* / Q000494:pharmacology*; D005231:Fatty Acids, Unsaturated / Q000032:analysis / Q000494:pharmacology; D020128:Inhibitory Concentration 50; D007893:Leishmania donovani / Q000187:drug effects; D015394:Molecular Structure; D035261:Plant Components, Aerial / Q000737:chemistry; D010936:Plant Extracts / Q000032:analysis / Q000737:chemistry / Q000494:pharmacology; D010963:Plasmodium falciparum / Q000187:drug effects*; D053284:Polyunsaturated Alkamides / Q000032:analysis / Q000494:pharmacology; D014344:Trypanocidal Agents / Q000737:chemistry / Q000494:pharmacology; D016833:Trypanosoma brucei rhodesiense / Q000187:drug effects*; D014349:Trypanosoma cruzi / Q000187:drug effects
D000981:Antiprotozoal Agents; D005231:Fatty Acids, Unsaturated; D010936:Plant Extracts; D053284:Polyunsaturated Alkamides; D014344:Trypanocidal Agents; C008778:pellitorine