Alkamides from Anacyclus pyrethrum L. and Their in Vitro Antiprotozoal Activity.

In our ongoing study to evaluate the antiprotozoal activity of alkamides from Asteraceae, a dichloromethane extract from the roots of L. showed a moderate in vitro activity against the NF54 strain of and against (amastigotes, MHOM/ET/67/L82 strain). Seven pure alkamides and a mixture of two further alkamides were isolated by column chromatography followed by preparative high performance liquid chromatography. The alkamides were identified by mass- and NMR-spectroscopic methods as tetradeca-2E,4E-dien-8,10-diynoic acid isobutylamide (anacycline, ), deca-2,4-dienoic acid isobutylamide (pellitorine, ), deca-2,4,9-trienoic acid isobutylamide (), deca-2,4-dienoic acid 2-phenylethylamide (), undeca-2,4-dien-8,10-diynoic acid isopentylamide (), tetradeca-2,4,12-trien-8,10-diynoic acid isobutylamide (), and dodeca-2,4-dien acid 4-hydroxy-2-phenylethylamide (). Two compounds-undeca-2,4-dien-8,10-diynoic acid 2-phenylethylamide () and deca-2,4-dienoic acid 4-hydroxy-2-phenylethylamide ()-were isolated as an inseparable mixture (1:4). Compounds , , and were isolated from L. for the first time. While compounds and were previously known from the genus , compound is a new natural product, to the best of our knowledge. All isolated alkamides were tested in vitro for antiprotozoal activity against , , , and and for cytotoxicity against L6 rat skeletal myoblasts.