{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,24]],"date-time":"2026-09-24T04:28:19Z","timestamp":1790224099647,"version":"4.1.0"},"reference-count":17,"publisher":"MDPI AG","issue":"5","license":[{"start":{"date-parts":[[2017,5,12]],"date-time":"2017-05-12T00:00:00Z","timestamp":1494547200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>In our ongoing study to evaluate the antiprotozoal activity of alkamides from Asteraceae, a dichloromethane extract from the roots of Anacyclus pyrethrum L. showed a moderate in vitro activity against the NF54 strain of Plasmodium falciparum and against Leishmania donovani (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, 1), deca-2E,4E-dienoic acid isobutylamide (pellitorine, 2), deca-2E,4E,9-trienoic acid isobutylamide (3), deca-2E,4E-dienoic acid 2-phenylethylamide (4), undeca-2E,4E-dien-8,10-diynoic acid isopentylamide (5), tetradeca-2E,4E,12Z-trien-8,10-diynoic acid isobutylamide (6), and dodeca-2E,4E-dien acid 4-hydroxy-2-phenylethylamide (7). Two compounds\u2014undeca-2E,4E-dien-8,10-diynoic acid 2-phenylethylamide (8) and deca-2E,4E-dienoic acid 4-hydroxy-2-phenylethylamide (9)\u2014were isolated as an inseparable mixture (1:4). Compounds 3, 4, and 5 were isolated from Anacyclus pyrethrum L. for the first time. While compounds 4 and 5 were previously known from the genus Achillea, compound 3 is a new natural product, to the best of our knowledge. All isolated alkamides were tested in vitro for antiprotozoal activity against Plasmodium falciparum, Trypanosoma brucei rhodesiense, Trypanosoma cruzi, and Leishmania donovani and for cytotoxicity against L6 rat skeletal myoblasts.<\/jats:p>","DOI":"10.3390\/molecules22050796","type":"journal-article","created":{"date-parts":[[2017,5,12]],"date-time":"2017-05-12T11:03:53Z","timestamp":1494587033000},"page":"796","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":27,"title":["Alkamides from Anacyclus pyrethrum L. and Their in Vitro Antiprotozoal Activity"],"prefix":"10.3390","volume":"22","author":[{"given":"Julia B.","family":"Althaus","sequence":"first","affiliation":[{"name":"Institut f\u00fcr Pharmazeutische Biologie und Phytochemie (IPBP), University of M\u00fcnster, PharmaCampus, Corrensstra\u00dfe 48, M\u00fcnster D-48149, Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Claudine","family":"Malyszek","sequence":"additional","affiliation":[{"name":"Institut f\u00fcr Pharmazeutische Biologie und Phytochemie (IPBP), University of M\u00fcnster, PharmaCampus, Corrensstra\u00dfe 48, M\u00fcnster D-48149, Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Marcel","family":"Kaiser","sequence":"additional","affiliation":[{"name":"Swiss Tropical and Public Health Institute (Swiss TPH), Socinstra\u00dfe 57, Basel CH-4002, Switzerland"},{"name":"University of Basel, Petersplatz 1, Basel CH-4003, Switzerland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Reto","family":"Brun","sequence":"additional","affiliation":[{"name":"Swiss Tropical and Public Health Institute (Swiss TPH), Socinstra\u00dfe 57, Basel CH-4002, Switzerland"},{"name":"University of Basel, Petersplatz 1, Basel CH-4003, Switzerland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2634-9705","authenticated-orcid":false,"given":"Thomas J.","family":"Schmidt","sequence":"additional","affiliation":[{"name":"Institut f\u00fcr Pharmazeutische Biologie und Phytochemie (IPBP), University of M\u00fcnster, PharmaCampus, Corrensstra\u00dfe 48, M\u00fcnster D-48149, Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2017,5,12]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","unstructured":"Greger, H. (2015). Alkamides: A critical reconsideration of a multifunctional class of unsaturated fatty acid amides. Phytochem. Rev.","DOI":"10.1007\/s11101-015-9418-0"},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"6428","DOI":"10.3390\/molecules19056428","article-title":"Antiprotozoal Activity of Achillea ptarmica (Asteraceae) and Its Main Alkamide Constituents","volume":"19","author":"Althaus","year":"2014","journal-title":"Molecules"},{"key":"ref_3","doi-asserted-by":"crossref","unstructured":"Silveira, N., Saar, J., Santos, A.D.C., Barison, A., Sandjo, L.P., Kaiser, M., Schmidt, T.J., and Biavatti, M.W. (2016). A New Alkamide with an Endoperoxide Structure from Acmella ciliata (Asteraceae) and Its in Vitro Antiplasmodial Activity. Molecules, 21.","DOI":"10.3390\/molecules21060765"},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"131","DOI":"10.1007\/s00606-007-0634-y","article-title":"Phylogeny of southern hemisphere Compositae-Anthemideae based on nrDNA ITS and cpDNA ndhF sequence information","volume":"272","author":"Himmelreich","year":"2008","journal-title":"Plant Syst. Evol."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"89","DOI":"10.3372\/wi.37.37104","article-title":"A new subtribal classification of the tribe Anthemideae (Compositae)","volume":"37","author":"Oberprieler","year":"2007","journal-title":"Willdenowia"},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"59","DOI":"10.1006\/mpev.1999.0714","article-title":"Molecular Phylogeny and Biogeography of Tribe Anthemideae (Asteraceae), Based on Chloroplast Gene ndhF","volume":"15","author":"Watson","year":"2000","journal-title":"Mol. Phylogenet. Evol."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"142","DOI":"10.1055\/s-2007-971296","article-title":"Unges\u00e4ttigte S\u00e4ureamide\u2014Ein chemisches Merkmal der Gattung Achillea","volume":"45","author":"Greger","year":"1982","journal-title":"Planta Med."},{"key":"ref_8","unstructured":"Dantz, J., and Uffenbach, P. (1614). Kr\u00e4uterbuch de\u00df Uralten unnd in aller Welt ber\u00fchmtesten Griechischen Scribenten Pedacii Dioscorides Anazarbaei, Kempfer."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"278","DOI":"10.1016\/j.jep.2010.10.060","article-title":"Malaria in the renaissance: Remedies from European herbals from the 16th and 17th century","volume":"133","author":"Adams","year":"2011","journal-title":"J. Ethnopharmacol."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"205","DOI":"10.3797\/scipharm.1111-13","article-title":"Screening and HPLC-Based Activity Profiling for New Antiprotozoal Leads from European Plants","volume":"80","author":"Zimmermann","year":"2012","journal-title":"Sci. Pharm."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"440","DOI":"10.1055\/s-2006-962768","article-title":"Further Polyenic and Polyynic Carboxamides and Sesamin from Achillea ptarmica","volume":"53","author":"Kuropka","year":"1987","journal-title":"Planta Med."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"2707","DOI":"10.1016\/S0040-4020(01)90557-5","article-title":"13C-NMR and 1H lanthanide induced shifts of naturally occurring alkamides with cyclic amide moieties\u2014Amides from Achillea falcata","volume":"42","author":"Hofer","year":"1986","journal-title":"Tetrahedron"},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"1100","DOI":"10.1021\/np50054a015","article-title":"Highly Unsaturated Isopentyl Amides from Achillea wilhelmsii","volume":"50","author":"Greger","year":"1987","journal-title":"J. Nat. Prod."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"1694","DOI":"10.1002\/cber.19721050525","article-title":"Polyacetylenverbindungen, 206. \u00dcber die Inhaltsstoffe von Anacyclus pyrethrum DC","volume":"105","author":"Jente","year":"1972","journal-title":"Chem. Ber."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"2477","DOI":"10.1039\/j39690002477","article-title":"Amides of vegetable origin. Part XII. A new series of Alka-2,4-dienoic Tyramine-amides from Anacyclus pyrethrum D.C. (Compositae)","volume":"19","author":"Burden","year":"1969","journal-title":"J. Chem. Soc. C"},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"1276","DOI":"10.1002\/cber.19560890531","article-title":"Polyacetylenverbindungen (XVI. Mitteil.) Synthese des Anacyclins","volume":"89","author":"Bohlmannn","year":"1956","journal-title":"Chem. Ber."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"2062","DOI":"10.3390\/molecules14062062","article-title":"Quantitative Structure-Antiprotozoal Activity Relationships of Sesquiterpene Lactones","volume":"14","author":"Schmidt","year":"2009","journal-title":"Molecules"}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/22\/5\/796\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T18:35:36Z","timestamp":1760207736000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/22\/5\/796"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2017,5,12]]},"references-count":17,"journal-issue":{"issue":"5","published-online":{"date-parts":[[2017,5]]}},"alternative-id":["molecules22050796"],"URL":"https:\/\/doi.org\/10.3390\/molecules22050796","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2017,5,12]]}}}