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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 Anacyclus pyrethrum L. showed a moderate in vitro activity against the NF54 strain of Plasmodium falciparum and against Leishmania donovani (amastigotes, MHOM/ET/67/L...

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Autores principales: Althaus, Julia B., Malyszek, Claudine, Kaiser, Marcel, Brun, Reto, Schmidt, Thomas J.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2017
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6154598/
https://www.ncbi.nlm.nih.gov/pubmed/28498323
http://dx.doi.org/10.3390/molecules22050796
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author Althaus, Julia B.
Malyszek, Claudine
Kaiser, Marcel
Brun, Reto
Schmidt, Thomas J.
author_facet Althaus, Julia B.
Malyszek, Claudine
Kaiser, Marcel
Brun, Reto
Schmidt, Thomas J.
author_sort Althaus, Julia B.
collection PubMed
description 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—undeca-2E,4E-dien-8,10-diynoic acid 2-phenylethylamide (8) and deca-2E,4E-dienoic acid 4-hydroxy-2-phenylethylamide (9)—were 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.
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spelling pubmed-61545982018-11-13 Alkamides from Anacyclus pyrethrum L. and Their in Vitro Antiprotozoal Activity Althaus, Julia B. Malyszek, Claudine Kaiser, Marcel Brun, Reto Schmidt, Thomas J. Molecules Article 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—undeca-2E,4E-dien-8,10-diynoic acid 2-phenylethylamide (8) and deca-2E,4E-dienoic acid 4-hydroxy-2-phenylethylamide (9)—were 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. MDPI 2017-05-12 /pmc/articles/PMC6154598/ /pubmed/28498323 http://dx.doi.org/10.3390/molecules22050796 Text en © 2017 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Althaus, Julia B.
Malyszek, Claudine
Kaiser, Marcel
Brun, Reto
Schmidt, Thomas J.
Alkamides from Anacyclus pyrethrum L. and Their in Vitro Antiprotozoal Activity
title Alkamides from Anacyclus pyrethrum L. and Their in Vitro Antiprotozoal Activity
title_full Alkamides from Anacyclus pyrethrum L. and Their in Vitro Antiprotozoal Activity
title_fullStr Alkamides from Anacyclus pyrethrum L. and Their in Vitro Antiprotozoal Activity
title_full_unstemmed Alkamides from Anacyclus pyrethrum L. and Their in Vitro Antiprotozoal Activity
title_short Alkamides from Anacyclus pyrethrum L. and Their in Vitro Antiprotozoal Activity
title_sort alkamides from anacyclus pyrethrum l. and their in vitro antiprotozoal activity
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6154598/
https://www.ncbi.nlm.nih.gov/pubmed/28498323
http://dx.doi.org/10.3390/molecules22050796
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