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

Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry
Julia B AlthausThomas J Schmidt

Abstract

In our ongoing study to evaluate the antiprotozoal activity of alkamides from Asteraceae, a dichloromethane extract from the roots of Anacycluspyrethrum L. showed a moderate in vitro activity against the NF54 strain of Plasmodium falciparum and against Leishmaniadonovani (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 Anacycluspyrethrum L. for the first time. While compounds 4 and 5 were previousl...Continue Reading

References

Apr 15, 2000·Molecular Phylogenetics and Evolution·L E WatsonT Boluarte
Oct 1, 1987·Planta medica·G Kuropka, K W Glombitza
Jun 11, 2009·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Thomas J SchmidtReto Brun
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Mar 8, 2012·Scientia pharmaceutica·Stefanie ZimmermannMichael Adams
May 24, 2014·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Julia B AlthausThomas J Schmidt
Jun 15, 2016·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Narjara SilveiraMaique W Biavatti

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Citations

Oct 13, 2017·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Bilal ZulfiqarVicky M Avery
Jun 4, 2019·Frontiers in Pharmacology·Roberval Nascimento Moraes NetoAmanda Silva Dos Santos Aliança

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Methods Mentioned

BETA
column chromatography
NMR

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