Next Article in Journal
Probing Steroidal Substrate Specificity of Cytochrome P450 BM3 Variants
Next Article in Special Issue
In Vitro Reversible and Time-Dependent CYP450 Inhibition Profiles of Medicinal Herbal Plant Extracts Newbouldia laevis and Cassia abbreviata: Implications for Herb-Drug Interactions
Previous Article in Journal
A New Xanthone Glycoside from the Endolichenic Fungus Sporormiella irregularis
Previous Article in Special Issue
In Vitro Activity of Selected West African Medicinal Plants against Mycobacterium ulcerans Disease
Article Menu
Issue 6 (June) cover image

Export Article

Open AccessFeature PaperArticle
Molecules 2016, 21(6), 765; doi:10.3390/molecules21060765

A New Alkamide with an Endoperoxide Structure from Acmella ciliata (Asteraceae) and Its in Vitro Antiplasmodial Activity

1
Departamento de Ciências Farmacêuticas, Centro de Ciências da Saúde, Bloco J/K, Universidade Federal de Santa Catarina, Florianópolis 88040-900, SC, Brazil
2
Institut für Pharmazeutische Biologie und Phytochemie (IPBP), University of Münster, PharmaCampus, Corrensstraße 48, Münster D-48149, Germany
3
Departamento de Química, Universidade Federal do Paraná, Curitiba 81530-900, PR, Brazil
4
Swiss Tropical and Public Health Institute (Swiss TPH), Socinstr. 57, Basel CH-4051, Switzerland
5
University of Basel, Petersplatz 1, Basel CH-4003, Switzerland
*
Authors to whom correspondence should be addressed.
Academic Editor: Dereck J. McPhee
Received: 12 May 2016 / Revised: 1 June 2016 / Accepted: 2 June 2016 / Published: 11 June 2016
View Full-Text   |   Download PDF [1141 KB, uploaded 11 June 2016]   |  

Abstract

From the aerial parts of Acmella ciliata (H.B.K.) Cassini (basionym Spilanthes ciliata Kunth; Asteraceae), three alkamides were isolated and identified by mass- and NMR spectroscopic methods as (2E,6E,8E)-N-isobutyl-2,6,8-decatrienamide (spilanthol, (1)), N-(2-phenethyl)-2E-en-6,8-nonadiynamide (2) and (2E,7Z)-6,9-endoperoxy-N-isobutyl-2,7-decadienamide (3). While 1 and 2 are known alkamides, compound 3 has not been described until now. It was found that the unusual cyclic peroxide 3 exists as a racemate of both enantiomers of each alkamide; the 6,9-cis- as well as the 6,9-trans-configured diastereomers, the former represents the major, the latter the minor constituent of the mixture. In vitro tests for activity against the human pathogenic parasites Trypanosoma brucei rhodesiense and Plasmodium falciparum revealed that 1 and 3 possess activity against the NF54 strain of the latter (IC50 values of 4.5 and 5.1 µM, respectively) while 2 was almost inactive. Compound 3 was also tested against multiresistant P. falciparum K1 and was found to be even more active against this parasite strain (IC50 = 2.1 µM) with considerable selectivity (IC50 against L6 rat skeletal myoblasts = 168 µM). View Full-Text
Keywords: Acmella ciliata; jambu; Asteraceae; antiplasmodial activity; alkamide; endoperoxide; Plasmodium falciparum Acmella ciliata; jambu; Asteraceae; antiplasmodial activity; alkamide; endoperoxide; Plasmodium falciparum
Figures

This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

Supplementary material

Scifeed alert for new publications

Never miss any articles matching your research from any publisher
  • Get alerts for new papers matching your research
  • Find out the new papers from selected authors
  • Updated daily for 49'000+ journals and 6000+ publishers
  • Define your Scifeed now

SciFeed Share & Cite This Article

MDPI and ACS Style

Silveira, N.; Saar, J.; Santos, A.D.C.; Barison, A.; Sandjo, L.P.; Kaiser, M.; Schmidt, T.J.; Biavatti, M.W. A New Alkamide with an Endoperoxide Structure from Acmella ciliata (Asteraceae) and Its in Vitro Antiplasmodial Activity. Molecules 2016, 21, 765.

Show more citation formats Show less citations formats

Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Related Articles

Article Metrics

Article Access Statistics

1

Comments

[Return to top]

Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top