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  • Modifications of the chemical structure of terpenes in antiplasmodial and antifungal drug research.

Modifications of the chemical structure of terpenes in antiplasmodial and antifungal drug research.

Bioorganic & medicinal chemistry letters (2007-10-02)
David Olagnier, Philippe Costes, Antoine Berry, Marie-Denise Linas, Martine Urrutigoity, Odile Dechy-Cabaret, Françoise Benoit-Vical
ABSTRACT

Pure natural monoterpenes were evaluated in vitro for their antiplasmodial activities against Plasmodium falciparum. Chemically modified terpenes were also tested to see whether the introduction of an alkyne, a cyclopropane, a diene, or a cyclopentenone moiety had an influence on the biological activity. The IC(50) obtained on a chloroquine-resistant strain of Plasmodium (FcM29-Cameroon) showed moderate activity, but with the alkyne and the cyclopentenone derivatives showing a promising enhancement of activity compared with the parent molecules. On the contrary, no antifungal activity was found in vitro using Candida albicans. Given the observed antiplasmodial activity of some of these modified monoterpenes, new monoterpene derivatives could be the basis for new antimalarial drugs to be researched.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
(−)-Isopulegol, 99%
Sigma-Aldrich
(R)-(+)-Limonene, 97%
Sigma-Aldrich
(R)-(+)-Limonene, technical, ~90% (sum of enantiomers, GC)
Supelco
Geraniol, analytical standard
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Linalool, ≥97%, FCC, FG
Supelco
(R)-(+)-Limonene, analytical standard
Sigma-Aldrich
(−)-Isopulegol, ≥98%
Sigma-Aldrich
Geraniol, ≥97%, FCC, FG
Sigma-Aldrich
Geraniol, natural, ≥97%, FG
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Geraniol, 98%
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Linalool, 97%
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(S)-(−)-Perillyl alcohol, 96%
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5-Fluorocytosine, nucleoside analog
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β-Citronellol, 95%
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Citronellol, ≥95%, FCC, FG
Sigma-Aldrich
(S)-(−)-Perillyl alcohol, ≥95%, FG