Journal
PLOS ONE
Volume 10, Issue 3, Pages -Publisher
PUBLIC LIBRARY SCIENCE
DOI: 10.1371/journal.pone.0120405
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Funding
- Biology and Health Federative Research Structure of Rennes (Biosit) [UMS CNRS 3480 / US INSERM 018]
- Comite Grand-Ouest de la Ligue contre le Cancer
- Institute National de la Sante Et de la Recherche Medicale (INSERM)
- Universite de Rennes 1
- Centre National de Recherche Scientifique (CNRS)
- Vietnamese Government (Ministry of Education and Training) [322]
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A thorough phytochemical study of Stereocaulon evolutum was conducted, for the isolation of structurally related atranorin derivatives. Indeed, pilot experiments suggested that atranorin (1), the main metabolite of this lichen, would interfere with the lifecycle of hepatitis C virus (HCV). Eight compounds, including one reported for the first time (2), were isolated and characterized. Two analogs (5, 6) were also synthesized, to enlarge the panel of atra-norin-related structures. Most of these compounds were active against HCV, with a half-maximal inhibitory concentration of about 10 to 70 mu M, with depsides more potent than monoaromatic phenols. The most effective inhibitors (1, 5 and 6) were then added at different steps of the HCV lifecycle. Interestingly, atranorin (1), bearing an aldehyde function at C-3, inhibited only viral entry, whereas the synthetic compounds 5 and 6, bearing a hydroxymethyl and a methyl function, respectively, at C-3 interfered with viral replication.
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