Depsides: lichen metabolites active against hepatitis C virus

PloS One
Thi Huyen VuJacques Le Seyec

Abstract

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 atranorin-related structures. Most of these compounds were active against HCV, with a half-maximal inhibitory concentration of about 10 to 70 µM, 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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Citations

Jan 13, 2017·Journal of Natural Products·Claudia CarpentierNormand Voyer
Mar 4, 2021·Natural Product Research·Nguyen-Kim-Tuyen PhamThuc-Huy Duong
Mar 7, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Marwa KerbouaJesus Miguel Lopez Rodilla

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Methods Mentioned

BETA
column chromatography
NMR

Software Mentioned

ALOGPS
GraphPad Prism

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