Depsides: Lichen Metabolites Active against Hepatitis C Virus

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.

In silico and in vitro analysis of small molecules and natural compounds targeting the 3CL protease of feline infectious peritonitis virus

“…We also observed the protease-inhibitory effect of NSC87511 ( Supplementary Table 1) during the FIPV 3CL pro inhibition assay. Stictic acid derivatives and atranorin that were extracted from lichens using acetone could inhibit the replication of hepatitis C virus (Vu et al, 2015). In addition, the stictic acid also exhibited anti-HIV-1 integrase activities, with IC 50 < 50 μM (Neamati et al, 1997).…”

Phytochemical and cytotoxic investigations of the lichen Stereocaulon evolutum Graewe

“…The five known compounds atranorin (1, 6.2 g), atranol (2, 10 mg), lobaric acid (3, 1.2 g), ursolic acid (4, 9.0 mg) and methyl 3'-methyllecanorate (5, 21 mg) were identified by direct comparison of their physical and spectral data in the literature [6,7]. Although the compounds have previously been described in some others species of genus Stereocaulon [4], here, they were reported for the first time in Stereocaulon evolutum (figure 1).…”

Therapeutic Effects of Atranorin towards the Proliferation of Babesia and Theileria Parasites

“…Ranković et al [11] documented the potent antibacterial activity of ATR against the most dangerous respiratory tract bacteria, Staphylococcus aureus, comparable to streptomycin. Moreover, Vu et al [12] revealed that ATR possesses antiviral activity against the hepatitis C virus (HCV) with an IC 50 value equal to 22.3 ± 8.0 µM. ATR also reportedly possesses antimalarial activity toward the chloroquine-resistant W-2 and the CAM10 and SHF4 Plasmodium falciparum isolates [13,14].…”