The antiviral activities of some naturally occurring anthraquinones, b
ianthrones, and hypericin derivatives were compared by the end-point C
PE (viral cytopathic effects) method and plaque assays. Under optimal
conditions of exposure to light, hypericin, 7,7'-dichlorohypericin and
5,7-dichloroemodin exhibited strong inhibitory activity against HSV-1
(herpes simplex virus type 1) in both assays. Partial inactivation of
the virus was shown by emodin, 7-chloroemodin and 7-chloro-1-O-methyl
emodin; the bianthrones and other anthraquinones were found to be inac
tive. Antiviral activity appeared to be positively correlated with inc
reasing substitution of chlorine in the anthraquinone structure. In th
e absence of light, only hypericin and 7,7'-dichlorohypericin displaye
d detectable activity.