Mj. Comin et al., Evaluation of the antiviral activity of natural sulfated polyhydroxysteroids and their synthetic derivatives and analogs, STEROIDS, 64(5), 1999, pp. 335-340
Disodium 3 beta,21-dihydroxypregn-5-en-20-one disulfate (2), sodium 3 beta,
21-dihydroxypregn-5-en-20-one 3-sulfate (3), sodium 3 beta,21-dihydroxypreg
n-5-en-20-one 21-sulfate (4), and disodium 3 beta,6 alpha-dihydroxy-5 alpha
-pregnan-20-one disulfate (6) have been synthesized and completely characte
rized for the first time from readily available materials. Sulfation was pe
rformed using triethylamine-sulfur trioxide complex in dimethylformamide as
the sulfating agent. Selective sulfation of 3 beta,21-dihydroxypregn-5-en-
20-one rendered sodium 3 beta,21-dihydroxypregn-5-en-20-one 3-sulfate (3) a
s the major compound. The synthetic sulfated steroids as well as natural di
sulfated polyhydroxysteroids (7-9) isolated by us from the antarctic ophiur
oid Astrotoma agassizii and the synthetic derivatives disodium 2 beta,3 alp
ha,21-trihydroxy-(20R)-cholesta-5,24-diene 3-acetate, 2,21-disulfate (7a) a
nd 2 beta,3 alpha,21-trihydroxy-(20R)-cholesta-5,24-diene (7b) were compara
tively evaluated for their inhibitory effect on the replication of one DNA
(HSV-2) and two RNA (PV-3, JV) viruses. In general, steroids with sulfate g
roups at C-21 and C-2 or C-3 were the most effective in their inhibitory ac
tion against HSV-2 and also proved to be active against PV-3 and JV. (C) 19
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