Evaluation of the antiviral activity of natural sulfated polyhydroxysteroids and their synthetic derivatives and analogs

Citation
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
Citations number
17
Categorie Soggetti
Biochemistry & Biophysics
Journal title
STEROIDS
ISSN journal
0039128X → ACNP
Volume
64
Issue
5
Year of publication
1999
Pages
335 - 340
Database
ISI
SICI code
0039-128X(199905)64:5<335:EOTAAO>2.0.ZU;2-U
Abstract
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 99 Elsevier Science Inc. All rights reserved.