Main structural and stereochemical aspects of the antiherpetic activity of nonahydroxyterphenoyl-containing C-glycosidic ellagitannins

Chem Biodivers. 2004 Feb;1(2):247-58. doi: 10.1002/cbdv.200490021.


Antiherpetic evaluation of five nonahydroxyterphenoyl-containing C-glycosidic ellagitannins, castalagin (1), vescalagin (2), grandinin (3), roburin B (5), and roburin D (7), was performed in cultured cells against four HSV-1 and HSV-2 strains, two of which were resistant to Acyclovir. All five ellagitannins displayed significant anti-HSV activities against the Acyclovir-resistant mutants, but the monomeric structures 1-3 were more active than the dimers 5 and 7. Vescalagin (2) stands out among the five congeners tested as the most potent and selective inhibitor, with an IC50 value in the subfemtomolar range and a selectivity index 5x10(5) times higher than that of Acyclovir. Molecular modeling was used to provide a rationale for the surprisingly lower activity profile of its epimer castalagin (1). These ellagitannins have promising potential as novel inhibitors in the search for non-nucleoside drugs active against Acyclovir-resistant herpes viruses.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antiviral Agents / chemistry*
  • Antiviral Agents / pharmacology
  • Cattle
  • Cell Line
  • Glycosides / chemistry*
  • Glycosides / pharmacology
  • Herpesvirus 1, Human / drug effects*
  • Herpesvirus 1, Human / physiology
  • Herpesvirus 2, Human / drug effects*
  • Herpesvirus 2, Human / physiology
  • Hydrolyzable Tannins / chemistry*
  • Hydrolyzable Tannins / pharmacology
  • Stereoisomerism


  • Antiviral Agents
  • Glycosides
  • Hydrolyzable Tannins