A spiroketal-enol ether derivative from Tanacetum vulgare selectively inhibits HSV-1 and HSV-2 glycoprotein accumulation in Vero cells

Antiviral Res. 2015 Jul:119:8-18. doi: 10.1016/j.antiviral.2015.04.004. Epub 2015 Apr 13.

Abstract

The inhibitory effects of Tanacetum vulgare rhizome extracts on HSV-1 and HSV-2 in vitro replication were assessed. Unlike extracts obtained from the aerial parts, adsorption inhibition and virucidal activities seemed not to be relevant for the observed antiviral action of tansy rhizome extracts. Instead, the most significant effects were the inhibition of virus penetration and a novel mechanism consisting of the specific arrest of viral gene expression and consequently the decrease of viral protein accumulation within infected cells. Through a bioactivity-guided fractionation protocol we isolated and identified the spiroketal-enol ether derivative (E)-2-(2,4-hexadiynyliden)-1,6-dioxaspiro[4.5]dec-3-ene as the active compound responsible for this inhibitory effect.

Keywords: Antiviral; HSV; Rhizome; Spiroketals; Tanacetum; Tansy.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkynes / isolation & purification
  • Alkynes / pharmacology*
  • Animals
  • Chlorocebus aethiops
  • Ether
  • Herpesvirus 1, Human / drug effects*
  • Herpesvirus 1, Human / genetics
  • Herpesvirus 1, Human / metabolism
  • Herpesvirus 2, Human / drug effects*
  • Herpesvirus 2, Human / metabolism
  • Plant Extracts / pharmacology
  • Rhizome / chemistry
  • Spiro Compounds / isolation & purification
  • Spiro Compounds / pharmacology*
  • Tanacetum / chemistry*
  • Vero Cells
  • Viral Envelope Proteins / metabolism*
  • Virus Replication / drug effects
  • Virus Replication / genetics

Substances

  • 2-(2,4-hexadiynylidene)-1,6-dioxaspiro(4.5)dec-3-ene
  • Alkynes
  • Plant Extracts
  • Spiro Compounds
  • Viral Envelope Proteins
  • glycoprotein G, herpes simplex virus type 2
  • glycoprotein gC, herpes simplex virus type 1
  • Ether