Synthesis and anti-influenza virus evaluation of triterpene-sialic acid conjugates

Bioorg Med Chem. 2018 Jan 1;26(1):17-24. doi: 10.1016/j.bmc.2017.09.038. Epub 2017 Oct 3.

Abstract

We are interested in new non-natural glycosides with sialic acid conjugates and their biological activities. We report the synthesis of eleven non-natural occurring glycosides, which are triterpene (glycyrrhetinic acid and its derivatives)-sialic acid conjugates, and their inhibitory activities against influenza virus sialidases and influenza virus multiplication in MDCK host cells. Deoxoglycyrrhetol-sialic acid conjugates (6d and 6e) and oleanolic acid-sialic acid conjugates (7d and 7e) showed strong inhibitory activities against three subtypes of influenza virus sialidases. These four compounds (6d, 6e, 7d and 7e) showed clear inhibition to influenza virus multiplication but not to MDCK host cell survival.

Keywords: Anti-influenza virus; Glycyrrhetinic acid; Sialic acid; Sialidase; Triterpene.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antiviral Agents / chemical synthesis
  • Antiviral Agents / chemistry
  • Antiviral Agents / pharmacology*
  • Cell Survival / drug effects
  • Chickens
  • Dogs
  • Dose-Response Relationship, Drug
  • Madin Darby Canine Kidney Cells
  • Microbial Sensitivity Tests
  • Molecular Structure
  • N-Acetylneuraminic Acid / chemistry
  • N-Acetylneuraminic Acid / pharmacology*
  • Orthomyxoviridae / drug effects*
  • Structure-Activity Relationship
  • Triterpenes / chemistry
  • Triterpenes / pharmacology*

Substances

  • Antiviral Agents
  • Triterpenes
  • N-Acetylneuraminic Acid