Harzianoic acids A and B, new natural scaffolds with inhibitory effects against hepatitis C virus

Bioorg Med Chem. 2019 Feb 1;27(3):560-567. doi: 10.1016/j.bmc.2018.12.038. Epub 2018 Dec 29.

Abstract

Two new sesquiterpene-based analogues, namely harzianoic acids A (1) and B (2), were isolated from a sponge-associated fungus Trichoderma harzianum. Their structures were determined on the basis of the extensive spectroscopic analyses in association with the ECD data for the configurational assignment. Harzianoic acids A and B were structurally characterized as a sesquiterpene and a norsesquiterpene with a cyclobutane nucleus, which is uncommonly found from nature. Both compounds exhibited the inhibitory activity to reduce the HCV RNA levels with low cytotoxicity. The preliminary investigation of the mode of action revealed that the compounds blocked the entry step in the HCV life cycle, while the viral E1/E2 and the host cell CD81 were the potential target proteins.

Keywords: Anti-HCV activity; Fungus; Harzianoic acids A and B; Mode of action; Sesquiterpene; Structural elucidation; Trichoderma harzianum.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antiviral Agents / chemistry
  • Antiviral Agents / isolation & purification
  • Antiviral Agents / pharmacology*
  • Biological Products / chemistry
  • Biological Products / isolation & purification
  • Biological Products / pharmacology*
  • Cell Line, Tumor
  • Cell Survival / drug effects
  • Dose-Response Relationship, Drug
  • Hepacivirus / drug effects*
  • Humans
  • Hydroxybutyrates / chemistry
  • Hydroxybutyrates / isolation & purification
  • Hydroxybutyrates / pharmacology
  • Microbial Sensitivity Tests
  • Models, Molecular
  • Molecular Structure
  • Pyrroles / chemistry
  • Pyrroles / isolation & purification
  • Pyrroles / pharmacology
  • RNA, Viral / drug effects
  • Structure-Activity Relationship
  • Trichoderma / chemistry*

Substances

  • Antiviral Agents
  • Biological Products
  • Hydroxybutyrates
  • Pyrroles
  • RNA, Viral
  • harzianic acid