Hyperjaponol H, A New Bioactive Filicinic Acid-Based Meroterpenoid from Hypericum japonicum Thunb. ex Murray

Molecules. 2018 Mar 18;23(3):683. doi: 10.3390/molecules23030683.

Abstract

Hyperjaponol H (1), a new filicinic acid-based meroterpenoid, with a 6/6/10 ring system trans-fused by hetero-Diels-Alder cycloaddition between a germacrane sesquiterpenoid and a filicinic acid moiety, was isolated from aerial parts of Hypericum japonicum. The elucidation of its structure and absolute configuration were accomplished by the analyses of extensive spectroscopic data and the comparison of Cotton effects of electron circular dichroism (ECD) with previously reported ones. The bioactivity assay showed that hyperjaponol H exhibited a moderate inhibitory efficacy on lytic Epstein-Barr virus (EBV) DNA replication in B95-8 cells.

Keywords: Epstein-Barr virus; Hypericum japonicum; meroterpenoid.

MeSH terms

  • Animals
  • Antiviral Agents / pharmacology
  • Butyrophenones / chemistry
  • Butyrophenones / pharmacology*
  • Carbon-13 Magnetic Resonance Spectroscopy
  • Cell Line
  • Cell Survival / drug effects
  • Circular Dichroism
  • Cyclohexenes / chemistry
  • Cyclohexenes / pharmacology*
  • Ganciclovir / pharmacology
  • Herpesvirus 4, Human / drug effects
  • Humans
  • Hypericum / chemistry*
  • Proton Magnetic Resonance Spectroscopy
  • Sesquiterpenes, Germacrane / chemistry
  • Sesquiterpenes, Germacrane / pharmacology*
  • Terpenes / chemistry
  • Terpenes / pharmacology*
  • Virus Replication / drug effects

Substances

  • Antiviral Agents
  • Butyrophenones
  • Cyclohexenes
  • Sesquiterpenes, Germacrane
  • Terpenes
  • hyperjaponol H
  • filicinic acid
  • Ganciclovir