Structurally various p-terphenyls with neuraminidase inhibitory from a sponge derived fungus Aspergillus sp. SCSIO41315

Bioorg Chem. 2023 Mar:132:106357. doi: 10.1016/j.bioorg.2023.106357. Epub 2023 Jan 11.

Abstract

Guided by Global Natural Products Social molecular networking, 14 new p-terphenyl derivatives, asperterphenyls A-N (1-14), together with 20 known p-terphenyl derivatives (15-34), were obtained from a sponge derived fungus Aspergillus sp. SCSIO41315. Among them, new compounds 2-8 and 15-17 were ten pairs of enantiomers. Comprehensive methods such as chiral-phase HPLC analysis, ECD calculations and X-ray diffraction analysis were applied to determine the absolute configurations. Asperterphenyls B (2) and C (3) represented the first reported natural p-terphenyl derivatives possessing a dicarboxylic acid system. Asperterphenyl A (1) displayed neuraminidase inhibitory activity with an IC50 value of 1.77 ± 0.53 µM and could efficiently inhibit infection of multiple strains of H1N1 with IC50 values from 0.67 ± 0.28 to 1.48 ± 0.60 µM through decreasing viral plaque formation in a dose-dependent manner, which suggested that asperterphenyl A (1) might be exploited as a potential antiviral compound in the pharmaceutical fields.

Keywords: Antiviral effects; Aspergillus sp.; Neuraminidase inhibitory activity; P-Terphenyls; Sponge derived fungus.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aspergillus
  • Crystallography, X-Ray
  • Fungi
  • Influenza A Virus, H1N1 Subtype*
  • Molecular Structure
  • Neuraminidase
  • Terphenyl Compounds* / pharmacology

Substances

  • Neuraminidase
  • Terphenyl Compounds