Varilactones and wortmannilactones produced by Penicillium variabile cultured with histone deacetylase inhibitor

Arch Pharm Res. 2018 Jan;41(1):57-63. doi: 10.1007/s12272-017-0982-2. Epub 2017 Nov 9.

Abstract

Seven polyketides, including four new ones named as varilactones A-B (1-2) and wortmannilactones M-N (3-4), as well as three biogenetically related known wortmannilactones E, F and H (5-7), were isolated from the fungus Penicillium variabile HXQ-H-1, cultivated in potato-based medium with the histone deacetylase inhibitor suberoylanilide hydroxamic acid (SAHA). Their structures (1-7) were established by analysis of NMR and MS data, and the absolute configuration of oxabicyclo[2.2.1]heptane unit was deduced from 1H-NMR analyses on MPA esters after chemical reduction reaction. Among them, varilactones A and B (1 and 2), features a novel skeleton with a triene unit linking an oxabicyclo[2.2.1]heptane and an oxabicyclo[3.3.0]octane rings.

Keywords: Epigenetic modification; Penicillium variabile; Polyketides; Suberoylanilide hydroxamic acid.

MeSH terms

  • Cell Line, Tumor
  • HeLa Cells
  • Histone Deacetylase Inhibitors / pharmacology*
  • Histone Deacetylases / metabolism*
  • Humans
  • Influenza A Virus, H1N1 Subtype
  • Molecular Conformation
  • Penicillium / drug effects*
  • Penicillium / enzymology
  • Penicillium / metabolism*
  • Polyketides / chemistry
  • Polyketides / isolation & purification*
  • Polyketides / metabolism*
  • Quantum Theory

Substances

  • Histone Deacetylase Inhibitors
  • Polyketides
  • Histone Deacetylases