Penctrimertone, a bioactive citrinin dimer from the endophytic fungus Penicillium sp. T2-11

Fitoterapia. 2020 Oct;146:104711. doi: 10.1016/j.fitote.2020.104711. Epub 2020 Aug 27.

Abstract

Penctrimertone (1), a novel citrinin dimer bearing a 6/6/6/6 tetracyclic ring scaffold, along with two known compounds xerucitrinic acid A (2) and citrinin (3) were isolated from the endophytic fungus Penicillium sp. T2-11. Their structures were unequivocally established by a comprehensive interpretation of the spectroscopic data, with the stereochemistry for 1 was defined by a combination of TDDFT-ECD calculations and the DP4+ probability analysis based on NMR chemical shift calculations. Bioassays revealed that compound 1 exhibited noticeable antimicrobial activities and moderate cytotoxicity. A plausible biosynthetic pathway of 1 was also proposed.

Keywords: Antimicrobial activity; Citrinin dimer; Cytotoxicity; DP4+ analysis; Penicillium sp. T2-11.

MeSH terms

  • Anti-Bacterial Agents / isolation & purification
  • Anti-Bacterial Agents / pharmacology*
  • Antineoplastic Agents / isolation & purification
  • Antineoplastic Agents / pharmacology*
  • Biological Products / isolation & purification
  • Biological Products / pharmacology
  • Cell Line, Tumor
  • Chin
  • Citrinin / isolation & purification
  • Citrinin / pharmacology*
  • Endophytes / chemistry
  • Gastrodia / microbiology*
  • Humans
  • Molecular Structure
  • Penicillium / chemistry*
  • Rhizome / microbiology

Substances

  • Anti-Bacterial Agents
  • Antineoplastic Agents
  • Biological Products
  • Citrinin