Reactive oxygen species altering the metabolite profile of the marine-derived fungus Dichotomomyces cejpii F31-1

Nat Prod Res. 2021 Jan;35(1):41-48. doi: 10.1080/14786419.2019.1611816. Epub 2019 Jun 19.

Abstract

To investigate the influence of reactive oxygen species (ROS) on the secondary metabolites of the marine-derived fungus Dichotomomyces cejpii F31-1, hydrogen peroxide (H2O2) was added to the GPY culture medium. The HPLC chromatogram of the EtOAc extract of the culture broth was distinct from that of the H2O2 free GPY medium. Further study of the metabolites in the GPY medium with H2O2 resulted in the discovery of eight known compounds. Among them, (22E)-5α, 8α-epidioxyergosta-6, 22-dien-3β-ol (2) and ergosta-4,6,8(14),22-tetraene-3-one (3) were present in the highest concentration, while ergosterol and diketopiperazines are abundant in the H2O2 free medium. Additionally, a new compound, dichocetide D (1) containing a chlorine element and a known ergosterol (10) were isolated from the H2O2 free medium. (22E)-5α, 8α-epidioxyergosta-6, 22-dien-3β-ol (2) exhibited moderate cytotoxic activity against human prostate cancer cell line LNCaP-C4-2B.

Keywords: Dichotomomyces cejpii; reactive oxygen species; secondary metabolites; steroids.

MeSH terms

  • Animals
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / isolation & purification
  • Antineoplastic Agents / pharmacology*
  • Aspergillus / drug effects
  • Aspergillus / metabolism*
  • Culture Media / chemistry
  • Diketopiperazines / metabolism
  • Drug Screening Assays, Antitumor
  • Ergosterol / isolation & purification
  • Ergosterol / metabolism
  • Ergosterol / pharmacology
  • Humans
  • Hydrogen Peroxide / pharmacology
  • Indoles / chemistry
  • Indoles / metabolism
  • Indoles / pharmacology
  • Male
  • Melanoma / drug therapy
  • Mice
  • Molecular Structure
  • Prostatic Neoplasms / drug therapy
  • Prostatic Neoplasms / pathology
  • Quinazolines / chemistry
  • Quinazolines / metabolism
  • Quinazolines / pharmacology
  • Reactive Oxygen Species / metabolism*
  • Secondary Metabolism

Substances

  • Antineoplastic Agents
  • Culture Media
  • Diketopiperazines
  • Indoles
  • Quinazolines
  • Reactive Oxygen Species
  • fiscalin B
  • Hydrogen Peroxide
  • Ergosterol

Supplementary concepts

  • Aspergillus cejpii