New Glutamine-Containing Azaphilone Alkaloids from Deep-Sea-Derived Fungus Chaetomium globosum HDN151398

Mar Drugs. 2019 Apr 28;17(5):253. doi: 10.3390/md17050253.

Abstract

Three new azaphilone alkaloids containing glutamine residues, namely N-glutarylchaetoviridins A-C (1-3), together with two related compounds (4 and 5) were isolated from the extract of Chaetomium globosum HDN151398, a fungus isolated from a deep-sea sediment sample collected in South China Sea. Their structures were elucidated on the basis of extensive 1D and 2D NMR as well as HRESIMS spectroscopic data and chemical analysis. N-glutarylchaetoviridins A-C (1-3) represent the first class of chaetoviridins characterized by embedded glutamate residues. Amino acids incubation experiments produced five azaphilone laden different amino acids residues (6-10) which indicated that this method can enhanced the structural diversity of this strain by culturing with amino acids. Cytotoxicity of the isolated compounds were evaluated against a panel of human cancer cell lines.

Keywords: Chaetomium globosum; azaphilone alkaloids; cytotoxicity; deep-sea-derived fungus.

MeSH terms

  • Alkaloids / chemistry
  • Alkaloids / isolation & purification
  • Alkaloids / pharmacology*
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / isolation & purification
  • Antineoplastic Agents / pharmacology*
  • Aquatic Organisms / chemistry
  • Benzopyrans / chemistry
  • Benzopyrans / isolation & purification
  • Benzopyrans / pharmacology*
  • Cell Line, Tumor
  • Chaetomium / chemistry*
  • Drug Screening Assays, Antitumor
  • Geologic Sediments / microbiology*
  • Glutamine / chemistry
  • Humans
  • Inhibitory Concentration 50
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Pigments, Biological / chemistry
  • Pigments, Biological / isolation & purification
  • Pigments, Biological / pharmacology*

Substances

  • Alkaloids
  • Antineoplastic Agents
  • Benzopyrans
  • Pigments, Biological
  • azaphilone
  • Glutamine