New asymmetrical bispyrrolidinoindoline diketopiperazines from the marine fungus Aspergillus sp. DX4H

Nat Prod Res. 2018 Apr;32(7):815-820. doi: 10.1080/14786419.2017.1363752. Epub 2017 Aug 8.

Abstract

Known diketopiperazine WIN 64821 and its asymmetric stereoisomers (1-3) had been isolated from the culture broth of a marine gut fungus Aspergillus sp. DX4H. The planar and stereochemistry for new compounds were determined by a suite of techniques including mass, NMR and CD spectra together with Marfey's method. Their inhibitory activity against PC3 cell line had been tested.

Keywords: Aspergillus; Bispyrrolidinoindoline diketopiperazine; asymmetric; cytotoxicity; identification.

MeSH terms

  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology*
  • Aquatic Organisms
  • Aspergillus / chemistry*
  • Aspergillus / genetics
  • Cell Line, Tumor
  • Circular Dichroism
  • Drug Screening Assays, Antitumor
  • Fermentation
  • Humans
  • Indoles / chemistry*
  • Indoles / isolation & purification
  • Indoles / pharmacology*
  • Magnetic Resonance Spectroscopy
  • Male
  • Molecular Structure
  • Piperazines / chemistry*
  • Piperazines / isolation & purification
  • Piperazines / pharmacology*
  • Prostatic Neoplasms / drug therapy
  • Prostatic Neoplasms / pathology
  • Spectrometry, Mass, Electrospray Ionization
  • Stereoisomerism

Substances

  • Antineoplastic Agents
  • Indoles
  • Piperazines
  • WIN 64821