Glionitrin B, a cancer invasion inhibitory diketopiperazine produced by microbial coculture

J Nat Prod. 2011 Oct 28;74(10):2309-12. doi: 10.1021/np200563x. Epub 2011 Sep 28.

Abstract

A new diketopiperazine, glionitrin B (1), was produced using a microbial coculture of the fungus Aspergillus fumigatus KMC-901 and the bacterium Sphingomonas sp. KMK-001 that were isolated from acidic coal mine drainage. The structure of 1 was determined to be (3S,10aS)-dithiomethylglionitrin A. This structure was determined by the analyses of extensive NMR data and the circular dichroism spectra of the natural product and a semisynthetic compound derived from glionitrin A. In contrast to glionitrin A (2), glionitrin B (1) is not cytotoxic against the human prostate cancer cell line DU145. However, compound 1 caused suppression of DU145 cell invasion, producing 46% inhibition at 60 μM.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / isolation & purification*
  • Antineoplastic Agents / pharmacology*
  • Aspergillus fumigatus / chemistry*
  • Diketopiperazines / chemistry
  • Diketopiperazines / isolation & purification*
  • Diketopiperazines / pharmacology*
  • Drug Screening Assays, Antitumor
  • Humans
  • Male
  • Molecular Structure
  • Prostatic Neoplasms / metabolism
  • Sphingomonas / chemistry*

Substances

  • Antineoplastic Agents
  • Diketopiperazines
  • glionitrin B