Prodigiosin R2, a new prodigiosin from the roseophilin producer Streptomyces griseoviridis 2464-S5

J Antibiot (Tokyo). 2018 Mar;71(3):393-396. doi: 10.1038/s41429-017-0011-1. Epub 2018 Jan 18.

Abstract

Roseophilin (2) is a unique prodigiosin-related compound produced by Streptomyces griseoviridis 2464-S5, and is characterized by a central furan ring and a bicyclic alkyl chain. During a search for biosynthetic intermediates of 2, a new metabolite designated prodigiosin R2 (1) was isolated from the culture of the roseophilin producer. The molecular formula of 1 was established as C27H35N3O by high-resolution FAB-MS. The structure of 1 was determined by NMR spectroscopic analyses as a prodigiosin derivative with the same bicyclic alkyl chain as 2. Prodigiosin R2 (1) showed potent cytotoxicity against HeLa human cervical carcinoma cells and HT1080 human fibrosarcoma cells with IC50s of 0.41 and 0.82 μM, respectively.

MeSH terms

  • Antibiotics, Antineoplastic / biosynthesis
  • Antibiotics, Antineoplastic / isolation & purification*
  • Antibiotics, Antineoplastic / pharmacology*
  • Cell Line, Tumor
  • HeLa Cells
  • Humans
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Prodigiosin / biosynthesis
  • Prodigiosin / isolation & purification*
  • Prodigiosin / pharmacology*
  • Spectrophotometry, Ultraviolet
  • Streptomyces / chemistry
  • Streptomyces / metabolism*

Substances

  • Antibiotics, Antineoplastic
  • prodigiosin r2
  • Prodigiosin