A new diketopiperazine derivative from a deep sea-derived Streptomyces sp. SCSIO 04496

Nat Prod Res. 2016;30(2):138-43. doi: 10.1080/14786419.2015.1045509. Epub 2015 Jul 21.

Abstract

A new diketopiperazine (DKP) derivative, (6R,3Z)-3-benzylidene-6-isobutyl-1-methyl piperazine-2,5-dione (1), as well as five known DKPs 2-6 was isolated from a deep sea-derived Streptomyces sp. SCSIO 04496. The structure of 1 was elucidated using a combination of 1D and 2D NMR, HR-ESI-MS and chiral-phase HPLC techniques. Compounds 1-6 did not show cytotoxic activity at a concentration of 100 μM in bioactivity assay.

Keywords: Streptomyces sp.; cyclodipeptide; diketopiperazine.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzylidene Compounds / chemistry*
  • Benzylidene Compounds / isolation & purification
  • Benzylidene Compounds / pharmacology*
  • Cell Line, Tumor / drug effects
  • Chromatography, High Pressure Liquid
  • Diketopiperazines / chemistry*
  • Diketopiperazines / pharmacology
  • Drug Screening Assays, Antitumor
  • Humans
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Oceans and Seas
  • Piperazines / chemistry*
  • Piperazines / isolation & purification
  • Piperazines / pharmacology*
  • Spectrometry, Mass, Electrospray Ionization
  • Streptomyces / chemistry*
  • Streptomyces / isolation & purification
  • Water Microbiology

Substances

  • 3-benzylidene-6-isobutyl-1-methyl piperazine-2,5-dione
  • Benzylidene Compounds
  • Diketopiperazines
  • Piperazines