Syn-2, 3-diols and anti-inflammatory indole derivatives from Streptomyces sp. CB09001

Nat Prod Res. 2021 Jan;35(1):144-151. doi: 10.1080/14786419.2019.1611812. Epub 2019 May 28.

Abstract

Two new natural diols, (2S, 3S, 4S)-4-methyl-1-phenylhexane-2,3-diol (1) and (2S, 3S)-4-methyl-1-phenylpentane-2,3-diol (2), together with five known compounds, xenocyloins B-D (3-5), lumichrome (6) and thymidine (7) were isolated from Streptomyces sp. CB09001. The absolute configurations of 1 and 2 were established by crystallographic structure analysis. The anti-inflammatory effects of 1-7 were also investigated in RAW246.7 murine macrophage cells stimulated by lipopolysaccharide. The indole derivative xenocyloin B (3) significantly inhibited inducible nitric oxide synthase expression in RAW264.7 cells and could be a potential anti-inflammatory drug lead.

MeSH terms

  • Animals
  • Anti-Inflammatory Agents, Non-Steroidal / chemistry*
  • Anti-Inflammatory Agents, Non-Steroidal / pharmacology*
  • Crystallography, X-Ray
  • Drug Evaluation, Preclinical
  • Flavins / chemistry
  • Flavins / pharmacology
  • Indoles / chemistry
  • Indoles / pharmacology
  • Lipopolysaccharides / pharmacology
  • Mice
  • Molecular Structure
  • Nitric Oxide Synthase Type II / antagonists & inhibitors
  • Nitric Oxide Synthase Type II / metabolism
  • RAW 264.7 Cells
  • Streptomyces / chemistry*
  • Streptomyces / metabolism

Substances

  • Anti-Inflammatory Agents, Non-Steroidal
  • Flavins
  • Indoles
  • Lipopolysaccharides
  • 7,8-dimethylalloxazine
  • Nitric Oxide Synthase Type II
  • Nos2 protein, mouse