Anmindenols A and B, inducible nitric oxide synthase inhibitors from a marine-derived Streptomyces sp

J Nat Prod. 2014 Jun 27;77(6):1528-31. doi: 10.1021/np500285a. Epub 2014 May 30.

Abstract

Anmindenols A (1) and B (2), inhibitors of inducible nitric oxide synthase (iNOS), were isolated from a marine-derived bacterium Streptomyces sp. Their chemical structures were elucidated by interpreting various spectroscopic data, including IR, MS, and NMR. Anmindenols A and B are sesquiterpenoids possessing an indene moiety with five- and six-membered rings derived from isoprenyl units. The absolute configuration of C-4 in anmindenol B was determined by electronic circular dichroism (ECD) of a dimolybdenum complex. Anmindenols A (1) and B (2) inhibited nitric oxide production in stimulated RAW 264.7 macrophage cells with IC50 values of 23 and 19 μM, respectively.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Indenes / chemistry
  • Indenes / isolation & purification*
  • Indenes / pharmacology*
  • Inhibitory Concentration 50
  • Lipopolysaccharides / pharmacology
  • Macrophages / drug effects
  • Marine Biology
  • Mice
  • Molecular Structure
  • NF-kappa B / metabolism
  • Nitric Oxide / biosynthesis
  • Nitric Oxide Synthase Type II / antagonists & inhibitors*
  • Nuclear Magnetic Resonance, Biomolecular
  • Sesquiterpenes / chemistry
  • Sesquiterpenes / isolation & purification*
  • Sesquiterpenes / pharmacology*
  • Streptomyces / chemistry*

Substances

  • Indenes
  • Lipopolysaccharides
  • NF-kappa B
  • Sesquiterpenes
  • anmindenol A
  • anmindenol B
  • Nitric Oxide
  • Nitric Oxide Synthase Type II