Strepsesquitriol, a rearranged zizaane-type sesquiterpenoid from the deep-sea-derived actinomycete Streptomyces sp. SCSIO 10355

J Nat Prod. 2013 Dec 27;76(12):2360-3. doi: 10.1021/np400923c. Epub 2013 Dec 11.

Abstract

Strepsesquitriol, a new caged sesquiterpene, was isolated from Streptomyces sp. SCSIO 10355. Its absolute structure was established as (1R,2R,4S,5S,8S,10S)-4,9,9,10-tetramethyl-2,5,10-trihydroxytricyclo[6.2.1.0(1,5)]undecane by NMR analysis and a theoretical optical rotation derived from quantum-chemical calculations. It showed moderate inhibitory activity against lipopolysaccharide-induced TNFα production in RAW264.7 macrophages.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anti-Inflammatory Agents, Non-Steroidal / chemistry
  • Anti-Inflammatory Agents, Non-Steroidal / isolation & purification*
  • Anti-Inflammatory Agents, Non-Steroidal / pharmacology
  • Lipopolysaccharides / pharmacology
  • Mice
  • Molecular Structure
  • Nitric Oxide / biosynthesis
  • Nuclear Magnetic Resonance, Biomolecular
  • Oceans and Seas
  • Sesquiterpenes / chemistry*
  • Sesquiterpenes / isolation & purification*
  • Sesquiterpenes / pharmacology
  • Stereoisomerism
  • Streptomyces / chemistry*
  • Tumor Necrosis Factor-alpha / biosynthesis
  • Tumor Necrosis Factor-alpha / drug effects

Substances

  • Anti-Inflammatory Agents, Non-Steroidal
  • Lipopolysaccharides
  • Sesquiterpenes
  • Tumor Necrosis Factor-alpha
  • strepsesquitriol
  • Nitric Oxide