A novel cyclopentene derivative and a polyhydroxylated steroid from a South China Sea gorgonian Menella sp

Chem Pharm Bull (Tokyo). 2010 Oct;58(10):1391-4. doi: 10.1248/cpb.58.1391.

Abstract

A chemical investigation on a South China Sea gorgonian, Menella sp. resulted in the isolation and elucidation of menellin A (1), a highly oxygenated racemate with C(8) skeleton, and a polyhydroxylated steroid, menellsteroid C (2), along with eight known compounds (3-10). The structures of the new compounds were elucidated by means of MS, 1D and 2D NMR spectra, and the relative stereochemistry of 1 was determined by X-ray single-crystal diffraction analysis. In addition, compound 7 was isolated as a new natural product. Compounds 1-3 and 7 were selected to test the anti-inflammatory inhibition against lipopolysaccharide (LPS)-induced nitric oxide (NO) production in RAW264.7 macrophages. 1 and 3 exhibited modest inhibitory effects with IC(50) of 71.3, 33.9 µM, respectively, compared to the positive control aminoguanidine (IC(50) 25.0 µM).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anthozoa / chemistry*
  • Anti-Inflammatory Agents / chemistry*
  • Anti-Inflammatory Agents / isolation & purification
  • Anti-Inflammatory Agents / pharmacology
  • Cell Line
  • China
  • Crystallography, X-Ray
  • Cyclopentanes / chemistry*
  • Cyclopentanes / isolation & purification
  • Cyclopentanes / pharmacology
  • Lipopolysaccharides / pharmacology
  • Magnetic Resonance Spectroscopy
  • Mice
  • Molecular Conformation
  • Nitric Oxide / metabolism
  • Steroids / chemistry*
  • Steroids / isolation & purification
  • Steroids / pharmacology

Substances

  • Anti-Inflammatory Agents
  • Cyclopentanes
  • Lipopolysaccharides
  • Steroids
  • menellin A
  • menellsteroid C
  • Nitric Oxide