Efficient conversion of tomatidine into neuritogenic pregnane derivative

Chem Pharm Bull (Tokyo). 2007 Jul;55(7):1077-8. doi: 10.1248/cpb.55.1077.

Abstract

Moderate acetylation of tomatidine with anhydrous acetic acid and pyridine for 20 h at r.t., followed by pseudomerization in ice-water, gave a delta(20(22))-pseudo compound, which was then subjected to ozonolysis to provide a pregnane derivative in a total 54% yield showing neuritogenic and NGF-enhancing activities.

MeSH terms

  • Acetic Acid / chemistry
  • Acetylation
  • Animals
  • Cell Line
  • Molecular Structure
  • Nerve Growth Factors / chemical synthesis
  • Nerve Growth Factors / chemistry
  • Nerve Growth Factors / pharmacology
  • Neurites / drug effects*
  • PC12 Cells
  • Plant Components, Aerial / chemistry
  • Pregnanes / chemical synthesis*
  • Pregnanes / chemistry*
  • Pregnanes / pharmacology
  • Pyridines / chemistry
  • Rats
  • Solanum lycopersicum / chemistry*
  • Tomatine / analogs & derivatives*
  • Tomatine / chemistry

Substances

  • Nerve Growth Factors
  • Pregnanes
  • Pyridines
  • tomatidine
  • Tomatine
  • pyridine
  • Acetic Acid