Stereoselective synthesis of (26R)-26-hydroxydiosgenin and its effect on the regulation of rat ovarian function

Bioorg Chem. 2021 Oct:115:105189. doi: 10.1016/j.bioorg.2021.105189. Epub 2021 Jul 21.

Abstract

The stereoselective cyclization of a C-16 acetylated 22,26-dioxocholestene derivative to give the spirostane E and F rings, under alkaline conditions, yields exclusively the (26R)-26-hydroxydiosgenin. Both experimental and computational data support the formation of a single diastereoisomer. The effect of diosgenin and (26R)-26-hydroxydiosgenin on rat ovary is also investigated.

Keywords: (26R)-26-hydroxydiosgenin; Diosgenin; Rat ovary; Stereo-differentiated attack.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Cyclization
  • Diosgenin / analogs & derivatives*
  • Diosgenin / chemical synthesis
  • Diosgenin / pharmacology*
  • Female
  • Models, Molecular
  • Ovary / drug effects*
  • Ovary / physiology
  • Rats
  • Stereoisomerism

Substances

  • Diosgenin