Determination of C-23 configuration in (20R)-23-hydroxycholestane side chain of steroid compounds by 1H and 13C NMR spectroscopy

Nat Prod Commun. 2013 Sep;8(9):1219-22.

Abstract

Epimeric (20R,23R)- and (20R,23S)-23-hydroxycholestane steroids were synthesized. Their structures were elucidated by extensive 1H and 13C NMR spectroscopy and application of the Mosher's method. All proton and carbon signals of the side chains were assigned. Based on these assignments spectral data allow the determination of the C-23 stereochemistry of (20R)-23-hydroxycholestane side chains of the new natural steroids by comparison with spectra of the obtained model compounds. As a result, the C-23 configuration of two steroid compounds from the starfishes Lethasterias nanimensis chelifera and Lethasterias fusca was established.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Cholestanols / chemical synthesis*
  • Molecular Structure
  • Starfish / chemistry*
  • Stereoisomerism

Substances

  • Cholestanols