Cytotoxic cholesta-1,4-dien-3-one derivatives from soft coral Nephthea sp

Steroids. 2013 Apr;78(4):396-400. doi: 10.1016/j.steroids.2012.12.012. Epub 2013 Jan 24.

Abstract

Five new steroids, (12β, 22R)-12-acetoxy-22-hydroxy-cholesta-1,4-dien-3-one (1), (12β, 22R)-12-hydroxy-22-acetoxy-cholesta-1, 4-dien-3-one (2), (12β, 22R)-12, 22-diacetoxy-cholesta-1, 4-dien-3-one (3), (22R)-18, 22-diacetoxy-cholesta-1, 4-dien-3-one (4), (20R, 22R)-20-hydroxy-22-acetoxy-cholesta-1, 4-dien-3-one (5), and one known steroid astrogorgol N (6), were isolated from soft coral Nephthea sp. Their structures were established by spectroscopic analysis (1D, 2D NMR, HRMS) and comparisons of their spectral data with those of related steroids. The absolute configuration at C-22 of 1 was determined to be R by Mosher's analysis. All isolated compounds exhibited cytotoxic activity against HeLa cells with IC50 values ranged from 7.51±0.22 to 18.72±0.78μg/mL.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anthozoa / chemistry*
  • Cell Death / drug effects
  • Cell Proliferation / drug effects
  • Cholestenones / chemistry
  • Cholestenones / isolation & purification
  • Cholestenones / pharmacology*
  • Cholestenones / toxicity*
  • Dose-Response Relationship, Drug
  • HeLa Cells
  • Humans
  • Molecular Conformation
  • Structure-Activity Relationship

Substances

  • Cholestenones
  • cholesta-1,4-dien-3-one