Phrygiasterol, a cytotoxic cyclopropane-containing polyhydroxysteroid, and related compounds from the pacific starfish Hippasteria phrygiana

J Nat Prod. 2005 Oct;68(10):1541-4. doi: 10.1021/np049610t.

Abstract

The new cyclopropane-containing steroid phrygiasterol (1) and steroid glycoside phrygioside B (2), along with previously known borealoside C (2a) and (20R,24S)-5alpha-cholesta-3beta,6alpha,8,15alpha,24-pentaol (3), have been isolated from the Pacific starfish Hippasteria phrygiana. On the basis of spectroscopic analyses, using 1D and 2D NMR techniques and some chemical transformations, the structures of 1 and 2 have been established as (20R,24R,25R)-24,26-cyclo-5alpha-cholesta-3beta,6alpha,8,15alpha,16beta,27-hexaol (1) and the sodium salt of (20R,24S)-24-O-(3-O-methyl-4-O-sulfate-beta-d-xylopyranosyl)-5alpha-cholesta-3beta,6alpha,8,15alpha,24-pentaol (2), respectively. Compound 1 inhibited the growth of Ehrlich carcinoma cells with an IC(50) of 50 microg/mL, whereas 2 induced apoptosis of the same cells (EC(50)=70 microg/mL) and inhibited Ca(2+) influx into mouse spleenocytes (EC(50)=20microg/mL).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / isolation & purification*
  • Antineoplastic Agents / pharmacology
  • Calcium / antagonists & inhibitors
  • Drug Screening Assays, Antitumor
  • Inhibitory Concentration 50
  • Mice
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Pacific Ocean
  • Spleen / cytology
  • Spleen / drug effects
  • Starfish / chemistry*
  • Steroids / chemistry
  • Steroids / isolation & purification*
  • Steroids / pharmacology
  • Tumor Cells, Cultured

Substances

  • Antineoplastic Agents
  • Steroids
  • phrygiasterol
  • Calcium