Steroidal triglycosides, kurilensosides A, B, and C, and other polar steroids from the Far Eastern starfish Hippasteria kurilensis

J Nat Prod. 2008 May;71(5):793-8. doi: 10.1021/np070637x. Epub 2008 Mar 22.

Abstract

Three novel steroidal triglycosides, designated as kurilensosides A, B, and C (1- 3), were isolated along with a new steroidal diglycoside, kurilensoside D (4), and two new (6, 7) and one known (5) polyhydroxysteroid from the alcoholic extract of the Far Eastern starfish Hippasteria kurilensis. Compounds 1-3 are the first triglycosides containing two carbohydrate chains found from starfish. The structures of 1-7 were elucidated by spectroscopic methods (mainly 2D NMR) and chemical derivatization. Glycosides 1-4 and steroids 6 and 7 inhibited sea urchin egg fertilization by sperm preincubated with these compounds.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Fertilization / drug effects
  • Glycosides / chemistry
  • Glycosides / isolation & purification*
  • Glycosides / pharmacology
  • Male
  • Molecular Structure
  • Ovum / drug effects
  • Russia
  • Spermatozoa / drug effects
  • Starfish / chemistry*
  • Steroids / chemistry
  • Steroids / isolation & purification*
  • Steroids / pharmacology

Substances

  • Glycosides
  • Steroids
  • kurilensoside A
  • kurilensoside B
  • kurilensoside C