Partial characterization of a biologically active steroid glycosideisolated from the starfish Marthasterias glacialis.
1. A steroid glycoside (M(2)), which induces avoidance and other reactions in the mollusc Buccinum undatum, has been isolated from extracts of the starfish Marthasterias glacialis by ion-exchange chromatography. 2. The steroid glycoside was homogeneous by t.l.c. and contained glucose, quinovose, fucose and sulphate in the molar proportions 1:2:1:1, in addition to a water-insoluble aglycone. 3. The aglycone was identified as a cholestane derivative containing an unusual Delta(24)-23-ketone system, two secondary hydroxyl groups and an olefinic double bond, and had the molecular formula C(27)H(42)O(3). 4. The rates of release of sugars and sulphate suggested that fucose was at the non-reducing end of the oligosaccharide, with glucose glycosidically linked to the steroid. The sulphate group appeared to be linked to the other hydroxyl group of the steroid.
D000818:Animals; D002852:Chromatography, Ion Exchange; D002855:Chromatography, Thin Layer; D004447:Echinodermata / Q000032:analysis*; D005643:Fucose / Q000032:analysis; D005947:Glucose / Q000032:analysis; D006027:Glycosides / Q000032:analysis*; D009682:Magnetic Resonance Spectroscopy; D013057:Spectrum Analysis; D013256:Steroids / Q000032:analysis*; D013431:Sulfates / Q000032:analysis
D006027:Glycosides; D013256:Steroids; D013431:Sulfates; D005643:Fucose; D005947:Glucose