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Isolation and structural elucidation of steroid oligoglycosides from the starfish asterias rubens by means of direct online LC-NMR-MS hyphenation and one- and two-dimensional NMR investigations

: Sandvoss, M.; Pham, L.H.; Levsen, K.; Preiß, A.; Mügge, C.; Wünsch, G.


European Journal of Organic Chemistry (2000), No.7, pp.1253-1262
ISSN: 1434-193X
ISSN: 1099-0690
Journal Article
Fraunhofer ITA ( ITEM) ()
asterosaponin; asterias rubens; starfish; LC-NMR-MS hyphenation; natural product; liquid chromatography; nuclear magnetic resonance spectroscopy; mass spectrometry

LC-NMR-MS hyphenation has been applied in the screening of an asterosaponin subfraction obtained from the starfish Asterias rubens for unknown compounds. The suitability of this technique for characterizing compounds in the molecular weight range of 1200 to 1400 a.m.u. has been demonstrated. The additional information concerning the number of exchangeable protons provided by the LC-NMR-MS experiment proved to be particularly valuable for the structural elucidation. The LC-NMR-MS screening indicated the presence of hitherto unknown asterosaponins in the sample. Based on this information, four new compounds (ruberosides A-D; 2-4 and 6) have been isolated and their structures have been elucidated using one- and two-dimensional NMR techniques. A minor component has tentatively been assigned the structure 5.