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Biologically Active Glycosides from Asteroidea, IX. Steroid Oligoglycosides from the Starfish Asterias amurensis [cf.] versicolor Sladen, 2. Structure Elucidation of Two New Oligoglycoside Sulfates, Versicoside B and Versicoside C
Author(s) -
Itakura Yoichi,
Komori Tetsuya
Publication year - 1986
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.198619860215
Subject(s) - starfish , chemistry , asterias , stereochemistry , glycoside , sulfation , biochemistry , ecology , biology
In addition to the already known asteronylpentaglycoside sulfate ( 5 ) and ovarian asterosaponin 1 ( 6 ), two new genuine asterosaponins named versicoside B ( 3 ) and C ( 4 ) have been isolated from the starfish Asterias amurensis [cf.] versicolor Sladen and characterized. Their structures have been elucidated as the monosodium salt of 6α‐[( O ‐β‐D‐galactopyranosyl‐(1→3)‐ O ‐β‐D‐fucopyranosyl‐(1→2)‐ O ‐β‐D‐galactopyranosyl‐(1→4)‐ O ‐[β‐D‐quinovopyranosyl‐(1→2)]‐ O ‐β‐D‐xylopyranosyl‐(1→3)‐β‐D‐quinovopyranosyl)oxy]‐20ξ‐hydroxy‐3β‐(sulfooxy)‐5α,24ξ‐ergost‐9(11)‐en‐23‐one ( 3 ) and the monosodium salt of 6α‐[( O ‐β‐D‐fucopyranosyl‐(1→2)‐ O ‐β‐D‐galactopyranosyl‐(1→4)‐ O ‐[β‐D‐quinovopyranosyl‐(1→2)]‐ O ‐β‐D‐xylopyranosyl‐(1→3)‐β‐D‐quinovopyranosyl)oxy]‐20→‐hydroxy‐3β‐(sulfooxy)‐5α,24ξ‐ergost‐9(11)‐en‐23‐one ( 4 ). Apart from the conventional analytical methods, negative fast‐atom bombardment (negative FAB) mass spectrometry was successfully used for the first time for determination and confirmation of the structure of the natural oligoglycoside sulfates.