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Biologically Active Glycosides from Asteroidea, V. Steroid Oligoglycosides from the StarfishAsterias amurensis [cf.]versicolor Sladen, 1 Structural Elucidation of a New Oligoglycoside Sulfate

✍ Scribed by Itakura, Yoichi ;Komori, Tetsuya ;Kawasaki, Toshio

Publisher
John Wiley and Sons
Year
1983
Tongue
English
Weight
767 KB
Volume
1983
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

In addition to the already known 3β,6α‐dihydroxy‐5α‐pregn‐9(11)‐en‐20‐one (1), 3β,6α,20ξ‐trihydroxy‐5α‐cholest‐9(11)‐en‐23‐one (2), 3β,6α,20ξ‐trihydroxy‐24ξ‐methyl‐5α‐cholest‐9(11)‐en‐23‐one (3) [isolated in the form of the diacetates 1′, 2′, and 3′ from the enzymatic hydrolyzate of an oligoglycoside mixture], and thornasteroside A (8) a new genuine oligoglycoside sulfate named versicoside A has been isolated and structurally elucidated by chemical and spectroscopic evidences 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‐cholest‐9(11)‐en‐23‐one (4).

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