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

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 ).