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Biologically Active Glycosides from Asteroidea, V. Steroid Oligoglycosides from the Starfish Asterias amurensis [cf.] versicolor Sladen, 1 Structural Elucidation of a New Oligoglycoside Sulfate
Author(s) -
Itakura Yoichi,
Komori Tetsuya,
Kawasaki Toshio
Publication year - 1983
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.198319831205
Subject(s) - chemistry , glycoside , stereochemistry , steroid , sulfate , organic chemistry , biochemistry , hormone
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 ).