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Biologically active glycosides from asteroidea, IV. Steroid oligoglycosides from the starfish Astropecten latespinosus Meissner
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.198319830108
Subject(s) - chemistry , solvolysis , starfish , hydrolysate , glycoside , steroid , stereochemistry , hydrolysis , organic chemistry , biochemistry , hormone , ecology , biology
Three aglycones, 3β,6α,20ξ‐trihydroxy‐5α‐cholest‐9(11)‐en‐23‐one ( 1 ), 3β,6α‐dihydroxy‐5α‐cholesta‐9(11),20(22)‐dien‐23‐one ( 2 ), and 3β,6α‐dihydroxy‐5α‐pregn‐9(11)‐en‐20‐one ( 3 ), were isolated in form of the diacetates ( 1′, 2′ , and 3′ ) from the enzymatic hydrolysate of an oligoglycoside mixture prepared from the whole bodies of Astropecten latespinosus Meissner. Two oligoglycosides were newly isolated from solvolysis products of the same glycoside mixture. The structures were elucidated by chemical and spectroscopic evidence to be 3β,6α,20ξ‐trihydroxy‐23‐oxo‐5α‐cholest‐9(11)‐en‐6α‐yl O‐β‐ D ‐fucopyranosyl‐(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)‐O‐β‐ D ‐quinovopyranoside ( 4 ) and 3β,6α,20ξ‐trihydroxy‐23‐oxo‐5α‐cholest‐9(11)‐en‐6α‐yl O‐β‐ D ‐fucopyranosyl‐(1→2)‐O‐β‐ D ‐glucopyranosyl‐(1→4)‐O‐[β‐ D ‐quinovopyranosyl‐(1→2)]‐O‐β‐ D ‐xylopyranosyl‐(1→3)‐O‐β‐ D ‐quinovopyranoside ( 5 ).