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Biologically active glycosides from asteroidea, III. Steroid oligoglycosides from the starfishAcanthaster planci L., 2. Structures of two newly characterized genuine sapogenins and an oligoglycoside sulfate

✍ Scribed by Komori, Tetsuya ;Nanri, Hiroyuki ;Itakura, Yoichi ;Sakamoto, Kenji ;Taguchi, Shuzo ;Higuchi, Ryuichi ;Kawasaki, Toshio ;Higuchi, Tetsuo

Publisher
John Wiley and Sons
Year
1983
Tongue
English
Weight
1005 KB
Volume
1983
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

From the whole bodies of Acanthaster planci L. a genuine oligoglycoside which is an unstable type 20‐hydroxycholesten‐23‐one glycoside sulfate has been isolated in large quantities. Apart from the known 3β,6α‐dihydroxy‐5α‐pregn‐9(11)‐en‐20‐one (1) two new genuine aglycones were isolated by enzymatic hydrolysis of the crude oligoglycoside fraction for the first time. The structures were identified by chemical and spectroscopic evidence to be 3β,6α,20ζ‐trihydroxy‐5α‐cholest‐9(11)en‐23‐one (2) and 3β,6α,20ξ‐trihydroxy‐5α‐cholesta‐9(11),24‐dien‐23‐one (3), respectively. The structure of the newly characterized pentaglycoside sulfate Acanthaglycoside A was then determined to be 3β‐sodiosulfonatooxy‐6α,20ξ‐dihydroxy‐23‐oxo‐5α‐cholesta‐9(11),24‐dien‐6α‐ylO‐β‐D‐fucopyranosyl‐(1→2)‐O‐β‐D‐quinovopyranosyl‐(1→4)‐O‐[β‐D‐quinovopyranosyl‐(1→2)]‐O‐β‐D‐xylopyranosyl‐(1→3)‐O‐β‐D‐quinovopyranoside (4). Apart from conventional analytical methods, fast atom bombardment mass spectrometry (FAB‐MS) was successfully used for the first time for determination and confirmation of the structure of the natural oligoglycoside sulfate.

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