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Biologically Active Glycosides from Asteroidea, 36. Re‐examination of the Structure of Acanthaganglioside C, and the Identification of Three Minor Acanthagangliosides F, G and H
Author(s) -
Miyamoto Tomofumi,
Inagaki Masanori,
Isobe Ryuichi,
Tanaka Yoshitsugu,
Higuchi Ryuichi,
Iha Masahiko,
Teruya Kiichi
Publication year - 1997
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.199719970522
Subject(s) - chemistry , neuraminic acid , heteronuclear single quantum coherence spectroscopy , glycoside , stereochemistry , ganglioside , two dimensional nuclear magnetic resonance spectroscopy , sialic acid , biochemistry
The structure of acanthaganglioside C ( 1 ) has been re‐examined using MQ‐COSY, TOCSY, NOESY, HSQC, HMBC and HSQC‐TOCSY experiments. As a result, it is clarified that N‐acetyl neuraminic acid (NeuAc) is linked to the C‐3 position, and not the C‐4 position, of the β‐galactopyranose. In addition, three minor acanthagangliosides, F ( 2 ), G ( 3 ) and H ( 4 ), have also been isolated from the ganglioside molecular species AG‐2. Their structures have been determined on the basis of chemical and spectroscopic evidence.