Biologically active glycosides from asteroidea, 40 - Two new gangliosides,acanthagangliosides I and J from the starfish Acanthaster planci

Citation
T. Miyamoto et al., Biologically active glycosides from asteroidea, 40 - Two new gangliosides,acanthagangliosides I and J from the starfish Acanthaster planci, EUR J ORG C, (12), 2000, pp. 2295-2301
Citations number
8
Language
INGLESE
art.tipo
Article
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
1434-193X → ACNP
Issue
12
Year of publication
2000
Pages
2295 - 2301
Database
ISI
SICI code
1434-193X(200006):12<2295:BAGFA4>2.0.ZU;2-C
Abstract
A new ganglioside molecular species named AC-1 has obtained from the whole body of starfish Acanthaster planci (crown of thorns). The structure of thi s ganglioside have been elucidated by enzymatic hydrolysis with the endo-ty pe glycosidase. Enzymatic hydrolysis gave an oligosaccharide and ceramides, quantitatively. The oligosaccharide moiety was determined mainly using 2D- NMR experiments as beta-Fucf(1-->4)-alpha-Galp-(1-->4)-alpha-NeuAc-(2-->3)- beta-Galp-(1-->4)-Glcp. Meanwhile, the ceramide moiety was elucidated by NM R and CC-MS analysis as the mixture of (2S,2'S,3S,4R)-2-(2' -hydroxydocosan oyl) amino-1,3,4-trihydoxyhexadecane, and (2S,2'S,3S,4R)-2-(2'-hydroxytetra cosanoyl)amino-1,3,4-trihydoxyhexadecane. Reversed-phase HPLC of AG-1 gave two kinds of gangliosides named acanthagangliosides I (1) and J (2). Their structures have been identified by negative FAB-MS.