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

Tomofumi Miyamoto, Atsushi Yamamoto, Miho Wakabayashi, Yoshiteru Nagaregawa, Masanori Inagaki, Ryuichi Higuchi, Masahiko Iha, Kiichi Teruya

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Abstract

A new ganglioside molecular species named AG-1 has obtained from the whole body of starfish Acanthaster planci (crown of thorns). The structure of this ganglioside have been elucidated by enzymatic hydrolysis with the endo- type glycosidase. Enzymatic hydrolysis give an oligosaccharide and ceramides, quantitatively. The oligosaccharide moiety was determined mainly using 2D-NMR experiments as β-Fucf-(1→4)-α-Galp-(1→4)-α-NeuAc-(2→3),-β-Galp-(1→4)- Glcp. Meanwhile, the ceramide moiety was elucidated by NMR and GC-MS analysis as the mixture of (2S,2'S,3S,4R)-2-(2'- hydroxydocosanoyl)amino-1,3,4- trihydoxyhexadecane, and (2S,2'S,3S,4R)-2-(2'-hydroxytetracosanoyl)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.

Original languageEnglish
Pages (from-to)2295-2301
Number of pages7
JournalEuropean Journal of Organic Chemistry
Issue number12
Publication statusPublished - Jun 1 2000

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All Science Journal Classification (ASJC) codes

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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