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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glucosides
Gangliosides
Glycosides
hydrolysis
Enzymatic hydrolysis
Ceramides
Oligosaccharides
nuclear magnetic resonance
FORTRAN
Nuclear magnetic resonance
Glycoside Hydrolases
Experiments

All Science Journal Classification (ASJC) codes

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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Biologically active glycosides from asteroidea, 40 two new gangliosides, acanthagangliosides I and J from the starfish Acanthaster planci. / Miyamoto, Tomofumi; Yamamoto, Atsushi; Wakabayashi, Miho; Nagaregawa, Yoshiteru; Inagaki, Masanori; Higuchi, Ryuichi; Iha, Masahiko; Teruya, Kiichi.

In: European Journal of Organic Chemistry, No. 12, 01.06.2000, p. 2295-2301.

Research output: Contribution to journalArticle

Miyamoto, Tomofumi ; Yamamoto, Atsushi ; Wakabayashi, Miho ; Nagaregawa, Yoshiteru ; Inagaki, Masanori ; Higuchi, Ryuichi ; Iha, Masahiko ; Teruya, Kiichi. / Biologically active glycosides from asteroidea, 40 two new gangliosides, acanthagangliosides I and J from the starfish Acanthaster planci. In: European Journal of Organic Chemistry. 2000 ; No. 12. pp. 2295-2301.
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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.",
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