Isolation and structure elucidation of GM4-type gangliosides from the Okinawan starfish Protoreaster nodosus

Ke Pan; Chiaki Tanaka; Masanori Inagaki; Ryuichi Higuchi; Tomofumi Miyamoto

doi:10.3390/md10112467

Isolation and structure elucidation of GM4-type gangliosides from the Okinawan starfish Protoreaster nodosus

Ke Pan, Chiaki Tanaka, Masanori Inagaki, Ryuichi Higuchi, Tomofumi Miyamoto

Research output: Contribution to journal › Article › peer-review

12 Citations (Scopus)

Abstract

Three new ganglioside molecular species, termed PNG-1, PNG-2A, and PNG-2B were isolated from pyloric caeca of the starfish Protoreaster nodosus. Their structures were elucidated using a combination of spectroscopic and chemical methods, and characterized as 1-O-[8-O-methyl-N-acetyl-α-neuraminosyl- (2→3)-β-galactopyranosyl]-ceramide for PNG-1, 1-O-[β- galactofuranosyl-(1→3)-α-galactopyranosyl-(1→4) -8-O-methyl-N-acetyl-α-neuraminosyl-(2→3)-β-galactopyranosyl] -ceramide for PNG-2A, and 1-O-[β-galacto furanosyl-(1→3)-α- galactopyranosyl-(1→9)-N-acetyl-α-neuraminosyl-(2→3) -β-galactopyr anosyl]-ceramide for PNG-2B. PNG-2A and PNG-2B represent the first GM4 elongation products in nature.

Original language	English
Pages (from-to)	2467-2480
Number of pages	14
Journal	Marine Drugs
Volume	10
Issue number	11
DOIs	https://doi.org/10.3390/md10112467
Publication status	Published - Nov 2012

All Science Journal Classification (ASJC) codes

Drug Discovery

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title = "Isolation and structure elucidation of GM4-type gangliosides from the Okinawan starfish Protoreaster nodosus",

abstract = "Three new ganglioside molecular species, termed PNG-1, PNG-2A, and PNG-2B were isolated from pyloric caeca of the starfish Protoreaster nodosus. Their structures were elucidated using a combination of spectroscopic and chemical methods, and characterized as 1-O-[8-O-methyl-N-acetyl-α-neuraminosyl- (2→3)-β-galactopyranosyl]-ceramide for PNG-1, 1-O-[β- galactofuranosyl-(1→3)-α-galactopyranosyl-(1→4) -8-O-methyl-N-acetyl-α-neuraminosyl-(2→3)-β-galactopyranosyl] -ceramide for PNG-2A, and 1-O-[β-galacto furanosyl-(1→3)-α- galactopyranosyl-(1→9)-N-acetyl-α-neuraminosyl-(2→3) -β-galactopyr anosyl]-ceramide for PNG-2B. PNG-2A and PNG-2B represent the first GM4 elongation products in nature.",

author = "Ke Pan and Chiaki Tanaka and Masanori Inagaki and Ryuichi Higuchi and Tomofumi Miyamoto",

year = "2012",

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doi = "10.3390/md10112467",

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T1 - Isolation and structure elucidation of GM4-type gangliosides from the Okinawan starfish Protoreaster nodosus

AU - Pan, Ke

AU - Tanaka, Chiaki

AU - Inagaki, Masanori

AU - Higuchi, Ryuichi

AU - Miyamoto, Tomofumi

PY - 2012/11

Y1 - 2012/11

N2 - Three new ganglioside molecular species, termed PNG-1, PNG-2A, and PNG-2B were isolated from pyloric caeca of the starfish Protoreaster nodosus. Their structures were elucidated using a combination of spectroscopic and chemical methods, and characterized as 1-O-[8-O-methyl-N-acetyl-α-neuraminosyl- (2→3)-β-galactopyranosyl]-ceramide for PNG-1, 1-O-[β- galactofuranosyl-(1→3)-α-galactopyranosyl-(1→4) -8-O-methyl-N-acetyl-α-neuraminosyl-(2→3)-β-galactopyranosyl] -ceramide for PNG-2A, and 1-O-[β-galacto furanosyl-(1→3)-α- galactopyranosyl-(1→9)-N-acetyl-α-neuraminosyl-(2→3) -β-galactopyr anosyl]-ceramide for PNG-2B. PNG-2A and PNG-2B represent the first GM4 elongation products in nature.

AB - Three new ganglioside molecular species, termed PNG-1, PNG-2A, and PNG-2B were isolated from pyloric caeca of the starfish Protoreaster nodosus. Their structures were elucidated using a combination of spectroscopic and chemical methods, and characterized as 1-O-[8-O-methyl-N-acetyl-α-neuraminosyl- (2→3)-β-galactopyranosyl]-ceramide for PNG-1, 1-O-[β- galactofuranosyl-(1→3)-α-galactopyranosyl-(1→4) -8-O-methyl-N-acetyl-α-neuraminosyl-(2→3)-β-galactopyranosyl] -ceramide for PNG-2A, and 1-O-[β-galacto furanosyl-(1→3)-α- galactopyranosyl-(1→9)-N-acetyl-α-neuraminosyl-(2→3) -β-galactopyr anosyl]-ceramide for PNG-2B. PNG-2A and PNG-2B represent the first GM4 elongation products in nature.

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ER -

Isolation and structure elucidation of GM4-type gangliosides from the Okinawan starfish Protoreaster nodosus

Abstract

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