Isolation and Structure Elucidation of GM4-Type Gangliosides from the Okinawan Starfish Protoreaster nodosus

doi:10.3390/md10112467

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Mar. Drugs 2012, 10(11), 2467-2480; doi:10.3390/md10112467

Article

Isolation and Structure Elucidation of GM4-Type Gangliosides from the Okinawan Starfish Protoreaster nodosus

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

Graduate School of Pharmaceutical Sciences, Kyushu University, Maidashi 3-1-1, Higashi-ku, Fukuoka 812-8582, Japan

* Author to whom correspondence should be addressed.

Received: 8 October 2012; in revised form: 26 October 2012 / Accepted: 30 October 2012 / Published: 5 November 2012

(This article belongs to the Special Issue Marine Glycoconjugates)

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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.

Keywords: glycosphingolipid; ganglioside; GM4; starfish; Protoreaster nodosus

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Cite This Article

MDPI and ACS Style

Pan, K.; Tanaka, C.; Inagaki, M.; Higuchi, R.; Miyamoto, T. Isolation and Structure Elucidation of GM4-Type Gangliosides from the Okinawan Starfish Protoreaster nodosus. Mar. Drugs 2012, 10, 2467-2480.

AMA Style

Pan K, Tanaka C, Inagaki M, Higuchi R, Miyamoto T. Isolation and Structure Elucidation of GM4-Type Gangliosides from the Okinawan Starfish Protoreaster nodosus. Marine Drugs. 2012; 10(11):2467-2480.

Chicago/Turabian Style

Pan, Ke; Tanaka, Chiaki; Inagaki, Masanori; Higuchi, Ryuichi; Miyamoto, Tomofumi. 2012. "Isolation and Structure Elucidation of GM4-Type Gangliosides from the Okinawan Starfish Protoreaster nodosus." Mar. Drugs 10, no. 11: 2467-2480.

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