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.
Hakomori, S. Bifunctional role of glycosphingolipids. Modulators for transmembrane signaling and mediators for cellular interactions. J. Biol. Chem. 1990, 265, 18713–18716.
[4]
Hakomori, S.; Igarashi, Y. Functional role of glycosphingolipids in cell recognition and signaling. J. Biochem. 1995, 118, 1091.
[5]
Kaneko, M.; Yamada, K.; Miyamoto, T.; Inagaki, M.; Higuchi, R. Neuritogenic activity of gangliosides from echinoderms and their structure-activity relationship. Chem. Pharm. Bull. 2007, 55, 462–463, doi:10.1248/cpb.55.462.
[6]
Higuchi, R.; Inagaki, M.; Yamada, K.; Miyamoto, T. Biologically active gangliosides from echinoderms. J. Nat. Med. 2007, 61, 367–370, doi:10.1007/s11418-007-0171-6.
[7]
Pan, K.; Inagaki, M.; Ohno, N.; Tanaka, C.; Higuchi, R.; Miyamoto, T. Identification of sixteen new galactocerebrosides from the starfish Protoreaster nodosus. Chem. Pharm. Bull. 2010, 58, 470–474, doi:10.1248/cpb.58.470.
[8]
Higuchi, R.; Mori, T.; Sugata, T.; Yamada, K.; Miyamoto, T. Synthesis of simple sea cucumber ganglioside analogs. Eur. J. Org. Chem. 1999, 1999, 3175–3178, doi:10.1002/(SICI)1099-0690(199911)1999:11<3175::AID-EJOC3175>3.0.CO;2-O.
[9]
Kuhn, R.; Wiegandt, H. Weitere Ganglioside Aus Menschenhirn. Z. Naturforsch. 1964, 19, 256.
[10]
Ledeen, R.W.; Yu, R.K.; Eng, L.F. Gangliosides of human myelin: Sialosylgalactosylceramide (G7) as a major component. J. Neurochem. 1973, 21, 829–839, doi:10.1111/j.1471-4159.1973.tb07527.x.
[11]
Yu, R.K.; Iqbal, K. Sialosylgalactosyl ceramide as a specific marker for human myelin and oligodendroglial perikarya. Gangliosides of human myelin, oligodendroglia, and neurons. J. Neurochem. 1979, 32, 293–300, doi:10.1111/j.1471-4159.1979.tb00351.x.
[12]
Ladisch, S.; Becker, H.; Ulsh, L. Immunosuppression by human gangliosides: I. Relationship of carbohydrate structure to the inhibition of T cell responses. Biochim. Biophys. Acta 1992, 1125, 180–188, doi:10.1016/0005-2760(92)90043-U.
[13]
Ladisch, S.; Hasegawa, A.; Li, R.X.; Kiso, M. Immunosuppressive activity of chemically synthesized gangliosides. Biochemistry 1995, 34, 1197–1202, doi:10.1021/bi00004a012.
[14]
Yohe, H.C.; Jacobson, R.I.; Yu, R.K. Ganglioside-Basic protein interaction: Protection of gangliosides against neuraminidase action. J. Neurosci. Res. 1983, 9, 401–412.
[15]
Narasimhan, R.; Murray, R.K. Comparative study of the glycosphingolipids of chicken bursa of Fabricius and of chicken, rat and human thymus. Biochem. J. 1978, 173, 475–482.
[16]
Saito, M.; Rosenberg, A. Sialosylgalactosylceramide (GM4) is a major ganglioside in chicken embryonic liver. J. Lipid Res. 1982, 23, 9–13.
[17]
Saito, M.; Sugiyama, K. Gangliosides in rat kidney: Composition, distribution, and developmental changes. Arch. Biochem. Biophys. 2001, 386, 11–16, doi:10.1006/abbi.2000.2206.
[18]
Li, Y.-T.; Sugiyama, E.; Ariga, T.; Nakayama, J.; Hayama, M.; Hama, Y.; Nakagawa, H.; Tai, T.; Maskos, K.; Li, S.-C. Association of GM4 ganglioside with the membrane surrounding lipid droplets in shark liver. J. Lipid Res. 2002, 43, 1019–1025, doi:10.1194/jlr.M200010-JLR200.
[19]
Chisada, S.; Horibata, Y.; Hama, Y.; Inagaki, M.; Furuya, N.; Okino, N.; Ito, M. The glycosphingolipid receptor for Vibrio trachuri in the red sea bream intestine is a GM4 ganglioside which contains 2-hydroxy fatty acids. Biochem. Biophys. Res. Commun. 2005, 333, 367–373, doi:10.1016/j.bbrc.2005.05.110.
[20]
Saito, M.; Kitamura, H.; Sugiyama, K. Liver gangliosides of various animals ranging from fish to mammalian species. Comp. Biochem. Physiol. B 2001, 129, 747–758, doi:10.1016/S1096-4959(01)00379-7.
[21]
Kelm, A.; Shaw, L.; Schauer, R.; Reuter, G. The biosynthesis of 8-O-methylated sialic acids in the starfish Asterias rubens—Isolation and characterisation of S-adenosyl-L-methionine: Sialate-8-O-methyltransferase. Eur. J. Biochem. 1998, 251, 874–884.
[22]
Schauer, R. Biosynthesis and function of N- and O-substituted sialic acid. Glycobiology 1991, 1, 449–452, doi:10.1093/glycob/1.5.449.
[23]
Schauer, R. Achievements and challenges of sialic acid research. Glycoconj. J. 2000, 17, 485–499, doi:10.1023/A:1011062223612.
[24]
Traving, C.; Schauer, R. Structure, function and metabolism of sialic acids. Cell. Mol. Life Sci. 1998, 54, 1330–1349, doi:10.1007/s000180050258.
