Abstract
Marine glycolipids, as well as those from terrestrial organisms, are amphiphylic compounds which are currently divided into two main groups: glycoglycerolipids (GGLs) and glycosphingolipids (GSLs). There is a third important group comprising glycolipids whose lipid portion is derived from mevalonate, i.e. steroidal and terpenic glycosides. The occurrence of polyisoprenoidic glycolipids is generally confined to species of a few taxa, where they frequently perform peculiar biological functions; as to their occurrence in marine organisms, they are mostly present in invertebrates belonging to phylum Echinoderma.
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References
Minale, L., R. Riccio, and F Zollo: Steroidal Oligoglycosides and Polyhydroxysteroids from Echinoderms. In: Progress in the Chemistry of Organic Natural Products (W. Herz, G.W. Kirby, R.E. Moore W. Steglich, and Ch. Tamm, eds. Vol. 62, p. 75. Wien, New York: Springer. 1993.
Gunstone, F.D., J.L. Harwood, and F.D.Padley: The Lipid Handbook, p. 12. London: Chapman & Hall. 1994.
Sweeley, C.C.: Sphingolipids. In: New Comprehensive Biochemistry D.E. Vance and J. Vance, eds. Vol. 20, Biochemistry of Lipids, Lipoproteins and Membranes, p. 327. Amsterdam: Elsevier. 1991.
Rajagopal, M.V., and K. Sohonie: Studies on the Sea Anemone Gyrostomasp. Biochem. J., 65, 34 (1957).
Nagai, Y., and Y. Isono: Occurrence of Animal Sulfolipid in the Gametes of Sea Urchins. Jpn. J. Exp. Med., 35, 315 (1965).
Isono, Y, and Y. Nagal: Biochemistry of Glycolipids of Sea Urchin Gametes. 1. Separation and Characterization of New Type of Sulfolipid and Sialoglycolipid. Jpn. J. Exp. Med., 36, 461 (1966).
Isono, Y: Changes of Glycolipids during Early Development of Sea Urchin Embryos. Jpn. J. Exp. Med., 37, 87 (1967).
Nichols, B.W., and B.J.B. Woods: New Glycolipid Specific to Nitrogen-Fixing Blue-Green Algae. Nature, 217, 767 (1968).
Walsby, A.E., and B.W. Nichols: Lipid Composition of Heterocysts. Nature, 221,673 (1969).
Vaskovsky, V.E., E.Y Kostetsky, V.I. Svetaskev, I.G. Zhukova, and G.P. Smirnova: Glycolipids in Marine Invertebrates. Comp. Biochem. Physiol., 34, 163 (1970).
Koezuka, I., M. Kloppenburg, and H. Wiegandt: Characterization of Gangliosides from Fish Brain. Biochim. Biophys. Acta, 210, 299 (1970).
Komai, Y, S. Mitsukawa, and M. Satake: Glycolipids in Nervous Tissue of Invertebrates. J. Biochem., 70, 367 (1971).
Hayashi, A., and F. Matsuura: Isolation of a New Sphingophosphonolipid Containing Galactose from the Viscera of Turbo cornutus. Biochim. Biophys. Acta, 248, 133 (1971).
Bryce, T.A., D. Welti, A.E. Walsby, and W.B. Nichols: Monohexoside Derivatives of Long-Chain Polyhydroxy Alcohols: a Novel Class of Glycolipid Specific to Heterocystous Algae. Phytochemistry, 11, 295 (1972).
BJöRkman, L.R., K.A. Karlsson, and K. Nilsson: Existence of Cerebroside and Cholesterol Sulfate in the Tissues of the Sea Star Asterias rubens. Comp. Biochem. Physiol., 43B, 409 (1972).
BJöRkman, L.R., K.A. Karlsson, I. Pascher, and B.E. Samuelsson: Isolation of Large Amounts of Cerebroside and Cholesterol Sulphate in the Sea Star Asterias rubens. Biochim. Biophys. Acta, 270, 260 (1972).
Matsubara, T., and A. Hayashi: The Existence of Branched Structure in the Sugar Moiety of Oyster Sphingoglycolipid. J. Biochem., 74, 853 (1973).
Kochetkov, N.K., I.G. Zhukova, G.P. Smirnova, and I.S. Glukhoded: Isolation and Characterization of a Sialoglycolipid from the Sea Urchin Strongylocentrotus intermedius. Biochim. Biophys. Acta, 326, 74 (1973).
KOMAI, Y, S. Matsukawa, and M. Satake: Lipid Composition of the Nervous Tissue of the Invertebrates Aplysia kurodai(Gastropod) and Cambarus clarki(Arthropod). Biochim. Biophys. Acta, 316, 271 (1973).
Kreps, E.M., N.F. Avrova, M.A. Chebotarë Va, E.V. Chirkovskaya, V.I. Krasilnikova, E.E. Kruglova, M.V. Levitina, E.L. Obukhova, L.F. Pomazanskaya, N.I. Pravdina, and S.A. Zabelinskii: Phospholipid and Glycolipids in the Brain of Marine Fish. Comp. Biochem. Fhysiol., 52B, 283 (1975).
Sugita, M., and T. Hori: New Types of Gangliosides with Sialic Acid Residues in the Inner Part of Their Carbohydrate Chains. J. Biochem., 80, 637 (1976).
Matsubara, T., and A. Hayashi: Structural Studies on Glycolipid of Shellfish. II. Occurrence of 3-O-methylgalactosamine in Oyster Glycolipid. J. Biochem., 83, 1195 (1978).
Lambein, F., and C.P. Wolk: Structural studies on the Glycolipid from the Envelope of the Heterocyst of Anabaene cylindrica. Biochemistry, 12, 791 (1973).
Kochetkov, N.K., and G.P. Smirnova: Glycolipids of Marine Invertebrates. Adv. Carbohydr. Chem. Biochem., 44, 387 (1986).
Hori, T., and M. Sugita: Sphingolipids in Lower Animals. Prog. Lipid Res., 32, 25 (1993).
Kates, M.: Glycolipids of Higher Plants, Algae, Yeasts, and Fungi. In: Handbook of Lipid Research M. Kates, ed.) Vol. 6, p. 235. New York, London: Plenum Press. 1990.
Higuchi, R., T. Natori, and T. Komori: Glycosphingolipids from the Starfish Asterina pectinifera. Isolation and Characterization of Acanthacerebroside B and Structure Elucidation of Related, Nearly Homogeneous Cerebrosides. Liebigs Ann. Chem., 51 (1990).
Higuchi, R., M. Inagaki, K. Togawa, T. Miyamoto, and T. Komori: Constituents of Holothuriodeae. IV CE-2b, CE-2c and CE-2d, Three New Sphingosine-type Glucocerebrosides from the Sea Cucumber Cucumaria echinata. Liebigs Ann. Chem., 79 (1994).
Folch, J., M. Lees, and G.H.Sloane-Stanley: A Simple Method for the Isolation and Purification of Total Lipids from Animals Tissues. J. Biol. Chem., 226, 497 (1957).
Higuchi, R., S. Matsumoto, M. Fujita, T. Komori, and T. Sasaki: Glycosphingolipids from the Starfish Astropecten latespinosus, 2.Structure of Two New Ganglioside Molecular Species and Biological Activity of the Ganglioside. Liebigs Ann. Chem., 545 (1995).
Oshima, Y, S.-H. Yamada, K. Matsunaga, T. Moriya, and Y. Ohizumi: A Monogalactosyl Diacylglycerol from a Cultured Marine Dinoflagellate, Scrippsiella tro-choidea. J. Nat. Prod., 57, 534 (1994).
Jin, W., K.L. Rinehart, and E.A. Jares-Erijman: Ophidiacerebrosides A-E, Five New Cytotoxic Glycosphingolipids from the Sea Star Ophidiaster ophidiamus. J. Org. Chem., 59, 144 (1994).
Kobayashi, J., Y Doi, and M. Ishibashi: Shimofuridin A, a Cytotoxic and Antimicrobial Nucleoside Derivative with an Acylfucopyranoside Unit from the Marine Tunicate Aplidium multiplicatum. J. Org. Chem., 59, 255 (1994).
Higuchi, R., K. Inukai, J.X. Jhou, M. Honda, T. Komori, S. Tsuji, and Y Nagai: GAA-6 and GAA-7, Two Ganglioside Molecular Species from the Starfish Asterias amurensis versicolor, Liebigs Ann. Chem., 359 (1993).
Natori, T., M. Morita, K. Akimoto, and Y. Koezuka: Agelasphin, Novel Antitumor and Immunostimulatory Cerebrosides from the Marine Sponge Agelas mauritiana. Tetrahedron, 50, 2771 (1994).
Higuchi, R., M. Inagaki, K. Togawa, T. Miyamoto, and T. Komori: Constituents of Holothuriodeae. V. Isolation and Structure of Cerebrosides from the Sea Cucumber Pentacta australis. Liebigs Ann. Chem., 653 (1994).
Sata, N., N. Asai, S. Matsunaga, and N. Fusetani: Erylusamines, Interleukin-6 Receptor Antagonists, from the Marine Sponge Erylus placenta. Tetrahedron, 50, 1093 (1994).
Kubo, H., A. Irie, F. Inagaki, and M. Hoshi: Gangliosides from the Eggs of the Sea Urchin Anthocidaris crassispina. J. Biochem., 108, 185 (1990).
Itonori, S., K. Kamemura, K. Narushima, N. Sonku, O. Itasaka, T. Hori, and M. Sugita: Characterization of a New Phosphonocerebroside, N-Methyl-2-aminoethyl-phosphonylglucosylceramide, from the Antarctic Krill Euphausia superba. Biochim. Biophys. Acta, 1081, 321 (1991).
Costantino, V., E. Fattorusso, A. Mangoni, M. DI Rosa, A. Ianaro, and P. Maffia: Glycolipids from Sponges. IV. Immunomodulating Glycosyl Ceramides from the Marine Sponge Agelas dispar. Tetrahedron, 52, 1573 (1996).
Sweeley, C.C., and R.V.P. Tao: Gas Chromatographie Estimation of Carbohydrates in Glycosphingolipids. Methods Carbohydr. Chem., 6, 8 (1972).
Svennerholm, L.: Quantitative Estimation of Sialic Acid. III. An Anion-Exchange-Resin Method. Acta Chem. Scand., 12, 547 (1958).
Hakomori, S.: Rapid Permethylation of Glycolipids and Polysaccharides, Catalyzed by Methylsulfinyl Carbanion in Dimethyl Sulfoxide. J. Biochem., 55, 205 (1964).
Sanford, P.A., and H.E. Conrad: The Structure of the Aerobacter aerogenesA3(S1) Polysaccharide. I. A Reexamination using Improved Procedures for Methylation Analysis. Biochemistry, 5, 1508 (1966).
Li, Y.-T., and S.-C. Li: Glycosidases in Jack Bean Meal. I. Separation of Various Glycosidases by Isoelectric Focusing. J. Biol. Chem., 243, 3994 (1968).
Li, S.-C., and Y.-T. Li: Glycosidases of Jack Bean Meal. II. Crystallization and Properties of β-N-Acetylhexosaminidase. J. Biol. Chem., 245, 5153 (1970).
Weissman, B., and D.F. Hinrichsen: Mammalian α-Acetylagalactosaminase. Occurrence, Partial Purification, and Action on Linkages in Submaxillary Mucins. Biochemistry, 8, 2034 (1969).
Gatt, S., and M.M. Rapport: Isolation of β-Galactosidase and β-Glucosidase from Brain. Biochim. Biophys. Acta, 113, 567 (1966).
Kubo, H., G.J. Jiang, A. Irie, M. Morita, T. Matsubara, and M. Hoshi: A Novel Ceramide Trihexoside from the Eggs of the Sea Urchin Hemicentrotus pulcherrimus. J. Biochem., 111, 726 (1992).
KAWANO, Y, R. Higuchi, and T. Komori: Glycosphingolipids from the Starfish Acanthaster planci,4. Isolation and Structure of Five New Gangliosides. Liebigs Ann. Chem., 43 (1990).
Muralikrishna, G., G. Reuter, J. PETER-Katalinic, H. Egge, F.G. Hanish, H.C. Siebert, and R. Shauer: Identification of a New Ganglioside from the Starfish Asterias rubens. Carbohydr. Res., 236, 321 (1992).
Hoffman, J., B. Lindberg, and S. Svensson: Determination of Anomeric Configuration of Sugar Residues in Acetylated Oligo-and Polysaccharides by Oxidation with Chromium Trioxide. Acta Chem. Scand., 26, 661 (1972).
Laine, R.A., and O. Renkonen: Ceramide Di-and Trihexosides of Wheat Flour. Biochemistry, 13, 2837 (1974).
Laine, R.A., and O. Renkonen: Analysis of Anomeric Configurations in Glyceroglycolipids and Glycosphingolipids by Chromium Trioxide Oxidation. J. Lipid Res., 16, 102 (1975).
Inagaki, F., S. Tate, H. Kubo, and M. Hoshi: A Novel Difucosylated Neutral Glycosphingolipid from the Eggs of the Sea Urchin Hemicentrotus pulcherrimus. II. Structural Determination by Two-Dimensional NMR. J. Biochem., 112, 286 (1992).
Costantino, V., E. Fattorusso, and A.Mangoni: Glycolipids from Sponges. III. Glycosyl Ceramide Composition of the Marine Sponge Agelas conifera. Liebigs Ann. Chem., 2133 (1995).
Costantino, V., E. Fattorusso, A. Mangoni, M. Aknin, A. Fall, A. Samb, and J. Miralles: An Unusual Ether Glycolipid from the Senegalese Sponge Trikentrion loeveCarter. Tetrahedron, 49, 2711 (1993).
Costantino, V., E. Fattorusso, and A.Mangoni: Isolation of Five-Membered Cyclitol Glycolipids, Crasserides: Unique Glycerides from the Sponge Pseudoceratina crassa. J. Org Chem., 58, 186 (1993).
Costantino, V., E. Fattorusso, A. Mangoni, M. Aknin, and E.M. Gaydou: Axycer-amide A and B, Two Novel Tri-α-glycosylceramides from the Marine Sponge Axinellasp. Liebigs Ann. Chem., 181 (1994).
Cafieri, F., E. Fattorusso, Y. Mahajnah, and A.Mangoni: Longiside, a Novel Digalactosylceramide from the Caribbean Sponge Agelas longissima. Liebigs Ann. Chem., 1187 (1994).
Kobayashi, J., C. Zeng, and M. Ishibashi: Keruffaride, a New All-cis-Cyclopentane-pentol-containing Metabolite from the Okinawan Marine Sponge Luffariellasp. J. Chem. Soc. Chem. Comm., 79 (1993).
Ishibashi, M., C.-M. Zeng, and J. Kobayashi: Keruffaride: Structure Revision and Isolation from Plural Genera of Okinawan Marine Sponges. J. Nat. Prod., 56, 1856 (1993).
VAN Hummel, H.C.: Chemistry and Biosynthesis of Plant Galactolipids. Fortschr. Chem. Org. Naturst., 32, 267 (1975).
Dembitsky, V. M., O.A. Rozentsvet, E.E. and Pechenkina: Glycolipids, Phospholipids and Fatty Acids of Brown Algae Species. Phytochemistry, 29, 3417 (1990).
Jones, A.L., and J.L. Harwood: Comparative Aspects of Lipid Metabolisms in Marine Algae. Biochem. Soc. Trans., 15, 482 (1987).
Dembitsky, V.M., E.E. Pechenkina, and O.A. Rozentsvet: Glycolipids and Fatty Acids of Some Seaweeds and Marine Grasses from the Black Sea. Phytochemistry, 30,2279 (1991).
Dembitsky, V.M., T. Rezanka, and O.A. Rozentsvet: Lipid Composition of Three Macrophytes from the Caspian Sea. Phytochemistry, 33, 1015 (1993).
Kitagawa, I., K. Hayashi, and J. Kobayashi: Heterosigma-glycolipids I and II, New Galactolipids from a Raphidophycean Dinoflagellate Heterosigmasp. Chem. Pharm. Bull., 37, 849 (1989).
Kobayashi, M., K. Hayashi, K. Kawazoe, and I. Kitagawa: Heterosigma Glycolipids I-IV, Four New Diacylglycerolipids from the Marine Dinoflagellate Heterosigma akashiwo. Chem. Pharm. Bull., 40, 1404 (1992).
Kikuchi, H., Y. Ksukitani, T. Manda, T. Fujii, H. Nakanishi, M. Kobayashi, and I. Kitagawa: Marine Natural Products. X. Pharmacologically Active Glycolipid from the Okinawan Marine Sponge Phyllospongiafoliascens(Pallas). Chem. Pharm. Bull., 30, 3544 (1982).
Jiang, Z.D., and W.H. Gerwick: Galactolipid from the Temperate Red Marine Alga Gracilariopsis lemaneiformis. Phytochemistry, 29, 1433 (1990).
Arao, T., and M. Yamada: Positional Distribution of Fatty Acids in Galactolipids of Algae. Phytochemistry, 28, 805 (1989).
Murakami, N., H. Shirahshi, J. Sakakibara, and Y. Tsuchida: A Novel Glicerogly-colipid from the Nitrogen-fixing Cyanobacterium Anabaena flos-aquaeF. flosaquae. Chem. Pharm. Bull., 40, 285 (1992).
Jiang, Z.D., and W.H. Gerwick: An Aldehyde-Containing Galactolipid from the Red Alga Gracilariopsis lemaneiformis. Lipids, 26, 960 (1991).
Fusetani, N., and Y. Hashimoto: Structures of Two Water Soluble Hemolysins Isolated from the Green Alga Ulva pertusa. Agric. Biol. Chem., 39, 2021 (1975).
Son, B.W.: Glycolipids from Gracilaria verrucosa. Phytochemistry, 29, 307 (1990).
Son, B.W.: Glycolipid from the Korean Marine Red Alga Gracilaria verrucosa. Bull. Korean Chem. Soc, 9, 264 (1988).
Katsuoka, M., C. Ogura, H. Etoh, K. Sakata, and K. Ina: Galactosyl-and Sulfoquinovosyldiacylglicerols Isolated from the Brown Algae, Undaria pinnatifidaand Costaria costataas repellents of the blue mussel Mytilus edulis. Agric. Biol. Chem., 54, 3043 (1990).
Pettit, G.R., A.L. Jones, and L.H.Harwood: Lipids of the Marine Red Algae, Chondrus crispusand Polysiphonia lanosa. Phytochemistry, 28, 399 (1989).
Gustafson, K.R., J.H. Cardellina Ii, R.W. Fuller, O.S. Weislow, R.F. Kiser, K.M. Snader, G.M.L. Patterson, and M.R. Boyd: Aids-Antiviral Sulfolipids from Cyanobacteria (Blue-Green Algae). J. Natl. Cancer Inst, 81, 1254 (1989).
Gordon, D.M., and S.J. Danishefsky: Synthesis of a Cyanobacterial Sulpholipid: Confirmation of its Structure, Stereochemistry, and Anti-HIV-1 Activity. J. Am. Chem. Soc, 114, 659 (1992).
Son, B.W., Y.J. Cho, N.K. Kim, and H.D. Choi: New Glyceroglycolipids from the Brown Alga Sargassum thunbergii. Bull. Korean Chem. Soc, 13, 584 (1992).
Kitagawa, I., Y. Hamamoto, and J. Kobayashi: Sulfonoglycolipid from the Sea Urchin Antocidaris crassispinaA. Agassiz. Chem. Pharm. Bull., 27, 1934 (1979).
Costantino, V., E. Fattorusso, and A.Mangoni: The Stereochemistry of Crasserides. J. Nat. Prod., 57, 1726 (1994).
Hakomori, S.: Chemistry of Glycosphingolipids. In: Handbook of Lipid Research, J. N. KANFER and S. Hakomori, eds. Vol. 3, p. 327. New York, London: Plenum Press. 1983.
Nojiri, H., F. Takaku, Y. Terui, Y Miura, and M. Saito: Ganglioside GM3: an Acidic Membrane Component that Increase During Macrophage-like Cell Differentiation Can Induce Monocytic Differentiation of Human Myeloid and Monocytoid Leukemic Cell Lines HL-60 and U937. Proc Natl. Acad. Sci. USA, 83, 782 (1986).
Hanai, N., T. Dohi, G.A. Nores, and S. Hakomori: A Novel Ganglioside, De-N-acetyl-GM3 (II3NeuNH2LacCer), Acting as a Strong Promoter fro Epidermial Growth Factor Receptor Kinase and as a Stimulator for Cell Growth. J. Biol. Chem., 263, 6296 (1988).
Ishida, R., H. Shirahama, and T. Matsumoto: Coralipid, a New Glycosphingolipid from the Red Alga Corallina pilulifera. Chem. Lett., 9 (1993).
Irie, A., H. Kubo, and M. Hoshi: Glucosylceramide Having a Novel Tri-Unsaturated Long-Chain Base from the Spermatozoa of the Starfish Asterias amurensis. J. Biochem., 107, 578 (1990).
Schmitz, F.J., and F.J. Mcdonald: Isolation and Identification of Cerebrosides from the Marine Sponge Chondrilla nucula. J. Lipid Res., 15, 158 (1974).
Hirsch, S., and J. Kashman: Structure of Ceramides and Cerebrosides, New Glycosphingolipids from Marine Organisms. Tetrahedron, 45, 3873 (1989).
Hayashi, A., Y. Nishimura, and T. Matsubara: Occurence of Ceramide Digalactoside as the Main Glycosphingolipid in the Marine Sponge Halichondria japonica. Biochim. Biophys. Acta. 1083, 179 (1991).
Endo, M., M. Nakagawa, Y. Hamamoto, and M. Ishihama: Pharmacologically Active Substances from Southern Pacific Marine Invertebrates. Pure Appl. Chem., 58, 387 (1986).
Nagle, D.G., W.C. Mcclatchey, and W.H.Gerwick: New Glycosphingolipids from the Marine Sponge Halichondria panicea. J. Nat. Prod., 55, 1013 (1992).
Costantino, V., E. Fattorusso, and A.Mangoni: Glycolipids from Sponges, I. Glycosyl Ceramide Composition of the Marine Sponge Agelas clathrodes. Liebigs Ann. Chem., 1471 (1995).
CAFIERI, R, E. Fattorusso, A. Mangoni, and TAGLIALATELA-Scafati: Glycolipids from Sponges, II. Glycosyl Ceramide Composition of the Marine Sponge Agelas longissima. Liebigs Ann. Chem., 1477 (1995).
Sugita, M.: Studies on Glycosphingolipids of the Starfish, Asterina pectinifera. I. The Isolation and Characterization of Ceramide Mono-and Di-Hexosides. J. Biochem., 82, 1307 (1977).
Komori, T., Y. Sanechika, Y. Ito, J. Matsuo, T. Nohara, and T. Kawasaki: Strukturen eines neuen Cerebrosidgemischs und von Nucleosiden aus dem Seestern Acantaster planci. Liebigs Ann. Chem., 653 (1980).
Kawano, Y, R. Higuchi, R. Isobe, and T. Komori: Glycosphingolipids from the Starfish Acanthaster planci. Isolation and Structure of Six New Cerebrosides. Liebigs Ann. Chem., 19 (1988).
Irie, A., H. Kubo, F. Inagaki, and M. Hoshi: Ceramide Dihexosides from the Spermatozoa of the Starfish, Asterias amurensis, Consist of Gentobiosyl-, Cellobio-syl-, and Lactosylceramide. J. Biochem. 108, 531 (1990).
Higuchi, R., J.X. Jhou, K. Inukai, and T. Komori: Glycosphingolipids from the Starfish Asterias amurensis versicolor, 1. Isolation and Structure of Six New Cerebrosides, Asteriacerebrosides A-F, and two Known Cerebrosides, Astrocerebroside A and Acanthacerebroside C. Liebigs Ann. Chem., 745 (1991).
Higuchi, R., M. Kagoshima, and T. Komori: Glicosphingolipids from the Starfish Astropecten latespinosus, I. Structure of Three New Cerebrosides, Astrocerebrosides A, B, and C, and of Related Nearly Homogeneous Cerebrosides. Liebigs Ann. Chem., 659 (1990).
Kubo, H., A. Irie, F. Inagaki, and M. Hoshi: Melibiosyl Ceramide as the Sole Ceramide Dihexoside from the Eggs of the Sea Urchin Anthocidaris crassispina. J. Biochem., 104, 755 (1988).
Batrakov, S.G., V.B. Muratov, O.G. Sakandelidze, A.V. Sulima, and B.V. Rosynov: Cerebrosides of the Far-East Sea Cucumber Cucumaria japonica. Bioorg. Khim., 9, 539 (1983).
Shimomura, K., S. Hanjura, P. F. Ki, and Y Ishimoto: An Unusual Glucocerebroside in the Crustacean Nervous System. Science, 220, 1392 (1983).
Karlsson, K.A., H. Leffler, and B.E. Samuelsson: Characterization of Cerebroside (Monoglycosylceramide) from the Sea Anemone Metridium senile. Identification of the Major Long-chain Base as an Unusual Dienic Base with a Methyl Branch at a Double Bond. Biochim. Biophys. Acta, 574, 79 (1979).
Yamaguchi, Y, K. Konda, and A. Hayashi: Studies on the Chemical Structure of Neutral Glycosphinolipids in Eggs of the Sea Hare Aplysia Juliana. Biochim. Biophys. Acta, 1165, 110 (1992).
Sugiyama, S., M. Honda, and T. Komori: The Stereochemistry of the Four Diastereomers of the Phytosphingosine. Liebigs Ann. Chem., 1069 (1990).
Sugiyama, S., M. Honda, and T. Komori: Synthesis of Acanthacerebroside A from the Starfish Acanthaster planci. Liebigs Ann. Chem., 1063 (1990).
Matsubara, T., and A. Hayashi: Structural Studies on Glycolipid of Shellfish. III. Novel Glycolipids from Turbo cornutus. J. Biochem., 89, 645 (1981).
Matsubara, T., and A. Hayashi: Structural Studies on Glycolipids of Shellfish. V. Gala-6 Series Glycosphingolipids of the Marine Snail Chlorostoma argyrostoma turbinatum. J. Biochem., 99, 1401 (1986).
Li, H., S. Matsunaga, and N. Fusetani: Halicylindrosides, Antifungal and Cytotoxic Cerebrosides from the Marine Sponge Halichondria cylindrata. Tetrahedron, 51, 2273 (1995).
Natori, T., Y. Koezuka, and T. Higa: Agelasphin, Novel α-Galactosylceramides from the Marine Sponge Agelas mauritiana. Tetrahedron Lett., 34, 5591 (1993).
Akimoto, K., T. Natori, and M. Morita: Synthesis and Stereochemistry of Agelasphin-9b. Tetrahedron Lett., 35, 5593 (1993).
Motoki, K., E. Kobayashi, T. Uchida, H. Fukushima, and Y. Koezuka: Antitumor Activity of α-, β-Monogalactosylceramides and Four Diastereomers of an α-Galactosylceramide. Bioorg. Med. Chem. Lett., 5, 705 (1995).
Morita, M., T. Natori, K. Aktmoto, T. Osawa, H. Fukushima, and Y. Koezuka: Syntheses of α-, β-Monoglycosylceramides and Four Diastereomers of an α-Galactosylceramide. Bioorg. Med. Chem. Lett., 5, 699 (1995).
Kawano, Y., R. Higuchi, and T. Komori: Achantalactoside A and B, Two New Ceramide Lactosides from the Starfish Acanthaster planci. Liebigs Ann. Chem., 1181 (1988).
Sweeley, C.C., and B. Klionskt. Fabry’s Disease. Classification as a Sphingolipidosis and Partial Characterization of a Novel Glycolipid. J. Biol. Chem., 238, 3148 (1963).
Yamaguchi, Y, M. Otha, and A. Hayashi: Structural Elucidation of a Novel Phosphonoglycolipid in Eggs of a Sea Hare Aplysia Juliana. Biochim. Biophys. Acta, 1165, 160 (1992).
Kubo, H., GJ. Jiang, A. Irie, M. Suzuki, F. Inagaki, and M. Hoshi: A Novel Difucosylated Neutral Glycosphingolipid from the Eggs of the Sea Urchin Hemicentrotus pulcherrimus. I. Purification and Structural Determination of the Glycolipid. J. Biochem., 112, 281 (1992).
Matsubara, T., and A. Hayashi: Structural Studies on Glycolipid of Shellfish. IV. A Novel Pentaglycosyl from Abalone Haliotis japonica. Biochim. Biophys. Acta, 711, 551 (1982).
Matsuura, F.: Phosphonosphingolipid, a Novel Sphingolipid from the Viscera of Turbo cornutus. Chem. Phys. Lipids, 19, 223 (1977).
Hayashi, A., and T. Matsuura: Characterization of Aminoalkylphosphonyl Cerebrosides in Muscle Tissues of Turbo Cornutus. Chem. Phys. Lipids, 22, 9 (1978).
Matsuura, E: The Identification of Aminoalkylphosphonyl Cerebrosides in the Marine Gastropod Monodonta labio. J. Biochem., 85, 433 (1979).
Noda, N., R. Tanaka, K. Miyahara, and T. Kawasaki: TWO Novel Galactosylceramides from the Marine Annelid Marphysa sanguinea. Tetrahedron Lett., 33, 7527 (1992).
Noda, N., R. Tanaka, K. Miyahara, and T. Kawasaki: Isolation and Characterization of a Novel Type of Glycosphingolipid from Neanthes diversicolor. Biochim. Biophys. Acta, 1169, 30 (1993).
Hayashi, A., and T. Matsubara: A new Homologue of Phosphonoglycosphingolipid, N-Methylaminoethylphosphonylgalactosylceramide. Biochim. Biophys. Acta, 1006, 89 (1989).
Araki, S., Y. Komai, and M. Satake: A Novel Sphingophosphonoglycolipid Containing 3-O-Methylgalactose Isolated from the Skin of the Marine Gastropod Aplysia kurodai. J. Biochem., 87, 503 (1980).
Araki, S., S. Abe, S. Odani, S. Ando, N. Fujii, and M. Satake: Structure of a Triphosphonopentaosylceramide Containing 4-0-Methyl-N-acetylglucosamine from the Skin of the Sea Hare Aplysia kurodai. J. Biol. Chem., 262, 14141 (1987).
Araki, S., and M. Satake: Structure of a Novel Diphosphonoglycosphingolipid Isolated from the Skin of Aplysia kurodai. Biochem. Int., 10, 603 (1985).
Araki, S., M. Satake, A. Ando, A. Hayashi, and N. Fujii: Characterization of a Diphosphonopentaosylceramide Containing 3-O-Methylgalactose from the Skin of Aplysia kurodai(Sea Hare). J. Biol. Chem., 261, 5138 (1986).
Hori, T., O. Itasaka, H. Inoue, and K. Yamada: Structural Components of the Pyridine-Insoluble Sphingolipid from Corbicula Sandai, and the Distribution in Other Species. J. Biochem., 56, 477 (1964).
Abe, S., Y. Watanabe, S. Araki, T. Kumanishi, and M. Satake: Immunochemical and Histochemical Studies on a Phosphonoglycosphingolipid, SGL-II, isolated from the Sea Gastropod Aplysia kurodai. J. Biochem., 104, 220 (1988).
Araki, S., S. Abe, S. Ando, N. Fujii, and M. Satake: Isolation and Characterization of a Novel 2-Aminoethylphosphonyl Glycosphingolipid from the Skin of the Sea Hare Aplysia kurodai. J. Biochem., 101, 145 (1987).
Matsubara, T., and A. Hayashi: Occurrence of Phosphonotetraglycosyl Ceramide in the Sea Hare Dolabella auricolaria. Biochim. Biophys. Acta, 1166, 55 (1993).
Abe S., S. Araki, M. Satake, S. Fujiwara, K. Kon, and S. Ando: Structure of Triphosphonoglycosphongolipid containing N-Acetylgalactosamine-6-0-2-ami-noethylphosphonate in the Nervous System of Aplysia kurodai. J. Biol. Chem., 266, 9939 (1991).
Araki, S., S. Abe, S. Ando, K. Kon, N. Fujiwara, and M. Satake: Structure of Phosphonoglycosphingolipid Containing Pyruvylated Galactose in Nerve Fibres of Aplysia kurodai. J. Biol. Chem., 264, 19922 (1989).
Araki, S., S. Abe, M. Satake, A. Hayashi, K. Kon, and S. Ando: Novel Phospho-noglycosphingolipids Containing Pyruvylated Galactose from the Nervous System of Aplysia kurodai. Eur. J. Biochem., 198, 689 (1991).
Garegg, P.J., P.-E. Jansson, P. Lindberg, F. Lindh, J. LöNngren, I. KVANRSTRöM, and W. Nimmich: Configuration of the Acetal Carbon Atom of Pyruvic Acid Acetals in Some Bacterial Polysaccharides. Carbohydr. Res., 78, 127 (1980).
Araki, S., S. Abe, S. Yamada, M. Satake, N. Fujiwara, K. Kon, and S. Ando: Characterization of Two Novel Pyruvylated Glycosphingolipids Containing 2′-Aminoethylphosphoryl( →6)-galactose from the Nervous System of Aplysia kurodai. J. Biochem., 112, 461 (1992).
Yamada, S., S. Araki, S. Abe, K. Kon, S. Ando, and M. Satake: Structural Analysis of a Novel Triphosphonoglycosphingolipid from the Egg of the Sea Hare Aplysia kurodai. J. Biochem., 117, 794 (1995).
Hoshi, M., and Y. Nagai: Novel Sialosphingolipids from the Spermatozoa of the Sea Urchin Anthocidaris crassispina. Biochim. Biophys. Acta, 388, 152 (1975).
Shashkov, A.S., G.P. Smirnova, N.V. Cekareva, and J. Dabrowski: Structural Study of Sialoglycolipids from the Sea Urchin Tripneustes ventricosaGonads using 1H-and 13C-NMR Spectroscopy. Bioorg. Khim., 12, 789 (1986).
Kochetkov, N.K., G.R Smirnova, and I.S. Glukhoded: Structure of Sialolipids from the Gonads of the Sea Urchin Strongylocentrotus nudus. Bioorg. Khim., 4, 1093 (1978).
Kubo, H., and M. Hoshi: Immunochemical Study of the Distribution of a Ganglioside in Sea Urchin Eggs. J. Biochem., 108, 193 (1990).
Chekareva, N.V., G.R Smirnova, and N.K. Kochetkov: Gangliosides of the Holothurian Cucumaria japonicaSemper. Bioorg. Khim., 17, 398 (1991).
Chekareva, N.V., G.R Smirnova, and N.K. Kochetkov: Gangliosides from two Species of Ophiuria, Ophtocoma echinataand Ophiomastix annulosaClark. Bioorg. Khim., 17, 387 (1991).
Smirnova, G.R, N.V. Chekareva, and N.K. Kochetkov: Gangliosides of Ophiura sarsi. Bioorg. Khim., 12, 507 (1986).
Yamamoto, T., T. Teshima, U. Saitoh, M. Hoshi, and T. Shiba: Synthesis of Ganglioside M5 from Sea Urchin Eggs (Anthocidaris crassispina). Tetrahedron Lett., 35, 2701 (1994).
Kochetkov, N.K., G.R Smirnova, N.V. Chekareva: Isolation and Structural Studies on a Sulfated Sialosphingolipid from the Sea Urchin Echinocardium cordatum. Biochim. Biophys. Acta, 424, 274 (1976).
Smirnova, G.R, N.V. Chekareva, and N.K. Kochetkov: Structure of Sialoglycolipids from the Gonad Tissue of the Sea Urchin Echinarachnius parma. Bioorg. Khim., 6, 1667 (1980).
Smirnova, G.R, N.V. Chekareva, and N.K. Kochetkov: Structure of a Minor Sialoglycolipid from the Sea Urchin Echinocardium cordatum. Bioorg. Khim., 4, 937 (1978).
Smirnova, G.R, I.S. Glukhoded, and N.K. Kochetkov: Gangliosides of the Starfish Lethasterias fuska. Bioorg. Khim., 12, 679 (1986).
Prokazova, N.V, A.T. Mikhailov, S.L. Kocharov, L.A. Malchenko, N.D. Zvezdina, G. Buznikov, and L.D. Bergelson: Unusual Gangliosides of Eggs and Embryos of the Sea Urchin Strongylocentrotus intermedius. Eur. J. Biochem., 115, 671 (1981).
Smirnova, G.R, N.K. Kochetkov, and V.L. Sadovskaya: Gangliosides from the Starfish Aphelasterias japonica, Evidence for a New Linkage Between Two N-Glycolylneuraminic Acid Residues through the Hydroxy Group of the Glycolyc Acid Residue. Biochim. Biophys. Acta, 920, 47 (1987).
Kochetkov, N.K., G.R Smirnova, and I.S. Glukhoded: Gangliosides with Sialic Acid Bound to N-Acetylgalactosamine from Hepatopancreas of the Starfish, Evasterias retiferaand Asterias amurensis. Biochim. Biophys. Acta, 712, 650 (1982).
Smirnova, G.R, I.S. Glukhoded, and N.K. Kochetkov: A Branched Disialoganglio-side Containing N-Acetylgalactosamine from the Starfish Asterias rubens. Bioorg. Khim., 14, 636 (1988).
Smirnova, G.R, and N.K. Kochetkov: Gangliosides with Sialic Acid Located in the Inner Part of the Carbohydrate Chain Isolated from the Starfish Luidia quinaria bispinosa. Bioorg. Khim., 11, 1650 (1985).
Smirnova, G.R: Gangliosides with a Sialic Acid Residue in the Inner Part of the Oligosaccharide Chain and with a Terminal Galactofuranose Residue from the Starfish Achantaster planci. Bioorg. Khim., 16, 830 (1990).
Sugita, M.: Studies on the Glycosphingolipids of the Starfish, Asterina pectinifera. III. Isolation and Structural Studies of Two Novel Gangliosides Containing Internal Sialic Acid Residues. J. Biochem., 86, 765 (1979).
Sugita, M.: Studies on Glycosphingolipids of the Starfish, Asterina pectinifera. II. Isolation and Characterization of a Novel Ganglioside with an Internal Sialic Acid Residue. J. Biochem., 86, 289 (1979).
Glukhoded, I.S., G.R Smirnova, and N.K. Kochetkov: Structures of Gangliosides from the Body of the Starfish Patina pectinifera. Bioorg. Khim., 16, 839 (1990).
Higuchi, R., K. Inagaki, T. Natori, T. Komori, and S. Kawajiri: Glycosphingolipids from the Starfish Asterina pectinifera. Structure of Three Ganglioside Molecular Species and a Homogeneous Ganglioside, and Biological Activity of the Ganglioside. Liebigs Ann. Chem., 1 (1991).
Smirnova, G.R, and N.K. Kochetkov: A Novel Sialylglycolipid from Hepatopancreas of the Starfish Patiria pectinifera. Biochim. Biophys. Acta, 618, 486 (1980).
Hakomori, S.: Chemistry of Glycosphingolipids. In: Handbook of Lipid Research, (Kanfer, J.N. and S. Hakomori eds.) Vol. 3, p. 61. New York, London: Plenum Press. 1983.
Kochetkov, N.K., and G.R Smirnova: A Disialoglycolipid with Two Sialic Acid Residue Located in the Inner Part of the Oligosaccharide Chain from the Hepatopancreas of the Starfish Patiria pectinifera. Biochim. Biophys. Acta, 759, 192 (1983).
Soriente, A., T. Bisogno, A. Gambacorta, I. Romano, C. Sili, A. Trincone, and G. Sodano: Reinvestigation of Heterocyst Glycolipids from the Cyanobacterium Anabaena cylindrica. Phytochemistry, 38, 641 (1995).
Soriente, A., G. Sodano, A. Gambacorta, and A. Trincone: Structure of the Heterocyst Glycolipids of Marine Cyanobacterium Nodularia harveyana. Tetrahedron, 48, 5375 (1992).
Harada, N., A. Saito, H. Ono, J. Gawronsky, K. Gawronska, T. Sagioka, H. Uda, and T. Kurki: A CD Method for Determination of Absolute Stereochemistry of Acyclic Glycols. 1. Application of the CD Exciton Chirality Method to Acyclic 1,3-Dibenzoate Systems. J. Am. Chem. Soc, 113, 3842 (1991).
Dale, J.A., and H.S. Mosher: Nuclear Magnetic Resonance Enantiomer Reagents. Configurational Correlation via Nuclear Magnetic Resonance Chemical Shifts of Diastereomeric Mandelate, O-Methylmandelate, and α-Metoxy-a-trifluoromethylphenylacetate (MTPA) Esters. J. Am. Chem. Soc, 95, 512 (1973).
Mori, K., and Z.-H. Qian: Synthesis of (3R, 25R)-3,25-Dihydroxyhexacosyl-a-D-glucopyranoside, the Heterocyst Glycolipid of the Marine Cyanobacterium Nodularia harveyana. Liebigs Ann. Chem., 35 (1994).
Soriente, A., A. Laudisio, M. Giordano, and G. Sodano: Enzymatic Desymmetriza-tion of a Prochiral 1,3,5-Pentanetriol Derivative. Application to the Synthesis of a Cyanobacterial Heterocyst Glycolipid. Tetrahedron Asymm., 6, 859 (1995).
Gambacorta, A., A. Soriente, A. Trincone, and G. Sodano: Biosynthesis of the Heterocyst Glycolipids in the Cyanobacterium Anabaena cylindrica. Phytochemistry, 39, 771 (1995).
Soriente, A., A. Gambacorta, A. Trincone, C. Sili, M. Vincenzini, and G. Sodano: Heterocyst Glycolipids of the Cyanobacterium Cyanospira Rippkae. Phytochemistry, 33, 393 (1993).
Makariewa, T.N., V.A. Denisenko, V.A. Stonik, Y.M. Milgrom, and Y.V. Rashkes: Rhizochalin, a Novel Antimicrobial Secondary Metabolite from the Sponge Rhizochalina incrustata. Tetrahedron Lett., 30, 6581 (1989).
Fusetani, N., N.S. Ata, N. Asai, and S. Matsunaga: Isolation and Structure Elucidation of Erylusamine B, a New Class of Marine Natural Products which Blocks an IL-6 Receptor, from the Marine Sponge Erylus placenta. Tetrahedron Lett., 34, 4067 (1993).
Partridge, J.J., V. Toome, and M.R. Uskokovic: A Stereoselective Synthesis of the 24(/?),25-Dihydroxycholesterol Side Chain. J. Am. Chem. Soc, 98, 3739 (1976).
Findlay, J.A., Z.-Q. He, and L.A. Calhoun: Forbesin, a Novel Sulphated Glycolipid from the Starfish Asterias forbesi. J. Nat. Prod., 53, 1015 (1990)
Watanabe, J., S. Abe, S. Araki, T. Kumanishi, and M. Satake: Characterization of Phosphonoglycosphingolipids Containing Pyruvate: Localization in AplysiaNerve Bundles. J. Biochem., 106, 972 (1989).
Morita, M., K. Motoki, K. Akimoto, T. Natori, T. Sakai, E. Sawa, K. Yamaji, Y. Koezuka, E. Kobayashi, and H. Fukushima: Structure-Activity Relationship of α-Galactosylceramides against B16-Bearing Mice. J. Med. Chem., 38, 2176 (1995).
Kobayashi, E., K. Motoki, Y. Yamaguchi, T. Uchida, H. Fukushima, and Y. Koezuka: Enhancing Effect of α-, β-Monoglycosylceramides on Natural Killer Cell Activity. Bioorg. Med. Chem. Lett., 4, 615 (1996).
Kishimoto, T.: Interleukin-6 and Its Receptors: a Paradigm for Cytokines. Science, 258, 593 (1992).
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Fattorusso, E., Mangoni, A. (1997). Marine Glycolipids. In: Fortschritte der Chemie organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products. Fortschritte der Chemie organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products, vol 72. Springer, Vienna. https://doi.org/10.1007/978-3-7091-6527-0_3
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