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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

  1. 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.

    Google Scholar 

  2. Gunstone, F.D., J.L. Harwood, and F.D.Padley: The Lipid Handbook, p. 12. London: Chapman & Hall. 1994.

    Google Scholar 

  3. 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.

    Google Scholar 

  4. Rajagopal, M.V., and K. Sohonie: Studies on the Sea Anemone Gyrostomasp. Biochem. J., 65, 34 (1957).

    CAS  Google Scholar 

  5. Nagai, Y., and Y. Isono: Occurrence of Animal Sulfolipid in the Gametes of Sea Urchins. Jpn. J. Exp. Med., 35, 315 (1965).

    CAS  Google Scholar 

  6. 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).

    CAS  Google Scholar 

  7. Isono, Y: Changes of Glycolipids during Early Development of Sea Urchin Embryos. Jpn. J. Exp. Med., 37, 87 (1967).

    CAS  Google Scholar 

  8. Nichols, B.W., and B.J.B. Woods: New Glycolipid Specific to Nitrogen-Fixing Blue-Green Algae. Nature, 217, 767 (1968).

    Google Scholar 

  9. Walsby, A.E., and B.W. Nichols: Lipid Composition of Heterocysts. Nature, 221,673 (1969).

    CAS  Google Scholar 

  10. 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).

    CAS  Google Scholar 

  11. Koezuka, I., M. Kloppenburg, and H. Wiegandt: Characterization of Gangliosides from Fish Brain. Biochim. Biophys. Acta, 210, 299 (1970).

    Google Scholar 

  12. Komai, Y, S. Mitsukawa, and M. Satake: Glycolipids in Nervous Tissue of Invertebrates. J. Biochem., 70, 367 (1971).

    CAS  Google Scholar 

  13. Hayashi, A., and F. Matsuura: Isolation of a New Sphingophosphonolipid Containing Galactose from the Viscera of Turbo cornutus. Biochim. Biophys. Acta, 248, 133 (1971).

    CAS  Google Scholar 

  14. 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).

    CAS  Google Scholar 

  15. 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).

    Google Scholar 

  16. 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).

    Google Scholar 

  17. Matsubara, T., and A. Hayashi: The Existence of Branched Structure in the Sugar Moiety of Oyster Sphingoglycolipid. J. Biochem., 74, 853 (1973).

    CAS  Google Scholar 

  18. 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).

    CAS  Google Scholar 

  19. 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).

    CAS  Google Scholar 

  20. 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).

    Google Scholar 

  21. 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).

    CAS  Google Scholar 

  22. 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).

    Google Scholar 

  23. Lambein, F., and C.P. Wolk: Structural studies on the Glycolipid from the Envelope of the Heterocyst of Anabaene cylindrica. Biochemistry, 12, 791 (1973).

    CAS  Google Scholar 

  24. Kochetkov, N.K., and G.P. Smirnova: Glycolipids of Marine Invertebrates. Adv. Carbohydr. Chem. Biochem., 44, 387 (1986).

    CAS  Google Scholar 

  25. Hori, T., and M. Sugita: Sphingolipids in Lower Animals. Prog. Lipid Res., 32, 25 (1993).

    CAS  Google Scholar 

  26. 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.

    Google Scholar 

  27. 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).

    Google Scholar 

  28. 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).

    Google Scholar 

  29. 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).

    CAS  Google Scholar 

  30. 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).

    Google Scholar 

  31. 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).

    CAS  Google Scholar 

  32. 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).

    CAS  Google Scholar 

  33. 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).

    CAS  Google Scholar 

  34. 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).

    Google Scholar 

  35. 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).

    CAS  Google Scholar 

  36. 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).

    Google Scholar 

  37. Sata, N., N. Asai, S. Matsunaga, and N. Fusetani: Erylusamines, Interleukin-6 Receptor Antagonists, from the Marine Sponge Erylus placenta. Tetrahedron, 50, 1093 (1994).

    Google Scholar 

  38. Kubo, H., A. Irie, F. Inagaki, and M. Hoshi: Gangliosides from the Eggs of the Sea Urchin Anthocidaris crassispina. J. Biochem., 108, 185 (1990).

    CAS  Google Scholar 

  39. 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).

    CAS  Google Scholar 

  40. 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).

    CAS  Google Scholar 

  41. Sweeley, C.C., and R.V.P. Tao: Gas Chromatographie Estimation of Carbohydrates in Glycosphingolipids. Methods Carbohydr. Chem., 6, 8 (1972).

    CAS  Google Scholar 

  42. Svennerholm, L.: Quantitative Estimation of Sialic Acid. III. An Anion-Exchange-Resin Method. Acta Chem. Scand., 12, 547 (1958).

    CAS  Google Scholar 

  43. Hakomori, S.: Rapid Permethylation of Glycolipids and Polysaccharides, Catalyzed by Methylsulfinyl Carbanion in Dimethyl Sulfoxide. J. Biochem., 55, 205 (1964).

    CAS  Google Scholar 

  44. 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).

    Google Scholar 

  45. 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).

    CAS  Google Scholar 

  46. 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).

    CAS  Google Scholar 

  47. Weissman, B., and D.F. Hinrichsen: Mammalian α-Acetylagalactosaminase. Occurrence, Partial Purification, and Action on Linkages in Submaxillary Mucins. Biochemistry, 8, 2034 (1969).

    Google Scholar 

  48. Gatt, S., and M.M. Rapport: Isolation of β-Galactosidase and β-Glucosidase from Brain. Biochim. Biophys. Acta, 113, 567 (1966).

    CAS  Google Scholar 

  49. 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).

    CAS  Google Scholar 

  50. 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).

    Google Scholar 

  51. 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).

    CAS  Google Scholar 

  52. 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).

    CAS  Google Scholar 

  53. Laine, R.A., and O. Renkonen: Ceramide Di-and Trihexosides of Wheat Flour. Biochemistry, 13, 2837 (1974).

    CAS  Google Scholar 

  54. Laine, R.A., and O. Renkonen: Analysis of Anomeric Configurations in Glyceroglycolipids and Glycosphingolipids by Chromium Trioxide Oxidation. J. Lipid Res., 16, 102 (1975).

    CAS  Google Scholar 

  55. 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).

    CAS  Google Scholar 

  56. 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).

    Google Scholar 

  57. 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).

    CAS  Google Scholar 

  58. 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).

    CAS  Google Scholar 

  59. 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).

    Google Scholar 

  60. Cafieri, F., E. Fattorusso, Y. Mahajnah, and A.Mangoni: Longiside, a Novel Digalactosylceramide from the Caribbean Sponge Agelas longissima. Liebigs Ann. Chem., 1187 (1994).

    Google Scholar 

  61. 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).

    Google Scholar 

  62. 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).

    CAS  Google Scholar 

  63. VAN Hummel, H.C.: Chemistry and Biosynthesis of Plant Galactolipids. Fortschr. Chem. Org. Naturst., 32, 267 (1975).

    Google Scholar 

  64. Dembitsky, V. M., O.A. Rozentsvet, E.E. and Pechenkina: Glycolipids, Phospholipids and Fatty Acids of Brown Algae Species. Phytochemistry, 29, 3417 (1990).

    CAS  Google Scholar 

  65. Jones, A.L., and J.L. Harwood: Comparative Aspects of Lipid Metabolisms in Marine Algae. Biochem. Soc. Trans., 15, 482 (1987).

    CAS  Google Scholar 

  66. 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).

    CAS  Google Scholar 

  67. Dembitsky, V.M., T. Rezanka, and O.A. Rozentsvet: Lipid Composition of Three Macrophytes from the Caspian Sea. Phytochemistry, 33, 1015 (1993).

    CAS  Google Scholar 

  68. 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).

    CAS  Google Scholar 

  69. 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).

    CAS  Google Scholar 

  70. 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).

    CAS  Google Scholar 

  71. Jiang, Z.D., and W.H. Gerwick: Galactolipid from the Temperate Red Marine Alga Gracilariopsis lemaneiformis. Phytochemistry, 29, 1433 (1990).

    CAS  Google Scholar 

  72. Arao, T., and M. Yamada: Positional Distribution of Fatty Acids in Galactolipids of Algae. Phytochemistry, 28, 805 (1989).

    CAS  Google Scholar 

  73. 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).

    CAS  Google Scholar 

  74. Jiang, Z.D., and W.H. Gerwick: An Aldehyde-Containing Galactolipid from the Red Alga Gracilariopsis lemaneiformis. Lipids, 26, 960 (1991).

    CAS  Google Scholar 

  75. Fusetani, N., and Y. Hashimoto: Structures of Two Water Soluble Hemolysins Isolated from the Green Alga Ulva pertusa. Agric. Biol. Chem., 39, 2021 (1975).

    CAS  Google Scholar 

  76. Son, B.W.: Glycolipids from Gracilaria verrucosa. Phytochemistry, 29, 307 (1990).

    CAS  Google Scholar 

  77. Son, B.W.: Glycolipid from the Korean Marine Red Alga Gracilaria verrucosa. Bull. Korean Chem. Soc, 9, 264 (1988).

    CAS  Google Scholar 

  78. 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).

    CAS  Google Scholar 

  79. Pettit, G.R., A.L. Jones, and L.H.Harwood: Lipids of the Marine Red Algae, Chondrus crispusand Polysiphonia lanosa. Phytochemistry, 28, 399 (1989).

    Google Scholar 

  80. 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).

    CAS  Google Scholar 

  81. 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).

    CAS  Google Scholar 

  82. 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).

    CAS  Google Scholar 

  83. Kitagawa, I., Y. Hamamoto, and J. Kobayashi: Sulfonoglycolipid from the Sea Urchin Antocidaris crassispinaA. Agassiz. Chem. Pharm. Bull., 27, 1934 (1979).

    CAS  Google Scholar 

  84. Costantino, V., E. Fattorusso, and A.Mangoni: The Stereochemistry of Crasserides. J. Nat. Prod., 57, 1726 (1994).

    CAS  Google Scholar 

  85. 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.

    Google Scholar 

  86. 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).

    CAS  Google Scholar 

  87. 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).

    CAS  Google Scholar 

  88. Ishida, R., H. Shirahama, and T. Matsumoto: Coralipid, a New Glycosphingolipid from the Red Alga Corallina pilulifera. Chem. Lett., 9 (1993).

    Google Scholar 

  89. 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).

    CAS  Google Scholar 

  90. Schmitz, F.J., and F.J. Mcdonald: Isolation and Identification of Cerebrosides from the Marine Sponge Chondrilla nucula. J. Lipid Res., 15, 158 (1974).

    CAS  Google Scholar 

  91. Hirsch, S., and J. Kashman: Structure of Ceramides and Cerebrosides, New Glycosphingolipids from Marine Organisms. Tetrahedron, 45, 3873 (1989).

    Google Scholar 

  92. 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).

    CAS  Google Scholar 

  93. Endo, M., M. Nakagawa, Y. Hamamoto, and M. Ishihama: Pharmacologically Active Substances from Southern Pacific Marine Invertebrates. Pure Appl. Chem., 58, 387 (1986).

    Google Scholar 

  94. Nagle, D.G., W.C. Mcclatchey, and W.H.Gerwick: New Glycosphingolipids from the Marine Sponge Halichondria panicea. J. Nat. Prod., 55, 1013 (1992).

    CAS  Google Scholar 

  95. 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).

    Google Scholar 

  96. 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).

    Google Scholar 

  97. 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).

    CAS  Google Scholar 

  98. 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).

    Google Scholar 

  99. 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).

    Google Scholar 

  100. 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).

    CAS  Google Scholar 

  101. 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).

    Google Scholar 

  102. 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).

    Google Scholar 

  103. 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).

    CAS  Google Scholar 

  104. 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).

    CAS  Google Scholar 

  105. Shimomura, K., S. Hanjura, P. F. Ki, and Y Ishimoto: An Unusual Glucocerebroside in the Crustacean Nervous System. Science, 220, 1392 (1983).

    CAS  Google Scholar 

  106. 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).

    CAS  Google Scholar 

  107. 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).

    CAS  Google Scholar 

  108. Sugiyama, S., M. Honda, and T. Komori: The Stereochemistry of the Four Diastereomers of the Phytosphingosine. Liebigs Ann. Chem., 1069 (1990).

    Google Scholar 

  109. Sugiyama, S., M. Honda, and T. Komori: Synthesis of Acanthacerebroside A from the Starfish Acanthaster planci. Liebigs Ann. Chem., 1063 (1990).

    Google Scholar 

  110. Matsubara, T., and A. Hayashi: Structural Studies on Glycolipid of Shellfish. III. Novel Glycolipids from Turbo cornutus. J. Biochem., 89, 645 (1981).

    CAS  Google Scholar 

  111. 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).

    CAS  Google Scholar 

  112. Li, H., S. Matsunaga, and N. Fusetani: Halicylindrosides, Antifungal and Cytotoxic Cerebrosides from the Marine Sponge Halichondria cylindrata. Tetrahedron, 51, 2273 (1995).

    CAS  Google Scholar 

  113. Natori, T., Y. Koezuka, and T. Higa: Agelasphin, Novel α-Galactosylceramides from the Marine Sponge Agelas mauritiana. Tetrahedron Lett., 34, 5591 (1993).

    CAS  Google Scholar 

  114. Akimoto, K., T. Natori, and M. Morita: Synthesis and Stereochemistry of Agelasphin-9b. Tetrahedron Lett., 35, 5593 (1993).

    Google Scholar 

  115. 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).

    CAS  Google Scholar 

  116. 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).

    CAS  Google Scholar 

  117. 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).

    Google Scholar 

  118. 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).

    CAS  Google Scholar 

  119. 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).

    CAS  Google Scholar 

  120. 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).

    CAS  Google Scholar 

  121. 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).

    CAS  Google Scholar 

  122. Matsuura, F.: Phosphonosphingolipid, a Novel Sphingolipid from the Viscera of Turbo cornutus. Chem. Phys. Lipids, 19, 223 (1977).

    CAS  Google Scholar 

  123. Hayashi, A., and T. Matsuura: Characterization of Aminoalkylphosphonyl Cerebrosides in Muscle Tissues of Turbo Cornutus. Chem. Phys. Lipids, 22, 9 (1978).

    CAS  Google Scholar 

  124. Matsuura, E: The Identification of Aminoalkylphosphonyl Cerebrosides in the Marine Gastropod Monodonta labio. J. Biochem., 85, 433 (1979).

    CAS  Google Scholar 

  125. Noda, N., R. Tanaka, K. Miyahara, and T. Kawasaki: TWO Novel Galactosylceramides from the Marine Annelid Marphysa sanguinea. Tetrahedron Lett., 33, 7527 (1992).

    CAS  Google Scholar 

  126. 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).

    CAS  Google Scholar 

  127. Hayashi, A., and T. Matsubara: A new Homologue of Phosphonoglycosphingolipid, N-Methylaminoethylphosphonylgalactosylceramide. Biochim. Biophys. Acta, 1006, 89 (1989).

    CAS  Google Scholar 

  128. 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).

    CAS  Google Scholar 

  129. 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).

    CAS  Google Scholar 

  130. Araki, S., and M. Satake: Structure of a Novel Diphosphonoglycosphingolipid Isolated from the Skin of Aplysia kurodai. Biochem. Int., 10, 603 (1985).

    CAS  Google Scholar 

  131. 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).

    CAS  Google Scholar 

  132. 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).

    CAS  Google Scholar 

  133. 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).

    CAS  Google Scholar 

  134. 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).

    CAS  Google Scholar 

  135. Matsubara, T., and A. Hayashi: Occurrence of Phosphonotetraglycosyl Ceramide in the Sea Hare Dolabella auricolaria. Biochim. Biophys. Acta, 1166, 55 (1993).

    CAS  Google Scholar 

  136. 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).

    CAS  Google Scholar 

  137. 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).

    CAS  Google Scholar 

  138. 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).

    CAS  Google Scholar 

  139. 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).

    CAS  Google Scholar 

  140. 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).

    CAS  Google Scholar 

  141. 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).

    CAS  Google Scholar 

  142. Hoshi, M., and Y. Nagai: Novel Sialosphingolipids from the Spermatozoa of the Sea Urchin Anthocidaris crassispina. Biochim. Biophys. Acta, 388, 152 (1975).

    CAS  Google Scholar 

  143. 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).

    CAS  Google Scholar 

  144. 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).

    CAS  Google Scholar 

  145. Kubo, H., and M. Hoshi: Immunochemical Study of the Distribution of a Ganglioside in Sea Urchin Eggs. J. Biochem., 108, 193 (1990).

    CAS  Google Scholar 

  146. Chekareva, N.V., G.R Smirnova, and N.K. Kochetkov: Gangliosides of the Holothurian Cucumaria japonicaSemper. Bioorg. Khim., 17, 398 (1991).

    CAS  Google Scholar 

  147. 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).

    CAS  Google Scholar 

  148. Smirnova, G.R, N.V. Chekareva, and N.K. Kochetkov: Gangliosides of Ophiura sarsi. Bioorg. Khim., 12, 507 (1986).

    CAS  Google Scholar 

  149. 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).

    CAS  Google Scholar 

  150. 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).

    CAS  Google Scholar 

  151. 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).

    CAS  Google Scholar 

  152. 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).

    CAS  Google Scholar 

  153. Smirnova, G.R, I.S. Glukhoded, and N.K. Kochetkov: Gangliosides of the Starfish Lethasterias fuska. Bioorg. Khim., 12, 679 (1986).

    CAS  Google Scholar 

  154. 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).

    CAS  Google Scholar 

  155. 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).

    CAS  Google Scholar 

  156. 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).

    CAS  Google Scholar 

  157. 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).

    CAS  Google Scholar 

  158. 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).

    CAS  Google Scholar 

  159. 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).

    CAS  Google Scholar 

  160. 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).

    CAS  Google Scholar 

  161. 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).

    CAS  Google Scholar 

  162. 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).

    CAS  Google Scholar 

  163. 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).

    Google Scholar 

  164. Smirnova, G.R, and N.K. Kochetkov: A Novel Sialylglycolipid from Hepatopancreas of the Starfish Patiria pectinifera. Biochim. Biophys. Acta, 618, 486 (1980).

    CAS  Google Scholar 

  165. 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.

    Google Scholar 

  166. 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).

    CAS  Google Scholar 

  167. 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).

    CAS  Google Scholar 

  168. Soriente, A., G. Sodano, A. Gambacorta, and A. Trincone: Structure of the Heterocyst Glycolipids of Marine Cyanobacterium Nodularia harveyana. Tetrahedron, 48, 5375 (1992).

    CAS  Google Scholar 

  169. 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).

    CAS  Google Scholar 

  170. 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).

    CAS  Google Scholar 

  171. 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).

    Google Scholar 

  172. 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).

    CAS  Google Scholar 

  173. Gambacorta, A., A. Soriente, A. Trincone, and G. Sodano: Biosynthesis of the Heterocyst Glycolipids in the Cyanobacterium Anabaena cylindrica. Phytochemistry, 39, 771 (1995).

    CAS  Google Scholar 

  174. Soriente, A., A. Gambacorta, A. Trincone, C. Sili, M. Vincenzini, and G. Sodano: Heterocyst Glycolipids of the Cyanobacterium Cyanospira Rippkae. Phytochemistry, 33, 393 (1993).

    CAS  Google Scholar 

  175. 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).

    Google Scholar 

  176. 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).

    CAS  Google Scholar 

  177. 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).

    CAS  Google Scholar 

  178. 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)

    CAS  Google Scholar 

  179. 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).

    CAS  Google Scholar 

  180. 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).

    CAS  Google Scholar 

  181. 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).

    CAS  Google Scholar 

  182. Kishimoto, T.: Interleukin-6 and Its Receptors: a Paradigm for Cytokines. Science, 258, 593 (1992).

    CAS  Google Scholar 

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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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