Sulfated fucans, fresh perspectives: Structures, functions, and biological properties of sulfated fucans and an overview of enzymes active toward this class of polysaccharide

Glycobiology

Volumn 13, Issue 6, 2003, Pages

  Berteau, Olivier ^a   Mulloy, Barbara ^b  

^a SWEDISH UNIVERSITY OF AGRICULTURAL SCIENCES   (Sweden)

^b NATIONAL INSTITUTE FOR BIOLOGICAL STANDARDS AND CONTROL   (United Kingdom)

Author keywords

Fucan; Fucoidan; Fucoidanase; Fucoidin; Sulfated fucan

Indexed keywords

ALPHA LEVO FUCOSIDASE; ANTICOAGULANT AGENT; ANTIINFLAMMATORY AGENT; ANTIMALARIAL AGENT; ANTIPARASITIC AGENT; ANTITHROMBIN; ANTITHROMBOCYTIC AGENT; ANTIVIRUS AGENT; AZUROCIDIN; FUCAN; FUCOIDIN; FUCOSE; GALACTAN; GLYCOSIDASE; HEPARIN; HEPARIN COFACTOR II; L SELECTIN; PADGEM PROTEIN; POLYSACCHARIDE SULFATE; SCAVENGER RECEPTOR; SERINE PROTEINASE INHIBITOR; TUMOR NECROSIS FACTOR ALPHA; UNCLASSIFIED DRUG;

ALGA; ANTICOAGULATION; ANTIMALARIAL ACTIVITY; ANTIVIRAL ACTIVITY; CELL ADHESION; CELL GROWTH; CELL MIGRATION; CLASSIFICATION; DENSITY; DRUG ACTIVITY; DRUG POTENCY; DRUG STRUCTURE; ENZYME ACTIVITY; ENZYME ANALYSIS; FERTILIZATION; INVERTEBRATE; ISOLATION PROCEDURE; MACROPHAGE; NONHUMAN; PRIORITY JOURNAL; PURIFICATION; REVIEW; STRUCTURE ANALYSIS; SULFATION; THROMBOCYTE ACTIVATION; THROMBOCYTE AGGREGATION INHIBITION;

ANIMALS; ANTICOAGULANTS; ANTITHROMBINS; CARBOHYDRATE SEQUENCE; ENZYMES; MOLECULAR SEQUENCE DATA; POLYSACCHARIDES;

ALGAE; INVERTEBRATA;

EID: 0038618955     PISSN: 09596658     EISSN: None     Source Type: Journal    
DOI: 10.1093/glycob/cwg058     Document Type: Review

References (121)

1. Abdel-Fattah, A.F., Hussein, M.M.D., and Fouad, S.T. (1978) Carbohydrates of the brown seaweed Dictyota dichotoma. Phytochemistry, 17, 741-743.
2. Alves, A.P., Mulloy, B., Diniz, J.A., and Mourao, P.A.S. (1997) Sulfated polysaccharides from the egg jelly layer are species-specific inducers of acrosomal reaction in sperms of sea urchins. J. Biol. Chem., 272, 6965-6971.
3. Alves, A.P., Mulloy, B., Moy, G.W., Vacquier, V.D., and Mourao, P.A.S. (1998) Females of the sea urchin Strongylocentrotus purpuratus differ in the structure of their egg jelly sulphated fucans. Glycobiology, 8, 939-946.
4. Alwayn, I.P., Appel, J.Z., Goepfert, C., Buhler, L., Cooper, D.K., and Robson, S.C. (2000) Inhibition of platelet aggregation in baboons: therapeutic implications for xenotransplantation. Xenotransplantation, 7, 247-257.
5. Anno, K., Terahata, H., Hayashi, Y., and Seno, N. (1966) Isolation and purification of fucoidin from brown seaweed Pelvetia wrightii. Agr. Biol. Chem., 30, 495-499.
6. Bakunina, I.Y., Nedashkovskaia, O.I., Alekseeva, S.A., Ivanova, E.P., Romanenko, L.A., Gorshkova, N.M., Isakov, V.V., Zviagintseva, T.N., and Mikhailov, V.V. (2002) Degradation of fucoidan by the marine protebacterium. Pseudoalteromonas citrea. Microbiology, 71, 41-47.
7. Bernardi, G. and Springer, G. F. (1962) Properties of highly purified fucan. J. Biol. Chem., 237, 75-80.
8. Berteau O., McCort I., Goasdoue N., Tissot B., and Daniel R. (2002) Characterization of a new alpha-L-fucosidase isolated from the marine mollusk Pecten maximus that catalyzes the hydrolysis of alpha-L-fucose from algal fucoidan (Ascophyllum nodosum). Glycobiology, 12, 273-282.
9. Bilan, M.I., Grachev, A.A., Ustuzhanina, N.E., Shashkov, A.S., Nifantiev, N.E., and Usov, A.I. (2002) Structure of a fucoidan from the brown seaweed Fucus evanescens C.Ag. Carbohydr. Res., 337, 719-730.
10. Bisgrove, S.R. and Kropf, D.L. (2001) Cell wall deposition during morphogenesis in fucoid algae. Planta, 212, 648-658.
11. Black, W.A.P. (1954) The seasonal variation in the combined L-fucose content of the common British laminariaceae and fucaceae. J. Sci. Food Agr., 5, 445-448.
12. Boisson-Vidal, C., Haroun, F., Ellouali, M., Blondin, C., Fischer, A.M., De Agostini, A., and Jozefonvicz, J. (1995) Biological activities of polysaccharide from marine algae. Drugs Fut., 20, 1237-1249.
13. Boisson-Vidal, C., Chaubet, F., Chevolot, L., Sinquin, C., Theveniaux, J., Millet, J., Sternberg, C., Mulloy, B., and Fischer, A.M. (2000) Relationship between antithrombotic activities of fucans and their structure. Drug Devel. Res., 51, 216-224.
14. Burtseva, Y.V., Kusaikin, M.I., Sova, V.V., Shevchenko, N.M., Skobun, A.S., and Zvyagintseva, T.N. (2000) Distribution of fucoidan hydrolases and some glycosidases among marine invertebrates. Russ. J. Mar. Biol., 26, 453-456.
15. Chargaff, E., Bancroft, F.W., and Brown, M.S. (1936) Studies on the chemistry of blood coagulation II. On the inhibition of blood clotting by substances of high molecular weight. J. Biol. Chem., 115, 155-156.
16. Chevolot, L., Foucault, A., Kervarec, N., Sinquin, C., Fisher, A.M., and Boisson-Vidal, C. (1999) Further data on the structure of brown seaweed fucans: relationships with anticoagulant activity. Carbohyd. Res., 319, 154-165.
17. Chevolot, L., Mulloy, B., Ratiskol, J., Foucault, A., and Colliec-Jouault, S. (2001) A disaccharide repeat unit is the major structure in fucoidans from two species of brown algae. Carbohyd. Res., 330, 529-535.
18. Chizhov, A.O., Dell, A., Morris, H.R., Haslam, S.M., McDowell, R.A., Shashkov, A.S., Nifant'ev, N.E., Khatuntseva, E.A., and Usov, A.I. (1999) A study of fucoidan from the brown seaweed Chorda filum. Carbohyd. Res., 320, 108-119.
19. Clark, D.L., Su, S.D., and Davidson, E.A. (1997) Saccharide anions as inhibitors of the malaria parasite. Glycoconj. J., 14, 473-479.
20. Colliec, S., Boisson-Vidal, C., and Jozefonvicz, J. (1994) A low molecular weight fucoidan fraction from the brown seaweed Pelvetia caniculata. Phytochemistry, 35, 697-700.
21. Colwell, N.S., Grupe, M.J., and Tollefsen, D.M. (1999) Amino acid residues of heparin cofactor II required for stimulation of thrombin inhibition by sulphated polyanions. Biochim. Biophys. Acta, 1431, 148-156.
22. Côté, R.H. (1959) Disaccharides from fucoidin. J. Chem. Soc., 2248-2254.
23. Daniel, R., Berteau, O., Jozefonvicz, J., and Goasdoue, N. (1999) Degradation of algal (Ascophyllum nodosum) fucoidan by an enzymatic activity contained in digestive glands of the marine mollusc Pecten maximus. Carbohyd Res., 322, 291-297.
24. Daniel, R., Berteau, O., Chevolot, L., Varenne, A., Gareil, P., and Goasdoue, N. (2001) Regioselective desulfation of sulfated L-fucopyranoside by a new sulfoesterase from the marine mollusk Pecten maximus: application to the structural study of algal fucoidan (Ascophyllum nodosum). Eur. J. Biochem., 268, 5617-5628.
25. de Reviers, B., Mabeau, S., and Kloareg, B. (1983) Essai d'interprétation de la structure des fucoidanes en liaison avec leur localisation dans la paroi des phéophycées. Crit. Rev. Biochem., 4, 55-62.
26. Descamps, V., Klarszinsky, O., Barbeyron, T., Cloarec, B., Fritig, B., Jouber, J.M., Plesse, B., and Yvin, J.C. (1998) Fuco-oligosaccharides, enzyme pour leur préparation à partir de fucanes, bacterie productrice de l'enzyme et applications des fuco-oligosaccharides à la protection des plantes. Brevet, FR 2 783 523.
27. Dobashi K., Nishino T., Fujihara M., and Nagumo, T. (1989) Isolation and preliminary characterization of fucose-containing sulfated polysaccharides with blood-anticoagulant activity from the brown seaweed Hizikia fusiforme. Carbohydr. Res., 194, 315-320.
28. Duarte, M.E.R., Cardoso, M.A., Noseda, M.D., and Cerezo, A.S. (2001) Structural studies on fucoidans from the brown seaweed Sargassum stenophyllum. Carbohyd. Res., 333, 281-293.
29. Durig, J., Bruhn, T., Zurborn, K.H., Gutensohn, K., Bruhn, H.D., and Beress, L. (1997) Anticoagulant fucoidan fractions from Fucus vesiculosus induce platelet activation in vitro. Thromb. Res., 85, 479-491.
30. Evans, L.V. (1989) Mucilaginous substances from macroalgae: an overview. Symp. Soc. Exp. Biol., 43, 455-461.
31. Farias, W.R.L., Valente, A.P., Pereira, M.S., and Mourao, P.A.S. (2000) Structure and anticoagulant activity of sulfated galactans - Isolation of a unique sulfated galactan from the red algae Botryocladia occidentalis and comparison of its anticoagulant action with that of sulfated galactans from invertebrates. J. Biol. Chem., 275, 29299-29307.
32. Frenette, P.S. and Weiss, L. (2000) Sulfated glycans induce rapid hematopoietic progenitor cell mobilization: evidence for selectin-dependent and independent mechanisms. Blood, 96, 2460-2468.
33. Furukawa, S. and Fujikawa, T. (1984) Growth and fucoidan sulfatase production in fucoidan-utilizing bacteria from sea sand. Nippon Nogeik. Kaishi, 11, 1123-1126.
34. Furukawa, S.I., Fujikawa, T., Koga, D., and Ide, A. (1992a) Purification and some properties of exo-type fucoidanases from Vibrio sp. N-5. Biosci. Biotech. Biochem., 56, 1829-1834.
35. Furukawa, S.I., Fujikawa, T., Koga, D., and Ide, A. (1992b) Production of fucoidan-degrading enzymes, fucoidanase, and fucoidan sulfatase by Vibrio sp. N-5. Nippon Suisan Gakk., 58, 1499-1503.
36. Gerbst, A.G., Ustuzhanina, N.E., Grachev, A.A., Khatuntseva, E.A., Tsvetkov, D.E., Whitfield, D.M., Berces, A., and Nifantiev, N.E. (2001) Synthesis, NMR, and conformational studies of fucoidan fragments 3. J. Carbohyd. Chem., 20, 821-831.
37. Gerbst, A.G., Ustuzhanina, N.E., Grachev, A.A., Zlotina, N.S., Khatuntseva, E.A., Tsvetkov, D.E., Shashkov, A.S., Usov, A.I., and Nifantiev, N.E. (2002) Synthesis, NMR, and conformational studies of fucoidan fragments 4. J. Carbohyd. Chem., 2(1), 313-324.
38. Giraux, J.L., Matou, S., Bros, A., Tapon-Bretaudiere, J., Letourneur, D., and Fischer, A.M. (1998a) Modulation of human endothelial cell proliferation and migration by fucoidan and heparin. Eur. J. Cell. Biol., 77, 352-359.
39. Giraux, J.L., Tapon-Bretaudiere, J., Matou, S., and Fischer, A.M. (1998b) Fucoidan, as heparin, induces tissue factor pathway inhibitor release from cultured human endothelial cells. Thromb. Haemost., 80, 692-695.
40. Granert, C., Raud, J., Waage, A., and Lindquist, L. (1999) Effects of polysaccharide fucoidin on cerebrospinal fluid interleukin-1 and tumor necrosis factor alpha in Pneumococcal meningitis in the rabbit. Infect. Immun., 67, 2071-2074.
41. Haroun-Bouhedja, F., Ellouali, M., Sinquin, C., and Boisson-Vidal, C. (2000) Relationship between sulfate groups and biological activities of fucans. Thromb. Res., 100, 453-459.
42. Heinzelmann, M., Polk, H.C.J., and Miller, F.N. (1998) Modulation of lipopolysaccharide-induced. monocyte activation by heparin-binding protein and fucoidan. Infect. Immun., 66, 5842-5847.
43. 2+ channels involved in triggering the sea urchin sperm acrosome reaction. J. Biol. Chem., 277, 1182-1189.
44. Hirohashi, N., Vilela-Silva, A.E.S., Mourão, P.A.S., and Vacquier, V.D. (2002) Structural requirements for species-specific induction of the sperm acrosome reaction by sea urchin egg sulfated fucan. Biochem. Biophys. Res. Commun., 298, 403-407.
45. Honya, M., Mori, M., Anzai, M., Araki, Y., and Nisizawa, K. (1999) Monthly changes in the content of fucans, their constituent sugars and sulphate in cultured Laminaria japonica. Hydrobiologia, 398/399, 411-416.
46. Hoshino, T., Hayashi, T., Hayashi, K., Hamada, J., Lee, J.B., and Sankawa, U. (1998) An antivirally active sulfated polysaccharide from Sargassum horneri (TURNER) C. AGARDH. Biol. Pharm. Bull., 21, 730-734.
47. Hsu H.Y., Hajjar D.P., Khan K.M., and Falcone D.J. (1998) Ligand binding to macrophage scavenger receptor-A induces urokinase-type plasminogen activator expression by a protein kinase-dependent signaling pathway. J. Biol. Chem., 273, 1240-1246.
48. Iqbal, M., Flick-Smith, H., and McCauley, J.W. (2000) Interactions of bovine viral diarrhoea virus glycoprotein E(rns) with cell surface glycosaminoglycans. J. Gen. Virol., 81, 451-459.
49. Johnston, D.S., Wright, W.W., Shaper, J.H., Hokke, C.H., Van den Eijnden, D.H., and Joziasse, D.H. (1998) Murine sperm-zona binding, a fucosyl residue is required for a high affinity sperm-binding ligand. A second site on sperm binds a nonfucosylated, beta-galactosyl-capped oligosaccharide. J. Biol. Chem., 273, 1888-1895.
50. Killing, H. (1913) Zur biochemie der Meersalgen. Z. Physiol. Chem., 83, 171-197.
51. Kitamura, K., Matsuo, M., and Yasui, T. (1992) Enzymic degradation of fucoidan by fucoidanase from the hepatopancreas of Patinopecten yessoensis. Biosci. Biotech. Biochem., 56, 490-494.
52. Kloareg, B. (1981) Structure et rôle écophysiologique des parois des algues littorales: contribution à la résistance aux variations de salinité. Physiol. Vég., 17, 731-747.
53. Kloareg, B. (1984) Isolation and analysis of cell walls of the brown marine algae Pelvetia canaliculata and Ascophyllum nodosum. Physiol. Vég., 22, 47-56.
54. Kloareg, B. and Quatrano, R.S. (1988) Structure of the cell walls of marine algae and ecophysiological functions of the matrix polysaccharides. Oceanogr. Mar. Biol. Annu. Rev., 26, 259-315.
55. Kloareg, B., Demarty, M., and Mabeau, S. (1986) Polyanionic characteristic of purified sulphated homofucans from brown algae. Int. J. Biol. Macromol., 8, 380-386.
56. Larsen, B., Haug, A., and Painter, T.J. (1966) Sulphated polysaccharides in brown algae - I. Isolation and preliminary characterisation of three sulphated polysaccharides from Ascophyllum nodosum (L.) Le JOL. Acta Chem. Scand., 20, 219-230.
57. Lasky, L.A. (1995) Selectin-carbohydrate interactions and the initiation of the inflammatory response. Annu. Rev. Biochem., 64, 113-139.
58. Leite, E.L., Medeiros, M.G.L., Rocha, H.A.O., Farias, G.G.M., da Silva, L.F., Chavante, S.F., de Abreu, L.D., Dietrich, C.P., and Nader, H.B. (1998) Structure and pharmacological activities of a sulfated xylofucoglucuronan from the alga Spatoglossum schroederi. Plant Sci., 132, 215-228.
59. Lloyd, P.F. and Lloyd, K.O. (1963) Sulphatases and sulphated polysaccharide in the viscera of marine mollusc. Nature, 199, 287.
60. Logeart, D., Prigent-Richard, S., Boisson-Vidal, C., Chaubet, F., Durand, P., Jozefonvicz, J., and Letourneur, D. (1997) Fucans, sulfated polysaccharides extracted from brown seaweeds, inhibit vascular smooth muscle cell proliferation. II. Degradation and molecular weight effect. Eur. J. Cell. Biol., 74, 385-390.
61. Mabeau, S., Kloareg, B., and Joseleau, J.P. (1990) Fractionation and analysis of fucans from brown algae. Phytochemistry, 29, 2441-2445.
62. Marais, M.-F. and Joseleau, J.-P. (2001) A fucoidan fraction from Ascophyllum nodosum. Carbohydr. Res., 336, 155-159.
63. Maruyama, H., Nakajima, J., and Yamamoto, I. (1987) A study on the anticoagulant and fibrinolytic activities of a crude fucoidan from the edible brown seaweed Laminaria religiosa, with special reference to its inhibitory effect on the growth of sarcoma-180 ascites cells subcutaneously implanted into mice. Kitasato Arch. Exp. Med., 60, 105-121.
64. Mauray, S., de Raucourt, E., Talbot, J.C., Dachary-Prigent, J., Jozefowicz, M., and Fischer, A.M. (1998) Mechanism of factor IXa inhibition by antithrombin in the presence of unfractionated and low molecular weight heparins and fucoidan. Biochim. Biophys. Acta, 1387, 184-194.
65. McCormick, C.J., Tuckwell, D.S., Crisanti, A., Humphries, M.J., and Hollingdale, M.R. (1999) Identification of heparin as a ligand for the A-domain of Plasmodium falciparum thrombospondin-related adhesion protein. Mol. Biochem. Parasitol., 100, 111-124.
66. McCormick, C.J., Newbold, C.I., and Berendt, A.R. (2000) Sulfated glycoconjugates enhance CD36-dependent adhesion of Plasmodium falciparum-infected erythrocytes to human microvascular endothelial cells. Blood, 96, 327-333.
67. McNeely, W.H. (1959) Fucoidan. In Whistler, R.L. (ed), Industrial gums. Academic Press, New York, pp. 117-125.
68. Medcalf, D.G., Schneider, T.L., and Barnett, R.W. (1978) Structural features of a novel glucuronogalactofucan from Ascophyllum nodosum. Carbohyd. Res., 66, 167-171.
69. Mengerink, K.J., Moy, G.W., and Vacquier, V.D. (2002) suREJ3, a polycystin-1 protein, is cleaved at the GPS domain and localizes to the acrosomal region of sea urchin sperm. J. Biol. Chem., 277, 943-948.
70. Mian, A.J. and Percival, E. (1973) Carbohydrates of the brown seaweeds Himanthalia lorea, Bifurcaria bifurcata, and Padina pavonia. Carbohyd. Res., 26, 133-146.
71. Millet, J., Jouault, S.C., Mauray, S., Theveniaux, J., Sternberg, C., Boisson, V.C., and Fischer, A.M. (1999) Antithrombotic and anti-coagulant activities of a low molecular weight fucoidan by the subcutaneous route. Thromb. Haemost., 81, 391-395.
72. Moreno, R., Orihuela, P., and Barros, C. (2001) Differential effects of polysulphates between mouse and hamster during in vitro fertilization. Andrologia, 33, 19-25.
73. Mori, H., Kamei, H., Nishide, E., and Nisizawa, K. (1982) Sugar constituents of some sulfated polysaccharides from the sporophylls of wakame (Undaria pinnatifida) and their biological activities. In Marine algae in pharmaceutical science. Walter de Gruyter, Berlin and New York, pp. 109-121.
74. Morinaga, T., Araki, T., Ito, M., and Kitamikado, M. (1981) A search for fucoidan-degrading bacteria in coastal sea environments of Japan. Bull. Japan. Soc. Sci. Fish., 47, 621-625.
75. Mourão, P.A.S. and Bastos, I.G. (1987) Highly acidic glycans from sea cucumbers. Eur. J. Biochem., 166, 639-645.
76. Mourão, P.A.S. and Pereira, M.S. (1999) Searching for alternatives to heparin: sulfated fucans from marine invertebrates. Trends Cardiovasc. Med., 9, 225-232.
77. Mulloy, B., Ribeiro, A.C., Alves, A.P., Vieira, R.P., and Mourao, P.A.S. (1994) Sulfated fucans from echinoderms have a regular tetrasaccharide repeating unit defined by specific patterns of sulfation at the O-2 and O-4 positions. J. Biol. Chem., 269, 22113-22123.
78. Nagaoka, M., Shibata, H., Kimura-Takagi, I., Hashimoto, S., Kimura, K., Makino, T., Aiyama, R., Ueyama, S., and Yokokura, T. (1999) Structural study of fucoidan from Cladosiphon okamuranus Tokida. Glycoconj. J., 16, 19-26.
79. Nasu, T., Fukuda, Y., Nagahira, K., Kawashima, H., Noguchi, C., and Nakanishi, T. (1997) Fucoidin, a potent inhibitor of L-selectin function, reduces contact hypersensitivity reaction in mice. Immunol. Lett., 59, 47-51.
80. Nishino, T. and Nagumo, T. (1991) Structural characterization of a new anticoagulant fucan sulfate from the brown seaweed Ecklonia kurome. Carbohyd. Res., 211, 77-90.
81. Nishino, T., Nishioka, C., Ura, H., and Nagumo, T. (1994) Isolation and partial characterization of a novel amino sugar-containing fucan sulfate from commercial Fucus vesiculosus fucoidan. Carbohydr. Res., 255, 213-224.
82. Nishino, T., Fukuda, A., Nagumo T., Fujihara, M., and Kaji, E. (1999) Inhibition of the generation of thrombin and factor Xa by a fucoidan from the brown seaweed Ecklonia kurome. Thromb. Res., 96, 37-49.
83. Nishino, T., Yamauchi, T., Horie, M., Nagumo, T., and Suzuki, H. (2000) Effects of a fucoidan on the activation of plasminogen by u-PA and t-PA. Thromb. Res., 99, 623-634.
84. Omata, M., Matsui, N., Inomata, N., and Ohno, T. (1997) Protective effects of polysaccharide fucoidin on myocardial ischemia-reperfusion injury in rats. J. Cardiovasc. Pharmacol., 30, 717-724.
85. O'Neill, A.N. (1954) Degradative studies on fucoidin. J. Am. Chem. Soc., 76, 5074-5076.
86. Ortega-Barria, E. and Boothroyd, J.C. (1999) A Toxoplasma lectin-like activity specific for sulfated polysaccharides is involved in host cell infection. J. Biol. Chem., 274, 1267-1276.
87. Ostergaard, C., Yieng-Kow, R.V., Benfield, T., Frimodt-Moller, N., Espersen, F., and Lundgren, J.D. (2000) Inhibition of leukocyte entry into the brain by the selectin blocker fucoidin decreases interleukin-1 (IL-1) levels but increases IL-8 levels in cerebrospinal fluid during experimental Pneumococcal meningitis in rabbits. Infect. Immun., 68, 3153-3157.
88. Patankar, M.S., Oehninger, S., Barnett, T., Williams, R.L., and Clark, G.F. (1993) A revised structure for fucoidan may explain some of its biological activities. J. Biol. Chem., 268, 21770-21776.
89. Patel, M.K., Mulloy, B., Gallagher, K.L., O'Brien, L., and Hughes, A.D. (2002) The antimitogenic action of the sulphated polysaccharide fucoidan differs from heparin in human vascular smooth muscle cells. Thromb. Haemost., 87, 149-154.
90. Percival, E. (1968) Glucuronoxylofucan, a cell-wall component of Ascophyllum nodosum. Carbohyd. Res., 7, 272-283.
91. Percival, E.G.V. and Ross, A.G. (1950) The isolation and purification of fucoidin from brown seaweeds. J. Chem. Soc., 717-720.
92. Pereira, M.S., Mulloy, B., and Mourao, P.A.S. (1999) Structure and anticoagulant activity of sulfated fucans. J. Biol. Chem., 274, 7656-7667.
93. Pereira, M.S., Melo, F.R., and Mourão, P.A.S. (2002) Is there a correlation between structure and anticoagulant action of sulfated galactans and sulfated fucans? Glycobiology, 12, 573-580.
94. Ponce, N.M.A., Pujol, C.A., Damonte, E.B., Flores, M.L., and Stortz, C.A. (2003) Fucoidans from the brown seaweed Adenocystis utricularis: extraction methods, antiviral activity and structural studies. Carbohydr. Res., 338, 153-165.
95. Preeprame, S., Hayashi, K., Lee, J.B., Sankawa, U., and Hayashi, T. (2001) A novel antivirally active fucan sulfate derived from an edible brown alga, Sargassum horneri. Chem. Pharm. Bull., 49, 484-485.
96. Ribeiro, A.C., Vieira, R.P., Mourao, P.A.S., and Mulloy, B. (1994) A sulfated α-L-fucan from sea cucumber. Carbohyd. Res., 255, 225-240.
97. Ritter, L.S., Copeland, J.G., and McDonagh, P.F. (1998) Fucoidin reduces coronary microvascular leukocyte accumulation early in reperfusion. Ann. Thorac. Surg., 66, 2063-2072.
98. Rogerson, S.J., Chaiyaroj, S.C., Ng, K., Reeder, J.C., and Brown, G.V. (1995) Chondroitin sulfate A is a cell surface receptor for Plasmodium falciparum-infected erythrocytes. J. Exp. Med., 182, 15-20.
99. Rozkin, M.Y., Levina, M.N., Kameneva, N.S., Usov, A.I., and Yefimov, V.S. (1989) Investigation of the mechanism of the anti-coagulant action of fucoidans. Farmakol. i toksik., 3, 48-51.
100. Schweiger, R.G. (1962) Methanolysis of fucoidan. I. Preparation of methyl α-L-fucoside and L-fucose. J. Org. Chem., 27, 4267-4272.
101. Shimaoka, M., Ikeda, M., Iida, T., Taenaka, N., Yoshiya, I., and Honda, T. (1996) Fucoidin, a potent inhibitor of leukocyte rolling, prevents neutrophil influx into phorbol-ester-induced inflammatory sites in rabbit lungs. Am. J. Respir. Crit. Care. Med., 153, 307-311.
102. Sweeney, E.A., Priestley, G.V., Nakamoto, B., Collins, R.G., Beaudet, A.L., and Papayannopoulou, T. (2000) Mobilization of stem/progenitor cells by sulfated polysaccharides does not require selectin presence. Proc. Natl Acad. Sci. USA, 97, 6544-6549.
103. Sweeney, E.A., Lortat-Jacob, H., Priestley, G.V., Nakamoto, B., and Papayannopoulou, T. (2002) Sulfated polysaccharides increase plasma levels of SDF-1 in monkeys and mice: involvement in mobilization of stem/progenitor cells. Blood, 99, 44-51.
104. Talevi, R. and Gualtieri, R. (2001) Sulfated glycoconjugates are powerful modulators of bovine sperm adhesion and release from the oviductal epithelium in vitro. Biol. Reprod., 64, 491-498.
105. Tanaka, K. and Sorai, S. (1970) Hydrolysis of fucoidan by abalone liver α-L-fucosidase. FEBS Lett., 9, 45-48.
106. Teixeira, M.M. and Hellewell, P. (1997) The effect of the selectin binding polysaccharide fucoidin on eosinophil recruitment in vivo. Brit. J. Pharmacol, 120, 1059-1066.
107. Thanassi, N.M. and Nakada, H. (1967) Enzymic degradation of fucoidan by enzymes from the hepatopancreas of abalone, Haliotus species. Arch. Biochem. Biophys., 118, 172-177.
108. Thorlacius, H., Vollmar, B., Seyfert, U.T., Vestweber, D., and Menger, M.D. (2000) The polysaccharide fucoidan inhibits microvascular thrombus formation independently from P- and L-selectin function in vivo. Eur. J. Clin. Invest., 30, 804-810.
109. Trento, F., Cattaneo, F., Pescador, R., Porta, R., and Ferro, L. (2001) Antithrombin activity of an algal polysaccharide. Thromb. Res., 102, 457-465.
110. Usov, A.I., Smirnova, G.P. and Klochkova, N.G. (2001) Algae polysaccharides. 55. Polysaccharide composition of some brown Kamchatka algae. Bioorg. Khim., 27, 444-448.
111. Usui, T., Asari, K., and Mizuno, T. (1980) Isolation of highly purified "fucoidan" from Eisenia bicyclis and its anticoagulant and antitumor activities. Agric. Biol. Chem., 44, 1965-1966.
112. Vacquier, V.D. and Moy, G.W. (1997) The fucose sulfate polymer of egg jelly binds to sperm REJ and is the inducer of the sea urchin sperm acrosome reaction. Dev. Biol., 192, 125-135.
113. Vasseur, E. (1948) Chemical studies on the jelly coat of the sea-urchin egg. Acta Chem. Scand., 2, 900-913.
114. Verdrengh, M., Erlandsson-Harris, H., and Tarkowski, A. (2000) Role of selectins in experimental Staphylococcus aureus-induced arthritis. Eur. J. Immunol., 30, 1606-1613.
115. Vilela-Silva, A.C., Alves, A.P., and Valente, A.P. (1999) Structure of the sulfated α-L-fucan from the egg jelly coat of the sea urchin Strongylocentrotus franciscanus: patterns of preferential 2-O- and 4-O-sulfation determine sperm cell recognition. Glycobiology, 9, 927-933.
116. Vilela-Silva, A.C., Castro, M.O., Valente, A.P., Biermann, C.H., and Mourao, P.A.S. (2002) Sulfated fucans from the egg jellies of the closely related sea urchins Strongylocentrotus droebachiensis and Strongylocentrotus pallidus ensure species-specific fertilization. J. Biol. Chem., 277, 379-387.
117. Von Holdt, M.M., Ligthelm, S.P., and Nunn, J.R. (1955) South African seaweeds: seasonal variations in the chemical composition of some phaeophyceae. J. Sci. Food Agr., 6, 193-197.
118. Wort, D.J. (1955) The seasonal variation in chemical composition of Macrocystis integrifolia and Neroecystis luetkeana in British Colombia coastal waters. Can. J. Bot., 33, 323-340.
119. Yamamoto, K., Tsuji, Y., Kumagai, H., and Tochikura, T. (1986) Induction and purification of α-L-fucosidase from Fusarium oxysporum. Agric. Biol. Chem., 50, 1689-1695.
120. Yaphe, W. and Morgan, K. (1959) Hydrolysis of fucoidin by Pseudomonas atlantica and Pseudomonas carrageenovora. Nature, 463, 761-762.
121. Ying, P., Shakibaei, M., Patankar, M.S., Clavijo, P., Beavis, R.C., Clark, G.F., and Frevert, U. (1997) The malaria circumsporozoite protein: interaction of the conserved regions I and II-plus with heparin-like oligosaccharides in heparan sulfate. Exp. Parasitol., 85, 168-182.