Abstract:
The brown seaweed Sargassum stenophyllum biosynthesizes two different sets of fucoidans. One of them is characterized by higher percentages of glucuronic acid and fewer sulfate groups, which are situated on different sugar units. α-L-Fucose was the major component but other sugars like β-D-galactose, β-D-mannose, α-D-glucuronic acid, α-D-glucose and β-D-xylose were also in substantial amounts. Fucoidans from the other set contain small amounts of α-D-glucuronic acid and high percentages of sulfate groups, which are concentrated on the fucose residues, with only fucose and galactose as major components. Structural studies of one fucoidan from each set suggest that these products have a general basic structure that has a formal resemblance to that of the fucosylated chondroitin sulfates from the body wall of sea cucumbers, namely, a linear core (formed mainly by (1→6)-β-D-galactose and/or (1→2)-β-D-mannose units) with branched chains of 'fucans' (formed by (1→3) and/or (1→4)-α-L-fucose, (1→4)-α-D-glucuronic acid, terminal β-D-xylose and, sometimes, (1→4)-α-D-glucose). In fucoidans from the second set, the 'core' is reduced to short galactan chains. © 2001 Elsevier Science Ltd. All rights reserved.
Registro:
Documento: |
Artículo
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Título: | Structural studies on fucoidans from the brown seaweed Sargassum stenophyllum |
Autor: | Duarte, M.E.R.; Cardoso, M.A.; Noseda, M.D.; Cerezo, A.S. |
Filiación: | Departamento De Bioquímica, Universidade Federal Do Paraná, PO Box 19046, CEP 81531-990 Curitiba, Parana, Brazil Departamento De Química Orgánica, CIHIDECAR-CONICET, Ciudad Universitaria, 1428 Buenos Aires, Argentina
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Palabras clave: | Brown seaweed; Chemical structure; Fucans; Fucoidans; Sargassum stenophyllum; Sulfated heteropolysaccharides; Organic acids; Polysaccharides; Sugars; Fucoidans; Carbohydrates; alpha glucose; alpha glucuronic acid; alpha levo fucose; beta galactose; beta xylose; chondroitin sulfate; fucoidin; fucose; galactose; glucose; glucuronic acid; mannose; sulfur derivative; unclassified drug; xylose; article; biosynthesis; drug structure; echinoderm; fucosylation; nonhuman; priority journal; seaweed; structure analysis; Anticoagulants; Blood Coagulation; Humans; Monosaccharides; Nuclear Magnetic Resonance, Biomolecular; Optical Rotation; Partial Thromboplastin Time; Polysaccharides; Seaweed; Thrombin Time; algae; Cucumis sativus; Holothuroidea; Sargassum stenophyllum |
Año: | 2001
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Volumen: | 333
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Número: | 4
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Página de inicio: | 281
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Página de fin: | 293
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DOI: |
http://dx.doi.org/10.1016/S0008-6215(01)00149-5 |
Título revista: | Carbohydrate Research
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Título revista abreviado: | Carbohydr. Res.
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ISSN: | 00086215
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CODEN: | CRBRA
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CAS: | Anticoagulants; fucoidan, 9072-19-9; Monosaccharides; Polysaccharides
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Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v333_n4_p281_Duarte |
Referencias:
- Patankar, M.S., Oehninger, S., Barnett, T., Williams, R.L., Clark, G.F., (1993) J. Biol. Chem., 268, pp. 21770-21776
- Nishino, T., Takabe, Y., Nagumo, T., (1994) Carbohydr. Polym., 23, pp. 165-173
- Shalgi, R., Matityahu, A., Nebel, L., (1986) Biol. Reprod., 34, pp. 446-452
- Oehninger, S., Clark, G.F., Acosta, A.A., Hodgen, G.D., (1991) Fertil. Steril., 55, pp. 165-169
- Baba, M., Snoeck, R., Pauwels, R., DeClercq, E., (1988) Antimicrob. Agents Chemother., 32, pp. 1742-1745
- Clark, G.F., Oehninger, S.C., Moen, L.K., (1992) FASEB J., 6, pp. A233
- Foxall, C., Watson, S.R., Dowbenko, D., Lasky, L.A., Kiso, M., Hasegawa, A., Asa, D., Brandley, B.K., (1992) J. Cell Biol., 117, pp. 895-902
- Nishino, T., Nagumo, T., (1992) Carbohydr. Res., 229, pp. 355-362
- Dubois, M., Gilles, K.A., Hamilton, J.K., Rebers, P.A., Smith, F., (1956) Anal. Chem., 28, pp. 350-356
- Blumenkrantz, N., Asboe-Hansen, G., (1973) Anal. Biochem., 54, pp. 484-489
- Dodgson, K.S., Price, R.G., (1962) Biochem. J., 84, pp. 106-110
- Lowry, O.H., Rosebrough, N.J., Farr, A.L., Randall, R.J., (1951) J. Biol. Chem., 193, pp. 265-275
- Matulewicz, M.C., Cerezo, A.S., (1987) Carbohydr. Polym., 7, pp. 121-132
- Nagasawa, K., Inoue, Y., Kamaia, T., (1977) Carbohydr. Res., 58, pp. 47-55
- Taylor, R.L., Conrad, H.E., (1972) Biochemistry, 11, pp. 1383-1388
- Stone, B.A., Anderson, M.A., (1985) Carbohydr. Polym., 5, pp. 115-120
- Stortz, C.A., Cerezo, A.S., (1993) Carbohydr. Res., 242, pp. 217-227
- Ciucanu, I., Kerek, F., (1984) Carbohydr. Res., 131, pp. 209-217
- Andersson, L.O., Barowcliffe, T.W., Holmer, E., Johnson, E.A., Söder-Ström, G., (1979) Thromb. Res., 15, pp. 531-541
- Carlucci, M.J., Pujol, C.A., Ciancia, M., Noseda, M.D., Matulewicz, M.C., Damonte, E.B., Cerezo, A.S., (1997) Int. J. Biol. Macromol., 20, pp. 97-105
- Tortorella, H., Mazzini, M.N., Cerezo, A.S., (1988) Anal. Lett., 21, pp. 2195-2204
- Orr, S.F.D., (1954) Biochem. Biophys. Acta, 14, pp. 173-181
- Percival, E., Young, M., (1974) Carbohydr. Res., 32, pp. 195-201
- Percival, E., (1968) Carbohydr. Res., 7, pp. 272-283
- Mian, A.J., Percival, E., (1973) Carbohydr. Res., 26, pp. 147-161
- Larsen, B., Haug, A., Painter, T.L., (1966) Acta Chem. Scand., 20, pp. 219-230
- Abdel-Fattah, A.F., Hussein, M.M.-D., Salem, H.M., (1974) Carbohydr. Res., 33, pp. 9-17
- Abdel-Fattah, A.F., Hussein, M.M.-D., Salem, H.M., (1974) Carbohydr. Res., 33, pp. 19-24
- Nishino, T., Nagumo, T., Kiyohara, H., Yamada, H., (1991) Carbohydr. Res., 211, pp. 77-90
- Nishino, T., Yokoyama, G., Dobashi, K., Fujihara, M., Nagumo, T., (1989) Carbohydr. Res., 186, pp. 119-129
- Nishino, T., Kiyohara, H., Yamada, H., Nagumo, T., (1991) Phytochemistry, 30, pp. 535-539
- Nishino, T., Nishioka, C., Ura, H., Nagumo, T., (1994) Carbohydr. Res., 255, pp. 213-224
- Duarte, M.E.R., (1990) Heteropolissacarídeos ácidos isolados de Laminaria brasiliensis J. & O.: ácido algínico e fucanas, , Ph.D. Thesis, Federal University of Paraná, Curitiba, Brazil
- Chevolot, L., Foucault, A., Chaubet, F., Kervarec, N., Sinquin, C., Fisher, A.-M., Boisson-Vidal, C., (1999) Carbohydr. Res., 319, pp. 154-165
- Schweiger, R.G., (1962) J. Org. Chem., 27, pp. 4270-4272
- Bouveng, H., Lindberg, B., (1955) Acta Chem. Scand., 9, pp. 168-169
- Magdel-Din Hussein, M., (1975) Phytochemistry, 14, pp. 1866-1868
- Medcalf, D.G., Schneider, T.L., Barnett, R.W., (1978) Carbohydr. Res., 66, pp. 167-171
- Nagaoka, M., Shibata, H., Kimura-Takagi, I., Hashimoto, S., Kimura, K., Makino, T., Aiyama, R., Yokokura, T., (1999) Glycoconjugate J., 16, pp. 19-26
- Mulloy, B., Ribeiro, A.C., Alves, A.P., Vieiras, R.P., Mourão, P.A.S., (1994) J. Biol. Chem., 269, pp. 22113-22123
- Chizhov, A.O., Dell, A., Morris, H.R., Haslam, S.M., McDowell, R.A., Shashkov, A.S., Nifant'ev, N.E., Usov, A.I., (1999) Carbohydr. Res., 320, pp. 108-119
- Zhuang, C., Itoh, H., Mizuno, T., Ito, H., (1993) Bull. Fac. Agric. Shizuoka Univ., 43, pp. 61-70
- (1994) Chem. Abstr., 121, p. 129503
- Maruyama, T., Toshihiko, T., Imanari, T., Yu, G., Linhardt, R., (1998) J. Carbohydr.Res., 306, pp. 35-43
- Usov, A.I., Smirnova, G.P., Bilan, M.I., Shashkov, A.S., (1998) Russ. J. Bioorg. Chem., 24, pp. 437-445
- Mourão, P.A.S., Pereira, M.S., Pavão, M.S.G., Mulloy, B., Tollefsen, D.M., Mowinckel, M.-C., Abildgaard, U., (1996) J. Biol.Chem., 271, pp. 23973-23984
- Kariya, Y., Watabe, S., Hashimoto, K., Yoshida, K., (1990) J. Biol. Chem., 265, pp. 5081-5085
- Kariya, Y., Watabe, S., Kyogashima, M., Ishihara, M., Ishii, T., (1997) Carbohydr. Res., 297, pp. 273-279
- Vieira, R.P., Mulloy, B., Mourão, P.A.S., (1991) J. Biol. Chem., 266, pp. 13530-13536
Citas:
---------- APA ----------
Duarte, M.E.R., Cardoso, M.A., Noseda, M.D. & Cerezo, A.S.
(2001)
. Structural studies on fucoidans from the brown seaweed Sargassum stenophyllum. Carbohydrate Research, 333(4), 281-293.
http://dx.doi.org/10.1016/S0008-6215(01)00149-5---------- CHICAGO ----------
Duarte, M.E.R., Cardoso, M.A., Noseda, M.D., Cerezo, A.S.
"Structural studies on fucoidans from the brown seaweed Sargassum stenophyllum"
. Carbohydrate Research 333, no. 4
(2001) : 281-293.
http://dx.doi.org/10.1016/S0008-6215(01)00149-5---------- MLA ----------
Duarte, M.E.R., Cardoso, M.A., Noseda, M.D., Cerezo, A.S.
"Structural studies on fucoidans from the brown seaweed Sargassum stenophyllum"
. Carbohydrate Research, vol. 333, no. 4, 2001, pp. 281-293.
http://dx.doi.org/10.1016/S0008-6215(01)00149-5---------- VANCOUVER ----------
Duarte, M.E.R., Cardoso, M.A., Noseda, M.D., Cerezo, A.S. Structural studies on fucoidans from the brown seaweed Sargassum stenophyllum. Carbohydr. Res. 2001;333(4):281-293.
http://dx.doi.org/10.1016/S0008-6215(01)00149-5