Abstract:
The water-soluble sulfated xylogalactoarabinans from green seaweed Cladophora falklandica are constituted by a backbone of 4-linked β-L-arabinopyranose units partially sulfated mainly on C3 and also on C2. Besides, partial glycosylation mostly on C2 with single stubs of β-D-xylopyranose, or single stubs of β-D-galactofuranose or short chains comprising (1 → 5)- and/or (1 → 6)-linkages, was also found. These compounds showed anticoagulant activity, although much lower than that of heparin. The effect of a purified fraction (F1) on the fibrin network was studied in detail. It modifies the kinetics of fibrin formation, suggesting an impaired polymerization process. Scanning electron microscopy showed a laxer conformation, with larger interstitial pores than the control. Accordingly, this network was lysed more easily. These fibrin properties would reduce the time of permanence of the clot in the blood vessel, inducing a lesser thrombogenic state. One of the possible mechanisms of its anticoagulant effect is direct thrombin inhibition. © 2016 Elsevier Ltd
Registro:
Documento: |
Artículo
|
Título: | Novel sulfated xylogalactoarabinans from green seaweed Cladophora falklandica: Chemical structure and action on the fibrin network |
Autor: | Arata, P.X.; Quintana, I.; Raffo, M.P.; Ciancia, M. |
Filiación: | Universidad de Buenos Aires, Facultad de Agronomía, Departamento de Biología Aplicada y Alimentos, Cátedra de Química de Biomoléculas, Av. San Martín 4453Buenos Aires C1417DSE, Argentina Universidad de Buenos Aires, Facultad de Ciencias Exactas y Naturales, Departamento de Química Biológica, Laboratorio de Hemostasia y Trombosis, Ciudad Universitaria – Pabellón 2Buenos Aires C1428EHA, Argentina Consejo Nacional de lnvestigaciones Cientificas y Tecnicas-Centro Nacional Patagónico (CENPAT-CONICET), Bvd. Brown 2915, Puerto Madryn, Chubut U9120ACD, Argentina Universidad de Buenos Aires, Facultad de Ciencias Exactas y Naturales, Departamento de Química Orgánica, Consejo Nacional de lnvestigaciones Cientificas y Tecnicas-Centro de Investigación de Hidratos de Carbono (CIHIDECAR-CONICET), Ciudad Universitaria – Pabellón 2Buenos Aires C1428EHA, Argentina
|
Palabras clave: | Anticoagulant activity; Cladophora; Fibrin network; Galactofuranose; Green seaweed; Sulfated arabinan; Blood vessels; Scanning electron microscopy; Anticoagulant activities; Arabinans; Cladophora; Fibrin network; Galactofuranose; Green seaweed; Seaweed; anticoagulant agent; fibrin; polysaccharide; sulfate; xylopyranose; xylose; analogs and derivatives; animal; chemistry; conformation; drug effects; fibrinolysis; green alga; human; Leporidae; metabolism; preclinical study; procedures; scanning electron microscopy; seaweed; Animals; Anticoagulants; Carbohydrate Conformation; Chlorophyta; Drug Evaluation, Preclinical; Fibrin; Fibrinolysis; Humans; Microscopy, Electron, Scanning; Polysaccharides; Rabbits; Seaweed; Sulfates; Xylose |
Año: | 2016
|
Volumen: | 154
|
Página de inicio: | 139
|
Página de fin: | 150
|
DOI: |
http://dx.doi.org/10.1016/j.carbpol.2016.07.088 |
Título revista: | Carbohydrate Polymers
|
Título revista abreviado: | Carbohydr Polym
|
ISSN: | 01448617
|
CODEN: | CAPOD
|
CAS: | fibrin, 9001-31-4; sulfate, 14808-79-8; xylose, 25990-60-7, 58-86-6; Anticoagulants; Fibrin; Polysaccharides; Sulfates; xylopyranose; Xylose
|
Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_01448617_v154_n_p139_Arata |
Referencias:
- Anand, S., Yusuf, S., Pogue, J., Ginsberg, J., Hirsh, J., Relationship of activated partial thromboplastin time to coronary events and bleeding in patients with acute coronary syndromes who receive heparin (2003) Circulation, 107, pp. 2884-2888
- Angell, A.R., Mata, L., de Nys, R., Paul, N.A., The protein content of seaweeds: A universal nitrogen-to-protein conversion factor of five (2016) Journal of Applied Phycollogy, 28, pp. 511-524
- Arata, P.X., Quintana, I., Canelón, D.J., Vera, B.E., Compagnone, R.S., Ciancia, M., Chemical structure and anticoagulant activity of highly pyruvylated sulfated galactans from tropical green seaweeds of the order Bryopsidales (2015) Carbohydrate Polymers, 122, pp. 376-386
- Bilan, M.I., Vinogradova, E.V., Shashkov, A.S., Usov, A.I., Structure of a highly pyruvylated galactan sulfate from the pacific green alga Codium yezoense (Bryopsidales, Chlorophyta) (2007) Carbohydrate Research, 342, pp. 586-596
- Bock, K., Pedersen, C., Carbon-13 nuclear magnetic resonance spectroscopy of monosaccharides (1982) Advances in Carbohydrate Chemistry and Biochemistry, 41, pp. 27-66
- Bradford, M.M., A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein dye binding (1976) Analytical Biochemistry, 72, pp. 248-254
- Cardoso, M.A., Noseda, M.D., Fujii, M.T., Zibetti, R.G., Duarte, M.E., Sulfated xylomannans isolated from red seaweeds Chondrophycus papillosus and C. flagelliferus (Ceramiales) from Brazil (2007) Carbohydrate Research, 342, pp. 2766-2775
- Carr, M.E., Alving, B.M., Effect of fibrin structure on plasmin-mediated dissolution of plasma clots (1995) Blood Coagulation and Fibrinolysis, 6, pp. 567-573
- Cases, M.R., Cerezo, A.S., Stortz, C.A., Separation and quantitation of enantiomeric galactoses and their mono-O-methylethers as their diastereomeric acetylated 1-deoxy-1-(2-hydroxypropylamino) alditols (1995) Carbohydrate Research, 269, pp. 333-341
- Cassolato, J.E.F., Noseda, M.D., Pujol, C.A., Pellizzari, F.M., Damonte, E.B., Duarte, M.A.R., Chemical structure and antiviral activity of the sulfated heterorhamnan isolated from the green seaweed Gayralia oxysperma (2008) Carbohydrate Research, 343, pp. 3085-3095
- Chattopadhyay, K., Adhikari, U., Lerouge, P., Ray, B., Polysaccharides from Caulerpa racemosa. Purification and structural features (2007) Carbohydrate Polymers, 68, pp. 407-415
- Ciancia, M., Matulewicz, M.C., Finch, P., Cerezo, A.S., Determination of the structures of cystocarpic carrageenans from Gigurtina skottsbergii by methylation analysis and NMR spectroscopy (1993) Carbohydrate Research, 238, pp. 241-248
- Ciancia, M., Quintana, I., Vizcargüénaga, M.I., Kasulin, L., de Dios, A., Estevez, J.M., Polysaccharides from the green seaweeds Codium fragile and C. vermilara with controversial effects on hemostasis (2007) International Journal of Biological Macromolecules, 41, pp. 641-649
- Ciancia, M., Quintana, I., Cerezo, A.S., Overview of anticoagulant activity of sulfated polysaccharides from seaweeds in relation to their structures, focusing on those of green seaweeds (2010) Current Medicinal Chemistry, 17, pp. 2503-2529
- Ciucanu, I., Kerek, K., A simple and rapid method for the permethylation of carbohydrates (1984) Carbohydrate Research, 134, pp. 209-217
- Collet, J.P., Park, D., Lesty, C., Soria, J., Soria, C., Montalescot, G., Influence of fibrin network conformation and fibrin fiber diameter on fibrinolysis speed: Dynamic and structural approaches by confocal microscopy (2000) Arteriosclerosis Thrombosis and Vascular Biology, 20, pp. 1354-1361
- Collet, J.P., Lesty, C., Montalescot, G., Weisel, J.W., Dynamic changes of fibrin architecture during fibrin formation and intrinsic fibrinolysis of fibrin-rich clots (2003) Journal of Biological Chemistry, 278, pp. 21331-21335
- Cordeiro, L.M.C., Carbonero, E.R., Sassaki, G.L., Reis, R.A., Stocker-Wörgötter, E., Gorin, P.A.J., A fungus-type β-galactofuranan in the cultivated Trebouxia photobiont of the lichen Ramalina gracilis (2005) FEMS Microbiology Letters, 244, pp. 193-198
- Cordeiro, L.M.C., Beilke, F., Bettim, F.L., Reinhardt, V.F., Rattmann, Y.D., Iacomini, M., (1 → 2) and (1 → 6)-linked β-D-galactofuranan of microalga Myrmecia biatorellae: Symbiotic partner of Lobaria linita (2012) Carbohydrate Polymers, 90, pp. 1779-1785
- Cordeiro, L.M.C., Beilke, F., Reinhardt, V.F., Sassaki, G.L., Iacomini, M., Rhamnogalactofuranan from the microalga Myrmecia biatorellae: Symbiotic partner of Lobaria linita (2013) Phytochemistry, 94, pp. 254-259
- Dodgson, K.S., Price, R.G., A note on the determination of the ester sulphate content of sulphated polysaccharides (1962) Biochemistry Journal, 84, pp. 106-110
- Dubois, M., Gilles, K.A., Hamilton, J.K., Rebers, P.A., Smith, F., Colorimetric method of determination of sugars and related substances (1956) Analytical Chemistry, 28, pp. 350-356
- Fernández, P.V., Quintana, I., Cerezo, A.S., Caramelo, J.J., Pol-Fachin, L., Verli, H., Anticoagulant activity of a unique sulphated pyranosic (1(3)-β-L-arabinan through direct interaction with thrombin (2013) Journal of Biological Chemistry, 288, pp. 223-233
- Fernández, P.V., Raffo, M.P., Alberghina, J., Ciancia, M., Polysaccharides from the green seaweed Codium decorticatum: Structure and cell wall distribution (2015) Carbohydrate Polymers, 117, pp. 836-844
- Filisetti-Cozzi, T.M., Carpita, N.C., Measurement of uronic acids without interference from neutral sugars (1991) Analytical Biochemistry, 197, pp. 157-162
- Kelton, J.G., Hirsh, J., Bleeding associated with antithrombotic therapy (1980) Seminars Hematology, 17, pp. 259-291
- Kelton, J.G., Warkentin, T.E., Heparin-induced thrombocytopenia: A historical perspective (2008) Blood, 112, pp. 2607-2616
- Koepsell, H.J., Sharpe, E.S., Microdetermination of pyruvic and α-ketoglutaric acids (1952) Archives of Biochemistry and Biophysics, 38, pp. 443-449
- Kolev, K., Machovich, R., Molecular and cellular modulation of fibrinolysis (2003) Thrombosis and Haemostasis, 89, pp. 610-621
- Laffan, M.A., Bradshaw, A.E., Investigation of haemostasis. Practical haematology (1995), pp. 297-315. , J.V. Dacie S.M. Lewis Churchill Livingstone New York; Li, H., Mao, W., Zhang, X., Qi, X., Chen, Y., Chen, Y., Structural characterization of an anticoagulant-active sulfated polysaccharide isolated from green alga Monostroma latissimum (2011) Carbohydrate Polymers, 85, pp. 394-400
- Lowry, O.H., Rosenbrough, N.J., Farr, A.L., Protein measurements with the Folin phenol reagent (1951) Journal of Biological Chemistry, 193, pp. 265-275
- Meh, D.A., Mosesson, M.W., DiOrio, J.P., Siebenlist, K.R., Hernandez, I., Amrani, D.L., Disintegration and reorganization of fibrin networks during tissue-type plasminogen activator-induced clot lysis (2001) Blood Coagulation Fibrinolysis, 12, pp. 627-637
- Morrison, I.M., Hydrolysis of plant cell walls with trifluoroacetic acid (1988) Phytochemistry, 27, pp. 1097-1100
- Mourão, P.A.S., Perspective on the use of sulfated polysaccharides from marine organisms as a source of new antithrombotic drugs (2015) Marine Drugs, 13 (5), pp. 2770-2784
- Navarro, D.A., Flores, M.L., Stortz, C.A., Microwave-assisted desulfation of sulfated polysaccharides (2007) Carbohydrate Polymers, 69, pp. 742-747
- Park, J.T., Johnson, M.J., A submicrodetermination of glucose (1949) Journal of Biological Chemistry, 181, pp. 149-151
- Percival, E., McDowell, R.H., Algal walls: Composition and biosynthesis (1981) Encyclopedia of plant physiology, 13B, pp. 277-316. , W. Tanner F.A. Loewus Springer Berlin
- Petersen, B.O., Meier, S., Smestad Paulsen, B., Redondo, A.R., Skovsted, I.C., Determination of native capsular polysaccharide structures of Streptococcus pneumoniae serotypes 39, 42, and 47F and comparison to genetically or serologically related strains (2014) Carbohydrate Research, 395, pp. 38-46
- Prieto, A., Leal, J.A., Poveda, A., Jiménez-Barbero, J., Gómez-Miranda, B., Domenech, J., Structure of complex cell wall polysaccharides isolated from Trichoderma and Hypocrea species (1997) Carbohydrate Research, 304, pp. 281-291
- Prieto, A., Leal, J.A., Gómez-Miranda, B., Ahrazem, O., Jiménez-Barbero, J., Bernabé, M., Structure of a cell wall polysaccharide isolated from Hypocrea gelatinosa (2001) Carbohydrate Research, 333, pp. 173-178
- Quick, J., The prothrombin time in haemophilia and in obstructive jaundice (1935) Journal of Biological Chemistry, 109, pp. 73-74
- Ruiz Contreras, R., Kamerling, J.P., Breg, J., Vliegenthart, F.G., 1H- and 13C-n.m.r. spectroscopy of synthetic monosulphated methyl α-D-galactopyranosides (1988) Carbohydrate Research, 179, pp. 411-418
- Sri Ramana, K., Venkata Rao, E., Structural features of the sulphated polysaccharide from a green seaweed, Cladophora socialis (1991) Phytochemistry, 30, pp. 259-262
- Stevenson, T.T., Furneaux, R.H., Chemical methods for the analysis of sulphated galactans from red algae (1991) Carbohydrate Research, 210, pp. 277-298
- Stortz, C.A., Cerezo, A.S., Conformational analysis of sulfated α-(1 → 3)-linked D-galactobioses using the MM3 force-field (1998) Journal of Carbohydrate Chemistry, 17, pp. 1405-1419
- Usov, A.I., Elashvili, M.Y., Polysaccharides of algae 44. Investigation of sulfated galactan from Laurencia nipponica Yamada (Rhodophyta, Rhodomelaceae) using partial reductive hydrolysis (1991) Botanica Marina, 34, pp. 553-560
- Usov, A.I., Yarotsky, S.V., Shashkov, A.S., 13C nmr spectroscopy of red algal galactans (1980) Biopolymers, 19, pp. 977-990
- Weisel, J.W., Structure of fibrin: Impact on clot stability (2007) Journal of Thrombosis and Haemostasis, 5, pp. 116-124
- Wissel, H., Mayr, C., Lücke, A., A new approach for the isolation of cellulose from aquatic plant tissue and freshwater sediments for stable isotope analysis (2008) Organic Geochemistry, 3, pp. 1545-1561
- Wolberg, A.S., Gabriel, D.A., Hoffman, M., Analyzing fibrin clot structure using a microplate reader (2002) Blood Coagulation and Fibrinolysis, 13, pp. 533-539
- Wu, J.H., Siddiqui, K., Diamond, S.L., Transport phenomena and clot dissolving therapy: An experimental investigation of diffusion-controlled and permeation-enhanced fibrinolysis (1994) Thrombosis and Haemostasis, 72, pp. 105-112
Citas:
---------- APA ----------
Arata, P.X., Quintana, I., Raffo, M.P. & Ciancia, M.
(2016)
. Novel sulfated xylogalactoarabinans from green seaweed Cladophora falklandica: Chemical structure and action on the fibrin network. Carbohydrate Polymers, 154, 139-150.
http://dx.doi.org/10.1016/j.carbpol.2016.07.088---------- CHICAGO ----------
Arata, P.X., Quintana, I., Raffo, M.P., Ciancia, M.
"Novel sulfated xylogalactoarabinans from green seaweed Cladophora falklandica: Chemical structure and action on the fibrin network"
. Carbohydrate Polymers 154
(2016) : 139-150.
http://dx.doi.org/10.1016/j.carbpol.2016.07.088---------- MLA ----------
Arata, P.X., Quintana, I., Raffo, M.P., Ciancia, M.
"Novel sulfated xylogalactoarabinans from green seaweed Cladophora falklandica: Chemical structure and action on the fibrin network"
. Carbohydrate Polymers, vol. 154, 2016, pp. 139-150.
http://dx.doi.org/10.1016/j.carbpol.2016.07.088---------- VANCOUVER ----------
Arata, P.X., Quintana, I., Raffo, M.P., Ciancia, M. Novel sulfated xylogalactoarabinans from green seaweed Cladophora falklandica: Chemical structure and action on the fibrin network. Carbohydr Polym. 2016;154:139-150.
http://dx.doi.org/10.1016/j.carbpol.2016.07.088