Structure-Function Relationship of Anticoagulant and Antithrombotic Well-Defined Sulfated Polysaccharides from Marine Invertebrates

Advances in Food and Nutrition Research

Volumn 65, Issue , 2012, Pages 195-209

  Pomin, Vitor H ^a,b  

^a UNIVERSITY OF GEORGIA   (United States)

^b FEDERAL UNIVERSITY OF RIO DE JANEIRO   (Brazil)

Author keywords

Anticoagulant; Antithrombotic; Marine organisms; Sulfated fucan; Sulfated galactan

Indexed keywords

EID: 84857211730     PISSN: 10434526     EISSN: None     Source Type: Book Series    
DOI: 10.1016/B978-0-12-416003-3.00012-3     Document Type: Chapter

References (35)

1. Alves A.P., Mulloy B., Diniz J.A., Mourão P.A. Sulfated polysaccharides from the egg jelly layer are species-specific inducers of acrosomal reaction in sperms of sea urchins. J. Biol. Chem. 1997, 272:6965-6971.
2. Alves A.P., Mulloy B., Moy G.W., Vacquier V.D., Mourão P.A. Females of the sea urchin Strongylocentrotus purpuratus differ in the structures of their egg jelly sulfated fucans. Glycobiology 1998, 8:939-946.
3. Becker C.F., Guimaraes J.A., Mourão P.A., Verli H. Conformation of sulfated galactan and sulfated fucan in aqueous solutions: Implications to their anticoagulant activities. J. Mol. Graph. Model. 2007, 26:391-399.
4. Berteau O., Mulloy B. Sulfated fucans, fresh perspectives: Structures, functions, and biological properties of sulfated fucans and an overview of enzymes active toward this class of polysaccharide. Glycobiology 2003, 13:29R-40R.
5. Castro M.O., Pomin V.H., Santos L.L., Vilela-Silva A.C., Hirohashi N., Pol-Fachin L., Verli H., Mourão P.A. A unique 2-sulfated {beta}-galactan from the egg jelly of the sea urchin Glyptocidaris crenularis: Conformation flexibility versus induction of the sperm acrosome reaction. J. Biol. Chem. 2009, 284:18790-18800.
6. Coombe D.R., Parish C.R., Ramshaw I.A., Snowden J.M. Analysis of the inhibition of tumour metastasis by sulphated polysaccharides. Int. J. Cancer 1987, 39:82-88.
7. Cumashi A., Ushakova N.A., Preobrazhenskaya M.E., D'Incecco A., Piccoli A., Totani L., Tinari N., Morozevich G.E., Berman A.E., Bilan M.I., Usov A.I., Ustyuzhanina N.E., et al. A comparative study of the anti-inflammatory, anticoagulant, antiangiogenic, and antiadhesive activities of nine different fucoidans from brown seaweeds. Glycobiology 2007, 17:541-552.
8. Fareed J.W., Hoppensteadt D., Bick R.L. An update on heparins at the beginning of the new millennium. Sem. Thromb. Haemost. 2000, 26:5-21.
9. Farias W.R., Valente A.P., Pereira M.S., Mourão P.A. 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. 2000, 275:29299-29307.
10. Fonseca R.J., Oliveira S.N., Melo F.R., Pereira M.G., Benevides N.M., Mourão P.A. Slight differences in sulfation of algal galactans account for differences in their anticoagulant and venous antithrombotic activities. Thromb. Haemost. 2008, 99:539-545.
11. Gandhi N.S., Mancera R.L. The structure of glycosaminoglycans and their interactions with proteins. Chem. Biol. Drug Des. 2008, 72:455-482.
12. Guerrini M., Beccati D., Shriver Z., Naggi A., Viswanathan K., Bisio A., Capila I., Lansing J.C., Guglieri S., Fraser B., Al-Hakim A., Gunay N.S., et al. Oversulfated chondroitin sulfate is a contaminant in heparin associated with adverse clinical events. Nat. Biotechnol. 2008, 10:1-7.
13. Harrop H.A., Rider C.C., Coombe D.R. Sulphated polysaccharides exert anti-HIV activity at differing sites. Biochem. Soc. Trans. 1992, 20:163S.
14. Kishimoto T.K., Viswanathan K., Ganguly T., Elankumaran S., Smith S., Pelzer K., Lansing J.C., Sriranganathan N., Zhao G., Galcheva-Gargova Z., Al-Hakim A., Bailey G.S., et al. Contaminated heparin associated with adverse clinical events and activation of the contact system. N. Engl. J. Med. 2008, 358:1-11.
15. Melo F.R., Pereira M.S., Foguel D., Mourão P.A. Antithrombin-mediated anticoagulant activity of sulfated polysaccharides: Different mechanisms for heparin and sulfated galactans. J. Biol. Chem. 2004, 279:20824-20835.
16. Mourão P.A. Use of sulfated fucans as anticoagulant and antithrombotic agents: Future perspectives. Curr. Pharm. Design 2004, 10:967-981.
17. Mourão P.A. A carbohydrate-based mechanism of species recognition in sea urchin fertilization. Braz. J. Med. Biol. Res. 2007, 40:5-17.
18. Mourão P.A., Pereira M.S. Searching for alternatives to heparin: Sulfated fucans from marine invertebrates. Trends Cardiovasc. Med. 1999, 9:225-232.
19. Mourão P.A., Perlin A.S. Structural features of sulfated glycans from the tunic of Styela plicata (Chordata-Tunicata). A unique occurrence of L-galactose in sulfated polysaccharides. Eur. J. Biochem. 1987, 166:431-436.
20. Mulloy B., Ribeiro A.C., Alves A.P., Vieira R.P., Mourão P.A. Sulfated fucans from echinoderms have a regular tetrasaccharide repeating unit defined by specific patterns of sulfation at the 0-2 and 0-4 positions. J. Biol. Chem. 2004, 269:22113-22123.
21. Pavão M.S. Structure and anticoagulant properties of sulfated glycosaminoglycans from primitive Chordates. An. Acad. Bras. Cien. 2002, 74:105-112.
22. Pavão M.S., Mourão P.A., Mulloy B., Tollefsen D.M. A unique dermatan sulfate-like glycosaminoglycan from ascidian. Its structure and the effect of its unusual sulfation pattern on anticoagulant activity. J. Biol. Chem. 1995, 270:31027-31036.
23. Pavão M.S., Aiello K.R., Werneck C.C., Silva L.C., Valente A.P., Mulloy B., Colwell N.S., Tollefsen D.M., Mourão P.A. Highly sulfated dermatan sulfates from Ascidians. Structure versus anticoagulant activity of these glycosaminoglycans. J. Biol. Chem. 1998, 273:27848-27857.
24. Pereira M.S., Mulloy B., Mourão P.A. Structure and anticoagulant activity of sulfated fucans. Comparison between the regular, repetitive, and linear fucans from echinoderms with the more heterogeneous and branched polymers from brown algae. J. Biol. Chem. 1999, 274:7656-7667.
25. Pereira M.S., Melo F.R., Mourão P.A. Is there a correlation between structure and anticoagulant action of sulfated galactans and sulfated fucans?. Glycobiology 2002, 12:573-580.
26. Pereira M.S., Vilela-Silva A.C., Valente A.P., Mourão P.A. A 2-sulfated, 3-linked alpha-L-galactan is an anticoagulant polysaccharide. Carbohydr. Res. 2002, 337:2231-2238.
27. Pereira M.G., Benevides N.M., Melo M.R., Valente A.P., Melo F.R., Mourão P.A. Structure and anticoagulant activity of a sulfated galactan from the red alga, Gelidium crinale. Is there a specific structural requirement for the anticoagulant action?. Carbohydr. Res. 2005, 340:2015-2023.
28. Pomin V.H. Review: An overview about the structure-function relationship of marine sulfated homopolysaccharides with regular chemical structures. Biopolymers 2008, 91:601-609.
29. Pomin V.H. Structural and functional insights into sulfated galactans: A systematic review. Glycoconj. J. 2009, 27:1-12.
30. Pomin V.H., Mourão P.A. Structure, biology, evolution, and medical importance of sulfated fucans and galactans. Glycobiology 2008, 18:1016-1027.
31. Santos J.A., Mulloy B., Mourão P.A. Structural diversity among sulfated alpha-L-galactans from ascidians (tunicates). Studies on the species Ciona intestinalis and Herdmania monus. Eur. J. Biochem. 1992, 204:669-677.
32. Vicente C.P., Zancan P., Peixoto L.L., Alves-Sá R., Araújo F.S., Mourão P.A., Pavão M.S. Unbalanced effects of dermatan sulfates with different sulfation patterns on coagulation, thrombosis and bleeding. Thromb. Haemost. 2001, 86:1215-1220.
33. Vilela-Silva A.C., Alves A.P., Valente A.P., Vacquier V.D., Mourão P.A. Structure of the sulfated alpha-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 1999, 9:927-933.
34. Vilela-Silva A.C., Castro M.O., Valente A.P., Biermann C.H., Mourão P.A. Sulfated fucans from the egg jellies of the closely related sea urchins Strongylocentrotus droebachiensis and Strongylocentrotus pallidus ensure species-specific fertilization. J. Biol. Chem. 2002, 277:379-387.
35. Vilela-Silva A.C., Hirohashi N., Mourão P.A. The structure of sulfated polysaccharides ensures a carbohydrate-based mechanism for species recognition during sea urchin fertilization. Int. J. Dev. Biol. 2008, 52:551-559.