Sequence determination and anticoagulant and antithrombotic activities of a novel sulfated fucan isolated from the sea cucumber Isostichopus badionotus

Biochimica et Biophysica Acta - General Subjects

Volumn 1820, Issue 7, 2012, Pages 989-1000

  Chen, Shiguo ^a   Hu, Yaqin ^a   Ye, Xinqian ^a   Li, Guoyun ^b   Yu, Guangli ^b   Xue, Changhu ^b   Chai, Wengang ^c  

^a ZHEJIANG UNIVERSITY   (China)

^b OCEAN UNIVERSITY OF CHINA   (China)

^c IMPERIAL COLLEGE LONDON   (United Kingdom)

Author keywords

Anticoagulant; Antithrombotic; ES MS; Fucan; NMR; Sea cucumber

Indexed keywords

ANTICOAGULANT AGENT; ANTITHROMBIN; BLOOD CLOTTING FACTOR 10A; CHONDROITIN SULFATE; FUCOSYLATED CHONDROITIN SULFATE; HEPARIN; HEPARIN COFACTOR II; POLYSACCHARIDE; PROTHROMBIN A; SULFATED FUCAN; THROMBIN; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANTICOAGULATION; ANTITHROMBOTIC ACTIVITY; ARTICLE; CHEMICAL BOND; COLLISIONALLY ACTIVATED DISSOCIATION; CONTROLLED STUDY; DRUG ACTIVITY; DRUG DETERMINATION; DRUG HYDROLYSIS; DRUG ISOLATION; DRUG STRUCTURE; IN VITRO STUDY; ISOSTICHOPUS BADIONOTUS; MALE; NEGATIVE ION ELECTROSPRAY; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; PARTIAL THROMBOPLASTIN TIME; PRIORITY JOURNAL; RAT; SEA CUCUMBER; TANDEM MASS SPECTROMETRY; THROMBOGENESIS;

ANIMALS; ANTICOAGULANTS; BLOOD COAGULATION; BLOOD COAGULATION TESTS; CARBOHYDRATE SEQUENCE; FACTOR XA; MAGNETIC RESONANCE SPECTROSCOPY; MALE; MOLECULAR SEQUENCE DATA; POLYSACCHARIDES; RATS; RATS, SPRAGUE-DAWLEY; SEA CUCUMBERS; SEQUENCE ANALYSIS; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; TANDEM MASS SPECTROMETRY; THROMBIN; THROMBOSIS;

HOLOTHUROIDEA; ISTICHOPUS BADIONOTUS;

EID: 84860695994     PISSN: 03044165     EISSN: 18728006     Source Type: Journal    
DOI: 10.1016/j.bbagen.2012.03.002     Document Type: Article

References (40)

1. X. Fu, C. Xue, B. Miao, Z. Li, X. Gao, and W. Yang Characterization of proteases from the digestive tract of sea cucumber (Stichopus japonicus): High alkaline protease activity Aquaculture 246 2005 321 329
2. Y. Zhou, H. Yang, S. Liu, X. Yuan, Y. Mao, Y. Liu, X. Xu, and F. Zhang Feeding and growth on bivalve biodeposits by the deposit feeder Stichopus japonicus Selenka (Echinodermata: Holothuroidea) co-cultured in lantern nets Aquaculture 256 2006 510 520
3. V. Kalinin System-theoretical (Holistic) approach to the modelling of structural-functional relationships of biomolecules and their evolution: an example of triterpene glycosides from sea cucumbers (Echinodermata, Holothurioidea) J. Theor. Biol. 206 2000 151 168
4. J. Trotter, G. Lyons-Levy, F. Thurmond, and T. Koob Covalent composition of collagen fibrils from the dermis of the sea cucumber, Cucumaria frondosa, a tissue with mutable mechanical properties Comp. Biochem. Physiol. A Comp. Physiol. 112 1995 463 478
5. J. Sheehan, and E. Walke Depolymerized holothurian glycosaminoglycan and heparin inhibit the intrinsic tenase complex by a common antithrombin- independent mechanism Blood 107 2006 3876
6. R.J. Fonseca, and P.A. Mourao Fucosylated chondroitin sulfate as a new oral antithrombotic agent Thromb. Haemost. 96 2006 822 829
7. P.A. Mourao, M.S. Pereira, M.S. Pavao, B. Mulloy, D.M. Tollefsen, M.C. Mowinckel, and U. Abildgaard Structure and anticoagulant activity of a fucosylated chondroitin sulfate from echinoderm. Sulfated fucose branches on the polysaccharide account for its high anticoagulant action J. Biol. Chem. 271 1996 23973 23984
8. J. Tapon-Bretaudiere, D. Chabut, M. Zierer, S. Matou, D. Helley, A. Bros, P.A. Mourao, and A.M. Fischer A fucosylated chondroitin sulfate from echinoderm modulates in vitro fibroblast growth factor 2-dependent angiogenesis Mol. Cancer Res. 1 2002 96 102
9. L. Borsig, L. Wang, M.C. Cavalcante, L. Cardilo-Reis, P.L. Ferreira, P.A. Mourao, J.D. Esko, and M.S. Pavao Selectin blocking activity of a fucosylated chondroitin sulfate glycosaminoglycan from sea cucumber. Effect on tumor metastasis and neutrophil recruitment J. Biol. Chem. 282 2007 14984 14991
10. O. Berteau, and B. Mulloy Sulfated fucans, fresh perspectives: structures, functions, and biological properties of sulfated fucans and an overview of enzymes active toward this class of polysaccharide Glycobiology 13 2003 29 40
11. P.A. Mourao Use of sulfated fucans as anticoagulant and antithrombotic agents: Future perspectives: Heparin and heparinoids: Correlation between structure and antithrombotic activity. Clinical applications and future perspectives Curr. Pharm. Design 10 2004 967 981
12. A. Vilela-Silva, A. Alves, A. Valente, V. Vacquier, and P.A. Mourao 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 9 1999 927 933
13. S. Chen, J. Wang, C. Xue, H. Li, B. Sun, Y. Xue, and W. Chai Sulfation of a squid ink polysaccharide and its inhibitory effect on tumor cell metastasis Carbohydr. Polym. 81 2010 560 566
14. V.H. Pomin An overview about the structure-function relationship of marine sulfated homopolysaccharides with regular chemical structures Biopolymers 91 2009 601 609
15. S. Chen, C. Xue, L. Yin, Q. Tang, G. Yu, and W. Chai Comparison of structures and anticoagulant activities of fucosylated chondroitin sulfates from different sea cucumbers Carbohydr. Polym. 8 2011 688 695
16. A.C. Ribeiro, R.P. Vieira, P.A. Mourao, and B. Mulloy A sulfated alpha-L-fucan from sea cucumber Carbohydr. Res. 255 1994 225 240
17. M. Pereira, B. Mulloy, and P. Mourao Structure and anticoagulant activity of sulfated fucans: comparison between the regular, regular, repetitive, and linear fucans from echinoderms with more heterogeneous and branched polymers from brown algae J. Biol. Chem. 274 1999 1999 7656 7667
18. R. Vieira, and P. Mourao Occurrence of a unique fucose-branched chondroitin sulfate in the body wall of a sea cucumber J. Biol. Chem. 263 1988 18176 18183
19. 1H NMR J. Instrum. Anal. (Chinese) 8 2010 782 786
20. Y. Kariya, B. Mulloy, K. Imai, A. Tominaga, T. Kaneko, A. Asari, K. Suzuki, H. Masuda, M. Kyogashima, and T. Ishii Isolation and partial characterization of fucan sulfates from the body wall of sea cucumber Stichopus japonicus and their ability to inhibit osteoclastogenesis Carbohydr. Res. 339 2004 1339 1346
21. B. Mulloy, A.C. Ribeiro, R.P. Vieira, and P.A. Mourao Structural analysis of sulfated fucans by high-field NMR Braz. J. Med. Biol. Res. 27 1994 515 521
22. Y. Wada, A. Dell, S.M. Haslam, B. Tissot, K. Canis, P. Azadi, M. Backstrom, C.E. Costello, G.C. Hansson, and Y. Hiki Comparison of Methods for Profiling O-Glycosylation: Comparison of methods for profiling O-glycosylation: human proteome organisation human disease glycomics/ proteome initiative Mol. Cell Proteomics 9 2010 719 727
23. W. Chai, V. Piskarev, and A.M. Lawson Negative-ion electrospray mass spectrometry of neutral underivatized oligosaccharides Anal. Chem. 73 2001 651 657
24. C. Przybylski, F. Gonnet, D. B., Y. Hersant, H. Lortat-Jacob, and R. Daniel HABA-based ionic liquid matrices for UV-MALDI-MS analysis of heparin and heparan sulfate oligosaccharides Glycobiology 224 2010 225 231
25. G. Yu, X. Zhao, B. Yang, S. Ren, H. Guan, Y. Zhang, A.M. Lawson, and W. Chai Sequence determination of sulfated carrageenan-derived oligosaccharides by high-sensitivity negative-ion electrospray tandem mass spectrometry Anal. Chem. 78 2006 8499 8505
26. V.H. Pomin, M.S. Pereira, A.P. Valente, D.M. Tollefsen, M.S. Pavao, and P.A. Mourao Selective cleavage and anticoagulant activity of a sulfated fucan: stereospecific removal of a 2-sulfate ester from the polysaccharide by mild acid hydrolysis, preparation of oligosaccharides, and heparin cofactor II-dependent anticoagulant activity Glycobiology 15 2005 369 374
27. R.J.C. Fonseca, G.R.C. Santos, and P.A.S. Mourao Effects of polysaccharides enriched in 2, 4-disulfated fucose units on coagulation, thrombosis and bleeding Thromb. Haemost. 102 2009 829 836
28. D. Strydom Chromatographic separation of 1-phenyl-3-methyl-5- pyrazolone-derivatized neutral, acidic and basic aldoses J. Chromatogr. A 678 1994 17 23
29. S. Ohira, and K. Toda Ion chromatographic measurement of sulfide, methanethiolate, sulfite and sulfate in aqueous and air samples J. Chromatogr. A 1121 2006 280 284
30. C.Z. Lin, H.S. Guan, H.H. Li, G.L. Yu, C.X. Gu, and G.Q. Li The influence of molecular mass of sulfated propylene glycol ester of low-molecular-weight alginate on anticoagulant activities Eur. Polym. J. 43 2007 3009 3015
31. X. Zhang, Z. Liu, Z. Zhu, P. Yang, and R. Xie Infuuence of gypenosides on thrombsus and coagulation function in vivo and in vitro, West Chin J. Pharm. Sci. 14 1999 335 337
32. J. Zaia, and C.E. Costello Tandem mass spectrometry of sulfated heparin-like glycosaminoglycan oligosaccharides Anal. Chem. 75 2003 2445 2455
33. W. Chai, A.M. Lawson, and V. Piskarev Branching pattern and sequence analysis of underivatized oligosaccharides by combined MS/MS of singly and doubly charged molecular ions in negative-ion electrospray mass spectrometry J. Am. Soc. Mass Spectrom. 13 2002 670 679
34. W. Chai, V.E. Piskarev, B. Mulloy, Y. Liu, P.G. Evans, H.M.I. Osborn, and A.M. Lawson Analysis of chain and blood group type and branching pattern of sialylated oligosaccharides by negative ion electrospray tandem mass spectrometry Anal. Chem. 78 2006 1581 1592
35. B. Domon, and C.E. Costello A systematic nomenclature for carbohydrate fragmentations in FAB-MS/MS spectra of glycoconjugates Glycoconj. J. 5 1988 397 409
36. S. Chen, J. Xu, C. Xue, P. Dong, W. Sheng, G. Yu, and W. Chai Sequence determination of a non-sulfated glycosaminoglycan-like polysaccharide from melanin-free ink of the squid Ommastrephes bartrami by negative-ion electrospray tandem mass spectrometry and NMR spectroscopy Glycoconj. J. 25 2008 481 492
37. V.H. Pomin, A.P. Valente, M.S. Pereira, and P.A.S. Mourao Mild acid hydrolysis of sulfated fucans: a selective 2-desulfation reaction and an alternative approach for preparing tailored sulfated oligosaccharides Glycobiology 15 2005 1376 1385
38. B. Yang, G. Yu, X. Zhao, G. Jiao, S. Ren, and W. Chai Mechanism of mild acid hydrolysis of galactan polysaccharides with highly ordered disaccharide repeats leading to a complete series of exclusively odd numbered oligosaccharides FEBS J. 276 2009 2125 2137
39. P.A.S. Mourao, and M.S. Pereira Searching for Alternatives to Heparin: Sulfated Fucans from Marine Invertebrates Trends Cardiovasc. Med. 9 1999 225 232
40. M. Guerrini, D. Beccati, Z. Shriver, A. Naggi, K. Viswanathan, A. Bisio, I. Capila, J.C. Lansing, S. Guglieri, and B. Fraser Oversulfated chondroitin sulfate is a contaminant in heparin associated with adverse clinical events Nat. Biotechnol. 26 2008 669 675