Chemical structure of antithrombin-active rhamnan sulfate from monostrom nitidum

Bioscience, Biotechnology and Biochemistry

Volumn 62, Issue 9, 1998, Pages 1647-1652

  Harada, Naoki ^a,b   Maeda, Masaakira ^a  

^a SAITAMA UNIVERSITY   (Japan)

^b CHUGAI PHARMACEUTICAL CO LTD   (Japan)

Author keywords

Antithrombin activity; Chlorophyta; Monostroma nitidum; Rhamnan sulfate; Sulfated cell wall polysaccharides

Indexed keywords

DEOXYSUGAR; MANNAN; RHAMNAN; SULFATE; THROMBIN;

ALGA; ARTICLE; CARBOHYDRATE ANALYSIS; CHEMISTRY; DRUG ANTAGONISM; MOLECULAR GENETICS;

ALGAE; CARBOHYDRATE SEQUENCE; DEOXY SUGARS; MANNANS; MOLECULAR SEQUENCE DATA; SULFATES; THROMBIN;

EID: 0032150699     PISSN: 09168451     EISSN: 13476947     Source Type: Journal    
DOI: 10.1271/bbb.62.1647     Document Type: Article

References (30)

1. Percival, E., and McDowell, R. H., in “Chemistry andEnzymol-ogy of Marine Algal Polysaccharides.” Academic Press, London, pp. 51-72 (1967).
2. Brading, J. W. E., Geror-Plant, M. M. T., and Hardy, D. M. The polysaccharide from the alga Ulva lactuca. Purification, hydrolysis, and méthylation of the polysaccharide. J. Chem. Soc., 319-324 (1954).
3. McKinnell, J. P. and Percival, E. The acid polysaccharide from the green seaweed. J. Chem. Soc., 2082-2083 (1962).
4. McKinnell, J. P. and Percival, E., Structural investigations on the water-soluble polysaccharide of the green seaweed En-teromorpha compressa, J. Chem. Soc., 3141-3148 (1962).
5. Lahaye, M., Jegou, D., and Buleon, A., Chemical characteristics of insoluble glucans from the cell wall of the marune green alga Ulva lactuca (L) Thuret. Carbohydr. Res., 262, 115-125 (1994).
6. Lahaye, M. and Ray, B., Cell wall polysaccharides from the marine green alga Ulva “rigida” (Ulvales, Chlorophyta)-NMR analysis of ulvan oligosaccharides. Carbohydr. Res., 283, 161-173 (1996).
7. Percival, E. and Wold, J. K., The acid polysaccharide from the green seaweed Ulva lactuca. (II) The site of the ester sulfate. J. Chem. Soc., 5459-5468 (1963).
8. Maeda, M., Uehara, T., Harada, N., Sekiguchi, M. and Hiraoka, A., Heparinoid-active sulphated polysaccharides from Monostroma nitidum and their distribution in the Chlorophyta. Phytochemistry, 30, 3611-3614 (1991).
9. Dubois, M., Gilles, K. A., Hamilton, J. K., Rebers, P. A. and Smith, F., Colorimetric method for determination of sugar and related substances. Anal. Chem., 28, 350-356 (1956).
10. Bitter, T. and Muir, H. M., A modified uronic acid carbazole reaction. Anal. Biochem., 4, 330-334 (1962).
11. Lowry, O. H., Rosebrdugh, N. J., Farr A. L. and Randall, R. J. Protein measurement with the Folin phenol reagent. J. Biol. Chem., 193, 265-275 (1951).
12. Shimada, K., Igarashi, M. and Asada, T., A new method for the assay of heparin, heparin cofactor method. J. Med. Soc. Toho Japan (in Japanease);, 18, 939-944 (1971). [Chem. Abst., 77, 105653h (1972)].
13. Imanari, T., Arakawa, Y. and Tamura, Z., Gas chromatographic analysis of aldoses. Chem. Pharm. Bull., 17,1967-1969 (1969).
14. Collins, P. M. (ed)., in “Carbohydrates”. Chapman and Hall, London, pp. 433-434. (1987).
15. Hiraoka, A., Harada, N., Uehara, T., Sekiguchi, M. and Maeda, M., Capilary-isotachophoretic analyses of algal acidic polysaccharides and their application to a survey of heparinoid active sulfated polysaccharides in Chlorophyta. Chem. Pharm. Bull., 40, 783-785 (1992).
16. Terho T. T. and Hartiala, K., Method for determination of the sulfate content of glycosamino glycans. Anal. Biochem., 41, 471-476 (1971).
17. Yamagaki, T., Tsuji, Y., Maeda, M. and Nakanishi, H., NMR spectroscopic analysis of sulfated yff-1,3-xylan and sulfation stereochemistry. Biosci. Biotech. Biochem., 61, 1281-1285 (1997).
18. Nagasawa, K., Inoue, Y. and Tokuyasu, T., An improved method for the preparation of chondroitin by solvolytic desulfation of chondroitin sulfate. J. Biochem. (Tokyo), 86, 1323-1329 (1979).
19. Fairbridge, R. A., Willis, K. J. and Booth, R. G„ The direct colorimetric estimation of reducing sugars and other reducing substances with tetrazolium salts. Biochem. J., 49, 423-426 (1951).
20. Aspinall, G. O. and Ferrier, R. J., A spectrophotometric method for the determination of periodate consumed during the oxidation of carbohydrates. Chem. &Ind., 1216 (1957).
21. Sweeley, C. C., Bently, R., Makita, M. and Wells, W. W., Gas-liquid chromatography of trimethylsilyl derivatives of sugar and related substances. J. Am. Chem. Soc., 85, 2497-2507 (1963).
22. Furneaux, R. H. and Stevenson, T. T., Chemical methods for the analysis of sulphated galactans from red algae. Carbohydr. Res., 210, 277-298 (1991).
23. S. Hakomori, A rapid permethylation of glycolipid and polysaccharide catalysed by methylsulfinyl carbanion in dimethyl sulfoxide. J. Biochem. (Tokyo), 55, 205-208 (1964).
24. Yamagaki, T., Maeda, M., Kanazawa, K., Ishizuka, Y. and Nakanishi, H., Structures of Caulerpa cell wall microfibril xylan with detection of /?-1,3-xylooligosaccharides by matrix-assisted laser desorption ionization/time of flight/mass spectrometry. Biosci. Biotech. Biochem., 60, 1222-1228 (1996).
25. Lonngren, J. and Pilotti, A., Gas-liquid chromatography of partially methylated alditols as their acetates (II). Acta Chem. Scand., 25, 1144-1145 (1971).
26. Lindberg, B., Methylation analysis of polysaccharides. Methods Enzymol., 28, 178-195 (1972); Hellerqvist, C. G., Linkage analysis using Lindberg method. Methods Enzymol., 193, 554-573 (1990).
27. Orr, S. F. D., Infra-red spectroscopic studies of some polysaccharides. Biochim. Biophys. Acta, 14, 173-181 (1954).
28. Dutton, G. G. S., Fabio, J. L. DI. and Zanlungo, A. B., Structure of the capsular polysaccharide of Klebsiella serotype K45. Carbohydr. Res., 106, 93-100 (1982).
29. Wolform, M. L. and McNeely, W. H., The relation between the structure of heparin and its anticoagulant activity. J. Am. Chem. Soc., 67, 748-753 (1945).
30. Hayashi, T., Hayashi, K., Maeda, M. and Kojima, I., Calsium spirulan, an inhibitor of enveloped virus replication, from a blue-green alga Spirulina platensis. J. Nat. Prod., 59, 83-87 (1996).