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J Biol Chem, Vol. 273, Issue 43, 27848-27857, October 23, 1998

Highly Sulfated Dermatan Sulfates from Ascidians
STRUCTURE VERSUS ANTICOAGULANT ACTIVITY OF THESE GLYCOSAMINOGLYCANS

Mauro S. G. Pavão, Karin R. M. Aiello, Claudio C. Werneck, Luiz Claudio F. Silva, Ana-Paula Valente^§, Barbara Mulloy^¶, Niall S. Colwell, Douglas M. Tollefsen, and Paulo A. S. Mourão

From the  Laboratório de Tecido Conjuntivo, Hospital Universitário and Departamento de Bioquímica Médica, Centro de Ciências da Saúde, Universidade Federal do Rio de Janeiro, Caixa Postal 68041, Rio de Janeiro, RJ, 21941-590, Brazil, ^§ Centro Nacional de Ressonância Magnética Nuclear de Macromoléculas, Departamento de Bioquímica Médica, Universidade Federal do Rio de Janeiro, Rio de Janeiro, RJ, 21941-590, Brazil, ^¶ National Institute for Biological Standards and Control, South Mimms, Potters Bar, Hertfordshire, EN6 3QG, United Kingdom, and  Division of Hematology, Department of Internal Medicine, Washington University School of Medicine, St. Louis, Missouri 63110

Dermatan sulfates with the same backbone structure [4--L-IdceA-13--D-GalNAc-1]_n but with different patterns of sulfation substitutions have been isolated from the ascidian body. All the ascidian dermatan sulfates have a high content of 2-O-sulfated -L-iduronic acid residues but differ in the pattern of sulfation of the N-acetyl--D-galactosamine units. Styela plicata and Halocynthia pyriformis have 4-O-sulfated units, but in Ascidian nigra they are 6-O-sulfated. This collection of ascidian dermatan sulfates (together with native and oversulfated mammalian dermatan sulfate), where the extent and position of sulfate substitution have been fully characterized, were tested in anticoagulant assays. Dermatan sulfate from A. nigra has no discernible anticoagulant activity, which indicates that 4-O-sulfation of the N-acetyl--D-galactosamine is essential for the anticoagulant activity of this glycosaminoglycan. In contrast dermatan sulfates from S. plicata and H. pyriformis are potent anticoagulants due to potentiation of thrombin inhibition by heparin cofactor II. These ascidian dermatan sulfates have ~10-fold and ~6-fold higher activity with heparin cofactor II than native and an oversulfated mammalian dermatan sulfate, respectively. They have no effect on thrombin or factor Xa inhibition by antithrombin. These naturally oversulfated ascidian dermatan sulfates are sulfated at selected sites required for interaction with heparin cofactor II and thus have specific and potent anticoagulant activity.

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Copyright © 1998 by The American Society for Biochemistry and Molecular Biology, Inc.

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