Further data on the structure of brown seaweed fucans: relationships with anticoagulant activity

doi:10.1016/S0008-6215(99)00127-5

Carbohydrate Research

Volume 319, Issues 1–4, 30 June 1999, Pages 154-165

https://doi.org/10.1016/S0008-6215(99)00127-5 Get rights and content

Abstract

The composition, molecular weight (MW), anticoagulant activity and nuclear magnetic resonance spectra of various low-molecular-weight fucans (LMWFs) obtained by partial hydrolysis or radical depolymerization of a crude fucoidan extracted from the brown seaweed Ascophyllum nodosum are compared. Fucose units were found mainly sulfated at O-2, to a lesser extent at O-3, and only slightly at O-4, contrary to previously published results for fucoidans from other brown seaweeds, and fucose 2, 3-O-disulfate residues were observed for the first time. As the sulfation pattern excluded an α-(1→2)-linked fucose backbone and a high proportion of α-(1→4) linkages was found, it would appear that the concept of fucoidan structure needs to be revised. Anticoagulant activity is apparently related not only to MW and sulfation content, as previously determined, but also (and more precisely) to 2-O-sulfation and 2,3-O-disulfation levels.

Section snippets

. Introduction

Fucoidans, a unique class of sulfated fucans isolated from many brown seaweeds, have not been found in other algae or plants [1]. Their composition varies with the species, but they always contain essentially fucose and sulfate, with small proportions of galactose, xylose, mannose and uronic acids. Although various biological activities (anticoagulant, antithrombotic, antiviral, antiproliferative, antifertilizing and antitumoral) are associated with these compounds [2], [3], their structure is

Preparation, composition and properties of LMWFs

Only enzymatic methods can cleave glycosidic linkages specifically without modifying the structural units composing the original polysaccharide. However, no commercial endofucosidase is available. Though chemical methods cause structural alterations, such as debranching or desulfation, we assumed that two different methods (classical acid hydrolysis [13], [14] and a radical depolymerization process [15]) would not produce the same alterations and thus the same mixture of oligosaccharides.

The

Preparation of LMWFs

Crude fucoidan was extracted as described previously [33]. The acid hydrolysis procedure has already been briefly reported in Ref. [13]. Freeze-dried crude fucoidan was dissolved at a concentration of 10 mg/mL in 1 N H₂SO₄, and hydrolysis was performed at 60 °C for 1.5 h. After neutralization with NaOH, the resulting hydrolysates were desalted by tangential ultrafiltration (5000 Da cut-off membrane; Filtron, Clinton, MA, USA) and freeze-dried. The lyophilisate (500 mg) was then redissolved in 5

Acknowledgements

The authors are grateful to Ms J. Ratiskol and C. Marchand for their technical assistance, Ms C. Sternberg for performing APTT tests, and Dr S. Colliec for fruitful discussions. They also wish to thank Drs J. Jozefonvicz and P. Durand for their attention to this work, and Mr J. Gray for reviewing and improving the original text. They are especially indebted to Dr R. Pichon (University of Brest, France) for advice and assistance in his Department and Dr B. Mulloy (National Institute for

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Further data on the structure of brown seaweed fucans: relationships with anticoagulant activity

Abstract

Section snippets

. Introduction

Preparation, composition and properties of LMWFs

Preparation of LMWFs

Acknowledgements

J. Biol. Chem.

Carbohydr. Res.

Carbohydr. Res.

Carbohydr. Res.

Carbohydr. Res.

Phytochemistry

Carbohydr. Res.

J. Chromatogr. B

J. Biol. Chem.

J. Biol. Chem.

J. Biol. Chem.

Carbohydr. Res.

Carbohydr. Res.

Carbohydr. Res.

Carbohydr. Res.

Carbohydr. Res.

Carbohydr. Res.

Carbohydr. Res.