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Glycobiology Advance Access originally published online on August 20, 2009
Glycobiology 2009 19(12):1485-1491; doi:10.1093/glycob/cwp123
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© The Author 2009. Published by Oxford University Press. All rights reserved. For permissions, please e-mail: journals.permissions@oxfordjournals.org

Structural analysis of chondroitin sulfate from Scyliorhinus canicula: A useful source of this polysaccharide

Valentina Gargiulo, Rosa Lanzetta, Michelangelo Parrilli and Cristina De Castro1

Department of Organic Chemistry and Biochemistry, University of Naples "Federico II", Complesso Universitario Monte Sant’Angelo, Via Cintia 4, 80126 Napoli, Italy

1 To whom correspondence should be addressed: Tel: +39-081674124; Fax: +39-081674393; e-mail: decastro{at}unina.it

Received on April 15, 2009; revised on July 18, 2009; accepted on August 13, 2009

Chondroitin sulfate (CS), a constituent of proteoglycans, is a key component of the connective tissues and it is widely used as a precautionary drug for joint diseases; for this reason, the increased demand of this polysaccharide has posed the problem to identify new and secure sources of this product. In this context, CS from the cartilage of the lesser spotted dogfish (Scyliorhinus canicula, a cartilaginous fish) was isolated and investigated through chemical and spectroscopical techniques. The structural elucidation was performed on the entire polysaccharide and confirmed analyzing the products obtained via ABC lyase treatment. As a result, its compositional analysis disclosed the occurrence of CS-A, CS-C, CS-D, and CS-0S motifs in the ratio of 41, 32, 19.8, and 8.2%, respectively. Additionally, two different glycopeptides were isolated and characterized via NMR, providing information on the linkage oligosaccharide region joining the glycosaminoglycan chain to the core protein. Therefore, chondroitin sulfate from Scyliorhinus canicula appears very similar to that isolated from shark, a cartilaginous and taxonomically related fish, with the main difference residing in the major percentage of the CS-A motif. In the light of the results obtained, Scyliorhinus canicula chondroitin sulfate possesses a chemical structure compatible for the formulation of commercial and pharmaceutical products.

Key words: 2D-NMR / chondroitin sulfate / lesser spotted dogfish / linkage region / RPIP-HPLC


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