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Mar. Drugs 2016, 14(9), 170; doi:10.3390/md14090170

Depolymerization of Fucosylated Chondroitin Sulfate with a Modified Fenton-System and Anticoagulant Activity of the Resulting Fragments

1
Zhejiang Key Laboratory for Agro-Food Processing, Department of Food Science and Nutrition, Fuli Institute of Food Science, Zhejiang University, Hangzhou 310058, China
2
Center for Biotechnology & Interdisciplinary Studies, Department of Chemistry & Chemical Biology, Rensselaer Polytechnic Institute, Biotechnology Center 4005, Troy, NY 12180, USA
*
Author to whom correspondence should be addressed.
Academic Editor: Keith B. Glaser
Received: 27 July 2016 / Revised: 7 September 2016 / Accepted: 13 September 2016 / Published: 21 September 2016
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Abstract

Fucosylated chondroitin sulfate (fCS) from sea cucumber Isostichopus badionotus (fCS-Ib) with a chondroitin sulfate type E (CSE) backbone and 2,4-O-sulfo fucose branches has shown excellent anticoagulant activity although has also show severe adverse effects. Depolymerization represents an effective method to diminish this polysaccharide’s side effects. The present study reports a modified controlled Fenton system for degradation of fCS-Ib and the anticoagulant activity of the resulting fragments. Monosaccharides and nuclear magnetic resonance (NMR) analysis of the resulting fragments indicate that no significant chemical changes in the backbone of fCS-Ib and no loss of sulfate groups take place during depolymerization. A reduction in the molecular weight of fCS-Ib should result in a dramatic decrease in prolonging activated partial thromboplastin time and thrombin time. A decrease in the inhibition of thrombin (FIIa) by antithromin III (AT III) and heparin cofactor II (HCII), and the slight decrease of the inhibition of factor X activity, results in a significant increase of anti-factor Xa (FXa)/anti-FIIa activity ratio. The modified free-radical depolymerization method enables preparation of glycosaminoglycan (GAG) oligosaccharides suitable for investigation of clinical anticoagulant application. View Full-Text
Keywords: sea cucumber; fucosylated chondroitin sulfate; free-radical depolymerization; anticoagulant activity sea cucumber; fucosylated chondroitin sulfate; free-radical depolymerization; anticoagulant activity
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MDPI and ACS Style

Li, J.-H.; Li, S.; Zhi, Z.-J.; Yan, L.-F.; Ye, X.-Q.; Ding, T.; Yan, L.; Linhardt, R.J.; Chen, S.-G. Depolymerization of Fucosylated Chondroitin Sulfate with a Modified Fenton-System and Anticoagulant Activity of the Resulting Fragments. Mar. Drugs 2016, 14, 170.

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