Deaminative-cleaved S. monotuberculatus fucosylated glycosaminoglycan: Structural elucidation and anticoagulant activity

Carbohydr Polym. 2022 Dec 15:298:120072. doi: 10.1016/j.carbpol.2022.120072. Epub 2022 Sep 6.

Abstract

Stichopus monotuberculatus is a tropical sea cucumber species and used as a folk medicine and tonic food. In this study, a fucosylated glycosaminoglycan (SmFG), the depolymerized SmFG (dSmFG) and its oligosaccharide fractions were prepared. The SmFG and its depolymerized products were comprised of a chondroitin-sulfate-E backbone, and various sulfated fucose side chains, including an unusual disaccharide side chain connected to the C-3 position of D-glucuronic acid (GlcA) or GlcA-ol. A peeling reaction occurred during the deaminative depolymerization process. The dSmFG and its fractions showed strong anticoagulant activity by selectively inhibiting intrinsic tenase complex, and had no anti-factor IIa, Xa and VIIa activity. The anticoagulant activity reduced with the decrease of molecular weight, and the unusual branch and novel reducing end may enhance the anticoagulant activity. These findings can provide significant information for development and utilization of depolymerized products from SmFG in food and pharmaceutical industries.

Keywords: 2,5-Anhydrotalose (PubChem CID: 12303004).; 3-Methyl-1-phenyl-2-pyrazolin-5-one (PubChem CID: 4021); Anticoagulant activity; D-Galactose (PubChem CID: 6036); D-Glucuronic acid (PubChem CID: 94715); Deuterium oxide (PubChem CID: 24602); Enoxaparin (PubChem CID: 2005-06-23); Fucosylated glycosaminoglycan; Heparin sodium (PubChem CID: 92044406); Hydrazine hydrate (PubChem CID: 24654); L-Fucose (PubChem CID: 3034656); N-acetyl-D-galactosamine (PubChem CID: 35717); Oligosaccharides; Polysaccharides; Sea cucumber.

MeSH terms

  • Animals
  • Anticoagulants / chemistry
  • Anticoagulants / pharmacology
  • Chondroitin Sulfates / chemistry
  • Disaccharides
  • Fucose / chemistry
  • Glucuronic Acid
  • Glycosaminoglycans* / chemistry
  • Glycosaminoglycans* / pharmacology
  • Oligosaccharides / chemistry
  • Sea Cucumbers* / chemistry
  • Sulfates

Substances

  • Anticoagulants
  • Disaccharides
  • Glycosaminoglycans
  • Oligosaccharides
  • Sulfates
  • Fucose
  • Glucuronic Acid
  • Chondroitin Sulfates