Structural Elucidation and Biological Activity of a Highly Regular Fucosylated Glycosaminoglycan from the Edible Sea Cucumber Stichopus herrmanni

J Agric Food Chem. 2017 Oct 25;65(42):9315-9323. doi: 10.1021/acs.jafc.7b03867. Epub 2017 Oct 17.

Abstract

Edible sea cucumbers are widely used as a health food and medicine. A fucosylated glycosaminoglycan (FG) was purified from the high-value sea cucumber Stichopus herrmanni. Its physicochemical properties and structure were analyzed and characterized by chemical and instrumental methods. Chemical analysis indicated that this FG with a molecular weight of ∼64 kDa is composed of N-acetyl-d-galactosamine, d-glucuronic acid (GlcA), and l-fucose. Structural analysis clarified that the FG contains the chondroitin sulfate E-like backbone, with mostly 2,4-di-O-sulfated (85%) and some 3,4-di-O-sulfated (10%) and 4-O-sulfated (5%) fucose side chains that link to the C3 position of GlcA. This FG is structurally highly regular and homogeneous, differing from the FGs of other sea cucumbers, for its sulfation patterns are simpler. Biological activity assays indicated that it is a strong anticoagulant, inhibiting thrombin and intrinsic factor Xase. Our results expand the knowledge on structural types of FG and illustrate its biological activity as a functional food material.

Keywords: Stichopus herrmanni; anticoagulant; chemical structure; fucosylated glycosaminoglycan; sea cucumber.

MeSH terms

  • Animals
  • Anticoagulants / chemistry
  • Anticoagulants / isolation & purification
  • Anticoagulants / pharmacology
  • Blood Coagulation / drug effects
  • Fucose / chemistry
  • Functional Food / analysis
  • Glucuronic Acid / analysis
  • Glycosaminoglycans / chemistry*
  • Glycosaminoglycans / isolation & purification
  • Glycosaminoglycans / pharmacology
  • Humans
  • Magnetic Resonance Spectroscopy
  • Molecular Weight
  • Seafood / analysis*
  • Stichopus / chemistry*

Substances

  • Anticoagulants
  • Glycosaminoglycans
  • Fucose
  • Glucuronic Acid