A heparin-like compound isolated from a marine crab rich in glucuronic acid 2-O-sulfate presents low anticoagulant activity

Carbohydr Polym. 2013 Apr 15;94(1):647-54. doi: 10.1016/j.carbpol.2013.01.069. Epub 2013 Jan 29.

Abstract

A natural heparin-like compound isolated from the crab Goniopsis cruentata was structurally characterized and its anticoagulant and hemorrhagic activities were determined. Enzymatic and nuclear magnetic resonance analysis revealed that its structure is rich in disulfated disaccharides, possessing significant amounts of 2-O-sulfated-β-D-glucuronic acid units. Furthermore, low amounts of trisulfated disaccharide units containing 2-O-sulfated-α-L-iduronic acid were detected, when compared to mammalian heparin. In addition, this heparin-like structure showed negligible in vitro anticoagulant activity and low bleeding potency, facts that make it a suitable candidate for the development of structure-driven, heparin based therapeutic agents with fewer undesirable effects.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anticoagulants / chemistry
  • Anticoagulants / isolation & purification
  • Anticoagulants / pharmacology*
  • Brachyura / chemistry*
  • Carbohydrate Conformation
  • Carbohydrate Sequence
  • Cattle
  • Disaccharides / chemistry
  • Glucosamine / chemistry
  • Glucuronates / chemistry*
  • Glucuronates / isolation & purification
  • Heparin / chemistry
  • Heparin / isolation & purification
  • Heparin / pharmacology*
  • Heparitin Sulfate / chemistry
  • Magnetic Resonance Spectroscopy
  • Male
  • Molecular Weight
  • Partial Thromboplastin Time
  • Rats
  • Uronic Acids / chemistry

Substances

  • Anticoagulants
  • Disaccharides
  • Glucuronates
  • Uronic Acids
  • Heparin
  • Heparitin Sulfate
  • glucuronic acid 2-sulfate
  • Glucosamine