The structure of the agaran sulfate from Acanthophora spicifera (Rhodomelaceae, Ceramiales) and its antiviral activity. Relation between structure and antiviral activity in agarans

Carbohydr Res. 2004 Jan 22;339(2):335-47. doi: 10.1016/j.carres.2003.09.028.

Abstract

The sulfated agaran isolated by water extraction from the red seaweed, Acanthophora spicifera (Rhodomelaceae, Ceramiales), is made up of A-units highly substituted with sulfate groups on C-2 (28-30%), sulfates on C-2 and 4,6-O-(1'-carboxyethylidene) groups (9-15%), and only the C-2 sulfate groups (5-8%) with small amounts of C-6 sulfate, 6-O-methyl, and nonsubstituted residues. B-units are formed mainly by 3,6-anhydro-alpha-L-galactose (15-16%) and its precursor, alpha-L-galactose 6-sulfate (10-17%), together with lesser amounts of 3,6-anhydro-alpha-L-galactose 2-sulfate, alpha-L-galactose 2,6-disulfate, alpha-L-galactose 2,3,6-tri-sulfate, alpha-L-galactose 2,6-disulfate 3-xylose, 2-O-methyl-alpha-L-galactose, and unsubstituted alpha-L-galactose. Small, but significant quantities of beta-D-xylose were found in all the fractions, together with small amounts to traces of D-glucose. Some of the fractions have high antiviral activity. Attempts to correlate structure and antiviral activity in agarans are presented.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Agar / chemistry*
  • Animals
  • Anticoagulants / chemistry
  • Anticoagulants / pharmacology
  • Antiviral Agents / chemistry*
  • Antiviral Agents / pharmacology*
  • Carbohydrate Conformation
  • Carbohydrate Sequence
  • Cell Survival / drug effects
  • Chlorocebus aethiops
  • Chromatography, Ion Exchange
  • Inhibitory Concentration 50
  • Molecular Sequence Data
  • Molecular Structure
  • Rhodophyta / chemistry*
  • Spectrometry, Mass, Electrospray Ionization
  • Structure-Activity Relationship
  • Sulfates / chemistry*
  • Sulfates / pharmacology*
  • Vero Cells
  • Viral Plaque Assay

Substances

  • Anticoagulants
  • Antiviral Agents
  • Sulfates
  • Agar