Structural analysis and antiviral activity of a sulfated galactan from the red seaweed Schizymenia binderi (Gigartinales, Rhodophyta).
Aqueous extraction of gametophytic Schizymenia binderi afforded a polysaccharide composed of galactose and sulfate groups in a molar ratio of 1.0:0.89 together with uronic acids (6.8 wt%) and minor amounts of other neutral sugars. Alkali-treatment of the polysaccharide afforded a polysaccharide devoid of 3,6-anhydrogalactose. 13C NMR spectroscopy of the desulfated alkali-treated polysaccharide showed a backbone structure of alternating 3-linked beta-D-galactopyranosyl and 4-linked alpha-galactopyranosyl units that are predominantly of the D-configuration and partly of the L-configuration. Methylation, ethylation and NMR spectroscopic studies of the alkali-treated polysaccharide indicated that the sulfate groups are located mainly at positions O-2 of 3-linked beta-D-galactopyranosyl residue and at position O-3 of 4-linked-alpha-galactopyranosyl residues, the latter is partially glycosylated at position O-2. The sulfated galactan from S. binderi exhibited highly selective antiviral activity against Herpes simplex virus types 1 and 2, with selectivity indices (ratio cytotoxicity/antiviral activity) >1000 for all assayed virus strains. This compound was shown to interfere with the initial adsorption of viruses to cells.
Matsuhiro
Betty
B
Departamento de Ciencias Químicas, Facultad de Química y Biología, Universidad de Santiago de Chile, Casilla 40, Santiago 33, Chile. bmatsuhi@lauca.usach.cl
Conte
Ana F
AF
Damonte
Elsa B
EB
Kolender
Adriana A
AA
Matulewicz
María C
MC
Mejías
Enrique G
EG
Pujol
Carlos A
CA
Zúñiga
Elisa A
EA
D000478:Alkylation; D000818:Animals; D000998:Antiviral Agents / Q000737:chemistry* / Q000494:pharmacology*; D002236:Carbohydrate Conformation; D002470:Cell Survival; D002522:Chlorocebus aethiops; D005685:Galactans / Q000737:chemistry* / Q000494:pharmacology*; D018259:Herpesvirus 1, Human / Q000187:drug effects*; D018258:Herpesvirus 2, Human / Q000187:drug effects*; D020128:Inhibitory Concentration 50; D019906:Nuclear Magnetic Resonance, Biomolecular; D000461:Rhodophyta / Q000737:chemistry*; D013463:Sulfuric Acid Esters / Q000737:chemistry* / Q000494:pharmacology*; D014709:Vero Cells / Q000187:drug effects
D000998:Antiviral Agents; D005685:Galactans; D013463:Sulfuric Acid Esters