Chemical structure and antiviral activity of the sulfated heterorhamnan isolated from the green seaweed Gayralia oxysperma.
A homogeneous sulfated heterorhamnan was obtained by aqueous extraction, then by ultrafiltration from the green seaweed Gayralia oxysperma. Besides alpha-L-rhamnose it contains glucuronic and galacturonic acids, xylose and glucose. The structure was established by methylation analyses of the carboxyl-reduced, carboxyl-reduced/desulfated, carboxyl-reduced/Smith-degraded, and carboxyl-reduced/Smith-degraded/desulfated products and 1D, 2D NMR spectroscopy analyses. The heterorhamnan backbone is constituted by 3- and 2-linked rhamnosyl units (1.00:0.80), the latter being approximately 50% substituted at C-3 by side chains containing 2-sulfated glucuronic and galacturonic acids and xylosyl units. The 3- and 2-linked rhamnosyl units are unsulfated (20%), disulfated (16%), and mostly monosulfated at C-2 (27%) and C-4 (37%). The branched and sulfated heterorhamnan had high and specific activity against herpes simplex virus.
Departamento de Bioquímica e Biologia Molecular, Universidade Federal do Paraná, Curitiba, Paraná, Brazil.
Juliana E F
JE
Cassolato
Miguel D
MD
Noseda
Carlos A
CA
Pujol
Franciane M
FM
Pellizzari
Elsa B
EB
Damonte
Maria E R
ME
Duarte
D000818:Animals; D000998:Antiviral Agents / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology* / Q000633:toxicity; D002245:Carbon Dioxide / Q000737:chemistry; D002470:Cell Survival / Q000187:drug effects; D002522:Chlorocebus aethiops; D000460:Chlorophyta / Q000737:chemistry*; D003837:Deoxy Sugars / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology* / Q000633:toxicity; D018259:Herpesvirus 1, Human / Q000187:drug effects; D018258:Herpesvirus 2, Human / Q000187:drug effects; D009682:Magnetic Resonance Spectroscopy; D008351:Mannans / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology* / Q000633:toxicity; D008745:Methylation; D010084:Oxidation-Reduction; D012995:Solubility; D017550:Spectroscopy, Fourier Transform Infrared; D013463:Sulfuric Acid Esters / Q000737:chemistry*; D014709:Vero Cells; D014867:Water / Q000737:chemistry
D000998:Antiviral Agents; D003837:Deoxy Sugars; D008351:Mannans; D013463:Sulfuric Acid Esters; D014867:Water; C065836:rhamnan; D002245:Carbon Dioxide; C041069:carboxyl radical