The structure of the agaran sulfate from Acanthophora spicifera (Rhodomelaceae, Ceramiales) and its antiviral activity. Relation between structure and antiviral activity in agarans.
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.
Duarte
Maria E R
ME
Departamento de Bioquímica e Biologia Molecular, Universidade Federal do Paraná, P.O. Box 19046, CEP 81531-990, Curitiba, Paraná, Brazil.
Cauduro
Jean P
JP
Noseda
Diego G
DG
Noseda
Miguel D
MD
Gonçalves
Alan G
AG
Pujol
Carlos A
CA
Damonte
Elsa B
EB
Cerezo
Alberto S
AS
D000362:Agar / Q000737:chemistry*; D000818:Animals; D000925:Anticoagulants / Q000737:chemistry / Q000494:pharmacology; D000998:Antiviral Agents / Q000737:chemistry* / Q000494:pharmacology*; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D002470:Cell Survival / Q000187:drug effects; D002522:Chlorocebus aethiops; D002852:Chromatography, Ion Exchange; D020128:Inhibitory Concentration 50; D008969:Molecular Sequence Data; D015394:Molecular Structure; D000461:Rhodophyta / Q000737:chemistry*; D021241:Spectrometry, Mass, Electrospray Ionization; D013329:Structure-Activity Relationship; D013431:Sulfates / Q000737:chemistry* / Q000494:pharmacology*; D014709:Vero Cells; D010948:Viral Plaque Assay
D000925:Anticoagulants; D000998:Antiviral Agents; D013431:Sulfates; D000362:Agar