Tags

Type your tag names separated by a space and hit enter

Structural analysis and antiviral activity of a sulfated galactan from the red seaweed Schizymenia binderi (Gigartinales, Rhodophyta).
Carbohydr Res. 2005 Oct 31; 340(15):2392-402.CR

Abstract

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.

Authors+Show Affiliations

Matsuhiro 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 AF
No affiliation info available
Damonte EB
No affiliation info available
Kolender AA
No affiliation info available
Matulewicz MC
No affiliation info available
Mejías EG
No affiliation info available
Pujol CA
No affiliation info available
Zúñiga EA
No affiliation info available

MeSH

AlkylationAnimalsAntiviral AgentsCarbohydrate ConformationCell SurvivalChlorocebus aethiopsGalactansHerpesvirus 1, HumanHerpesvirus 2, HumanInhibitory Concentration 50Nuclear Magnetic Resonance, BiomolecularRhodophytaSulfuric Acid EstersVero Cells

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

16125685

Citation

Matsuhiro, Betty, et al. "Structural Analysis and Antiviral Activity of a Sulfated Galactan From the Red Seaweed Schizymenia Binderi (Gigartinales, Rhodophyta)." Carbohydrate Research, vol. 340, no. 15, 2005, pp. 2392-402.
Matsuhiro B, Conte AF, Damonte EB, et al. Structural analysis and antiviral activity of a sulfated galactan from the red seaweed Schizymenia binderi (Gigartinales, Rhodophyta). Carbohydr Res. 2005;340(15):2392-402.
Matsuhiro, B., Conte, A. F., Damonte, E. B., Kolender, A. A., Matulewicz, M. C., Mejías, E. G., Pujol, C. A., & Zúñiga, E. A. (2005). Structural analysis and antiviral activity of a sulfated galactan from the red seaweed Schizymenia binderi (Gigartinales, Rhodophyta). Carbohydrate Research, 340(15), 2392-402.
Matsuhiro B, et al. Structural Analysis and Antiviral Activity of a Sulfated Galactan From the Red Seaweed Schizymenia Binderi (Gigartinales, Rhodophyta). Carbohydr Res. 2005 Oct 31;340(15):2392-402. PubMed PMID: 16125685.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Structural analysis and antiviral activity of a sulfated galactan from the red seaweed Schizymenia binderi (Gigartinales, Rhodophyta). AU - Matsuhiro,Betty, AU - Conte,Ana F, AU - Damonte,Elsa B, AU - Kolender,Adriana A, AU - Matulewicz,María C, AU - Mejías,Enrique G, AU - Pujol,Carlos A, AU - Zúñiga,Elisa A, PY - 2005/06/03/received PY - 2005/08/10/revised PY - 2005/08/11/accepted PY - 2005/8/30/pubmed PY - 2006/1/7/medline PY - 2005/8/30/entrez SP - 2392 EP - 402 JF - Carbohydrate research JO - Carbohydr Res VL - 340 IS - 15 N2 - 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. SN - 0008-6215 UR - https://www.unboundmedicine.com/medline/citation/16125685/Structural_analysis_and_antiviral_activity_of_a_sulfated_galactan_from_the_red_seaweed_Schizymenia_binderi__Gigartinales_Rhodophyta__ DB - PRIME DP - Unbound Medicine ER -