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Fucoidans from the brown seaweed Adenocystis utricularis: extraction methods, antiviral activity and structural studies.
Carbohydr Res. 2003 Jan 20; 338(2):153-65.CR

Abstract

The brown seaweed Adenocystis utricularis (family Adenocystaceae, order Ectocarpales sensu lato) was extracted in parallel with three solvents usually utilized for obtaining fucoidans: distilled water, 2% calcium chloride solution and diluted hydrochloric acid (pH 2) solution. In each case, the extraction was effected at room temperature and then at 70 degrees C. The extraction yields and characteristics of the products were similar in the three cases, with only minor differences. The analytical features of the products indicate that two different types of fucoidans are present in this seaweed. One of them, mostly extracted at room temperature, is composed mainly of L-fucose, D-galactose and ester sulfate (the 'galactofucan'). The other product (the 'uronofucoidan') is the major component of the extracts obtained at 70 degrees C. It is composed mainly of fucose, accompanied by other monosaccharides (mostly Man, but also Glc, Xyl, Rha and Gal), significant amounts of uronic acids and low proportions of sulfate ester. Fractionation with the cationic detergent cetrimide has allowed achieving a better separation of the galactofucan and uronofucoidan components. The galactofucans show a high inhibitory activity against herpes simplex virus 1 and 2, with no cytotoxicity, whereas the uronofucoidans carry no antiviral activity. Structural studies on the galactofucan fractions were carried out by methylation analysis, desulfation and NMR spectroscopy. The fucan constituent is mainly composed of 3-linked alpha-L-fucopyranosyl backbone, mostly sulfated at C-4, and branched at C-2 with non-sulfated fucofuranosyl and fucopyranosyl units, and 2-sulfated fucopyranosyl units. The galactan moiety is more heterogeneous, with predominant D-galactopyranose units linked on C-3 and C-6, and sulfation mostly on C-4, even in terminal non-reducing units. It may be inferred that at least some of these galactose units carry the alpha-configuration.

Authors+Show Affiliations

Ponce NM
Departamento de Química Orgánica-CIHIDECAR, Facultad de Ciencias Exactas y Naturales, Univ. Buenos Aires, Pab.2 Ciudad Universitaria, 1428 Buenos Aires, Argentina.
Pujol CA
No affiliation info available
Damonte EB
No affiliation info available
Flores ML
No affiliation info available
Stortz CA
No affiliation info available

MeSH

AnimalsAntiviral AgentsCell SurvivalChemical FractionationChlorocebus aethiopsHerpesvirus 1, HumanHerpesvirus 2, HumanInhibitory Concentration 50Molecular StructurePolysaccharidesSeaweedVero Cells

Pub Type(s)

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

Language

eng

PubMed ID

12526839

Citation

Ponce, Nora M A., et al. "Fucoidans From the Brown Seaweed Adenocystis Utricularis: Extraction Methods, Antiviral Activity and Structural Studies." Carbohydrate Research, vol. 338, no. 2, 2003, pp. 153-65.
Ponce NM, Pujol CA, Damonte EB, et al. Fucoidans from the brown seaweed Adenocystis utricularis: extraction methods, antiviral activity and structural studies. Carbohydr Res. 2003;338(2):153-65.
Ponce, N. M., Pujol, C. A., Damonte, E. B., Flores, M. L., & Stortz, C. A. (2003). Fucoidans from the brown seaweed Adenocystis utricularis: extraction methods, antiviral activity and structural studies. Carbohydrate Research, 338(2), 153-65.
Ponce NM, et al. Fucoidans From the Brown Seaweed Adenocystis Utricularis: Extraction Methods, Antiviral Activity and Structural Studies. Carbohydr Res. 2003 Jan 20;338(2):153-65. PubMed PMID: 12526839.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Fucoidans from the brown seaweed Adenocystis utricularis: extraction methods, antiviral activity and structural studies. AU - Ponce,Nora M A, AU - Pujol,Carlos A, AU - Damonte,Elsa B, AU - Flores,María L, AU - Stortz,Carlos A, PY - 2003/1/16/pubmed PY - 2003/10/22/medline PY - 2003/1/16/entrez SP - 153 EP - 65 JF - Carbohydrate research JO - Carbohydr Res VL - 338 IS - 2 N2 - The brown seaweed Adenocystis utricularis (family Adenocystaceae, order Ectocarpales sensu lato) was extracted in parallel with three solvents usually utilized for obtaining fucoidans: distilled water, 2% calcium chloride solution and diluted hydrochloric acid (pH 2) solution. In each case, the extraction was effected at room temperature and then at 70 degrees C. The extraction yields and characteristics of the products were similar in the three cases, with only minor differences. The analytical features of the products indicate that two different types of fucoidans are present in this seaweed. One of them, mostly extracted at room temperature, is composed mainly of L-fucose, D-galactose and ester sulfate (the 'galactofucan'). The other product (the 'uronofucoidan') is the major component of the extracts obtained at 70 degrees C. It is composed mainly of fucose, accompanied by other monosaccharides (mostly Man, but also Glc, Xyl, Rha and Gal), significant amounts of uronic acids and low proportions of sulfate ester. Fractionation with the cationic detergent cetrimide has allowed achieving a better separation of the galactofucan and uronofucoidan components. The galactofucans show a high inhibitory activity against herpes simplex virus 1 and 2, with no cytotoxicity, whereas the uronofucoidans carry no antiviral activity. Structural studies on the galactofucan fractions were carried out by methylation analysis, desulfation and NMR spectroscopy. The fucan constituent is mainly composed of 3-linked alpha-L-fucopyranosyl backbone, mostly sulfated at C-4, and branched at C-2 with non-sulfated fucofuranosyl and fucopyranosyl units, and 2-sulfated fucopyranosyl units. The galactan moiety is more heterogeneous, with predominant D-galactopyranose units linked on C-3 and C-6, and sulfation mostly on C-4, even in terminal non-reducing units. It may be inferred that at least some of these galactose units carry the alpha-configuration. SN - 0008-6215 UR - https://www.unboundmedicine.com/medline/citation/12526839/Fucoidans_from_the_brown_seaweed_Adenocystis_utricularis:_extraction_methods_antiviral_activity_and_structural_studies_ DB - PRIME DP - Unbound Medicine ER -