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Fucoidans from the brown seaweed Adenocystis utricularis: extraction methods, antiviral activity and structural studies
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.
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In the citing paper
“A longer extraction time decreases the fucose and sulfate contents, resulting in low-quality fucoidan [23,37].”
From A Review on Fucoidan Structure, Extraction Techniques, and Its Role as an Immunomodulatory Agent (2022) · cites this paper as [37]
In the citing paper
“the galactan moiety, which was also present, was predominantly found to be a backbone structure of (1→3) and (1→6) d-galactopyranose units with sulfation mostly on C-4 [15].”
In the citing paper
“Other algal fucoidans whose structures contain the same α(1→3)-backbone of fucose residues have been found in Analipus japonicas (Ectocarpales), Adenocystis utricularis (Ectocarpales) and Cladosiphon okamuranus (Chordariales) [14,15,39], but the FCSPs from these brown algae also appear to contain other monosaccharides than fucose (Table 2).”
In the citing paper
“Methylation analysis, desulfation and NMR spectroscopy of the FCSPs fractions from Adenocystis utricularis (Ectocarpales) showed that these FCSPs contained the same α-(1→3)-fucopyranose backbone as that found in Chorda filum and Laminaria saccharina FCSPs, and that the fucopyranosyl units were mostly sulfated at C-4, and branched at C-2 with non-sulfated fucopyranosyl units;”
In the citing paper
“Ponce et al. (2003) 17 thus reported that longer extraction time led to poorer fucose content, whereas glucuronic acid increased while sulfate decreased with time, i.e., the sulfate content was highest when glucuronic acid was lowest.17”
From Fucoidans from brown seaweeds: an update on structures, extraction techniques and use of enzymes as tools for structural elucidation (2013) · cites this paper as [17]
In the citing paper
“It has also been shown by others that longer extraction time at higher temperatures led to higher polysaccharide yield with lower amounts of sulfate and a higher proportion of glucuronic acid.11,17”
From Fucoidans from brown seaweeds: an update on structures, extraction techniques and use of enzymes as tools for structural elucidation (2013) · cites this paper as [17]
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Cited by
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Fucoidan: Structure and bioactivity
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Chemical structures and bioactivities of sulfated polysaccharides from marine algae
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Metadata
- Authors
- Ponce, N. M. A., Pujol, C. A., Damonte, E. B., Flores, M. L., & Stortz, C. A.
- Affiliations
- Universidad de Buenos Aires (AR)
- Corresponding author
- Stortz, Carlos A.
- Venue
- Carbohydrate Research
- Publisher
- Elsevier BV
- Published
- 2003-01
- Volume
- 338
- Issue
- 2
- Pages
- 153-165
- ISSN
- 0008-6215 (ISSN-L)
- OpenAlex
- W1981755056
- Cited by
- 484
- References
- 56
- Citations by year
- 2026: 5 · 2025: 21 · 2024: 20 · 2023: 14 · 2022: 40 · 2021: 40 · 2020: 32 · 2019: 23 · 2018: 24 · 2017: 25 · 2016: 18 · 2015: 24 · 2014: 22 · 2013: 23 · 2012: 21
- FWCI
- 11.76
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Carbohydrate Research (publishedVersion)
- PubMed (publishedVersion)
- Topics
- Life Sciences › Agricultural and Biological Sciences › Aquatic Science › Seaweed-derived Bioactive Compounds
- Life Sciences › Agricultural and Biological Sciences › Food Science › Polysaccharides Composition and Applications
- Life Sciences › Agricultural and Biological Sciences › Plant Science › Polysaccharides and Plant Cell Walls
- Keywords
- fucoidan, brown algae, antiviral activity, herpes simplex virus type 1, herpes simplex virus type 2, sulfate esters, uronic acid, extraction methods, sulfated polysaccharides
- MeSH terms
- Animals, Antiviral Agents, Cell Survival, Chlorocebus aethiops, Chemical Fractionation, Polysaccharides, Seaweed, Vero Cells, Molecular Structure, Herpesvirus 2, Human, Herpesvirus 1, Human, Inhibitory Concentration 50
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