Next Article in Journal
Anti-Inflammatory and Antioxidant Properties of Malapterurus electricus Skin Fish Methanolic Extract in Arthritic Rats: Therapeutic and Protective Effects
Next Article in Special Issue
New Ceramides and Cerebrosides from the Deep-Sea Far Eastern Starfish Ceramaster patagonicus
Previous Article in Journal
An Aminopyrimidone and Aminoimidazoles Alkaloids from the Rodrigues Calcareous Marine Sponge Ernsta naturalis
Previous Article in Special Issue
1-O-Alkylglycerol Ethers from the Marine Sponge Guitarra abbotti and Their Cytotoxic Activity
 
 
Search for Articles:
Title / Keyword
Author / Affiliation / Email
Journal
Article Type
 
 
Advanced Search
 
Section
Special Issue
Volume
Issue
Number
Page
 
Journals
Marine Drugs
Volume 20
Issue 10
10.3390/md20100638
marinedrugs-logo
Submit to this Journal Review for this Journal Propose a Special Issue
► Article Menu

Article Menu

share Share announcement Help format_quote Cite question_answer Discuss in SciProfiles thumb_up
...
Endorse textsms
...
Comment
first_page
settings
Order Article Reprints
Font Type:
Arial Georgia Verdana
Font Size:
Aa Aa Aa
Line Spacing:
Column Width:
Background:
Commentary

Fucoidans of Brown Algae: Comparison of Sulfated Polysaccharides from Fucus vesiculosus and Ascophyllum nodosum

by
Anatolii I. Usov
*,
Maria I. Bilan
,
Nadezhda E. Ustyuzhanina
and
Nikolay E. Nifantiev
*
The Laboratory of Glycoconjugate Chemistry, N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect 47, 119991 Moscow, Russia
*
Authors to whom correspondence should be addressed.
Mar. Drugs 2022, 20(10), 638; https://doi.org/10.3390/md20100638
Submission received: 26 August 2022 / Revised: 10 October 2022 / Accepted: 11 October 2022 / Published: 13 October 2022
(This article belongs to the Special Issue Honoring Prof. Dr. Valentin A. Stonik for His Outstanding Contribution to Marine Natural Product Chemistry on the Occasion of His 80th Birthday)
Browse Figure
Versions Notes

Abstract

:
Preparations of sulfated polysaccharides obtained from brown algae are known as fucoidans. These biopolymers have attracted considerable attention due to many biological activities which may find practical applications. Two Atlantic representatives of Phaeophyceae, namely, Fucus vesiculosus and Ascophyllum nodosum, belonging to the same order Fucales, are popular sources of commercial fucoidans, which often regarded as very similar in chemical composition and biological actions. Nevertheless, these two fucoidan preparations are polysaccharide mixtures which differ considerably in amount and chemical nature of components, and hence, this circumstance should be taken into account in the investigation of their biological properties and structure–activity relationships. In spite of these differences, fractions with carefully characterized structures prepared from both fucoidans may have valuable applications in drug development.

1. Introduction

Sulfated polysaccharides containing L-fucose as the main monosaccharide component were discovered in several brown algae, including Fucus vesiculosus and Ascophyllum nodosum, more than a century ago [1]. Now, it is well known that preparations obtained by extraction of algae and designated by trivial name “fucoidans” usually represent complex mixtures of several chemically different polysaccharides [2,3,4], where fucan sulfate (FS, a polysaccharide built up of fucose and sulfate only) may (but not necessarily) be one of the main components. The procedure suitable for commercial production of fucoidans from brown algal biomass was suggested in 1952 [5], but a highly purified sample of more or less individual FS was obtained much later by numerous manipulations with crude fucoidan from F. vesiculosus, probably accompanied by considerable loss of the starting material [6]. The first data on the chemical structure of SF published in 1950 [7,8] were then revised several times. In this period, evidence appeared on the prospective biological activity of fucoidans, especially as anticoagulants [9,10].
The availability of commercial fucoidans resulted in the rapid appearance of a large amount of publications devoted mainly to the investigation of their biological properties [11]. At present, there are hundreds of such papers; for example, more than 400 references dedicated mainly to therapeutic applications of fucoidans were cited in three reviews by Fitton et al. [12,13,14]. Multiple biological actions of fucoidans depend primarily on their interaction with different proteins due to the presence of sulfate groups [15,16,17,18,19], but branching of molecules [20] and molecular weights [21,22] may also be very important factors. Fucoidans are traditionally regarded as promising anticoagulant [23,24,25,26], antitumor [27,28] and anti-inflammatory agents [29,30,31,32,33], but recently they acquired special importance as potential components of antiviral drugs [34,35,36], activators of hematopoiesis [37,38], and reagents for use in nanomedicine [39].
The elucidation of correlations between the biological properties of concrete samples of fucoidans and their chemical structures remains a very important task [23,40], but there are substantial difficulties connected with the conception of “fucoidan”, which is not the term of strict carbohydrate nomenclature. It designates a preparation of water-soluble sulfated polysaccharides, obtained by extraction of brown algal biomass and separated (partially or completely) from other polysaccharide components of this biomass devoid of sulfate groups—alginates and laminarans. The class Phaeophyceae (brown algae) numbers more than 1000 species, which may differ considerably in their polysaccharide composition [41,42]. Thus, fucoidans isolated from different species may contain not only fucopyranose, but also fucofuranose units [43] together with other monosaccharides, such as galactose, xylose, mannose, and glucuronic acid, etc. [2,3,4,41].
Therefore, the algal species is the first factor determining the composition of extracted sulfated polysaccharides. Then it is necessary to bear in mind that representatives of the same species growing in different conditions should inevitably differ in chemical composition. Ecological factors influencing the chemical composition of biomass include age and physiological status of the alga [44], climate and season [45], water temperature and salinity, solar radiation, and the accessibility of biogenic elements. Additional influences on the quality of polysaccharide preparations should have the procedures of harvesting and storage of raw material, as well as conditions of biomass treatment, which should secure the completeness of polysaccharide extraction without their degradation and minimal dissolution of extraneous non-carbohydrate materials, such as proteins and polyphenols. Since crude preparations of sulfated polysaccharides, obtained by water extraction, are usually mixtures of biopolymers of different structures [46], the nature of products destined for structural analysis or the investigation of biological properties will be determined by the used methods of fractionation [47]. Taking into account all the factors listed above, it is not surprising that different groups of researchers, dealing with samples being commonly named by the same term “fucoidan”, in fact are often working with very different polysaccharides [48].
Below we overview the published results of structural studies of polysaccharides obtained from two widely distributed brown algal species, namely, F. vesiculosus and A. nodosum. Both these species have been investigated for a long time and may be regarded as prospective sources for the large-scale preparation of sulfated polysaccharides suitable for diverse medical applications [49]. For example, based on such polysaccharides, biological vectors are being developed, which may be used for delivering drugs or diagnostic contrasting agents to tissues with increased P-selectin expression [50,51,52,53,54]. It should be emphasized that GMP-graded production of low-molecular-weight fucoidan from A. nodosum was recently reported [54], and it was suggested to apply this product as the biovector or contraster for the detection of P-selectin expression during cardiovascular diseases.

2. Sulfated Polysaccharides of Fucus vesiculosus

Representatives of the genus Fucus are widely distributed in the North Atlantic, as well in the Barents and the Whyte Seas. Being typical littoral species, they occupy spacious coastal plots uncovering at the low tide. Harvesting of this natural raw material is not a very difficult task.
F. vesiculosus was one of those several brown algal species wherein the presence of fucoidans was discovered [1]. Polysaccharide preparation from this species was used in the first attempt to elucidate its chemical structure [7,8]. The alga was heated with water in the boiling water bath, the extract obtained was treated with lead acetate to remove alginic acid and proteins, and the remaining soluble polysaccharides were reprecipitated several times and yielded a preparation, which was regarded as a fucan sulfate. According to the analytical data, an essentially linear structure was suggested for the backbone of this polysaccharide, built up of 1→2-linked α-L-fucopyranose residues, together with some unsubstituted or monosulfated fucose residues attached to position 3 of the backbone as single branches.
About 40 years later, a commercial fucoidan from F. vesiculosus was reinvestigated and the structure of hypothesized fucan sulfate was corrected [55]. It was shown that 1→3-linkage is the main type of linkage between the backbone residues. Possible positions of sulfate and branches are depicted in Figure 1. Similar figures are often used to illustrate structures of FS isolated from other brown algal species [56]. It should be noted that this formula does not belong to any concrete sample of FS, but shows only the set of different units, which may be found in different proportions in different samples of polysaccharides.
The structure of the backbone was revised once more after the introduction of NMR spectroscopy in the practice of structural analysis of FS. Spectral data gave reliable confirmation on the presence of 1→3-linked backbone in FS isolated from Chorda filum [57] and several other algae belonging to the order Laminariales, but showed that fucoidans from F. vesiculosus and A. nodosum contain fractions with backbones built up of alternating (1→3)- and (1→4)-linked fucose residues [58,59]. Polysaccharides containing two alternating linkages in the backbones were also found in several other representatives of the order Fucales [60,61,62]. A hypothesis once appeared that (1→3)-linked FS backbones are characteristic for algae from Laminariales only, whereas backbones with alternating (1→3)- and (1→4)-linkages are typical for algae from Fucales, but the existence of such a firm correlation between the taxonomic position of the algae and the structure of their FS was not confirmed in recent investigations [48].
The formula of FS depicted in Figure 1 does not take into account the presence of several other monosaccharides, primarily galactose, xylose, mannose, and glucuronic acid, which usually may be found in fucoidan preparations. These monosaccharides may be components of other types of polysaccharides. According to contemporary evidence, several polysaccharides forming brown algal cell walls are linked with proteins and polyphenols in a complex [4], where the nature of linkages between components remains mostly unknown. To isolate polysaccharides, this complex should be destroyed by, for example, the action of dilute acids [5], although FS itself may be partially degraded under acid conditions. Crude fucoidans usually contain a wide set of molecules differing in composition and molecular weights and evidently need additional purification. Anion-exchange chromatography demonstrates the presence of continuous spectrum of molecules differing in charge and monosaccharide composition, from fractions with low sulfate and low fucose, containing other neutral monosaccharides and glucuronic acid, to highly sulfated fucans [63]. Simultaneous presence of several different sulfated polysaccharides was demonstrated for many brown algae [46,64]. The isolation of the components of these mixtures depends on their relative content and specific extraction and fractionation procedures. More detailed discussion on the problem is given below in the description of polysaccharides from A. nodosum.
One of the laboratory procedures of fucoidan isolation [60] recommends extraction of algal biomass with 2% aqueous calcium chloride at 85 °C. It results in dissolution of neutral laminaran and sulfated polysaccharides, whereas insoluble Ca-salts of alginic acids remain in the precipitate. Acid polysaccharides may be precipitated from extract by the addition of a cationic detergent, such as cetyltrimethylammonium bromide, transformed into the soluble sodium salts and then chromatographed on an anion-exchanger, such as DEAE-Sephacel, using stepwise elution with NaCl solutions of increasing concentrations. Neutral components are not absorbed on the column, while alginic acids are eluted with 0.5 M NaCl, and sulfated fractions are then eluted according to the increase of sulfate content, the most sulfated fractions appearing in the region of 2.0 M NaCl.
There are numerous modifications of isolation procedure aimed at acceleration of the process or increase of the yield of target polysaccharides. For these purposes it was suggested to isolate cell walls [64,65], to carry out extraction with solutions of acids, alkali, or detergents [64,66,67], to use autohydrolysis [68], microwave radiation [69], ultrasound [70], or treatment with enzymes capable of destroying the accompanying polysaccharides [71,72]. Fucoidans prepared by different procedures may differ considerably in composition and properties. Thus, seventeen fucoidans isolated by different authors from F. vesiculosus contain from 4% to 39% of sulfate and from 50% to 94% of fucose in carbohydrate moiety. These analytical characteristics were given in a recent review [48].

3. Sulfated Polysaccharides of Ascophyllum nodosum

This brown algal species belonging to the same family Fucaceae, as described above F. vesiculosus, practically coincides with it in geographical distribution, but is growing in sublittoral conditions. A. nodosum is used for industrial production of alginates and is available as feedstock in large amounts.
A peculiar sulfated heteropolysaccharide named “ascophyllan” was isolated from the mixture of water-soluble polysaccharides obtained by extraction of A. nodosum [73]. It contained approximately equimolar amounts of fucose, xylose, glucuronic acid, and sulfate, as well as a tightly bound polypeptide fragment. Partial acid hydrolysis of ascophyllan gave rise to 3-O-β-D-xylopyranosyl-L-fucose [74] and a non-dialysable polyuronide, indicating the presence of a backbone built up of glucuronic acid residues and side chains containing fucose and xylose. Using extractions under very mild conditions, it was possible to isolate a high-molecular complex, which was split under subsequent acid treatment into ascophyllan, alginate, and a fraction close to fucan sulfate in composition. Based on these data, it was supposed that a similar situation should also be found for polysaccharides of F. vesiculosus, but in this case the content of fucan sulfate predominates considerably over the content of hypothetical ascophyllan analogue [75]. Structural analysis of ascophyllan was the subject of a series of more recent publications [76,77,78,79,80,81]. Based on these data, a procedure was developed for isolation of a fraction of fucan sulfate from A. nodosum, having backbones of 1,3-linked fucose residues [82]. At the same time another fraction, containing backbones of alternating 1,3-1,4-linked fucose residues, was obtained from the same alga by another group of authors. The structure of the latter polysaccharide was carefully investigated using chemical methods together with NMR spectroscopy [58,59] and mass spectrometry [83]. Hence, fucan sulfate itself is heterogeneous and contains fractions having fundamental structural differences in their carbohydrate moieties.
Later on, a simplified procedure of biomass treatment was published, which gives the possibility to prepare ascophyllan and fucan sulfate separately [84] (Table 1). Polysaccharides isolated by this procedure were studied in biological tests, and it was found for the first time that ascophyllan can stimulate the growth of a culture of mammalian cells (under the same conditions fucan sulfate showed opposite action) [85]. Comparison of polysaccharide preparations, isolated from A. nodosum by usual extraction with dilute acid, and by several new procedures using microwave radiation [86], ultrasound, or enzymatic degradation of cell walls was described in a recent paper [87]. As expected, these preparations differ in yields, composition, and molecular weights, but have comparable prebiotic activity by stimulating, in vitro, the growth of lactic acid bacteria. Two polysaccharide samples differing in molecular weights and capable of inhibiting inflammation were isolated by treatment of A. nodosum with enzymes followed by anion-exchange chromatography [88]. Both preparations contained not only fucose, but also galactose and hence were fragments of a sulfated galactofucan. They exhibited different anti-inflammatory activities, indicating that molecular weight is an important factor for this type of biological action.

4. Conclusions

Both brown algal species described in this review are convenient sources of so-called “fucoidans”, which are crude mixtures of sulfated polysaccharides. Both “fucoidans” contain fucan sulfates as the main components, which are especially interesting as biologically active polysaccharides. Differences between “fucoidans” of these two algal species are connected mainly with the higher content of another main component, termed “ascophyllan”, in A. nodosum. In fact, ascophyllan itself is a mixture of several heteropolysaccharides of moderate sulfation degree, containing, in addition to fucose, also xylose, glucuronic acid, and some other monosaccharides [73,77,81]. Ascophyllan has its own practically useful properties and may find application as a preparation with peculiar (distinct from fucan sulfates) biological activities [89]. The paper by W. Jin et al. [90] may be mentioned as a very impressive example of investigation devoted to correlating the biological activity and chemical structures of fucoidan components: the authors carefully analyzed the structural information of about sixty fucoidan samples isolated from different algae, used them in a cell surface tau-binding assay, and found that two different branched sulfated polysaccharide components of fucoidans, namely, a galactofucan and a fucoglucuronomannan, acted as effective inhibitors of tau spreading. Hence, these data may provide a basis for creation of drugs applicable for therapy in the earliest phase of Alzheimer’s disease.
Resolution of “fucoidans” into individual polysaccharide components remains the most difficult problem. Since these polysaccharides are polyanions, anion-exchange chromatography is traditionally used for their separation, giving excellent results in some cases [61]. At the same time this procedure cannot resolve compounds differing in structure, but having similar charge densities. Similar limitations are typical for gel-permeation chromatography, where even structurally different polysaccharides cannot be resolved, if they have close molecular weights. Evidently, the resolution of fucoidans needs additional improvement. Specific enzymatic degradation of unnecessary components of the mixture [91] or affinity chromatography based on the property of sulfated polysaccharides to bind several proteins [92,93] may be mentioned as the possible approaches to new fractionation procedures.
Fucoidan preparations devoted to medical applications should satisfy the very strong demands concerning their reproducible composition and compatibility with manufacturing requirements under GMP-standards. A similar problem has been solved in the preparation of low-molecular-weight heparins [94]. The process of fucoidan isolation should be carefully controlled at several steps. One of the most important parameters is the standard quality of the raw material, which is highly varying and depending on the place and season of harvesting, as well on the procedure of its conservation and storage. Extraction may be carried out with dilute acids under moderate heating at the conditions, which are sufficient for the destruction of polysaccharide complexes of the cell walls without marked degradation of the target fucoidan. Mild oxidants may be used for bleaching, and high molecular mass may be diminished (if necessary) by careful partial depolymerization. The wanted fraction may be prepared using membrane filtration. Finally (this is especially important for algae similar in polysaccharide composition to A. nodosum) the most interesting biologically active highly sulfated fraction should be separated from lower-sulfated material (such as so-called ascophyllan) using chromatography on anion-exchange resins. The preparations obtained should be characterized by quantitative determination of monosaccharides (e.g., gas–liquid chromatography, spectrophotometry) sulfate (e.g., turbidimetry) and molecular-mass distribution (e.g., analytical gel-permeation chromatography). Similar standardization procedures are suggested for sulfated glycosaminoglycans, such as, for example, for chondroitin sulfates [95].
Regulatory requirements mentioned above shorten the fields of medical use of fucoidans by the case of superficial applications (ointments, gels, inhalable compositions, etc.), but injectable forms may be based on synthetic oligosaccharides related to fucoidan fragments. It should be emphasized that the preparation of such compounds is well elaborated to date [96,97,98]. In addition, one promising option for fucoidan standardization can be connected with enzymatic treatments. Recent studies discovered a series of fucoidan degrading and modifying enzymes [99,100,101], but up to now only a few agents of this type were obtained, while their applicability for industrial application was not studied yet and needs to be investigated.

Author Contributions

Conceptualization, A.I.U. and N.E.N.; resources, M.I.B. and N.E.U.; writing—original draft preparation, A.I.U.; writing—review and editing, N.E.N. and M.I.B.; supervision, N.E.N.; project administration, N.E.N.; funding acquisition, N.E.N. All authors have read and agreed to the published version of the manuscript.

Funding

This research was funded by the Ministry of Science and Higher Education of Russia (Grant Agreement No. 075-15-2020-792).

Data Availability Statement

Data are available from the corresponding author.

Conflicts of Interest

The authors declare no conflict of interest.

References

  1. Kylin, H. Zur Biochemie der Meeresalgen. Hoppe-Seyler’s Z. Physiol. Chem. 1913, 83, 171–197. [Google Scholar] [CrossRef]
  2. Usov, A.I.; Bilan, M.I. Fucoidans—sulfated polysaccharides of brown algae. Russ. Chem. Revs 2009, 78, 846–862. [Google Scholar] [CrossRef]
  3. Ale, M.T.; Meyer, A.S. Fucoidans from brown seaweeds: An update on structures, extraction techniques and use of enzymes as tools for structural elucidation. RSC Advances 2013, 3, 8131–8141. [Google Scholar] [CrossRef] [Green Version]
  4. Deniaud-Bouët, E.; Hardouin, K.; Potin, P.; Kloareg, B.; Hervé, C. A review about brown algal cell walls and fucose-containing sulfated polysaccharides: Cell wall context, biomedical properties and key research challenges. Carbohydr. Polym. 2017, 175, 395–408. [Google Scholar] [CrossRef]
  5. Black, W.A.P.; Dewar, E.T.; Woodward, F.N. Manufacture of algal chemicals. IV. Laboratory scale isolation of fucoidin from brown marine algae. J. Sci. Food Agric. 1952, 3, 122–129. [Google Scholar] [CrossRef]
  6. Bernardi, G.; Springer, G.F. Properties of highly purified fucan. J. Biol. Chem. 1962, 237, 75–80. [Google Scholar] [CrossRef]
  7. Percival, E.G.V.; Ross, A.G. Fucoidin. Part I. The isolation and purification of fucoidin from brown seaweeds. J. Chem. Soc. 1950, 717–720. [Google Scholar] [CrossRef]
  8. Conchie, J.; Percival, E.G.V. Fucoidin. Part II. The hydrolysis of a methylated fucoidin prepared from Fucus vesiculosus. J. Chem. Soc. 1950, 827–832. [Google Scholar] [CrossRef]
  9. Springer, G.F.; Wurzel, H.A.; McNeal, G.M., Jr.; Ansell, N.J.; Doughty, M.F. Isolation of anticoagulant fractions from crude fucoidin. Proc. Soc. Exptl. Biol. Med. 1957, 94, 404–409. [Google Scholar] [CrossRef]
  10. Church, F.C.; Meade, J.B.; Treanor, R.E.; Whinna, H.C. Antithrombin activity of fucoidan. The interaction of fucoidan with heparin cofactor II, antithrombin III, and thrombin. J. Biol. Chem. 1989, 264, 3618–3623. [Google Scholar] [CrossRef]
  11. Berteau, O.; Mulloy, B. Sulfated fucans, fresh perspectives: Structures, functions, and biological properties of sulfated fucans and an overview of enzymes active toward this class of polysaccharide. Glycobiology 2003, 13, 29R–40R. [Google Scholar] [CrossRef] [PubMed] [Green Version]
  12. Fitton, J.H. Therapies from fucoidan; multifunctional marine polymers. Mar. Drugs 2011, 9, 1731–1760. [Google Scholar] [CrossRef] [PubMed] [Green Version]
  13. Fitton, J.H.; Stringer, D.N.; Karpiniec, S.S. Therapies from fucoidan: An update. Mar. Drugs 2015, 13, 5920–5946. [Google Scholar] [CrossRef] [PubMed] [Green Version]
  14. Fitton, J.H.; Stringer, D.N.; Park, A.Y.; Karpiniec, S.S. Therapies from fucoidan: New developments. Mar. Drugs 2019, 17, 571. [Google Scholar] [CrossRef] [Green Version]
  15. Luthuli, S.; Wu, S.; Cheng, Y.; Zheng, X.; Wu, M.; Tong, H. Therapeutic effects of fucoidan: A review on recent studies. Mar. Drugs 2019, 17, 487. [Google Scholar] [CrossRef] [Green Version]
  16. Kang, J.; Jia, X.; Wang, N.; Xiao, M.; Song, S.; Wu, S.; Li, Z.; Wang, S.; Cui, S.W.; Guo, Q. Insights into the-structure-bioactivity relationships of marine sulfated polysaccharides: A review. Food Hydrocolloids 2022, 123, 107049. [Google Scholar] [CrossRef]
  17. Haroun-Bouhedja, F.; Ellouali, M.; Sinquin, C.; Boisson-Vidal, C. Relationship between sulfate groups and biological activities of fucans. Thromb. Res. 2000, 100, 453–459. [Google Scholar] [CrossRef]
  18. Koyanagi, S.; Tanigawa, N.; Nakagawa, H.; Soeda, S.; Shimeno, H. Oversulfation of fucoidan enhances its anti-angiogenic and antitumor activities. Biochem. Pharmacol. 2003, 65, 173–179. [Google Scholar] [CrossRef]
  19. Qiu, X.; Amarasekara, A.; Doctor, V. Effect of oversulfation on the chemical and biological properties of fucoidan. Carbohydr. Polym. 2006, 63, 224–228. [Google Scholar] [CrossRef]
  20. Clément, M.-J.; Tissot, B.; Chevolot, L.; Adjadj, E. Du, Y.; Curmi, P.A.; Daniel, R. NMR characterization and molecular modeling of fucoidan showing the importance of oligosaccharide branching in its anticomplementary activity. Glycobiology 2010, 20, 883–894. [Google Scholar] [CrossRef]
  21. Lahrsen, E.; Liewert, I.; Alban, S. Gradual degradation of fucoidan from Fucus vesiculosus and its effect on structure, antioxidant and antiproliferative activities. Carbohydr. Polym. 2018, 192, 208–216. [Google Scholar] [CrossRef] [PubMed]
  22. Cabral, E.M.; Mondala, J.R.M.; Oliveira, M.; Przyborska, J.; Fitzpatrick, S.; Rai, D.K.; Sivagnanam, S.P.; Garcia-Vaquero, M.; O’Shea, D.; Devereux, M.; et al. Influence of molecular weight fractionation on the antimicrobial and anticancer properties of a fucoidan rich-extract from the macroalgae Fucus vesiculosus. Int. J. Biol. Macromol. 2021, 186, 994–1002. [Google Scholar] [CrossRef] [PubMed]
  23. Cumashi, A.; Ushakova, N.A.; Preobrazhenskaya, M.E.; D’Incecco, A.; Piccoli, A.; Totani, L.; Tinari, N.; Morozevich, G.E.; Berman, A.E.; Bilan, M.I.; et al. A comparative study of the antiinflammatory, anticoagulant, antiangiogenic and antiadhesive activities of nine different fucoidans from brown seaweeds. Glycobiology 2007, 17, 541–552. [Google Scholar] [CrossRef] [PubMed] [Green Version]
  24. Ustyuzhanina, N.E.; Ushakova, N.A.; Zyuzina, K.A.; Bilan, M.I.; Elizarova, A.L.; Somonova, O.V.; Madzhuga, A.V.; Krylov, V.B.; Preobrazhenskaya, M.E.; Usov, A.I.; et al. Influence of fucoidans on hemostatic system. Mar. Drugs 2013, 11, 2444–2458. [Google Scholar] [CrossRef] [PubMed] [Green Version]
  25. Ustyuzhanina, N.E.; Ushakova, N.A.; Preobrazhenskaya, M.E.; Bilan, M.I.; Tsvetkova, E.A.; Krylov, V.B.; Anisimova, N.A.; Kiselevskiy, M.V.; Krukovskaya, N.V.; Li, C.; et al. Fucoidans as a platform for new anticoagulant drugs discovery. Pure Appl. Chem. 2014, 86, 1365–1375. [Google Scholar] [CrossRef]
  26. Mourão, P.A.S. Perspective on the use of sulfated polysaccharides from marine organisms as a source of new antithrombotic drugs. Mar. Drugs 2015, 13, 2770–2784. [Google Scholar] [CrossRef] [Green Version]
  27. Atashrazm, F.; Lowenthal, R.M.; Woods, G.M.; Holloway, A.F.; Dickinson, J.L. Fucoidan and cancer: A multifunctional molecule with anti-tumor potential. Mar. Drugs 2015, 13, 2327–2346. [Google Scholar] [CrossRef] [Green Version]
  28. van Weelden, G.; Bobinski, M.; Jkla, K.; van Weelden, W.J.; Romano, A.; Pijnenborg, J.M.A. Fucoidan structure and activity in relation to anti-cancer mechanisms. Mar. Drugs 2019, 17, 32. [Google Scholar] [CrossRef] [Green Version]
  29. Preobrazhenskaya, M.E.; Berman, A.E.; Mikhailov, V.I.; Ushakova, N.A.; Mazurov, A.V.; Semenov, A.V.; Usov, A.I.; Nifant’ev, N.E.; Bovin, N.V. Fucoidan inhibits leucocyte recruitment in a model peritoneal inflammation in rat and blocks interaction of P-selectin with its carbohydrate ligand. Biochem. Mol. Biol. Int. 1997, 43, 443–451. [Google Scholar] [CrossRef]
  30. Phull, A.R.; Kim, S.J. Fucoidan as bio-functional molecule: Insight into the anti-inflammatory potential and associated molecular mechanisms. J. Func. Food. 2017, 38, 415–426. [Google Scholar] [CrossRef]
  31. Apostolova, E.; Lukova, P.; Baldzhieva, A.; Katsarov, P.; Nikolova, M.; Iliev, I.; Peychev, L.; Trica, B.; Oancea, F.; Delattre, C.; et al. Immunomodulatory and anti-inflammatory effects of fucoidan: A review. Polymers 2020, 123, 107049. [Google Scholar] [CrossRef] [PubMed]
  32. Fonseca, R.J.C.; Mourão, P.A.S. Pharmacological activities of sulfated fucose-rich polysaccharides after oral administration: Perspectives for the development of new carbohydrate-based drugs. Mar. Drugs 2021, 19, 425. [Google Scholar] [CrossRef] [PubMed]
  33. Yang, J.-Y.; Lim, S.Y. Fucoidans and bowel health. Mar. Drugs 2021, 19, 436. [Google Scholar] [CrossRef]
  34. Fitton, J.H.; Park, A.Y.; Karpiniec, S.S.; Stringer, D.N. Fucoidan and lung function: Value in viral infection. Mar. Drugs 2021, 19, 4. [Google Scholar] [CrossRef] [PubMed]
  35. Lomartire, S.; Gonçalves, A.M.M. Antiviral activity and mechanisms of seaweeds bioactive compounds on enveloped viruses—A review. Mar. Drugs 2022, 20, 385. [Google Scholar] [CrossRef]
  36. Pradhan, B.; Nayak, R.; Patra, S.; Bhuyan, P.P.; Behera, P.K.; Mandal, A.K.; Behera, C.; Ki, J.-S.; Adhikary, S.P.; MubarakAli, D.; et al. A state-of-the-art review on fucoidan as an antiviral agent to combat viral infections. Carbohydr. Polym. 2022, 291, 119551. [Google Scholar] [CrossRef]
  37. Anisimova, N.; Ustyuzhanina, N.; Bilan, M.; Donenko, F.; Usov, A.; Kiselevskiy, M.; Nifantiev, N. Fucoidan and fucosylated chondroitin sulfate stimulate hematopoiesis in cyclophosphamide-induced mice. Mar. Drugs 2017, 15, 301. [Google Scholar] [CrossRef] [Green Version]
  38. Anisimova, N.Y.; Ustyuzhanina, N.E.; Bilan, M.I.; Donenko, F.V.; Ushakova, N.A.; Usov, A.I.; Kiselevskiy, M.V.; Nifantiev, N.E. Influence of modified fucoidan and related sulfated oligosaccharides on hematopoiesis in cyclophosphamide-induced mice. Mar. Drugs 2018, 16, 333. [Google Scholar] [CrossRef] [Green Version]
  39. Chollet, L.; Saboural, P.; Chauvierre, C.; Villemin, J.-N.; Letourneur, D.; Chaubet, F. Fucoidans in nanomedicine. Mar. Drugs 2016, 14, 145. [Google Scholar] [CrossRef] [Green Version]
  40. Croci, D.O.; Cumashi, A.; Ushakova, N.A.; Preobrazhenskaya, M.E.; Piccoli, A.; Totani, L.; Ustyuzhanina, N.E.; Bilan, M.I.; Usov, A.I.; Grachev, A.A.; et al. Fucans, but not fucomannoglucuronans, determine the biological activities of sulfated polysaccharides from Laminaria saccharina brown seaweed. PLoS ONE 2011, 6, e17283. [Google Scholar] [CrossRef]
  41. Ale, M.T.; Mikkelsen, J.D.; Meyer, A.S. Important determinants for fucoidan bioactivity: A critical review of structure-function relations and extraction methods for fucose-containing sulfated polysaccharides from brown seaweeds. Mar. Drugs 2011, 9, 2106–2130. [Google Scholar] [CrossRef] [PubMed] [Green Version]
  42. Usov, A.I.; Smirnova, G.P.; Klochkova, N.G. Polysaccharides of algae. 55. Polysaccharide composition of several brown algae from Kamchatka. Russ. J. Bioorg. Chem. 2001, 27, 395–399. [Google Scholar] [CrossRef] [PubMed]
  43. Bilan, M.I.; Vinogradova, E.V.; Tsvetkova, E.A.; Grachev, A.A.; Shashkov, A.S.; Nifantiev, N.E.; Usov, A.I. A sulfated glucuronofucan containing both fucofuranose and fucopyranose residues from the brown alga Chordaria flagelliformis. Carbohydr. Res. 2008, 343, 2605–2612. [Google Scholar] [CrossRef] [PubMed]
  44. Skriptsova, A.V.; Shevchenko, N.M.; Tarbeeva, D.V.; Zvyagintseva, T.N. Comparative study of polysaccharides from reproductive and sterile tissues of five brown seaweeds. Mar. Biotechnol. 2012, 14, 304–311. [Google Scholar] [CrossRef]
  45. Skriptsova, A.V.; Shevchenko, N.M.; Zvyagintseva, T.N.; Imbs, T.I. Monthly changes in the content and monosaccharide composition of fucoidan from Undaria pinnatifida (Laminariales, Phaeophyta). J. Appl. Phycol. 2010, 22, 79–86. [Google Scholar] [CrossRef]
  46. Bilan, M.I.; Grachev, A.A.; Shashkov, A.S.; Kelly, M.; Sanderson, C.J.; Nifantiev, N.E.; Usov, A.I. Further studies on the composition and structure of a fucoidan preparation from the brown alga Saccharina latissima. Carbohydr. Res. 2010, 345, 2038–2047. [Google Scholar] [CrossRef]
  47. Sichert, A.; Le Gall, S.; Klau, L.J.; Laillet, B.; Rogniaux, H.; Aachmann, F.L.; Hehemann, J.-H. Ion-exchange purification and structural characterization of five sulfated fucoidans from brown algae. Glycobiology 2021, 31, 352–357. [Google Scholar] [CrossRef]
  48. Ponce, N.M.A.; Stortz, C.A. A comprehensive and comparative analysis of the fucoidan compositional data across the Phaeophyceae. Front. Plant Sci. 2020, 11, 556312. [Google Scholar] [CrossRef]
  49. Keleszade, E.; Patterson, M.; Trangmar, S.; Guinan, K.J.; Costabile, A. Clinical efficacy of brown seaweeds Ascophyllum nodosum and Fucus vesiculosus in the prevention or delay progression of the metabolic syndrome: A review of clinical trials. Molecules 2021, 26, 714. [Google Scholar] [CrossRef]
  50. Dellaquila, A.; Le Bao, C.; Letourneur, D.; Simon-Yarza, T. In vitro strategies to vascularize 3D physiologically relevant models. Adv. Sci. 2021, 8, 2100798. [Google Scholar] [CrossRef]
  51. Forero Ramirez, L.M.; Gobin, E.; Aid-Launais, R.; Journe, C.; Moraes, F.C.; Picton, L.; Le Cerf, D.; Letourneur, D.; Chauvierre, C.; Chaubet, F. Gd(DOTA)-grafted submicronic polysaccharide-based particles functionalized with fucoidan as potential MR contrast agent able to target human activated platelets. Carbohydr. Polym. 2020, 245, 116457. [Google Scholar] [CrossRef] [PubMed]
  52. Li, X.; Bauer, W.; Israel, I.; Kreissl, M.C.; Weirather, J.; Richter, D.; Bauer, E.; Herold, V.; Jakob, P.; Buck, A.; et al. Targeting P-selectin by gallium-68-labeled fucoidan positron emission tomography for noninvasive characterization of vulnerable plaques: Correlation with in vivo 17.6T MRI. Arterioscler. Thromb. Vasc. Biol. 2014, 34, 1661–1667. [Google Scholar] [CrossRef] [PubMed] [Green Version]
  53. Abdollah, M.R.A.; Carter, T.J.; Jones, C.; Kalber, T.L.; Rajkumar, V.; Tolner, B.; Gruettner, C.; Zaw-Thin, M.; Torres, J.B.; Ellis, M.; et al. Fucoidan prolongs the circulation time of dextran-coated iron oxide nanoparticles. ACS Nano 2018, 12, 1156. [Google Scholar] [CrossRef] [PubMed] [Green Version]
  54. Chauvierre, C.; Aid-Launais, R.; Aerts, J.; Chaubet, F.; Maire, M.; Chollet, L.; Rolland, L.; Bonafé, R.; Rossi, S.; Bussi, S.; et al. Pharmaceutical development and safety evaluation of a GMP-grade fucoidan for molecular diagnosis of cardiovascular diseases. Mar. Drugs 2019, 17, 699. [Google Scholar] [CrossRef] [PubMed] [Green Version]
  55. Patankar, M.S.; Oehninger, S.; Barnett, T.; Williams, R.L.; Clark, G.F. A revised structure for fucoidan may explain some of its biological activities. J. Biol. Chem. 1993, 268, 21770–21776. [Google Scholar] [CrossRef]
  56. Usov, A.I.; Smirnova, G.P.; Bilan, M.I.; Shashkov, A.S. Polysaccharides of algae. 53. Brown alga Laminaria saccharina (L.) Lam. As a source of fucoidan. Russ. J. Bioorg. Chem. 1998, 24, 382–389. [Google Scholar]
  57. Chizhov, A.O.; Dell, A.; Morris, H.R.; Haslam, S.M.; McDowell, R.A.; Shashkov, A.S.; Nifant’ev, N.E.; Khatuntseva, E.A.; Usov, A.I. A study of fucoidan from the brown seaweed Chorda filum. Carbohydr. Res. 1999, 320, 108–119. [Google Scholar] [CrossRef]
  58. Chevolot, L.; Mulloy, B.; Ratiscol, J.; Foucault, A.; Colliec-Jouault, S. A disaccharide repeat unit is the major structure in fucoidans from two species of brown algae. Carbohydr. Res. 2001, 330, 529–535. [Google Scholar] [CrossRef]
  59. Chevolot, L.; Foucault, A.; Chaubet, F.; Kervarec, N.; Sinquin, C.; Fischer, A.-M.; Boisson-Vidal, C. Further data on the structure of brown seaweed fucans: Relationships with anticoagulant activity. Carbohydr. Res. 1999, 319, 154–165. [Google Scholar] [CrossRef]
  60. Bilan, M.I.; Grachev, A.A.; Ustuzhanina, N.E.; Shashkov, A.S.; Nifantiev, N.E.; Usov, A.I. Structure of a fucoidan from the brown seaweed Fucus evanescens C.Ag. Carbohydr. Res. 2002, 337, 719–730. [Google Scholar] [CrossRef]
  61. Bilan, M.I.; Grachev, A.A.; Ustuzhanina, N.E.; Shashkov, A.S.; Nifantiev, N.E.; Usov, A.I. A highly regular fraction of a fucoidan from the brown seaweed Fucus distichus L. Carbohydr. Res. 2004, 339, 511–517. [Google Scholar] [CrossRef] [PubMed]
  62. Descamps, V.; Colin, S.; Lahaye, M.; Jam, M.; Richard, C.; Potin, P.; Barbeyron, T.; Yvin, J.-C.; Kloareg, B. Isolation and culture of a marine bacterium degrading the sulfated fucans from marine brown algae. Mar. Biotechnol. 2006, 8, 27–39. [Google Scholar] [CrossRef] [PubMed] [Green Version]
  63. Nishino, T.; Nishioka, C.; Ura, H.; Nagumo, T. Isolation and partial characterization of a novel amino sugar-containing fucan sulfate from commercial Fucus vesiculosus fucoidan. Carbohydr. Res. 1994, 255, 213–224. [Google Scholar] [CrossRef]
  64. Mabeau, S.; Kloareg, B.; Joseleau, J.-P. Fractionation and analysis of fucans from brown algae. Phytochem. 1990, 29, 2441–2445. [Google Scholar] [CrossRef]
  65. Mabeau, S.; Kloareg, B. Isolation and analysis of the cell walls of brown algae: Fucus spiralis, F. ceranoides, F. vesiculosus, F. serratus, Bifurcaria bifurcata and Laminaria digitata. J. Exp. Bot. 1987, 38, 1573–1580. [Google Scholar] [CrossRef]
  66. Bourne, E.J.; Brush, P.; Percival, E. The active carbohydrate metabolites of the brown seaweed, Fucus vesiculosus. Carbohydr. Res. 1969, 9, 415–422. [Google Scholar] [CrossRef]
  67. Ruperez, P.; Ahrazem, O.; Leal, J.A. Potential antioxidant capacity of sulfated polysaccharides from the edible marine brown seaweed Fucus vesiculosus. J. Agric. Food Chem. 2002, 50, 840–845. [Google Scholar] [CrossRef]
  68. Rodríguez-Jasso, R.M.; Mussatto, S.I.; Pastrana, L.; Aguilar, C.N.; Teixeira, J.A. Extraction of sulfated polysaccharides by autohydrolysis of brown seaweed Fucus vesiculosus. J. Appl. Phycol. 2013, 25, 31–39. [Google Scholar] [CrossRef] [Green Version]
  69. Rodríguez-Jasso, R.M.; Mussatto, S.I.; Pastrana, L.; Aguilar, C.N.; Teixeira, J.A. Microwave-assisted extraction of sulfated polysaccharides (fucoidan) from brown seaweed. Carbohydr. Polym. 2011, 86, 1137–1144. [Google Scholar] [CrossRef] [Green Version]
  70. Obluchinskaya, E.D.; Makarova, M.N.; Pozharitskaya, O.N.; Shikov, A.N. Effect of ultrasound treatment on the chemical composition and anticoagulant properties of dry Fucus extract. Pharm. Chem. J. 2015, 49, 183–186. [Google Scholar] [CrossRef]
  71. Hahn, T.; Lang, S.; Ulber, R.; Muffler, K. Novel procedures for the extraction of fucoidan from brown algae. Process Biochem. 2012, 47, 1691–1698. [Google Scholar] [CrossRef]
  72. Flórez-Fernández, N.; Torres, M.D.; Gonsález-Muñoz, M.J.; Domínguez, H. Potential of intensification for the extraction and depolymerization of fucoidan. Algal Res. 2018, 30, 128–148. [Google Scholar] [CrossRef]
  73. Larsen, B.; Haug, A.; Painter, T.J. Sulphated polysaccharides in brown algae. I. Isolation and preliminary characterisation of three sulphated polysaccharides from Ascophyllum nodosum. Acta Chem. Scand. 1966, 20, 219–230. [Google Scholar] [CrossRef] [Green Version]
  74. Larsen, B. Sulphated polysaccharides in brown algae. II. Isolation of 3-O-β-D-xylopyranosyl-L-fucose from ascophyllan. Acta Chem. Scand. 1967, 21, 1395–1396. [Google Scholar] [CrossRef] [Green Version]
  75. Larsen, B.; Haug, A.; Painter, T.J. Sulphated polysaccharides in brown algae. III. The native state of fucoidan in Ascophyllum nodosum and Fucus vesiculosus. Acta Chem. Scand. 1970, 24, 3339–3352. [Google Scholar] [CrossRef] [Green Version]
  76. Percival, E. Glucuronoxylofucan, a cell wall polysaccharide of the Phaeophyceae. Chem. Ind. 1967, 511. [Google Scholar]
  77. Percival, E. Glucuronoxylofucan, a cell wall component of Ascophyllum nodosum. Part I. Carbohydr. Res. 1968, 7, 272–283. [Google Scholar] [CrossRef]
  78. Percival, E. Glucuronoxylofucan, a cell wall component of Ascophyllum nodosum. Part II. Methylation. Carbohydr. Res. 1971, 17, 121–126. [Google Scholar] [CrossRef]
  79. Medcalf, D.G.; Larsen, B. Fucose-containing polysaccharides in the brown algae Ascophyllum nodosum and Fucus vesiculosus. Carbohydr. Res. 1977, 59, 531–537. [Google Scholar] [CrossRef]
  80. Medcalf, D.G.; Larsen, B. Structural studies on ascophyllan and the fucose-containing complexes from the brown alga Ascophyllum nodosum. Carbohydr. Res. 1977, 59, 539–546. [Google Scholar] [CrossRef]
  81. Medcalf, D.G.; Schneider, T.L.; Barnett, R.W. Structural features of a novel glucuronogalactofucan from Ascophyllum nodosum. Carbohydr. Res. 1978, 66, 167–171. [Google Scholar] [CrossRef]
  82. Marais, M.-F.; Joseleau, J.-P. A fucoidan fraction from Ascophyllum nodosum. Carbohydr. Res. 2001, 336, 155–159. [Google Scholar] [CrossRef]
  83. Daniel, R.; Chevolot, L.; Carrascal, M.; Tissot, B.; Mourão, P.A.S.; Abian, J. Electrospray ionization mass spectrometry of oligosaccharides derived from fucoidan of Ascophyllum nodosum. Carbohydr. Res. 2007, 342, 826–834. [Google Scholar] [CrossRef]
  84. Nakayasu, S.; Soegima, R.; Yamaguchi, K.; Oda, T. Biological activities of fucose-containing polysaccharide ascophyllan isolated from the brown alga Ascophyllum nodosum. Biosci. Biotech. Biochem. 2009, 73, 961–964. [Google Scholar] [CrossRef] [Green Version]
  85. Jiang, Z.; Okimura, T.; Yokose, T.; Yamasaki, Y.; Yamaguchi, K.; Oda, T. Effects of sulfated fucan, ascophyllan, from the brown alga Ascophyllum nodosum on various cell lines: A comparative study on ascophyllan and fucoidan. J. Biosci. Bioeng. 2010, 110, 113–117. [Google Scholar] [CrossRef] [PubMed] [Green Version]
  86. Yuan, Y.; Macquarrie, D. Microwave assisted extraction of sulfated polysaccharides (fucoidan) from Ascophyllum nodosum and its antioxidant activity. Carbohydr. Polym. 2015, 129, 101–107. [Google Scholar] [CrossRef] [PubMed]
  87. Okolie, C.L.; Mason, B.; Mohan, A.; Pitts, N.; Udenigwe, C.C. The comparative influence of novel extraction technologies on in vitro prebiotic-inducing chemical properties of fucoidan extracts from Ascophyllum nodosum. Food Hydrocolloids 2019, 90, 462–471. [Google Scholar] [CrossRef]
  88. Wang, L.; Wang, L.; Yan, C.; Ai, C.; Wen, C.; Guo, X.; Song, S. Two Ascophyllum nodosum fucoidans with different molecular weights inhibit inflammation via blocking of TLR/NF-κB signaling pathway discriminately. Foods 2022, 11, 2381. [Google Scholar] [CrossRef]
  89. Liang, Y.; Zha, S.; Tentaku, M.; Okimura, T.; Jiang, Z.; Ueno, M.; Hirasaka, K.; Yamaguchi, K.; Oda, T. Supressive effect of sulfated polysaccharide ascophyllan isolated from Ascophyllum nodosum on the production of NO and ROS in LPS-stimulated RAW264.7 cells. Biosci. Biotech. Biochem. 2021, 85, 882–889. [Google Scholar] [CrossRef]
  90. Jin, W.; Lu, C.; Zhu, Y.; Zhao, J.; Zhang, W.; Wang, L.; Linchardt, R.J.; Wang, C.; Zhang, F. Fucoidans inhibited tau interaction and cellular uptake. Carbohydr. Polym. 2022, 299, 120176. [Google Scholar] [CrossRef]
  91. Sakai, T.; Kimura, H.; Kojima, K.; Shimanaka, K.; Irai, K.; Kato, I. Marine bacterial sulfated fucoglucuronomannan (SFGM) lyase digests brown algal SFGM into trisaccharides. Mar. Biotechnol. 2003, 5, 70–78. [Google Scholar] [CrossRef] [PubMed]
  92. Sanjeewa, K.K.A.; Herath, K.H.I.N.M.; Yang, H.-W.; Choi, C.S.; Jeon, Y.-J. Anti-inflammatory mechanisms of fucoidans to treat inflammatory diseases: A review. Mar. Drugs 2021, 19, 678. [Google Scholar] [CrossRef] [PubMed]
  93. Ho, C.-H.; Chen, M.-L.; Huang, H.-L.; Lai, C.-J.; Liu, C.-H.; Chuu, C.-P.; Lin, Y.-H. Active targeting of P-selectin by fucoidan modulates the molecular profiling of metastasis in docetaxel-resistant prostate cancer. Mar. Drugs 2022, 20, 542. [Google Scholar] [CrossRef] [PubMed]
  94. Harenberg, J.; Walenga, J.; Torri, G.; Dahl, O.E.; Drouet, L.; Fareed, J. Update of the recommendations on biosimilar low-molecular-weight heparins from the Scientific Subcommittee on Control of Anticoagulation of the International Society on Thrombosis and Hemostasis. J. Thromb. Haemost. 2013, 11, 1421–1425. [Google Scholar] [CrossRef]
  95. Restaino, O.F.; Schiraldi, C. Chondroitin sulfate: Are the purity and the structural features well assessed? A review on the analytical challenges. Carbohydr. Polym. 2022, 292, 119690. [Google Scholar] [CrossRef]
  96. Ustuzhanina, N.E.; Krylov, V.B.; Grachev, A.A.; Gerbst, A.G.; Nifantiev, N.E. Synthesis, NMR and conformational studies of fucoidan fragments. 8. Convergent block-wise synthesis of long chain linear and 2,3-branched oligosaccharides. Synthesis 2006, 23, 4017–4031. [Google Scholar] [CrossRef]
  97. Krylov, V.B.; Kaskova, Z.M.; Vinnitskiy, D.Z.; Ustyuzhanina, N.E.; Grachev, A.A.; Chizhov, A.O.; Nifantiev, N.E. Acid-promoted synthesis of per-O-sulfated fucooligosaccharides related to fucoidan fragments. Carbohydr. Res. 2011, 346, 540–550. [Google Scholar] [CrossRef]
  98. Vinnitskiy, D.Z.; Krylov, V.B.; Ustyuzhanina, N.E.; Dmitrenok, A.S.; Nifantiev, N.E. The synthesis of heterosaccharides related to the fucoidan from Chordaria flagelliformis bearing α-L-fucofuranosyl unit. Org. Biomol. Chem. 2016, 14, 598–611. [Google Scholar] [CrossRef]
  99. Silchenko, A.S.; Ustyuzhanina, N.E.; Kusaykin, M.I.; Krylov, V.B.; Shashkov, A.S.; Dmitrenok, A.S.; Usoltseva (Menshova), R.V.; Zueva, A.O.; Nifantiev, N.E.; Zvyagintseva, T.N. Expression and biochemical characterization and substrate specificity of the fucoidanase from Formosa algae. Glycobiology 2017, 27, 254–263. [Google Scholar] [CrossRef] [Green Version]
  100. Shvetsova, S.V.; Shabalin, K.A.; Bobrov, K.S.; Ivanen, D.R.; Ustyuzhanina, N.E.; Krylov, V.B.; Nifantiev, N.E.; Naryzhny, S.N.; Zgoda, V.G.; Eneyskaya, E.V.; et al. Characterization of a new α-L-fucosidase isolated from Fusarium proliferatum LE1 that is regioselective to α-(1/4)-L-fucosidic linkage in the hydrolysis of α-L-fucobiosides. Biochimie 2017, 132, 54–65. [Google Scholar] [CrossRef]
  101. Silchenko, A.S.; Rubtsov, N.K.; Zueva, A.O.; Kusaykin, M.I.; Rasin, A.B.; Ermakova, S.P. Fucoidan-active α-L-fucosidases of the GH29 and GH95 families from a fucoidan degrading cluster of the marine bacterium Wenyingzhuangia fucanilytica. Arch. Biochem. Biophys. 2022, 728, 109373. [Google Scholar] [CrossRef] [PubMed]
Marinedrugs 20 00638 g001 550
Figure 1. The current idealized formula of brown algal fucan sulfate (structural elements, which are possibly important for biological activity, are indicated).
Figure 1. The current idealized formula of brown algal fucan sulfate (structural elements, which are possibly important for biological activity, are indicated).
Marinedrugs 20 00638 g001
Table
Table 1. Yields and composition (in %) of several polysaccharide preparations isolated from A. nodosum and F. vesiculosus *.
Table 1. Yields and composition (in %) of several polysaccharide preparations isolated from A. nodosum and F. vesiculosus *.
PreparationYieldFucXylGlcManGalUASO3Na
Ascophyllan [71]1.915.5 (1.00)13.4 (0.95)0.3 (0.02)3.4 (0.2)0.6 (0.04)21.4 (1.17)9.6 (1.06)
Fucan sulfate from A. nodosum [71]1.2528.4 (1.00)4.3 (0.16)2.0 (0.06)0.8 (0.03)5.3 (0.17)5.8 (0.17)19.4 (1.17)
Fucan sulfate from A. nodosum [69] (1.00)(0.05)----(0.47)
Fucan sulfate from F. vesiculosus [5] (1.00)tr.--tr.-(0.47)
Commercial fucoidan from F. vesiculosus [71] 24.8 (1.00)1.9 (0.09)0.8 (0.03)1.0 (0.04)3.1 (0.11)9.6 (0.33)22.6 (1.56)
* Molar proportions relative to fucose content (Fuc = 1.00) are given in brackets.
Publisher’s Note: MDPI stays neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Share and Cite

MDPI and ACS Style

Usov, A.I.; Bilan, M.I.; Ustyuzhanina, N.E.; Nifantiev, N.E. Fucoidans of Brown Algae: Comparison of Sulfated Polysaccharides from Fucus vesiculosus and Ascophyllum nodosum. Mar. Drugs 2022, 20, 638. https://doi.org/10.3390/md20100638

AMA Style

Usov AI, Bilan MI, Ustyuzhanina NE, Nifantiev NE. Fucoidans of Brown Algae: Comparison of Sulfated Polysaccharides from Fucus vesiculosus and Ascophyllum nodosum. Marine Drugs. 2022; 20(10):638. https://doi.org/10.3390/md20100638

Chicago/Turabian Style

Usov, Anatolii I., Maria I. Bilan, Nadezhda E. Ustyuzhanina, and Nikolay E. Nifantiev. 2022. "Fucoidans of Brown Algae: Comparison of Sulfated Polysaccharides from Fucus vesiculosus and Ascophyllum nodosum" Marine Drugs 20, no. 10: 638. https://doi.org/10.3390/md20100638

APA Style

Usov, A. I., Bilan, M. I., Ustyuzhanina, N. E., & Nifantiev, N. E. (2022). Fucoidans of Brown Algae: Comparison of Sulfated Polysaccharides from Fucus vesiculosus and Ascophyllum nodosum. Marine Drugs, 20(10), 638. https://doi.org/10.3390/md20100638

Note that from the first issue of 2016, this journal uses article numbers instead of page numbers. See further details here.

Article Metrics

Back to TopTop