Seaweed Polysaccharides: Structure and Applications

Navarro, Diego A.; Ponce, Nora M.A.; Stortz, Carlos A.

doi:10.1007/978-3-319-61288-1_3

Cited by 25 publications

(17 citation statements)

References 224 publications

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“…Because of the presence of an aldehyde hydrate moiety associated to free AnGal, such a strategy could be conducted through reductive amination reactions. Even though reductive amination has been widely used in organic synthesis, its applicability remains challenging when dealing with carbohydrates [18–20]. Rearrangements, enolization and dimerization are among the drawbacks that can be encountered during the transformation of mono- or oligosaccharides directly into glycamines.…”

Section: Resultsmentioning

confidence: 99%

“…When using ammonium chloride and ammonium sulfate (Table 1, entries 5 and 6) a distinct product was detected in the reaction medium by mass spectroscopy (see Supporting Information File 1), which probably corresponded to a 1-amino-1-deoxyketose (compound 5 ). This is known as an Amadori product [18] obtained from the characteristic rearrangement of the 1-deoxy-2-hydroxyimine intermediate. Yet, the secondary amine bis -disaccharide 6 was frequently found as byproduct in the present work.…”

Section: Resultsmentioning

confidence: 99%

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Aqueous semisynthesis of C-glycoside glycamines from agarose

Dallagnol¹,

Orsato²,

Ducatti³

et al. 2017

Beilstein J. Org. Chem.

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Agarose was herein employed as starting material to produce primary, secondary and tertiary C-glycoside glycamines, including mono- and disaccharide structures. The semisynthetic approach utilized was generally based on polysaccharide-controlled hydrolysis followed by reductive amination. All reactions were conducted in aqueous media and without the need of hydroxyl group protection. We were able to identify optimal conditions for the reductive amination of agar hydrolysis products and to overcome the major difficulties related to this kind of reaction, also extending it to reducing anhydrosugars. The excess of ammonium acetate, methyl- or dimethylamine, and the use of a diluted basic (pH 11) reaction media were identified as important aspects to achieve improved yields, as well as to decrease the amount of byproducts commonly related to reductive amination of carbohydrates. This strategy allowed the transposition of the 3,6-anhydro-α-L-galactopyranose unit (naturally present in the agarose structure) to all glycamines synthesized, constituting an amino-substituted C-threofuranoside moiety, which is closely related to (+)-muscarine.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Aqueous semisynthesis of C-glycoside glycamines from agarose

Dallagnol¹,

Orsato²,

Ducatti³

et al. 2017

Beilstein J. Org. Chem.

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“…After filtration to eliminate insoluble residue, CaCl2 solution (5%-15% (w/v)) is added to the filtrate to precipitate alginate in calcium salt. Then, calcium alginate could be bleached using aqueous oxygen peroxide or sodium hypochlorite (1%-10% (v/v)) treatment followed by mixing with HCl solution (1%-5% (v/v)) to obtain alginic acid which is purify by repeated water washing to completely remove calcium salt [48,49,51,52]. Finally, the highly purified alginic acid form is usually: (i) converted to sodium alginate using carbonate or NaOH solution treatment, (ii) precipitated using alcohol (ethanol, isopropanol…), (iii) dried and (iv) ground in fine powder.…”

Section: Polyglucuronic Acid From Bacteria Fungi and Green Algaementioning

confidence: 99%

“…Commercial alginates are produced mainly from Macrocystis pyrifera, Ascophyllum nodosum, Laminaria species, Eclonia maxima, Lessonia nigrescens, Durvillea Antarctica and Sargassum species [50]. Many processes are used to extract alginate [51][52][53][54]. In a general way, algae powder was first demineralized using acid solution such as HCl (0.1%-0.5%) and secondly treated with alkaline solution using NaHCO 3 or NaOH (0.5 to 2%; pH 10-11) at 60-70 • C which easily allows the release of alginates in sodium salt form [51,53].…”

Section: Polyglucuronic Acid From Bacteria Fungi and Green Algaementioning

confidence: 99%

Use of Anionic Polysaccharides in the Development of 3D Bioprinting Technology

et al. 2019

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Three-dimensional (3D) bioprinting technology is now one of the best ways to generate new biomaterial for potential biomedical applications. Significant progress in this field since two decades ago has pointed the way toward use of natural biopolymers such as polysaccharides. Generally, these biopolymers such as alginate possess specific reactive groups such as carboxylate able to be chemically or enzymatically functionalized to generate very interesting hydrogel structures with biomedical applications in cell generation. This present review gives an overview of the main natural anionic polysaccharides and focuses on the description of the 3D bioprinting concept with the recent development of bioprinting processes using alginate as polysaccharide.

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“…They may also be involved in cell interaction and adhesion, and form a protective barrier against pathogens ( Vavilala and D´Souza, 2015 ; Udayan et al, 2017 ). Seaweeds, including red (Rhodophyta), green (Chlorophyta), and brown (Phaeophyceae) marine macroalgae, biosynthesize sulfated polysaccharides as a key component of their cell walls ( Cosenza et al, 2017 ). The amounts and structure of these cell wall components vary greatly.…”

Section: Introductionmentioning

confidence: 99%

Diversity of Sulfated Polysaccharides From Cell Walls of Coenocytic Green Algae and Their Structural Relationships in View of Green Algal Evolution

2020

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Seaweeds biosynthesize sulfated polysaccharides as key components of their cell walls. These polysaccharides are potentially interesting as biologically active compounds. Green macroalgae of the class Ulvophyceae comprise sulfated polysaccharides with great structural differences regarding the monosaccharide constituents, linearity of their backbones, and presence of other acidic substituents in their structure, including uronic acid residues and pyruvic acid. These structures have been thoroughly studied in the Ulvales and Ulotrichales, but only more recently have they been investigated with some detail in ulvophytes with giant multinucleate (coenocytic) cells, including the siphonous Bryopsidales and Dasycladales, and the siphonocladous Cladophorales. An early classification of these structurally heterogeneous polysaccharides was based on the presence of uronic acid residues in these molecules. In agreement with this classification based on chemical structures, sulfated polysaccharides of the orders Bryopsidales and Cladophorales fall in the same group, in which this acidic component is absent, or only present in very low quantities. The cell walls of Dasycladales have been less studied, and it remains unclear if they comprise sulfated polysaccharides of both types. Although in the Bryopsidales and Cladophorales the most important sulfated polysaccharides are arabinans and galactans (or arabinogalactans), their major structures are very different. The Bryopsidales produce sulfated pyruvylated 3-linked β- d -galactans, in most cases, with ramifications on C6. For some species, linear sulfated pyranosic β- l -arabinans have been described. In the Cladophorales, also sulfated pyranosic β- l -arabinans have been found, but 4-linked and highly substituted with side chains. These differences are consistent with recent molecular phylogenetic analyses, which indicate that the Bryopsidales and Cladophorales are distantly related. In addition, some of the Bryopsidales also biosynthesize other sulfated polysaccharides, i.e., sulfated mannans and sulfated rhamnans. The presence of sulfate groups as a distinctive characteristic of these biopolymers has been related to their adaptation to the marine environment. However, it has been shown that some freshwater algae from the Cladophorales also produce sulfated polysaccharides. In this review, structures of sulfated polysaccharides from bryopsidalean, dasycladalean, and cladophoralean green algae studied until now are described and analyzed based on current phylogenetic understanding, with the aim of unveiling the important knowledge gaps that still exist.

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Seaweed Polysaccharides: Structure and Applications

Cited by 25 publications

References 224 publications

Aqueous semisynthesis of C-glycoside glycamines from agarose

Aqueous semisynthesis of C-glycoside glycamines from agarose

Use of Anionic Polysaccharides in the Development of 3D Bioprinting Technology

Diversity of Sulfated Polysaccharides From Cell Walls of Coenocytic Green Algae and Their Structural Relationships in View of Green Algal Evolution

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