NMR structural determination of unique invertebrate glycosaminoglycans endowed with medical properties

Pomin, Vitor H.

doi:10.1016/j.carres.2015.05.004

Cited by 47 publications

(18 citation statements)

References 75 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Fucosylated chondroitin sulfates (FucCS) are specific components of the holothurian body walls. Structural analysis of FucCS is mainly based on the data of NMR spectroscopy [ 23 , 41 , 42 ]. Fine structures of FucCS depend on the sea cucumber species [ 7 , 8 ].…”

Section: Discussionmentioning

confidence: 99%

Structure and Anti-Inflammatory Activity of a New Unusual Fucosylated Chondroitin Sulfate from Cucumaria djakonovi

et al. 2018

View full text Add to dashboard Cite

Fucosylated chondroitin sulfate CD was isolated from the sea cucumber Cucumaria djakonovi collected from the Avachinsky Gulf of the eastern coast of Kamchatka. Structural characterization of CD was performed using a series of non-destructive NMR spectroscopic procedures. The polysaccharide was shown to contain a chondroitin core [→3)-β-d-GalNAc-(1→4)-β-d-GlcA-(1→]n where about 60% of GlcA residues were 3-O-fucosylated, while another part of GlcA units did not contain any substituents. The presence of unsubstituted both at O-2 and O-3 glucuronic acid residues in a structure of holothurian chondroitin sulfate is unusual and has not been reported previously. Three different fucosyl branches Fucp2S4S, Fucp3S4S and Fucp4S were found in the ratio of 2:1:1. The GalNAc units were mono- or disulfated at positions 4 and 6. Anti-inflammatory activity of CD was assessed on a model of acute peritoneal inflammation in rats. About 45% inhibition was found for CD, while a structurally related linear chondroitin sulfate SS from cartilage of the fish Salmo salar demonstrated only 31% inhibition, indicating that the presence of sulfated fucosyl branches is essential for anti-inflammatory effect of chondroitin sulfates of marine origin.

show abstract

Section: Discussionmentioning

confidence: 99%

Structure and Anti-Inflammatory Activity of a New Unusual Fucosylated Chondroitin Sulfate from Cucumaria djakonovi

et al. 2018

View full text Add to dashboard Cite

show abstract

“…13,14 In this sense, the modification of chitosan with sulfate groups provides new and attractive physicochemical properties compared to the starting chitosan, as well as interesting pharmacological properties and biological activities, such as immunomodulation, antioxidant, antiviral, anti-radiation, antiinflammatory, neuroprotective, anti-proliferative and anticoagulant effects. [15][16][17][18] This review aims to address the so-called heparanized chitosans, a very interesting family of polysaccharides that have demonstrated the ability to mimic heparan sulfates and heparin as ligands of different proteins and, therefore, exerting their biological activity mimicking the function of these glycosaminoglycans (Fig. 2).…”

Section: Reviewmentioning

confidence: 99%

Heparanized chitosans: towards the third generation of chitinous biomaterials

et al. 2021

View full text Add to dashboard Cite

show abstract

“…Recently, a method based on ESI-MS analysis of peracetylated oligomeric portions, as derived from polysaccharides by Smith degradation or by enzyme hydrolysis followed by acetylation, has been described as an expedient tool for providing critical structural information on a spectrum of oligosaccharides [37,[128][129][130][131]. Moreover, nuclear magnetic resonance (NMR) spectroscopy is an effective, non-invasive method in general studies on biopolymers, and NMR is a particularly valuable technique in the determination of molecular structures of polysaccharides [132][133][134][135][136][137][138][139][140]. This spectroscopic technique provides information not only on the saccharide composition, glycosidic linkage patterns and sugar sequences, but also on its molecular mass.…”

Section: Techniques For Structural Characterization Of Polysaccharidesmentioning

confidence: 99%

“…The position of sulfate groups can be determined conventionally by comparison of methylation analysis results obtained for the polysaccharide sulfates with those for its desulfated derivatives [7,8,121,123,124,130]. Infrared spectroscopy (IR) spectroscopy, 1 H and 13 C nuclear magnetic resonance (NMR) spectroscopy may provide additional information on the position of sulfate groups [8,121,123,[137][138][139][140].…”

Section: Techniques For Structural Characterization Of Polysaccharidesmentioning

confidence: 99%

Exploiting the Amazing Diversity of Natural Source-Derived Polysaccharides: Modern Procedures of Isolation, Engineering, and Optimization of Antiviral Activities

et al. 2020

View full text Add to dashboard Cite

Naturally occurring polysaccharide sulfates are highly diverse, owning variations in the backbone structure, linkage pattern and stereochemistry, branching diversity, sulfate content and positions of sulfate group(s). These structural characteristics bring about diverse sulfated polymers with dissimilar negative charge densities and structure–activity relationships. Herein, we start with a short discussion of techniques needed for extraction, purification, chemical sulfation, and structural characterization of polysaccharides. Processes of isolation and sulfation of plant-derived polysaccharides are challenging and usually involve two steps. In this context, we describe an integrated extraction-sulfation procedure that produces polysaccharide sulfates from natural products in one step, thereby generating additional pharmacological activities. Finally, we provide examples of the spectrum of natural source-derived polysaccharides possessing specific features of bioactivity, in particular focusing on current aspects of antiviral drug development and drug–target interaction. Thus, the review presents a detailed view on chemically engineered polysaccharides, especially sulfated derivatives, and underlines their promising biomedical perspectives.

show abstract

NMR structural determination of unique invertebrate glycosaminoglycans endowed with medical properties

Cited by 47 publications

References 75 publications

Structure and Anti-Inflammatory Activity of a New Unusual Fucosylated Chondroitin Sulfate from Cucumaria djakonovi

Structure and Anti-Inflammatory Activity of a New Unusual Fucosylated Chondroitin Sulfate from Cucumaria djakonovi

Heparanized chitosans: towards the third generation of chitinous biomaterials

Exploiting the Amazing Diversity of Natural Source-Derived Polysaccharides: Modern Procedures of Isolation, Engineering, and Optimization of Antiviral Activities

Contact Info

Product

Resources

About