Autohydrolysis of a partially cyclized m/u-carrageenan and structural elucidation of the oligosaccharides by chemical analysis, NMR spectroscopy and UV-MALDI mass spectrometry

Ciancia, Marina; Sato, Yasuto; Nonami, Hiroshi; Cerezo, Alberto S.; Erra‐Balsells, Rosa; Matulewicz, Marı́a C.

doi:10.3998/ark.5550190.0006.c25

Cited by 7 publications

(4 citation statements)

References 19 publications

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“…The mild acidic conditions generated in the media during the hydrothermal process could lead to the fragmentation of glycosidic linkages. A similar trend was reported for the autohydrolysis of a partially cyclized mu/nu-carrageenan from S. skottsbergii caused after 11 h at 60 °C, from the initial 198 kDa carrageenan to fractions lower than 1.9 kDa [ 28 ].…”

Section: Resultssupporting

confidence: 81%

Microwave-Assisted Extraction of Carrageenan from Sarcopeltis skottsbergii

et al. 2023

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The development of greener processes for the sustainable utilization of raw materials is increasingly demanded for environmental and economic reasons. A rapid and chemical-free technique was proposed for the extraction of hybrid kappa/iota (6/4) carrageenan from Sarcopeltis (ex Gigartina) skottsbergii. After separation, carrageenans were analyzed by Fourier transform infrared attenuated total reflectance, high-performance size-exclusion chromatography, and rheology. Maximum carrageenan extraction yields up to 63–64% were obtained operating at 110 or at 160 °C, for 5–7 min considering the sum of the heating and cooling periods, but the extraction of the phenolic fraction was favored at 220 °C. The recovered carrageenan showed apparent viscous values around 103 mPa at the lowest tested shear rates (0.1 1/s) and could be suitable to formulate films. Furthermore, those carrageenans obtained under 140 °C showed gel characteristics without previous separation from the liquid extract, avoiding ethanolic precipitation and energy consumption. The antiradical properties correlated with the phenolic content in the liquid phase, but no influence of temperature on the reducing properties was observed. The microwave-assisted hydrothermal treatment could be an efficient tool without needing chemicals for the extraction of carrageenans, which showed adequate rheological properties for commercial uses.

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Section: Resultssupporting

confidence: 81%

Microwave-Assisted Extraction of Carrageenan from Sarcopeltis skottsbergii

et al. 2023

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“…The H-type fractions, obtained by autohydrolysis, display similar inhibitory activities as the corresponding unfractionated material ( Figure 4A ). C2-selective desulfation of fucopyranose (Fuc) and degradation happen during the process of autohydrolysis ( Ciancia et al, 2005 ; Pomin et al, 2005 ; Anastyuk et al, 2012 ; Rodriguez-Jasso et al, 2013 ; Menshova et al, 2015 ; Shevchenko et al, 2015 ; Wu et al, 2015 ). This suggests that sulfation at the C2 of Fuc residues is not crucial for AT-binding.…”

Section: Resultsmentioning

confidence: 99%

“…Marine algae oligosaccharides, polysaccharides and their derivatives together with several animal-originated polysaccharides were prepared based on the previous studies ( Ciancia et al, 2005 ; Wang et al, 2010 ; Anastyuk et al, 2012 ; Jin et al, 2012 , Jin et al, 2013 , Jin et al, 2017 , Jin et al, 2018a , Jin et al, 2018b , Jin et al, 2019 , Jin et al, 2020a , Jin et al, 2020b , Jin et al, 2020c , Jin et al, 2020d ; Rodriguez-Jasso et al, 2013 ; Menshova et al, 2015 ; Shevchenko et al, 2015 ; Wu et al, 2015 ). They were summarized in Scheme 1 , Table 1 with proposed structures in Figure 1 and more details can be found in Supplementary Table S1 ( Supplementary data 1 ).…”

Section: Methodsmentioning

confidence: 99%

Interactions of marine sulfated glycans with antithrombin and platelet factor 4

Zhang

Jin²,

Pomin³

et al. 2022

Front. Mol. Biosci.

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The molecular interactions of sulfated glycans, such as heparin, with antithrombin (AT) and platelet factor 4 (PF4) are essential for certain biological events such as anticoagulation and heparin induced thrombocytopenia (HIT). In this study, a library including 84 sulfated glycans (polymers and oligomers) extracted from marine algae along with several animal-originated polysaccharides were subjected to a structure-activity relationship (SAR) study regarding their specific molecular interactions with AT and PF4 using surface plasmon resonance. In this SAR study, multiple characteristics were considered including different algal species, different methods of extraction, molecular weight, monosaccharide composition, sulfate content and pattern and branching vs. linear chains. These factors were found to influence the binding affinity of the studied glycans with AT. Many polysaccharides showed stronger binding than the low molecular weight heparin (e.g., enoxaparin). Fourteen polysaccharides with strong AT-binding affinities were selected to further investigate their binding affinity with PF4. Eleven of these polysaccharides showed strong binding to PF4. It was observed that the types of monosaccharides, molecular weight and branching are not very essential particularly when these polysaccharides are oversulfated. The sulfation levels and sulfation patterns are, on the other hand, the primary contribution to strong AT and PF4 interaction.

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“…SJ and SJ-D were separated by anion-exchange chromatography on a DEAE-Bio Gel agarose FF (6 cm × 40 cm) eluted with water (5 L), 0.5 M NaCl (5 L) (Fraction W: SJ-W and SJ-D-W), 1 M NaCl (5 L) (Fraction I: SJ-I and SJ-D-I) and 2 M NaCl (5 L) (Fraction S: SJ-S and SJ-D-S) [ 14 ]. Autohydrolysis was carried out by methods described in previous studies [ [18] , [19] , [20] , [21] , [22] , [23] , [24] ]. Two types of autohydrolyzed polysaccharides, including higher molecular weight, H-type fractions (SJ-D-W-H, SJ-D-I-H and SJ-D-S-H) and lower molecular weight, L-type fractions (SJ-D-W-L, SJ-D-I-L and SJ-D-S-L) were obtained [ 14 ].…”

Section: Methodsmentioning

confidence: 99%

The structure-activity relationship of the interactions of SARS-CoV-2 spike glycoproteins with glucuronomannan and sulfated galactofucan from Saccharina japonica

Jin

Zhang

Mitra

et al. 2020

International Journal of Biological Macromolecules

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The SARS-CoV-2 spike glycoproteins (SGPs) and human angiotensin converting enzyme 2 (ACE2) are the two key targets for the prevention and treatment of COVID-19. Host cell surface heparan sulfate (HS) is believed to interact with SARS-CoV-2 SGPs to facilitate host cell entry. In the current study, a series of polysaccharides from Saccharina japonica were prepared to investigate the structure-activity relationship on the binding abilities of polysaccharides (oligosaccharides) to pseudotype particles, including SARS-CoV-2 SGPs, and ACE2 using surface plasmon resonance. Sulfated galactofucan (SJ-D-S-H) and glucuronomannan (Gn) displayed strongly inhibited interaction between SARS-CoV-2 SGPs and heparin while showing negligible inhibition of the interaction between SARS-CoV-2 SGPs and ACE2. The IC 50 values of SJ-D-S-H and Gn in blocking heparin SGP binding were 27 and 231 nM, respectively. NMR analysis showed that the structure of SJ-D-S-H featured with a backbone of 1, 3-linked α-L-Fuc p residues sulfated at C4 and C2/C4 and 1, 3-linked α-L-Fuc p residues sulfated at C4 and branched with 1, 6-linked β-D-galacto-biose; Gn had a backbone of alternating 1, 4-linked β-D-GlcA p residues and 1, 2-linked α-D-Man p residues. The sulfated galactofucan and glucuronomannan showed strong binding ability to SARS-CoV-2 SGPs, suggesting that these polysaccharides might be good candidates for preventing and/or treating SARS-CoV-2.

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Autohydrolysis of a partially cyclized m/u-carrageenan and structural elucidation of the oligosaccharides by chemical analysis, NMR spectroscopy and UV-MALDI mass spectrometry

Cited by 7 publications

References 19 publications

Microwave-Assisted Extraction of Carrageenan from Sarcopeltis skottsbergii

Microwave-Assisted Extraction of Carrageenan from Sarcopeltis skottsbergii

Interactions of marine sulfated glycans with antithrombin and platelet factor 4

The structure-activity relationship of the interactions of SARS-CoV-2 spike glycoproteins with glucuronomannan and sulfated galactofucan from Saccharina japonica

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