Preparative separation of oligosaccharides from K-carrageenan, sodium hyaluronate, and dextran by SuperdexTM 30 prep. grade

Caram-Lelham, Ninus; Sundelöf, Lars‐Olof; Andersson, Torvald

doi:10.1016/0008-6215(95)00119-e

Cited by 24 publications

(13 citation statements)

References 15 publications

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“…In the mass spectrum of the slowest‐eluting fraction K1, the doubly charged ion at m / z 322.1 identified a trisaccharide with a molecular mass of 646.2 Da, indicating a composition of two G4S units and one A unit (Table 1), with a likely sequence of G4S‐A‐G4S. It was surprising initially that the shortest fragment identified was a trisaccharide, and not the expected disaccharide as reported previously [15–17,20]. The molecular mass of the adjacent fraction K2 was 386 Da higher than that of K1, suggesting a pentasaccharide with an additional A‐G4S biose unit (Table 1).…”

Section: Resultssupporting

confidence: 61%

Mechanism of mild acid hydrolysis of galactan polysaccharides with highly ordered disaccharide repeats leading to a complete series of exclusively odd‐numbered oligosaccharides

et al. 2009

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The diverse oligosaccharide sequences present in poly-saccharides, glycoproteins, glycolipids and proteogly-cans serve multiple functions. Acidic polysaccharide glycosaminoglycans (GAGs) are ubiquitous in vertebrate tissues, and have important biological functions through binding to various proteins. Marine-derived polysaccharides are often of an anionic nature, and these GAG-like molecules have been exploited for their antiviral, antioxidant, anticoagulant and other signal-ing activities [1-4]. Recent studies have shown that marine polysaccharide carrageenans can inhibit the attachment of several pathogenic viruses, e.g. herpes simplex virus [5], dengus virus [6], and human papillo-mavirus [7,8], and hence they have become of considerable biomedical interest, owing to their antiviral activities and therapeutic potential. Carrageenans are highly sulfated galactans isolated from marine red algae, with linear repeating sequences Sulfated galactan j-carrageenan is a linear polysaccharide with a repeating disaccharide sequence of alternating 4-sulfated 3-linked galactose and 4-linked 3,6-anhydrogalactose units. In contrast to many examples of chemical hydrolysis of polysaccharides, mild acid treatment of j-carra-geenan resulted in facile and highly specific cleavage. In this article, we report the identification, by various MS and chromatographic techniques, of an unexpected series of exclusively odd-numbered oligosaccharide fragments from its hydrolytic products. Detailed sequence analysis of the products indicated that all the oligosaccharide fragments have the 4-sulfated 3-linked galactose residues at both the reducing and the nonreducing ends. Further detailed investigation and analysis suggested that these odd-numbered oligosaccharides were derived from two-step cleavages of the glycosidic bonds on either sides of the 3,6-anhydrogalactose residues. Neutral galactan agarose also contains 3,6-anhydrogalactose and has a similar backbone sequence, and exhibited similar results upon mild acid hydrolysis. It is highly unusual to obtain exclusively odd-numbered oligo-saccharides from polysaccharides composed of ordered disaccharide repeats. Abbreviations A, 4-linked a-3,6-anhydrogalactose; A2S, 4-linked 2-O-sulfated-aD -3,6

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Section: Resultssupporting

confidence: 61%

Mechanism of mild acid hydrolysis of galactan polysaccharides with highly ordered disaccharide repeats leading to a complete series of exclusively odd‐numbered oligosaccharides

et al. 2009

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“…After inactivation of the enzymes by heating at 100°C for 5 min and centrifugation at 10,000g for 5 min, the supernatants were transferred to new tubes and kept at Ϫ20°C until use. The reaction products of each sample were analyzed on a gel permeation chromatography column built up of 2 coupled Superdex™ 30 preparative grade columns (XK/26, Pharmacia; 1,000 ϫ 26 ID) 32 equilibrated and eluted with 0.1 M NaCl. Fractions of 7 ml were collected at a flow rate of 0.6 ml/min and the radioactivity in each fraction was measured in a beta-counter.…”

Section: Characterization Of the Hyaluronan-degrading Pattern Of Testmentioning

confidence: 99%

Testicular hyaluronidase induces tubular structures of endothelial cells grown in three‐dimensional colagen gel through a CD44‐mediated mechanism

Rahmanian

Heldin

2001

Intl Journal of Cancer

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Cultured brain capillary endothelial cells grown in a 3-dimensional collagen gel can form tubular structures after stimulation by angiogenic factors. We found that treatment of such cultures with testicular hyaluronidase led to formation of tubular structures and cell survival. Anion-exchange chromatography of the enzyme preparation on a MonoQ column revealed the presence of the angiogenic factor basic fibroblast growth factor (bFGF) in the flow-through fraction, as determined by immunoblotting; part of the effect on endothelial cell morphogenesis could thus be ascribed to bFGF. However, adsorbed fractions eluted with increasing concentrations of NaCl, which exhibited hyaluronan-degrading activity at neutral pH, did not contain bFGF but were still able to induce tube-like structures of the endothelial cells. Streptomyces hyaluronidase failed to evoke the same effect. Interestingly, blocking of hyaluronan binding to CD44 receptors by the monoclonal antibody KM114 inhibited the effect of hyaluronidase, but not of bFGF, on endothelial cell tube formation. Our data suggest a CD44-mediated specific role for certain populations of testicular hyaluronidase in the induction of angiogenesis.

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“…Oligosaccharides have recently drawn a considerable interest due to medical effects and indications of their very specific interaction in certain carbohydrate systems with larger molecules of similar structure (Caram-Lelham & Sundelöf, 1995). More recently, sulfated oligosaccharides head groups of glycoproteins and glycolipids have been recognized as playing a significant role in many important biological processes, including fertilization, immune defense, parasitic infection, cell growth, cell-cell adhesion and inflammation (Xia et al, 2000).…”

Section: Introductionmentioning

confidence: 99%

Preparation, structural characterization and in vitro antitumor activity of kappa-carrageenan oligosaccharide fraction from Kappaphycus striatum

Yuan

Song

2005

J Appl Phycol

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Oligosaccharides were prepared through mild hydrochloric acid hydrolysis of kappa-carrageenan from Kappaphycus striatum to compare the antitumor activity with carrageenan polysaccharides. Oligosaccharide fractions were isolated by gel permeation chromatography and the structure of fraction 1 (F1) was studied by using negative-ion electrospray ionization-mass spectrometry (ESI-MS), and 1 H and 13 C-NMR spectrometry. The in vitro antitumor effects in three human neoplastic cell lines (KB, BGC, and Hela) of polysaccharides and F1 were investigated. The bioassay results showed that F1 exhibited relatively higher antitumor activity against the three cancer cells than polysaccharides.

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Preparative separation of oligosaccharides from K-carrageenan, sodium hyaluronate, and dextran by SuperdexTM 30 prep. grade

Cited by 24 publications

References 15 publications

Mechanism of mild acid hydrolysis of galactan polysaccharides with highly ordered disaccharide repeats leading to a complete series of exclusively odd‐numbered oligosaccharides

Mechanism of mild acid hydrolysis of galactan polysaccharides with highly ordered disaccharide repeats leading to a complete series of exclusively odd‐numbered oligosaccharides

Testicular hyaluronidase induces tubular structures of endothelial cells grown in three‐dimensional colagen gel through a CD44‐mediated mechanism

Preparation, structural characterization and in vitro antitumor activity of kappa-carrageenan oligosaccharide fraction from Kappaphycus striatum

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