Separation and quantification of neoagaro- and agaro-oligosaccharide products generated from agarose digestion by β-agarase and HCl in liquid chromatography systems

Kazłowski, Bartosz; Pan, Chorng Liang; Ko, Yuan Tih

doi:10.1016/j.carres.2008.06.019

Cited by 55 publications

(34 citation statements)

References 24 publications

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“…15) Similar results, including the formation of even-numbered oligosaccharides from red algal galactans, have been reported by several other researchers. 16,17) On the other hand, Yu 18) and Yang et al 19) reported recently the formation of odd-numbered oligosaccharides by mild acid hydrolysis of -carrageenan and both -carrageenan and agarose, respectively.…”

Section: Resultssupporting

confidence: 85%

Selective Hydrolysis of the 3,6-Anhydrogalacotosidic Linkage in Red Algal Galactan: A Combination of Reductive Acid Hydrolysis and Anhydrous Mercaptolysis

Hama

Tsuneoka

Morita

et al. 2010

Bioscience, Biotechnology, and Biochemistry

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Here we report a simple method for the structural analysis of red algal galactan containing 3,6-anhydrogalactose. Structural heterogeneity in the galactan was demonstrated by this method. For selective hydrolysis of 3,6-anhydrogalactosidic linkages in the galactan, conditions for reductive mild acid hydrolysis were examined by characterizing the resulting oligosaccharide alditols by anhydrous mercaptolysis. Residues other than alditols at the reducing ends, including labile 3,6-anhydrogalactose, were liberated quantitatively as diethyl dithioacetal derivatives, whereas alditols at the reducing ends were not derivatized and were liberated as alditols intact. The liberated sugars were then separated and measured quantitatively by gas-liquid chromatography. Heating of agarose in reductive hydrolysis with 0.3 M trifluoroacetic acid in the presence of an acid-stable reducing agent, 4-methyl morpholine borane, at 80 C for 90 min and for 90 C for 45 min was found to be optimum for the selective hydrolysis of 3,6-anhydrogalactosidic bonds, without detectable cleavage of other glycosidic bonds.Key words: 3,6-anhydrogalactose; algal galactan; heterogeneity; mercaptolysis; reductive hydrolysis Various biological activities have been found in marine algal polysaccharides.1-3) However, since algal polysaccharides in nature are generally heterogeneous in size and composition, the structure-activity relationships of these saccharides are not fully established yet.Red algal galactans such as agar, carrageenans, and porphyran contain 3,6-anhydrogalactose (AG) as a major component monosaccharide. 4) Since AG is easily destroyed by harsh acidic conditions such as acid hydrolysis and methanolysis, which are generally used in compositional and structural analysis of polysaccharides, the details of the structure of these algal galactans remain to be elucidated. Stevenson and Furneaux5) reported a double-hydrolysis procedure in which mild acid hydrolysis was employed to cleave only 3,6-anhydrogalactosidic linkages, followed by reduction with sodium borohydride. The resulting oligosaccharide alditols with 3,6-anhydrogalactitol at the reducing ends were fully hydrolyzed for compositional analysis by gas-liquid chromatography (GLC). They also developed a reductive hydrolysis procedure in which mild acid hydrolysis is carried out in the presence of an acid-stable reducing agent, 4-methyl morpholine borane (MMB), to obtain oligosaccharide alditols with 3,6-anhydrogalactitol at the reducing ends.5) Since then, these methods have been modified by several other groups.6-8) However, the degree of hydrolysis of the 3,6-anhydrogalactosidic bonds in the galactans was evaluated by determining the resulting AG-ol, because AG, unlike AG-ol, cannot be measured directly by these methods. Therefore, the behavior of the remaining AG residues during the reaction period remains substantially unknown.We have reported a method for the determination of component monosaccharides of red algal galactans by which all the component sugars including AG were libera...

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Section: Resultssupporting

confidence: 85%

Selective Hydrolysis of the 3,6-Anhydrogalacotosidic Linkage in Red Algal Galactan: A Combination of Reductive Acid Hydrolysis and Anhydrous Mercaptolysis

Hama

Tsuneoka

Morita

et al. 2010

Bioscience, Biotechnology, and Biochemistry

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“…In addition, chromatographic methods are utilized to control the hydrolysis process (Chen et al, 2004;Kazlowski et al, 2008), being useful for monitoring bioactive oligosaccharide production. In this paper we describe the production and characterization of agaro-and carra-oligosaccharides via the partial acid hydrolysis of commercial agarose and kappa-carrageenan.…”

Section: Introductionmentioning

confidence: 99%

Production of agaro- and carra-oligosaccharides by partial acid hydrolysis of galactans

Ducatti¹,

Colodi²,

Gonçalves³

et al. 2011

Rev. bras. farmacogn.

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Agaro-and carra-oligosaccharides were produced by partial acid hydrolysis of commercial agarose and kappa-carrageenan. Di-and tetrasaccharides were purified by gel filtration chromatography and characterized by NMR (1D and 2D) spectroscopy and ESIMS. The following oligosaccharides were obtained: agarobiose, agarotetraose, kappa-carrabiose and kappa-carratetraose. Agarobiose and agarotetraose were used as standards to develop a high performance size exclusion chromatography (HPSEC) method which was utilized to study the hydrolysis rate of agarose and oligosaccharide production. Six hours of hydrolysis (0.1 M TFA, 65 o C) produced mainly di-and tetrasaccharides. The methodology for oligosaccharide production and evaluation developed in the present work shows good potential for the production of bioactive oligosaccharides. Keywords:agaro-oligosaccharides carra-oligosaccharides partial acid hydrolysis 3,6-anhydro-galactose agarose kappa-carrageenan

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“…Agarose, the main component of polysaccharides in agar, is hydrolyzed easily in acetic conditions to yield water soluble oligosaccharides (10). The resultant oligosaccharides, which are agaro-oligosaccharides (AGOs; Agaphytose TM ), have been investigated widely in terms of their structure and bioactivity (11)(12)(13)(14). A recent report has described AGOs as preventing gut dysbiosis in mice without influence in the obese phenotype and serum metabolic parameters in abnormal high-fat dietfed conditions (15).…”

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confidence: 99%

Agaro-Oligosaccharides Regulate Gut Microbiota and Adipose Tissue Accumulation in Mice

Higashimura

Baba

Inoüe

et al. 2017

Journal of Nutritional Science and Vitaminology, J Nutr Sci Vit

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Summary Gut microbiota are deeply associated with the prevalence of obesity. Agarose is hydrolyzed easily to yield oligosaccharides, designated as agaro-oligosaccharides (AGO). This study evaluated the effects of AGO on obese phenotype and gut microbial composition in mice. Mice were administered AGO in drinking water (AGO-receiving mice). 16S rRNA gene sequencing analyses revealed their fecal microbiota profiles. Serum bile acids were ascertained using a LC-MS/MS system. Compared to the control group, AGO administration significantly reduced epididymal adipose tissue weights and serum non-esterified fatty acid concentrations, but the cecal content weights were increased. Data from the serum bile acid profile show that concentrations of primary bile acids (cholic acid and chenodeoxycholic acid), but not those of secondary bile acids (deoxycholic acid, lithocholic acid, and ursodeoxycholic acid), tended to increase in AGO-receiving mice. 16S rRNA gene sequencing analyses showed that the relative abundances of 15 taxa differed significantly in AGO-receiving mice. Of these, the relative abundances of Rikenellaceae and Lachnospiraceae were found to be positively correlated with epididymal adipose tissue weight. The relative abundances of Bacteroides and Ruminococcus were correlated negatively with epididymal adipose tissue weight. Although the definitive role of gut microbes of AGO-received mice is still unknown, our data demonstrate the possibility that AGO administration affects the gut microbial composition and inhibits obesity in mice.

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Separation and quantification of neoagaro- and agaro-oligosaccharide products generated from agarose digestion by β-agarase and HCl in liquid chromatography systems

Cited by 55 publications

References 24 publications

Selective Hydrolysis of the 3,6-Anhydrogalacotosidic Linkage in Red Algal Galactan: A Combination of Reductive Acid Hydrolysis and Anhydrous Mercaptolysis

Selective Hydrolysis of the 3,6-Anhydrogalacotosidic Linkage in Red Algal Galactan: A Combination of Reductive Acid Hydrolysis and Anhydrous Mercaptolysis

Production of agaro- and carra-oligosaccharides by partial acid hydrolysis of galactans

Agaro-Oligosaccharides Regulate Gut Microbiota and Adipose Tissue Accumulation in Mice

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