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1.
Int J Biol Macromol ; 190: 739-753, 2021 Nov 01.
Article in English | MEDLINE | ID: mdl-34509519

ABSTRACT

Naturally occurring polysaccharide-structured nanoparticles have developed as promising materials for treatment of bone health disorders. Silver nanoparticle (ST-AgNP) structured from sulfated polygalacto-fucopyranose comprising of recurring structural entities of 2-SO3-α-(1 â†’ 3)-fucopyranose and 6-O-acetyl-ß-(1 â†’ 4)-galactopyranose isolated from marine macroalga Sargassum tenerrimum demonstrated potential activities associated with osteogenesis. Subsequent treatment with ST-AgNP, activity of alkaline phosphatase (63 mU/mg) was raised in osteoblast stem cells (human mesenchymal, hMSC) than that in control (30 mU/mg). Intense growth of mineralized nodule on the surface of hMSC was apparent following treatment with ST-AgNP. Increased population of bone morphogenic protein-2 (23%) and osteocalcin+ cells (50%) on M2 macrophages were apparent following treatment with ST-AgNP (0.25 mg/mL). Glucocorticoid-induced in vivo animal model studies of ST-AgNP exhibited significant recovery of serum biochemical parameters along with serum estradiol and parathyroid hormone compared to disease control. Disease-induced groups treated with ST-AgNP showed the disappearance of osteoporotic cavities in the trabecular bone. Following treatment with ST-AgNP, serum calcium and phosphorus contents were significantly recovered.


Subject(s)
Fucose/therapeutic use , Galactans/therapeutic use , Glucocorticoids/adverse effects , Nanoparticles/chemistry , Osteoporosis/chemically induced , Osteoporosis/drug therapy , Alkaline Phosphatase/metabolism , Animals , Antioxidants/pharmacology , Body Weight/drug effects , Bone Morphogenetic Protein 2/metabolism , Calcification, Physiologic/drug effects , Carbon-13 Magnetic Resonance Spectroscopy , Cell Line , Cell Survival/drug effects , Digestion/drug effects , Feeding Behavior/drug effects , Female , Femur/drug effects , Femur/pathology , Fucose/isolation & purification , Fucose/pharmacology , Galactans/isolation & purification , Galactans/pharmacology , Humans , Mesenchymal Stem Cells/drug effects , Osteoblasts/drug effects , Osteocalcin/metabolism , Proton Magnetic Resonance Spectroscopy , Rats, Wistar , Spectrometry, X-Ray Emission , Spectrophotometry, Ultraviolet
2.
Int J Biol Macromol ; 183: 589-599, 2021 Jul 31.
Article in English | MEDLINE | ID: mdl-33933545

ABSTRACT

Consumption of marine alga-based polysaccharides as additional functional foods can endow with health benefits by diminishing the risk of chronic diseases. A polygalacto-fucopyranose characterized as [→1)-2, 4-SO3-α-Fucp-(3 → 1)-{2-SO3-α-Fucp-(3→}] with [(4 → 1)-6-OAc-ß-Galp-(4→] side chain isolated from marine alga Sargassum wightii exhibited potential antihypertensive activity. Upon treatment with studied polygalactofucan (50 mg/kg BW), serum hypertension biomarkers troponin-T (1.3 pg/mL), troponin-I (1.2 µg/dL) and angiotensin-II converting enzyme (0.18 pg/mL) were significantly recovered in hypertensive rats compared to disease control. Serum cardiovascular risk indices of diseased rats were significantly decreased (< 10%, p < 0.05) after administration of the studied galactofucan (50 mg/kg BW) related to hypertension group (> 17%), and were comparable with standard antihypertensive agent telmisartan (8.3-10.2% at 2 mg/kg BW). The studied compound was safe for consumption as obvious from the high LD50 value (>5 g/kg), and could be developed as a prospective functional food ingredient attenuating the pathophysiological attributes causing hypertension-related conditions.


Subject(s)
Antihypertensive Agents/pharmacology , Blood Pressure/drug effects , Fucose/pharmacology , Hypertension/drug therapy , Sargassum , Animals , Antihypertensive Agents/isolation & purification , Antihypertensive Agents/toxicity , Cadmium Chloride , Disease Models, Animal , Drug Discovery , Fucose/analogs & derivatives , Fucose/isolation & purification , Fucose/toxicity , Hypertension/chemically induced , Hypertension/physiopathology , Lethal Dose 50 , Male , Rats, Wistar , Sargassum/chemistry , Telmisartan/pharmacology
3.
Mar Drugs ; 19(3)2021 Mar 18.
Article in English | MEDLINE | ID: mdl-33803892

ABSTRACT

Unique fucosylated glycosaminoglycans (FG) have attracted increasing attention for various bioactivities. However, the precise structures of FGs usually vary in a species-specific manner. In this study, HfFG was isolated from Holothuria floridana and purified by anion exchange chromatography with the yield of ~0.9%. HfFG was composed of GlcA, GalNAc and Fuc, its molecular weight was 47.3 kDa, and the -OSO3-/-COO- molar ratio was 3.756. HfFG was depolymerized by a partial deacetylation-deaminative cleavage method to obtain the low-molecular-weight HfFG (dHfFG). Three oligosaccharide fragments (Fr-1, Fr-2, Fr-3) with different molecular weights were isolated from the dHfFG, and their structures were revealed by 1D and 2D NMR spectroscopy. HfFG should be composed of repeating trisaccharide units -{(L-FucS-α1,3-)d-GlcA-ß1,3-d-GalNAc4S6S-ß1,4-}-, in which sulfated fucose (FucS) includes Fuc2S4S, Fuc3S4S and Fuc4S residues linked to O-3 of GlcA in a ratio of 45:35:20. Furthermore, the heparanase inhibitory activities of native HfFG and oligosaccharide fragments (Fr-1, Fr-2, Fr-3) were evaluated. The native HfFG and its oligosaccharides exhibited heparanase inhibitory activities, and the activities increased with the increase of molecular weight. Additionally, structural characteristics such as sulfation patterns, the terminal structure of oligosaccharides and the presence of fucosyl branches may be important factors affecting heparanase inhibiting activity.


Subject(s)
Enzyme Inhibitors/pharmacology , Fucose/pharmacology , Glucuronidase/antagonists & inhibitors , Glycosaminoglycans/pharmacology , Holothuria/metabolism , Animals , Enzyme Inhibitors/isolation & purification , Fucose/isolation & purification , Glucuronidase/metabolism , Glycosaminoglycans/isolation & purification , Humans , Molecular Structure , Molecular Weight , Structure-Activity Relationship
4.
J Chromatogr A ; 1632: 461610, 2020 Nov 22.
Article in English | MEDLINE | ID: mdl-33080533

ABSTRACT

Due to the heterogeneous and isomeric nature of glycans, the development of an advanced separation of distinct glycan isomers is essential for glycan research and application. In this study, we utilized porous graphite carbon (PGC) chromatography for the separation of isomeric oligosaccharides without reduction or chemical derivatization at 190 °C in a custom-built heating oven. Furthermore, the fine structures of glycan isomers could be identified by using ultrahigh temperature PGC liquid chromatography mass spectrometry (UHT-PGC-LCMS). A nonreduced hydrolyzed dextran was applied to verify the performance of UHT-PGC. When the temperature of the PGC column was increased from 25 to 190 °C, the liquid chromatography separation power of the nonreduced dextran ladder significantly increased. The advantage of the UHT-PGC column was its high peak capacity with gradient elution in 10 min at 190 °C, 6700 psi, and a 250 µL/min flow rate for native glycan analysis. Four synthetic Lewis antigen isomers were used to elucidate the separation effectiveness in UHT-PGC. Moreover, mass spectrometry-based sequencing to generate specific diagnostic ions from the four synthetic Lewis antigens was used to predict isomeric glycans based on the relative intensity ratio (RIR) of diagnostic ions. The intensities of the diagnostic ions of synthetic isomers were used to identify each isomer of the fucosylated glycan. The results clearly showed that terminal Lewis A and X residues were in the 3- and 6-arms of N-glycan, respectively.


Subject(s)
Chromatography, Liquid/methods , Fucose/chemistry , Fucose/isolation & purification , Graphite/chemistry , Tandem Mass Spectrometry/methods , Temperature , Dextrans/chemistry , Glycosylation , Hydrolysis , Ions , Isomerism , Polysaccharides/chemistry , Polysaccharides/isolation & purification , Porosity , Time Factors
5.
Glycoconj J ; 37(5): 553-563, 2020 10.
Article in English | MEDLINE | ID: mdl-32617856

ABSTRACT

Three polysaccharides (SH-1, SH-2 and SH-3) were purified from a brown macroalgea, Sargassum hemiphyllum. The autohydrolysis products from each polysaccharide were separated to three fractions (S fractions as oligomers, L fractions as low molecular weight polysaccharides and H fractions as high molecular weight polysaccharides). Mass spectroscopy of S fractions (SH-1-S, SH-2-S and SH-3-S) showed that these three polymers all contained short stretches of sulfated fucose. The structures of L fractions (SH-1-L, SH-2-L and SH-3-L) were determined by nuclear magnetic resonance (NMR). SH-1-L was composed of two units, unit A (sulfated galactofucan) and unit B (sulfated xylo-glucuronomannan). Unit A contained a backbone of (1, 6-linked ß-D-Gal) n1, (1, 3-linked 4-sulfated α-L-Fuc) n2, (1, 3-linked 2, 4-di-sulfated α-L-Fuc) n3, (1, 4-linked α-L-Fuc) n4 and (1, 3-linked ß-D-Gal) n5, accompanied by some branches, such as sulfated fuco-oligomers, sulfated galacto-oligomers or sulfated galacto-fuco-oligomers. And unit B consisted of alternating 1, 4-linked ß-D-glucuronic acid (GlcA) and 1, 2-linked α-D-mannose (Man) with the Man residues randomly sulfated at C6 or branched with xylose (Xyl) at C3. Both SH-2-L and SH-3-L were composed of unit A and their difference was attributed to the ratio of n1: n2: n3: n4: n5. Based on monosaccharide analysis, we hypothesize that both SH-1-H and SH-2-H contained unit A and unit B while SH-3-H had a structure similar to SH-3-L. An assessment of anti-complement activities showed that the sulfated galactofucan had higher activities than sulfated galacto-fuco-xylo-glucuronomannan. These results suggest that the sulfated galactofucans might be a good candidate for anti-complement drugs.


Subject(s)
Fucose/chemistry , Galactose/chemistry , Glucuronic Acid/chemistry , Polysaccharides/chemistry , Sargassum/chemistry , Fucose/isolation & purification , Galactose/isolation & purification , Hydrolysis , Magnetic Resonance Spectroscopy , Mass Spectrometry , Polysaccharides/isolation & purification , Polysaccharides/ultrastructure
6.
Carbohydr Res ; 478: 18-24, 2019 May 15.
Article in English | MEDLINE | ID: mdl-31048118

ABSTRACT

The brown seaweed Scytosiphon lomentaria produces moderate amounts of fucoidans. By cetrimide fractionation, typical heavily sulfated galactofucans are obtained, with no major signs of chemical heterogeneity, together with fractions with higher proportions of xylose, mannose and uronic acids. Anyway, fucose is the most important monosaccharide in most of the subfractions of the subsequent extracts. The fucan moieties appear to be mostly as 3-linked α-l-fucopyranosyl units, with several patterns of sulfate and branching. Galactose is mostly 6-linked, whereas mannose appears to be 2-linked, and xylose appears mostly as terminal stubs. Small amounts of 2-O-acetylated fucose units appear. A high and selective antiviral activity against HSV-1 and HSV-2 was determined for the galactofucan fractions whereas the uronofucoidans were inactive.


Subject(s)
Antiviral Agents/pharmacology , Fucose/pharmacology , Galactose/pharmacology , Herpesvirus 1, Human/drug effects , Herpesvirus 2, Human/drug effects , Polysaccharides/pharmacology , Antiviral Agents/chemistry , Antiviral Agents/isolation & purification , Carbohydrate Conformation , Fucose/chemistry , Fucose/isolation & purification , Galactose/chemistry , Galactose/isolation & purification , Microbial Sensitivity Tests , Phaeophyceae/chemistry , Polysaccharides/chemistry , Polysaccharides/isolation & purification
7.
J Chromatogr A ; 1579: 49-59, 2018 Dec 07.
Article in English | MEDLINE | ID: mdl-30389210

ABSTRACT

If a multi-component monosugar mixture including fucose was used as the substrates for the Klebsiella oxytoca fermentation, it could offer the following two benefits simultaneously; (i) the removal of all monosugars other than fucose, and (ii) the acquisition of 2,3-butanediol (BD). To utilize such two benefits in favor of the economical efficiency of the fucose production process, it is essential to accomplish a high-purity separation between fucose and BD on the basis of a highly-economical mode. To address this issue, we aimed to develop a simulated moving bed (SMB) process for continuous-mode separation of fucose and BD with high purities. It was first found that an Amberchrom-CG71C resin could become a suitable adsorbent for the separation of interest. The intrinsic parameters of fucose and BD on such proven adsorbent were determined, and then applied to the optimal design of the fucose-BD separation SMB. The capability of the designed SMB in ensuring high purities and high yields was experimentally verified. Finally, we devised two potential strategies to make a further improvement in product concentrations and/or desorbent usage while keeping the purities and yields of fucose and BD almost unchanged. The first strategy was based on partial extract-collection and partial extract-discard, which was found to result in 33% higher BD product concentration. The second strategy was based on partial extract-collection, partial extract-recycle, and partial desorbent-port closing, which could lead to 25% lower desorbent usage, 33% higher BD product concentration, and 7% higher fucose product concentration.


Subject(s)
Butylene Glycols/isolation & purification , Chemistry Techniques, Analytical/methods , Fucose/isolation & purification , Adsorption , Chemistry Techniques, Analytical/instrumentation , Fermentation , Klebsiella oxytoca/metabolism
8.
J Chromatogr A ; 1575: 113-121, 2018 Nov 09.
Article in English | MEDLINE | ID: mdl-30287060

ABSTRACT

The effectiveness of a simulated moving bed (SMB) technology in the continuous separation of fucose from a multi-component monosugar mixture, which stemmed from defatted microalgae, has recently been identified. To guarantee high economical efficiency of such fucose-production method, the comprehensive optimization of the relevant fucose-separation SMB process needs to be accomplished such that its production rate (Prate) and/or productivity (Prod) can be maximized while meeting the requirements on fucose product concentration (Cprod,F) and pressure drop (ΔPSMB). To resolve this issue, the SMB optimization program based on standing-wave-design method and genetic algorithm was prepared and then applied to the fucose-separation SMB optimization. It was found that the Prate, under a given particle size, could reach its maximum when the column length was selected to create a balance between the effects of the two limiting factors related to Cprod,F and ΔPSMB. It was also found that the Prate was governed by fucose yield, if the SMB would be in need of a relatively high Cprod,F; otherwise, the Prate was governed by feed flow rate. If the particle size of the SMB adsorbent was fixed at one of the commercially available ones, the SMB conditions leading to the highest Prate and the highest Prod coincided with each other. By contrast, if the particle size was included as one of optimization variables, the Prate and Prod represented a trade-off relationship. Finally, it was confirmed from the simultaneous optimization for Prate and Prod that the increase of particle size improved Prate at the cost of Prod, thereby causing the maximum Prod to be always attained at a smaller particle size than the maximum Prate regardless of the target Cprod,F level.


Subject(s)
Algorithms , Chromatography , Fucose/isolation & purification , Industrial Microbiology/instrumentation , Industrial Microbiology/methods , Microalgae/chemistry , Adsorption , Electromagnetic Phenomena , Particle Size , Pressure
9.
Mar Drugs ; 16(8)2018 Jul 30.
Article in English | MEDLINE | ID: mdl-30061548

ABSTRACT

The objectives of this study were to employ response surface methodology (RSM) to investigate and optimize the effect of ultrasound-assisted extraction (UAE) variables, temperature, time and amplitude on the yields of polysaccharides (fucose and total glucans) and antioxidant activities (ferric reducing antioxidant power (FRAP) and 1,1-diphenyl-2-picryl-hydrazyl radical scavenging activity (DPPH)) from Laminariadigitata, and to explore the suitability of applying the optimum UAE conditions for L.digitata to other brown macroalgae (L.hyperborea and Ascophyllumnodosum). The RSM with three-factor, four-level Box-Behnken Design (BBD) was used to study and optimize the extraction variables. A second order polynomial model fitted well to the experimental data with R² values of 0.79, 0.66, 0.64, 0.73 for fucose, total glucans, FRAP and DPPH, respectively. The UAE parameters studied had a significant influence on the levels of fucose, FRAP and DPPH. The optimised UAE conditions (temperature = 76 °C, time = 10 min and amplitude = 100%) achieved yields of fucose (1060.7 ± 70.6 mg/100 g dried seaweed (ds)), total glucans (968.6 ± 13.3 mg/100 g ds), FRAP (8.7 ± 0.5 µM trolox/mg freeze-dried extract (fde)) and DPPH (11.0 ± 0.2%) in L.digitata. Polysaccharide rich extracts were also attained from L.hyperborea and A. nodosum with variable results when utilizing the optimum UAE conditions for L.digitata.


Subject(s)
Chemical Fractionation/methods , Free Radical Scavengers/pharmacology , Laminaria/chemistry , Seaweed/chemistry , Chemical Fractionation/instrumentation , Free Radical Scavengers/isolation & purification , Fucose/analysis , Fucose/isolation & purification , Fucose/pharmacology , Glucans/analysis , Glucans/isolation & purification , Glucans/pharmacology , Phenols/analysis , Phenols/isolation & purification , Phenols/pharmacology , Polysaccharides/analysis , Polysaccharides/isolation & purification , Polysaccharides/pharmacology , Ultrasonic Waves
10.
Molecules ; 23(8)2018 Jul 31.
Article in English | MEDLINE | ID: mdl-30065217

ABSTRACT

Polysaccharides from Ascophyllum nodosum (AnPS) were extracted and purified via an optimized protocol. The optimal extraction conditions were as follows: extraction time of 4.3 h, extraction temperature of 84 °C and ratio (v/w, mL/g) of extraction solvent (water) to raw material of 27. The resulting yield was 9.15 ± 0.23% of crude AnPS. Two fractions, named AnP1-1 and AnP2-1 with molecular weights of 165.92 KDa and 370.68 KDa, were separated from the crude AnPS by chromatography in DEAE Sepharose Fast Flow and Sephacryl S-300, respectively. AnP1-1 was composed of mannose, ribose, glucuronic acid, glucose and fucose, and AnP2-1 was composed of mannose, glucuronic acid, galactose and fucose. AnPS, AnP1-1 and AnP2-1 exhibited high scavenging activities against ABTS radical and superoxide radical, and showed protective effect on H2O2-induced oxidative injury in RAW264.7 cells. Furthermore, the immunostimulatory activities of AnP1-1 and AnP2-1 were evaluated by Caco-2 cells, the results showed both AnP1-1 and AnP2-1 could significantly promote the production of immune reactive molecules such as interleukin (IL)-8, IL-1ß, interferon (IFN)-γ, and tumor necrosis factor (TNF)-α. Therefore, the results suggest that AnPS and its two fractions may be explored as a potential functional food supplement.


Subject(s)
Adjuvants, Immunologic/isolation & purification , Antioxidants/isolation & purification , Ascophyllum/chemistry , Liquid-Liquid Extraction/methods , Polysaccharides/isolation & purification , Adjuvants, Immunologic/chemistry , Adjuvants, Immunologic/pharmacology , Animals , Antioxidants/chemistry , Antioxidants/pharmacology , Caco-2 Cells , Cell Survival/drug effects , Chromatography, DEAE-Cellulose , Fucose/chemistry , Fucose/isolation & purification , Galactose/chemistry , Galactose/isolation & purification , Glucuronic Acid/chemistry , Glucuronic Acid/isolation & purification , Humans , Hydrogen Peroxide/antagonists & inhibitors , Hydrogen Peroxide/pharmacology , Interferon-gamma/biosynthesis , Interferon-gamma/immunology , Interleukin-1beta/biosynthesis , Interleukin-1beta/immunology , Interleukin-8/biosynthesis , Interleukin-8/immunology , Mannose/chemistry , Mannose/isolation & purification , Mice , Polysaccharides/chemistry , Polysaccharides/pharmacology , RAW 264.7 Cells , Solvents/chemistry , Sulfates/chemistry , Tumor Necrosis Factor-alpha/biosynthesis , Tumor Necrosis Factor-alpha/immunology , Water/chemistry
11.
Int J Biol Macromol ; 118(Pt B): 2082-2091, 2018 Oct 15.
Article in English | MEDLINE | ID: mdl-30012482

ABSTRACT

Water-soluble polysaccharides were isolated from Azolla filiculoides to determine their chemical and structural characteristics as well as anticancer and immunostimulatory activities. Crude and fractions (F1 and F2) were mainly composed of neutral sugars (70.0-80.1%), proteins (2.1-14.2%) and uronic acids (1.2-10.8%). The polysaccharides were mostly formed of different levels of fucose (23.8-61.2%), galactose (28.5-38.7%), mannose (7.5-16.7%), xylose (13.3-13.6%), glucose (12.7-13.3%), arabinose (5.5-11.6%) and rhamnose (8.0-9.5%) units. The polysaccharide molecules contained one or more sub-fractions with average molecular weight ranging from 992 to 2162 × 103 g/mol. Crude and fractionated polysaccharides induced RAW264.7 macrophages to release pro-inflammatory mediators and cytokines including nitric oxide, IL-1ß, TNF-α, IL-6, IL-10 and IL-12 through NF-κB and MAPKs signaling pathways as confirmed by the presence of p-NK-κB, p-JNK, p-ERK and p-38 proteins in the cell cytoplasm. The most immunostimulating polysaccharide, F2, consisted of alternating →3)-Fuc-(1→ and →4)-Fuc-(1 → residues.


Subject(s)
Bryophyta/chemistry , Fresh Water , Fucose/isolation & purification , Galactose/isolation & purification , Immunologic Factors/chemistry , Immunologic Factors/isolation & purification , Animals , Antineoplastic Agents/pharmacology , Chemical Fractionation , Cytokines/genetics , Cytokines/metabolism , Fucose/chemistry , Galactose/chemistry , Glycosides/chemistry , HT29 Cells , HeLa Cells , Humans , Immunomodulation/drug effects , Macrophages/drug effects , Macrophages/metabolism , Mice , Polysaccharides/chemistry , Proton Magnetic Resonance Spectroscopy , RAW 264.7 Cells , RNA, Messenger/genetics , RNA, Messenger/metabolism
12.
J Proteome Res ; 16(11): 4237-4243, 2017 11 03.
Article in English | MEDLINE | ID: mdl-28953389

ABSTRACT

Here we report evidence that new aminoquinoline N-glycan fluorescent labels interfere with the release of core α(1-6) fucose from N-glycans by bovine kidney α-l-fucosidase (BKF). BKF is a commonly employed exoglycosidase for core α(1-6) fucose determination. Molecular simulations of the bound and unbound Fuc-α(1-6)-GlcNAc, where GlcNAc is situated at the reducing end for all N-glycans, suggest that the reduced BKF activity may be due to a nonoptimal fit of the highest populated conformers in the BKF active binding site at room temperature. Population analysis and free energy estimates suggest that an enhanced flexibility of the labeled sugar, which facilitates recognition and binding, can be achievable with extended reaction conditions. We provide these experimental conditions using a sequential exoglycosidase digestion array using high concentrations of BKF.


Subject(s)
Aminoquinolines/pharmacology , Fucose/isolation & purification , Polysaccharides/chemistry , alpha-L-Fucosidase/metabolism , Animals , Binding Sites , Cattle , Fluorescent Dyes , Polysaccharides/metabolism , Staining and Labeling
13.
Molecules ; 21(10)2016 Oct 09.
Article in English | MEDLINE | ID: mdl-27735839

ABSTRACT

The optimization extraction process, preliminary characterization and antioxidant activities of polysaccharides from Semen Juglandis (SJP) were studied in this paper. Based on the Box-Behnken experimental design and response surface methodology, the optimal extraction conditions for the SJP extraction were obtained as follows: temperature 88 °C, extraction time 125 min and ratio of liquid to solid 31 mL/g. Under these conditions, experimental extraction yield of SJP was (5.73 ± 0.014)% (n = 5), similar to the predicted value of 5.78%. Furtherly, the purified SJP obtained from SJP extract by DEAE-52 and Sephacryl S-100 chromatography was analyzed to be rhamnose, galacturonic acid, galactose, arabinose and fucose in the molar ratio of 1:6.34:1.38:3.21:1.56. And the weight-average molecular weight and radius of gyration of the purified SJP in 0.1 M NaCl were determined to be 2.76 × 104 g/mol and 122 nm by SEC-MALLS, respectively. More importantly, it exhibited appreciable antioxidant activities compared to the standard Vc, such as DPPH radical scavenging activity (IC50 0.21 mg/mL), strong reducing power, ABTS radical scavenging activity (IC50 0.29 mg/mL), and hydroxyl radical scavenging activity (IC50 0.38 mg/mL). These results indicate that SJP may be useful for developing functional health products or natural antioxidant.


Subject(s)
Antioxidants/chemistry , Free Radical Scavengers/chemistry , Juglans/chemistry , Polysaccharides/chemistry , Antioxidants/isolation & purification , Antioxidants/pharmacology , Arabinose/chemistry , Arabinose/isolation & purification , Free Radical Scavengers/isolation & purification , Free Radical Scavengers/pharmacology , Fucose/chemistry , Fucose/isolation & purification , Galactose/chemistry , Galactose/isolation & purification , Hexuronic Acids/chemistry , Hexuronic Acids/isolation & purification , Polysaccharides/isolation & purification , Polysaccharides/pharmacology , Rhamnose/chemistry , Rhamnose/isolation & purification
14.
Food Chem ; 209: 267-73, 2016 Oct 15.
Article in English | MEDLINE | ID: mdl-27173562

ABSTRACT

Fucoidan is a sulphated polysaccharide that consists mainly of fucose, normally found in brown seaweeds. In this study, fucoidan was extracted from Sargassum binderi (Fsar) from Malaysia and subsequently characterised. The chemical characteristics of Fsar were found to be different than those of commercial food grade fucoidan (Fysk) and those of previously studied fucoidans. NMR analysis proposed that the main structure of Fsar is →3)fuc-2-OSO3(-)(1→3)fuc(1→. The molecular weight (47.87kDa) and degree of sulphation (0.20) of Fsar were higher than those of Fysk, at 27.98kDa and 0.15, respectively. However, Fsar's polydispersity index (1.12) and fucose content (34.50%) were lower than those of Fysk, at 1.88 and 43.30%, respectively. Both Fsar and Fysk showed similar thermo-gravimetric properties with four mass losses, amorphous in nature and negative optical rotations. Results show that Fsar has fundamental characteristics of fucoidan with different structural conformation i.e. variation in glycosidic linkages and sulphate group orientation.


Subject(s)
Fucose/isolation & purification , Plant Extracts/chemistry , Polysaccharides/isolation & purification , Sargassum/chemistry , Seaweed/chemistry , Magnetic Resonance Spectroscopy , Malaysia , Molecular Weight , Sargassum/growth & development , Seaweed/growth & development
15.
Glycobiology ; 25(8): 881-7, 2015 Aug.
Article in English | MEDLINE | ID: mdl-25926563

ABSTRACT

The repeat unit of the K12 capsular polysaccharide isolated from the Acinetobacter baumannii global clone 1 clinical isolate, D36, was elucidated by means of chemical and spectroscopical methods. The structure was shown to contain N-acetyl-D-galactosamine (D-GalpNAc), N-acetyl-D-fucosamine and N-acetyl-L-fucosamine linked together in the main chain, with the novel sugar, 5,7-diacetamido-3,5,7,9-tetradeoxy-L-glycero-L-altro-non-2-ulosonic acid (5,7-di-N-acetylacinetaminic acid or Aci5Ac7Ac), attached to D-GalpNAc as a side branch. This matched the sugar composition of the K12 capsule and the genetic content of the KL12 capsule gene cluster reported previously. D-FucpNAc was predicted to be the substrate for the initiating transferase, ItrB3, with the Wzy polymerase making a α-D-FucpNAc-(1 → 3)-D-GalpNAc linkage between the repeat units. The three glycosyltransferases encoded by KL12 are all retaining glycosyltransferases and were predicted to form specific linkages between the sugars in the K12 repeat unit.


Subject(s)
Acinetobacter baumannii/chemistry , Bacterial Capsules/chemistry , Glycosyltransferases/chemistry , Acetylgalactosamine/chemistry , Acetylgalactosamine/isolation & purification , Acinetobacter baumannii/enzymology , Carbohydrate Sequence , Fucose/analogs & derivatives , Fucose/chemistry , Fucose/isolation & purification , Glycosyltransferases/metabolism , Molecular Sequence Data , Sialic Acids/chemistry , Sialic Acids/isolation & purification
16.
Ultrason Sonochem ; 23: 308-16, 2015 Mar.
Article in English | MEDLINE | ID: mdl-25453215

ABSTRACT

The objective of this study was to investigate the effect of key extraction parameters of extraction time (5-25 min), acid concentration (0-0.06 M HCl) and ultrasound amplitude (22.8-114 µm) on yields of bioactive compounds (total phenolics, fucose and uronic acid) from Ascophyllumnodosum. Response surface methodology was employed to optimize the extraction variables for bioactive compounds' yield. A second order polynomial model was fitted well to the extraction experimental data with (R(2)>0.79). Extraction yields of 143.12 mgGAE/gdb, 87.06 mg/gdb and 128.54 mg/gdb were obtained for total phenolics, fucose and uronic acid respectively at optimized extraction conditions of extraction time (25 min), acid concentration (0.03 M HCl) and ultrasonic amplitude (114 µm). Mass spectroscopy analysis of extracts show that ultrasound enhances the extraction of high molecular weight phenolic compounds from A. nodosum. This study demonstrates that ultrasound assisted extraction (UAE) can be employed to enhance extraction of bioactive compounds from seaweed.


Subject(s)
Ascophyllum/chemistry , Chemical Fractionation/methods , Fucose/isolation & purification , Phenols/isolation & purification , Seaweed/chemistry , Ultrasonics/methods , Uronic Acids/isolation & purification , Hydrochloric Acid/chemistry , Models, Theoretical , Statistics as Topic , Tannins/analysis , Tannins/isolation & purification , Time Factors
17.
Clin Chim Acta ; 438: 342-9, 2015 Jan 01.
Article in English | MEDLINE | ID: mdl-25261856

ABSTRACT

BACKGROUND: Amyotrophic Lateral Sclerosis (ALS) is a fatal neurodegenerative disease of the motor neuron for which no clinically validated biomarkers have been identified. METHODS: We have quantified by ELISA the biomarker phosphoneurofilament heavy chain (pNFH) in the cerebrospinal fluid (CSF) of ALS patients (n=29) and age-matched control patients with other diseases (n=19) by ELISA. Furthermore, we compared protein N-glycosylation of the CSF in ALS patients and controls, by applying a glycomics approach based on liquid chromatography and mass spectrometry. RESULTS: pNFH levels were significantly higher in ALS patients in comparison with controls (P<0.0001) in particular in fast progressors. The N-glycans found in the CSF were predominantly complex diantennary with sialic acid in α2,3- and α2,6-linkage, and bisecting N-acetylglucosamine-containing structures as well as peripherally fucosylated structures were found. As compared with controls the ALS group had a significant increase of a peak composed of the monosialylated diantennary glycans A2G2S(6)1 and FA2G2S(3)1 (P=0.0348). CONCLUSIONS: Our results underscore the value of pNFH as a biomarker in ALS. In addition, we identified a variation of the N-glycosylation pattern in ALS, suggesting that this change should be explored in future studies as potential biomarker.


Subject(s)
Amyotrophic Lateral Sclerosis/diagnosis , Neurofilament Proteins/cerebrospinal fluid , Phosphoproteins/cerebrospinal fluid , Acetylglucosamine/chemistry , Acetylglucosamine/isolation & purification , Adult , Aged , Amyotrophic Lateral Sclerosis/cerebrospinal fluid , Biomarkers/cerebrospinal fluid , Case-Control Studies , Chromatography, Liquid , Disease Progression , Enzyme-Linked Immunosorbent Assay , Female , Fucose/chemistry , Fucose/isolation & purification , Glycomics/instrumentation , Glycomics/methods , Glycosylation , Humans , Male , Mass Spectrometry , Middle Aged , Polysaccharides/chemistry , Polysaccharides/isolation & purification , Sialic Acids/chemistry , Sialic Acids/isolation & purification
18.
Carbohydr Polym ; 92(1): 503-9, 2013 Jan 30.
Article in English | MEDLINE | ID: mdl-23218327

ABSTRACT

A novel high molecular weight (1.1 × 10(6)Da) exopolysaccharide (EPS) produced by Enterobacter cloacae Z0206 strain was isolated by column chromatography. Complete hydrolysis of the EPS followed by gas chromatography mass spectrometry (GC-MS) and high performance liquid chromatography (HPLC) analyses showed that the EPS is composed of L-fucose, D-glucose, D-galactose, D-glucuronic acid and pyruvic acid in the approximate molar ratio of 2:1:3:1:1. Partial acid hydrolysis of the purified EPS followed by gel permeation chromatography (GPC) yielded a hexasaccharide. A combination of chemical analysis coupled with mass spectrometry and 1D and 2D NMR spectroscopy applied to the oligosaccharide showed that the EPS comprises a heptasaccharide repeating unit.


Subject(s)
Enterobacter cloacae/chemistry , Polysaccharides, Bacterial , Chromatography, High Pressure Liquid , Fucose/chemistry , Fucose/isolation & purification , Galactose/chemistry , Galactose/isolation & purification , Gas Chromatography-Mass Spectrometry , Glucose/chemistry , Glucose/isolation & purification , Glucuronic Acid/chemistry , Glucuronic Acid/isolation & purification , Hydrolysis , Magnetic Resonance Spectroscopy , Molecular Weight , Polysaccharides, Bacterial/chemistry , Polysaccharides, Bacterial/isolation & purification , Pyruvic Acid/chemistry , Pyruvic Acid/isolation & purification
19.
Mar Drugs ; 9(10): 2106-2130, 2011.
Article in English | MEDLINE | ID: mdl-22073012

ABSTRACT

Seaweeds--or marine macroalgae--notably brown seaweeds in the class Phaeophyceae, contain fucoidan. Fucoidan designates a group of certain fucose-containing sulfated polysaccharides (FCSPs) that have a backbone built of (1→3)-linked α-L-fucopyranosyl or of alternating (1→3)- and (1→4)-linked α-L-fucopyranosyl residues, but also include sulfated galactofucans with backbones built of (1→6)-ß-D-galacto- and/or (1→2)-ß-D-mannopyranosyl units with fucose or fuco-oligosaccharide branching, and/or glucuronic acid, xylose or glucose substitutions. These FCSPs offer several potentially beneficial bioactive functions for humans. The bioactive properties may vary depending on the source of seaweed, the compositional and structural traits, the content (charge density), distribution, and bonding of the sulfate substitutions, and the purity of the FCSP product. The preservation of the structural integrity of the FCSP molecules essentially depends on the extraction methodology which has a crucial, but partly overlooked, significance for obtaining the relevant structural features required for specific biological activities and for elucidating structure-function relations. The aim of this review is to provide information on the most recent developments in the chemistry of fucoidan/FCSPs emphasizing the significance of different extraction techniques for the structural composition and biological activity with particular focus on sulfate groups.


Subject(s)
Fucose/chemistry , Polysaccharides/chemistry , Seaweed/chemistry , Anticoagulants/chemistry , Anticoagulants/isolation & purification , Anticoagulants/pharmacology , Fibrinolytic Agents/chemistry , Fibrinolytic Agents/isolation & purification , Fibrinolytic Agents/pharmacology , Fucose/isolation & purification , Polysaccharides/isolation & purification , Polysaccharides/metabolism , Polysaccharides/pharmacology , Seaweed/metabolism , Seaweed/physiology , Structure-Activity Relationship , Sulfuric Acid Esters/chemistry , Sulfuric Acid Esters/isolation & purification , Sulfuric Acid Esters/pharmacology
20.
Zhongguo Zhong Yao Za Zhi ; 34(4): 419-22, 2009 Feb.
Article in Chinese | MEDLINE | ID: mdl-19459303

ABSTRACT

OBJECTIVE: To isolate and purify the polysaccharides from Radix Rehmanniae and analysis the monosaccharides composition. METHOD: The polysaccharides were extracted with hot water and precipitated by alcohol. Proteins in the precipitates were removed by TCA method. The products were further purified with column chromatography on Superdex 200 and Sephadex G100. The SRP I and SRP II were identified as homogeneous polysaccharide by HPLC, respectively, and then analyzed by GC after being hydrolysised. RESULT: Two homogeneous polysaccharides (SRP I and SRP II) were obtained from Radix Rehmanniae. CONCLUSION: SRP I contained rhamnose, arabinose, glucose and galactose in the percentage of 6.11%, 66.46%, 3.93% and 21.50%. SRP I was composed of rhamnose, fucose, mannose, galactose and fructose in the percentage of 21.82%, 24.47%, 10.48%, 29.94% and 13.29%.


Subject(s)
Chromatography, Gas/methods , Monosaccharides/isolation & purification , Scrophulariaceae/chemistry , Arabinose/chemistry , Arabinose/isolation & purification , Clinical Laboratory Techniques , Drugs, Chinese Herbal/analysis , Fructose/chemistry , Fructose/isolation & purification , Fucose/chemistry , Fucose/isolation & purification , Galactose/chemistry , Galactose/isolation & purification , Glucose/chemistry , Glucose/isolation & purification , Mannose/chemistry , Mannose/isolation & purification , Monosaccharides/chemistry , Plant Extracts/chemistry , Polysaccharides/chemistry , Polysaccharides/isolation & purification , Rhamnose/chemistry , Rhamnose/isolation & purification
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