Polysaccharides

A fucan sulphate found in brown marine algae (Phaeophyta-typically Fucus vesiculotus, Ascophyllum nodosum, Alaria and Lessonia nigrescens (illustrated) and has been shown to have anticoagulant activity. The main constituents are α-1,4 and α-1,2 linked L-fucose sulphates although galactose also occurs and there are many variations of the basic structure found in different species of Phaeophyta. The fucose content is approx. 26.2% and it also contains galactose (approx. 13.0%), uronic acid (approx. 13.0%) and sulfate (approx. 29.1%). The image was kindly provided by Prof Mike Guiry from Cork who runs ‘The Seaweed Site’.

A fucan sulphate found in brown marine algae (Phaeophyta-typically fucus vesiculosus (illustrated), Ascophyllum nodosum, Alaria and Macrocystis pyrifyra and has been shown to have anticoagulant activity. The main constituents are α-1,4 and α-1,2 linked L-fucose sulphates although galactose also occurs and there are many variations of the basic structure found in different species of Phaeophyta. The fucose content of this fucan is approx. 43.1% and it also contains galactose (approx. 8.8%), uronic acid (approx. 8.7%) and sulfate (approx. 30.6%). The image was kindly provided by Prof Mike Guiry from Cork who runs ‘The Seaweed Site’.

Chitosan from fungal cell walls.  It is made by treating cell walls of fungi (agaricus bisporus) with sodium hydroxide.Viscosity typically 20-100 mPa.s

Cellulose is a linear polysaccharide of β 1-4 linked glucose residues. The polysaccharide chains are bundled as microfibrils in cell walls and provide the essential structural components within growing plants. Each microfibril exhibits a high degree of three-dimensional internal bonding resulting in a crystalline structure that is insoluble in water, resistant to reagents and very strong.

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This β-glucan contain D-glucose residues with β-1,3 links and b-1-6 side branches. The frequency, location, and length of the sidechains may play a role in immunomodulation. Differences in molecular weight, shape, and structure of β-glucans can also affect the differences in biological activity. The water-soluble β-D-glucan is extracted from fruiting bodies of Piptoporus betulinus by hot aqueous extraction, followed by freeze-thawing and dialysis. Methylation analysis and NMR spectroscopy, indicated the presence of a β-D-glucan with a main chain (1,3)-linked, substituted at O-6 by single glucose residues. The image was kindly provided by Dr. Chris Lawson.

The polysaccharide has a linear structure and consists predominantly of repeating trisaccharide units, -O-(3-D-mannuronic acid-(1,4)-O-(3-D-glucopyranosyl-(1,4)-D-galactose. 50% of the hydroxyl groups are acetylated.  Extracted from a gram negative non pathogenic bacteria and then synthetic manipulation.

A fucan sulphate found in brown marine algae (Phaeophyta-typically Fucus serratus, Ascophyllum nodosum, Laminaria japonica (illustrated) and Macrocystis pyrifyra) and has been shown to have anticoagulant activity. The main constituents are α-1,4 and α-1,2 linked L-fucose sulphates although galactose also occurs and there are many variations of the basic structure found in different species of Phaeophyta. Fucoidan ≥ 95.0% Organic SO42- ≥ 20.0% Carbohydrate ≥ 70.0% L-Fucose ≥ 23.0% Alginic Acid ≤ 31.0%  The image was kindly provided by Prof Mike Guiry from Cork who runs ‘The Seaweed Site’.

Fucogalactan (GFS) is a polysaccharide isolated and purified from the brown seaweed Undaria pinnatifida. The polysaccharide is a sulphated galactose containing fucan. Fucogalactan is currently under investigation for possible therapeutic indications including anti-inflammatory properties, immuno- modulating activities, inhibition of tumor growth, stem cell replentishment, antiviral activity, dementia and ulcer healing. The image was kindly provided by Prof Mike Guiry from Cork who runs ‘The Seaweed Site’.

Gycosaminoglycan in many organs; joint lubricant and shock absorber

Applications Isomaltopentaose, is an isomalto-oligosaccharides (IMO) compound, used as functional food ingredients. References Hu, Y., et al.: Lett. App. Microbio., 57, 108 (2013);

Lambda-Carrageenan is a non-gelling sulphated galactan extracted from red seaweed (typically Gigartina stellata and Chondrus crispus). The structure of all carrageenans consists of a strictly alternating masked repeating unit of 1,3-linked α-D-galactose and 1,4-linked β-D-galactose. λ-Carrageenan has the α-linked unit 2-6-disulphated and the β-linked unit is 2-sulphated. The image was kindly provided by Prof Mike Guiry from Cork who runs ‘The Seaweed Site’.

Pectic acid is non water-soluble β (1,4)-linked polygalacturonic acid. In its gel form, is water-soluble, transparent and gelatinous, and exists in ripe fruit and some vegetables. It is a product of pectin degradation in plants, and is produced via the interaction between pectinase and pectin (the latter being common in the wine-making industry).

Xyloglucans are members of a group of polysaccharides typically refered to as hemicelluloses. Hemicelluloses are plant cell wall polysaccharides that are not solubilized by water but are solubilized by aqueous alkali (e.g. 1 and 4M KOH). Other hemicellulosic polysaccharides include xylan, glucuronoxylan, arabinoxylan, mannan, glucomannan and galactoglucomannan. Hemicelluloses have a backbone of 1,4-linked β-D-pyranosyl residues in which O4 is in the equatorial orientation (e.g. Glc, Man, and Xyl). Xyloglucan is the predominant hemicellulose in the primary walls of dicots and non-graminaceous monocots and may account for up to 20% of the dry weight of the primary wall. Xyloglucan has a backbone composed of 1,4-linked β-D-Glcp residues. Up to 75% of these residues are substituted at O6 with mono-, di-, or triglycosyl side chains.

Carboxymethyl chitosan has good solubility in water and unique chemical, physical and biological properties such as high viscosity, large hydrodynamic volume, low toxicity, biocompatibility and good ability to form films, fibres and hydrogels. For this reason, it has been extensively used in many biomedical fields such as a moisture-retention agent, bactericide, wound dressing agent, in artificial bone and skin, as blood anticoagulant and as a component in different drug delivery matrices. The reactive ligands COOH and NH2 groups are available for metal chelation and dye binding.

The extracellular polysaccharide produced by Arthrobacter stabilis NRRL B-3225 contains D-glucose, D-galactose, pyruvic acid, O-succinyl, and O-acetyl in the approximate molar ratio of 6:3:1:1:1.5. Succinyl is linked as its half-ester, making it readily removable. The viscosity of aqueous, salt-free solutions of both native and deacylated polymer is relatively low, but atypical of anionic polysaccharides, increases rapidly in the presence of salts, acids, or alkali.

In water, hydroxypropyl cellulose forms liquid crystals with many mesophases depending on concentration. These mesophases include isotropic, anisotropic, nematic and cholesteric, the latter resulting in many colors such as violet, green and red. Pharmaceutical applications include treatments for medical conditions such as dry eye syndrome (keratoconjunctivitis sicca), recurrent corneal erosions, decreased corneal sensitivity, exposure and neuroparalytic keratitis. It is also used as a binder in tablets. Hydroxypropylcellulose is also used as a thickener, a binder and emulsion stabiliser in foods with E number E463.  HPC is used as a support matrix for DNA separations by capillary and microchip electrophoresis.

Quaternization of the primary amine in N-Trimethylchitosan increases the water solubility of chitosan and keeps chitosan soluble over a wide pH range. N-Trimethylchitosan is soluble in water and ethanol, making it ideal for use in biotechnology applications.The degree of quaternization is 30-70%

Fluorescein isothiocyanate carboxymethyl dextran (FITC-CM Dextran) has been reported to provide a valuable carrier for nanoparticles of iron oxide.  These products provide a potent tool for contrast enhancement in magnetic resonance imaging.

Cellulose derivative, food thickener and emulsifier, bulk forming laxative

Viscoelastic polymer; excipient; food additive

Gycosaminoglycan in many organs; joint lubricant and shock absorber

Viscoelastic polymer; excipient; food additive

Applications Labelled Sucrose (S697000). Yuanzhen sugar is a polysaccharide polymer, containing a certain amount of fructooligosaccharides. References Watanabe, T., et al.: Biosci. Biotech. Biochem., 72, 3167 (2008), You, Y., et al.: J. Agric. Food Chem., 57, 709 (2009),

Rhodamine dextran (RD) is widely used as both an anterograde and retrograde tracer in neurons and for numerous other applications. It is biologically rather inert having α-1,6-linked glucose residues resistant to cleavage by most endogenous cellular glycosidases. It has low immunogenicity and makes an ideal long-term tracer for live cells. RD also serves as a valuable marker for cell loading of macromolecules by micro-injection, vesicular fusion, and electroporation, as well as for the uptake and internal processing of exogenous materials by phagocytotic and endocytic pathways.

DEAE-Dextran hydrochloride (DEAE-D) is a positively-charged dextran derivative that can be used for vaccine production, gene therapy, protein stabilisation, dyslipidemia prevention, as flocculating agent, and many other applications. DEAE-D is also used for transfecting animal cells with foreign DNA.  DEAE-Sepharose, DEAE-650 and DEAE-Sephadex are commonly used in chromatography for the separation of biological molecules such as proteins and carbohydrates.

Sodium carboxymethyl dextran is a white, odourless and tasteless powder, which is freely soluble in water or electrolyte solutions. Applications that have been described for carboxymethyl dextran include carriers of paramagnetic contrast agents, preparation of conjugates of pharmacologically active compounds and carboxymethyl dextrans in biosensors.  A number of other uses in cosmetics, agriculture, foods, paints and textiles have been the subject of patent applications.

Cellulose acetate fiber is one of the earliest synthetic fibers and is based on cotton or tree pulp cellulose. Cellulose acetate is used as a film base in photography, as a component in some coatings, and as a frame material for eyeglasses.  It is also used as a synthetic fiber in the manufacture of cigarette filters and playing cards. In photographic film, cellulose acetate replaced nitrate film in the 1950s, being far less flammable and cheaper to produce but in recent years has been rendered obsolete by the advent of digital cameras.

Sephadex G-50 is a highly purified, high molecular weight, cellulose-based polymer that is used as a solid support in chromatography. The size of the gel particles can be varied by changing the concentration of the gel solution. It has a number of different uses, such as purification of proteins and other macromolecules, separation of DNA fragments, and the enzymatic synthesis of oligosaccharides. Sephadex G-50 is a synthetic material that is modified with organic or inorganic compounds to increase its chemical reactivity. This product can also be used for glycosylation and methylation reactions.

Ulvans are structural polysaccharides present in the cell walls of green algae such as Ulva armoricana, Ulva rotondata, Ulva rigida, Ulva lacterca and Ulva pertusa. They are highly sulphated and contain rhamnose 3-sulphate, xylose, xylose 2-sulphate, glucuronic acid and iduronic acid residues.  Ulvan has several potentially valuable functionalities such as gel formation for agricultural and food applications. It has also an anticoagulant, antioxidant, antihyperlipidemic and antitumor activities that are attractive for pharmaceutical applications. The image was kindly provided by Prof Mike Guiry from Cork who runs ‘The Seaweed Site’.

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Gum arabic is an exudate gum picked from Acacia trees growing in tropical arid regions (typically Acacia senegal and Acacia laetia). The polysaccharide is branched with a main chain of (1-3) linked β-D-galactopyranosyl units with side chains of (1-3) β-D-galactopyranosyl units joined to it by (1-6) links. The side chains are 2-5 units in length. Both the main chain and the side chains have attached units of α-L-arabinofuranosyl, α-L-rhamnopyranosyl, β-D-glucuronopyranosyl and 4-O-methyl-β-D-glucuronopyranosyl units.

Propylene glycol alginate is a reaction product of propylene oxide and alginic acid. At the 49th JECFA meeting (1997) it was resolved that the total dietary propylene glycol intake from all sources should be allocated an ADI of 0-25 mg/kg.  Applications include as a stabiliser in beer foam due to electrostatic interaction between carboxyl groups on the glycol alginate molecules and amino groups on the peptides in the bubble wall and in ice cream by emulsifying the fat.Esterification is greater then 80%Viscosity (1% aq solution): 200-300 mpa.s

Applications D-(+)-Cellopentaose (cas# 2240-27-9) is a compound useful in organic synthesis.

N-Acetyl-de-O-sulphated heparin is a glycosaminoglycan, which occurs in many mammalian tissues and has important anticoagulant and thrombolytic properties. The chemical structure is composed mainly of two disaccharide repeating units A and B. A is L-iduronic acid 2-suplhate linked α-(1,4) to 2-deoxy-2-sulfamido-D-galactose 6-sulphate, while B is D-glucuronic acid β-(1,4) linked to 2-deoxy-2-sulfamido-D-glucose 6-sulphate.

Furcellaran (Danish agar) is similar to κ-carrageenan but is less sulphated (50%). It has been extracted from Furcellaria lumbricalis, which is mainly harvested off the coast of Denmark. This species, which is common to most parts of Europe, occurs as a loose form and only reproduces vegetatively. The image was kindly provided by Prof Mike Guiry from Cork who runs ‘The Seaweed Site’.

Gum ghatti is an exudate gum from the tree Anogeissus latifolia found in India and Sri Lanka. Applications are similar to Gum arabic in the food and pharmaceutical industries, where it is used as an emulsifier. The polysaccharide is reported to have an extremely complex structure which contains both oligosaccharides and polysaccharide elements. The polysaccharide contains Ara, Gal, Man, GlcA and Rha in a molar ratio of 61:39:6:10:6, a backbone of (1,6)-linked β-D-galactopyranosyl units and side chains of L-arabinofuranose units with some (1,4)-D-glucopyranosyluronic acid units, some joining (1,2)-D-mannopyranosyl units.

Sodium carboxymethyl dextran (CM-dextran) is a white, odourless and tasteless powder, which is freely soluble in water or electrolyte solutions. The product has a pronounced polyanionic character, due to the high degree of carboxyl substitution.  Applications that have been described for CM-dextran include carriers of paramagnetic contrast agents, preparation of conjugates of pharmacologically active compounds and CM-dextrans in biosensors.  A number of other uses in cosmetics, agriculture, foods, paints and textiles have been the subject of patent applications.

Carboxymethyl cellulose is used in food as a viscosity modifier, thickener, to stabilise emulsions and are found in gluten-free and reduced-fat products. It is also a constituent of toothpaste, laxatives, diet pills, water-based paints, detergents, textile sizing, and various paper products.  In laundry detergents, it is used as a soil suspension polymer. It is also used in pharmaceuticals as a thickening agent and in the oil-drilling industry as a viscosity modifier and water-retaining agent.

‘Water kefir’ is a home-made beverage, which was thought to contain significant amounts of bacterial exopolysaccharides. It has now been reported that the exopolysaccharide fraction of this material contains dextrans with similar structures, having a number of (1,3) linkages, branched at positions O3 and position O2 and with a wide range of molecular weights.  In addition, it was shown that a small amount of levan is also present.

Chitosan is the deacetylated form of chitin.  The polysaccharide is deacetylated in order to render it soluble, which is then possible at pH values of less than 7 (normally in dilute acid).  This then allows the material to be used in a number of industrial applications as a binder and film former.

Cellulose acetate phthalate (CAP) finds use in the formulation of pharmaceuticals, such as the enteric coating of tablets or capsules and for controlled release formulations, where it is often used with other coating agents such as ethyl cellulose.  It contains about 50% acetate and 25% as the phthalate ester with the rest as free hydroxyl groups.  Enteric coatings based on CAP are resistant to acidic gastric fluids, but easily soluble in mildly basic medium of the intestine. The pH-sensitive solubility of CAP is mainly determined (as are other properties of this mixed ester) by the degree of substitution and by the molar ratio (acetyl and phthaloyl groups).

DEAE-Dextran (DEAE-D) is a positively-charged dextran derivative that can be used for vaccine production, gene therapy, protein stabilisation, dyslipidemia prevention, flocculating agents, and many other applications. DEAE-D is also used for transfecting animal cells with foreign DNA.  DEAE-Sepharose, DEAE-650 and DEAE-Sephadex are commonly used in chromatography for the separation of biological molecules such as proteins and carbohydrates.

Locust bean (carob) gum is the refined endosperm of the seed of the carob tree, an evergreen of the legume family (Ceretonia siliqua). The tree grows extensively in Spain and is cultivated in many other Mediterranean countries. Locust bean gum, like guar gum, is a galactomannan with a backbone of (1,4) β-D-mannopyranosyl units having branches of (1,6)-linked α-D-galactopyranosyl units. However, locust bean gum has substantially fewer side chains than guar gum and these are clustered in blocks leaving longer regions of unsubstituted mannosyl regions. The gum is only partially soluble in water and suspensions require heating before solubility is achieved. As with guar, the polysaccharide forms gels with other gums such as carrageenan and xanthan. Applications are in the food industry to enhance texture, in paper making and in the textile industry.