Polysaccharides

Gum Jhingan is a modified carbohydrate with a fluorinated saccharide. It is an oligosaccharide that has been synthesized from the sugar galactose. Gum Jhingan is a high-purity, custom-synthesized product that has been methylated and glycosylated. The modification process of this carbohydrate includes fluorination and click chemistry.

Xanthan gum is a polysaccharide produced by the Gram negative bacteria Xanthomonas campestris. It has unique rheological and gel forming properties and finds many applications particularly in the food and oil industries. Recently, it has been shown that ternary mixtures of konjac glucomannan, xanthan gum and sodium alginate can form a non-covalently linked complex which exhibits enhanced rheological properties of value in, for example, functional foods. The structure of xanthan is based on a cellulosic backbone of β-(1,4)-linked glucose units which have a trisaccharide side chain of mannose-glucuronic acid-mannose linked to every second glucose unit in the main chain. Some terminal mannose units are pyruvylated and some of the inner mannose units are acetylated.

Applications 3-O-Methyl-d3 Quercetin is the labeled analogue of 3-O-Methyl Quercetin (M326545), a metabolite of the flavanoid Quercetin (Q509500) with inhibitory activity on lipopolysaccharide-induced activation of macrophage U937 cells. Not a dangerous good if item is equal to or less than 1g/ml and there is less than 100g/ml in the package References Okoko, T. et al.: Food Chem. Toxicol., 47, 809 (2009); Duenas, M. et al.: Eur. Food Res. Technol., 232, 103 (2011); Marzouk, M. et al.: Phytochem., 52, 943 (1999)

Dextran sulphate is a dextran derivative whose ulcer (colitis) -causing properties were first reported in hamsters and extrapolated a few years later to mice and rats. The exact mechanisms through which dextran sulphate induces intestinal inflammation are unclear but may be the result of direct damage of the monolayer of epithelial cells in the colon, leading to the crossing of intestinal contents (for e.g. commensal bacteria and their products) into underlying tissue and therefore induction of inflammation.  The dextran sulphate sodium induced ulceration model in laboratory animals has some advantages, when compared to other animal models of colitis, due to its simplicity and similarities to human inflammatory bowel disease.

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 and possible anticoagulant, antioxidant, antihyperlipidemic and antitumoral activities for pharmaceutical applications. The image was kindly provided by Prof Mike Guiry from Cork who runs ‘The Seaweed Site’.

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.

Anterograde and retrograde tracer in neurons; biologically inert

A fucan sulphate found in brown marine algae (Phaeophyta-typically Fucus serratus, Ascophyllum nodosum, Laminaria digitata (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. The image was kindly provided by Prof Mike Guiry from Cork who runs ‘The Seaweed Site’.

An apiose-rich pectic polysaccharide zosterin is found in the sea grass Zostera marina and is typical of similar structures occurring in higher plants. The structure consists of an α-1,4-D-galactopyranosyluronan backbone substituted by 1,2-linked apiofuranose oligosaccharides and single apiose residues. The average molecular mass of the polysaccharide has been shown to be about 4100 Da with a low polydispersity.

Gycosaminoglycan in many organs; joint lubricant and shock absorber

Curdlan is a microbial polysaccharide produced by a mutant strain of Alcaligenes faecalis var. myxogenes which was first shown to produce succinoglucan prior to mutation. Curdlan is a β-1,3 glucan forming clear solutions at about 55 °C which then gels (“low-set”) when cooled. Suspensions of curdlan at higher temperatures form firm resilient gels (“high set”) that melt at 140 - 160 °C. The image was kindly provided by Dr. Chris Lawson.

Colominic acid (polysialic acid) is a linear small polysaccharide containing α-2,8-linked sialic acid (neurominic acid) with (n = 8 to >100) residues. Polysialic acid is an unusual post translational modification polysaccharide that is widely expressed in nature in bacterial capsules, fish, sea urchin eggs, embryonic tissues, amphibians, animal and human brains, and in a various cancers.  The major carrier of polysialic acids in mammals is the neural cell adhesion molecule (a glycoprotein that belongs to the immunoglobulin superfamily).Average molecular weight for this product is :50000-60000

Food additive, applied in pharmaceuticals and beauty products.

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.

Fluorescein dextran (FD) 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. FD 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.

Pullulan is a glucan elaborated by the fungus Aureobasidium pullulans. The chemical structure is essentially repeating units of maltotriose joined by α-1,6 linkages. Pullulan dissolves readily in water to form stable, viscous solutions that do not gel. The polysaccharide can be moulded, made into fibres and forms clear soluble films. Applications are in foods as a low calorie ingredient and the polysaccharide forms water soluble films that have been used as seed coatings and to coat fruit. Pullulan can also be used in industrial applications as a binder, film former and in pharmaceutical applications.  Average MW is typically 100-200kDa.  Viscosity is ca 120 mm2/s. The image was kindly provided by Dr. Chris Lawson.

A fucan sulphate found in brown marine algae (Phaeophyta-typically Fucus vesiculotus, Durvillea (illustrated), Alaria and Cladosiphon) 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 approximately 27.9% and it also contains galactose (approx. 6.2%), uronic acid (approx. 22.4%) and sulfate (approx. 21.4%). 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 vesiculotus, Ecklonia (illustrated), Alaria and Cladosiphon) 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. 19.0% and it also contains galactose (approx. 12.0%), uronic acid (approx. 25.5%) and sulfate (approx. 19.1%). 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

The disaccharide repeating unit of chondroitin sulphate consists of N-acetyl galactosamine sulphate linked β1,4 to glucuronic acid. Each monosaccharide may be left unsulphated, sulphated once, or sulphated twice. The most common pattern is that the hydroxyl groups of the 4 and 6 positions of the N-acetyl-galactosamine are sulphated, with some chains having the position 2 of the glucuronic acid sulphated.

Hypromellose phthalate (hydroxypropyl methylcellulose phthalate, or HPMCP) is a phthalic acid ester of hydroxypropyl methylcellulose.  Hypromellose phthalate was introduced in 1971 as a cellulose derivative for enteric coatings, used to protect drugs from degradation by gastric acid or to prevent them from causing side effects in the stomach.  HPMCP is also used in sustained-release preparations, in binders and as microcapsule bases.

Poria cocos is an edible medicinal fungus known as “Fuling” in Chinese that has been used as a Chinese traditional medicine for more than two thousand years. Polysaccharide material is the most abundant organic substance in the fungus, accounting for about 85% of the total and is a mixture of polysaccharides with the major component being Pachyman, a β-glucan with a 1,3 backbone and 1,6 side chains. It is reported that Pachyman has a wide range of biological activities including antitumour, immunomodulatory, anti-inflammatory and antioxidative properties. Pachyman is a beta-glucan with a 1,3 backbone and 1,6 side chains of fungal origin (Poria cocos). The image was kindly provided by Dr. Chris Lawson.

Hydroxypropyl methylcellulose (HPMC or hypromellose) is a semisynthetic, inert and viscoelastic polymer that is used as eye drops and as semi-synthetic substitute for tear-films. When applied, a hypromellose solution acts to swell and absorb water, by increasing the thickness of the tear-film, resulting in decreased eye irritation.  In addition to its use in ophthalmic liquids, hypromellose has been used as an excipient in oral tablet and capsule formulations, where, depending on the grade, it functions as controlled-release agent. It is also used as a binder and as a component of tablet coatings.  Hypromellose in aqueous solution, unlike methylcellulose, exhibits thermal gelation properties. HPMC is approved as a food additive, emulsifier, thickening and suspending agent, and as an alternative to animal gelatin (Codex Alimentarius code (E number) is E464).

Chromogenic substrate for the measurement of endo-inulinase

Dextran is α-(1,6)-linked α-D-glucan with α-(1,3)-linked glucose branch points produced by fermentation of Leuconostoc mesenteroides via the action of the enzyme dextransucrase on sucrose.  The main use for native dextran is as an extender in blood transfusions and products having a range of sharp cut-off molecular weights are produced commercially for this and other applications.  A complex of iron with dextran, known as iron dextran, is used as a source of iron for baby piglets which are often anaemic at birth.

Stability Hygroscopic Applications Maltopentaose is a maltooligosaccharide that is used for research and diagnostic purposes. They can also be used in nutrients and healthcare. References Ezure, Y. et al.: Biosci. Biotech. Biochem., 61, 1931 (1997); Hatonen, K. et al.: Am. J. Clin. Nutr., 96, 44 (2012);

Produced from starch; white hygroscopic spray-dried powder; easily digestible

Konjac glucomannan is an acetylated (1,4)-β-D-glucomannan obtained from the tubers of Amorphophallus konjac or Konnyaku root. It is widely used in foods, pharmaceuticals paints and explosives. It has been shown that ternary mixtures of konjac glucomannan, xanthan gum and sodium alginate can form a non-covalently linked complex which exhibits enhanced rheological properties of value in, for example, functional foods.

Gycosaminoglycan in many organs; joint lubricant and shock absorber

N-Acetyl 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.

Hyaluronic acid, a polysaccharide with alternating β (1,3) glucuronide and β (1,4) glucosamine residues labelled with 5-amino-fluorescein gives a yellow fibrous product, which is soluble in both water and electrolytes.  Fluorescein-labelled hyaluronic acid can be used as a probe to follow the fate of hyaluronan in vitro and greatly enhances the visualisation of the permeation of substrates through skin and other tissues. Other applications of fluorescein-labelled hyaluronic acid have been reported in cancer research.

Ivory nut mannan occurs in members of the custard apple, ebony and palm families - Ivory nut. The polysaccharide contains more than 95% mannose units linked β-(1,4) with a few a-D-galactopyranosyl units linked (1,6). It is widely used in foods, pharmaceuticals paints and explosives.

Dextran sulphate is a dextran derivative whose ulcer (colitis) -causing properties were first reported in hamsters and extrapolated a few years later to mice and rats. The exact mechanisms through which dextran sulphate induces intestinal inflammation are unclear but may be the result of direct damage of the monolayer of epithelial cells in the colon, leading to the crossing of intestinal contents (for e.g. commensal bacteria and their products) into underlying tissue and therefore induction of inflammation.  The dextran sulphate sodium induced ulceration model in laboratory animals has some advantages, when compared to other animal models of colitis, due to its simplicity and similarities to human inflammatory bowel disease.

The sodium salt of hyaluronic acid is a glycosaminoglycan found in many organs, where it functions as a joint lubricant and shock absorber. It is obtained principally from synovial fluid, vitreous humor of the eye, umbilical tissue and cocks comb. The chemical structure of hyaluronic is a disaccharide repeat of β-(1,3) glucuronic acid and β-(1,4) N-acetyl glucosamine.

A fucan sulphate found in brown marine algae (Phaeophyta-typically Fucus vesiculotus, Ascophyllum nodosum, Alaria and Macrocystis pyrifyra (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 of this fucan is approx. 31% and it also contains galactose (approx. 2.2%), uronic acid (approx. 12.4%) and sulfate (approx. 32.5%). The image was kindly provided by Prof Mike Guiry from Cork who runs ‘The Seaweed Site’.

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.

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.

Dextran is α-(1,6)-linked α-D-glucan produced by fermentation of Leuconostoc mesenteroides via the action of the enzyme dextransucrase on sucrose. The main use for native dextran is as a blood plasma extender in blood transfusions. A complex of iron with dextran, known as iron dextran, is used as a source of iron to baby piglets which are often anaemic at birth.

Dextran is α-(1,6)-linked α-D-glucan with α-(1,3)-linked glucose branch points produced by fermentation of Leuconostoc mesenteroides via the action of the enzyme dextransucrase on sucrose.  The main use for native dextran is as an extender in blood transfusions and products having a range of sharp cut-off molecular weights are produced commercially for this and other applications.  A complex of iron with dextran, known as iron dextran, is used as a source of iron for baby piglets which are often anaemic at birth.

Cellulose with a particle size of 20μm is an industrial biomass material that has various applications. It is commonly used in the production of paper, textiles, and biofuels. Cellulose is a complex carbohydrate that provides structural support to plant cell walls. It can also be used as an excipient in pharmaceutical formulations, such as in the production of tablets. In addition to its industrial uses, cellulose has been studied for its antioxidant activity. It has been found to inhibit lipid peroxidation, which is a process that can lead to oxidative damage in cells. This antioxidant property makes cellulose a potential ingredient in skincare products or dietary supplements aimed at promoting overall health and well-being. Cellulose can be extracted from various sources, including wood pulp and agricultural waste. It is typically processed using solvents like chloroform or methanol to remove impurities and obtain a pure form of cellulose. With its versatility and wide range of applications, cellulose with a particle size

Iota-Carageenan is a gelling sulphated galactan extracted from red seaweed (typically Euchuma cottonii and Euchuma spinosum). 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. The α-linked galactose occurs as a 3,6-anhydro-2-sulphate unit and the β-linked sugar occurs as the 4-sulphate. The image was kindly provided by Prof Mike Guiry from Cork who runs ‘The Seaweed Site’.

Octyl-agarose is a type of agarose gel that has been modified to contain 20% ethanol solution. It is used in the purification of oligosaccharides and monosaccharides, as well as in the synthesis of complex carbohydrate. Octyl-agarose can be custom synthesized or modified with glycosylation, methylation, sugar, or carbohydrate modifications.