WO2001082724A2 - Compositions contenant des aminopolysaccharides et des polysaccharides charges negativement - Google Patents

Compositions contenant des aminopolysaccharides et des polysaccharides charges negativement Download PDF

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Publication number
WO2001082724A2
WO2001082724A2 PCT/IB2001/001044 IB0101044W WO0182724A2 WO 2001082724 A2 WO2001082724 A2 WO 2001082724A2 IB 0101044 W IB0101044 W IB 0101044W WO 0182724 A2 WO0182724 A2 WO 0182724A2
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Prior art keywords
chitosan
composition
polysaccharide
negatively charged
particles
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PCT/IB2001/001044
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English (en)
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WO2001082724A3 (fr
Inventor
Jan Remmereit
Jo Klaveness
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Natural As
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Priority to AU2001262596A priority Critical patent/AU2001262596A1/en
Publication of WO2001082724A2 publication Critical patent/WO2001082724A2/fr
Publication of WO2001082724A3 publication Critical patent/WO2001082724A3/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/20—Reducing nutritive value; Dietetic products with reduced nutritive value
    • A23L33/21—Addition of substantially indigestible substances, e.g. dietary fibres
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
    • A23L29/20—Foods or foodstuffs containing additives; Preparation or treatment thereof containing gelling or thickening agents
    • A23L29/269—Foods or foodstuffs containing additives; Preparation or treatment thereof containing gelling or thickening agents of microbial origin, e.g. xanthan or dextran
    • A23L29/27—Xanthan not combined with other microbial gums
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
    • A23L29/20—Foods or foodstuffs containing additives; Preparation or treatment thereof containing gelling or thickening agents
    • A23L29/275—Foods or foodstuffs containing additives; Preparation or treatment thereof containing gelling or thickening agents of animal origin, e.g. chitin
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs

Definitions

  • the present invention relates to compositions including a positively charged polysaccharide (e.g. , aminopolysaccharide) and a negatively charged polysaccharide that are readily dispersable in aqueous solution. These compositions are suitable for use as dietary supplements.
  • a positively charged polysaccharide e.g. , aminopolysaccharide
  • a negatively charged polysaccharide that are readily dispersable in aqueous solution.
  • dietary fiber has been recommended for a variety of indications, including reduction of serum cholesterol, reduction of the risk of coronary heart disease, reduction in blood pressure, enhanced weight control, better glycemic control, and reduced risk of cancers such as colon cancer.
  • An increase in dietary fiber has been recommended for a variety of indications, including reduction of serum cholesterol, reduction of the risk of coronary heart disease, reduction in blood pressure, enhanced weight control, better glycemic control, and reduced risk of cancers such as colon cancer.
  • Anderson and Hanna J. Nutr. 129(7 Suppl.):1457S-66S [1999]
  • Anderson et al. Am. J. Clin. Nutr. 59(5 Suppl.):1242S-1247S [1994]
  • Jenkins et al. J. Am. Coll. Nutr. 17(6):609-16 [1998]
  • Behall Ann. N.Y. Acad. Sci. 819:142-54 [1997]
  • chitosan for the reduction of serum cholesterol and blood lipids has also been described.
  • the recommended doses are between 3 and 12 grams before each meal.
  • the recommended dose is equivalent to up to 12 tablets, which causes great inconvenience to the user.
  • chitosan only dissolves at acidic pH values, it does not disperse or dissolve in most liquids. Therefore, chitosan mixed in non-acidic liquids settles out rapidly and imparts a gritty, unpleasant texture and poor mouthfeel.
  • compositions containing sources of dietary fiber (e.g., chitosan) and other carbohydrates that are dispersable in liquids, palatable, and have an acceptable mouthfeel.
  • the compositions are dispersable in the liquid at concentrations that provide an acceptable daily intake of the fiber or other carbohydrate.
  • the present invention relates to a readily dispersable composition that includes at least one positively charged polysaccharide (e.g., and aminopolysaccharide) and at least one negatively charged polysaccharide.
  • the present invention provides a composition comprising a positively charged aminopolysaccharide and a negatively charged polysaccharide, wherein the composition is formed into a particle.
  • the particle is dispersable in water.
  • the particle binds substances having a log P of greater than about 1.5.
  • the aminopolysaccharide is selected from chitosan, chitosan derivatives, amino substituted cellulose, or combinations thereof.
  • the negatively charged polysaccharide is selected from xanthan, guar gum, carrageenan, pectin, alginic acid, and combinations thereof. In some particularly preferred embodiments, the polysaccharide is xanthan. In some embodiments, the particle comprises greater than about 50% chitosan, while in other embodiments, the particle comprises greater than about 60% chitosan, 70% chitosan, 80% chitosan, 90% chitosan, or 99% chitosan. In some embodiments, the chitosan is a physiologically acceptable salt. In other embodiments, the particle further comprises a food additive selected from flavorings, colors, vitamins, minerals, fragrances, and phytonutrients.
  • the composition remains dispersed in a liquid after stirring.
  • the dispersion is a colloid.
  • the particles further comprise an additional anionic compound (e.g., DNA, RNA, or an anionic drug).
  • the present invention provides a method comprising: a) providing an aminopolysaccharide, a negatively charged polysaccharide, and a liquid; b) combining the aminopolysaccharide, negatively charged polysaccharide, and liquid to form a mixture; and c) blending the mixture under conditions such that particles containing the aminopolysaccharide and negatively charged polysaccharide are formed.
  • the particles bind compounds having a log P of greater than about 1.5.
  • the negatively charged polysaccharide is selected from xanthan, guar gum, carrageenan, pectin, and alginic acid.
  • the particle comprises greater than about 50% chitosan, while in other embodiments, the particle comprises greater than about 60% chitosan, 70% chitosan, 80% chitosan, 90% chitosan, or 99% chitosan.
  • the chitosan is a salt.
  • the particle further comprises a food additive selected from flavorings, colors, vitamins, minerals, fragrances, and phytonutrients. In some particularly preferred embodiments, the composition remains dispersed in a liquid after stirring.
  • chitosan refers to co-polymers such as ⁇ -1— »4-linked 2-acetamido-2- deoxy-D-glucopyranose and ⁇ -1— »4-linked 2-amido-2-deoxy-D-glucopyranose formed by deacetylating chitin. It will be recognized that the level of deacetylation of chitin may vary so that the term “chitosan” encompasses any deacetylated chitin (e.g., deacetylated by at least forty percent to eighty percent, and in some instances to as much as ninety percent or ninety-five percent).
  • chitosan salt refers to those salts formed by the reaction of chitosan and an acid, such as an organic acid or an inorganic acid (e.g., as described in U.S. Pat. No. 5,599,916, incorporated herein by reference).
  • an acid such as an organic acid or an inorganic acid (e.g., as described in U.S. Pat. No. 5,599,916, incorporated herein by reference).
  • examples of chitosan salts formed with an inorganic acid include, but are not limited to, chitosan hydrochloride, chitosan hydrobromide, chitosan phosphate, and mixtures thereof.
  • chitosan salts formed with an organic acid include, but are not limited to, salts of acetate adipate, benzene sulphonate, bromide, camsylate, chloride, citrate, glucuronate, hippurate, iodide, lactate, maleate, mesylate, napsulate, nitrate, oleate and other fatty acid anions including omega 3 and conjugated linoleic acid, as well as phosphate, succinate, sulphate, tartrate, and tosylate, and mixtures thereof.
  • Chitosan salts produced using a mixture of acids including, for example, both inorganic and organic acids are also encompassed by this definition.
  • Salts formed with nucleic acids such as DNA and anionic drugs such as COX-2 inhibitors, anionic steroid derivatives (e.g., hydrocortisone hemisuccinate), and other drug anions for treatment of infections, cardiovascular diseases, diabetes, cancer, or asthma are also encompassed by the definition.
  • chitosan derivative refers to derivatives formed by the reaction of chitosan with another chemical compound, including, but not limited to compounds such as aromatic aldehydes (e.g., sahcylaldehyde, 3-formyl-2-hydroxybenzoic acid, pyridine aldehydes, etc.), aldoses and ketoses (e.g., glucose, galactose, arabinose, xylose, N-acetylglucosamine, lactose and maltose) so that a chemical group not normally present in chitosan is covalently attached to the chitosan molecule.
  • aromatic aldehydes e.g., sahcylaldehyde, 3-formyl-2-hydroxybenzoic acid, pyridine aldehydes, etc.
  • ketoses e.g., glucose, galactose, arabinose, xylose, N-acetylglucosamine, lacto
  • Chemical modifications creating chitosan derivatives can in general involve any chemical modification of one or more alcohol groups or one or more amino groups. These groups can be removed and replaced with substitute groups and/or optionally reacted with chemical groups in other compounds or directly reacted with other organic molecules. Typical examples are O-alkylation forming an ether linkage, O-acylation forming an ester, O-alkylation forming acetals, N-alkylation forming amines, and N-acylation forming amides.
  • the derivitives of chitosan can be more hydrophilic or more lipophilic than the parent molecule.
  • the derivatives can be anionic, cationic, or neutral.
  • the term "chitosan containing material" refers to materials comprising chitosan, chitosan salts, chitosan derivatives, and mixtures thereof.
  • polysaccharide refers to a polymer comprising monosaccharides arranged in monomeric units (e.g., homoglycans, diheteroglycans, triheteroglucans, tetraheteroglycans, pentaheteroglucans) and includes both naturally occurring polysaccharides, derivatives of polysaccharides, and extracts from seaweed, seeds, tubers and roots.
  • polysaccharide applies to all classes of polysaccharides, including linear polysaccharides (e.g.
  • algins carrageenans
  • galactomannans e.g., guar gum and locust bean gum, and pectins
  • branched polysaccharides e.g., arabinans, arabinoglactans, xanthan, and xylans
  • branch-on- branch polysaccharides e.g., amylopectins, arabinoxylans
  • polysaccharides include, but are not limited to, xanthan, agar, alginic acid, carrageenans, pectins, corn starch, rice starch, wheat starch, guar gum, locust bean gum, psyllium seed gum, potato starch, tapioca starch, gum arabic, gum karaya, and cellulose.
  • aminopolysaccharide refers to positively charged polysaccharides including, but not limited to, chitosan and chitosan derivatives (e.g., N- alkylated chitosan derivatives), amino substituted cellulose, and amino-substituted starch.
  • carrageenan refers to the group of sulfated galactans (e.g., kappa-carrageenan and lambda-carrageenan) isolated from red seaweeds.
  • soluble polysaccharide refers to polysaccharides that are dissolvable in water or another liquid.
  • soluble polysaccharides include, but not limited to, xanthan, agar, alginic acid, carrageenans, pectins, corn starch, rice starch, wheat starch, guar gum, locust bean gum, psyllium seed gum, potato starch, tapioca starch, gum arabic, and gum karaya.
  • anionic polysaccharide or “negatively charged polysaccharide” refer to acidic polysaccharides or polysaccharides having a net negative charge (e.g., polysaccharides containing the following groups: uronic ester, sulfate half- ester, pyruval cyclic acetal, succinate half-ester) including, but not limited to, xanthan, xylans, pectins, carrageenans, algins, arabinoxylans, psyllium seed gum, gum arabic, and fucellarans.
  • uronic ester e.g., uronic ester, sulfate half- ester, pyruval cyclic acetal, succinate half-ester
  • neutral polysaccharide refers to polysaccharides having a neutral charge and includes, but is not limited to, amylopectins, amyloses, arabinans, guar gum and other galactomannans, and arabinogalactans.
  • dietary fiber refers to nondigestable polysaccharides, including, but not limited to, xanthan, agar, alginic acid, carrageenans, pectins, guar gum, locust bean gum, psyllium seed gum, gum arabic, gum karaya, and cellulose.
  • soluble dietary fiber refers to nondigestable polysaccharides that are dissolvable in water, including, bit not limited to, xanthan, agar, alginic acid, carrageenans, pectins, guar gum, locust bean gum, psyllium seed gum, gum arabic, and gum karaya.
  • partition coefficient As used herein, the term "partition coefficient" or "P" is used herein as a measure of lipophilicity.
  • the partition coefficient is defined by the following formula:
  • [compound] ⁇ - a) wherein a is the degree of dissociation of the compound in water calculated from ionization constants, [compound] oct is concentration in octanol, and [compound] ⁇ is concentration in water.
  • the partition coefficient may be derived experimentally by placing a compound in shaking device (e.g., a separatory funnel) with varying volumes of octanol and water, determining the concentration of the compound in each layer after mixing, and utilizing the equation to calculate P. In general, the more lipophilic the compound, the higher the partition coefficient.
  • log P is also used to refer to the lipophilicity of a compound and is the log of the partition coefficient. It is known that the rate of movement of a variety of organic compounds through cellular material is approximately proportional to the logarithm of partitional coefficients between an organic solvent and water.
  • the term "particle” refers to a small piece of matter.
  • the term “dispersable” refers to ability of compound to scatter or disaggregate in a liquid.
  • the term "food additive” refers to any material approved by the United States Department of Agriculture for inclusion in foodstuffs and substances that are generally recognized as safe (GRAS) and includes all substances, the intended use of which results or may reasonably be expected to result, directly or indirectly, either in their becoming a component of food or otherwise affecting the characteristics of food.
  • food flavoring refers to food additive or other substance derived from an animal, mineral, plant, or synthetic source capable of imparting a flavor to a substance or changing the flavor of a substance.
  • the term "food coloring” refers to any dye, pigment, or other substance made by a process of synthesis or similar artifice, or extracted, isolated, or otherwise derived, with or without intermediate or final change of identity, from a vegetable, animal, mineral, or other source and that, when added or applied to a food, drug, or cosmetic or to the human body or any part thereof, is capable (alone or through reaction with another substance) of imparting a color thereto or changing the color thereof.
  • vitamin refers to an organic molecule that is essential for the health of an animal, and includes, but is not limited to, vitamin A, thiamin (Bl), riboflavin (B2), Pyridoxine (B6), cyanocobalamin (B12), biotin, ascorbic acid (vitamin C), retinoic acid (vitamin D), vitamin E, folic acid and other folates, vitamin K, niacin, and pantothenic acid and their derivatives.
  • the term “mineral” refers to elements (e.g. , sodium, potassium, magnesium, calcium, phosphorus, and chlorine) and trace elements (e.g. , iron, zinc, manganese, fluorine, copper, molybdenum, chromium, selenium, and iodine) required for normal body function.
  • trace elements e.g. , iron, zinc, manganese, fluorine, copper, molybdenum, chromium, selenium, and iodine
  • phytonutrient refers to organic compounds isolated from plants that have a biological effect, and includes, but is not limited to, compounds of the following classes: isoflavonoids, oligomeric proanthcyanidins, indol-3-carbinol, sulforaphone, fibrous ligands, plant phytosterols, ferulic acid, anthocyanocides, triterpenes, omega 3/6 fatty acids, polyacetylene, quinones, terpenes, cathechins, gallates, and quercitin.
  • the present invention relates to compositions including an aminopolysaccharide and a negatively charged polysaccharide that are readily dispersable in aqueous solution and find use as dietary supplements and in foods.
  • the particles of the present invention have desirable organoleptic properties (e.g., good mouth feel) and are useful for binding both dietary and circulating lipids in the body.
  • organoleptic properties e.g., good mouth feel
  • additional substances may be incorporated into or used in conjunction with the particles, including, but not limited to vitamins, minerals, antioxidants, phytonutrients, food colorings, flavorings, preservatives, powdered food products, freeze dried food products, and whole food products.
  • the present invention provides particles comprising an aminopolysaccharide (e.g., chitosan, one of its derivatives, or amino-substituted cellulose, or mixtures thereof) and a negatively charged polysaccharide.
  • the chitosan is a co-polymer of ⁇ -1— »4-linked 2-acetamido-2-deoxy-D-glucopyranose and ⁇ - 1— >4-linked 2-amido-2-deoxy-D-glucopyranose formed by the alkaline deacetylation of chitin with concentrated sodium hydroxide at elevated temperatures (See, e.g., Varum et al., Carbohydrate Res.
  • the degree of deacetylation may vary.
  • the chitosan is deacetylated to between about forty percent and ninety percent.
  • the particles comprise one or more derivatives of chitosan.
  • the derivative is a chitosan salt (e.g., chitosan hydrochloride, chitosan hydrobromide, chitosan malate, chitosan phosphate, chitosan formate, chitosan acetate, chitosan propionate, chitosan chloroacetate, chitosan hydroxyacetate, chitosan butyrate, chitosan isobutyrate, chitosan acrylate, and mixtures thereof).
  • chitosan salt e.g., chitosan hydrochloride, chitosan hydrobromide, chitosan malate, chitosan phosphate, chitosan formate, chitosan acetate, chitosan propionate, chitosan chloroacetate, chitosan hydroxyacetate, chitosan butyrate, chitosan isobutyrate, chito
  • the derivative is a covalently modified chitosan derivative (e.g., carboxymethylchitosan, N-salicylidenechitosan, succinylchitosan, N-carboxyacylchitosan, etc.).
  • chitosan derivative e.g., carboxymethylchitosan, N-salicylidenechitosan, succinylchitosan, N-carboxyacylchitosan, etc.
  • the particles of the present invention also comprise one or more of a variety of polysaccharides.
  • the polysaccharide is an anionic or negatively charged polysaccharide (e.g., xanthan, xylans, pectins, carrageenans, algins, arabinoxylans, psyllium seed gum, gum arabic, and fucellarans, or mixtures thereof).
  • the polysaccharide is a neutral polysaccharide (e.g., amylopectins, amyloses, arabinans, guar gum and other galactomannans, and arabinogalactans, or mixtures thereof).
  • the chitosan and polysaccharide particles of the present invention have a variety of formulations.
  • the formulation provides a particle that is dispersable in aqueous solutions.
  • the resulting dispersion is pleasant to drink, with an acceptable mouthfeel and taste.
  • the concentration of chitosan is about 50% to 99%, while the concentration of polysaccharide is about 1% to 50%.
  • the concentration of chitosan is from about 60% to 80%, while the concentration of polysaccharide is from about 20% to 40%.
  • the particles binds compounds having a log P of greater than 1.5.
  • the particles comprise one or more additional compounds as described below.
  • a plurality of particles are provided as a powder, or alternatively, in capsules, tablets, or liposomes.
  • the aminopolysaccharide and negatively charged polysaccharide particles of the present invention may be incorporated into the aminopolysaccharide and negatively charged polysaccharide particles of the present invention. These compounds and substances may add to the palatability or sensory perception of the particles (e.g. , flavorings and colorings) or improve the nutritional value of the particles (e.g., minerals, vitamins, phytonutrients, antioxidants, etc.).
  • the included compounds have a log P of greater than 1.5.
  • the particles comprise physiological acceptable salts (e.g. , NaCl 2 , CaCl 2 , MgSO 4 ) and non-ionic physiologically acceptable low molecular weight compounds (e.g., glucose).
  • the particles comprise at least one food flavoring such as acetaldehyde (ethanal), acetoin (acetyl methylcarbinol), anethole (parapropenyl anisole), benzaldehyde (benzoic aldehyde), N-butyric acid (butanoic acid), d- or 1-carvone (carvol), cinnamaldehyde (cinnamic aldehyde), citral (2,6-dimethyloctadien-2,6-al-8, gera-nial, neral), decanal (N-decylaldehyde, capraldehyde, capric aldehyde, caprinaldehyde, aldehyde C-10), ethyl acetate, ethyl butyrate, 3-methyl-3-phenyl glycidic acid ethyl ester (ethyl-methyl-phenyl-glycidate, strawberry
  • the particles comprise at least one synthetic or natural food coloring (e.g., annatto extract, astaxanthin, beet powder, ultramarine blue, canthaxanthin, caramel, carotenal, beta carotene, carmine, toasted cottonseed flour, ferrous gluconate, ferrous lactate, grape color extract, grape skin extract, iron oxide, fruit juice, vegetable juice, dried algae meal, tagetes meal, carrot oil, corn endosperm oil, paprika, paprika oleoresin, riboflavin, saffron, tumeric, tumeric and oleoresin).
  • synthetic or natural food coloring e.g., annatto extract, astaxanthin, beet powder, ultramarine blue, canthaxanthin, caramel, carotenal, beta carotene, carmine, toasted cottonseed flour, ferrous gluconate, ferrous lactate, grape color extract, grape skin extract, iron oxide, fruit juice, vegetable juice, dried algae
  • the particles comprise at least one phytonutrient (e.g., soy isoflavonoids, oligomeric proanthcyanidins, indol-3-carbinol, sulforaphone, fibrous ligands, plant phytosterols, ferulic acid, anthocyanocides, triterpenes, omega 3/6 fatty acids, polyacetylene, quinones, terpenes, cathechins, gallates, and quercitin).
  • phytonutrient e.g., soy isoflavonoids, oligomeric proanthcyanidins, indol-3-carbinol, sulforaphone, fibrous ligands, plant phytosterols, ferulic acid, anthocyanocides, triterpenes, omega 3/6 fatty acids, polyacetylene, quinones, terpenes, cathechins, gallates, and quercitin).
  • Sources of plant phytonutrients include, but are not limited to, soy lecithin, soy isoflavones, brown rice germ, royal jelly, bee propolis, acerola berry juice powder, Japanese green tea, grape seed extract, grape skin extract, carrot juice, bilberry, flaxseed meal, bee pollen, ginkgo biloba, red clover, burdock root, dandelion, parsley, rose hips, milk thistle, ginger, Siberian ginseng, rosemary, curcumin, garlic, lycopene, grapefruit seed extract, spinach, and broccoli.
  • the particles comprise at least one vitamin (e.g., vitamin A, thiamin (Bl), riboflavin (B2), pyridoxine (B6), cyanocobalamin (B12), biotin, ascorbic acid (vitamin C), retinoic acid (vitamin D), vitamin E, folic acid and other folates, vitamin K, niacin, and pantothenic acid).
  • the particles comprise at least one mineral (e.g., sodium, potassium, magnesium, calcium, phosphorus, chlorine, iron, zinc, manganese, fiourine, copper, molybdenum, chromium, selenium, and iodine).
  • a dosage of a plurality of particles includes vitamins or minerals in the range of the recommended daily allowance (RDA) as specified by the United States Department of Agriculture.
  • the particles comprise an amino acid supplement formula in which at least one amino acid is included (e.g., 1-carnitine or tryptophan).
  • aminopolysaccharide and negatively charged polysaccharide compositions are made by combining varying amounts of an aminopolysaccharide and a negatively charged polysaccharide. It is contemplated that those skilled in the art understand that various specific formulations of aminopolysaccharide and negatively charged polysaccharide particles described below can be altered or modified without changing the properties (e.g., partition coefficient, dispersability, fat binding capacity, mouthfeel when dispersed in aqueous solution) of the particles.
  • an aminopolysaccharide e.g. , chitosan or a derivative of chitosan
  • water or an aqueous solution
  • a negatively charged polysaccharide e.g., xanthan
  • an amount of aminopolysaccharide is chosen so that the final composition (i.e., particle) will comprise about 0.1% to 99.9% aminopolysaccharide on a weight/weight (w/w) basis, preferably about 50% to 90% aminopolysaccharide (w/w), and most preferably about 60% to 80% (w/w) aminopolysaccharide, and be able to bind compounds having a log P of greater than about 1.5.
  • the amount of the negatively charged polysaccharide is varied in relation to the aminopolysaccharide such that final composition (i.e., particle) comprises about 0.1% to 99.9% negatively charged polysaccharide on weight/weight (w/w) basis, preferably about 10% to 50% negatively charged polysaccharide (w/w), and most preferably about 20% to 40% (w/w) negatively charged polysaccharide.
  • the amount of water added to the slurry may also vary. Generally, enough water is added to wet the aminopolysaccharide. In some embodiments, about 10% to 50% water is added on weight/volume (w/v) basis. In some particularly preferred embodiments, about 30% to 40% (w/v) water is added. In still other embodiments, the dry aminopolysaccharide and negatively charged polysaccharide are mixed, and then water is added. In still further embodiments where an aqueous solution is utilized, the solution can contain food flavorings, colorings, phytonutrients, vitamins, and minerals as described above.
  • one or more negatively charged polysaccharides are added to the aminopolysaccharide slurry and the mixture is blended vigorously until particles form.
  • water is sprayed or added to a dry mixture of chitosan and polysaccharide while blending.
  • the amount of polysaccharide added may vary, but it should be sufficient to cause particle formation.
  • Any suitable blending apparatus may be used to blend or mix the aminopolysaccharide and the negatively charged polysaccharide.
  • the mixture is blended in a high speed Waring blender.
  • the mixture is mixed in an Ide-Con (Porsgrunn, Norway) mixing apparatus.
  • the mixture is blended in the blending apparatus until particles of the desired size, shape, and properties form.
  • blending is continued until the particles are dried.
  • the aminopolysaccharide and water are blended for about an 0.5 to 1.0 hours, the negatively charged polysaccharide is added, and the blending continued until the mixture dries.
  • the mixture is blended until particles of about 1 micron to 5 millimeters are formed.
  • the particles are dried while mixing at about 50°C to 80°C, preferably about 60°C. Additional compounds (e.g., food flavorings, colorings, phytonutrients, vitamins, and minerals as described above) may be added to the particles before or, preferably, after drying.
  • chitosan is coated with gelatin or xanthan, while in other embodiments, chitosan is coated with glycerol.
  • an amount of the coating agent sufficient to coat the chitosan is added to the chitosan, and the mixture blended vigorously as described above until the desired particles form.
  • a glycerol solution is sprayed onto chitosan particles. In some preferred embodiments, the solution is about 20% to 50% glycerol on a volume/volume (v/v) basis.
  • an amount of glycerol is chosen so that the final composition (i.e., particle) will comprise about 10% to 50% (w/w) glycerol, preferably about 15% to 30% (w/w) glycerol.
  • a gelatin solution is added to a chitosan and the mixture mixed vigorously until particles form.
  • an amount of gelatin is chosen so that the final composition (i.e., particle) will comprise about 5% to 50% (w/w) gelatin, preferably about 15% to 30% (w/w) gelatin.
  • the present invention be limited to particular mechanism of action. Indeed, an understanding of the mechanism is not necessary to make and use the present invention.
  • the process produces a particle comprising a chitosan core with a polysaccharide coating.
  • a negatively charged polysaccharide is utilized, the polysaccharide is attracted to the positively charged chitosan.
  • the particles are added to water or an aqueous solution, the particles disperse readily due to hydration of the polysaccharide coating. Indeed, it is contemplated that in some cases the resulting composition is colloidal in nature. It is also contemplated that hydration of the polysaccharide coating eliminates or reduces the gritty mouthfeel of uncoated chitosan.
  • the present invention provides chitosan and polysaccharide particles comprising a polysaccharide core coated with chitosan and/or a chitosan derivative.
  • a polysaccharide is coated with chitosan by vigorously blending the polysaccharide with a chitosan solution.
  • the chitosan solution comprises an aqueous solution of chitosan and/or a chitosan derivative. It is well known in the art that chitosan is insoluble in neutral and basic aqueous solutions. Accordingly, it is contemplated that the pH of the chitosan solution be acidic. In some embodiments, the solution is acidified with lactic acid.
  • the chitosan solution comprises about 1% to 20% (w/v) chitosan, preferably about 2% chitosan. In other embodiments, the chitosan solution comprises about 1% to 10% (w/v) lactic acid, preferably about 4% (w/v) lactic acid. It is further contemplated that a sufficient amount of the chitosan solution is combined with the polysaccharide so that particles are formed during vigorous mixing. In some embodiments, about 0.1 to 5 ml of chitosan solution is added per gram of polysaccharide. In some particularly preferred embodiments, about 0.5 to 1.0 ml of chitosan solution is added per gram of polysaccharide. In still further embodiments, additional compounds (e.g., food flavorings, colorings, phytonutrients, vitamins, and minerals as described above) are incorporated into the solution or added before or after mixing. In other embodiments, the particles are dried after formation.
  • additional compounds e.g., food flavorings
  • the present invention contemplates the dietary use of the aminopolysaccharide and negatively charged polysaccharide particles. Because the particles are readily dispersable in aqueous solution and have an improved mouthfeel as compared to chitosan alone, dosages of from 0.1 to 100 grams, preferably about 1 to 20 grams, and most preferably about 3 to 12 grams, can be consumed. The present invention is not limited to any particular timing of consumption. A dose of the particles may be consumed weekly, daily, or several times throughout the day (e.g., before or after one or several daily meals).
  • the particles of the present invention have certain biological effects following ingestion.
  • the chitosan and polysaccharide particles bind fatty acids and other dietary and circulating lipids (e.g., triglycerides, bile acids, cholesterol, and other sterols).
  • ingestion of the particles of the present invention leads to increase in the amount of lipid excreted in the faeces.
  • particles of the present invention find use as a pharmaceutical for the treatment gall bladder disease, in which the absorption and utilization of lipids is not desirable; in the treatment of obesity; and in gastro-intestinal disorders or coronary disease where bile acids, cholesterol, and other sterol lowering is desired.
  • a biologically or therapeutically effective amount of the particles of the present invention is that amount that upon use for a period of about three months, causes a decrease in circulating lipids.
  • a biologically or therapeutically effective amount is that amount that causes an increase in the lipid content of the stool.
  • the particles find use in enhancing the excretion of exogenous materials, toxins, and drugs from the body. For example, it is contemplated that oral intake of the particles will enhance excretion of waste products in patients with reduced kidney function.
  • particles of the present invention find use for inclusion in dietary supplement powders and drinks, including those formulated for use in very low calorie diets. Examples of such drinks and supplements are described in U.S. Pat. Nos. 5,470,839; 5,760,082; 4,282,265; 5,904,924; 5,948,460; 4,814,172; 4,834,990; each of which is incorporated herein by reference. It is contemplated that these formulations may be altered by substituting the fiber component with the particles of the present invention, or simply adding particles to the formulations.
  • the particles of the present invention also find use as carriers of pharmaceutical compositions (e.g., anionic drugs).
  • the pharmaceutical composition is incorporated into the particle before or during blending.
  • the particles may be provided alone or in combination with any of the compounds described above in tablets, pills, dragees, capsules, solutions, liquids, slurries, liposomes, suspensions and emulsions.
  • the particles and compounds may be further provided in aqueous solution, oily solution, as a powder, or in any of the other forms discussed above.
  • the tablet or capsule of the present invention may be coated with an enteric coating which dissolves at a pH of about 6.0 to 7.0.
  • a suitable enteric coating which dissolves in the small intestine but not in the stomach is cellulose acetate phthalate. Further details on techniques for formulation for and administration and administration may be found in the latest edition of Remington 's Pharmaceutical Sciences (Maack Publishing Co., Easton, PA).
  • This Example describes the synthesis of polysaccharide coated chitosan particles.
  • Thirty grams of deodorized shrimp chitosan Natural Biopolymer, Inc./Vanson, Raymond, WA
  • a 12 ml water in which 0.07 grams vanilla (SFK Norge AS, Skytta, Norway) and 0.5 grams of aspartam have been dissolved.
  • 13.5 grams of xanthan gum (SFK Norge) is added to slurry while mixing in an Ide-Con mixer (Porsgrun, Norway) for approximately one hour to form particles.
  • the particles are then dried with hot air (60°C) while mixing.
  • 0.5 grams of blood orange powder (Ringe & Kuhlmann, Hamburg, Germany) is added.
  • the composition (wt%) after drying is:
  • Blood orange powder 1.0 It will be recognized the process described above may be altered by substituting guar gum, carrageenan, alginic acid, pectin and other polysaccharides for the xanthan gum. Likewise, chitosan salts and other derivatives of chitosan may replace the deodorized shrimp chitosan. Furthermore, other food additives such as sweeteners, flavorings, vitamins, minerals, phytonutrients may be added before, after, or during mixing and drying.
  • This Example describes the synthesis of polysaccharide coated chitosan particles. Thirty grams of deodorized shrimp chitosan is sprayed with a 12 ml water in which 0.07 grams vanilla and 0.5 grams of aspartame have been dissolved. Next, 13.5 grams of xanthan gum is added to slurry while mixing in an Ide-Con mixer (Porsgrun, Norway) for approximately one hour to form particles. The particles are then dried with hot air (60°C) while mixing. After the particles are dried, 1.0 grams of blood orange powder is added.
  • This Example describes the synthesis of polysaccharide coated chitosan particles. Thirty grams of deodorized shrimp chitosan, 10 grams of xanthan gum, and 0.4 grams of aspartam are mixed by shaking in an Erlenmeyer flask. The mixture is transferred to an Ide-Con mixer (Porsgrun, Norway), and 42 ml water is sprayed into the mixture and 0.2 grams blood orange powder is added while vigorously mixing for about one hour. The particles are then dried with hot air (50-60°C) while mixing.
  • This Example describes the preparation of polysaccharide coated chitosan particles. Thirty grams of deodorized shrimp chitosan, 10 grams of lactic acid powder, 9.5 grams xanthan gum, and 0.5 grams of aspartame, and 0.025 grams blood orange powder are mixed by shaking in an Erlenmeyer flask. The mixture is transferred to an Ide-Con mixer (Porsgrun, Norway), and 70 ml water is sprayed into the mixture vigorously mixing and drying with hot air (50-60°C) for about one hour. During mixing, another 0.23 grams of blood orange powder are added. The particles are then dried with hot air (50-60°C) while mixing.
  • Ide-Con mixer Pansgrun, Norway
  • guar gum carrageenan, alginic acid, pectin and other polysaccharides
  • chitosan salts and other derivatives of chitosan may replace the deodorized shrimp chitosan.
  • other food additives such as sweeteners, flavorings, vitamins, minerals, phytonutrients may be added before, after, or during mixing and drying.
  • This Example describes the coating of xanthan gum with chitosan. Thirty grams of xanthan gum in a mixing bowl is sprayed with 16 ml of a filtered water solution containing 2% by weight deodorized shrimp chitosan and 4% by weight lactic acid while mixing vigorously. The particles are then dried with hot air (50-60°C) while mixing.
  • This Example describes the coating of xanthan gum with chitosan. Thirty grams of xanthan gum in a mixing bowl is sprayed with 20 ml of a filtered water solution containing 2% by weight deodorized shrimp chitosan, 4% by weight lactic acid, and 0.3 grams aspartame, while mixing vigorously. The particles are then dried with hot air (50- 60°C) while mixing.
  • guar gum carrageenan, alginic acid, pectin and other polysaccharides
  • chitosan salts and other derivatives of chitosan may replace the deodorized shrimp chitosan.
  • other food additives such as sweeteners, flavorings, vitamins, minerals, phytonutrients may be added before, after, or during mixing and drying.
  • This Example describes the coating of chitosan particles with glycerol.
  • Glycerol (15.5 grams) and 15 ml water are mixed into a homogenous mixture and heated to 60°C.
  • the glycerol/water mixture is then sprayed onto 65 grams of deodorized shrimp chitosan under vigorous mixing conditions and while continuously drying with hot air (50-60°C).
  • This Example describes the coating of chitosan particles with gelatin. Forty grams of deodorized shrimp chitosan and 10 grams of lactic acid powder are mixed under vigorous conditions. A gelatin solution (7.5 grams gelatin dissolved into 100 ml water at 60°C) is then sprayed into the chitosan mixture while vigorously mixing and drying with hot air (50-60°C).
  • Examples 9-12 are in vitro experiments stimulating fat binding properties in vivo.
  • the particles are combined with fat under acidic pH (simulating gastric conditions) followed by treatment at neutral conditions (simulating intestinal conditions). It is assumed that compounds that are not extractable with chloroform are not available to or extractable by the body.
  • This example compares the fat binding capacities of the chitosan/xanthan gum particles prepared essentially as described above in Examples 1-4 and chitosan alone. Soybean oil (5.0 g) and chitosan/xanthan gum particles (5.0 g) are dissolved in a stirred aqueous solution (0.1 N HCL, 500 ml) at 37°C.
  • the pH of the solution is adjusted to about 7 to 8 by the careful addition of sodium hydroxide pellets.
  • the mixture is stirred for 2 hours at 37°C and subjected to high vacuum filtration to separate gelled solution from non-gelled solution.
  • the separated gel and solution are then extracted with chloroform (3 x 200 ml) and then dried with magnesium sulfate, filtered, evaporated, and weighed.
  • the data indicate that the chitosan/xanthan particles bind the oil more tightly than chitosan alone.
  • This example compares the fat binding capacities of chitosan/xanthan gum particles prepared essentially as described in Examples 1-4 and chitosan alone.
  • This experiment is performed as in Example 9, except that 50 g of soybean oil is mixed with 5.0 g fat binding agent in 1000 ml aqueous solution (0.1 N HCL), and the mixture is extracted three times in 300 ml chloroform. No filterable gel is formed.
  • the data is presented in Table 2.
  • the xanthan/chitosan particles appear to have a higher affinity for soybean oil as compared to chitosan alone.
  • This example compares the fat binding capacities of chitosan/xanthan gum particles prepared essentially as described in Examples 1-4 and chitosan alone. This experiment is performed as in Example 9, except that 5.0 g palmitic acid is mixed with 5.0 g fat binding agent. No filterable gel is formed by the chitosan/xanthan particles. The data is presented in Table 2. As in Example 9, the xanthan/chitosan particles appear to have a higher affinity for soybean oil as compared to chitosan alone.
  • This example compares the fat binding capacities of chitosan/xanthan gum particles prepared essentially as described in Examples 1-4 and chitosan alone.
  • This experiment is performed as in Example 9, except that 10 g of palmitic acid is mixed with 1.0 g fat binder in 1000 ml aqueous solution (0.1 N HCL), and the mixture is extracted three times in 300 ml chloroform. No filterable gel is formed.
  • the data is presented in Table 4.
  • the xanthan/chitosan particles appear to have a higher affinity for soybean oil as compared to chitosan alone.
  • compositions comprising particles of an aminopolysaccharide and a negatively charged polysaccharide, and optionally one or more food additives.
  • the particles are readily dispersable in liquids, do not settle rapidly, and have a pleasant mouthfeel.

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Abstract

La présente invention concerne une composition dispersable comprenant un aminopolysaccharide et un polysaccharide chargé négativement. Un aminopolysaccharide et un polysaccharide chargé négativement, tel qu'une gomme xanthane, une gomme de guar, un acide alginique, une carraghénine et une pectine, sont mélangés de manière à former des particules de chitosane revêtues de ce polysaccharide. Ladite composition peut éventuellement contenir des arômes alimentaires, des colorants alimentaires, des vitamines, des minéraux et/ou des phytonutriments.
PCT/IB2001/001044 2000-05-03 2001-05-03 Compositions contenant des aminopolysaccharides et des polysaccharides charges negativement WO2001082724A2 (fr)

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1481672A1 (fr) * 2002-03-05 2004-12-01 Kao Corporation Compositions servant a ameliorer les proprietes des matieres fecales
US8628801B2 (en) 2004-04-29 2014-01-14 Universidad De Navarra Pegylated nanoparticles
US8895067B2 (en) 2004-04-29 2014-11-25 Universidad De Navarra Immune response stimulating composition comprising nanoparticles based on a methyl vinyl ether-maleic acid copolymer
WO2018163053A1 (fr) * 2017-03-07 2018-09-13 Primex Ehf. Chitosane microencapsulé, ses procédés de fabrication et procédés d'utilisation

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4223023A (en) * 1978-10-12 1980-09-16 Ivan Furda Nonabsorbable lipid binder
US4983583A (en) * 1987-10-21 1991-01-08 Sanofi, Societe Anonyme Granulated compositions of polysaccharides, process for their preparation and use
US5453282A (en) * 1992-03-24 1995-09-26 Kirin Beer Kabushiki Kaisha Dietary lipid digestion-absorption inhibitory agents and ingesta
EP0775450A2 (fr) * 1995-11-24 1997-05-28 Ar Trade-Invest SA Compositions diététiques contenant du chitosan

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4223023A (en) * 1978-10-12 1980-09-16 Ivan Furda Nonabsorbable lipid binder
US4983583A (en) * 1987-10-21 1991-01-08 Sanofi, Societe Anonyme Granulated compositions of polysaccharides, process for their preparation and use
US5453282A (en) * 1992-03-24 1995-09-26 Kirin Beer Kabushiki Kaisha Dietary lipid digestion-absorption inhibitory agents and ingesta
US5654001A (en) * 1992-03-24 1997-08-05 Kirin Beer Kabushiki Kaisha Dietary lipid digestion-absorption inhibitory agents and ingesta
EP0775450A2 (fr) * 1995-11-24 1997-05-28 Ar Trade-Invest SA Compositions diététiques contenant du chitosan

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1481672A1 (fr) * 2002-03-05 2004-12-01 Kao Corporation Compositions servant a ameliorer les proprietes des matieres fecales
EP1481672A4 (fr) * 2002-03-05 2006-03-22 Kao Corp Compositions servant a ameliorer les proprietes des matieres fecales
US7691828B2 (en) 2002-03-05 2010-04-06 Kao Corporation Compositions for ameliorating fecal properties
US8628801B2 (en) 2004-04-29 2014-01-14 Universidad De Navarra Pegylated nanoparticles
US8895067B2 (en) 2004-04-29 2014-11-25 Universidad De Navarra Immune response stimulating composition comprising nanoparticles based on a methyl vinyl ether-maleic acid copolymer
WO2018163053A1 (fr) * 2017-03-07 2018-09-13 Primex Ehf. Chitosane microencapsulé, ses procédés de fabrication et procédés d'utilisation
US10945964B2 (en) 2017-03-07 2021-03-16 Primex Ehf. Microencapsulated chitosan, methods of making and methods for the use thereof

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