EP1539779A2 - Kondensierte palatinose in hydrierter form - Google Patents

Kondensierte palatinose in hydrierter form

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Publication number
EP1539779A2
EP1539779A2 EP03753376A EP03753376A EP1539779A2 EP 1539779 A2 EP1539779 A2 EP 1539779A2 EP 03753376 A EP03753376 A EP 03753376A EP 03753376 A EP03753376 A EP 03753376A EP 1539779 A2 EP1539779 A2 EP 1539779A2
Authority
EP
European Patent Office
Prior art keywords
palatinose
condensed palatinose
hydrogenated
hydrogenated condensed
glucopyranosyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP03753376A
Other languages
German (de)
English (en)
French (fr)
Inventor
Alireza Haji Begli
Michael Klingeberg
Markwart Kunz
Manfred Vogel
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Suedzucker AG
Original Assignee
Suedzucker AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Suedzucker AG filed Critical Suedzucker AG
Publication of EP1539779A2 publication Critical patent/EP1539779A2/de
Withdrawn legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/02—Acyclic radicals, not substituted by cyclic structures
    • C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
    • A—HUMAN NECESSITIES
    • A21—BAKING; EDIBLE DOUGHS
    • A21D—TREATMENT OF FLOUR OR DOUGH FOR BAKING, e.g. BY ADDITION OF MATERIALS; BAKING; BAKERY PRODUCTS
    • A21D2/00—Treatment of flour or dough by adding materials thereto before or during baking
    • A21D2/08—Treatment of flour or dough by adding materials thereto before or during baking by adding organic substances
    • A21D2/14—Organic oxygen compounds
    • A21D2/18—Carbohydrates
    • A21D2/181—Sugars or sugar alcohols
    • A—HUMAN NECESSITIES
    • A21—BAKING; EDIBLE DOUGHS
    • A21D—TREATMENT OF FLOUR OR DOUGH FOR BAKING, e.g. BY ADDITION OF MATERIALS; BAKING; BAKERY PRODUCTS
    • A21D2/00—Treatment of flour or dough by adding materials thereto before or during baking
    • A21D2/08—Treatment of flour or dough by adding materials thereto before or during baking by adding organic substances
    • A21D2/14—Organic oxygen compounds
    • A21D2/18—Carbohydrates
    • A21D2/188—Cellulose; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23C—DAIRY PRODUCTS, e.g. MILK, BUTTER OR CHEESE; MILK OR CHEESE SUBSTITUTES; MAKING OR TREATMENT THEREOF
    • A23C9/00—Milk preparations; Milk powder or milk powder preparations
    • A23C9/12—Fermented milk preparations; Treatment using microorganisms or enzymes
    • A23C9/13—Fermented milk preparations; Treatment using microorganisms or enzymes using additives
    • A23C9/1307—Milk products or derivatives; Fruit or vegetable juices; Sugars, sugar alcohols, sweeteners; Oligosaccharides; Organic acids or salts thereof or acidifying agents; Flavours, dyes or pigments; Inert or aerosol gases; Carbonation methods
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K10/00—Animal feeding-stuffs
    • A23K10/10—Animal feeding-stuffs obtained by microbiological or biochemical processes
    • A23K10/16—Addition of microorganisms or extracts thereof, e.g. single-cell proteins, to feeding-stuff compositions
    • A23K10/18—Addition of microorganisms or extracts thereof, e.g. single-cell proteins, to feeding-stuff compositions of live microorganisms
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K20/00—Accessory food factors for animal feeding-stuffs
    • A23K20/10—Organic substances
    • A23K20/163—Sugars; Polysaccharides
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K50/00—Feeding-stuffs specially adapted for particular animals
    • A23K50/40—Feeding-stuffs specially adapted for particular animals for carnivorous animals, e.g. cats or dogs
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K50/00—Feeding-stuffs specially adapted for particular animals
    • A23K50/40—Feeding-stuffs specially adapted for particular animals for carnivorous animals, e.g. cats or dogs
    • A23K50/42—Dry feed
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L19/00—Products from fruits or vegetables; Preparation or treatment thereof
    • A23L19/03—Products from fruits or vegetables; Preparation or treatment thereof consisting of whole pieces or fragments without mashing the original pieces
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L19/00—Products from fruits or vegetables; Preparation or treatment thereof
    • A23L19/09—Mashed or comminuted products, e.g. pulp, purée, sauce, or products made therefrom, e.g. snacks
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Preparation or treatment thereof
    • A23L2/385—Concentrates of non-alcoholic beverages
    • A23L2/39—Dry compositions
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Preparation or treatment thereof
    • A23L2/52—Adding ingredients
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Preparation or treatment thereof
    • A23L2/52—Adding ingredients
    • A23L2/60—Sweeteners
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L21/00—Marmalades, jams, jellies or the like; Products from apiculture; Preparation or treatment thereof
    • A23L21/10—Marmalades; Jams; Jellies; Other similar fruit or vegetable compositions; Simulated fruit products
    • A23L21/12—Marmalades; Jams; Jellies; Other similar fruit or vegetable compositions; Simulated fruit products derived from fruit or vegetable solids
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L21/00—Marmalades, jams, jellies or the like; Products from apiculture; Preparation or treatment thereof
    • A23L21/10—Marmalades; Jams; Jellies; Other similar fruit or vegetable compositions; Simulated fruit products
    • A23L21/15—Marmalades; Jams; Jellies; Other similar fruit or vegetable compositions; Simulated fruit products derived from fruit or vegetable juices
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/30—Artificial sweetening agents
    • A23L27/33—Artificial sweetening agents containing sugars or derivatives
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • 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 OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L7/00—Cereal-derived products; Malt products; Preparation or treatment thereof
    • A23L7/10—Cereal-derived products
    • A23L7/117—Flakes or other shapes of ready-to-eat type; Semi-finished or partly-finished products therefor
    • A23L7/126—Snacks or the like obtained by binding, shaping or compacting together cereal grains or cereal pieces, e.g. cereal bars
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L7/00—Cereal-derived products; Malt products; Preparation or treatment thereof
    • A23L7/10—Cereal-derived products
    • A23L7/117—Flakes or other shapes of ready-to-eat type; Semi-finished or partly-finished products therefor
    • A23L7/135—Individual or non-extruded flakes, granules or shapes having similar size, e.g. breakfast cereals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00—Drugs for genital or sexual disorders; Contraceptives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A61P37/04—Immunostimulants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P39/00—General protective or antinoxious agents
    • A61P39/06—Free radical scavengers or antioxidants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/12—Antihypertensives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H3/00—Compounds containing only hydrogen atoms and saccharide radicals having only carbon, hydrogen, and oxygen atoms
    • C07H3/06—Oligosaccharides, i.e. having three to five saccharide radicals attached to each other by glycosidic linkages

Definitions

  • the present invention relates to hydrogenated condensed palatinose, processes for producing the same, uses thereof, and foods and medicaments containing hydrogenated condensed palatinose.
  • Free radicals are unstable and highly reactive atoms, molecules' or radicals with unpaired electrons continuously by biochemical 0- xidation-reduction reactions in the presence of oxygen, by phagocytes, exposure to environmental toxins, ionizing radiation, ultraviolet rays or strong in the body physical Load are formed. Due to their extreme reactivity, free radicals pose a potential threat to healthy cells and their components. Cell components that are particularly affected are proteins, nucleic acids and polyunsaturated fatty acids in cell membranes.
  • the cells are mainly protected from the effects of free radicals by the antioxidants that act as radical scavengers. If antioxidants are not available in sufficient quantities, the cells have insufficient protection against free radicals. Reduced amounts of antioxidants can be observed, for example, in diseases such as cancer, diabetes, hypertension, male infertility, rheumatic diseases and chronic inflammatory diseases. Antioxidants also play play a major role in the detoxification and degradation of xenobiotics, which people come into contact with due to indoor pollution in the living area or at the workplace or due to improper nutrition.
  • Known primary endogenous antioxidants are, for example, superoxide dismutase (SOD), glutathione peroxidase (GPx), glutathione, catalase, ferritin and coeruloplasmin.
  • Glutathione is a cysteine-containing tripeptide and the most common thiol compound in mammalian cells.
  • GSH is a substrate for the enzymes glutathione-S-transferase and GSH-peroxidase, which catalyze reactions for detoxification of xenobiotic compounds and for oxidation inhibition of reactive oxygen molecules and free radicals.
  • glutathione-S-transferase As a substrate for glutathione-S-transferase, glutathione is converted into the corresponding disulfide GSSG by reversible oxidation. Glutathione is therefore a buffer system for the redox state of the cell.
  • Glutathione is also involved in cysteine transport, leukotriene and prostaglandin metabolism, deoxyribonucleotide synthesis, immune functions and cell proliferation (Bray and Taylor, Canadian J. Physiol Pharmacol., 71: 746-751 (1995).
  • the importance of glutathione, in particular for the intestinal tract, is evident from the massive damage to the intestinal mucosa that can be observed in GSH deficiency, for example after treatment with the GSH synthesis inhibitor buthioninsulfoximine (Martensson et al., Proc. Natl. Acad. Sci. USA, 87 (1990), 1715-1719).
  • the tissue concentration of GSH is regulated by various factors, including the nutritional status and the food itself belongs. There is therefore a close connection between tissue GSH concentration, nutrition and oxidative stress.
  • the glutathione-S-transferases form one of the most important detoxification systems of the cells, especially during the phase II of cell division.
  • the detoxification is carried out by transferring glutathione to electrophilic components that arise, for example, during the metabolism of carcinogens.
  • the GST-catalyzed nucleophilic attack of glutathione on electrophilic substrates greatly reduces their reactivity with regard to cellular macromolecules.
  • GSTs can greatly reduce the effectiveness of a number of chemical carcinogens. GSTs therefore play an important physiological role in protecting against oxidative stress and associated diseases, especially cancer.
  • the soluble GSTs are dimeric proteins. Each subunit has an active center, which consists of two functional areas, namely a hydrophilic G-domain, which binds the substrate glutathione, and an adjacent hydrophobic H-doe, to which various electrophilic substrates bind (Armstrong, Chem. Res. Toxicol., 10 (1997), 2-18).
  • the GSTs catalyze various types of reactions, for example the opening of epoxy rings, nucleophilic aromatic substitution reactions, reversible Michael additions to ⁇ , ⁇ -unsaturated aldehydes and ketones, isomerizations and sometimes peroxidase reactions.
  • Numerous chemical substance classes are known as GST substrates, for example antibiotics, pesticides, insecticides, carcinogens and medicines.
  • GST induction mainly occurs through various transcription mechanisms.
  • the regulatory areas of GST-encoding genes contain elements to which the aforementioned substances bind and can induce gene transcription.
  • Known elements are, for example, the glucocorticoid, xenobiotic and antioxidant reaction elements (ARE) (Eaton and Bammler, Toxicological Sciences, 49 (1999), 156-164).
  • Food components for example phytochemical substances, can also induce GST activities, in particular GST forms of the ⁇ class being induced in the intestinal area.
  • GST induction in the intestinal tract through food ingredients is used as a mechanism to prevent colon cancer discussed (Peters and Roelofs, Cancer Res., 52
  • Glycans act either directly or indirectly, i.e. only after
  • Food constituents that are difficult or not digestible that is to say dietary fibers or fiber that are resistant to digestion by human enzymes, are of particular importance for GST induction.
  • These include some carbohydrates, such as pectin, guar gum and resistant starch, which are fermented into short-chain fatty acids (SCFAs), especially acetic acid, propionic acid and butyric acid, only in the intestinal tract by the bacterial flora of the colon (Bartram et al., Cancer Res., 53 ( 1993), 3283-3288).
  • SCFAs short-chain fatty acids
  • the proportion of dietary fiber or fiber in the diet depends on many factors, for example the type of food and its method of preparation. Most foods are low in fiber. Vegetables, certain types of fruit, nuts, seeds and above all unrefined grain products are rich in fiber. The importance of food preparation for its fiber content is demonstrated by the example of resistant starch. This is the part of the starch that is not digested in the small intestine and thus reaches the colon unchanged. Starch from freshly cooked potatoes is broken down very well in the gastrointestinal tract, with only around 3% of the starch ingested passing through the small intestine unchanged and reaching the large intestine. If, on the other hand, the potatoes are cooled after cooking, their share of resistant starch increases. two to four times.
  • wheat bran cures are hardly suitable for cancer prevention. Similar to cellulose, wheat bran is hardly fermented by colon bacteria. In addition, undesirable side effects, such as meteorism and: cramp-like pain, occur with foods enriched with wheat bran (http: // www. Pharmazeutician-zeitung.de). It was also found that the phytic acid found in wheat bran, which is a widespread storage material in cereals, legumes and oilseeds, significantly affects the metabolism of minerals and prevents the absorption of calcium, magnesium, iron and zinc. As little as 25 g of wheat bran significantly reduce calcium absorption (Knox et al., Am. J. Clin. Nutr., 53 (1991), 1480-1492). For older people and people with an increased risk of osteoporosis, a diet enriched with wheat bran is therefore not unproblematic.
  • the basically fermentable resistant starch also has a number of disadvantages. It has been found that commercially available resistant starch is sometimes not fermentable, which is obviously related to the manufacturing process. Resistant starch produced only using special extrusion processes is butyrogenic, which means that butyric acid is formed. However, resistant starch produced under polymer-protective extrusion conditions is often not stable (http: //www.igv- gmbh.de/e/tagung/geb-hardt .htm).
  • the present invention is based on the technical problem of providing agents which are suitable for the prevention of cancers, in particular colon cancer, and which do not have the disadvantages of the fiber known in the prior art, and methods for their preparation, the agents compared to the agents conventionally used can be manufactured more easily and cost-effectively and used as fiber.
  • the present invention solves this technical problem by providing a method for producing hydrogenated condensed palatinose and by providing the hydrogenated condensed palatinose thus produced.
  • the process according to the invention for the production of the hydrogenated condensed palatinose comprises the catalytic hydrogenation of a solution containing condensed palatinose and, if appropriate, the separation of the hydrogenated condensed palatinose with a degree of polymerization (DP) of 4 to 10 from the reaction mixture.
  • DP degree of polymerization
  • the hydrogenated condensed palatinose according to the invention produced in this way is a mixture in particular of hydrogenated palatinose dimers, palatinose trimers and palatinose tetramers with a degree of polymerization of 4 to 10.
  • the hydrogenated condensed palatinose provided according to the invention is not appreciably cleaved neither under the pH conditions of the stomach nor by the enzymes of the small intestine mucosa.
  • the hydrogenated condensed palatinose according to the invention is Surprisingly, fermented to short-chain fatty acids with a high proportion of butyric acid only by microorganisms of human faeces, with considerably more butyric acid being formed in comparison to other fermentable fibers such as resistant starch.
  • the hydrogenated condensed Pa- When ingested, latinose reaches the caecum and the large intestine almost unchanged and is only fermented there by the human intestinal flora. It is excellently suitable as fiber. Since the hydrogenated condensed palatinose according to the invention easily dissolves, it is particularly suitable as soluble dietary fiber, which is completely or almost completely accessible to fermentation in the large intestine due to its excellent solubility. Compared to frequently used fiber such as wheat or oat bran, the hydrogenated condensed palatinose according to the invention also has the advantage that it contains no substances which lead to undesirable side effects.
  • the hydrogenated condensed palatinose according to the invention is also suitable as a highly effective agent for the prevention and / or treatment of diseases which are associated with oxidative stress.
  • the fermentation products, in particular butyrate, obtained in the fermentation of condensed hydrogenated palatinose both increase the expression of glutathione-S-transferase and also increase cellular glu lead tathion concentration.
  • Glutathione and glutathione-S-transferase are involved in the detoxification of electrophilic foreign substances, whereby their reactivity with regard to cellular macromolecules is greatly reduced. Both substances therefore have important detoxification and protective functions in cells, especially against the development of tumors.
  • Butyrate is also known to have an anti-proliferative effect on colon cancer cells.
  • the hydrogenated condensed palatinose according to the invention in particular its fermentation products, thus has antioxidative and anticancerogenic effects which are significantly increased compared to the effects of other dietary fibers, in particular condensed palatinose and resistant starch, due to the considerably higher amount of butyric acid produced during the fermentation.
  • the hydrogenated condensed palatinose according to the invention As a result of the fermentation of the hydrogenated condensed palatinose according to the invention to give short-chain fatty acids, in particular butyrate, there is also a marked pH drop in the acidic range in the large intestine. On the one hand, this worsens the living conditions for pathogenic intestinal microorganisms such as clostridia and on the other hand improves the living conditions for a ⁇ idophile microorganisms, for example the bifidus flora and lactic acid bacteria.
  • the hydrogenated condensed palatinose according to the invention thus has a prebiotic effect which, owing to the considerably increased production of butyric acid, is considerably increased compared to the condensed palatinose and resistant starch.
  • the hydrogenated condensed palatinose according to the invention is also distinguished in that, in comparison to other known dietary fibers, it can prevent the development of infectious diseases considerably better by suppressing the growth of pathogenic germs in the large intestine on the one hand due to the fermentation products formed and on the other hand due to their considerably higher levels - Availability can prevent or reduce the attachment of pathogenic germs to human or animal epithelial cells.
  • the hydrogenated condensed palatinose according to the invention can better strengthen the immune defense and prevent or fight general infections and inflammatory diseases, in particular chronic intestinal inflammation.
  • the hydrogenated condensed palatinose according to the invention modulates the glycemic properties of foods, foods and beverages particularly effectively.
  • the hydrogenated condensed palatinose according to the invention can also be produced in a very simple and inexpensive manner from condensed palatinose, which in turn can be produced inexpensively from palatinose.
  • palatinose (6-O- ⁇ -D-glucopyranosylfructose) can in turn be obtained by simple enzymatic rearrangement using immobilized bacterial cells, for example the species Protaminobacter rubrum, Erwinia rhapontici and Serratia plymuthica, or a sucrose isomerase isolated therefrom can be produced on an industrial scale from sucrose.
  • the hydrogenated condensed palatinose according to the invention is produced according to the invention by catalytically hydrogenating a solution containing condensed palatinose in a first step.
  • condensed palatinose is understood in particular to be a mixture of palatinose and its condensation products.
  • the condensation of substances is a chemical reaction which may possibly take place under catalytic influence, in which at least two molecules exit one simple molecule to form a larger molecule.
  • the term “condensed palatinose” therefore includes in particular a mixture of uncondensed palatinose, palatinose dimers, palatinose trimers, palatinose tetramers, palatinose pentamers and trisaccharides.
  • the trisaccharides consist of the condensation product of a simple sugar made from hydrolyzed palatinose and a palatinose disaccharide.
  • condensed palatinose can be produced from an acidified aqueous solution of palatinose by heat treatment at temperatures between 100 ° C and 170 ° C.
  • the water content in the initial mixture of water, organic acid and palatinose lies here usually around 33%, based on the palatinose used.
  • DE 38 18 884 A1 uses this process to obtain condensed palatinose which has the following composition: about 54% uncondensed palatinose, about 29.8% palatinose dimers, about 11.5% palatinose trimers and about 5% Palatinose tetramers.
  • a citric acidic aqueous palatinose solution is condensed with a composition of about 52.4% uncondensed palatinose, about 26% palatinose di eres, about 12% palatinose trimers and about 5.7% palatinose tetramers (Mutsuo et al., J. Carbohydr. Che., 12 (1993), 49-61).
  • a method for producing condensed palatinose from palatinose is also known, wherein palatinose is reacted with anhydrous hydrofluoric acid (HF) to form a mixture which essentially consists of different palatinose diers. In this process, the reaction takes place in an anhydrous medium at preferably 0 to 20 ° C.
  • the condensed palatinose obtained contains about 94% palatinose dimers and about 2% uncondensed palatinose (FR 2 680 789 AI).
  • FR 2 680 789 AI uncondensed palatinose
  • the condensed palatinose to be hydrogenated by heat treatment of an aqueous palatinose solution with a pH of 3.2 to 5.8 is generated at a temperature of 100 ° C to 170 ° C and at atmospheric pressure or reduced pressure.
  • the aqueous solution of the palatinose to be condensed is prepared by dissolving palatinose in water, in particular at a temperature of 105 ° C.
  • acidic catalysts are added to the aqueous palatinose solution.
  • Han it punched at the acidic catalysts' to H + - loaded strongly acidic cation exchangers, organic acids, boric acid, a combination of phosphoric acid with potassium dihydrogen phosphate or ammonium sulfate.
  • organic acids are preferably selected from the group consisting of citric acid, malic acid, succinic acid and tartaric acid.
  • the condensed palatinose to be hydrogenated is obtained by heat treatment of an aqueous palatinose solution in the presence of 0.02% by weight of citric acid, based on palatinose, under vacuum at a temperature of 135.degree ,
  • the condensed palatinose so produced preferably comprises a mixture comprising about 48% uncondensed palatinose, about 28% palatinose dimers, about 12% palatinose triars, about 5% palatinose tetramers, about 5% palatinose pentamers and about 2 % Hydrolysis products.
  • the condensed palatinose to be hydrogenated is obtained by reaction with anhydrous hydrofluoric acid at a temperature of 0 ° C. to 20 ° C.
  • the reaction ge isch preferably comprises about 73% to 94% palatinose dimers.
  • the condensed palatinose to be hydrogenated is produced from a palatinose melt.
  • the palatinose melt is obtained by adding palatinose to a solution of a catalytically active acidic substance in water and heating the mixture at a temperature of 130 ° C. to 160 ° C.
  • the mixture of palatinose, acidic substance and water used to produce the melt is characterized in that the water content is clearly below 12% by weight.
  • the palatinose mixture comprises 4% by weight to 12% by weight of water and 0.05% by weight to 0.5% by weight of the acidic substance.
  • the acidic substance can be an H + -laden strongly acidic cation exchanger, an organic acid, boric acid, a combination of phosphoric acid with potassium dihydrogen phosphate or ammonium sulfate.
  • the organic acid is preferably a slightly volatile organic acid, particularly preferably citric acid.
  • the solution of the organic acid in water is heated to a temperature of 55 ° C. to 95 ° C., particularly preferably to about 75 ° C., before and / or during the addition of the palatinose.
  • the addition of palatinose to the solution of the organic acid in water is preferably carried out with stirring.
  • the used for the production of the Palatinose melt The mixture of palatinose, organic acid and water is then heated to a reaction temperature of 140 ° C. to 155 ° C., particularly preferably about 145 ° C., until the melt, with the mixture being stirred continuously.
  • the condensed palatinose is obtained from the melt after about 20 to 100 minutes, preferably after 30 to 60 minutes, the temperature of the melt during this period being ; 130 ° C to 160 ° C, preferably at 140 ° C to 155 ° C, particularly preferably at 145 ° C.
  • the melt thus obtained is quenched with water after the reaction has ended, a syrup containing the condensed palatinose being obtained.
  • the water used to quench the melt is preferably added in a melt / water weight ratio of 10: 1 to 1: 2, particularly preferably 5: 1 to 1: 1.
  • the condensed palatinose obtained from the palatinose melt preferably comprises about 15 wt.% To 45 wt.% Uncondensed palatinose, 35 wt.% To 60 wt.% Palatinose dimers, less than 10 wt.% Palatinose tri ere and less than 5 wt .-% palatinose tetramers and palatinose penta ere.
  • the condensed palatinose obtained by one of the processes described above is depleted in an additional process step with regard to its uncondensed palatinose content before the catalytic hydrogenation.
  • the condensate is preferably depleted. based on uncondensed palatinose by means of a chromatographic separation of the uncondensed palatinose from the condensed palatinose obtained.
  • a cation exchanger loaded in particular with calcium ions is used for the chromatographic separation process.
  • the condensed palatinose obtained above is transferred into an aqueous solution and then subjected to a catalytic hydrogenation, the catalytic hydrogenation of the condensed solution containing palatinose being carried out according to the invention at elevated temperature and pressure in the presence of hydrogen using a catalyst.
  • a “hydrogenation” is understood to mean a normally catalytic introduction of hydrogen into an organic compound, that is to say a reduction of this compound.
  • a characteristic feature of the reduction or hydrogenation process is that the compound to be reduced is electrons.
  • the "hydrogenation of condensed palatinose” is used in context understood with the present invention a reduction at the anomeric center of unsubstituted fructose.
  • a “catalytic hydrogenation” is understood to mean a hydrogenation in the presence of a catalyst, that is to say a substance which reduces the activation energy for the hydrogenation to proceed and thereby increases the reaction rate of the hydrogenation without appearing in the end product of the hydrogenation reaction.
  • the solution of the condensed palatinose to be hydrogenated is prepared by dissolving condensed palatinose in an aqueous medium, preferably in water, in a concentration of 20% by weight to 40% by weight, preferably 30% by weight.
  • the pH of the aqueous solution is adjusted to a pH of 6 to 8 using suitable agents.
  • the pH of the solution of the condensed palatinose to be hydrogenated is adjusted to 7.8 by adding sodium hydroxide solution.
  • the hydrogenation of the condensed solution containing palatinose is carried out at a temperature of 40 ° C. to 140 ° C., in particular 60 ° C. to 80 ° C., preferably 70 ° C.
  • the catalytic hydrogenation of the condensed solution containing palatinose takes place in the presence of hydrogen, it being provided in a preferred embodiment of the process according to the invention that the hydrogen used has a pressure of 150 to 230 bar, in particular 100 to 200 bar, preferably 150 bar.
  • the hydrogenation of the condensed solution containing palatinose is carried out using a catalyst.
  • a mixture of a pure Raney metal and a Raney metal alloy is used as the catalyst, the Raney metal preferably being nickel, copper, cobalt or iron. With the Raney metal alloy. ; it is preferably an alloy of nickel, copper, cobalt or iron with aluminum, tin or silicon.
  • the catalyst used for the hydrogenation comprises, as active component, one or more metals of subgroup VIII of the periodic table on a support. Platinum, ruthenium, palladium and / or rhodium is preferably used as the active component.
  • the catalyst carrier preferably comprises activated carbon, aluminum oxide, zirconium oxide and / or titanium dioxide.
  • the condensed solution containing palatinose is preferably stirred continuously during the hydrogenation. According to the invention, it is particularly provided that the hydrogenation takes place over a period of at least 2 hours to 5 hours, preferably at least four hours.
  • the hydrogenation of the condensed palatinose is carried out continuously, semi-continuously or batchwise.
  • the hydrogenation according to the invention can be carried out either in the fixed bed or in the suspension process.
  • a product mixture is obtained according to the invention which contains 25% by weight to 36% by weight of hydrogenated condensed palatinose with a DP of 4.9% to 15% by weight of hydrogenated condensed palatinose with a DP of 6, 3 wt .-% to 7 wt .-% hydrogenated condensed palatinose having a DP of 8, 3 wt .-% to 7 wt .-% hydrogenated condensed palatinose having a DP of '10, 3 wt .-% to 7 % By weight of non-hydrogenated 'condensed palatinose and 40% by weight to 55% by weight of hydrogenated uncondensed palatinose.
  • the hydrogenated, condensed palatinose products obtained after hydrogenation of the condensed palatinose are separated from the reaction mixture and isolated with a DP of 4 to 10.
  • any physical and / or chemical separation processes can be used for the separation and isolation of these reaction products, which allow the separation of reaction products with a desired degree of polymerization.
  • chromatography processes are understood to mean any physical processes in which a separation of substances takes place by distribution between a stationary and a mobile phase, adsorption isotherms, distribution isotherms, reversed-phase matrices as separation mechanisms, ion pair systems, ion exchange, ion exclusion and gel per eation can be based.
  • the hydrogenated condensed reaction products are separated using gel permeation processes, which are also referred to as exclusion chromatography, molecular sieve chromatography or gel filtration processes.
  • Gel permeation is understood to mean the process in which, due to the migration of molecules through a gel matrix with a pore structure, a distribution according to the molecular size takes place due to a sieve effect.
  • the hydrogenated condensed palatinose products are separated from the reaction mixture Substances such as polydextrans, polyacrylic amides, agarose etc. are used as the gel matrix.
  • separation columns with Fractogel HW40S are used to separate hydrogenated condensed reaction products with a DP of 4 to 10 from the reaction mixture, the flow rate preferably being 600 ml / hour.
  • the fractions of hydrogenated condensed palatinose obtained in this way can be freeze-dried after further concentration using conventional methods and processed further.
  • the hydrogenated condensed palatinose After separation from the reaction mixture, the hydrogenated condensed palatinose has 30% by weight to 55% by weight of hydrogenated condensed palatinose with a DP of 4.20% by weight to 30% by weight of hydrogenated condensed sated palatinose with a DP of 6.7% to 13% by weight hydrogenated condensed palatinose with a DP of 8 and 2% by weight to 6% by weight hydrogenated condensed palatinose with a DP of 10.
  • the hydrogenated condensed palatinose obtained according to the invention is a mixture of different hydrogenated condensed palatinose products and comprises at least hydrogenated condensed palatinose with a DP of 4, hydrogenated condensed palatinose with a DP of 6, hydrogenated condensed palatinose with a DP of 8 and hydrogenated condensed Palatinose with a DP of 10.
  • the hydrogenated condensed palatinose according to the invention comprises at least one compound of the formula (1)
  • the hydrogenated condensed palatinose according to the invention preferably has the following composition: 30% by weight to 55% by weight hydrogenated condensed palatinose with a DP of 4, 20% by weight to 30% by weight hydrogenated condensed palatinose with a DP of 6.7% by weight to 13% by weight of hydrogenated condensed palatinose with a DP of 8 and 2% by weight % to 6% by weight of hydrogenated condensed palatinose with a DP of 10.
  • the proportion of hydrogenated condensed palatinose with a DP of 4 is preferably 35% by weight to 50% by weight.
  • the proportion of hydrogenated condensed palatinose with a DP of 6 is 22% by weight to 28% by weight.
  • the proportion of hydrogenated condensed palatinose with a DP of 8 is preferably 8; % By weight to 12% by weight.
  • the proportion of hydrogenated condensed palatinose with a DP of 10 is preferably 3% by weight to 5% by weight.
  • the hydrogenated condensed palatinose according to the invention preferably additionally comprises 6 to 12% by weight of non-hydrogenated condensed palatinose with a DP of 4.
  • the hydrogenated condensed palatinose according to the invention can comprise additional constituents, for example compounds with a DP of 1, such as glucose, fructose, sorbitol or mannitol, compounds with a DP of 2, such as isomaltulose or isomalt, compounds with a DP of 3, as not further characterized Trisaccharides, and compounds with a DP of 4, such as dipalatinose dianhydrides.
  • a DP of 1 such as glucose, fructose, sorbitol or mannitol
  • compounds with a DP of 2 such as isomaltulose or isomalt
  • compounds with a DP of 3 as not further characterized Trisaccharides
  • compounds with a DP of 4 such as dipalatinose dianhydrides.
  • the hydrogenated condensed palatinose according to the invention is advantageously resistant or almost resistant to degradation in the mammalian stomach and / or by the enzymes of the mammalian digestive tract.
  • the hydrogenated condensed palatinose product according to the invention is not or only to a limited extent split by the enzyme complexes saccharase / isomaltase and glucoamylase / maltase present in the small intestine. These enzyme complexes normally ensure that the disaccharides maltose and sucrose, and in some cases also maltooligosaccharides, which enter the small intestine are split into monosaccharides and as such enter the bloodstream via the intestinal wall.
  • the hydrogenated condensed palatinose according to the invention is therefore neither hydrolyzed by the pH conditions of the stomach nor significantly degraded by the human or animal enzymes of the digestive tract.
  • the hydrogenated condensed palatinose according to the invention is fermented in vitro by microorganisms from human faeces, that is to say microorganisms from the intestinal flora.
  • Short-chain fatty acids in particular butyric acid
  • Fatty acids in particular the amount of butyrate formed
  • the amount of butyrate produced in the fermentation of the hydrogenated condensed palatinose according to the invention is, for example, significantly higher than the amount of butyrate obtained in the fermentation of resistant starch.
  • These metabolites formed by the intestinal bacteria are responsible for the induction of glutathione-S-transferase, an enzyme that can offer the cells protection against carcinogens and oxidants.
  • the induction of glutathione-S-transferase by the fermentation products of the hydrogenated condensed palatinose according to the invention has been demonstrated in further in vitro tests.
  • the supernatant formed in the fermentation of hydrogenated condensed palatinose by intestinal bacteria led to a significant increase in the glutathione-S-transferase activity in the human colon cell line HT 29.
  • the GST activity induced by the fermentation products of hydrogenated condensed palatinose is significantly higher than with controls without carbohydrate, controls with non-hydrogenated condensed palatinose and controls with resistant starch.
  • the intracellular glutathione content was also increased significantly by 60% compared to controls by hydrogenated condensed palatinose.
  • Both glutathione and glutathione-S-transferase are known to increase cell protection against carcinogens and oxidants.
  • the results of the investigations carried out show that the The hydrogenated condensed palatinose produced in the digestive tract behaves similarly to resistant starch or food fibers which are difficult to degrade, that is to say fermentation in the large intestine area by the intestinal flora located there with the formation of short-chain fatty acids.
  • the fermentation products, in particular the butyric acid formed, of hydrogenated, condensed palatinose like the fermentation products of comparable difficult-to-digest food fibers or resistant starch, lead to an intracellular increase in the glutathione content or the content of glutathione-S-transferase catalyzing glutathione reactions, the intracellular content of the two components was significantly increased compared to resistant starch.
  • a particularly preferred embodiment of the invention therefore relates to the use of the hydrogenated condensed palatinose according to the invention as an agent or active ingredient for the treatment and / or prophylaxis of diseases which are associated with oxidative stress, in particular for the treatment and / or prophylaxis of cancer, in particular of the large intestine.
  • the hydrogenated condensed palatinose product according to the application is outstandingly suitable as a means for the treatment and / or prophylaxis of the abovementioned diseases.
  • a “disease” or “disease” is understood to mean disorders of the life processes and / or deficiency states in an organism, which are associated with subjectively perceived and / or objectively ascertainable physical changes.
  • Oxidative stress is a condition in which there is an imbalance between the formation and the breakdown of free radicals in the body or specific organs or tissues, where “free radicals” are molecules or their fragments and atoms that are caused by a single unpaired elect - Characterized and therefore extremely responsive.
  • diseases such as cancers, in particular of the large intestine, diabetes I and II, hypertension, stroke, male infertility, rheumatic diseases, coronary artery diseases, acute heart attacks and chronic inflammatory diseases, especially in the intestinal area, understood.
  • Mal for treating diseases are substances which act directly as active substances in the body on cellular macromolecules and thereby induce a series of functional changes, that is, a biological see effect, or their degradation or fermentation products act as active substances in the body.
  • the present invention relates to the use of the hydrogenated condensed palatinose produced according to the invention as an agent or active ingredient for strengthening the immune defense against general infections.
  • the use of the hydrogenated condensed palatinose according to the invention is provided as an active ingredient for the treatment and / or prevention of constipation and as an active ingredient for restoring and maintaining a healthy microorganism flora in the digestive tract.
  • the use of the hydrogenated condensed palatinose according to the invention is provided as an active ingredient for improving the absorption of food components, in particular minerals such as calcium, in the animal or human digestive tract, thus preventing and / or reducing symptoms of food deficiency.
  • the present invention furthermore relates to the use of the condensed palatinose according to the invention as an active ingredient for the prophylaxis of infectious diseases, for the prophylaxis of intestinal diseases, for the prophylaxis of colon carcinogenesis, for the prophylaxis of inflammatory diseases and / or for the prophylaxis of osteoporosis.
  • the hydrogenated condensed palatinose is administered in a dose which is sufficient, for example to cure the state of a disease caused by oxidative stress or the state of an infectious disease, or in particular to prevent it from stopping the progression of such a disease and / or to alleviate the symptoms.
  • the hydrogenated condensed palatinose according to the invention is preferably administered orally, so that it can reach the colon via the gastrointestinal tract.
  • the dosage of the hydrogenated condensed palatinose depends, among other things, on the dosage form, the age, the sex and the body weight of the organism to be treated, in particular the person to be treated or an animal to be treated, and the severity of the disease.
  • the hydrogenated condensed palatinose according to the invention is administered in the form of a pharmaceutical composition in order, for example, to treat and / or prevent diseases which are associated with oxidative stress or infections.
  • a “pharmaceutical composition” or a “medicament” is understood to mean a mixture used for diagnostic, therapeutic and / or prophylactic purposes, that is to say a mixture which promotes or restores the health of a human or animal body and which comprises at least one natural or comprises synthetically produced active ingredient that produces the therapeutic effect.
  • the pharmaceutical composition can be both a solid and a liquid mixture.
  • a pharmaceutical composition comprising the active ingredient can contain one or more pharmaceutically acceptable excipients.
  • the pharmaceutical composition may include additives commonly used in the art, such as stabilizers, manufacturing agents, release agents, disintegrants, lubricants, colorants, odorants, flavors, emulsifiers or other substances commonly used to prepare pharmaceutical compositions.
  • the hydrogenated condensed pharmaceutical composition containing palatinose is in the form of an oral pharmaceutical composition to be administered, in particular in the form of a suspension, tablet, pill, capsule, granulate, powder or a similar suitable dosage form.
  • the hydrogenated condensed palatinose used according to the invention is insensitive to gastric acid
  • the hydrogenated condensed palatinose can be contained in pharmaceutical forms which have a coating resistant to gastric juice.
  • the active ingredients contained in the pharmaceutical composition can pass through the stomach unhindered and are preferably only released in the upper or middle sections of the intestine.
  • the composition of gastric juice resistant coatings and methods for making such gastric juice resistant coatings are known in the art.
  • pharmaceutical forms are used which have a delayed active substance release mechanism, in order thus to enable long-term therapy of diseases which are caused by oxidative stress.
  • the structure and composition of such drug forms with delayed drug release are also known in the art.
  • the pharmaceutical composition containing hydrogenated condensed palatinose as part of a combination therapy for the treatment, in particular for the prophylaxis, of for example by oxidative Stress-induced diseases is used.
  • at least one further active ingredient or at least one further medicament for the same indication is administered as the active ingredient.
  • the combined use of hydrogenated condensed Palatinose and the at least one additional N '- the active ingredient or drug can be targeted at the reinforcement of therapeutic or prophylactic effects, but can also be on different biological systems function in the organism and strengthen so the overall effect.
  • Hydrogenated condensed palatinose and the at least one additional drug can either be administered separately or in the form of fixed combinations.
  • the choice of the additional drug or active substance mainly depends on the specific illness to be treated and its severity. If the disease is, for example, a disease associated with oxidative stress, such as a manifested colon carcinoma, basic chemotherapy that may be prescribed by the doctor, for example using 5-fluorouracil, can be administered by simultaneous administration of hydrogenated condensed palatinose get supported. If the disease is manifested diabetes, for example the drug therapy of macroangiopathy in the diabetic can be supported using platelet aggregation inhibitors by simultaneous administration of the hydrogenated condensed palatinose according to the invention.
  • oxidative stress such as a manifested colon carcinoma
  • basic chemotherapy that may be prescribed by the doctor, for example using 5-fluorouracil
  • the disease is manifested diabetes, for example the drug therapy of macroangiopathy in the diabetic can be supported using platelet aggregation inhibitors by simultaneous administration of the hydrogenated condensed palatinose according to the invention.
  • the use of the hydrogenated condensed palatinose for the prevention and / or treatment of diseases caused, for example, by oxidative stress or of infections takes place in that the hydrogenated condensed palatinose is used as an additive in animal feed or in drinking water is administered.
  • the hyd ; Condensed condensed palatinose thus enters the digestive tract of an animal with the ingested food, where it is then fermented in the large intestine by the intestinal flora.
  • the supply of the hydrogenated condensed palatinose used according to the invention via food is particularly suitable for the prophylaxis of diseases or infectious diseases caused, for example, by oxidative stress. With regular feeding of hydrogenated condensed animal feed containing palatinose, long-term prophylaxis of such diseases is possible.
  • feed or “animal feed” is understood to mean any substance or mixture of substances which is intended to be fed to animals in an unchanged, prepared, processed or processed state.
  • Animal feed can be in both solid and liquid form.
  • the terms "feed” and “animal feed” therefore also include drinking water for animals.
  • the feed can be either single feed or compound feed.
  • the active compounds according to the invention can be used in animal feed both in dissolved form and in solid form can be added.
  • the active compounds according to the invention can be added, for example in powder form, to the mineral mixture used for animal nutrition.
  • the hydrogenated condensed palatinose used according to the invention can also be added to the drinking water for animals according to the invention.
  • the hydrogenated concentrated palatinose is preferably added to drinking water immediately before use by adding the hydrogenated condensed palatinose with drinking water, for example in the form of powders or granules, so that the substances used according to the invention can preferably dissolve quickly.
  • the use of the hydrogenated condensed palatinose for the prevention and / or treatment of diseases caused, for example, by oxidative stress or of infections takes place in that the hydrogenated condensed palatinose as an additive to foods, dietetic foods or drinking water intended for human consumption.
  • the hydrogenated condensed palatinose thus enters the digestive tract of humans with the ingested food, where a fermentation by the intestinal flora then takes place in the colon area.
  • the supply of the hydrogenated condensed palatinose used in accordance with the invention via food is particularly useful for the prophylaxis of diseases or inflammation caused, for example, suitable for infectious diseases. With regular consumption of hydrogenated condensed foods containing palatinose, long-term prophylaxis of such diseases is possible.
  • food is understood to mean substances which are intended to be consumed by humans in the unchanged, prepared or processed state.
  • food can contain other substances that can be of natural or synthetic origin and that can have entered the food intentionally or unintentionally.
  • Food can be in both solid and liquid form.
  • the term “food” therefore includes all types of beverages, including drinking water, that are intended for human consumption.
  • the hydrogenated condensed palatinose used according to the invention can be used in food in dissolved form as well as in the solid state.
  • dietetic foods are understood to mean foods which are intended to serve a specific nutritional purpose in such a way that they bring about the supply of certain nutrients or other nutritionally active substances in a specific quantity ratio or in a specific nature. Distinguish dietary foods significantly different from foods of a similar nature due to their composition or properties. Dietary foods can be used in cases where certain nutritional requirements due to diseases, malfunctions or allergic reactions to individual foods or their ingredients must be met. Dietary foods can also be in both solid and liquid form.
  • the use of the hydrogenated condensed palatinose according to the invention is provided as a pharmaceutical carrier in a pharmaceutical composition.
  • the present invention also relates to the use of the hydrogenated condensed palatinose produced according to the invention for the production of a pharmaceutical composition which is intended for the treatment and / or prophylaxis of diseases which are caused by oxidative stress.
  • the use of the hydrogenated condensed palatinose according to the invention is provided for the production of a pharmaceutical composition for strengthening the immune defense against general infections.
  • the use of the hydrogenated condensed palatinose according to the invention is provided as an additive in foods and beverages intended for human consumption.
  • the provided hydrogenated condensed palatinose is used as dietary fiber, in particular as soluble dietary fiber, in foods.
  • a "dietary fiber” is understood to mean a food component which is indigestible for human or animal enzymes, but which is at least partially fermented by colon bacteria and is therefore to a small extent energy-efficient for the human or animal body.
  • “Soluble dietary fibers” are soluble in solutions, especially aqueous solutions.
  • the hydrogenated condensed palatinose according to the invention is particularly suitable as soluble dietary fiber because, owing to its very good solubility in water in the large intestine, it is in dissolved form and can therefore be completely or almost completely fermented by the intestinal flora. Compared to other, frequently used dietary fibers such as wheat or oat bran, the hydrogenated condensed palatinose according to the invention also has the advantage, when used as dietary fiber, that it contains no substances which lead to undesirable side effects.
  • Another embodiment of the invention relates to the use of the hydrogenated condensed palatinose according to the invention as a prebiotic fiber.
  • the use of hydrogenated condensed palatinose in the large intestine leads to a significant pH drop in the acidic range. Due to the reduced pH in the large intestine, the living conditions for pathogenic intestinal microorganisms deteriorate and at the same time: the living conditions for adidophilic microorganisms improve.
  • the condensed palatinose according to the invention thus serves according to the invention in particular as a dietary fiber source.
  • the hydrogenated condensed palatinose according to the invention is used in combination with other soluble or insoluble, fermentable or non-fermentable fiber.
  • the hydrogenated condensed palatinose according to the invention is selected in combination with at least one further fiber from the group of fibers consisting of soluble fibers such as short-chain fructo-oligosaccharides, long-chain fructo-oligosaccharides, galacto-oligosaccharides, hydrolyzed guar Gum, such as "Sunfibre” or "Benefibre", lactulose, xylo-oligosaccharides, lactosucrose, mal-to-oligosaccharides, such as "Fibersol-2" from Matsutani, isomalto-oligosaccharides, gentio-oligosaccharides, glucosyl-sucrose sugar, such as "Coupling sucrose”"from Hayashibara, soybean
  • the invention also relates .
  • mixtures of the hydrogenated condensed palatinose according to the invention alone or in combination with at least one of the aforementioned fibers, with cultures of probiotic lactobacteria, bifidobacteria, so-called “synbiotics”, are provided.
  • probiotic lactobacteria, bifidobacteria so-called “synbiotics”.
  • the added probiotic bifi- dobacterial cultures are carried out as living cultures or as dry cultures or permanent cultures.
  • the hydrogenated condensed palatinose according to the invention serves according to the invention as a dietary fiber source, the treatment and / or prevention of constipation, the restoration and maintenance of a healthy microorganism flora in the digestive tract , the improvement of the availability and the absorption of food components, such as minerals, in the animal or human digestive tract in general to support and restore health, in particular convalescence, and, as stated above, prevent the development of colon tumors and inflammatory bowel diseases.
  • the Hydrogenated condensed palatinose according to the invention also modulates and supports the immune system of the animal and human body.
  • the invention relates to the use of the hydrogenated condensed palatinose according to the invention for modulating the glycemic properties of foods or confectionery, in particular for special nutrition, child nutrition or nutrition of persons with disorders of the glucose / insulin metabolism
  • Glycemic reaction is the change in the blood glucose level after the intake of an easily digestible carbohydrate.
  • the strongest glycemic reaction is caused by carbohydrates from which glucose can be released and absorbed quickly after oral ingestion by saliva, pancreatic or small intestine enzymes.
  • An increase in blood glucose causes an insulin release in the healthy organism, insulin stimulating the absorption of glucose by peripheral tissues, for example skeletal muscles, so that the blood value drops back to the basic value.
  • the hydrogenated condensed palatinose according to the invention can lower the glycemic index in foods, foodstuffs and luxury foods and can therefore be used for the prophylaxis and / or therapy of diabetes mellitus (type II) and other metabolic disorders, preferably as a component of dietary foods and luxury foods ,
  • the use of the hydrogenated condensed palatinose according to the invention is a sweetener. tel provided.
  • the hydrogenated condensed palatinose according to the invention has a sweetness of about 34% compared to sucrose (100%). Therefore, the hydrogenated condensed Palatinose of the invention may not only be used as a soluble fiber with the associated aforementioned positive qualities, but also as a sugar substitute and / or sweeteners, particularly domestic 'dietary products. Since the hydrogenated condensed palatinose according to the invention is not broken down by the human oral flora, it has advantageous acariogenic properties. Hydrogenated condensed sweeteners containing palatinose are therefore advantageously characterized by their acariogenicity. The invention therefore also relates to a sweetener containing the condensed palatinose according to the invention.
  • the use of the hydrogenated condensed palatinose according to the invention is provided for the production of foods, confectionery and animal feed.
  • the use of the hydrogenated condensed palatinose according to the invention is provided for the production of acidic foods with a pH of 2 to 5, in particular 2 to 4.
  • the prebiotic effect of the hydrogenated condensed palatinose according to the invention is supported by such acidic foods.
  • the hydrogenated condensed palatinose according to the invention is particularly preferably used for the production of fruit juices or fruit juice preparations.
  • the present invention also relates to foods, foods and luxury foods which contain the hydrogenated condensed palatinose according to the invention alone or in combination with at least one further fiber and / or with cultures of probiotic bifidobacteria.
  • the at least one further fiber is selected from the group consisting of soluble fibers such as short-chain fructo-oligosaccharides, long-chain fructo-oligosaccharides, galacto-oligosaccharides, hydrolyzed guar gum, such as "Sunfibre” or "Benibibre” , Lactulose, xylo-oligosaccharides, lactosucrose, malto-oligosaccharides, such as “Fibersol-2” from Matsutani, isomalto-oligosaccharides, gentio-oligosaccharides, glucosyl-sucrose, such as “coupling sugar” from Hayashibara-oligosaccharide, soybean charcoal Oli
  • the hydrogenated condensed Pal invention tinose under ⁇ the pH conditions of the stomach and is hardly cleaved by the enzymes of the small intestinal mucosa, it is in the novel foods, food and beverage products containing the hydrogenated condensed Palatinose of the invention, in advantageously around reduced-calorie foods or luxury foods.
  • the foods according to the invention are milk products or milk products, for example cheese, butter, yoghurt, kefir, quark, sour milk, buttermilk, cream, condensed milk, dry milk, whey , Milk sugar, milk protein, milk mix, milk semi-fat, whey mix and milk fat products.
  • the inventive foods to baked goods in particular bread, including cookies and fine baked goods including dry baked goods.
  • the inventive food for bread spreads, margarine products
  • the foods according to the invention are fruit products, in particular jams, jams, jellies, fruit preserves, fruit pulp, fruit pulp, fruit juices, fruit juice concentrates, fruit nectar and fruit powder.
  • the hydrogenated condensed palatinose according to the invention contains
  • foods can also be vegetable products, in particular canned vegetables, vegetable juices and vegetable pulp.
  • the present invention relates to hydrogenated condensed palatinose-containing sweeteners were.
  • the hydrogenated condensed palatinose according to the invention has a sweetening power of approximately 34% compared to sucrose (100%) and is therefore particularly advantageously used as a sugar substitute and / or sweetener in confectionery, in particular in dietetic products.
  • the confectionery according to the invention is advantageously characterized by its acariogenicity.
  • the confectionery products according to the invention are, in particular, chocolate products, hard caramels, soft caramels, fondant products, jelly products, licorice, foam sugar products, coconut flakes, dragees, compressed products, candied fruit, brittle, nougat products, ice cream confectionery , Marzipan, chewing gum, granola bars, as well as ice cream or alcoholic or non-alcoholic sweet drinks.
  • a further preferred embodiment of the invention relates to pharmaceutical compositions or medicaments which contain hydrogenated condensed palatinose as active ingredient.
  • the hydrogenated condensed drugs containing palatinose can be used in particular for the treatment and / or prophylaxis of diseases which are associated with oxidative stress.
  • the DP2 area largely corresponds to isomaltulose.
  • the DP areas were determined using Raftilos® L40 or Raftiline® St. as a control.
  • Example 1 500 ml of the 30% reaction solution obtained in Example 1, which contained 50% condensed palatinose, 2% monosaccharides and 40% isomaltulose, was added to a mixture by adding 1N NaOH with stirring . pH adjusted to 7.8.
  • the hydrogenation r was carried out using a nickel catalyst (200 g wet weight) in the presence of hydrogen (150 bar) at 70 ° C. with stirring.
  • the isomaltulose (see Example 1) contained in the condensed palatinose solution was completely hydrogenated to 1,6-GPS and 1,1-GPM.
  • the solution obtained after removal of the catalyst was purified by ion exchange on an H + -laden cation exchanger and an OH ⁇ anion exchanger.
  • the lyophilizate obtained was characterized and used in in vitro analyzes for digestibility and fermentability with human faeces.
  • the stability of a substance in gastric passage can be determined by determining the rate of hydrolysis at a pH of 2.0 using sucrose and 1-kestose as controls.
  • the reaction mixture became after 60, 120 and 180
  • the table shows that hydrogenated condensed palatinose was only partially split under the pH conditions in the stomach.
  • pancreatic secretion contains a large number of hydrolases, among others also carbohydrate-splitting enzymes such as ⁇ -1,4-glucans (starch, glycogen), preferably split into maltose and maltooligosaccharides.
  • hydrolases among others also carbohydrate-splitting enzymes such as ⁇ -1,4-glucans (starch, glycogen), preferably split into maltose and maltooligosaccharides.
  • the mucosal enzyme complexes saccharase / isomaltase and glucoamylase / maltase present in the small intestine ensure in vivo that the disaccharides maltose and sucrose and partly also maltooligosaccharides which have entered the small intestine are split into monosaccharides and as such via the intestinal wall into can enter the bloodstream.
  • the enzyme complexes saccharase / isomaltase (SI complex) and glucoamylase / maltase (GM complex) were isolated from small pig intestine according to the method of H. Heymann (dissertation, Hanover, 1991). The cleavage of the saccharide according to the invention by small intestine ⁇ -glucosidases was determined as follows:
  • Triethanolamine (TRA) buffer 0.1 M, pH 7.0
  • the resistant starch used is Novelose 240 (from National Starch), the proportion of resistant starch being increased to 83% of resistant starch by enzymatic treatment using ⁇ -amylase / amyloglucosida.se and recovery of the insoluble fraction.
  • Vitamin solution (according to DSM 141) 0.5 ml
  • the HT29 cells were preincubated for 48 hours. Then the fermentation supernatants (10% vol.) Or 10% vol. Medium (control) were added. The HAT 29 cells were then incubated with the fermentation supernatants for a further 72 hours.
  • the HAT 29 cells were treated as follows: The cells from the treated incubation batches (approx. 6 ⁇ 10 6 cells / 2.5 ml batch) were in an extraction buffer (20 mM Tris-HCl, 250 mM sucrose, 1 mM dithiothreitol, 1 mM PMSF, 1 mM EDTA, pH 7.4) suspended and treated with an Ultra-Turrax for 1 minute.
  • the total glutathione activity was determined according to Habig et al. (J. Biol. Chem. 249, 7130-7139, 1974) with 1-chloro-2, 4-dinitrobenzene (1 mM). In the presence of glutathione (1 mM) the reaction was carried out at 30 ° C and pH 6.5. The conjugate formed was detected spectrophotometrically at 340 nm and was used to calculate the activity. 1 ⁇ Mol conjugate per minute corresponds to one activity unit. Intracellular glutathione was determined using a colorimetric test (glutathione assay kit, Calbiochem-Novabiochem). -
  • the hydrogenated condensed palatinose is mixed with drinking water to an 18%, 19%, 20%, 21%, 22%, 23%, 24%, 25 each %, 26%, 27% and 28% solution diluted and then each passed through a 0.45 ⁇ m membrane filter.
  • an 8% aqueous sucrose solution is prepared.
  • the samples are given in the order listed above.
  • the examiners, 9 people, should first taste the comparison standard and then one of each of the samples and state whether the sugar standard or the sample is sweeter or whether they cannot tell the difference. Drinking water was used to neutralize between tastings.
  • the number of samples to be tested can be reduced for the second tasting.
  • the 27% to 20% aqueous hydrogenated condensed palatinose solutions, beginning with the highest concentration, are compared to the comparison standard Conditions described above, tasted by 8 examiners.
  • Xi transition point at which there is a change from "standard is sweeter” to “no difference in sweetening power” or from “no difference in sweetening power " bar “to” standard is sweeter ".
  • X u transition point at which there is a change from "no difference in sweetness can be determined” to "sample is sweeter” or from “sample is sweeter” to “no difference in sweetness is detectable”.
  • Soak or dissolve gelatin with water Boil sugar, glucose syrup and hydrogenated condensed palatinose to the specified temperature, let cool slightly; Add gelatin, fruit acid and glycerin; Pour the mixture, place in the heat chamber, powder and oil.
  • Soak agar in water dissolve, add sugar and other ingredients and boil to 105 ° C. Pour the mass into the appropriate molds.
  • Sucrose, glucose syrup, hydrogenated condensed palatinose and water are boiled to 135 ° C and then evacuated. After cooling to 120 ° C, the pre-dissolved DL-malic acid, aroma and color are stirred in. The melt is stamped or poured.
  • Example of use 4 drinks
  • Example of use 8 baked goods
  • yeast is used as a raising agent.
  • the hydrogenated condensed palatinose according to the invention can only be used to a limited extent as a substrate by baker's yeast. Therefore only a part of the sugar was exchanged for hydrogenated condensed palatinose.
  • Whisk egg yolk, water, sugar, hydrogenated condensed palatinose and salt with a whisk Put the very hard beaten egg white on the egg yolk mixture. Mix the flour, cornstarch and baking powder, sieve on the snow and gently fold.

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EP03753376A 2002-09-11 2003-09-02 Kondensierte palatinose in hydrierter form Withdrawn EP1539779A2 (de)

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DE10242062 2002-09-11
DE10242062A DE10242062B4 (de) 2002-09-11 2002-09-11 Hydrierte kondensierte Palatinose, Verfahren zu deren Herstellung und deren Verwendung
PCT/EP2003/009725 WO2004031202A2 (de) 2002-09-11 2003-09-02 Kondensierte palatinose in hydrierter form

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WO2005103025A1 (en) * 2004-04-21 2005-11-03 Novogen Research Pty Ltd Isoflavene synthetic method and catalyst
ES2452733T3 (es) * 2004-05-28 2014-04-02 Abbvie Deutschland Gmbh & Co Kg Forma de dosificación obtenible a partir de una mezcla pulverulenta que comprende un pigmento inorgánico
EP1693045A1 (de) 2005-02-17 2006-08-23 Abbott GmbH & Co. KG Herstellung von Dosierungsformen aus wirkstoffhaltigen Schmelzen
CN100448884C (zh) * 2005-11-11 2009-01-07 广东省微生物研究所 一种由帕拉金糖制造低聚帕拉金糖的方法
EP1832281A1 (en) 2006-03-10 2007-09-12 Abbott GmbH & Co. KG Process for producing a solid dispersion of an active ingredient
JP2008169129A (ja) * 2007-01-10 2008-07-24 Obihiro Univ Of Agriculture & Veterinary Medicine 水溶性ポテトペプチドを含む、肝機能改善剤
EP1982601A1 (en) * 2007-04-17 2008-10-22 Nestec S.A. Reduced sugar ice confection
WO2008133512A1 (en) * 2007-04-26 2008-11-06 Csm Nederland B.V. Yeast-leavened dough and dry mix for preparing such a dough
US20090297660A1 (en) * 2008-06-02 2009-12-03 Kraft Food Holdings, Inc. Cheese Products Containing Galacto-Oligosaccharides And Having Reduced Lactose Levels
ITMI20081074A1 (it) * 2008-06-13 2009-12-14 Giordano Magnoni Alimento masticabile a base di almeno un vegetale e relativo processo di produzione
JP5247638B2 (ja) * 2009-09-08 2013-07-24 株式会社山田養蜂場本社 ハチミツに由来する褐変化が抑制されたハチミツ含有組成物及びその調製方法
CN107048328B (zh) * 2009-12-23 2021-07-09 赢创运营有限公司 甜味剂及其制备方法
WO2012003302A1 (en) * 2010-06-30 2012-01-05 Rich Products Corporation Composition and method for preparing frozen gelatin dessert
JP6305434B2 (ja) * 2013-01-18 2018-04-04 ズートツッカー アクチェンゲゼルシャフト マンハイム／オクセンフルト 非齲蝕原性ゼリー菓子
JP6032615B2 (ja) * 2013-08-06 2016-11-30 正征 武井 健康維持と旨さ及び販売促進性に優れるジャム
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WO2004031202A2 (de) 2004-04-15
WO2004031202A3 (de) 2004-05-06
DE10242062A1 (de) 2004-03-25
DE10242062B4 (de) 2007-02-15
DE10262005A1 (de) 2004-03-25
CA2498659A1 (en) 2004-04-15
AU2003271575A1 (en) 2004-04-23
US20050222406A1 (en) 2005-10-06
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DE10262005B4 (de) 2005-11-10

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