WO2009113435A1 - Préparation de dérivé de glucide - Google Patents

Préparation de dérivé de glucide Download PDF

Info

Publication number
WO2009113435A1
WO2009113435A1 PCT/JP2009/054103 JP2009054103W WO2009113435A1 WO 2009113435 A1 WO2009113435 A1 WO 2009113435A1 JP 2009054103 W JP2009054103 W JP 2009054103W WO 2009113435 A1 WO2009113435 A1 WO 2009113435A1
Authority
WO
WIPO (PCT)
Prior art keywords
sugar derivative
agent
sugar
gel
food
Prior art date
Application number
PCT/JP2009/054103
Other languages
English (en)
Japanese (ja)
Inventor
達雄 金子
麻衣子 金子
Original Assignee
Kaneko Tatsuo
Kaneko Maiko
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 Kaneko Tatsuo, Kaneko Maiko filed Critical Kaneko Tatsuo
Publication of WO2009113435A1 publication Critical patent/WO2009113435A1/fr

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/02—Algae
    • 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
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/715—Polysaccharides, i.e. having more than five saccharide radicals attached to each other by glycosidic linkages; Derivatives thereof, e.g. ethers, esters
    • A61K31/737—Sulfated polysaccharides, e.g. chondroitin sulfate, dermatan sulfate
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
    • A61K8/99—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from microorganisms other than algae or fungi, e.g. protozoa or bacteria
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/16—Emollients or protectives, e.g. against radiation
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • 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
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
    • C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
    • C08B37/006—Heteroglycans, i.e. polysaccharides having more than one sugar residue in the main chain in either alternating or less regular sequence; Gellans; Succinoglycans; Arabinogalactans; Tragacanth or gum tragacanth or traganth from Astragalus; Gum Karaya from Sterculia urens; Gum Ghatti from Anogeissus latifolia; Derivatives thereof
    • C08B37/0063—Glycosaminoglycans or mucopolysaccharides, e.g. keratan sulfate; Derivatives thereof, e.g. fucoidan
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
    • C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
    • C08B37/006—Heteroglycans, i.e. polysaccharides having more than one sugar residue in the main chain in either alternating or less regular sequence; Gellans; Succinoglycans; Arabinogalactans; Tragacanth or gum tragacanth or traganth from Astragalus; Gum Karaya from Sterculia urens; Gum Ghatti from Anogeissus latifolia; Derivatives thereof
    • C08B37/0063—Glycosaminoglycans or mucopolysaccharides, e.g. keratan sulfate; Derivatives thereof, e.g. fucoidan
    • C08B37/0072—Hyaluronic acid, i.e. HA or hyaluronan; Derivatives thereof, e.g. crosslinked hyaluronic acid (hylan) or hyaluronates

Definitions

  • the present invention relates to a sugar derivative preparation containing a sugar derivative having a novel polysaccharide structure. More specifically, the present invention has an extremely high molecular weight and a specific sugar chain unit repeating structure, and includes lactated saccharides that are lactated in the structure and may bind peptides or lipids. , Similar
  • the present invention relates to a sugar derivative preparation containing a sugar derivative exhibiting various characteristics significantly different from known substances belonging to this category.
  • Sisenjinori Processed and dried products of Sisenjinori have no mold and no information that it will not rot (http://www.kisendou.co/shiryou.htm). It is sold as food. This indicates the antibacterial properties of the zizenginori.
  • spirulan a sulfated polysaccharide extracted from spirulina, a food-based cyanobacteria
  • sugar components that make up are neutral sugar, uronic acid, methylated sugar, sulfuric acid and the like.
  • the swallowtail is an organism that is unique to the Kyushu region of Japan, and is a very delicate organism with many difficult restrictions on the growth environment and culture conditions. Except for a few reports, there are currently no sufficient studies on swirls and their secreted agar-like substances. Disclosure of the invention
  • the object of the present invention is to extract and analyze useful components derived from zizenginori, ascertain their chemical structure and action, and to create new and useful functional materials and functional preparations.
  • the inventors of the present invention succeeded in extracting a sugar derivative having a novel polysaccharide structure during the research process, and have completed the present invention through various structural analyzes and functional studies, and effective utilization methods. (First invention)
  • the first invention of the present application contains, as an active ingredient, a sugar derivative G specified as a sugar derivative G 1 or a sugar derivative G 2 below, and has any of the following uses (1) to (10): It is a sugar derivative preparation.
  • Saccharide derivative G 1 Derived from the freshwater cyanobacterium Aphanothece sacrum and has an average molecular weight of 2, 000, 000 or more, a saccharide structure having a hexose structure and a pentose structure.
  • the structure has a repeating structure of glycan units linked in a linear or branched chain by ⁇ -daricoside bond or 3) -daricoside bond, and the glycan unit is a saccharide structure In the sugar chain unit, 2.7 or more hydroxyl groups per 100 hydroxyl groups are sulfated, or all of the elements are sulfated. Derivatives with a sulfur content of 1.5% by weight or more.
  • Sugar derivative G2 derived from the freshwater cyanobacteria Azenothece sacrum, having an average molecular weight of 2,00,00 or more, containing lactated sulfated sugar as a sugar structure, In addition, a sugar derivative containing at least all of the trisaccharide structure having the sequence shown in the following chemical formula 1 and the disaccharide structure having the sequences listed in the following 1) to 6).
  • Chemical Formula 1 indicates a trisaccharide structure of hexose, hexose, and N-acetylmethylmuramic acid, and R and R ′ indicate sugars. Any one OH in Chemical Formula 1 is one OSO 3 —Or one that is OCH 3 including. )
  • the definition of “derived from sisendinori” is a part of the specification for specifying a sugar derivative as a substance, and limits the acquisition source or manufacturing method of the sugar derivative. is not.
  • the second invention of the present application is a sugar derivative preparation, wherein the sugar derivative preparation according to the first invention is a composition according to any one of the following (11) to (14).
  • a third invention of the present application is a sugar derivative preparation, wherein the cosmetic composition according to (2) of the second invention is any of the following.
  • Facial cleanser i) Facial cleanser, make-up remover, sarcophagus, shampoo, rinse, conditioner, bath salt, toothpaste
  • Hair pack hair polish, hair dye, hair styling wax, hair styling cream, hair styling mousse, hair styling gel, hair styling spray, hair growth agent
  • Nail coating agent Nail coating agent, teak, eyeliner, fan dedication, maskara, lipstick, eye shadow, eyebrow i v) lotion, essence, beauty cream, beauty gel , Latex, Hand Cream, Non Dodgeel, Packing Agent
  • V i Skin lotion, essence, beauty cream, beauty gel, milky lotion, face wash, makeup remover, pack agent, lotion after shaving
  • V i i Anti-wrinkle, lotion, beauty liquid, beauty cream, beauty gel, milky lotion, face wash, makeup remover, pack agent, shave after shave
  • a fourth invention of the present application is a sugar derivative preparation, wherein the food composition according to (2) of the second invention is any of the following.
  • a food composition containing sugar derivative G 1 or sugar derivative G 2 as a water retention additive i) A food composition containing sugar derivative G 1 or sugar derivative G 2 as a water retention additive.
  • Sugar derivative G 1 or sugar derivative G 2 can be used as an anti-inflammatory agent, antioxidant, cancer prevention function agent, fat absorption inhibitor, lipid metabolism improving agent, anti-stress function agent, anti-allergy function agent.
  • Sugar derivative G 1 or sugar derivative G 2 is added to thickening stabilizer, food adhesive, food polish, food gel substrate, colloidal food stabilizer, food colorant, food A food composition containing a preservative, a pH stabilizer for food, or an additive for adjusting the throat.
  • a fifth invention of the present application is a sugar derivative preparation, wherein the pharmaceutical composition according to (2) of the second invention is any of the following.
  • a sixth invention of the present application is a sugar derivative preparation, wherein the material composition of (14) according to the second invention is any of the following.
  • Fiber base or film base for food packaging including oral and suppositories, artificial skin constituents, contact lens materials, joint impact absorbing materials, shock absorbing sheets, artificial Saliva, anti-adhesion agent, diagnostic imaging contrast agent, granule coating agent, condom-coated gel, humidity control sheet
  • V i Heavy metal adsorption gel, water-soluble powder for metal adsorption, metal adsorption filter, gel substrate for fragrance or deodorant, deodorant, deodorization filter, fiber material with deodorization function
  • V i i Thickeners, shoe creams, soap bubbles, detergents, softeners, foam foam enhancers, immobilization carriers for microorganisms or enzymes, anti-condensation agents, anti-fogging glass, ink
  • Adhesive adhesive for leather products, coating agent for resin materials, coating agent for paper products, coating agent for textile products, surface protection agent, spray for coating
  • the lactated sulfated sugar in the sugar derivative G 1 according to any one of the first invention to the sixth invention is selected from sulfated muramic acid and sulfated N-acetyl muramic acid.
  • One or more sugar derivative preparations is selected from sulfated muramic acid and sulfated N-acetyl muramic acid.
  • the eighth invention of the present application is that the sugar derivative G 1 according to any one of the first to seventh inventions has at least glucose, galactose and mannose represented by Chemical Formula 2 and represented by Chemical Formula 3 Galactosamine, xylose and arabinose represented by Chemical Formula 4, dalc carboxylic acid and galacturonic acid represented by Chemical Formula 5, fucose and rhamnose represented by Chemical Formula 6, and A sugar derivative preparation in which a functional group selected from a functional group group including at least a sulfate group, a lactic acid group, and a methyl group is bonded to an arbitrary bonding position in the sugar structure.
  • the ninth invention of the present application provides a sugar derivative preparation, wherein a part of the sugar structure constituting the sugar derivative G 1 according to any one of the first to eighth inventions is further bound to a peptide or a lipid. It is.
  • the tenth invention of the present application is a sugar derivative preparation, wherein the sugar derivative G according to any one of the first invention to the ninth invention has an average molecular weight of 20, 0, 0, 0 or more.
  • the 11th invention of the present application is characterized in that the molar ratio of the main sugar structure constituting the sugar derivative G according to any of the 1st invention to the 10th invention is arabinose 1.1: fucose 3.
  • 8 Galactamine 2.
  • 0 3 is a sugar derivative preparation.
  • the 12th invention of the present application is that the sugar derivative G according to any of the 1st invention to the 11th invention is one or more of the following (15) to (17) in the measurement by the tea bag method: It is a sugar derivative preparation that exhibits solvent absorption.
  • the ratio B ZA between the absorption rate A for pure water and the absorption rate B for physiological saline under the same conditions is about 0.57 or more.
  • the sugar derivative G according to any one of the first to the first aspects of the present invention exhibits a pseudoplastic property that the viscosity decreases as the shear rate increases in an aqueous solution system. It is a sugar derivative preparation.
  • a fourteenth invention of the present application is a sugar derivative preparation in which the sugar derivative G according to any of the first to thirteenth inventions exhibits liquid crystallinity in a high concentration aqueous solution system.
  • the sugar derivative G according to any one of the first to the fourteenth aspects of the present invention has a two-step increase in transmitted light intensity as the cutting speed increases in the polarized transmitted light intensity in an aqueous solution system. It is a sugar derivative preparation that exhibits (increased birefringence).
  • the sugar derivative G according to any one of the first to fifteenth aspects of the present invention exhibits at least one of the following characteristics in an aqueous solution system containing a metal ion: It is a derivative preparation.
  • the seventeenth invention of the present application is the sugar derivative preparation, wherein the sugar derivative G according to any one of the first invention to the sixteenth invention is contained in any of the following forms (a) to (e): It is.
  • a polyion complex which is a complex of sugar derivative G 1 or sugar derivative G 2 and a polycation compound.
  • a polysaccharide liquid crystal slime obtained by bringing a high-concentration aqueous solution of sugar derivative G 1 or sugar derivative G 2 into contact with a metal ion selected from the group including at least calcium ion Ca 2+ .
  • sugar derivative preparation according to the present invention contains a sugar derivative derived from sisendinori and having a novel polysaccharide structure and exhibiting various useful properties, it has extremely diverse and useful applications.
  • Fig. 1 shows a photograph of Sisenzinori.
  • Figure 2 shows a photograph of a fibrous sugar derivative.
  • Figure 3 shows the infrared absorption spectrum of the sugar derivative.
  • Figure 4 shows the NMR spectrum of the sample.
  • Figure 5 shows the ultraviolet and visible spectrum of the sample.
  • Figure 6 shows the ESI 1 MS spectrum of the acid degradation product of the sample.
  • Figure 7 shows the viscoelasticity test method and the test results.
  • Figure 8 shows the shear stress-induced birefringence of the sample.
  • Fig. 9 shows a polarized photograph of the liquid crystal state of polysaccharides.
  • FIG. 10 shows the gelation of the polysaccharide.
  • Figure 11 shows the formation of a liquid crystal gel with polysaccharides.
  • Figure 12 shows the formation of a liquid crystal slime with polysaccharides.
  • Figure 13 is an electron micrograph of a polysaccharide molecular chain.
  • Figure 14 shows the molecular weight data of the polysaccharide.
  • FIG. 15 shows evidence of polysaccharide lactation.
  • Figure 16 shows a gel of a polysaccharide chemical bridge.
  • Figure 17 shows the metal adsorption of chemically cross-linked polysaccharides.
  • Figure 18 shows evidence of polysaccharide acetylation.
  • Figure 19 shows a photograph of a polysaccharide modified with a dye.
  • Figure 20 shows the change in viscosity of an aqueous polysaccharide solution with the addition of an acidic substance.
  • Figure 21 shows data derived from the constituent sugar sequences of polysaccharides.
  • Figure 22 shows the constituent sugars of polysaccharides The data from which the sequence was derived is shown.
  • Figure 23 shows the basis for determining the constituent sugars of the polysaccharide.
  • FIG. 24 is a table showing the antiviral properties of polysaccharides.
  • Figure 25 is a table showing the antiviral properties of polysaccharides.
  • a sugar derivative G specified as a sugar derivative G 1 or a sugar derivative G 2, that is, a useful sugar derivative derived from sisendinori and having a novel polysaccharide structure is used as an active ingredient.
  • a sugar derivative preparation containing the same is provided. This sugar derivative preparation has at least (1) water absorption, water retention, moisturizing agent, (2) antibacterial agent, (3) antiviral agent, (4) anticancer agent, (5) food health promotion agent, ( 6) Food thickener / stabilizer, (7) Metal recovery agent, (8) Binder / Adhesive, (9) Soil modifier, and (10) Infectious agent. More specific uses of the sugar derivative preparation will be described later in Examples.
  • the sugar derivative G (hereinafter also referred to simply as “sugar derivative”) has a molecular weight of at least 2,00,0,000, more preferably 2 0, 0 0 0, It has a molecular weight of 0 0 or more. Thus, it is the first time that an ultra-high molecular weight natural sulfated polysaccharide having a molecular weight exceeding 8, 00, 0, 0 0 has been found.
  • the sugar derivative contained in the sugar derivative preparation of the present invention contains, as a sugar structure in its repeated structure, lactic acid such as sulfated muramic acid, sulfated N-acetyl muramic acid, etc. Sulfated sugar.
  • lactic acid sugars such as muramic acid N_acetyl muramic acid have been confirmed as constituent sugars in fungal cell wall peptides, but lactic acid sulfated sugar No saccharides have been reported. That is, since this sugar derivative contains both lactated sugar and sulfated sugar, the acidity around the sugar chain is kept high. be able to. Since lactic acid is released at room temperature in an acidic aqueous solution of the sugar derivative, it is expected that when the sugar derivative is orally administered, the lactic acid is released by gastric acid and exhibits an intestinal action.
  • Sugar derivatives include at least hexose and pentose represented by Chemical Formula 2 to Chemical Formula 6 described above, and at least a sulfate group at any bonding position in these sugar structures. Functional groups such as lactic acid group and methyl group are bonded. In addition, a part of the sugar structure constituting the sugar derivative is further bound to a peptide or lipid.
  • the sugar derivative includes a trisaccharide structure having the sequence represented by Chemical Formula 1 and all of the disaccharide structures having the specific sequence described above. As a result of acid decomposition of the sugar derivative and FT-MS, it was found that these trisaccharide structure and disaccharide structure were released.
  • the sugar derivative has a mole ratio of the main sugar structure constituting it: arabinose 1.1: fucose 3.7: ramose 15.4: xylose 1 7.0: Mannose 1 0.5: Galactose 1 2.3: Galacturonic acid 4.6: Glucuronic acid 4.7: Gnore course 2 8. 8: Galactosin 2. 0 3 is there.
  • the constituent sugars identified in this way account for 94% of the total sugar derivatives. The remaining 6% is thought to contain sugars such as muramic acid.
  • the sugar derivative is a very good solvent-absorbing solvent with a weight absorption ratio of 5700 times that of pure water and 3300 times that of physiological saline as measured by the tea bag method. Therefore, it is extremely useful as a water absorbing / retaining / humectant.
  • the “tea bag method” is a solvent absorptivity measurement method as follows.
  • a sugar derivative solution using pure water or physiological saline as a solvent is put into a bag made of kitchen tapper. Immerse this bag in a beaker containing a large amount of the same type of solvent and leave it for 2 hours, then lift the bag and suspend it until the droplets no longer drop from the bag (usually about 5 hours). Suspend the suspension. After that, the solution in the bag is collected, and the weight W s of the solution 1 O ml and the weight W of the sugar derivative contained in this solution (this W is the weight of the residue obtained by thoroughly drying the solution in vacuum. Therefore, W s, W is calculated to obtain the solvent absorption rate.
  • the sugar derivative has been confirmed to exhibit the above-mentioned pseudo-plastic properties, and is useful as a thickening additive such as mayonnaise as well as known xanthan gum.
  • sugar derivatives can be used as active ingredients such as antibacterial agents, antiviral / anticancer agents, food health enhancers, food thickeners / stabilizers, and the like.
  • These applications include, for example, medical aids such as masks and lab coats, sanitary products such as diapers and napkins, filters such as air conditioners and air purifiers, soil water retention agents for infection prevention, and animals for infection prevention. Also included are food additives and food additives to prevent infection.
  • the inventor of the present application obtained a sugar derivative chemically crosslinked product by reacting the functional group of the sugar derivative with a polyfunctional compound for crosslinking.
  • the functional group used for cross-linking include a hydroxyl group, an amino group, and a strong carboxyl group of a sugar derivative.
  • polyfunctional compounds include polyfunctional isocyanates, polyfunctional epoxy compounds, polyfunctional carboxylic acids, polyfunctional carboxylic acid derivatives, polyfunctional halogenated compounds, polyfunctional vinyl compounds, and the like. Illustrated.
  • the crosslinking density can be controlled to about 0.0 1 m o 1 /% to about 15 m o 1 Z% with respect to the constituent sugars.
  • the sugar derivative chemically cross-linked product of the present invention becomes a gel when absorbing a liquid such as water, and becomes a rubber when plasticized by heating or adding a plasticizer as it is.
  • the functional group of the sugar derivative can be modified with a solubilizing or functionalizing compound, or modified with a dye compound.
  • a sugar derivative in which the hydroxyl group of the sugar derivative is acetylated is prepared.
  • anhydrous organic solvent such as DMSO
  • anhydrous acetic acid or acetic acid chloride anhydrous acetic acid or acetic acid chloride
  • acetylated sugar derivative in which the hydroxyl group of the sugar derivative is acetylated is prepared.
  • sugar derivatives can be solubilized and functionalized using other types of carboxylic anhydrides or carboxylic acid chlorides.
  • solubilizing and functionalizing sugar derivatives in addition to the above, hydroxypropylation, hydroxychetylation, carboxymethylation, sulfation, sulfonation, sulfur derivatization, tosylation, Mesylation, methylation, chloromethylation, formylation, sulfation, phosphorylation, phosphonic oxidation, phosphine oxidation, phosphorus derivatization, boric oxidation, boron oxidation, boron derivatization, silicification , Silyl derivatization, ditorolation, ditrosoation, ditolylation, norogeni ⁇ , hydroxy ⁇ , epoxy norelation, primary to quaternary amination, azomethination, azotization , Azoxylation, Diazoni Summation, Azide, Pyridylation, Virazilation, Triazine, Pyrolization, Piperidinization, Pyrimidation, Pyrrolidation,
  • Modification of a sugar derivative with a dye compound includes a method in which an arbitrary chromophore is chemically bonded to the hydroxyl group, amino group, or carboxyl group of the sugar derivative, or physically using electrostatic interaction. Examples of the bonding method can be given.
  • modifying the sugar derivative with a dye for example, the advantage of giving a color-added added value, the use in a color filter, the use as a highly dispersible pigment, and the use as a water-soluble dye The advantage of use is obtained.
  • a polyion complex which is a complex of the sugar derivative of the present invention and a polycation compound, could be obtained.
  • a polyion complex for example, salt absorbing agents, substance carriers, substance release agents, neutralizing agents, The advantage of a buffer is obtained.
  • the sugar derivative of the present invention can be used for various polyvalent metals. It can be formed by contact with an ion.
  • polyvalent metal ions Al, Se, Ti, V, Cr, Fe, Ga, Sr, Y, Zr, Nb, Ru, Rh, Pd, Cd , In, Ba, La, Hf, Ta, W, Re, Os, Ir, Hg, Pr, Bi, Ce, Nd, Sm, Eu, Gd , Tb, Dy, Ho, Er, Tm, Yb, Lu, and U.
  • polyvalent metal ions Al, Se, Ti, V, Cr, Fe, Ga, Sr, Y, Zr, Nb, Ru, Rh, Pd, Cd , In, Ba, La, Hf, Ta, W, Re, Os, Ir, Hg, Pr, Bi, Ce, Nd, Sm, Eu, Gd , Tb, Dy, Ho, Er, Tm, Yb, Lu, and U.
  • Fig. 1 shows a photograph of a swallowtail aphanothece sacrum agglomerate placed on the palm of the hand, and the lower part shows an optical microscope photograph of the swallowtail.
  • the filtrate was put into a dialysis membrane having a molecular weight cutoff of 8,00 and dialyzed against distilled water. This dialysis was performed by exchanging distilled water every morning until the external dialysate had a pH of 8.0 to 9.0.
  • aqueous sugar derivative solution was concentrated with an evaporator, and this concentrated liquid was poured into 100% isopropanol while stirring to obtain a fibrous sugar derivative shown in FIG.
  • the upper part of Fig. 2 shows a photograph of the fibrous material immediately after precipitation, and the lower part shows an optical micrograph.
  • this phenomenon of fibrosis consists of 1) the molecular weight of sugar derivatives being abnormally large, 2) having N-acetyl hexose that induces strong interchain forces, and 3) ) It seems to be related to having a sulfate group which is a functional group that dissolves well in water but not in alcohol.
  • sugar derivatives of Examples 1 and 2 above are peptides bound to each other.
  • polysaccharide peptide a sugar derivative having a peptide bound thereto
  • polysaccharide a sugar derivative to which a peptide is not bound
  • the number of sulfate groups per hydroxyl group is one third of the above mole fraction, that is, “0.0 3 9 8 8”. Was calculated to be. In other words, about 3.9 hydroxyl groups per 100 hydroxyl groups are sulfated. From a similar calculation, when elemental sulfur is 1.5% of the total sample weight, approximately 2.7 hydroxyl groups per 100 hydroxyl groups are sulfated.
  • a dilute aqueous solution of the above polysaccharide was diluted with isopropanol and dropped onto a carbon-coated copper lid and dried.
  • a transmission electron micrograph is shown in FIG.
  • the imaged image is considered to be in the form of a single chain.
  • the length of this molecular chain was estimated to be at least 5 ⁇ , as seen from the 100 nm size bar shown at the bottom of the figure. If the length of a monosaccharide assuming a molecular weight of 1 80 is 0.4 nm, this molecular chain is a 1 2 5 0 0 mer, so the molecular weight is 2 250,000. In the above transmission electron micrograph, many longer molecular chains were observed.
  • Fig. 7 Polysaccharide viscoelasticity tests were conducted using the rotational viscosity system shown in the upper part of Fig. 7.
  • an aqueous solution of polysaccharide having an appropriate concentration is contained in an appropriate container so as to be a disk shape having a thickness of 1 mm and a diameter of 2 O mm, and the aqueous solution is rotated at various shear rates. The rotation torque is sensed as viscosity.
  • the bottom of Fig. 7 shows the results of a total of three such measurements performed on an aqueous solution of polysaccharide with a concentration of 0.5 g / d 1.
  • aqueous solution of polysaccharide with a concentration of 0.5 g Z d 1 was placed between crossed polarizers, and the intensity of light transmitted through the aqueous solution was examined when shear stress was applied to the aqueous solution.
  • the measurement results are shown in the upper part of Fig. 8, and a photograph of the change in transmitted light intensity with increasing shear rate is shown in the lower part of Fig. 8.
  • the transmitted light intensity increased in two steps as the shear rate increased.
  • An increase in transmitted light intensity indicates that the birefringence of the aqueous solution is improved.
  • the increase in birefringence indicates that the molecular chains in the aqueous solution are oriented in one direction.
  • the primary one is derived from the fact that the molecular chain exhibits a liquid crystal phase, and the secondary one indicates that the linearity of the molecular chain itself has increased.
  • the concentration of the aqueous polysaccharide solution is greater than 0.5 g / d 1 Even if there is no breaking stress, it shows a liquid crystal phase.
  • the photograph in Fig. 9 is taken when an aqueous polysaccharide solution with a concentration of more than 0.5 g / d 1 is placed under an orthogonal polarizer. From this photograph, it was found that the aqueous solution showed strong birefringence and a liquid crystal phase in the natural state.
  • One such material is Schizophyllan, a neutral polysaccharide, but this is the first natural sulfated polysaccharide that exhibits liquid crystallinity.
  • First 0 Figure shows a photograph of a gel of the status of the polysaccharides alginate and the present invention in Y b 3 + ions presence of 1 0- 2 M.
  • the upper photo in Fig. 10 shows the gelation in neutrality or strength, with the left beaker being alginic acid and the right beaker being polysaccharides. Both gel formation is observed.
  • the photograph at the bottom of Fig. 10 shows the gelation status in acidity.
  • the left beaker is alginic acid
  • the right beaker is polysaccharides. Gel formation is observed only in polysaccharides.
  • Example 2 Molecular weight analysis was performed on a polysaccharide (sugar derivative according to the present invention) obtained by an extraction method different from that in Example 1. That is, when an appropriate amount of a living zinzinori water mixture was treated in an autoclave at 13.5 ° C. for 30 minutes, a somewhat turbid aqueous solution was obtained. This turbidity was removed by treatment for 50 minutes with an ultracentrifuge for 30 minutes to obtain a transparent viscous aqueous solution. This is concentrated under reduced pressure and poured into isopropanol. A polysaccharide was obtained. This fibrous polysaccharide was purified and analyzed in the same manner as in Example 1 to Example 2. As a result, it was found that this polysaccharide had the same functional group as in the extraction method of Example 1.
  • the polysaccharide obtained in this example was dissolved in a 0.1 M aqueous sodium nitrate solution, and the molecular weight was measured with an aqueous column. The results are shown in Fig. 14.
  • the polysaccharide has an extremely high molecular weight, a number average molecular weight of 16.9 MDa, a weight average molecular weight of 20.9 MDa, and a molecular weight distribution of 1.24. I understood. That is, the molecular weight of the polysaccharide is estimated to be about 20 MDa. Further, according to the analysis of the degree of sulfation as described above, the degree of sulfation per unit monosaccharide of the polysaccharide was 100% (maximum of 300%).
  • the aqueous polysaccharide solution was converted into a proton by treatment with ⁇ -ionized cation-exchanged resin, and then concentrated as it was with an enolator to partially add water. Decompose. When methanol was added to the concentrate, precipitation occurred. The supernatant was sucked out and dried to obtain a powder sample. 1 HNM with this sample
  • Example 15 In the 0.5% aqueous solution of the polysaccharide obtained in 5, 5% L-lysine, which corresponds to the amine, corresponds to 10% by mol of the monosaccharide mutated amount of the polysaccharide.
  • Example 15 The polysaccharide obtained in Example 15 was dissolved in DMSO and reacted with acetic anhydride to prepare an acetylated polysaccharide in which the hydroxyl group of the polysaccharide was acetylated.
  • the 1 H NMR spectrum of this acetylated polysaccharide is shown in FIG. A acetylated (one O c OCH 3) proton signal is observed at the position indicated by the arrow in the figure.
  • the polysaccharide obtained in Example 15 is an amine-directed green fluorescent dye.
  • FIG. 19 shows fluorescence micrographs of polysaccharides modified with these dyes. Force One photo ( a ) is modified with FITC, a color photo (b) is modified with congo red, and a color photo (c) is modified with alcian blue.
  • a 15% by weight aqueous solution of the polysaccharide obtained in Example 15 and a 0.5% by weight aqueous solution of hyaluronic acid were prepared, and their kinetic viscosity (Rotation viscosity: Unit Pa ⁇ s) was measured.
  • the kinematic viscosity was also measured when a 0.5% by weight aqueous solution of ascorbic acid was added to each of the above aqueous solutions.
  • Figure 20 shows the measurement results. The measurement result of the polysaccharide aqueous solution is shown on the left side of FIG. 20, and the measurement result of the hyaluronic acid aqueous solution is shown on the right side.
  • the graph labeled “ascorbic acid (0.5 wt%)” is when the ascorbic acid aqueous solution is added, and the graph labeled “ascorbic acid (1)” is when the ascorbic acid aqueous solution is not added. belongs to.
  • Figure 21 shows the high-resolution E S I — M S spectrum after acid degradation of the polysaccharide obtained in Example 15 with methanol / hydrochloric acid.
  • the table in Fig. 22 shows the molecular weights detected in this figure and other FT-MS spectra, which coincided with certain sugars at the millimeter level.
  • the value shown in the “m / z” column is the detected molecular weight.
  • the value obtained by adding the atomic weight of hydrogen (1.0 0 78 8) to this value is “m / z tasuH (MS: 1.0078) ”column.
  • entry numbers 1 to 4 are evidence of constituent sugars and evidence of the presence of sulfate groups. Entry numbers 5 and 6 prove that there are two consecutive hexoses. Entry number 7 proves that hexose is next to uronic acid. Next, entry number 8 indicates that N-acetylmethylmuramic acid is next to two consecutive hexoses.
  • sequences of hexose, hexose, and N-acetylmethylmuramate can be specified.
  • sequence structure of these trisaccharides constitutes the repeating unit of the polysaccharide according to this example or a part of the repeating unit, but it cannot be determined that this is the case.
  • Fig. 21 and Fig. 22 show the existence of carboxylic acid (muramic acid, uronic acid), amide (muramic acid), hydroxyl groups (all) and sulfate groups. Yes.
  • Example 15 when the polysaccharide obtained in Example 15 was decomposed by treating it with hydrochloric acid / methanol at 70 ° C. over several days and insolubilized in the middle, a solvent was added as needed. After the decomposition, the solvent is completely distilled off, and then treated with TMSI-C (trade name), a trimethylsilylating agent manufactured by GL Sciences, and measured directly with a gas chromatography. did. The obtained results are shown in FIG.
  • TMSI-C trade name
  • Figure 23 shows that the polysaccharides constituting the polysaccharide are Fuc (fucose), Rha (rhamnose), Xyl (xylose), Ara (arabinose), Man (mannose), Glc (glucose), The presence of Gal (galactose), GlcA (glucuronic acid), GalA (galacturonic acid), and GalN (galactosamine) was confirmed.
  • Fucose, rhamnose) is a 6-deoxy sugar.
  • Xylose and arabinose are pentoses that have lost 6th place.
  • Glucose, mannose and galactose are hexoses.
  • Gunoleconic acid and galacturonic acid are uronic acids.
  • Darcosamine is a hexosamine.
  • Fig. 24 shows the test results of the simple herpesvirus type 2 growth inhibitory effect
  • Fig. 25 shows the test result of the simple herpesvirus type 2 inactivation effect.
  • Alkaline-extracted sample refers to the polysaccharide targeted in the first example group
  • high-pressure high-temperature extracted sample refers to the polysaccharide targeted in the second example group.
  • compositions (i) to (xi) containing a sugar derivative as an active ingredient were prepared.
  • Facial cleanser i) Facial cleanser, makeup remover, sarcophagus, shampoo, rinse, conditioner Ishion, bath salt, toothpaste
  • Hair packs hair polishes, hair dyes, hair styling waxes, hair styling creams, hair styling mousses, hair styling gels, hair styling sprays, hair growth agents
  • Nail coating agent Nail coating agent, teak, eyeliner, fan deionization, maskara, lipstick, eye shadow, eyebrow i v) lotion, serum, beauty cream, beauty gel, Latex, hand cream, hand gel, pack
  • V i Skin lotion, essence, beauty cream, beauty gel, milky lotion, face wash, makeup remover, pack agent, shave after mouth shaving
  • V i i Anti-wrinkle, lotion, beauty liquid, beauty cream, beauty gel, milky lotion, face wash, makeup remover, pack agent, shave after mouth
  • a food composition containing sugar derivative G1 or sugar derivative G2 as an additive for water retention i) A food composition containing sugar derivative G1 or sugar derivative G2 as an additive for water retention.
  • Sugar derivative G 1 or sugar derivative G 2 is added as an anti-inflammatory agent, antioxidant, cancer prevention function agent, fat absorption inhibitor, lipid metabolism improving agent, anti-stress function agent, anti-allergy function agent.
  • a food composition comprising as an intestinal regulating agent, a blood pressure regulating functional agent, a blood glucose level elevation inhibiting functional agent or a diet functional agent.
  • Sugar derivative G1 or sugar derivative G2 is added to thickener stabilizer, food adhesive, food polish, food gel substrate, colloidal food stabilizer, food colorant, food storage. , Food composition containing pH stabilizer for food or additive for adjusting throat.
  • compositions i) to viii) containing a sugar derivative as an active ingredient were prepared.
  • compositions i) to xi) containing a sugar derivative as an active ingredient were prepared.
  • Fiber base or film base for food packaging including oral and suppositories, artificial skin constituents, contact lens materials, joint impact absorbing materials, impact absorbing sheets, artificial saliva Anti-adhesion agent, diagnostic imaging contrast agent, reliable coating agent, condom-coated gel, humidity control sheet
  • V i Heavy metal adsorption gel, water-soluble powder for metal adsorption, metal adsorption filter, gel substrate for fragrance or deodorant, deodorant, deodorization filter, fiber material with deodorization function
  • Coating agent for leather products coating agent for resin materials, coating agent for paper products, coating agent for textile products, surface protection agent, spray for coating
  • sugar derivative preparations for various uses containing useful sugar derivatives having a novel polysaccharide structure derived from sisendinori.

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Engineering & Computer Science (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Biotechnology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Epidemiology (AREA)
  • Natural Medicines & Medicinal Plants (AREA)
  • Polymers & Plastics (AREA)
  • Mycology (AREA)
  • Dermatology (AREA)
  • Molecular Biology (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Alternative & Traditional Medicine (AREA)
  • Materials Engineering (AREA)
  • Medical Informatics (AREA)
  • Microbiology (AREA)
  • Biochemistry (AREA)
  • Birds (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Botany (AREA)
  • Nutrition Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Food Science & Technology (AREA)
  • Toxicology (AREA)
  • Virology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Coloring Foods And Improving Nutritive Qualities (AREA)
  • Cosmetics (AREA)
  • Medicines Containing Plant Substances (AREA)

Abstract

La présente invention concerne une préparation de dérivé de glucide qui contient un dérivé de glucide spécifique G1 ou G2 dérivé de Aphanothece sacrum en tant que composant actif et est utilisée pour différentes applications fonctionnelles telles que l'absorption d'eau, l'utilisation antimicrobienne, l'utilisation anticancéreuse, la promotion de la santé pour des aliments et l'augmentation de la viscosité en tant que composition cosmétique, composition alimentaire, composition pharmaceutique, composition de matériau et similaire. En conséquence, il est proposé une préparation de dérivé de glucide nouvelle et utile qui contient un dérivé de glucide dérivé de Aphanothece sacrum.
PCT/JP2009/054103 2008-03-14 2009-02-26 Préparation de dérivé de glucide WO2009113435A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2008066702A JP2009221136A (ja) 2008-03-14 2008-03-14 糖誘導体製剤
JP2008-66702 2008-03-14

Publications (1)

Publication Number Publication Date
WO2009113435A1 true WO2009113435A1 (fr) 2009-09-17

Family

ID=41065104

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2009/054103 WO2009113435A1 (fr) 2008-03-14 2009-02-26 Préparation de dérivé de glucide

Country Status (2)

Country Link
JP (1) JP2009221136A (fr)
WO (1) WO2009113435A1 (fr)

Cited By (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011013496A1 (fr) * 2009-07-31 2011-02-03 国立大学法人北陸先端科学技術大学院大学 Procédé pour la préparation d'un polysaccharide issu d'aphanothece sacrum ayant une teneur réduite en métaux trivalents
JP2011068606A (ja) * 2009-09-25 2011-04-07 Kumamoto Univ 徐放性担体及び同徐放性担体を用いた薬剤並びに同薬剤を用いたドラッグデリバリーシステム
JP2011074002A (ja) * 2009-09-30 2011-04-14 Daito Kasei Kogyo Kk カプセルおよびそれを含有する化粧料
JP2011074001A (ja) * 2009-09-30 2011-04-14 Daito Kasei Kogyo Kk カプセルおよびそれを含有する化粧料
JP2012217972A (ja) * 2011-04-13 2012-11-12 Kajima Corp 凝集処理方法
JP2012246443A (ja) * 2011-05-30 2012-12-13 Masao Funakoshi 石鹸
CN103263665A (zh) * 2013-05-09 2013-08-28 中国药科大学 盐生隐杆藻胞外多糖免疫佐剂
JP2014133809A (ja) * 2013-01-10 2014-07-24 Kumamoto Univ スイゼンジノリ多糖体低分子化物を用いた新規な核酸デリバリーシステム、及び該システムに用いる核酸デリバリーキャリアの調製方法
JP2014205751A (ja) * 2013-04-11 2014-10-30 日立化成株式会社 スイゼンジノリ多糖体低分子化物及びスイゼンジノリ由来多糖類の低分子化方法
JP2015085219A (ja) * 2013-10-28 2015-05-07 鹿島建設株式会社 凝集処理方法
WO2015076244A1 (fr) * 2013-11-19 2015-05-28 国立大学法人熊本大学 Agent anti-inflammatoire contenant un polysaccharide de faible poids moléculaire issu d'aphanothece sacrum
WO2016009982A1 (fr) * 2014-07-14 2016-01-21 参天製薬株式会社 Agent therapeutique pour soigner des troubles kératoconjonctifs
CN106629922A (zh) * 2017-01-07 2017-05-10 内蒙古民族大学 一种有机物降解剂及其制备方法
CN108084863A (zh) * 2017-12-01 2018-05-29 蒋春霞 一种合成革用水性聚氨酯表面处理剂的制备方法
CN108203218A (zh) * 2018-01-05 2018-06-26 金碳环境科技（天津）有限公司 一种含油污泥的无害化处理工艺
CN108513244A (zh) * 2017-02-27 2018-09-07 识骅科技股份有限公司 用于扬声器的纳米碳管复合振动膜及其制造方法
CN109678278A (zh) * 2019-01-21 2019-04-26 河南城建学院 一种污染场地的地下水处理方法
CN114805453A (zh) * 2022-06-30 2022-07-29 中国科学院烟台海岸带研究所 一种阳离子菊糖烟酸接枝衍生物及其制备方法和应用

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2013082649A (ja) * 2011-10-07 2013-05-09 Daito Kasei Kogyo Kk スイゼンジノリ由来糖誘導体被覆処理粉体およびその製造方法並びに化粧料
JP6083726B2 (ja) * 2012-04-11 2017-02-22 鹿島建設株式会社 液中放射性物質処理方法
JP6295103B2 (ja) * 2014-03-04 2018-03-14 グリーンサイエンス・マテリアル株式会社 水膨潤性シート
JP6412414B2 (ja) * 2014-11-14 2018-10-24 グリーンサイエンス・マテリアル株式会社 スイゼンジノリ多糖体−コラーゲン複合体
JP6661402B2 (ja) * 2015-02-24 2020-03-11 学校法人君が淵学園 内因系血液凝固反応を特異的に阻害する抗血栓剤
JP6858367B2 (ja) * 2017-02-03 2021-04-14 国立大学法人 熊本大学 ウイルス吸着剤、該吸着剤を含むウイルス吸着性部材およびマイクロバイサイド
JP7094796B2 (ja) * 2017-06-30 2022-07-04 オーミケンシ株式会社 レーヨン繊維
JP6996460B2 (ja) * 2018-09-10 2022-01-17 国立大学法人 熊本大学 腎臓病の進行抑制剤、予防剤、および治療剤
CN113226278B (zh) * 2019-01-02 2023-07-21 宝洁公司 含有肽化合物和水前寺海苔胞外多糖提取物的皮肤护理组合物
WO2022114111A1 (fr) * 2020-11-27 2022-06-02 マルホ株式会社 Composition pharmaceutique ou cosmétique

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008062574A1 (fr) * 2006-11-22 2008-05-29 Tatsuo Kaneko Dérivé de sucre et ses utilisations

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008062574A1 (fr) * 2006-11-22 2008-05-29 Tatsuo Kaneko Dérivé de sucre et ses utilisations

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
OKAJIMA-KANEKO, M. ET AL.: "Extraction of novel sulfated polysaccharides from Aphanithece sacrum (Sur.) Okada, and its spectroscopic characterization", PURE APPL. CHEM, vol. 79, no. 11, 2007, pages 2039 - 2046 *

Cited By (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011013496A1 (fr) * 2009-07-31 2011-02-03 国立大学法人北陸先端科学技術大学院大学 Procédé pour la préparation d'un polysaccharide issu d'aphanothece sacrum ayant une teneur réduite en métaux trivalents
JP5607051B2 (ja) * 2009-07-31 2014-10-15 国立大学法人北陸先端科学技術大学院大学 三価金属低減スイゼンジノリ由来多糖体製造方法
JP2011068606A (ja) * 2009-09-25 2011-04-07 Kumamoto Univ 徐放性担体及び同徐放性担体を用いた薬剤並びに同薬剤を用いたドラッグデリバリーシステム
JP2011074002A (ja) * 2009-09-30 2011-04-14 Daito Kasei Kogyo Kk カプセルおよびそれを含有する化粧料
JP2011074001A (ja) * 2009-09-30 2011-04-14 Daito Kasei Kogyo Kk カプセルおよびそれを含有する化粧料
JP2012217972A (ja) * 2011-04-13 2012-11-12 Kajima Corp 凝集処理方法
JP2012246443A (ja) * 2011-05-30 2012-12-13 Masao Funakoshi 石鹸
JP2014133809A (ja) * 2013-01-10 2014-07-24 Kumamoto Univ スイゼンジノリ多糖体低分子化物を用いた新規な核酸デリバリーシステム、及び該システムに用いる核酸デリバリーキャリアの調製方法
JP2014205751A (ja) * 2013-04-11 2014-10-30 日立化成株式会社 スイゼンジノリ多糖体低分子化物及びスイゼンジノリ由来多糖類の低分子化方法
CN103263665A (zh) * 2013-05-09 2013-08-28 中国药科大学 盐生隐杆藻胞外多糖免疫佐剂
JP2015085219A (ja) * 2013-10-28 2015-05-07 鹿島建設株式会社 凝集処理方法
WO2015076244A1 (fr) * 2013-11-19 2015-05-28 国立大学法人熊本大学 Agent anti-inflammatoire contenant un polysaccharide de faible poids moléculaire issu d'aphanothece sacrum
WO2016009982A1 (fr) * 2014-07-14 2016-01-21 参天製薬株式会社 Agent therapeutique pour soigner des troubles kératoconjonctifs
CN106535904A (zh) * 2014-07-14 2017-03-22 参天制药株式会社 角结膜病变治疗剂
CN106629922A (zh) * 2017-01-07 2017-05-10 内蒙古民族大学 一种有机物降解剂及其制备方法
CN108513244A (zh) * 2017-02-27 2018-09-07 识骅科技股份有限公司 用于扬声器的纳米碳管复合振动膜及其制造方法
CN108084863A (zh) * 2017-12-01 2018-05-29 蒋春霞 一种合成革用水性聚氨酯表面处理剂的制备方法
CN108203218A (zh) * 2018-01-05 2018-06-26 金碳环境科技（天津）有限公司 一种含油污泥的无害化处理工艺
CN109678278A (zh) * 2019-01-21 2019-04-26 河南城建学院 一种污染场地的地下水处理方法
CN114805453A (zh) * 2022-06-30 2022-07-29 中国科学院烟台海岸带研究所 一种阳离子菊糖烟酸接枝衍生物及其制备方法和应用

Also Published As

Publication number Publication date
JP2009221136A (ja) 2009-10-01

Similar Documents

Publication Publication Date Title
WO2009113435A1 (fr) Préparation de dérivé de glucide
JP4066443B1 (ja) 糖誘導体とその利用
Meftahi et al. Nanocelluloses as skin biocompatible materials for skincare, cosmetics, and healthcare: Formulations, regulations, and emerging applications
DE60307603T2 (de) Zellwandderivate aus biomasse und herstellung davon
EP2861204B1 (fr) Épaississants micellaires à base d'alkyle glycoside pour des systèmes tensioactifs
KR20230020444A (ko) 덱스트란-알파-글루칸 그래프트 공중합체 및 이의 유도체
US20080226740A1 (en) Marine algal extracts comprising marine algal polysaccharides of low degree polymerizaton, and the preparation processes and uses thereof
KR20140034905A (ko) 카시아 유도체
TW200938208A (en) Crosslinked hyaluronic acid in emulsion
CN101415731A (zh) 新型低分子透明质酸和/或其盐以及使用其的化妆品、医药组合物和食品组合物
KR20160065954A (ko) 디히드록시알킬 치환된 폴리갈락토만난, 및 그의 제조 및 사용 방법
KR20130115276A (ko) 아크릴레이트 공중합체 증점제
WO1999041288A1 (fr) Saccharides sulfates
KR101816792B1 (ko) 바이오셀룰로오스 미세섬유 수분산체 네트워크 조성물
JP6555431B2 (ja) 保湿外用剤
KR20010031274A (ko) 폴리히드록실화 유기 화합물과 배합된 실질적으로무정형인 셀룰로스 나노피브릴의, 화장용 제제에서의 용도
KR101144493B1 (ko) 저분자의 알지네이트, 후코이단 또는 은-알지네이트를 유효성분으로 함유하는 항균 화장료 조성물
De Carvalho et al. Chitosan as an oral antimicrobial agent
JP2004210895A (ja) 免疫機能を有する可能性β−グルカンの製造方法及び用途
KR20100131518A (ko) 가교결합 방법 및 그 방법으로 제조된 가교결합된 다당류
KR102025818B1 (ko) 천연 항균제 및 이의 제조방법
JP6246474B2 (ja) 多糖体，皮膚バリア機能改善剤及び皮膚保湿剤
JP2011074041A (ja) コラーゲン組成物及びその製造方法
CN115161207A (zh) 半乳糖酵母液的制备方法、半乳糖酵母粉及在亮肤淡化皱纹的应用
JP3656780B2 (ja) 化粧料用組成物及びその製造方法並びにこれを配合した化粧品

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 09718750

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 09718750

Country of ref document: EP

Kind code of ref document: A1