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WO2003090770A1 - Procede de production de matiere riche en proanthocyanidine - Google Patents

Procede de production de matiere riche en proanthocyanidine Download PDF

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Publication number
WO2003090770A1
WO2003090770A1 PCT/JP2002/005879 JP0205879W WO03090770A1 WO 2003090770 A1 WO2003090770 A1 WO 2003090770A1 JP 0205879 W JP0205879 W JP 0205879W WO 03090770 A1 WO03090770 A1 WO 03090770A1
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WIPO (PCT)
Prior art keywords
proanthocyanidin
chitin
water
extraction
extract
Prior art date
Application number
PCT/JP2002/005879
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English (en)
Japanese (ja)
Inventor
Isao Kouno
Takashi Tanaka
Gen-Ichiro Nonaka
Kinya Takagaki
Original Assignee
Toyo Shinyaku Co., Ltd.
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 Toyo Shinyaku Co., Ltd. filed Critical Toyo Shinyaku Co., Ltd.
Priority to AU2002311198A priority Critical patent/AU2002311198A1/en
Priority to JP2003587403A priority patent/JP3595816B2/ja
Publication of WO2003090770A1 publication Critical patent/WO2003090770A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
    • C07D311/60—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with aryl radicals attached in position 2
    • C07D311/62—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with aryl radicals attached in position 2 with oxygen atoms directly attached in position 3, e.g. anthocyanidins
    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
    • A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline 
    • 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
    • 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
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • 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
    • 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

Definitions

  • the present invention relates to a method for efficiently producing promyloantocyanidin, which is useful as a raw material for producing foods, cosmetics, pharmaceuticals, and the like, for improving vascular enhancement, high blood pressure, and improving coldness.
  • Field background technology is useful as a raw material for producing foods, cosmetics, pharmaceuticals, and the like, for improving vascular enhancement, high blood pressure, and improving coldness.
  • Proanthocyanidins are polymerized or condensed tannins present in various plants, and are formed by condensation or polymerization (hereinafter, referred to as condensation polymerization) using flavan-1-ol or flapan-1,4-diol as a structural unit. It is a group of bound compounds. These are given their names because they produce anthocyanins such as cyanidin, delphidin, and pelargogin by acid treatment.
  • proanthocyanins having a low polymerization degree are suitably used.
  • the degree of polymerization is preferably a polycondensate of 2 to 30 (2 to 30 mer), a polycondensation of 2 to 10 is more preferable, and a polycondensate of 2 to 10 (2 to 10 mer).
  • 2-4 polycondensates (2-4 tetramers) are more preferably used.
  • OPCs oligopolymers
  • OPC is a type of polyphenols, a powerful antioxidant produced by plants, mainly found in plant leaves, bark, fruit bark and seed parts. Ingredient Physically, it is found in grape seeds, pine bark, peanut skin, ginkgo biloba, escacassia fruit, and cowberry. It is also known that OPCs are contained in cola nuts in West Africa, the roots of Ratania in Peru, and green tea in Japan. OPC is a substance that cannot be produced in the human body.
  • OPC In addition to its antioxidant effect, OPC also has the effect of reducing plaque (gum) by suppressing the growth of bacterium in the oral cavity; the effect of restoring the elasticity of blood vessels; the riboprotein in blood is damaged by reactive oxygen species Effect of preventing damaged fat from aggregating on the inner wall of blood vessels and adhering cholesterol; effect of regenerating vitamin E decomposed by active oxygen; effect of vitamin E as an enhancer It is known to have effects and the like.
  • tannin a polymer of flavan-1-ol and / or flavan-1,4-diol, and chitin, chitosan, and their derivatives have antibacterial activity and bactericidal activity against Staphylococcus aureus, Salmonella, S. typhi, and cholera.
  • the effect is significant.
  • MRSA methicillin-resistant staphylococci
  • Proanthocyanidins are generally obtained by extraction from plants.
  • the solvent used for the extraction include water; organic solvents such as methanol, ethanol, acetone, hexane, and ethyl acetate; and mixtures thereof (Japanese Patent Laid-Open Publication No. Hei 11-181488).
  • simply extracting with a solvent results in low recovery and low purity of oral anthocyanidins. Therefore, in order to use it as a raw material for health foods, cosmetics, and pharmaceuticals, additional processes such as concentration and purification are required to increase the purity, which is costly and time consuming.
  • Japanese Patent Application Laid-Open No. 5-2792864 describes a method for recovering polyphenols containing proanthocyanidins.
  • polyphenols are adsorbed to chitin, and the chitin adsorbed by the polyphenols is converted to polyphenol.
  • the adsorbed polyphenols are polyphenols having a high degree of polymerization, and the above-mentioned physiological activity is extremely low. Low bioactivity.
  • chitin, chitosan, and their derivatives are known to have antibacterial activity.
  • the present inventors diligently studied a method for efficiently obtaining proanthocyanidin, extracted proanthocyanidin from a plant, and contacted the obtained extract with chitin, chitosan, or a derivative thereof. By recovering the non-adsorbed substance, it was found that a proanthocyanin-containing substance containing a large amount of OPC having high physiological activity can be efficiently obtained.
  • the inventors have found that a proanthocyanidin-containing substance having a higher OPC content can be obtained by further treating the proanthocyanidin-containing substance with a synthetic resin-based adsorbent, thereby completing the present invention.
  • the present invention provides a method for producing a proanthocyanidin-containing substance, the method comprising: ( a ) obtaining an extract or juice from a plant by extraction or pressing; and (b) the extract or juice. Is contacted with chitin, chitosan or a derivative thereof to recover non-adsorbed substances.
  • the extraction is a hot water extraction.
  • the method further includes the step of (c) contacting the non-adsorbed substance obtained in the step (b) with the synthetic resin-based adsorbent.
  • the present invention provides a proanthocyanin-containing substance obtained by the above production method.
  • the solid content of the proanthocyanidin-containing material contains oligomeric 'proanthocyanidin in a proportion of 40% by weight or more.
  • the present invention is obtained by contacting an extract or juice obtained from a plant with chitin, chitosan, or a derivative thereof, and then recovering the insoluble component containing the chitin, chitosan, or a derivative thereof.
  • the plant used in the present invention is a plant containing proanthocyanidin, and its type is not particularly limited. Bark of cedar, cypress, pine and other trees that are high in proanthocyanidins; grape seeds, peels, and fruits; peanut thin bark; ichiyo, cacao; tea leaves and tea extract; sorghum cane; apple fruit; Yacon leaves; elder berries; false acacia fruit; lingonberries; cola nuts (eg, cola nuts in West Africa); and roots of ratania (eg, ratha in Peru). Of these, pine bark, pud seed and pericarp, peanut thin skin, and the like are particularly preferably used.
  • proanthocyanin is extracted from the plant, or juice is obtained from the plant.
  • the plant is preferably crushed to an appropriate size from the viewpoint of extraction efficiency to increase the surface area per volume.
  • the crushing method is not particularly limited. For example, a crushed material processed by a cutter, a slicer, etc .; a crushed material processed by a mixer, a juicer, a blender, a masco mouth whatsoever, etc .;
  • the size of the shredder or crushed material is 0.1 to 10 cm, preferably 0.1 to 5 cm.
  • An organic solvent such as water, ethanol, methanol, or ethyl acetate may be added during the crushing to increase the crushing efficiency.
  • Water or an organic solvent is used as the extraction solvent.
  • organic solvents include methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 2-butanol, butane, acetone, hexane, cyclohexane, propylene glycol, hydrous ethanol, hydrous propylene glycol, Examples include thimethylenoketone, glycerin, methyl acetate, ethyl acetate, getyl ether, dichloromethane, edible fats and oils, 1,1,1,2-tetrafluoroethane, 1,1,2-trichloroethene, and the like.
  • a mixed solvent of water and an organic solvent is also preferably used. These may be used alone or as a mixture of two or more solvents. From the viewpoint of waste liquid treatment during production, water is
  • the amount of the extraction solvent to be added to the plant is set in consideration of the target proanthocyanidin concentration and the extraction efficiency.
  • the weight ratio of plant: water is 1: 5 to 1:50, preferably 1:10 to 1:20.
  • the amount of extraction solvent to be added may be adjusted in consideration of the amount used for crushing.
  • extraction is performed with hot water at 50 to 120 ° C, preferably 70 to 100 ° C. Hot water may be added to the plant, or water may be added to the plant and then heated. The extraction is generally performed for 10 minutes to 24 hours, but is determined by the extraction temperature.
  • an extraction method using an organic solvent extraction by warming or supercritical fluid extraction may be performed.
  • a warm extraction method using an organic solvent a method of adding a heated solvent to a plant or a method of adding a solvent to a plant and heating is used.
  • a warm extraction method using an organic solvent a method of adding a heated solvent to a plant or a method of adding a solvent to a plant and heating is used.
  • a ground plant use a 5: 1 volume of water-ethanol mixed solvent with a water: ethanol ratio of 1: 1 by weight as an extraction solvent at 70-75 ° C. While refluxing, there is a method of stirring for 3 hours.
  • an organic solvent set the extraction temperature below the boiling point of the organic solvent. There is a need to.
  • the supercritical fluid extraction method is a method of extracting a target component using a supercritical fluid, which is a fluid that has exceeded the critical point (critical temperature, critical pressure) of the gas-liquid of a substance.
  • a supercritical fluid a fluid that has exceeded the critical point (critical temperature, critical pressure) of the gas-liquid of a substance.
  • the supercritical fluid carbon dioxide, ethylene, propane, nitrous oxide (laughing gas) or the like is used, and carbon dioxide is preferably used.
  • the supercritical fluid extraction method comprises an extraction step of extracting a target component with a supercritical fluid, and a separation step of separating the target component and the supercritical fluid. Examples of the separation step include a separation step based on a change in pressure, a separation step based on a change in temperature, and a separation step using an adsorbent and an absorbent. These may be used alone or in combination.
  • supercritical fluid extraction by an entrainer addition method may be performed.
  • this method for example, ethanol, propanol, n-hexane, acetone, toluene, other lower aliphatic alcohols; aliphatic hydrocarbons; aromatic hydrocarbons;
  • any of a batch type, a semi-continuous type, and a continuous type may be used.
  • the plant When juice is obtained from a plant, the plant is directly squeezed or, after being appropriately cut or crushed, squeezed.
  • This method is suitably adopted when a plant having a high water content is used.
  • a plant having a high water content For example, in the case of grape berries, squeezing produces squeezed juice containing pulp anthocyanin.
  • a crushed plant body containing solid matter derived from the plant body obtained by crushing the plant body (for example, the crushed grape fruit) is also used in the same manner as squeezed juice.
  • the crushed plant containing the solid content of is also included in the juice.
  • extract the obtained extract or squeezed juice (hereinafter referred to as extract, etc.) and chitin, chitosan, or a derivative thereof (hereinafter, chitin, chitosan, and at least one of these derivatives are referred to as chitins) ) And.
  • this step is referred to as a contact step.
  • the chitin used in the contacting step may be used in the form of powder, or may be used in the form of fibers, fibrils, films, porous bodies, microbeads, resins, and the like. In the contacting step, any method may be used as long as the extract or the like contacts the chitin.
  • a chitin derivative may be used, for example, a synthetic resin as a carrier, a chitin resin having chitin bound thereto may be packed in a column, and an extraction solution may be passed through a column.
  • a batch method for removing chitins after a certain period of time When the extract or the like contains an organic solvent, it is necessary to remove the organic solvent and the power to dilute the extract or the like to such an extent that chitins are not dissolved in the organic solvent.
  • insolubles contained in the extract and the like in advance in consideration of clogging of the column and the like.
  • the removal of insolubles includes methods commonly used by those skilled in the art, for example, filtration and centrifugation.
  • Filtration is preferably used in view of the processing time. Filtration can be performed at 50-100 ° C., and the higher the temperature, the more proanthocyanin can be recovered.
  • the reaction is preferably performed at 50 ° C. or higher, more preferably at 70 ° C. or higher. More proanthocyanidins can be recovered by washing the filtered insolubles with hot water or a heated solvent at 70 ° C or more.
  • the extract obtained from the viewpoint of adsorption efficiency it is preferable to cool the extract obtained from the viewpoint of adsorption efficiency to chitins.
  • it is cooled to 4 to 30 ° C. Cooling includes natural cooling by cooling; water or ice; or forced cooling using a cooling device such as a freezer and a refrigerator.
  • the extract is passed through a column packed with chitins (eg, chitin resin).
  • chitins eg, chitin resin
  • the amount of chitins may be appropriately determined according to its properties, shape, and raw material plant.
  • the chitin resin is preferably 5 to 100 g, more preferably 10 to 80 g, per 100 g of pine bark. g Used.
  • the extract is passed through a column filled with chitins, the extract is washed with 100 mL of water, and the liquid and the washings that have passed through the column are collected to obtain a proanthocyanidin-containing substance.
  • the proanthocyanin-containing substance also includes a concentrate, a powder, and the like obtained by a method usually used by those skilled in the art.
  • the treatment with chitins in the batch method is, for example, based on the extract obtained from 100 g of pine bark, chitins are preferably used in an amount of 5 to 100 g, more preferably 10 to 80 g. It is preferable to add g and perform the reaction for 1 to 3 hours with stirring. After the treatment, the chitins are removed by filtration or centrifugation, whereby a proanthocyanin-containing substance can be obtained.
  • proanthocyanin-containing substance By treating the obtained proanthocyanin-containing substance with a synthetic resin-based adsorbent, impurities such as saccharides and organic acids are further removed and purified. That is, the OPC content was increased by bringing the proanthocyanidin-containing substance into contact with the synthetic resin-based adsorbent, adsorbing the proanthocyanidin onto the synthetic resin-based adsorbent, and eluting with a predetermined solvent.
  • a proanthocyanidin-containing substance can be obtained.
  • the synthetic resin-based adsorbent used for purification include organic resins, ion exchange resins, silica gel, and reversed-phase silica gel.
  • an aromatic resin for example, an aromatic resin, an acrylic acid-based methacrylic resin, an atariloetrile aliphatic-based resin, and the like can be used, and an aromatic-based resin is preferable.
  • an aromatic resin an aromatic resin having a hydrophobic substituent, an unsubstituted type PC leak 2/05879
  • an aromatic resin obtained by subjecting an unsubstituted type to a special treatment is more preferable.
  • general-purpose aromatic resins include styrene-dibielbenzene resins. These resins are preferably porous. Such synthetic resins are commercially available.
  • HP-10, HP-20, HP-21, HP-30, HP-40, HP-50 (all of which are non-replaceable) Base type aromatic resin, all trade names, manufactured by Mitsubishi Chemical Corporation); SP-825, SP-800, SP-850, SP-875 (above, special treatment was applied to the unsubstituted type) Aromatic resins, all trade names, manufactured by Mitsubishi Chemical Corporation); SP-900 (aromatic resins, trade name, manufactured by Mitsubishi Chemical Corporation); Amberlite (registered trademark), XAD-2, XAD-4, XAD-16, XAD-2000 (above, aromatic resins, all trade names, manufactured by Organo Corporation); SP-205, SP-206, SP- as Diaion (registered trademark) 207 (above, aromatic resin having a hydrophobic substituent, both are trade names, manufactured by Mitsubishi Chemical Corporation); HP-2MG, EX-0021 (above, aromatic resin having a hydrophobic substituent, all trade names, manufactured by Mitsubishi Chemical Corporation); Amberlite (registered trademark) as XAD-7,
  • any of a cation exchange resin and an anion exchange resin can be used.
  • Commercially available ion exchange resins include, for example, CG-4000, CG-5000, CG-6000, CG-8000 (Bareite (registered trademark) -based cation exchange resins) (All of which have trade names of sulfonate groups as functional groups.
  • IR-116, IR-118, IR-120B, IR-122, IR-124 (all of which have a sulfonate group as a functional group; all are trade names, manufactured by Organo Corporation); XT- 1007, XT-1009, XT-1002 (Resin, a resin having a sulfonate group as a functional group, all trade names, manufactured by Organo Co., Ltd.); OPT I PORE—XUS 402 85. as a weakly basic anion exchange resin. 00, OPT I PORE-XUS 40390.00 (the above is a resin having a quaternary amine as a functional group, all of which are trade names, manufactured by Dow Chemical Co., Ltd.).
  • the elution solvent when using the ion exchange resin is preferably water, the column temperature is 50 to 120 ° C., and the inside of the column is preferably under normal pressure or pressurized state.
  • the amount of the synthetic resin-based adsorbent may be appropriately set depending on the type of the solvent, the type of the synthetic resin-based adsorbent, and the like. For example, it is preferable to use a synthetic resin-based adsorbent in an amount of 0.01 to 5 times the weight of the solid content in the proanthocyanin-containing material.
  • a column is filled with a synthetic resin-based adsorbent
  • the proanthocyanidin-containing substance is passed through the column, and then the weight of the synthetic resin-based adsorbent is reduced. 5 to 10 times the weight of water is allowed to pass. This removes saccharides and organic acids as impurities.
  • the proanthocyanin is eluted with a predetermined solvent.
  • the solvent include water, methanol, ethanol, ethyl acetate, chloroform, and a mixture thereof.
  • a mixed solvent of water and ethanol is used.
  • the mixing ratio of water and ethanol depends on the synthetic resin adsorbent used. In the case of Diaion HP-20, the water: ethanol ratio is 1: 1 to 4: 1 by volume. It is. In this way, a proanthocyanidin-containing substance having an increased OPC content is obtained.
  • the OPC contained in the solid content of the proanthocyanidin-containing material obtained through the above steps was 80% by weight. / 0 or more, preferably 95% by weight or more.
  • the proanthocyanin-containing material produced by the above method can be concentrated to produce a food material.
  • concentration various methods such as membrane concentration, heat concentration, vacuum (reduced pressure) concentration, and freeze concentration are used.
  • these proanthocyanin-containing substances are sterilized and stored. Sterilization is performed by a method used by those skilled in the art, such as air stream sterilization, high-pressure sterilization, and heat sterilization.
  • these proanthocyanidin-containing substances may be sterilized, concentrated, dried, and powdered. Drying is performed by a method commonly used by those skilled in the art. Among them, freeze drying, vacuum drying, and spray drying are preferably used.
  • the proanthocyanidin-containing product obtained by the above production method can be used as a raw material for foods, cosmetics, and pharmaceuticals.
  • the resulting proanthocyanidin-containing substance can be used as a drink, a food and drink, etc.
  • the proanthocyanidin-containing material is not only used for eating and drinking as it is, but also mixed with excipients, bulking agents, binders, thickeners, emulsifiers, fragrances, food additives, seasonings, etc.
  • it can be formed into granules, tablets and the like.
  • it can be mixed with royal jelly, vitamins, protein, calcium, chitosan, lecithin, caffeine, etc., and the taste can be adjusted with a sugar solution and seasonings.
  • they are made into capsules such as hard capsules and soft capsules, pills, or tea bags.
  • Chitins that come into contact with extracts, etc. contain tannins derived from plants as raw materials and have antibacterial as well as deodorant effects. It can be used as a material.
  • chitins also have an antibacterial effect, for example, antibacterial activity against O-157 and Staphylococcus aureus. It has an effect.
  • the chitin is used for drinking water, water for drinking, water for bathing, water for cooking, water for washing, water for appreciation fish, tableware and food cleaning.
  • Water purification material for purifying water for washing, facial cleansing water, toilet water, toilet running water, pool water, flower arrangement and gardening water; filter material (air conditioner, air purifier Machines Clean room filters, water purification filters, etc.); Fans and moldings around the fan; Refrigerator inner wall panels; Clothing (clothing, interlining, lining, ebloons, socks, socks, etc.); Footwear (shoes, slippers) Personal belongings (towels, scarves, scarves, belts, hats, gloves, tablecloths, umbrellas, bags, bags, wallets, etc.); daily necessities' kitchen supplies (toothbrushes, clothes brushes, hairbrushes, Food, food Washing, rag, fukin, rubbing, etc .; medical supplies, welfare-related supplies, sanitary supplies, sanitary materials, (surgical gowns, lab coats, bed mats
  • Garbage bags ; packaging l3 ⁇ 4; other industrial and consumer use (tents, conveyor belts, hoses, ropes, hoods, canvas, curing sheets, vegetation nets; mats; non-woven fabrics, business nets, fishing nets, enferencing, Nori net, fishing line, bird net, insect net, insect net, animal net, filter cloth, dry canvas for paper machine, sweat sweater for helmet, attachment brush for vacuum cleaner, mop, stuffed toy, polishing brush, sewing thread, mosquito net, towel, cards It can be used as an antibacterial agent or deodorant for disposable tableware, stationery, household goods, etc.).
  • the chitin after contact treatment is used for materials such as agricultural film, agricultural simple covering material, cold gauze, binding tape, weed prevention bag, weed prevention net, planting net, P root sheet, nursery bed and pot. It can be used as a raw material for imparting antibacterial properties.
  • the chitin after the contact treatment is also used as a raw material for food. For example, it can be used as a raw material for snacks, jellies, gums, candies, tablets, hard and soft capsules, etc., and can provide anti-bacterial effects on intestinal control, prevent infectious diseases, and remove bad breath.
  • the unit (V / V) shown in the examples represents (capacity / capacity), and (W / W) represents (weight / weight).
  • the solids weight of the extract and the treatment liquid in the examples can be determined by weighing the entire amount of each liquid under reduced pressure and drying, or after accurately measuring the total amount, (Usually 5 mL) was concentrated under reduced pressure, weighed, and converted to the total volume.
  • a part (5 mL) of the extract A was concentrated under reduced pressure, and the weight of the obtained extract powder A was measured.
  • Extracted powder A weighed 26 mg and extract A contained 6.3 g of solids.
  • the extract A was allowed to cool to 25 ° C. and passed through a column filled with 15 g of chitin resin (manufactured by Nacalai Tester Co., Ltd.). Next, the column was washed with 20 OmL of purified water, and the flow-through solution and the washing solution were combined to obtain 1.4 L of a treatment solution B containing proanthain. Further, a part of the processing liquid B was concentrated under reduced pressure, and the weight of the obtained processing powder B was measured.
  • the weight of the treated powder B was 10.4 mg, and the treated liquid B contained 2.9 g of solids.
  • the component adsorbed on the chitin resin was eluted from the column using 20-OmL of a 60-80% (V / V) mixed solvent of water and ethanol to obtain eluate C of 20 OmL.
  • the eluate C was concentrated under reduced pressure, and the weight of the obtained powder C was measured.
  • the weight of powder C was 2.2 g.
  • Treatment solution B containing proanthocyanin is passed through a column filled with 50 g of an aromatic synthetic resin (Diaion HP-20: manufactured by Mitsubishi Chemical Corporation), and the proanthocyanin is adsorbed on the column. Was. This column was washed with 20 OmL of purified water, and combined with the flow-through solution to obtain 1.6 L of synthetic resin-based adsorbent flow-through solution D.
  • the column was eluted with a gradient of 20 to 100% (V / V) ethanol / water mixture, and fractions of 1 OmL each were collected.
  • V / V ethanol / water mixture
  • fractions of 1 OmL each were collected.
  • the OPC in each eluted fraction was detected by silica gel thin layer chromatography (TLC).
  • the TLC development conditions and detection method are as follows.
  • TLC Silica gel plate (Merck & CO., Inc.)
  • the fraction eluted with a 20-40% (V / V) ethanol-water mixed solvent contained OPC, and these fractions were combined to obtain 400 mL of a purified solution E.
  • this purified liquid E was concentrated under reduced pressure.
  • the weight of the obtained OPC purified powder E was 1.6 g.
  • the OPC content in the purified powder E was measured by the method of RSThompson et al. (J. Chem. Soc. Perkin Trans 1., 1387-1399, 1972). More than 80% (W / W).
  • the synthetic resin-based adsorbent passing solution D was concentrated under reduced pressure, and the weight of the obtained powder D was measured.
  • the weight of the powder D was 0.25 mg, and the synthetic resin-based adsorbent passage liquid D contained 0.8 g of solids.
  • the fractions eluted with 40 to 100% (V V) of a mixed solvent of ethanol and water were combined and concentrated under reduced pressure to obtain Powder F.
  • Table 1 shows the yield in each step of producing the proanthocyanidin-containing product.
  • the OPC content was calculated as follows. First, since the purified powder E contains O PC 80 wt% or more, solids weight to total O PC weight in purified powder E was assumed to 80 weight 0/0 (1. 6 g) (1. 28 g ). In the purification process, the OPC content was calculated assuming that all OPCs were contained in each solid content colored by anisaldehyde sulfuric acid. The solid content that did not develop color was set to 0.0%.
  • the proanthocyanidin-containing substance that does not adsorb to chitin is obtained by the chitin treatment, and by treating this substance with a synthetic resin-based adsorbent to adsorb the anthocyanidin, the impurities are reduced. It can be seen that a high-purity bronthocyanidin-containing material removed can be obtained. Furthermore, it can be seen that the solid content of the proanthocyanidin-containing material contained in the fraction not adsorbed by chitins contains OPC of 40% or more.
  • Example 2 the chitin resin after the contact treatment was concentrated under reduced pressure to obtain 17 g of powder J. Using the obtained powder J, antibacterial activity was measured by a shake flask method. As a comparison, the antibacterial activity of chitin resin powder K without contact treatment was also measured.
  • the measuring method is as follows.
  • Staphylococcus aureus was used as a test bacterium. This test strain was transplanted to Brain 'Heart' infusion agar slant medium and cultured at 37 ° C for 24 hours. This culture was inoculated into a normal broth medium using a platinum loop, cultured at 37 ° C for 6 to 10 hours, and the number of bacteria was adjusted to 1.5 to 3 ⁇ 10 8 cells / mL using a normal broth medium. Further, this bacterial solution was diluted 1000 times with a stock solution of a phosphate buffer to obtain an inoculated bacterial solution.
  • An antibacterial test was performed using the shake culture solution and the inoculated bacterial solution prepared as described above. Prepare six Erlenmeyer flasks with screw caps with 20 OmL caps. A shaking culture solution (70 mL) was added to each, and the cap was loosely closed, followed by sterilization with an autoclave. After cooling, the inoculum (5 mL) was added and mixed well. Finally, the number of bacteria in the Erlenmeyer flask was adjusted to 1-2 ⁇ 10 4 ZmL. Bacterial liquid (1 mL) was collected from any three of the triangular flasks, a 10-fold dilution series was prepared with the test solution, and pour agar plates were prepared using a standard agar medium.
  • the plate was incubated at 37 ° C for 24-48 hours.
  • the number of grown coloeae was measured, and the number of viable bacteria (initial bacterial count) was calculated by multiplying by the dilution ratio.
  • the average value of the viable cell count was designated as A.
  • the sterilization rate was calculated from the obtained values A and B as ⁇ (AB) / A ⁇ XI00, the sterilization rate of powder K was 93%, whereas the sterilization rate of powder J was 29%. %Met. From the above, it can be seen that the chitin resin after the contact treatment has high antibacterial activity.
  • a proanthocyanin-containing substance containing a high ratio of OPC having high physiological activity can be effectively obtained.
  • a proanthocyanidin-containing substance having a higher OPC content can be provided by employing a method including a step of treating with a synthetic resin-based adsorbent. Bronthocyanidin having a high OPC content is effective in improving vascular enhancement, hypertension, and chilliness, and is used as a raw material for producing foods, cosmetics, and pharmaceuticals.

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Abstract

L'invention concerne une matière riche en proanthocyanidine contenant une grande quantité d'OPC très actif au plan physiologique, et pouvant être produite efficacement par l'extraction de proanthocyanidine d'une plante, par mise en contact de l'extrait obtenu avec de la chitine, du chitosane ou des dérivés de ceux-ci et par la récupération des matières non absorbées. Par ailleurs, un matériau riche en proanthocyanidine possédant une teneur élevée en OPC peut être produite par le traitement de la proanthocyanidine avec un adsorbant du type résine synthétique.
PCT/JP2002/005879 2002-04-24 2002-06-12 Procede de production de matiere riche en proanthocyanidine WO2003090770A1 (fr)

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AU2002311198A AU2002311198A1 (en) 2002-04-24 2002-06-12 Process for producing proanthocyanidine-rich material
JP2003587403A JP3595816B2 (ja) 2002-04-24 2002-06-12 プロアントシアニジン含有物の製造方法

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006112496A1 (fr) * 2005-04-15 2006-10-26 Toyo Shinyaku Co., Ltd. Procede de production de materiau contenant de la proanthocyanidine
JP2007518812A (ja) * 2004-01-23 2007-07-12 フェノーリックス、エルエルシー フェノール化合物に富む組成物及びその製造方法
JP4977024B2 (ja) * 2005-04-15 2012-07-18 株式会社東洋新薬 プロアントシアニジン含有物の製造方法

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Publication number Priority date Publication date Assignee Title
WO2005033053A1 (fr) * 2003-10-01 2005-04-14 Toyo Shinyaku Co., Ltd. Procede de production d'un produit a teneur elevee en proanthocyanidine
WO2006061915A1 (fr) * 2004-12-09 2006-06-15 Toyo Shinyaku Co., Ltd. Préparation curative pour la peau
RU2435579C2 (ru) 2005-02-25 2011-12-10 Нагасаки Юниверсити Способ получения проантоцианидинового олигомера
US9114114B2 (en) 2007-06-21 2015-08-25 Mars, Inc. Edible products having a high cocoa polyphenol content and improved flavor and the milled cocoa extracts used therein
CN102802652B (zh) 2009-05-26 2014-09-10 株式会社爱茉莉太平洋 用于促进血液循环和增强血管健康的包含豆类提取物的组合物
US8642088B2 (en) 2009-09-04 2014-02-04 Wisconsin Alumni Research Foundation Tannin-chitosan composites
WO2014065369A1 (fr) * 2012-10-25 2014-05-01 日本製紙株式会社 Extrait de feuille de thé
US12234578B2 (en) 2020-01-29 2025-02-25 Wisconsin Alumni Research Foundation Tannin composite fibers

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2007518812A (ja) * 2004-01-23 2007-07-12 フェノーリックス、エルエルシー フェノール化合物に富む組成物及びその製造方法
WO2006112496A1 (fr) * 2005-04-15 2006-10-26 Toyo Shinyaku Co., Ltd. Procede de production de materiau contenant de la proanthocyanidine
US7863466B2 (en) 2005-04-15 2011-01-04 Toyo Shinyaku Co., Ltd. Method of producing proanthocyanidin-containing material
JP4977024B2 (ja) * 2005-04-15 2012-07-18 株式会社東洋新薬 プロアントシアニジン含有物の製造方法

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AU2002311198A1 (en) 2003-11-10
JPWO2003091237A1 (ja) 2005-09-02
WO2003091237A1 (fr) 2003-11-06
JP3595816B2 (ja) 2004-12-02
JPWO2003090770A1 (ja) 2005-08-25

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