WO2007136068A1 - ポリフェノール高含有組成物の製造方法 - Google Patents
ポリフェノール高含有組成物の製造方法 Download PDFInfo
- Publication number
- WO2007136068A1 WO2007136068A1 PCT/JP2007/060455 JP2007060455W WO2007136068A1 WO 2007136068 A1 WO2007136068 A1 WO 2007136068A1 JP 2007060455 W JP2007060455 W JP 2007060455W WO 2007136068 A1 WO2007136068 A1 WO 2007136068A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- polyphenol
- quercetin
- polysaccharide
- solvent
- cellulose
- Prior art date
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Classifications
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- 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
- A61K31/353—3,4-Dihydrobenzopyrans, e.g. chroman, catechin
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
- A23L29/20—Foods or foodstuffs containing additives; Preparation or treatment thereof containing gelling or thickening agents
- A23L29/206—Foods or foodstuffs containing additives; Preparation or treatment thereof containing gelling or thickening agents of vegetable origin
- A23L29/212—Starch; Modified starch; Starch derivatives, e.g. esters or ethers
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
- A23L29/20—Foods or foodstuffs containing additives; Preparation or treatment thereof containing gelling or thickening agents
- A23L29/206—Foods or foodstuffs containing additives; Preparation or treatment thereof containing gelling or thickening agents of vegetable origin
- A23L29/262—Cellulose; Derivatives thereof, e.g. ethers
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
- A23L33/105—Plant extracts, their artificial duplicates or their derivatives
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- 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
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
- A61K31/197—Carboxylic acids, e.g. valproic acid having an amino group the amino and the carboxyl groups being attached to the same acyclic carbon chain, e.g. gamma-aminobutyric acid [GABA], beta-alanine, epsilon-aminocaproic acid or pantothenic acid
- A61K31/198—Alpha-amino acids, e.g. alanine or edetic acid [EDTA]
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- 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
- A61K31/716—Glucans
- A61K31/717—Celluloses
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- 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
- A61K31/716—Glucans
- A61K31/718—Starch or degraded starch, e.g. amylose, amylopectin
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- A—HUMAN NECESSITIES
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- 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
- A61K31/716—Glucans
- A61K31/722—Chitin, chitosan
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- 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
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08H—DERIVATIVES OF NATURAL MACROMOLECULAR COMPOUNDS
- C08H6/00—Macromolecular compounds derived from lignin, e.g. tannins, humic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L1/00—Compositions of cellulose, modified cellulose or cellulose derivatives
- C08L1/02—Cellulose; Modified cellulose
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L3/00—Compositions of starch, amylose or amylopectin or of their derivatives or degradation products
- C08L3/02—Starch; Degradation products thereof, e.g. dextrin
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L5/00—Compositions of polysaccharides or of their derivatives not provided for in groups C08L1/00 or C08L3/00
- C08L5/08—Chitin; Chondroitin sulfate; Hyaluronic acid; Derivatives thereof
Definitions
- the present invention relates to a method for producing a polyphenol-rich composition, a method for purifying polyphenol, and in particular to a composition for suppressing blood pressure elevation obtained by adding arginine to quercetin, which is a polyphenol.
- Polyphenol is a generic name for compounds having two or more phenolic hydroxyl groups in the same molecule, and many types are widely distributed in the plant kingdom.
- Many flavonoids which are representative polyphenols, have many bioregulatory functions such as antioxidant, antimutagenic, anticancer, antihypertensive, antidiabetic and antiallergic.
- quercetin a kind of flavonoid, has been reported to show an excellent antihypertensive effect.
- the excellent action of polyphenols has been attracting attention, and the demand is wide ranging from foods, cosmetics and pharmaceuticals.
- Patent Document 1 a method in which a polyphenol-containing liquid is brought into contact with a styrene synthetic adsorbent to adsorb and separate polyphenols (Patent Document 1), an onion hull extract and protein are mixed, and polyphenol is mixed.
- Patent Document 2 a method in which a compound-containing solution and wood flour are brought into contact, polyphenol is adsorbed onto the wood flour, and dissolved in a solvent.
- Patent Document 3 a method of forming a complex of flavonoid quercetin and protein and releasing it.
- Patent Document 1 Japanese Patent Laid-Open No. 2002-335911
- Patent Document 2 Japanese Patent Laid-Open No. 7-238087
- Patent Document 3 Japanese Patent Laid-Open No. 2005-289850
- Patent Documents 1 and 2 attention has not been paid to the use of adsorbents that adsorb polyphenols.
- these conventional adsorption purification methods do not consider using an edible substance as an adsorbent and using an adsorbent adsorbed with polyphenol as a food material containing a high amount of polyphenol.
- Patent Document 3 in which protein, which is an edible substance, is used as an adsorbent, there is a risk of adsorbing residual pesticides in addition to polyphenol when adsorbing polyphenol to protein. The problem remained.
- the present invention has been made in view of the above circumstances, and an object thereof is to provide a safe and simple method for producing a polyphenol-containing composition and a method for purifying polyphenol. Means for solving the problem
- the present invention has found that the polyphenol-supporting polysaccharide strength polyphenol can be purified, and that a composition containing quercetin, which is a kind of polyphenol, and arginine has an excellent antihypertensive effect, The present invention has been completed.
- a polyphenol-containing solution is brought into contact with a polysaccharide having a selected group strength including cellulose, starch, chitin, and chitosan force, and then the polysaccharide is added to the polysaccharide. It is characterized by carrying phenol.
- the cellulose is crystalline cellulose, carboxymethyl cellulose, fine fibrous cellulose, powdered cellulose. It is preferable that
- the polyphenol to be highly concentrated is quercetin.
- the polyphenol-containing solution is preferably a quercetin-containing solution obtained by extracting an onion shell with water or an aqueous solution of 40% or less ethanol, methanol, or acetone. It is.
- the present invention provides a food or drink characterized by containing a polyphenol-supporting polysaccharide.
- the polyphenol-supporting polysaccharide is starch.
- the present invention provides a method for purifying a phenol, which comprises contacting a polyphenol-supported polysaccharide with a solvent to elute the polyphenol into the solvent, and powdering the polyphenol after removing the solvent.
- the polyphenol to be purified is quercetin.
- the present invention also provides a composition for suppressing an increase in blood pressure, which contains quercetin and arginine.
- polyphenols can be easily and safely purified from plant materials containing polyphenols.
- polyphenol can be added to food and drink as a food material together with the adsorbent, a high concentration of polyphenol can be ingested efficiently.
- quercetin is applied as the polyphenol, it is possible to obtain an excellent antihypertensive composition by adding arginine.
- FIG. 1 is a view showing a flowchart of a manufacturing example of the present invention.
- FIG. 2 shows changes in blood pressure of SHR rats in Example 2.
- FIG. 3 shows changes in blood pressure of WKY rats in Example 2.
- Polyphenols that can be applied to the present invention are not limited, but include, for example, phenylcarboxylic acids, lignans, curcumins, coumarins, flavonoids, and the like. Polyphenols classified as flavonoids are particularly preferred. Better ,.
- Flavonoid polyphenols include flavones such as apigenin, chrysin and luteolin; flavonols such as galangin, quercetin, rutin, kaempferol and myricetin; isoflavones such as daidzein, daidzin and genistein; catechin, epicatechin, epigallocatechin and epicatechin Flavanols such as gallate, epigallocatechin gallate, and theaflavin; flavanones such as naringen, naringin, hesperetin, hesperidin; anthocyanins, anthocyanins, cyanidins, cyanans, proanthocyanidins, proanthocyanins, delphidin, delphi Examples thereof include anthocyanins such as nin, pelargosine, and pelargonine, and glycosides thereof.
- the polyphenol-containing solution in the present invention is an extract of a material containing polyphenol such as a plant, as long as it is a solution containing at least one polyphenol, and a process of processing the material containing polyphenol.
- Etc. such as residue, such as juice, mixed liquid, boiled juice and squeezed rice cake. Since the type and content of polyphenols differ depending on the material, the material to be used may be appropriately selected according to the polyphenol to be demanded. In the present invention, it is particularly preferable to use a quercetin-containing solution from which onion hull strength has also been extracted.
- the extraction method is not particularly limited and may be in accordance with generally applied extraction means.
- extraction solvent is water, ethanol
- the polysaccharide supporting polyphenol cellulose, denpun, chitin, and chitosan are preferable.
- cellulose crystalline cellulose, carboxymethyl cellulose, fine fibrous cellulose, and powdered cellulose are particularly preferable.
- the polyphenol loading step is carried out by bringing the polyphenol-containing solution into contact with the polysaccharide and selectively loading polyphenol onto the polysaccharide.
- the solvent in the polyphenol loading step is preferably water or 40% or less ethanol, methanol, and acetone aqueous solution. If the concentration of the organic solvent exceeds 40%, the amount of polyphenol supported on the polysaccharide decreases, which is not preferable.
- the polysaccharide carrying polyphenol can be added to a food or drink as a polyphenol carrying polysaccharide if the solvent is removed by drying, decompression or the like. It can also be taken as food.
- a polyphenol-supported polysaccharide it is more preferable to use a digestible polysaccharide as the supported polysaccharide in consideration of the absorption efficiency of the supported polyphenol.
- Foods and drinks to which the polyphenol-supported polysaccharide of the present invention is added include confectionery, potatoes, dairy products, processed marine products, processed livestock products, processed vegetables, fruit products, fermented foods, seasonings, miso soup, soup General foods such as foods, beverages, health foods, dietary supplements, other oral preparations such as gums, candy, tablets, and instant foods.
- any food or drink can be produced by a conventional method.
- the polyphenol-supporting polysaccharide can be purified by contacting the solvent with a solvent to elute the polyphenol supported on the polysaccharide into the solvent.
- Solvents used for elution of polyphenol include water, ethanol, propylene glycol , 1,3-butylene glycol, methanol, hexane, acetone, jetyl ether, dioxane, ethyl acetate and the like can be used alone or in combination.
- water, ethanol, methanol, and acetone are preferable, and a 40 to 80% ethanol aqueous solution is more preferable.
- the polysaccharide is removed by filtration, and further the solvent is removed by concentration, whereby a purified polyphenol can be obtained as a residue.
- the purified polyphenol can be dried and powdered by a method such as freeze drying or spray drying.
- the polyphenol purified by the present invention can be applied to uses in which polyphenol is usually used, such as foods, cosmetics, and pharmaceuticals.
- composition containing quercetin which is a kind of polyphenol, and arginine exhibits an excellent antihypertensive action.
- quercetin has an action of suppressing an increase in blood pressure, and that the action is remarkably enhanced by the addition of arginine, which is a known amino acid.
- Quercetin is sufficient to suppress blood pressure rise when ingested 0.7 mgZdayZkg or more, and it is added so that the mixing ratio of quercetin and arginine is 10 to 2 3: 1 in consideration of both side effects of effect and dose. Is preferred.
- the purified quercetin used in the composition for suppressing blood pressure elevation of the present invention is preferably purified, but may be in the form of a quercetin-containing material as long as it contains an effective amount. That is, in the case of describing in accordance with the method of the present invention, a quercetin-containing solution before contact with a polysaccharide, a quercetin-supported polysaccharide obtained by contacting the solution with a polysaccharide, a quercetin-supported polysaccharide, and the like. Purified quercetin or the like, or a composition containing these may be applicable. Similarly, arginine can be used in a purified state or content, and it may be obtained by a conventional purification method or a commercially available product.
- the antihypertensive composition of the present invention containing the quercetin and arginine can be blended in foods, pharmaceuticals, cosmetics and the like, and the components and additives that are usually used for these can be used in combination. Yo ⁇ . There is no specific rule regarding the amount of the composition.
- FIG. 1 is a chart showing the process until the onion hull strength is purified by the method of the present invention, quercetin, which is a kind of polyphenol, and arginine is added to the quercetin to obtain the antihypertensive composition of the present invention. It is.
- Quercetin-supported crystalline cellulose was immersed in 10 L of 50% ethanol aqueous solution to elute quercetin.
- the purified quercetin solution obtained by concentrating and removing the solvent was powdered by freeze drying to obtain 2 g of quercetin powder.
- arginine powder was added to the quercetin powder to obtain a blood pressure increase-suppressing composition of the present invention.
- Table 1 shows the quercetin carrying ratio of each polysaccharide (the amount of quercetin carried on the polysaccharide relative to the amount of quercetin extracted). Quercetin is quantified by liquid chromatography.
- An extraction sample of 4 ml of each solvent, 3 ml of methanol, 3 ml of 2 mM jetyldithiocarbamate Z methanol solution and 2.5 ml of 50% hydrochloric acid were prepared in a heating block test tube and heated at 90 ° C. for 2 hours. After heating, 1 ml of the prepared sample was collected, added with 2.5 ml of water, filtered through a PTFE filter of 0.45 / z m pore size, and subjected to liquid chromatography measurement.
- Polysaccharides which are polyphenol-supporting substances of the present invention, all show high polyphenol-supporting ability. Particularly, crystalline cellulose and carboxymethylcellulose have a remarkably excellent quercetin-supporting rate. Further, in the present invention, it is possible to ingest polyphenols together with polysaccharides carrying polyphenols, and therefore it is clear that polyphenols-supported polysaccharides are superior to conventional adsorbents in terms of polyphenol ingestion efficiency. It is.
- digestible polysaccharides such as potato starch, corn starch and tapio starch are digested and absorbed in the body, so the absorption efficiency of polyphenol loaded on the polysaccharide is supported on non-digestible polysaccharide. It will be higher than the case. Therefore, digestible polysaccharides are particularly preferred as polyphenol-supporting polysaccharides added to foods.
- the solvent for supporting quercetin on crystalline cellulose was examined. After the quercetin-containing solution was obtained using various concentrations of ethanol, methanol and acetone in place of water as the extraction solvent in the above production example, crystalline cellulose was added, and the subsequent operations were in accordance with the production example. The evaluation of the solvent was performed based on the loading rate of quercetin supported on crystalline cellulose (the amount supported on crystalline cellulose relative to the amount of quercetin extracted). The amount of polyphenol is measured by liquid chromatography as described above.
- Table 2 shows the quercetin loading for each solvent concentration.
- quercetin extraction solvent from various concentrations of ethanol, methanol, and acetone was examined by replacing quercetin extraction solvent from onion skin with water. Quercetin is quantified by liquid chromatography as described above.
- Table 3 shows the amount of quercetin extracted according to each solvent and its concentration.
- Quercetin was almost stably extracted at each concentration of ethanol, methanol, and acetone, and in particular, 3080% ethanol aqueous solution was excellent in extraction amount. When water was used, sufficient quercetin extraction was observed.
- a solvent for extracting a larger amount of polyphenol than a polyphenol-containing material 3080% ethanol aqueous solution is suitable.
- the solvent concentration in the above-described polyphenol loading considering that the preferred solvent for polyphenol loading was water or ethanol, methanol, or an aqueous acetone solution having a concentration of 40% or less.
- the solvent for polyphenol loading was water or ethanol, methanol, or an aqueous acetone solution having a concentration of 40% or less.
- quercetin-supporting crystalline cellulose strength quercetin was eluted using water or ethanol of various concentrations, methanol, or acetone in place of 50% ethanol as the elution solvent in the above production example.
- the solvent was evaluated by the elution rate (the amount of elution into the solvent with respect to the amount of quercetin supported).
- the quantification of quercetin Similarly, by liquid chromatography.
- Table 4 shows the elution rate of quercetin for each solvent concentration.
- the polyphenol-containing material of each material was purified as tea, grape juice lees, and red bean broth instead of the onion skin.
- Table 5 shows the polyphenol recovery from each material (the amount of purified polyphenol relative to the amount of polyphenol in the polyphenol-containing solution).
- the red bean broth is a solution of boiled red bean lOOg in 400 ml of water in a polyphenol-containing solution.
- lg is extracted with 100 ml of hot water
- grape juice is 10 g in hot water. Extracted with 100 ml to obtain a polyphenol-containing solution. Subsequent operations were in accordance with the above production example.
- quercetin is particularly suitable as the polyphenol applied to the present invention.
- the recovery rate of quercetin when lignocellose was used as the polysaccharide supporting polyphenol was investigated and compared with the recovery rate of quercetin by crystalline cellulose in the above test.
- the polyphenol-containing solution was prepared by extracting onion skin lg with 100 ml of hot water in the same manner as in the above test, and other operations were in accordance with the above production example.
- Polyphenol (quercetin) recovery rate by each cellulose (containing polyphenol) Table 6 shows the amount of purified polyphenol relative to the amount of polyphenol in the solution. Quercetin was quantified by liquid chromatography, and lignocellulose prepared by the following method was used.
- lignocellulose was inferior to quercetin in supporting ability compared to crystalline cellulose.
- crystalline cellulose is particularly superior to lignocellulose in carrying quercetin.
- Lignocellulose is a cellulose containing lignin, a polymer present in xylem, and V, a loose wood flour.
- Crystalline cellulose is a refined product of pure cellulose, which is crystalline, and does not contain lignin.
- the blood pressure increase inhibitory effect was examined on the blood pressure increase inhibitory composition of the present invention obtained by adding arginine to quercetin.
- Quercetin adjustment Onion lOOg washed with 10 L of water heated to 80 ° C. was added to extract quercetin, and impurities were removed to obtain a quercetin-containing solution.
- the quercetin content in the quercetin-containing liquid was 0.1 mgZml.
- the quercetin-containing solution was appropriately concentrated with an evaporator.
- the quercetin-containing solution obtained by the above preparation method and a commercially available arginine powder (Ajinomoto Co., Inc.) were mixed so that the contents of quercetin and arginine were as shown in Table 7 below. Orally administered twice, and raised for 8 weeks in the same environment as the preliminary breeding. Feed and water were available ad libitum during the test period.
- Rat blood pressure was measured once a week. After each rat was warmed in a 38 ° C warmer for several minutes and acclimated, the rat's tail pulse wave was measured using a non-invasive blood pressure automatic measuring device (BP-98A; manufactured by Softron Co., Ltd.). The systolic blood pressure was measured. The blood pressure of each rat was recorded as the average of the values measured three times each time. Figure 2 shows changes in blood pressure in each group.
- BP-98A non-invasive blood pressure automatic measuring device
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US12/301,066 US20090197942A1 (en) | 2006-05-23 | 2007-05-22 | Method For Producing Polyphenol-Rich Composition |
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Cited By (7)
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JP2010037258A (ja) * | 2008-08-04 | 2010-02-18 | Toyo Suisan Kaisha Ltd | ポリフェノールの吸収促進剤 |
JP2013237752A (ja) * | 2012-05-14 | 2013-11-28 | Nippon Carbide Ind Co Inc | 包接複合体含有組成物、並びに、包接複合体およびその製造方法 |
JP2016013075A (ja) * | 2014-07-01 | 2016-01-28 | イビデン株式会社 | ケルセチン含有抽出物 |
JP2016029945A (ja) * | 2014-07-30 | 2016-03-07 | ユーハ味覚糖株式会社 | ポリフェノール含有ノンシュガーハードキャンディ及びその製造方法 |
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KR101186416B1 (ko) * | 2010-02-09 | 2012-09-27 | 강원대학교산학협력단 | 케르세틴 함량이 증진된 양파 및 그 제조 방법 |
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- 2007-05-22 US US12/301,066 patent/US20090197942A1/en not_active Abandoned
- 2007-05-22 JP JP2007547674A patent/JP4347899B2/ja active Active
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JPH06311847A (ja) * | 1993-04-28 | 1994-11-08 | J A Foods Ooita:Kk | 清澄緑茶飲料の製造方法 |
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Cited By (9)
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JP2010037258A (ja) * | 2008-08-04 | 2010-02-18 | Toyo Suisan Kaisha Ltd | ポリフェノールの吸収促進剤 |
JP2013237752A (ja) * | 2012-05-14 | 2013-11-28 | Nippon Carbide Ind Co Inc | 包接複合体含有組成物、並びに、包接複合体およびその製造方法 |
JP2016013075A (ja) * | 2014-07-01 | 2016-01-28 | イビデン株式会社 | ケルセチン含有抽出物 |
JP2016029945A (ja) * | 2014-07-30 | 2016-03-07 | ユーハ味覚糖株式会社 | ポリフェノール含有ノンシュガーハードキャンディ及びその製造方法 |
CN107522790A (zh) * | 2017-09-22 | 2017-12-29 | 西南大学 | 一种双功能新型变性淀粉及其制备方法 |
CN109529784A (zh) * | 2018-11-16 | 2019-03-29 | 天津科技大学 | 多酚等梯度吸附纳米复合物及其制备方法 |
CN109529784B (zh) * | 2018-11-16 | 2021-11-09 | 天津科技大学 | 多酚等梯度吸附纳米复合物及其制备方法 |
JP7123434B1 (ja) | 2021-03-17 | 2022-08-23 | 株式会社アイビー化粧品 | 破骨細胞分化抑制剤 |
JP2022143322A (ja) * | 2021-03-17 | 2022-10-03 | 株式会社アイビー化粧品 | 破骨細胞分化抑制剤 |
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