WO2013176206A1 - Procédé de fabrication d'une composition de polyphénol - Google Patents

Procédé de fabrication d'une composition de polyphénol Download PDF

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WO2013176206A1
WO2013176206A1 PCT/JP2013/064309 JP2013064309W WO2013176206A1 WO 2013176206 A1 WO2013176206 A1 WO 2013176206A1 JP 2013064309 W JP2013064309 W JP 2013064309W WO 2013176206 A1 WO2013176206 A1 WO 2013176206A1
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water
ethanol
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山田　泰司
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花王株式会社
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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
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2200/00—Function of food ingredients

Definitions

  • the present invention relates to a method for producing a polyphenol composition having excellent solubility in water.
  • polyphenols are known to have an antioxidant power and are expected to have effects such as anti-arteriosclerosis, anti-allergy and blood flow enhancement, and thus are recognized as important ingredients in health foods.
  • polyphenols have poor water solubility, and it is difficult to use them for aqueous foods such as soft drinks.
  • Patent Document 1 a method in which hesperidin glycoside is added to citrus fruit juice and juice drink and then heated to dissolve the contained flavonoid compound.
  • Patent Document 2 A method in which a poorly water-soluble flavoid and ⁇ -cyclodextrin are heat-treated so that the poorly water-soluble flavonoid is included in ⁇ -cyclodextrin, and then ⁇ -glucosyl hesperidin is allowed to coexist (Patent Document 2); A method of solubilizing flavonoids by coexistence of poorly soluble flavonoids with soybean saponin and / or malonylisoflavone glycoside (Patent Document 3); poorly water-soluble polyphenols and catechins in the presence of an aqueous medium , One or more selected from methylated products of chlorogenic acids and poorly water-soluble polyphenols Method for producing a polyphenol composition (Patent Document 4) have been proposed to heat treatment at 100 ⁇ 180 ° C..
  • the present invention comprises (A) a poorly water-soluble polyphenol and (B) one or more selected from methylated products of catechins, chlorogenic acids and poorly water-soluble polyphenols at 0 ° C. or higher and 90 ° C. or lower,
  • the present invention provides a method for producing a polyphenol composition comprising a step of obtaining a solution by dissolving in an ethanol aqueous solution having an ethanol concentration of 30% by volume to 90% by volume and a step of drying the obtained solution.
  • hesperidin glycosides such as ⁇ -glucosyl hesperidin as a solubilizer
  • solubilizers such as malonyl isoflavone glycosides can increase the solubility of poorly water-soluble polyphenols, but the use of solubilizers is limited due to the unique grain odor derived from soybeans. The problem of being done is considered.
  • the method of heat treatment at 100 to 180 ° C. in the presence of an aqueous medium has a problem that a pressure vessel is required. Therefore, the present invention relates to providing a method for producing a polyphenol composition having excellent solubility in water using a material that does not require special equipment, is inexpensive, and has little influence on the flavor of the composition. .
  • the present inventors have made various studies on the solubilization techniques for poorly water-soluble polyphenols.
  • the poorly water-soluble polyphenols and the methylated product of catechins, chlorogenic acids, or poorly water-soluble polyphenols are at least 0 ° C. and 90 ° C. If dissolved in an aqueous ethanol solution having an ethanol concentration of 30% by volume or more and 90% by volume or less under the following temperature conditions, and the resulting solution is dried, the dissolved concentration of the hardly water-soluble polyphenols can be dramatically increased.
  • the powdery composition that has undergone such a treatment maintains high solubility when it is re-dissolved in water and precipitation of poorly water-soluble polyphenols is suppressed even at room temperature.
  • the influence on the flavor of the composition by the methylated product of ethanol, catechins, chlorogenic acids, or poorly water-soluble polyphenols was little.
  • a polyphenol composition having excellent solubility in water can be provided at low cost without using a special device.
  • the polyphenol composition of the present invention is useful for various foods and beverages and pharmaceuticals because it has little influence on the flavor of the solubilizer.
  • a poorly water-soluble polyphenol and (B) one or more selected from methylated products of catechins, chlorogenic acids and poorly water-soluble polyphenols, It includes a step of obtaining a solution by dissolving in an ethanol aqueous solution having an ethanol concentration of 30% by volume to 90% by volume at 0 ° C. to 90 ° C., and a step of drying the obtained solution.
  • component (B) one kind or two or more kinds selected from methylated products of catechins, chlorogenic acids and poorly water-soluble polyphenols.
  • “poorly water-soluble polyphenols” refers to those having a log P value of ⁇ 1.0 or more and 4.0 or less.
  • the poorly water-soluble polyphenols preferably have a log P value of ⁇ 0.5 or more and 3.5 or less.
  • the log P value is a value obtained by taking the common logarithm of the distribution coefficient between 1-octanol / water and is an index indicating the hydrophobicity of an organic compound. The larger the value, the higher the hydrophobicity.
  • the log P value of polyphenols can be measured by a flask shaking method described in Japanese Industrial Standard Z7260-107. Details are described in the examples. Further, it is preferably applied to those having a solubility in water at 25 ° C. of 5 g / L or less, more preferably 2 g / L or less, further 1 g / L or less, further 0.5 g / L or less, and further 0.1 g. / L or less is preferable.
  • phenolic substances in which one or more, and more than two, hydroxyl groups are bonded to the benzene ring can be preferably applied.
  • plant-derived flavonoids, tannins, phenolic acids and the like can be mentioned.
  • the poorly water-soluble polyphenols that can be more preferably applied include flavonols, flavanones, flavones, isoflavones, phenol carboxylic acids, anthocyanidins, hydroxycinnamic acid derivatives, ellagic acid and the like.
  • the poorly water-soluble polyphenols may be one kind or a mixture of two or more kinds.
  • component (B) one selected from catechins, chlorogenic acids and methylated products of poorly water-soluble polyphenols may be used, or two or more may be used in combination.
  • the catechins used in the present invention include non-epimeric catechins such as catechin, gallocatechin, catechin gallate and gallocatechin gallate, and epi-catechins such as epicatechin, epigallocatechin, epicatechin gallate and epigallocatechin gallate. It is a collective term.
  • the content of catechins is defined based on the total amount of the above eight types.
  • tea extracts may be used.
  • the tea extract at least one selected from a tea extract, a concentrate thereof, and a purified product thereof can be used.
  • the “tea extract” refers to an extract extracted from tea leaves using hot water or a water-soluble organic solvent, and has not been concentrated or purified.
  • a water-soluble organic solvent for example, a lower alcohol such as ethanol can be used.
  • the extraction method known methods such as kneader extraction, stirring extraction (batch extraction), countercurrent extraction (drip extraction), and column extraction can be employed.
  • the tea leaves used for extraction can be roughly classified into non-fermented tea, semi-fermented tea, and fermented tea depending on the processing method.
  • non-fermented tea examples include green tea such as sencha, sayha, gyokuro, mochi tea, kettle tea, stem tea, stick tea, and bud tea.
  • semi-fermented tea examples include oolong tea such as iron kannon, color type, golden katsura, and martial arts tea.
  • fermented tea examples include black teas such as Darjeeling, Assam, Sri Lanka and the like. These can be used alone or in combination of two or more. Among these, green tea is preferable from the viewpoint of the content of catechins.
  • the “tea extract concentrate” refers to removing a part of the water content of a solution extracted from hot leaves or a water-soluble organic solvent from tea leaves selected from non-fermented tea, semi-fermented tea and fermented tea.
  • concentration of catechins is increased.
  • the form include various forms such as a solid, an aqueous solution, and a slurry.
  • the tea extract or the like can be purified by purification using a solvent or a column.
  • the chlorogenic acids used in the present invention include 3-caffeoylquinic acid, 4-caffeoylquinic acid and monocaffeoylquinic acid of 5-caffeoylquinic acid, 3-feruloylquinic acid and 4-feruloylquinic acid. And 5-feruloylquinic acid monoferuloylquinic acid and 3,4-dicaffeoylquinic acid, 3,5-dicaffeoylquinic acid and 4,5-dicaffeoylquinic acid dicaffeoylquinic acid Is a collective term.
  • the content of chlorogenic acids is defined based on the total amount of the above nine types.
  • chlorogenic acids may be in the form of a salt, such as a salt with an alkali metal such as sodium or potassium, a salt with an alkaline earth metal such as magnesium or calcium, monoethanolamine, diethanolamine, triethanolamine, etc.
  • salts with organic amines, salts with basic amino acids such as arginine, lysine, histidine, ornithine, and the like.
  • chlorogenic acids a plant extract containing the same, a concentrate thereof, a purified product thereof, or the like can be used.
  • plant extracts include, for example, sunflower seeds, apple immature fruits, fresh coffee beans, Simon leaves, pine cones, pine plant seed shells, sugarcane southern leaves, burdock, eggplant skin, Examples include those extracted from ume fruit, dandelion, and vines.
  • raw coffee bean extract is preferable from the viewpoint of chlorogenic acid content and the like.
  • the type of coffee tree may be any of Arabica, Robusta, Revelica and Arabsta.
  • the method and conditions for extraction, concentration and purification are not particularly limited, and known methods and conditions can be employed.
  • Commercially available chlorogenic acid-containing preparations may be used as chlorogenic acids, and examples include flavor holder RC (Hasegawa Fragrance Co., Ltd.).
  • the methylated product of poorly water-soluble polyphenols used in the present invention is a methylated product of the aforementioned poorly water-soluble polyphenols solubilized in water.
  • the position and number of methylation are not particularly limited. Specific examples include methyl hesperidin, methyl quercetin, methyl resveratrol, methyl rutin and the like, and methyl hesperidin is preferred.
  • Methyl hesperidin is known to mainly contain chalcone type compounds (A) and flavanone type compounds (B), and examples of the constituents include those having the structures shown below. *
  • R represents a hydrogen atom or a methyl group.
  • methyl hesperidin as a pharmaceutical additive and a food additive is mainly handled as a mixture of compounds (C) and (D).
  • Gl represents a glucose residue
  • Rh represents a rhamnose residue
  • Gl-2 represents the 2-position of the glucose residue (including C-3 in the case of C-1)
  • Rh-2 represents Represents the second position of the rhamnose residue.
  • hesperidin methyl chalcone as a cosmetic raw material is handled as a compound represented by (E).
  • a composition containing a large amount of chalcone type compound it is also called hesperidin methyl chalcone.
  • R represents a hydrogen atom or a methyl group.
  • the methyl hesperidin used in the present invention may include both the chalcone type compound (A) and the flavanone type compound (B) shown above, or may include only one of them.
  • more preferable methyl hesperidin includes a mixture of the compound (C) and the compound (D).
  • Methyl hesperidin is a known method, for example, hesperidin is dissolved in an aqueous sodium hydroxide solution, a corresponding amount of dimethyl sulfate is allowed to act on the alkaline solution, the reaction solution is neutralized with sulfuric acid, and extracted with n-butyl alcohol. It can be produced by distilling off and then recrystallizing with isopropyl alcohol (Sakibuka, Nippon Kagaku Kagaku, 79, 733-6 (1958)), but the production method is not limited to this.
  • methyl hesperidin-containing preparations may be used as methyl hesperidin, for example, “methyl hesperidin” (Tokyo Kasei Kogyo Co., Ltd.), “hesperidin methyl chalcone” (Sigma), “methyl hesperidin” (Hamari Pharmaceutical Co., Ltd.) Co., Ltd.).
  • the ethanol concentration is more preferably 32% by volume or more, further 35% by volume or more, further 40% by volume or more, from the viewpoint of preventing odor derived from the component (B) of the polyphenol composition obtained. Furthermore, 50 volume% or more, 60 volume% or more, and 70 volume% or more are preferable. The ethanol concentration is more preferably 88% by volume or less, and still more preferably 85% by volume or less.
  • the ethanol concentration is more preferably 32% by volume or more and 88% by volume or less, further 35% by volume or more and 85% by volume or less, further 50% by volume or more and 85% by volume or less, and further 60% by volume or more and 85% by volume or less. preferable.
  • (A) the poorly water-soluble polyphenols are dissolved in a high-concentration ethanol aqueous solution or ethanol, while the component (B) is dissolved in water or a low-concentration ethanol aqueous solution, and these two solutions are mixed.
  • the ethanol concentration is preferably 30% by volume or more and 90% by volume or less.
  • the ethanol concentration in the high-concentration ethanol aqueous solution for dissolving the component (A) is preferably 50% by volume or more, more preferably 70% by volume or more, further 80% by volume or more, and further preferably 90% by volume or more.
  • the upper limit is not particularly limited, but is preferably 100% by volume or less, and more preferably 95% by volume or less.
  • the solvent for dissolving the component (B) is preferably water, but the ethanol concentration when a low-concentration aqueous ethanol solution is used is preferably 50% by volume or less, further 40% by volume or less, further 30% by volume or less, and further 20% by volume. % Or less is preferable.
  • the temperature at which the slightly water-soluble polyphenols and the component (B) are dissolved in the above-mentioned ethanol aqueous solution is sufficient to be 0 ° C. or higher and 90 ° C. or lower. This is preferable in that it is possible and does not require special equipment.
  • the lower limit of the dissolution temperature is preferably 5 ° C. or higher, more preferably 10 ° C. or higher, from the viewpoint of increasing the solubility of the poorly water-soluble polyphenols.
  • the upper limit of the dissolution temperature is preferably 85 ° C. or less, more preferably 80 ° C. or less, further preferably 75 ° C. or less, further preferably 70 ° C. or less, and 60 ° C.
  • the melting temperature is preferably 5 ° C. or higher and 85 ° C. or lower, more preferably 10 ° C. or higher and 80 ° C. or lower, further preferably 10 ° C. or higher and 75 ° C. or lower, further preferably 10 ° C. or higher and 70 ° C. or lower, further preferably 10 ° C. or lower. More preferably, the temperature is 60 ° C. or lower.
  • the mass ratio [(A) / (B)] of the (A) poorly water-soluble polyphenols to the component (B) becomes higher as the solubility of the polyphenol composition obtained after drying increases.
  • a / B is preferably 0.01 or more and 10 or less, more preferably 0.05 or more and 8 or less, more preferably 0.1 or more and 7 or less, further preferably 0.1 or more and 5 or less, and 0.2 or more and 5 or less. The following is more preferable, and 0.3 or more and 5 or less are more preferable.
  • component (B) is dissolved in water or a low-concentration ethanol aqueous solution, and these solutions are mixed.
  • the content of the (A) poorly water-soluble polyphenols in the high-concentration ethanol aqueous solution or ethanol is preferably 0.5 g / L or more and 100 g / L or less, more preferably 1 g / L or more and 50 g / L or less, and 2 g / L or less. More preferably, it is not less than L and not more than 10 g / L.
  • the content of the component (B) in water or a low-concentration ethanol aqueous solution is preferably 0.5 g / L or more and 100 g / L or less, more preferably 1 g / L or more and 50 g / L or less, and 2 g / L or more and 10 g / L. L or less is more preferable.
  • the time required for dissolving the slightly water-soluble polyphenols varies depending on the operation, temperature, etc., but usually 0.1 minutes or more and 30 minutes or less is sufficient, 0.2 minutes or more and 15 minutes or less is preferable, and 5 minutes or more and 10 minutes or less are more preferable.
  • the step of cooling the solution to 50 ° C. or lower, more preferably 30 ° C. or lower, may be performed. Furthermore, you may perform the process of removing a solid part from a solution as needed.
  • the method for removing the solid part is not particularly limited, and can be performed, for example, by centrifugation, decantation, or filtration.
  • the present invention includes a step of drying the solution. Drying means removing the solvent from the solution.
  • drying means include freeze drying, evaporation to dryness, and spray drying. Among them, freeze-drying or spray-drying makes the polyphenol composition a solid state having no crystallinity, further increasing the solubility of the polyphenol composition in water, and (A) the initial solubility of the poorly water-soluble polyphenols. It is preferable from the point of improving.
  • the method of freeze drying or spray drying is not particularly limited, and a known method can be applied.
  • the treatment liquid in the case of spray drying, can be sprayed from a nozzle and dried by dropping in hot air of 100 ° C. or higher and 220 ° C. or lower, preferably 130 ° C. or higher and 190 ° C. or lower.
  • the treatment liquid in the case of lyophilization, can be frozen in liquid nitrogen, a cool bath, a freezer, etc., crushed, sieved, and then dried by sublimating moisture in a vacuum.
  • the freezing temperature of the treatment liquid is preferably ⁇ 70 ° C. or higher and 0 ° C. or lower.
  • the absolute pressure during drying is preferably from 0.1 Pa to 1000 Pa, more preferably from 0.5 Pa to 100 Pa, still more preferably from 1 Pa to 10 Pa. After spray drying or freeze drying, classification, granulation, pulverization, and the like may be performed as necessary.
  • the polyphenol composition thus obtained is in the form of powder, and when dissolved in water, the solubility of the poorly water-soluble polyphenols in water is improved by 4 times or more, particularly 4 to 40 times, Even underneath, precipitation of poorly water-soluble polyphenols is suppressed. Moreover, the influence of the catechins, chlorogenic acids, or methylated products of poorly water-soluble polyphenols on the flavor of the composition is small.
  • the polyphenol composition of the present invention can be used for various foods and beverages and pharmaceuticals.
  • confectionery such as beverages, breads, noodles, cookies, snacks, jelly, dairy products, frozen foods, instant foods such as powdered coffee, starch processed products, processed meat products, and other processed foods , Liquid, solid or semi-solid foods and beverages such as seasonings and dietary supplements.
  • pharmaceuticals include dosage forms such as tablets (such as chewable tablets), capsules, and powders.
  • the packaged beverage include tea-based beverages such as green tea, and non-tea beverages such as sports beverages, isotonic beverages, and near water.
  • the present invention further discloses the following manufacturing method.
  • ⁇ 1> One or more selected from (A) poorly water-soluble polyphenols and (B) methylated products of catechins, chlorogenic acids and poorly water-soluble polyphenols at 0 ° C. or higher and 90 ° C. or lower in ethanol
  • a method for producing a polyphenol composition comprising a step of dissolving and drying in an aqueous ethanol solution having a concentration of 30% by volume to 90% by volume.
  • the poorly water-soluble polyphenol is a polyphenol having a log P value of ⁇ 1.0 or more and 4.0 or less, preferably a polyphenol having a log P value of ⁇ 0.5 or more and 3.5 or less.
  • Production method. ⁇ 3> Slightly water-soluble polyphenols are preferably dissolved in water at 25 ° C. in an amount of preferably 5 g / L or less, more preferably 2 g / L or less, further 1 g / L or less, and further 0.5 g / L or less. Furthermore, the manufacturing method of ⁇ 1> or ⁇ 2> which is 0.1 g / L or less.
  • a poorly water-soluble polyphenol is preferably selected from flavonols, flavanones, flavones, isoflavones, phenolcarboxylic acids, anthocyanidins, hydroxycinnamic acid derivatives and ellagic acid, more preferably Rutin, quercitrin, isoquercitrin, quercetin, myricitrin, daidzein, daidzin, glycitein, glycitin, genistein, genistin, myricetin, hesperidin, neohesperidin, hesperetin, naringin, curcumin, lingenin, purnin, astragalin, kaempferol, resvera Troll, Apine, Apigenin, Delphinidin, Delphin, Nasnin, Peonidin, Peonin, Petunin, Peonidin, Malvidin, Malvin, Enine
  • the catechin is one or more selected from catechin, gallocatechin, catechin gallate, gallocatechin gallate, epicatechin, epigallocatechin, epicatechin gallate and epigallocatechin gallate ⁇ 1> to ⁇ 4 > Any manufacturing method of>.
  • Chlorogenic acids are monocaffeoylquinic acid of 3-caffeoylquinic acid, 4-caffeoylquinic acid and 5-caffeoylquinic acid, 3-feruloylquinic acid, 4-feruloylquinic acid and 5 -Ferroylquinic acid monoferuloylquinic acid and 3,4-dicaffeoylquinic acid and 3,5-dicaffeoylquinic acid and 4,5-dicaffeoylquinic acid dicaffeoylquinic acid ⁇ 1> to ⁇ 5>, which is one kind or two or more kinds.
  • the methylated product of poorly water-soluble polyphenols is preferably one or more selected from methyl hesperidin, methyl quercetin, methyl resveratrol and methyl rutin, more preferably methyl hesperidin ⁇ 1> to The manufacturing method in any one of ⁇ 6>.
  • the lower limit of the ethanol concentration of the aqueous ethanol solution is preferably 32% by volume or more, more preferably 35% by volume or more, still more preferably 40% by volume or more, still more preferably 50% by volume or more, still more preferably 60% by volume or more,
  • the upper limit of the ethanol concentration is preferably 88% by volume or less, more preferably 85% by volume or less, and still more preferably the ethanol concentration is 32% by volume or more and 88% by volume or less, preferably 35%.
  • the production method according to any one of ⁇ 1> to ⁇ 7>, wherein the volume% is 85% by volume or less, more preferably 50% by volume or more and 85% by volume or less, and further preferably 60% by volume or more and 85% by volume or less.
  • the lower limit of the dissolution temperature is preferably 5 ° C or higher, more preferably 10 ° C or higher, and the upper limit of the dissolution temperature is preferably 85 ° C or lower, more preferably 80 ° C or lower, more preferably 75 ° C. or lower, more preferably 70 ° C. or lower, more preferably 60 ° C. or lower, more preferably 5 ° C. or higher and 85 ° C. or lower, preferably 10 ° C. or higher and 80 ° C. or lower, more preferably 10 ° C. or higher and 75 ° C. or lower.
  • the production method according to any one of ⁇ 1> to ⁇ 8>, in which the temperature is 10 ° C. or lower, more preferably 10 ° C.
  • the dissolution treatment is preferably performed at a temperature of 0 ° C. or more and 90 ° C. or less, and (A) a slightly water-soluble polyphenol and component (B) are mixed in an ethanol aqueous solution of 30% by volume to 90% by volume.
  • the production method according to any one of ⁇ 1> to ⁇ 9>, which dissolves.
  • Dissolution treatment preferably dissolves (A) poorly water-soluble polyphenols in 50% by volume or more ethanol aqueous solution or ethanol, while component (B) is water or 50% by volume ethanol aqueous solution, preferably These two solutions are mixed so as to have an ethanol concentration of 30% by volume or more and 90% by volume or less by dissolving in water, and the temperature is set to 0 ° C. or more and 90 ° C. or less.
  • component (B) is water or 50% by volume ethanol aqueous solution, preferably
  • the mass ratio [(A) / (B)] of the (A) poorly water-soluble polyphenols to the component (B) is preferably 0.01 or more, more preferably 0.05 or more, still more preferably 0.00.
  • the sample injection amount was 10 ⁇ L, detection was determined by absorbance at a wavelength of 320 nm for ferulic acid, a wavelength of 283 nm for quercetin, and 360 nm for methyl hesperidin.
  • the ellagic acid was quantified using the same apparatus and setting only the gradient conditions as follows. Time (min) A liquid (%) B liquid (%) 0 99 1 10 90 10 20 85 15 40 10 90 50 10 90 50.1 85 15 60 85 15 The sample injection amount was 10 ⁇ L and quantified by absorbance at a wavelength of 254 nm.
  • the 1-octanol phase and the aqueous phase were separated by centrifugation, and the concentration of polyphenols in each phase was measured by HPLC in the same manner as in the above [Measurement of poorly water-soluble polyphenol].
  • the value obtained by taking the common logarithm of the distribution coefficient between the two phases was defined as the logP value.
  • a sample was appropriately diluted with distilled water, and a high-performance liquid chromatograph (model) manufactured by Shimadzu Corporation, equipped with a packed column for liquid chromatography L-column TM ODS (4.6 mm ⁇ ⁇ 250 mm: manufactured by Chemical Substance Evaluation Research Organization) SCL-10AVP) and a gradient method at a column temperature of 35 ° C.
  • the mobile phase A solution was a distilled aqueous solution containing 0.1 mol / L of acetic acid
  • the B solution was an acetonitrile solution containing 0.1 mol / L of acetic acid
  • the sample injection amount was 20 ⁇ L
  • the UV detector wavelength was 280 nm.
  • Example 1 10 g of ferulic acid preparation (manufactured by Tsukino Food Industry Co., Ltd., ferulic acid content 100%) was dissolved in 1270 g of 95% by volume ethanol. In addition, 25 g of chlorogenic acid preparation (purified and dried coffee beans extract (chlorogenic acid content 40%)) was dissolved in 380 g of water. These two liquids were mixed at room temperature (20 ° C. ⁇ 5 ° C.), and 2 L of the solution was dissolved.
  • chlorogenic acid preparation purified and dried coffee beans extract (chlorogenic acid content 40%)
  • the ethanol concentration of the solution was 79% by volume, and no turbidity was observed in the solution.
  • the solution was spray-dried (manufactured by Yamato Scientific Co., Ltd., SPRAY DRYER ADL311S, inlet air temperature 140). At a flow rate of 6.5 g / min to obtain a polyphenol composition in the form of a powder.
  • Example 2 5 g of ferulic acid preparation and 12.5 g of chlorogenic acid preparation were dissolved in 1 L of 60% by volume ethanol water. There was no turbidity in the solution. Spray drying was carried out in the same manner as in Example 1 to obtain a polyphenol composition.
  • Example 3 A polyphenol composition was obtained in the same manner as in Example 2 except that the ethanol water concentration was 50% by volume. Turbidity was not seen in the solution before drying.
  • Example 2 The same procedure as in Example 1 was performed except that the chlorogenic acid preparation was not used. Turbidity was not seen in the solution before drying.
  • Example 3 A polyphenol composition was obtained in the same manner as in Example 2 except that the ethanol water concentration was 95% by volume. The solution before drying was cloudy.
  • Example 4 A polyphenol composition was obtained in the same manner as in Example 2 except that the ethanol water concentration was 20% by volume. The solution before drying was cloudy.
  • Example 4 A polyphenol composition was obtained in the same manner as in Example 2 except that 5 g of ferulic acid preparation and 5 g of epigallocatechin gallate (EGCG) preparation (TEAVIGO manufactured by DMS Nutritional Products, EGCG content 100%) were used. Turbidity was not seen in the solution before drying.
  • EGCG epigallocatechin gallate
  • Example 5 The same procedure as in Example 1 was conducted except that 6 g of quercetin preparation (manufactured by ACROS ORGANICS, quercetin content 95%) was used instead of ferulic acid preparation, and 6 g of epigallocatechin gallate preparation was used instead of chlorogenic acid preparation. Turbidity was not seen in the mixed solution before drying.
  • Example 6 2 g of ellagic acid dihydrate (manufactured by Wako Pure Chemical Industries, Ltd., ellagic acid content 89%) was dissolved in 318 g of 95% by volume ethanol. Further, 5 g of chlorogenic acid preparation (same as Example 1) was dissolved in 95 g of water. These two liquids were mixed at 60 ° C. to prepare a 0.5 L solution. The ethanol concentration of the solution was 79% by volume. There was no turbidity in the solution. This solution was spray-dried in the same manner as in Example 1 to obtain a polyphenol composition in the form of a powder.
  • Example 7 2 g of ellagic acid dihydrate was dissolved in 318 g of 95% by volume ethanol. In addition, 4 g of epigallocatechin gallate preparation (same as Example 4) was dissolved in 95 g of water. These two liquids were mixed at 60 ° C. to prepare a 0.5 L solution. The ethanol concentration of the solution was 79% by volume. There was no turbidity in the solution. This solution was spray-dried in the same manner as in Example 1 to obtain a polyphenol composition in the form of a powder.
  • Example 8 2 g of ellagic acid dihydrate was dissolved in 318 g of 95% by volume ethanol. Further, 8 g of a methyl hesperidin preparation (manufactured by Hamari Pharmaceutical Co., Ltd., methyl hesperidin content 100 mass%) was dissolved in 95 g of water. These two liquids were mixed at 60 ° C. to prepare a 0.5 L solution. The ethanol concentration of the solution was 79% by volume. There was no turbidity in the solution. This solution was spray-dried in the same manner as in Example 1 to obtain a polyphenol composition in the form of a powder.
  • a hesperidin preparation manufactured by Hamari Pharmaceutical Co., Ltd., methyl hesperidin content 100 mass
  • Distilled water (25 ° C.) 5 mL is added to 0.525 g of the dried polyphenol composition, placed in a 20 mL glass sample bottle, and shaken at 25 ° C. for 5 minutes with a rotary shaker (manufactured by ASONE, 150 r / min). The solution was filtered through a membrane filter and quantified by HPLC.
  • the ethanol concentration is 30% by volume or more and 90% or less when the hardly water-soluble polyphenols and catechins, chlorogenic acids or methylated products of the poorly water-soluble polyphenols are subjected to a temperature condition of 0 ° C. or higher and 90 ° C. or lower.
  • the solubility of polyphenol in water of a polyphenol composition obtained by dissolving in an aqueous ethanol solution with a volume% or less and then drying was improved 4 to 40 times.
  • the influence on the flavor of the methylated product of catechins, chlorogenic acids, or poorly water-soluble polyphenols with respect to the obtained polyphenol composition is also small.
  • the odor derived from the component (B) of the obtained polyphenol composition was reduced.

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  • Life Sciences & Earth Sciences (AREA)
  • Botany (AREA)
  • Mycology (AREA)
  • Health & Medical Sciences (AREA)
  • Nutrition Science (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Coloring Foods And Improving Nutritive Qualities (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Non-Alcoholic Beverages (AREA)
  • Medicinal Preparation (AREA)
  • Anti-Oxidant Or Stabilizer Compositions (AREA)

Abstract

L'invention concerne un procédé de fabrication d'une composition de polyphénol ayant une excellente solubilité dans l'eau, où le procédé ne requiert pas d'équipement spécial, est bon marché et utilise une matière ayant peu d'impact sur la flaveur de la composition. Le procédé de fabrication d'une composition de polyphénol comprend une étape d'obtention d'une solution par dissolution (A) d'un polyphénol insoluble dans l'eau et (B) d'un ou plusieurs choisis dans le groupe consistant en la catéchine, l'acide chlorogénique et les produits de méthylation du polyphénol insolubles dans l'eau, dans une solution éthanolique aqueuse ayant une concentration en éthanol entre 30 et 90 % en volume inclus à une température entre 0 et 90°C inclus, et une étape de séchage de la solution résultante.
PCT/JP2013/064309 2012-05-24 2013-05-23 Procédé de fabrication d'une composition de polyphénol WO2013176206A1 (fr)

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JP6062666B2 (ja) * 2012-06-14 2017-01-18 森永製菓株式会社 水溶性向上剤、水溶性向上方法、及び、水溶液調製方法
EP3769760B1 (fr) * 2018-03-22 2023-01-04 Kao Corporation Procédé pour la production d'une dispersion solide contenant de la nobilétine

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JP2007308414A (ja) * 2006-05-18 2007-11-29 Kao Corp ヘスペリジン組成物
WO2011155505A1 (fr) * 2010-06-09 2011-12-15 花王株式会社 Procédé de fabrication d'une composition de polyphénol

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JP3455436B2 (ja) * 1998-08-17 2003-10-14 明治製菓株式会社 抗酸化物質の製造法
JPWO2006014028A1 (ja) * 2004-08-06 2008-05-01 持田製薬株式会社 サツマイモ茎葉抽出物およびその用途
US20090197942A1 (en) * 2006-05-23 2009-08-06 Kyusai Co., Ltd. Method For Producing Polyphenol-Rich Composition

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Publication number Priority date Publication date Assignee Title
JP2007308414A (ja) * 2006-05-18 2007-11-29 Kao Corp ヘスペリジン組成物
WO2011155505A1 (fr) * 2010-06-09 2011-12-15 花王株式会社 Procédé de fabrication d'une composition de polyphénol

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