WO2019087278A1 - ビサクロン抽出方法 - Google Patents
ビサクロン抽出方法 Download PDFInfo
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- WO2019087278A1 WO2019087278A1 PCT/JP2017/039261 JP2017039261W WO2019087278A1 WO 2019087278 A1 WO2019087278 A1 WO 2019087278A1 JP 2017039261 W JP2017039261 W JP 2017039261W WO 2019087278 A1 WO2019087278 A1 WO 2019087278A1
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- WIPO (PCT)
- Prior art keywords
- water
- bisacron
- turmeric
- organic solvent
- solvent
- Prior art date
Links
- 238000000605 extraction Methods 0.000 title abstract description 34
- QJOWFYQIUZMPRY-NEBZKDRISA-N (6s)-6-[(1r,4s,5s)-4,5-dihydroxy-4-methylcyclohex-2-en-1-yl]-2-methylhept-2-en-4-one Chemical compound CC(C)=CC(=O)C[C@H](C)[C@H]1C[C@H](O)[C@@](C)(O)C=C1 QJOWFYQIUZMPRY-NEBZKDRISA-N 0.000 title abstract 3
- MOTTXBGNWKHMBK-UHFFFAOYSA-N Bisacurone Natural products CC(CC(=O)C=C(C)C)C1CCC(C)(O)C(O)C1 MOTTXBGNWKHMBK-UHFFFAOYSA-N 0.000 title abstract 3
- QJOWFYQIUZMPRY-UHFFFAOYSA-N Bisacurone A Natural products CC(C)=CC(=O)CC(C)C1CC(O)C(C)(O)C=C1 QJOWFYQIUZMPRY-UHFFFAOYSA-N 0.000 title abstract 3
- 235000003373 curcuma longa Nutrition 0.000 claims abstract description 74
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- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
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- XXMFJKNOJSDQBM-UHFFFAOYSA-N 2,2,2-trifluoroacetic acid;hydrate Chemical compound [OH3+].[O-]C(=O)C(F)(F)F XXMFJKNOJSDQBM-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
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Images
Classifications
-
- 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
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- 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
- A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
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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
- A23L5/00—Preparation or treatment of foods or foodstuffs, in general; Food or foodstuffs obtained thereby; Materials therefor
- A23L5/20—Removal of unwanted matter, e.g. deodorisation or detoxification
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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
- A23L5/00—Preparation or treatment of foods or foodstuffs, in general; Food or foodstuffs obtained thereby; Materials therefor
- A23L5/20—Removal of unwanted matter, e.g. deodorisation or detoxification
- A23L5/23—Removal of unwanted matter, e.g. deodorisation or detoxification by extraction with solvents
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- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/88—Liliopsida (monocotyledons)
- A61K36/906—Zingiberaceae (Ginger family)
- A61K36/9066—Curcuma, e.g. common turmeric, East Indian arrowroot or mango ginger
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D17/00—Separation of liquids, not provided for elsewhere, e.g. by thermal diffusion
- B01D17/02—Separation of non-miscible liquids
- B01D17/0217—Separation of non-miscible liquids by centrifugal force
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D3/00—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping
- B01D3/34—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping with one or more auxiliary substances
- B01D3/343—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping with one or more auxiliary substances the substance being a gas
- B01D3/346—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping with one or more auxiliary substances the substance being a gas the gas being used for removing vapours, e.g. transport gas
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/79—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/80—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/24—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing hydroxy groups
- C07C49/242—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing hydroxy groups containing rings other than six-membered aromatic rings
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- 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
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- 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
- A23V2200/30—Foods, ingredients or supplements having a functional effect on health
- A23V2200/334—Foods, ingredients or supplements having a functional effect on health treating the effects of consuming alcohol, narcotics or other addictive behavior, e.g. treating hangover or reducing blood alcohol levels
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- 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
- A23V2300/00—Processes
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- A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
Definitions
- the present invention relates to an extraction method capable of purifying bisacron from turmeric at a high concentration without using a column operation, and a bisacron-containing turmeric extract obtained using the same.
- Bisacron is a minor component contained in turmeric, and it is known that it has an action to suppress a hangover symptom after alcohol intake, in addition to curcumin (yellow pigment) which is also contained in turmeric (patented) Literature 1).
- Patent Document 1 it is shown that intake of bisacron of 0.5 mg or more per one oral intake is necessary in order to obtain a suppressive effect of a hangover symptom by bisacron.
- Patent Document 2 shows that bisacron was obtained by water extraction from turmeric, and it is shown that the amount of bisacron in the obtained turmeric extract was about 0.15% by mass. Since the turmeric extract contains a large amount of components other than bisacron, in the food and drink containing the turmeric extract, these components may have a significant effect on the flavor of the food and drink. In order to eliminate the influence on such taste, higher bisacron concentration (purity) in the turmeric extract is required.
- Patent No. 5543656 Patent No. 5595614 gazette
- An object of the present invention is to provide a new means capable of purifying bisacron cheaper (that is, without using a column operation) and higher concentration than turmeric.
- bisacron can be dissolved in highly polar water or in less polar organic solvents due to a change in the molecular structure. I found it. Using this property, it has been found that bisacron can be purified from turmeric at a high concentration without using a column operation by combining and using a plurality of extraction solvents with different polarities in a predetermined order.
- the present invention is based on these findings and includes the following inventions.
- a method for producing a bisacron-containing turmeric extract which comprises: (1) A step of adding a water-based solvent to turmeric and mixing to extract a water-soluble component in turmeric, solid-liquid separation, and then recovering a solution containing the water-soluble component; (2) adding a hydrophobic organic solvent to the solution obtained in step (1) and mixing, and then separating and recovering the hydrophobic organic solvent phase, (3) removing the hydrophobic organic solvent from the obtained hydrophobic organic solvent phase to obtain a dried product; (4) An aqueous solvent is added to and mixed with the obtained dried solid, and after solid-liquid separation, a step of recovering the solution, Method, including.
- a method for producing a bisacron-containing turmeric extract comprising (1) A mixed solvent of a hydrophilic organic solvent and water is added and mixed with turmeric to extract a water-soluble component in turmeric, and after solid-liquid separation, a step of recovering a solution containing the water-soluble component; (2) removing the solvent from the solution obtained in step (1) to obtain a dried product; (3) A method comprising the steps of: adding and mixing water to the obtained dried solid, and performing solid-liquid separation, and then recovering an aqueous solution. [5] The method of [4], wherein the mixed solvent is acetone, ethanol, acetonitrile, or a mixed solvent of methanol and water. [6] A bisacron-containing turmeric extract produced by the method of any one of [1] to [5]. [7] A food and drink composition comprising the bisacron-containing turmeric extract of [6].
- bisacron can be purified from turmeric at a high concentration without using a column operation.
- FIG. 1 is a chart showing the results of HPLC analysis of bisacron extract obtained using a hydrophilic organic solvent.
- FIG. 2 is a chart showing the results of HPLC analysis of bisacron extract obtained using a hydrophobic organic solvent.
- FIG. 3 is a chart showing the results of HPLC analysis of a water extract of turmeric.
- FIG. 4 is a chart showing the results of HPLC analysis of column-purified bisacron extract.
- bisachron is a compound classified into bisaborane type sesquiterpenes, and means a compound having the following planar structural formula or a salt thereof.
- Bisacron has an asymmetric carbon at the position indicated by * in the planar structural formula, and thus there are several optical isomers, but in the present specification, bisacron is a concept including any of its optical isomers. is there.
- turmeric includes a plant belonging to the genus Curcuma of the ginger family, and may be any plant containing bisacron, and is not particularly limited.
- Curcuma longa alias: autumn turmeric
- Curcuma aromatica alias: spring turmeric
- Curcuma zedoaria alias: lizard or purple turmeric
- Curcuma phaeocaulis Curcuma kwangsiensis
- Curcuma a kwangsiensis
- Turmeric contains a suitable site (eg, rhizome etc.) containing bisacron, which may be in a form suitable for extraction of bisacron, either intact or cut into a suitable size or shape, or It is possible to use those in the form of pulverized materials, which may be suitably dried. Cutting and grinding of turmeric can be performed using a known method, and for example, a mill, a mixer, a homogenizer, etc. can be used.
- the method according to the present invention includes an embodiment (a first embodiment) including an aspect of using a hydrophobic organic solvent in an extraction and purification step, and does not utilize a hydrophobic organic solvent in an extraction and purification step (utilizes a hydrophilic organic solvent And an embodiment (a second embodiment) including an aspect).
- the method of the invention generally comprises the following steps: (1) extracting water-soluble components in turmeric and recovering a solution containing the water-soluble components; (2) adding and mixing a hydrophobic organic solvent to the obtained solution, and separating and recovering a hydrophobic organic solvent phase, (3) removing the hydrophobic organic solvent from the obtained hydrophobic organic solvent phase to obtain a dried product; (4) A step of recovering a water-soluble component from the obtained dried solid.
- Extraction of the water-soluble component in turmeric can be performed by mixing the said turmeric and the extraction solvent of a water-soluble component.
- the extraction solvent may be an aqueous solvent which can extract the water-soluble component of turmeric and does not mix with the following hydrophobic organic solvent, and as such an aqueous solvent, for example, water or hot water, or A mixed solvent of it and a lower alcohol hydrophilic organic solvent (for example, ethanol, methanol, isopropanol etc.) can be used.
- the turmeric and the aqueous solvent can be mixed by immersing turmeric in an extraction solvent at 5 ° C. to 100 ° C. for 3 minutes or more (eg, 1 hour to 72 hours, preferably 18 hours to 72 hours). If necessary, shaking or stirring may be added. The method of shaking and stirring can be appropriately determined by the practitioner.
- the amount of the aqueous solvent added to the turmeric is, for example, 1 to 500 parts by weight, preferably 1 to 100 parts by weight, and more preferably 5 to 50 parts by weight with respect to 1 part by weight of turmeric. If the amount of the extraction solvent added is too small, the water-soluble component may not be sufficiently extracted. On the other hand, if it is too large, undesirable problems such as a reduction in the working efficiency of the subsequent operation may occur.
- Solid-liquid separation of the obtained extract is performed to recover the liquid portion, whereby the water-insoluble component can be removed and a solution containing the target water-soluble component can be obtained.
- Solid-liquid separation can be performed by a general method, and means such as centrifugation and filtration can be used. Centrifugation can be performed, for example, by applying a centrifugal force of 1000 G or more, and filtration can be performed using, for example, a filter of 0.45 ⁇ m or less (not limited thereto).
- the resulting solution can be concentrated if necessary.
- the concentration of the solution can be performed by a common method such as distillation.
- An aqueous solvent may be added again to the obtained solution as needed, and this step, that is, extraction with the aqueous solvent may be repeated.
- the hydrophobic organic solvent is not particularly limited as long as it can dissolve bisacron from the solution obtained in step (1), but, for example, a solubility parameter (hereinafter referred to as "SP value") Can be used in a range of less than 9.5, preferably 8.5 to 9.5.
- SP value solubility parameter
- Such hydrophobic organic solvents include, but are not limited to, chloroform (9.4), ethyl acetate (9.0), butyl acetate (8.5), etc. ).
- the amount of the hydrophobic organic solvent added to the solution obtained in the step (1) is, for example, 0.5 to 10 parts by weight, preferably 1 to 3 with respect to 1 part by weight of the solution obtained in the step (1). It is a weight part. If the amount of the hydrophobic organic solvent added is too small, bisacron may not be sufficiently dissolved, while if it is too large, undesirable problems such as a reduction in the working efficiency of the subsequent operation may occur.
- the mixing of the solution obtained in step (1) with the hydrophobic organic solvent can be carried out, for example, by shaking or stirring for 60 seconds to 3600 seconds.
- the method of shaking and stirring can be appropriately determined by the practitioner.
- the hydrophobic organic solvent phase and the aqueous solvent phase are separated, and the aqueous solvent phase is removed or the hydrophobic organic solvent phase is recovered, thereby removing unnecessary water-soluble components and dissolving the bisacron in the hydrophobic state.
- Organic solvent phase can be obtained.
- the phase separation between the hydrophobic organic solvent phase and the aqueous solvent phase can be carried out by a general method, and means such as centrifugation or standing can be used.
- Step of removing the hydrophobic organic solvent from the obtained hydrophobic organic solvent phase to obtain a dried product In this step, the hydrophobic organic solvent is removed, and the component containing bisacron contained in the solvent is removed. to recover.
- the removal of the hydrophobic organic solvent can be carried out by a general method, and can be appropriately selected depending on the used hydrophobic organic solvent, such as reduced pressure drying, blast drying, heat drying, air drying, freeze drying and the like.
- Step of Recovering Water-Soluble Component from the Obtained Dry Matter the aqueous solvent is added to and mixed with the obtained dry matter to dissolve and recover bisacron in the aqueous solvent.
- the aqueous solvent is only required to be capable of dissolving bisacron in the dried product and not dissolving the water-insoluble component in the dried product.
- examples of such an aqueous solvent include water and hot water, Or lower alcohols (eg, ethanol, methanol, isopropanol, etc.), or both, but not limited thereto.
- lower alcohols eg, ethanol, methanol, isopropanol, etc.
- both water and the like and a lower alcohol hydrophilic organic solvent may be added sequentially or simultaneously (or as a mixed solvent).
- the amount of the aqueous solvent added to the dry matter is, for example, 1 to 10 parts by weight, preferably 2 to 4 parts by weight, per 1 part by weight of the dry matter. If the amount of the aqueous solvent to be added is too small, bisacron may not be sufficiently dissolved. On the contrary, if it is too large, undesirable problems such as a decrease in the working efficiency of the subsequent operation may occur.
- the mixing of the dry matter and the aqueous solvent may be carried out sufficiently to break the dry matter, for example, by shaking or stirring for 60 seconds to 3600 seconds.
- the method of shaking and stirring can be appropriately determined by the practitioner.
- Solid-liquid separation of the obtained extract is performed to recover the liquid portion, whereby the water-insoluble component can be removed and a solution containing bisacron in the target aqueous solvent can be obtained.
- Solid-liquid separation can be performed by a general method, and the above-mentioned means such as centrifugation and filtration can be used.
- the obtained solution containing bisacron can be used as it is as “bisacuron-containing turmeric extract” as it is, but may be further dried, for example, to a water content of 15% by weight or less, preferably 8 to 12% by weight. Dry up. In addition, the dried product may be pulverized as appropriate.
- the drying method can be carried out using a general method such as hot air drying, spray drying, lyophilization and the like.
- a pulverizing means used for pulverization for example, a stamp mill, mascaroider, comitolol, mulberry wood and the like can be mentioned.
- the particle size of the pulverized material can also be adjusted with a sieve if necessary.
- the purity of bisacron is higher than that of turmeric without performing column purification (for example, 0.5% or more, 1% or more, 5% or more, 10% or more, 15% or more, 20% or more, or
- the extraction and purification can be performed at a high recovery rate (for example, 50% or more, 60% or more, 65% or more, or 70% or more).
- step (1) adding water to turmeric to extract a water-soluble component in turmeric, removing the water-insoluble component and recovering an aqueous solution containing the water-soluble component;
- Ethyl acetate or chloroform is added to and mixed with the aqueous solution obtained in step (1), the phases are separated, and then the aqueous phase is removed to recover the organic solvent phase, (3) removing the organic solvent from the obtained organic solvent phase by distillation under reduced pressure to obtain a dried product;
- a lower alcohol is added to the obtained dried solid to dissolve, and then water is further added to dissolve it, and the water-insoluble component is removed to recover the solution containing the water-soluble component, Can be extracted and purified with high purity and high recovery rate.
- the method of the invention generally comprises the following steps: (1) adding and mixing a mixed solvent of a hydrophilic organic solvent and water to turmeric, extracting a water-soluble component in turmeric, and recovering a solution containing the water-soluble component; (2) removing the solvent from the obtained solution to obtain a dried product; (3) A step of adding and mixing water to the obtained dried solid to recover a water-soluble component.
- bisacron in turmeric is extracted
- the water-soluble component to be contained is extracted and recovered using a mixed solvent of a hydrophilic organic solvent and water (hereinafter simply referred to as "mixed solvent").
- the hydrophilic organic solvent is not particularly limited as long as it can extract the water-soluble component of turmeric when used in combination with water.
- it has an SP value of less than 15, preferably 10 to 15. You can use what is in the range.
- hydrophilic organic solvents include acetone (10.0), ethanol (12.7), methanol (14.5), isopropanol (11.5) and acetonitrile (11.9). There is no limitation to these (in parentheses, the SP value is shown).
- the mixing ratio of the hydrophilic organic solvent to water is not particularly limited, but preferably the hydrophilic organic solvent can be contained in a range of 90% or less and 30% or more by weight.
- the hydrophilic organic solvent can be contained in a range of 90% or less and 30% or more by weight.
- acetone and water can be mixed in a weight ratio in the range of 90:10 to 30:70, preferably in the range of 80:20 to 30:70.
- ethanol is used as the hydrophilic organic solvent
- ethanol and water can be mixed in a weight ratio of 90:10 to 30:70, preferably 80:20 to 30:70.
- methanol is used as a hydrophilic organic solvent
- methanol and water can be mixed in a weight ratio of 90:10 to 30:70, preferably 80:20 to 30:70. .
- bisacron By using a hydrophilic organic solvent and water at the above mixing ratio, bisacron can be extracted and purified with high purity and / or high recovery rate.
- Extraction of the water-soluble component in turmeric can be performed by mixing the turmeric and the mixed solvent.
- the turmeric and the mixed solvent can be mixed by immersing turmeric in an extraction solvent at 5 ° C. to 60 ° C. for 3 minutes or more (eg, 1 hour to 72 hours, preferably 18 hours to 72 hours). If necessary, shaking or stirring may be added. The method of shaking and stirring can be appropriately determined by the practitioner.
- the amount of the mixed solvent added to the turmeric is, for example, 1 to 500 parts by weight, preferably 1 to 100 parts by weight, more preferably 5 to 50 parts by weight with respect to 1 part by weight of turmeric. If the amount of the extraction solvent added is too small, the water-soluble component may not be sufficiently extracted. On the other hand, if it is too large, undesirable problems such as a reduction in the working efficiency of the subsequent operation may occur.
- Solid-liquid separation of the obtained extract is performed to recover the liquid portion, whereby the water-insoluble component can be removed and a solution containing the target water-soluble component can be obtained.
- Solid-liquid separation can be performed by a general method, and the above-mentioned means such as centrifugation and filtration can be used.
- a mixed solvent may be added again to the obtained solution, and this step, that is, extraction with the mixed solvent may be repeated.
- Step (2) Step of removing solvent from the obtained solution to obtain a dried product
- the solvent (mixed solvent) is removed from the solution obtained in step (1), and bisacron contained in the solvent Recover the ingredients that contain
- the removal of the solvent can be carried out by a general method, and can be appropriately selected according to the solvent used, such as reduced pressure drying, air drying, heat drying, air drying, freeze drying, and the like.
- a non-reactive gas nitrogen gas, argon gas, helium gas
- the amount of water added to the dry matter is, for example, 0.5 to 10 parts by weight, preferably 1 to 3 parts by weight, per 1 part by weight of the dry matter. If the amount of water added is too small, bisacron may not be sufficiently dissolved, while if it is too large, undesirable problems such as a decrease in the working efficiency of the subsequent operation may occur.
- the mixing of the dry matter and water may be performed sufficiently to break the dry matter, for example, by shaking or stirring for 60 seconds to 3600 seconds.
- the method of shaking and stirring can be appropriately determined by the practitioner.
- Solid-liquid separation of the obtained extract is performed to recover the liquid portion, whereby the water-insoluble component can be removed and an aqueous solution containing the target bisacron can be obtained.
- Solid-liquid separation can be performed by a general method, and the above-mentioned means such as centrifugation and filtration can be used.
- the obtained aqueous solution containing bisacron can be used as it is as “bisacuron-containing turmeric extract” as it is, but may be further dried, for example, to a water content of 15% by weight or less, preferably 8 to 12% by weight. Dry up. In addition, the dried product may be pulverized as appropriate.
- the drying method and the grinding means used for the grinding can be performed using the above-mentioned method.
- bisacron is higher in purity than turmeric (for example, 0.5% or more, 1.0% or more, 1.5% or more, 2.0% or more, or 2.5% or more), and Extraction and purification can be performed with high recovery rate (for example, 50% or more, 60% or more, 65% or more, 70% or more, 75% or more, 80% or more, or 85% or more).
- the bisacron-containing turmeric extract obtained by the methods of the first embodiment and the second embodiment can be used by being added to various food and drink products and pharmaceuticals without being limited to a specific usage mode. .
- the bisacron-containing turmeric extract of the present invention can be used in the form of a food and drink composition in combination with other materials acceptable for food and drink as required.
- the food and drink composition can be used as the main body, package, instruction manual, advertisement or electronic information for advertisement
- the indication of the efficacy for example, the indication that the effect of alleviating a hangover symptom, etc. may be attached.
- the form of the food and drink composition is not particularly limited, and may be in various forms such as solid, semi-solid and liquid.
- the bisacron-containing turmeric extract of the present invention can be formulated in combination with a pharmaceutically acceptable carrier, additive, excipient, etc. as required, and can be used in the form of a pharmaceutical composition.
- the pharmaceutical composition can be used to treat or prevent hangover symptoms.
- the dosage form of the pharmaceutical composition is not particularly limited and may be appropriately selected as necessary. Generally, tablets, capsules, granules, fine granules, powders, solutions, syrups, suspensions, and emulsions are used.
- the agent may be administered as an oral preparation such as elixir, or as a parenteral preparation such as injection, drip, suppository, inhalant, transdermal absorbent, transmucosal absorbent, patch, ointment and the like.
- Carriers, additives, excipients and the like in the pharmaceutical composition can be appropriately selected depending on the administration route.
- Test 1 Extraction Method Using a Hydrophilic Organic Solvent
- centrifugation was performed at 15000 rpm for 60 minutes to perform solid-liquid separation.
- the supernatant was recovered, and the hydrophilic organic solvent was evaporated by injecting nitrogen gas on the surface, and distilled water was added thereto so that the total volume would be 1.5 mL to precipitate the hydrophobic component.
- the final amount of bisacron was calculated from the concentration at the time of measurement, and the mass of dried powder was used to calculate the concentration of bisacron in the powder after drying, which was defined as purity (%).
- the bisacron concentration in the crushed turmeric used was calculated by HPLC measurement using a 50% ethanol (Wako Pure Chemical Industries, Ltd.) for 16 hours with shaking and stirring and calculated to be 0.59 mg / g. From this value and the initial weight, the theoretical value of the amount of bisacron in the initial turmeric crushed material was calculated, and the actual recovery amount was compared with this theoretical value to obtain a recovery rate (%).
- Test 2 Extraction Method Using Hydrophobic Organic Solvent
- two kinds of hydrophobic organic solvents ethyl acetate and chloroform, were used.
- the crushed turmeric (100 g, initial weight) was weighed into a 3 L jug made by Stellar, to which distilled water (2 L) was added, and stirring and mixing were performed for 16 hours.
- each hydrophobic organic solvent 700 mL was added to it, and after stirring for 2 minutes, it was allowed to stand for 10 minutes.
- hydrophobic organic solvent was removed from the recovered hydrophobic organic solvent phase using an evaporator and dried.
- the final amount of bisacron was calculated from the concentration at the time of measurement, and the mass of dried powder was used to calculate the concentration of bisacron in the powder after drying, which was defined as purity (%).
- the bisacron concentration in the crushed turmeric used was calculated by HPLC measurement using a 50% ethanol (Wako Pure Chemical Industries, Ltd.) for 16 hours with shaking and stirring and calculated to be 0.59 mg / g. From this value and the initial weight, the theoretical value of the amount of bisacron in the initial turmeric crushed material was calculated, and the actual recovery amount was compared with this theoretical value to obtain a recovery rate (%).
- FIG. 1 shows a chart of bisacron extract obtained by the method of Test 1.
- FIG. 2 shows a chart of bisacron extract obtained by the method of Test 2.
- FIG. 3 shows a chart of the water extract of turmeric.
- FIG. 4 shows a chart of column purified bisacron extract.
- the bisacron extract obtained by the method of the test 1 and the test 2 does not correspond to the column purified bisacron extract, but the bisacron which appears every 2 to 10 minutes of retention time as compared with the water extract of turmeric It was confirmed that the amount of other components was reduced.
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Abstract
Description
(1)ウコンに水系溶媒を添加混合して、ウコン中の水溶性成分を抽出し、固液分離した後、該水溶性成分を含む溶液を回収する工程;
(2)工程(1)で得られた溶液に疎水性有機溶媒を添加混合して、その後疎水性有機溶媒相を分離し、回収する工程、
(3)得られた該疎水性有機溶媒相より疎水性有機溶媒を除去して乾固物を得る工程、ならびに、
(4)得られた該乾固物に水系溶媒を添加混合して、固液分離した後、溶液を回収する工程、
を含む、方法。
[2] 疎水性有機溶媒の溶解性パラメータ(SP値)が、9.5未満である、[1]の方法。
[3] 疎水性有機溶媒が酢酸エチル、クロロホルム又は酢酸ブチルである、[1]又は[2]の方法。
[4] ビサクロン含有ウコン抽出物の製造方法であって、
(1)ウコンに親水性有機溶媒及び水の混合溶媒を添加混合して、ウコン中の水溶性成分を抽出し、固液分離した後、該水溶性成分を含む溶液を回収する工程;
(2)工程(1)で得られた溶液より溶媒を除去して乾固物を得る工程、ならびに、
(3)得られた該乾固物に水を添加混合して、固液分離した後、水溶液を回収する工程、を含む、方法。
[5] 混合溶媒が、アセトン、エタノール、アセトニトリル、又はメタノールと水の混合溶媒である、[4]の方法。
[6] [1]~[5]のいずれかの方法によって製造されたビサクロン含有ウコン抽出物。
[7] [6]のビサクロン含有ウコン抽出物を含有する飲食品組成物。
[1.疎水性有機溶媒を利用する第一の実施形態]
本発明方法は概ね以下の工程を含む:
(1)ウコン中の水溶性成分を抽出し、水溶性成分を含む溶液を回収する工程;
(2)得られた溶液に疎水性有機溶媒を添加混合し、疎水性有機溶媒相を分離・回収する工程、
(3)得られた疎水性有機溶媒相より疎水性有機溶媒を除去して乾固物を得る工程、ならびに、
(4)得られた乾固物より水溶性成分を回収する工程。
本工程においては、ウコン中のビサクロンを含む水溶性成分を、抽出溶媒を用いて、抽出・回収する。
本工程においては、工程(1)で得られた水溶性成分を含む溶液に疎水性有機溶媒を添加混合することによって、工程(1)で得られた溶液中のビサクロンは疎水性有機溶媒へと転溶する。
本工程においては、疎水性有機溶媒を除去し、当該溶媒中に含まれるビサクロンを含む成分を回収する。
本工程においては、得られた乾固物に水系溶媒を添加混合することによって、水系溶媒中にビサクロンを溶解して回収する。
(1)ウコンに水を加えてウコン中の水溶性成分を抽出し、水不溶性成分を除去して水溶性成分を含む水溶液を回収する工程;
(2)工程(1)で得られた水溶液に、酢酸エチル又はクロロホルムを添加混合し、相分離させた後、水相を除去して有機溶媒相を回収する工程、
(3)得られた有機溶媒相より有機溶媒を減圧蒸留により除去して、乾固物を得る工程、ならびに、
(4)得られた乾固物に低級アルコールを加えて溶解し、次いでさらに水を加えて溶解し、水不溶性成分を除去して水溶性成分を含む溶液を回収する工程、
を含み、ビサクロンを高い純度で、かつ高い回収率で抽出・精製することができる。
本発明方法は概ね以下の工程を含む:
(1)ウコンに親水性有機溶媒及び水の混合溶媒を添加混合して、ウコン中の水溶性成分を抽出し、水溶性成分を含む溶液を回収する工程;
(2)得られた溶液より溶媒を除去して乾固物を得る工程、ならびに、
(3)得られた乾固物に水を添加混合して、水溶性成分を回収する工程。
(1)ウコンに親水性有機溶媒及び水の混合溶媒を添加混合して、ウコン中の水溶性成分を抽出し、水溶性成分を含む溶液を回収する工程
本工程においては、ウコン中のビサクロンを含む水溶性成分を、親水性有機溶媒及び水の混合溶媒(以下、単に「混合溶媒」と記載する)を用いて、抽出・回収する。
本工程においては、工程(1)で得られた溶液から溶媒(混合溶媒)を除去し、当該溶媒中に含まれるビサクロンを含む成分を回収する。
本工程においては、得られた乾固物に水を添加混合することによって、水中にビサクロンを溶解して回収する。
(1)ウコンにアセトン、エタノール、もしくはメタノール、及び水の混合溶媒を添加混合して、ウコン中の水溶性成分を抽出し、水不溶性成分を除去して水溶性成分を含む溶液を回収する工程;
(2)得られた溶液より溶媒を蒸発させ除去して乾固物を得る工程、ならびに、
(3)得られた乾固物に水を加えて溶解し、水不溶性成分を除去して水溶性成分を含む水溶液を回収する工程、
を含み、ウコンよりビサクロンを高い純度で、かつ高い回収率で抽出・精製することができる。
ビサクロン10mg(長良サイエンス(株)製)を500mLビーカーに精驃量秤し、30%アセトニトリル(和光純薬)溶液を500mL添加溶解し、20ppmビサクロン標品とした。それを30%アセトニトリル溶液でさらに希釈し、10ppm,8ppm,4ppm,2ppm,0.8ppm標品を作製した。
秋ウコン(Curcuma longa)の根茎を乾燥させたウコンチップを適当量、コーヒーミルIFM-800(IWATANI製)で2分間破砕しウコン破砕物とした。
各最終サンプルを30%アセトニトリル溶液でビサクロン濃度が20ppm以下になるように希釈し、0.45μmフィルターでろ過しサンプル溶液とした。
装 置:Waters ACQUITY H-Classシステム
カラム:Waters XBridge C18 5μm 6×250mm
温 度:50℃
流 量:1.0mL/min
移動相:30%アセトニトリル(pH3.3)TFA水(和光純薬)
検出器:UV240nm
試験には、アセトン、エタノール、メタノールの3種類の親水性有機溶媒を用いた。
試験には、酢酸エチル、クロロホルムの2種類の疎水性有機溶媒を用いた。
上記試験1及び試験2の方法で得られた各ビサクロン抽出物ならびに、ウコンの水抽出物(試験1の比較例)、及びカラム精製されたビサクロン抽出物(秋ウコン(Curcuma longa)の根茎部分を水を用いて抽出し、得られた水抽出液をメタノールにて再抽出し、得られたメタノール抽出液より分取カラムを用いて精製したもの)について、HPLC分析した結果、得られたチャートを図1~4に示す。
Claims (7)
- ビサクロン含有ウコン抽出物の製造方法であって、
(1)ウコンに水系溶媒を添加混合して、ウコン中の水溶性成分を抽出し、固液分離した後、該水溶性成分を含む溶液を回収する工程;
(2)工程(1)で得られた溶液に疎水性有機溶媒を添加混合して、その後疎水性有機溶媒相を分離し、回収する工程、
(3)得られた該疎水性有機溶媒相より疎水性有機溶媒を除去して乾固物を得る工程、ならびに、
(4)得られた該乾固物に水系溶媒を添加混合して、固液分離した後、溶液を回収する工程、
を含む、方法。 - 疎水性有機溶媒の溶解性パラメータ(SP値)が、9.5未満である、請求項1に記載の方法。
- 疎水性有機溶媒が酢酸エチル、クロロホルム又は酢酸ブチルである、請求項1又は2に記載の方法。
- ビサクロン含有ウコン抽出物の製造方法であって、
(1)ウコンに親水性有機溶媒及び水の混合溶媒を添加混合して、ウコン中の水溶性成分を抽出し、固液分離した後、該水溶性成分を含む溶液を回収する工程;
(2)工程(1)で得られた溶液より溶媒を除去して乾固物を得る工程、ならびに、
(3)得られた該乾固物に水を添加混合して、固液分離した後、水溶液を回収する工程、を含む、方法。 - 混合溶媒が、アセトン、エタノール、アセトニトリル、又はメタノールと水の混合溶媒である、請求項4に記載の方法。
- 請求項1~5のいずれか一項に記載の方法によって製造されたビサクロン含有ウコン抽出物。
- 請求項6に記載のビサクロン含有ウコン抽出物を含有する飲食品組成物。
Priority Applications (5)
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KR1020207014593A KR102485101B1 (ko) | 2017-10-31 | 2017-10-31 | 비사쿠론 추출 방법 |
PCT/JP2017/039261 WO2019087278A1 (ja) | 2017-10-31 | 2017-10-31 | ビサクロン抽出方法 |
CA3081207A CA3081207C (en) | 2017-10-31 | 2017-10-31 | Bisacurone extraction method |
CN201780096350.4A CN111278301A (zh) | 2017-10-31 | 2017-10-31 | 甜没药姜黄醇提取方法 |
US16/760,079 US20200288761A1 (en) | 2017-10-31 | 2017-10-31 | Bisacurone extraction method |
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PCT/JP2017/039261 WO2019087278A1 (ja) | 2017-10-31 | 2017-10-31 | ビサクロン抽出方法 |
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KR (1) | KR102485101B1 (ja) |
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WO2021002335A1 (ja) * | 2019-07-01 | 2021-01-07 | ハウスウェルネスフーズ株式会社 | 血中グルコース濃度低減用、血中ヘモグロビンA1c量低減用又は血中HDL-コレステロール量増加用組成物 |
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CN114736182B (zh) * | 2022-05-10 | 2023-08-08 | 云南中医药大学 | 一种抗心肌缺血再灌注损伤的化合物和傣药组合物及其应用 |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2007284373A (ja) * | 2006-04-14 | 2007-11-01 | Okinawa Green Life:Kk | アントシアニジン及びその抽出方法。 |
JP2012153618A (ja) * | 2011-01-24 | 2012-08-16 | Kao Corp | Trpv3活性化剤 |
JP2015143200A (ja) * | 2013-12-27 | 2015-08-06 | ハウスウェルネスフーズ株式会社 | Vcam−1発現抑制剤 |
JP2016199491A (ja) * | 2015-04-09 | 2016-12-01 | ハウスウェルネスフーズ株式会社 | 気分状態改善剤 |
Family Cites Families (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2422398B2 (de) | 1974-05-09 | 1976-07-22 | Siemens AG, 1000 Berlin und 8000 München | Gehaeuse fuer ein geraet der elektrischen nachrichtentechnik, insbesondere richtfunktechnik |
CA2566202A1 (en) * | 2004-05-31 | 2005-12-08 | Kaneka Corporation | Agent for preventing/ameliorating life style-related diseases containing turmeric essential oil component |
CN100594928C (zh) * | 2006-09-27 | 2010-03-24 | 贵州师范大学 | 姜黄提取物及其制备方法、药物组合物和用途 |
JP5764288B2 (ja) * | 2009-09-24 | 2015-08-19 | ハウス食品グループ本社株式会社 | ウコン抽出物とガジュツ抽出物とを含有する組成物 |
CN102948736A (zh) * | 2011-08-25 | 2013-03-06 | 好侍食品株式会社 | 含有姜黄提取物的组合物 |
CN103163244B (zh) * | 2013-03-08 | 2014-12-10 | 南京中医药大学 | 一种倍半萜类和姜黄素类成分同时测定的方法 |
JP5543656B1 (ja) * | 2013-03-29 | 2014-07-09 | ハウス食品グループ本社株式会社 | ウコン中の有用成分を含有する組成物 |
JP5595614B1 (ja) | 2013-09-30 | 2014-09-24 | ハウス食品グループ本社株式会社 | 肝臓加水分解物含有液状組成物 |
JP5543651B1 (ja) * | 2013-09-30 | 2014-07-09 | ハウス食品グループ本社株式会社 | ウコン中の有用成分及びウコン色素を含有する液状組成物 |
CN105211995A (zh) * | 2014-07-01 | 2016-01-06 | 好侍食品集团本社株式会社 | 稳定地含有姜黄中的有用成分的饮料 |
CN105265919A (zh) * | 2014-07-01 | 2016-01-27 | 好侍食品集团本社株式会社 | 含有姜黄中的有用成分的饮料的制造方法 |
CN107089992B (zh) * | 2017-06-07 | 2019-11-22 | 浙江大学 | 一种姜黄属植物总倍半萜及三种倍半萜单体及制备方法和用途 |
-
2017
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- 2017-10-31 US US16/760,079 patent/US20200288761A1/en not_active Abandoned
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- 2017-10-31 CA CA3081207A patent/CA3081207C/en active Active
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Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2007284373A (ja) * | 2006-04-14 | 2007-11-01 | Okinawa Green Life:Kk | アントシアニジン及びその抽出方法。 |
JP2012153618A (ja) * | 2011-01-24 | 2012-08-16 | Kao Corp | Trpv3活性化剤 |
JP2015143200A (ja) * | 2013-12-27 | 2015-08-06 | ハウスウェルネスフーズ株式会社 | Vcam−1発現抑制剤 |
JP2016199491A (ja) * | 2015-04-09 | 2016-12-01 | ハウスウェルネスフーズ株式会社 | 気分状態改善剤 |
Non-Patent Citations (1)
Title |
---|
SUN, D. I. ET AL.: "Bisacurone inhibits adhesion of inflammatory monocytes or cancer cells to endothelial cells through down-regulation of VCAM- 1 expression", INT. IMMUNOPHARMACOL., vol. 8, no. 9, 2008, pages 1272 - 1281, XP022819491, ISSN: 1567-5769, DOI: doi:10.1016/j.intimp.2008.05.006 * |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2021002335A1 (ja) * | 2019-07-01 | 2021-01-07 | ハウスウェルネスフーズ株式会社 | 血中グルコース濃度低減用、血中ヘモグロビンA1c量低減用又は血中HDL-コレステロール量増加用組成物 |
JP2021008434A (ja) * | 2019-07-01 | 2021-01-28 | ハウスウェルネスフーズ株式会社 | 血中グルコース濃度低減用、血中ヘモグロビンA1c量低減用又は血中HDL−コレステロール量増加用組成物 |
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US20200288761A1 (en) | 2020-09-17 |
KR20200074189A (ko) | 2020-06-24 |
CA3081207C (en) | 2022-02-22 |
CN111278301A (zh) | 2020-06-12 |
CA3081207A1 (en) | 2019-05-09 |
KR102485101B1 (ko) | 2023-01-04 |
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