JP2022127020A - High-purity alpinia speciosa extract and method for producing the same - Google Patents

Abstract

To provide a method for producing an Alpinia speciosa extract having higher purity of α-pyrone as compared with conventional arts.SOLUTION: A method for producing an Alpinia speciosa extract includes the steps of: subjecting a dried product of Alpinia speciosa to extraction treatment using a dehydrokawain soluble solvent, to obtain an Alpinia speciosa crude extract; and subjecting the Alpinia speciosa crude extract to water-adding treatment and alkali treatment or water-adding treatment, alkali treatment and salting-out, to obtain an Alpinia speciosa extract.SELECTED DRAWING: Figure 1

Description

TECHNICAL FIELD The present invention relates to a high-purity Alpinia speciosa extract and a method for producing the same.

Alpinia alba extract is known as one of the ingredients involved in functionality in foods with function claims. The functionality of shell ginger extract is said to be a skin-beautifying effect that helps to moisturize the skin of people who tend to have dry skin.

In the Alpinia shell extract, the indicator components are two kinds of α-pyrones, dihydro-5,6-dehydrokawaine and 5,6-dehydrokawaine. Due to the inclusion of these α-pyrones, the Alpinia speciosa extract is believed to exhibit skin-beautifying effects through fibroblast proliferation-promoting action, collagen production-promoting action, and collagenase activity-inhibiting action.

As a method for producing the shell ginger leaf extract, a method of subjecting shell ginger leaves to ethanol extraction treatment by adding water-containing ethanol, a method of subjecting shell ginger leaves to water and subjecting to hot water extraction treatment by heating, etc. are known (for example, patent See Reference 1).

Japanese Patent Application Laid-Open No. 2002-302453

However, in the method of subjecting shell ginger leaves to ethanol extraction treatment or hot water extraction treatment described in Patent Document 1, the obtained extract contains sugars, flavonoids, etc. in addition to α-pyrones, and α-pyrones There is a problem of low purity.

Therefore, an object of the present invention is to provide a method for producing a shell ginger extract with higher purity of α-pyrones than the method described in Patent Document 1.

As a result of intensive studies to solve the above problems, the present inventors have focused on the state of shell ginger used in the extraction process and further processing after the extraction process. Then, by repeating trial and error, such as using shell ginger in various states and applying various processes to the extracted product, surprisingly, solvent extraction treatment using dried shell ginger was achieved. After performing the above, by subjecting the obtained solvent extraction product to hydrolysis and alkali treatment, it was found that a shell ginger extract containing highly purified α-pyrones can be obtained. As a result, the present inventors succeeded in creating a method for producing an extract of shell ginger containing highly purified α-pyrones from shell ginger. The present invention is an invention completed based on such knowledge and successful examples.

Therefore, according to the present invention, methods and extracts of shell ginger according to the following aspects are provided.
[1] A step of obtaining a crude extract of shell ginger by subjecting the dry substance of shell ginger to an extraction treatment using a dehydrokawaine-soluble solvent;
A method for producing an Alpinia speciosa extract, comprising a step of subjecting an Alpinia speciosa crude extract to hydrolysis and alkali treatment to obtain an Alpinia speciosa extract.
[2] A step of obtaining a crude extract of shell ginger by subjecting the dry substance of shell ginger to an extraction treatment using a dehydrokawaine-soluble solvent;
A method for producing an shell ginger extract, comprising a step of subjecting a shell core crude extract to hydrolysis, alkali treatment and salting out to obtain the shell ginger extract.
[3] The crude extract of shell ginger is a crude extract of shell ginger obtained by subjecting the extract obtained by the extraction process to solid-liquid separation treatment and/or concentration treatment, [1] to [2] A method according to any one of
[4] The method according to any one of [2] to [3], wherein the salting out is salting out using at least one saccharide selected from the group consisting of glucose, sucrose and maltose.
[5] The method according to any one of [1] to [4], wherein the dehydrokawaine-soluble solvent is 30% (v/v) to 90% (v/v) hydrous ethanol.
[6] Any of [1] to [5], wherein the alkali treatment is an alkali treatment using sodium hydroxide with a final concentration of 0.5% (w / v) to 6% (w / v) or the method according to item 1.
[7] Any one of [1] to [6], wherein the extract of Alpinia speciosa has a total content of dihydro-5,6-dehydrokawaine and 5,6-dehydrokawaine of 80% (w/w) or more. or the method according to item 1.
[8] The shell ginger extract has a dihydro-5,6-dehydrokawaine content of 70% (w/w) or more, and/or a 5,6-dehydrokawaine content of 10% (w/w). /w) or more, the method according to any one of [1] to [7].
[9] The method according to any one of [1] to [8], wherein the shell ginger extract is a solid shell ginger extract.
[10] The total content of dihydro-5,6-dehydrokawaine and 5,6-dehydrokawaine is 80% (w/w) or more, and dihydro-5,6-dehydrokawaine and 5,6-dehydrokawaine is an shell ginger extract derived from shell ginger.
[11] The shell ginger extract has a dihydro-5,6-dehydrokawaine content of 80% (w/w) or more, and/or a 5,6-dehydrokawaine content of 10% (w/w). /w) The shell ginger extract according to [10], which is above.

According to the method of one aspect of the present invention, shell ginger is used as a raw material to produce an extract containing highly purified α-pyrones such as dihydro-5,6-dehydrokawaine and 5,6-dehydrokawaine. be able to. In addition, since the processing operations employed in the method of the present invention are simple and safe, the method of one embodiment of the present invention enables the production of a large amount of Alpinia alba extract on an industrial scale. Therefore, the method of one aspect of the present invention is a method for producing a highly pure Alpinia alba extract, which is industrially practical, rapid, safe and economical.

Since the shell ginger extract obtained by the method of one aspect of the present invention can be solid, it can be processed into various dosage forms, can be added to various foods, drinks and cosmetics, and can be stored. It can be widely distributed because it has excellent properties.

FIG. 1 is a flow diagram showing an outline of a method for producing a high-purity shell ginger extract using shell ginger as a raw material according to example 1, as described in the examples below. FIG. 2 is a flow diagram showing an outline of a method for producing a high-purity shell ginger extract using shell ginger as a raw material according to example 2, as described in the later-described examples. FIG. 3 is a flow chart showing an outline of a method for producing a high-purity shell ginger extract using shell ginger as a raw material according to example 3, as described in the examples below. FIG. 4 is a flow chart showing an outline of a method for producing a high-purity extract of shell ginger using shell ginger leaves as a raw material according to example 4, as described in the examples below.

Each aspect of the present invention will be described in detail below, but the present invention can take various aspects as long as it achieves its object.

Unless otherwise specified, each term in this specification is used in the meaning normally used by those skilled in the art in the food field, cosmetics field, etc., and should not be interpreted as having an unduly restrictive meaning. do not have. In addition, the speculations and theories made in the present specification are based on the knowledge and experience of the present inventors, so the present invention is not bound solely by such speculations and theories. do not have.

The term "and/or" means any one, or any or all combinations of two or more of the associated listed items.
"Content" is synonymous with concentration and amount used (added amount), and means the ratio of the amount of the component to the total amount of Alpinia shell extract. However, the total content of the components does not exceed 100%. "Purity" is used synonymously with content. That is, a highly pure component means a component occupying a high proportion in the Alpinia shell extract.
The unit "vol%" is synonymous with "% (v/v)" and "% by volume". The unit "wt%" is synonymous with "% (w/w)" and "% by mass". The unit "% (w/v)" is synonymous with "mass volume %".
"-" in a numerical range is a range including the numerical values before and after it, for example, "0% to 100%" means a range of 0% or more and 100% or less. "greater than" and "less than" mean the lower and upper limits, respectively, excluding the preceding number; means.
"Contains" means that it can add elements other than those explicitly included (which is synonymous with "including at least"), but includes "consisting of" and "consisting essentially of" . That is, "comprising" can mean including the specified element and any one or more elements, consisting of, or consisting essentially of the specified element. . Elements include restrictions on components, steps, conditions, parameters, and the like.

The number of digits in the integer value and the number of significant digits are the same. For example, 1 has 1 significant digit and 10 has 2 significant digits. Also, for decimal values, the number of digits after the decimal point and the number of significant digits are the same. For example, 0.1 has one significant digit and 0.10 has two significant digits.

As used herein, dihydro-5,6-dehydrokawaine may be referred to as "DDK" and 5,6-dehydrokawaine may be referred to as "DK.""Dehydrokawaine" is a generic term for either one of DDK and DK, or a combination of DDK and DK. DDK and DK are compounds having the following structures.

A method of one aspect of the present invention is a method for producing an Alpinia alba extract containing highly purified dehydrokawaine. In the method of one embodiment of the present invention, the raw material shell ginger is subjected to solvent extraction treatment, hydration treatment and alkali treatment or solvent extraction treatment, hydration treatment, alkali treatment and salting out to obtain dehydrogenate extract as shell ginger extract. A kawaine inclusion is obtained.

A first aspect of the method of the present invention includes the following steps (1) and (2).
(1) Step of obtaining a crude extract of shell ginger by subjecting the dry substance of shell ginger to an extraction treatment using a dehydrokawaine-soluble solvent (2) By subjecting the crude extract of shell ginger to water treatment and alkali treatment , the process of obtaining shell ginger extract

A second aspect of the method of the present invention comprises the following steps (1) and (2)'.
(1) Process of obtaining a crude extract of shell ginger by subjecting the dry substance of shell ginger to an extraction treatment using a dehydrokawaine-soluble solvent (2)' treating the crude extract of shell ginger with water, alkali treatment, and salting out A step of obtaining shell ginger extract by subjecting to

In the step (1), a crude extract of shell ginger is obtained by subjecting the dry substance of shell ginger to an extraction treatment using a dehydrokawaine-soluble solvent.

Alpinia zerumbet, also called Alpinia zerumbet , is an evergreen perennial plant known to grow naturally from the southern tip of Kyushu to Okinawa Prefecture, Taiwan to southern China, Southeast Asia and India. Shell ginger is known to have fibroblast growth promoting action, collagen production promoting action, and collagen degrading enzyme activity inhibiting action, and it is ingested with the expectation of skin beautifying effects through these. In addition, shell ginger is a natural plant that has been ingested by humans for a long period of time and is highly safe.

The part of shell ginger used is not particularly limited as long as it contains dehydrokawaine, and examples include leaves, flowers, roots, stems, fruits, seeds, etc., preferably dehydrokawaine-rich leaves, flowers and is the root. Shell ginger may be a single part such as leaves, flowers, or roots, or may be a combination of two or more of these parts.

When shell ginger is in a state of being collected, the efficiency of the extraction process tends to decrease. Therefore, as shell ginger, dried shell ginger obtained by subjecting shell ginger to drying treatment is used. The drying treatment is not particularly limited, and for example, the weight after drying the shell ginger (dry weight) is about 1/100 to 9/10 of the weight before drying (wet weight). are mentioned. The drying treatment may be performed by any method known to those skilled in the art, such as hot air drying, vacuum drying, low temperature vacuum drying, high pressure steam drying, electromagnetic wave drying, freeze drying, and air drying. Although the moisture content of the dried shell ginger is not particularly limited, for example, it is preferably 20% or less, more preferably 10% or less.

From the viewpoint of increasing the contact area with the solvent and performing the extraction treatment efficiently, the shell ginger is preferably in a state of being shredded, crushed, pulverized or ground. The method of shredding, crushing, pulverizing or grinding shell ginger is not particularly limited, but examples include methods using cutters, slicers, cutters, crushers, blenders, mixers, mills, grinders, kneaders, mortars, millstones, and the like. be able to.

The dried shell ginger used in step (1) is preferably a powdery dried shell ginger in order to improve the efficiency of the extraction process when roots, stems, seeds, etc. are used as shell ginger. When obtaining a powdery dried shell ginger, the drying treatment and the pulverizing treatment may be performed at the same time, or one of the treatments may be performed first, and then the other treatment may be performed. It is preferable to perform the pulverization treatment after performing the drying treatment first from the viewpoint of properties.

The dehydrokawaine-soluble solvent is not particularly limited as long as it is a solvent capable of dissolving dehydrokawaine. For example, a solvent that readily dissolves dehydrokawaine, specifically water; lower alcohols; lower esters such as ethyl acetate and methyl acetate; dimethylsulfoxide, acetonitrile, acetone, hexane, glycerin, propylene glycol and the like. The dehydrokawaine-soluble solvent may be one of these alone or a combination of two or more thereof.

From the viewpoint of extraction efficiency, safety and industrialization, the dehydrokawaine-soluble solvent is preferably water and lower alcohols, more preferably water, ethanol and methanol, still more preferably water and ethanol, and hydrous ethanol which is a mixed solvent of water and ethanol. is even more preferred.

When hydrous ethanol is used as the dehydrokawaine-soluble solvent, the content of ethanol is preferably 20 vol% to 100 vol%, and from the viewpoint of good extraction efficiency, safety and industrialization, 30 vol% to 90 vol% is more preferable, and 40 vol% to 80 vol%. % is more preferred, and 50 vol % to 70 vol % is even more preferred. However, if the ethanol content in the hydrous ethanol is less than 20 vol %, it may be difficult to efficiently extract dehydrokawaine.

The extraction conditions are not particularly limited as long as the conditions are suitable for the dehydrokawaine in the dried shell ginger to dissolve in the solvent. The type and amount of dehydrokawaine-soluble solvent can be set as appropriate. For example, the dried shell ginger is immersed in a dehydrokawaine-soluble solvent of up to 10 times the volume for a predetermined period of time. In such an extraction operation, stirring operation, heating, etc. may be performed as necessary in order to increase the extraction efficiency.

As specific conditions for the extraction process, put 50 vol% to 70 vol% of water-containing ethanol, which is 3 to 10 times the volume of the dried shell ginger and the dried shell ginger, in a container, and the temperature is 10 ° C to 40 ° C. , preferably at room temperature (20° C. to 30° C.) for several hours to several days, preferably 12 hours to 10 days, by standing or stirring, but not limited thereto.

An extract and an extraction residue can be obtained by subjecting the dried shell ginger to the extraction treatment described above. By performing the solid-liquid separation process after the extraction process, the extraction liquid and the extraction residue can be efficiently separated. The solid-liquid separation means is not particularly limited, but for example, known solid-liquid separation means such as filtration and centrifugation can be used.

When an organic solvent is used as the dehydrokawaine-soluble solvent, the extract is preferably subjected to concentration treatment for the purpose of volatilizing the organic solvent. The concentration treatment is not particularly limited as long as it is a commonly known treatment for removing the organic solvent and further reducing the volume of the liquid. Freeze-drying and the like can be mentioned. The degree of concentration is not particularly limited. You may let

The extraction process may be performed once, but in order to increase the recovery rate of DDK and/or DK, the extraction process is preferably performed twice or more. From the viewpoint of workload and economy, the extraction process is performed twice. more preferably times. For example, the dried shell ginger is subjected to the first extraction treatment to obtain the first extract and the first extraction residue, and then the obtained first extraction residue is subjected to the second extraction treatment, Obtaining a second extract and a second extraction residue may be performed as step (1).

When the extraction process is performed twice or more, each extraction process may be performed under the same conditions or under different conditions. The extracts obtained in each extraction treatment can be collectively used in the next step as one crude extract of shell ginger. When the extract is subjected to solid-liquid separation treatment and / or concentration treatment, each extract may be subjected to solid-liquid separation treatment and / or concentration treatment, and each extract is combined and subjected to solid-liquid separation treatment and / or concentration treatment. /or may be subjected to a concentration treatment.

As described above, by subjecting the dried shell ginger to the extraction treatment, preferably by subjecting it to two or more extraction treatments, more preferably after two extraction treatments, each extract is subjected to solid-liquid separation treatment and concentration. A crude extract of Alpinia speciosa is obtained by subjecting to processing and summarizing.

The content of dehydrokawaine in the shell ginger crude extract is not particularly limited, but for example, it is preferably 0.1% by mass or more, more preferably 0.5% by mass or more, and 1.0% by mass or more. and even more preferably 2.0% by mass or more.

In step (2), the shell ginger crude extract obtained in step (1) is subjected to hydrolysis and alkali treatment to obtain a shell ginger extract. By subjecting the crude extract of shell ginger to hydrolysis and alkali treatment, contaminant components such as water-soluble components and fatty acids in the crude extract of shell ginger are removed, and dehydrokawaine is added as an insoluble matter (precipitate) at a high concentration. It is possible to obtain the shell ginger extract containing in.

The hydration treatment is not particularly limited as long as it is a condition in which water is added to the crude extract of shell ginger. It can be carried out by contacting a crude extract of Alpinia alba with a volume of water, more preferably 4 to 10 times the volume of water, more preferably 6 to 8 times the volume of water. The temperature and time at this time are not particularly limited.

Alkaline treatment is not particularly limited as long as it is carried out under conditions that can decompose impurities in the crude extract of shell ginger and further precipitate dehydrokawaine as an insoluble component. The aqueous solution can be stirred and/or allowed to stand at 10° C. to 30° C., preferably room temperature, for several hours to several days.

The alkali component used in the alkali treatment is not particularly limited as long as it decomposes contaminants in the crude extract of shell ginger and does not dissolve dehydrokawaine, for example, sodium hydroxide, potassium hydroxide, hydroxide Calcium and the like can be mentioned, but sodium hydroxide is preferred because it is a strong alkali and is economical.

The amount of the alkali component used in the alkali treatment is not particularly limited as long as it is an amount capable of precipitating dehydrokawaine. For example, if the alkali component is sodium hydroxide, the final concentration is from 0.1% (w/v). 10% (w/v), preferably 0.5% (w/v) to 8% (w/v), more preferably 0.5% (w/v) to 6% (w/v) such amount. The amount of the alkaline component used in the alkaline treatment is preferably such that the pH becomes alkaline, preferably 12 to 14, and more preferably around 14, using pH as an index.

In step (2), hydrolysis and alkali treatment may be carried out simultaneously by using an aqueous alkali solution. For example, after adding the crude extract of shell ginger to an aqueous solution of sodium hydroxide dissolved in water, the amount of water is adjusted to be 5 to 10 times the volume of the crude extract of shell ginger, Stir at 10° C. to 30° C., preferably at room temperature, for several hours to several days, preferably for 1 hour to 24 hours, then allow to stand for several hours to several days, preferably for 10 hours to 7 days. can implement step (2). .

In the step (2)', salting out is carried out in addition to the water treatment and the alkali treatment. Dehydrokawaine can be efficiently precipitated by salting out. Salting out is not particularly limited as long as it is carried out under conditions that can precipitate dehydrokawaine. For example, an aqueous solution containing the crude extract of shell ginger and salts is heated at 10 ° C. to 30 ° C., preferably at room temperature for several hours to several hours. It can be carried out by stirring and/or standing still for days.

Salts used for salting out are not particularly limited as long as they are water-soluble substances with higher hydration power than dehydrokawaine. Examples include organic salts and inorganic salts. , sucrose, and maltose, and more preferably glucose.

The amount of salt used for salting out is not particularly limited as long as it is an amount that allows dehydrokawaine to precipitate as a solid content. For example, if the salt is glucose, the final concentration is 0.1% (w / v). ~10% (w/v), preferably 0.5% (w/v) to 5% (w/v), more preferably 0.5% (w/v) to 2% (w/v) It is an amount that becomes

In step (2)', hydrolysis, alkali treatment and salting out may be performed sequentially, or two or three of these treatments may be performed simultaneously. For example, after adding the crude extract of shell ginger to an aqueous solution of sodium hydroxide and salts dissolved in water, the amount of water is adjusted to be 5 to 10 times the volume of the crude extract of shell ginger. at 10° C. to 30° C., preferably room temperature, and stirred for several hours to several days, preferably for 1 hour to 24 hours, then allowed to stand for several hours to several days, preferably for 10 hours to 7 days. By doing so, step (2)' can be carried out.

Steps (2) and (2)' can be performed once to obtain an extract containing dehydrokawaine of high purity without being performed multiple times, but even if performed multiple times good. The shell ginger extract can be obtained as a precipitate, in solid form, specifically in powder form. By subjecting the aqueous solution containing the obtained powdery Alpinia speciosa extract to solid-liquid separation treatment and/or drying treatment, the powdery Alpinia speciosa extract can be efficiently recovered. It is preferable to wash the shell ginger extract with water or the like, for example, when it is used as a raw material for an oral composition or a composition for external use.

The content of dehydrokawaine in the shell ginger extract obtained by the method of one aspect of the present invention is not particularly limited, but for example, it is preferably 70 wt% or more, preferably 80 wt% or more, based on the dry mass of the shell ginger extract. is more preferably 90 wt % or more, and even more preferably 95 wt % or more. In addition, the recovery rate of dehydrokawaine in the shell ginger extract is, for example, preferably 30% or more, more preferably 40% or more, relative to the content of dehydrokawaine in the shell ginger crude extract, It is more preferably 80% or more, and even more preferably 90% or more. Although the upper limits of these are not particularly limited, they are typically 100 wt% and 100%, respectively.

The contents of DDK and DK differ depending on the part of shell ginger. When shell ginger flowers are used, shell ginger extract containing both DDK and DK tends to be obtained, and when shell shell leaves are used, shell ginger extract containing DDK tends to be obtained.

When the shell ginger flower is used, the content of DDK in the shell ginger extract is, for example, preferably 60 wt% or more, more preferably 70 wt% or more, based on the dry mass of the shell ginger extract. , 80 wt % or more. In this case, the recovery rate of DDK in the shell ginger extract is, for example, preferably 30% or more, more preferably 40% or more, relative to the content of DDK in the shell ginger crude extract. , is more preferably 80% or more, and even more preferably 90% or more. Although the upper limits of these are not particularly limited, they are typically 100 wt% and 100%, respectively.

When the shell ginger flower is used, the content of DK in the shell ginger extract is, for example, preferably 5 wt% or more, more preferably 10 wt% or more, based on the dry mass of the shell ginger extract. , 12 wt % or more. In this case, the recovery rate of DK in the shell ginger extract is, for example, preferably 10% or more, more preferably 20% or more, relative to the DK content in the shell ginger crude extract. , is more preferably 40% or more, and even more preferably 60% or more. Although the upper limits of these are not particularly limited, they are typically 100 wt% and 100%, respectively.

When shell ginger leaves are used, the content of DDK in the shell ginger extract is, for example, preferably 60 wt% or more, more preferably 70 wt% or more, based on the dry mass of the shell ginger extract. , more preferably 80 wt % or more, and even more preferably 90 wt % or more. In this case, the recovery rate of DDK in the shell ginger extract is, for example, preferably 30% or more, more preferably 40% or more, relative to the content of DDK in the shell ginger crude extract. , is more preferably 80% or more, and even more preferably 90% or more. Although the upper limits of these are not particularly limited, they are typically 100 wt% and 100%, respectively. In this case, the content of DK in the shell ginger extract is 1 wt % or less.

Dehydrokawaine contained in the shell ginger extract can be confirmed and quantified by high performance liquid chromatography (HPLC) described in the examples below.

In the method of one aspect of the present invention, various steps and operations can be added before, after, or during the above steps as long as the problems of the present invention can be solved.

Hereinafter, as a specific embodiment of the present invention, a method for producing a shell ginger extract containing dehydrokawaine using dried shell ginger flowers as a raw material will be described. not limited to

The flowers of Alpinia speciosa collected around the time of flowering (May to July) are subjected to a low-temperature vacuum drying treatment to dry to a moisture content of 10% or less. A predetermined amount of the dried shell ginger is added to 50 vol% to 70 vol% water-containing ethanol that is 3 to 10 times the volume of the dried shell ginger, and allowed to stand at room temperature for 12 hours to 10 days for extraction. After removing the residue of shell ginger by filtering the obtained extract, the obtained filtrate is subjected to vacuum concentration to obtain a first crude extract of shell ginger. Further, the same extraction treatment is performed on the shell ginger residue to obtain a second crude extract of shell ginger. The first crude extract of shell ginger and the second crude extract of shell ginger are mixed and used in the following steps.

Next, an aqueous solution of sodium hydroxide and glucose dissolved in the obtained crude extract of Alpinia speciosa is added, and water is added so that the volume is 5 to 10 times the volume of the crude extract of Alpinia speciosa. The final concentration of sodium hydroxide in the resulting aqueous solution is 0.5% (w/v) to 6% (w/v) and the final concentration of glucose is 0.5% (w/v) to 2% (w/v). w/v). Next, the obtained aqueous solution is stirred at room temperature for 1 hour to 24 hours and then allowed to stand still for 10 hours to 5 days to obtain an extract of shell ginger as a precipitate. A powdery Alpinia speciosa extract is obtained by subjecting the obtained Alpinia speciosa extract to a filtration treatment and a freeze-drying treatment. The content of dehydrokawaine in the obtained Alpinia shell extract can be 90 wt % or more based on the dry mass of the Alpinia shell extract.

A shell ginger extract produced by the method of one aspect of the present invention can be included in the present invention as another aspect. The extract of Alpinia speciosa of the present invention is characterized in that the total content of DDK and/or DK is a predetermined amount, and the contained DDK and/or DK is derived from Alpinia alba, which is the raw material.

In the Alpinia speciosa extract of one embodiment of the present invention, the total content of DDK and DK is, for example, 80 wt% or more, preferably 90 wt% or more, and more preferably 95 wt% or more. The upper limit of the content is not particularly limited, and is typically 100 wt%.

In the shell ginger extract of one embodiment of the present invention, the content of DDK is preferably 70 wt% or more, more preferably 80 wt% or more, and 90 wt% or more, based on the dry mass of the shell ginger extract. It is even more preferable to have The Alpinia speciosa extract of one embodiment of the present invention has a DK content of preferably 5 wt% or more, more preferably 10 wt% or more, and 12 wt% or more based on the dry mass of the Alpinia speciosa extract. It is even more preferable to have However, although the shell ginger extract of one embodiment of the present invention preferably contains both DDK and DK, it may contain either one of DDK and DK.

The DDK and DK contained in the shell ginger extract of one embodiment of the present invention are characterized in that both of them are derived from the raw material, shell ginger. In other words, the shell ginger extract of one embodiment of the present invention is characterized in that it does not contain DDKs and DKs obtained by extraction or synthesis of natural products other than shell ginger.

Applications of the Alpinia speciosa extract of one embodiment of the present invention are not particularly limited. It can be used as a raw material for a product or the composition itself.

The present invention will be described in more detail below with reference to Examples, but the present invention is not limited to these Examples, and the present invention can take various aspects as long as the problems of the present invention can be solved. .

[Quantification of shell ginger extract]
The content (mg) of dihydro-5,6-dehydrokawaine (DDK) and 5,6-dehydrokawaine (DK) was determined by HPLC using a COSMOSIL 5C18-AR-2 column as a column and MeOH as a mobile phase. : H ₂ O = 60:40 to 100:0, the flow rate is 1 ml/min, DDK is set to a measurement wavelength of 278.0 nm for about 12 minutes, and DK is set to a measurement wavelength of 318 nm for about 17 minutes. was determined by the calibration curve method as a peak with a retention time of .

[Example 1. Production of high-purity shell ginger extract using shell ginger as raw material (1)]
As Example 1, a 100 g scale, sodium hydroxide 4% (w / v), glucose 1% (w / v) system was carried out. The illustrated flow diagram is shown in FIG.

The Alpinia speciosa was subjected to a low-temperature vacuum drying treatment at 40° C. for 5 hours to obtain dried flowers (water content: 3% to 8%). 100.0 g of dried flowers are placed in 500 mL of 60% (v / v) water-containing ethanol, subjected to ethanol extraction treatment by standing at room temperature for 1 day, and then subjected to filtration treatment using a filter (pore size 5 μm). , 224.1 g of filtrate (1) and 325.9 g of filtration residue (1) were obtained. The whole amount of filtrate (1) was subjected to vacuum concentration treatment to obtain 7 g of crude extract (1) as the first extract. DDK in crude extract (1) was 448.6 mg and DK was 120.3 mg.

In addition, the filtration residue (1) is placed in 500 mL of 60% (v/v) aqueous ethanol, subjected to ethanol extraction treatment by standing at room temperature for 1 day, and then subjected to filtration treatment using a filter (pore size 5 μm). Thus, 467.1 g of filtrate (2) was obtained. The whole amount of filtrate (2) was subjected to vacuum concentration treatment to obtain 6 g of crude extract (2) as the second extract. DDK in crude extract (2) was 375.5 mg and DK was 105.4 mg.

An aqueous solution containing 4.0 g of sodium hydroxide and 1.0 g of glucose was added to the crude extract (1+2) obtained by combining the crude extract (1) and the crude extract (2), and further water was added. An aqueous solution (pH 14) with a total volume of 100 mL was stirred at room temperature for 5 hours (150 rpm), then subjected to alkaline treatment and salting out by standing for 19 hours, and then centrifuged (2600 x g, 4,000 rpm, 1 minute), and the resulting precipitate was subjected to a freeze-drying treatment to obtain 1,012.6 mg of a powdery Alpinia speciosa extract.

The obtained extract of Alpinia speciosa contained 843.5 mg of DDK (83.3% purity) and 155.3 mg of DK (15.3% purity). Also, based on the amounts of DDK and DK contained in the crude extract (1+2), the recovery rate of DDK in the shell ginger extract was 103% and the recovery rate of DK was 70%.

[Example 2. Production of high-purity shell ginger extract using shell ginger as a raw material (2)]
As Example 2, 38.0 kg scale, sodium hydroxide 4% (w / v), glucose 1% (w / v) of the method for producing a high-purity shell ginger extract using shell ginger as a raw material An overview flow diagram is shown in FIG.

The Alpinia speciosa was subjected to a low-temperature vacuum drying treatment at 40° C. for 5 hours to obtain dried flowers (water content: 3% to 8%). 38.0 kg of dried flowers are placed in 180 L of 60% (v / v) water-containing ethanol, subjected to ethanol extraction treatment by standing at room temperature for 7 days, and then subjected to filtration treatment using a filter (pore size 20 μm). , about 120 L of filtrate (1) and filtration residue (1) were obtained. The whole amount of the filtrate (1) was subjected to low-temperature vacuum drying treatment at 40° C. for 5 hours to obtain crude extract (1) as the first extract. DDK in crude extract (1) was 200 g and DK was 62 g.

In addition, the filtration residue (1) is placed in 180 L of 60% (v/v) water-containing ethanol, subjected to ethanol extraction treatment by standing at room temperature for 7 days, and then subjected to filtration treatment using a filter (pore size 20 μm). Thus, about 150 L of filtrate (2) was obtained. The whole amount of the filtrate (2) was subjected to a low-temperature vacuum drying treatment at 40° C. for 6 hours to obtain a crude extract (2) as a second extract. DDK in crude extract (2) was 87 g and DK was 27 g.

Crude extract (1+2), which was the total amount of crude extract (1) and crude extract (2) combined, was subjected to low temperature vacuum drying treatment.

An aqueous solution containing 1.5 kg of sodium hydroxide and 350 g of glucose was added to the extract (1+2), and further water was added to bring the total volume to 38 L. The aqueous solution (pH 14) was stirred at room temperature (150 rpm) for 15 hours. Then, subjected to alkaline treatment to stand still for 3 days, then subjected to centrifugal treatment (2600 × g, 4,000 rpm, 10 minutes), and subjecting the obtained precipitate to freeze-drying treatment to obtain powdered shell ginger. 189.5 g of extract were obtained.

The obtained extract of Alpinia speciosa contained 134.5 g of DDK (71.0% purity) and 25.9 g of DK (13.7% purity). Also, based on the amounts of DDK and DK contained in the crude extract (1+2), the recovery rate of DDK in the extract of shell ginger was 47%, and the recovery rate of DK was 29%.

[Example 3. Production of high-purity shell ginger extract using shell ginger as a raw material (3)]
As Example 3, a flow chart showing an outline of a method for producing a high-purity shell ginger extract using shell ginger as a raw material, which was performed in a 100 g scale, sodium hydroxide 1% (w / v), glucose-free system. It is shown in FIG.

The Alpinia speciosa was subjected to a low-temperature vacuum drying treatment at 40° C. for 5 hours to obtain dried flowers (water content: 3% to 8%). 100.0 g of dried flowers are placed in 500 mL of 60% (v / v) water-containing ethanol, subjected to ethanol extraction treatment by standing at room temperature for 1 day, and then subjected to filtration treatment using a filter (pore size 5 μm). , filtrate (1) and filtration residue (1) were obtained.

The filtration residue (1) is placed in 500 mL of 60% (v / v) aqueous ethanol, subjected to ethanol extraction treatment by standing at room temperature for 1 day, and then subjected to filtration treatment using a filter (pore size 5 μm). , to obtain a filtrate (2).

714.9 g of filtrate (1+2), which is a combination of filtrate (1) and filtrate (2), was subjected to concentration under reduced pressure to obtain 13 g of crude extract (1+2). DDK in the crude extract (1+2) was 838.9 mg and DK was 252.3 mg.

An aqueous solution containing 1.0 g of sodium hydroxide was added to the obtained crude extract (1+2), and further water was added to bring the total volume to 100 mL. The aqueous solution (pH 10) was stirred at room temperature for 5 hours (150 rpm). Then, it is subjected to alkaline treatment by standing still for 19 hours, then subjected to centrifugal treatment (2600 x g, 4,000 rpm, 1 minute), and the obtained precipitate is subjected to freeze-drying treatment to obtain a powdery moon. 1265.9 mg of peach extract was obtained.

The obtained extract of Alpinia speciosa contained DDK 939.7 mg (purity 74.2%) and DK 190.9 mg (purity 15.1%). Also, based on the amount of DDK and DK contained in the crude extract (1+2), the recovery rate of DDK in the shell ginger extract was 112% and the recovery rate of DK was 76%.

[Example 4. Production of high-purity shell ginger extract using shell ginger leaves as raw material]
As Example 4, an overview of the method for producing a high-purity shell ginger extract using shell ginger leaves as a raw material, which was performed in a 100 g scale, sodium hydroxide 4% (w / v), glucose 1% (w / v) system. The illustrated flow diagram is shown in FIG.

Shell ginger leaves were subjected to a heat drying treatment to obtain dried leaves. 100.0 g of dried leaves are placed in 600 mL of 60% (v / v) water-containing ethanol, subjected to ethanol extraction treatment by standing at room temperature for 4 days, and then subjected to filtration treatment using a filter (pore size 5 μm). , 282.7 g of filtrate (1) and 357.3 g of filtration residue (1) were obtained. The whole amount of filtrate (1) was subjected to vacuum concentration treatment to obtain crude extract (1) as the first extract. DDK in crude extract (1) was 227.5 mg, but DK was below the lower limit of detection.

In addition, the filtration residue (1) is placed in 600 mL of 60% (v/v) aqueous ethanol, subjected to ethanol extraction treatment by standing at room temperature for 3 days, and then subjected to filtration treatment using a filter (pore size 5 μm). Thus, 448.6 g of filtrate (2) was obtained. The whole amount of the filtrate (2) was subjected to concentration under reduced pressure to obtain a crude extract (2) as a second extract. DDK in crude extract (2) was 150.8 mg, but DK was below the lower limit of detection.

An aqueous solution of 4.0 g of sodium hydroxide and 1.0 g of glucose was added to the extract (1+2), which was the total amount of the crude extract (1) and the crude extract (2), and the total volume was adjusted to 100 mL. The aqueous solution (pH 14) obtained by adding water to is stirred at room temperature for 5 hours (150 rpm), then subjected to alkali treatment by standing for 19 hours, and then centrifuged (2600 x g, 4,000 rpm, 1 minute), and the resulting precipitate was subjected to a freeze-drying treatment to obtain 352.8 mg of a powdery Alpinia speciosa extract.

The obtained extract of Alpinia speciosa contained 349.3 mg of DDK (purity 99.0%). Also, based on the amount of DDK contained in the crude extract (1+2), the recovery rate of DDK in the shell ginger extract was 82%.

The Alpinia speciosa extract produced by the method of one aspect of the present invention contains dihydro-5,6-dehydrokawaine and 5,6-dehydrokawaine at high purity, and is expected to have these pharmacological effects. It can be used for foods and beverages, cosmetics, pharmaceuticals, quasi-drugs, etc., and is particularly useful as oral preparations, external preparations, injections, lotions, etc., and can be blended therein.

Claims (11)

A step of obtaining a crude extract of shell ginger by subjecting the shell ginger dried material to an extraction treatment using a dehydrokawaine-soluble solvent;
A method for producing an Alpinia speciosa extract, comprising a step of subjecting an Alpinia speciosa crude extract to hydrolysis and alkali treatment to obtain an Alpinia speciosa extract. A step of obtaining a crude extract of shell ginger by subjecting the shell ginger dried material to an extraction treatment using a dehydrokawaine-soluble solvent;
A method for producing an shell ginger extract, comprising a step of subjecting a shell core crude extract to hydrolysis, alkali treatment and salting out to obtain the shell ginger extract. 3. Any one of claims 1 and 2, wherein the crude extract of Alpinia speciosa is obtained by subjecting the liquid extract obtained by the extraction process to solid-liquid separation and/or concentration treatment. The method described in . The method according to any one of claims 2 and 3, wherein the salting out is salting out using at least one saccharide selected from the group consisting of glucose, sucrose and maltose. The method according to any one of claims 1 to 4, wherein the dehydrokawaine-soluble solvent is 30% (v/v) to 90% (v/v) hydrous ethanol. The alkali treatment according to any one of claims 1 to 5, wherein the alkali treatment is alkali treatment using sodium hydroxide with a final concentration of 0.5% (w/v) to 6% (w/v). the method of. 7. The extract according to any one of claims 1 to 6, wherein the total content of dihydro-5,6-dehydrokawaine and 5,6-dehydrokawaine is 80% (w/w) or more. the method of. The shell ginger extract has a dihydro-5,6-dehydrokawaine content of 70% (w/w) or more and/or a 5,6-dehydrokawaine content of 10% (w/w) The method according to any one of claims 1 to 7, which is the above. The method according to any one of claims 1 to 8, wherein the shell ginger extract is a solid shell ginger extract. The total content of dihydro-5,6-dehydrokawaine and 5,6-dehydrokawaine is 80% (w/w) or more, and dihydro-5,6-dehydrokawaine and 5,6-dehydrokawaine are shell ginger Getto extract derived from. The shell ginger extract has a dihydro-5,6-dehydrokawaine content of 80% (w/w) or more and/or a 5,6-dehydrokawaine content of 10% (w/w) The shell ginger extract according to claim 10, which is above.

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