JPH10287695A - Production of sesaminol triglucoside - Google Patents

Abstract

PROBLEM TO BE SOLVED: To industrially and advantageously produce a sesaminol triglucoside useful as a material, etc., for foods, medicines, cosmetics, etc., by extracting a solvent-soluble ingredient from defatted sesame seeds with water, (aqueous) ethanol, etc., then treating the resultant extract solution with active carbon and collecting an adsorbed ingredient. SOLUTION: A solvent-soluble ingredient containing the sesaminol triglucoside is extracted from defatted sesame seeds with a solvent such as water, ethanol or an aqueous ethanol, and the resultant extract solution is then brought into contact with active carbon to adsorb a part of the solvent-soluble ingredient on the active carbon. The active carbon adsorbing the part of the solvent-soluble ingredient is subsequently brought into contact with an aqueous ethanol at >=40 vol.% ethanol concentration or water and >=40 deg.C and washed. The prepared active carbon is then brought into contact with an aqueous ethanol at 50-98 vol.% ethanol concentration and >=40 deg.C to desorb and elute the sesaminol triglucoside. The eluted substance is further collected from the eluate to simply produce the objective high-purity sesaminol triglucoside useful as a material for foods, medicines, cosmetics, etc., at a high recovery ratio.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to a method for easily producing sesaminol triglucoside useful as a material for foods, medicines, cosmetics, etc. from defatted sesame seeds with high purity and high recovery.

[0002]

2. Description of the Related Art As a method for separating sesameol glycosides from defatted sesame seeds, 1) extracting defatted sesame seeds using 80% ethanol water, and extracting the extract with a vinyl aromatic hydrocarbon polymer Method of separating sesaminol triglucoside by desorbing and eluting the adsorbate with an aqueous methanol solution after performing an adsorption treatment using a polymer-based adsorbent (Phytochemistry, vol. 35, 3)
No. 773-776), 2) Extraction of defatted sesame seeds with a polar organic solvent or a mixed solvent of a polar organic solvent and water, and fractionation of the extract, followed by fractionation of the solvent Is further fractionated by silica gel chromatography to separate sesaminol triglucoside (JP-A-62-2).
38287) has been proposed. However, 1) and
The conventional method of 2) requires solvent fractionation before adsorbing sesaminol triglucoside on the adsorbent,
There is a disadvantage that the purification operation is complicated, and there is a disadvantage that an organic solvent that cannot be used for food is used in the separation operation. Furthermore, the adsorbents used in the methods 1) and 2) are relatively expensive, and require a large amount because the amount of adsorbed sesaminol triglucoside is small. Sesameol monoglucoside, sesaminol diglucoside as sesaminol glycosides in sesame seeds,
There are sesaminol triglucoside and the like, and these sesaminol glycosides are known to have various physiologically active effects in biological systems, in addition to a hydroxyl radical scavenging effect and a lipid peroxidation inhibitory effect. Of the sesaminol glycosides, sesaminol triglucoside, which has relatively high water solubility, is expected to be used as a material for foods, pharmaceuticals, cosmetics, etc., utilizing its physiological activity, and therefore it can be efficiently separated from sesame seeds. It is strongly desired to establish an industrial production method that can be manufactured at low cost.

[0003]

The problem to be solved by the present invention is to produce a high-purity sesaminol glycoside using only an organic solvent that can be used in foods, which is simpler and less expensive than the conventional method. It is about establishing a way to do it. In addition, even when using defatted defatted sesame seeds as a raw material for extracting sesaminol triglucoside, there is no burnt smell or burnt color remaining in the product, and a method for producing a highly transparent, visually pleasing product is developed. It is in.

[0004]

Means for Solving the Problems As a result of research conducted to solve the above conventional problems, the present inventors have found that activated carbon adsorbs sesaminol triglucoside dissolved in an extract much more than other adsorbents. After washing with a specific solvent, a specific condition for desorbing and eluting and recovering sesaminol triglucoside with a specific solvent was found.

[0005] That is, the present invention provides (1) a solvent-soluble component containing sesaminol triglucoside extracted from defatted sesame seeds using a solvent selected from water, ethanol or ethanol water, and the resulting extract is obtained. Contacting the activated carbon with activated carbon to cause a part of the solvent-soluble component to be adsorbed to the activated carbon, and then collecting sesaminol triglucoside from the adsorbed component, (2) activated carbon (1) The method for producing sesaminol triglucoside according to (1), wherein the process of collecting sesaminol triglucoside from the component adsorbed on the first step is as follows. By contacting with ethanol water or water having an ethanol concentration of 40% by volume or less,
A step of washing the activated carbon to which a part of the solvent-soluble component is adsorbed, a second step: the activated carbon washed in the first step and ethanol water having an ethanol concentration in the range of 50 to 98% by volume,
A step of desorbing and eluting sesaminol triglucoside by contacting under conditions of 40 ° C. or more to obtain ethanol water in which sesaminol triglucoside is dissolved (3) In the first step, the ethanol water has an ethanol concentration of 10 to 40% by volume. (2) The method for producing sesaminol triglucoside according to (2), wherein in the second step, ethanol water has an ethanol concentration of 55 to 75% by volume, (5)
The second step relates to the method for producing sesaminol triglucoside according to (2), wherein the contacting is performed at a temperature from 50 ° C. to the boiling point of the ethanol water.

[0006] The present invention does not limit the state of sesame seed, which is a raw material used for extracting sesaminol triglucoside, or the extraction method for obtaining a solution containing sesaminol triglucoside. The sesame seeds used as raw materials are in a state without treatment, peeled, roasted,
What is obtained when processing such as pulverization, hexane degreasing, and oil pressing by pressing alone or in combination can also be used. Extraction methods include immersion, stirring,
Conventional methods such as heating or pressurization can be used alone or in combination. For the extraction, a solvent consisting of at least one selected from ethanol and water is used, but when using defatted sesame seeds as a raw material, it is preferably used at 50 ° C or higher, preferably at 70 ° C or higher, and hot water at 80 ° C or higher. The use of is particularly efficient and preferred. In addition, when 50% by volume or less of ethanol water or water is used as the solvent, regardless of the temperature conditions at the time of adsorption of sesaminol triglucoside to activated carbon, the extract is continuously prepared without dilution or the like. Can be offered.

[0007] In the present invention, an extract containing sesaminol triglucoside is brought into contact with activated carbon to adsorb adsorbed components containing sesaminol triglucoside contained in the extract. The present invention does not limit the type of activated carbon to be used. Examples thereof include 1) those derived from wood, 2) those derived from coconut shells, and 3) those derived from coal. Can also be suitably used. Further, in the present invention, the specific surface area and pore volume of the activated carbon are not limited, but the pores of the activated carbon are preferably large, and the pore volume of 10 ° or more is 0.4 ml /
It is desirable to have more than g.

In the present invention, the activated carbon is contacted with
There is no particular restriction on the ethanol concentration or temperature in the extract,
When sesaminol triglucoside is adsorbed on activated carbon, the contact temperature must be 40 ° C or higher and 0 to 40% by volume or 9%.
A range of 8 to 100% by volume is desirable. In low-concentration ethanol water, sesaminol triglucoside is more efficient at higher temperatures because it takes less time to adsorb to activated carbon. On the other hand, depending on the properties and amount of activated carbon used, sesaminol triglucoside is 50-98% by volume.
It is difficult to adsorb to activated carbon in ethanol water, and it was found to be convenient when desorbing and eluting sesaminol triglycoside from activated carbon. When contacting at a temperature of 60 ° C or higher, there is a possibility that 60% by weight or more will not be adsorbed. From this, in order to shorten the time required for adsorption and to adsorb a large amount of sesaminol triglucoside to activated carbon, when the ethanol concentration in the extract is high, it is necessary to remove ethanol or dilute with water. By means, it is more efficient to prepare the extract so that the ethanol concentration is preferably 40% by volume or less, more preferably 20% by volume or less, and then perform the adsorption treatment at a high temperature of 40 ° C. or more.

In the present invention, the amount of sesaminol triglucoside relative to the activated carbon or the amount of defatted sesame seeds as an extraction raw material is not limited, but usually, 4 parts by weight of sesaminol triglucoside or 1,000 parts by weight of defatted sesame seeds. Activated carbon is 10 to 150 parts by weight, preferably 30 to 100 parts by weight. In the present invention, as a method of bringing the extract into contact with activated carbon, stirring, heating, pressurization, conventional methods such as passing through a column may be mentioned, and as a method of separating the extract from the activated carbon, filtration, centrifugation, etc. Conventional methods are mentioned, and they can be used in combination. For example, 1) a method in which an extract of defatted sesame seeds is passed through a column filled with activated carbon under normal pressure or pressure, and 2) an activated carbon is added to the extract of defatted sesame seeds and stirred, and then the activated carbon is separated. And the like. Above all, a method in which activated carbon is packed into a column is preferable, and sesaminol triglucoside contained in an extract of defatted sesame seed can be efficiently adsorbed on activated carbon.

In the present invention, the time for contacting the extract containing sesaminol triglucoside with the activated carbon is not particularly limited. However, if the contact time is shorter than an appropriate time, the sesaminol triglucoside in the extract may be reduced. Is not completely adsorbed on activated carbon. This time is adjusted by the concentration and temperature of the extract containing sesaminol triglucoside, the amount of activated carbon, and the like. For example, with respect to 1200 parts by volume of a water extract containing 0.75 parts by weight of sesaminol triglucoside, when contacted with 9 parts by weight of activated carbon at a temperature of 100 ° C. while refluxing, the contact time is preferably 45 minutes or more, more preferably 1.5 hours. That is all.

In the present invention, the activated carbon can be packed in a column and used. Although the present invention does not limit the flow rate in the column at that time, if the extract is allowed to flow faster than an appropriate speed, sesaminol triglucoside in the extract will not be completely adsorbed on the activated carbon. This rate will be adjusted according to the concentration of the extract containing sesaminol triglucoside, the column temperature, the amount of activated carbon corresponding thereto, for example, 1200 parts by volume of a water extract containing 0.75 parts by weight of sesaminol triglucoside, Column temperature 60 ° C, activated carbon 9 parts by weight (60
When the liquid is passed through a column having a length of 33 with respect to an inner diameter of 1.5 and filled therein, the flow rate in the column is preferably 10 parts by volume / minute or less, more preferably 5 parts by volume / minute or less.

In the first step of the present invention, the activated carbon, to which the adsorbed component containing sesaminol triglucoside has been adsorbed as described above, is washed with ethanol water or water. In the present invention, the amount of water or ethanol water to be brought into contact with the activated carbon in the first step is not particularly limited, but the temperature at the time of contact is 40 ° C. or more and the ethanol concentration in the ethanol water is 40% by volume or less. In this case, the contact temperature is preferably 60 ° C. or more, and the ethanol concentration in ethanol water is 10 to 20% by volume. The higher the contact temperature in the first step, the higher the washing effect. However, when the concentration of ethanol water used is 50 to 98% by volume and 40 ° C. or more, the sesaminol triad adsorbed on activated carbon is used. Glucoside elutes in large quantities. In general, sesaminol triglucoside varies depending on the properties and amount of activated carbon used. However, when ethanol water having a concentration of 50 to 98% by volume of ethanol at 40 ° C or higher is used, sesaminol triglucoside adsorbed on activated carbon is desorbed. It is eluted, especially when contacted under high temperature conditions of 60 ° C or higher, although the amount of sesaminol triglucoside at the time of recovery in the subsequent second step is greatly reduced, depending on the liquid volume, and sesaminol triglucoside is greatly reduced. Glucosides cannot be obtained with high recovery and high purity.

In the first step of the present invention, there is no particular limitation on the time for contacting the activated carbon adsorbed with the adsorbent containing sesaminol triglucoside with ethanol water or water, but the contact time is shorter than the appropriate time. If so, it cannot be sufficiently washed. The contacting time is adjusted according to the contacting temperature, the amount of activated carbon, the concentration and amount of ethanol water, etc., for example, while stirring 9 parts by weight of activated carbon adsorbing the adsorption component at a temperature of 60 ° C. When contacting with 180 parts by volume of 20% by volume of ethanol water, the contacting time is preferably 20 minutes or more, more preferably 1 hour or more.

In the first step of the present invention, the activated carbon can be packed in a column and used. The present invention does not limit the flow rate in the column at that time, but if the flow rate is higher than an appropriate flow rate, the washing becomes insufficient.
The appropriate flow rate in the column is adjusted by the temperature, the amount of activated carbon, the amount of ethanol water or water, and the like. For example, at a column temperature of 60 ° C., 180 parts by volume of 20% by volume ethanol water are passed through a column having a length of 33 with respect to an inner diameter of 1.5 filled with 9 parts by weight (60 parts by volume) of activated carbon adsorbed with the adsorbed component without circulating. When the solution is liquid, the flow rate in the column is preferably 90 parts by volume / min or less, more preferably 30 parts by volume / min or less.

In the second step of the present invention, sesaminol triglucoside is desorbed and eluted from the activated carbon to which the adsorbed component obtained through the first step is adsorbed by using ethanol water, as described above, to convert sesaminol triglucoside. This is to obtain dissolved ethanol water. In the present invention, the content ratio of ethanol in ethanol water is 50 to 98% by volume, preferably 50 to 90% by volume, and more preferably 55 to 75% by volume. Further, in the present invention, the temperature at which the activated carbon is treated with ethanol water is set to 40 ° C. or higher. However, the temperature is preferably set to a temperature from 50 ° C. to the boiling point of ethanol water. Although the present invention does not limit the use ratio of ethanol water to the above-mentioned activated carbon part by weight, it is preferably 20 to 100 times, more preferably 30 to 60 times. It is uneconomical to use a proportion higher than this, since a corresponding effect cannot be obtained. However, the preferred ratio of ethanol water to activated carbon used here is the total amount of the amount used in the second step, and when ethanol is recovered by distillation or the like after contact with activated carbon and used repeatedly, the Not as long.

In the second step of the present invention, the time for eluting sesaminol triglucoside from the activated carbon to which the adsorbed component obtained through the first step has been adsorbed is not particularly limited, but the contact time shorter than the appropriate time is not limited. If the time is too long, sesaminol triglucoside adsorbed on activated carbon cannot be sufficiently desorbed and eluted. The contacting time is adjusted by the contacting temperature, the amount of activated carbon, the concentration and amount of ethanol water, and the like. For example, when refluxing 360 parts by volume of ethanol water of 60% by volume at a temperature of 80 ° C. and contacting with 9 parts by weight of activated carbon adsorbing the adsorbed component, the contact time is preferably 30 minutes or more, more preferably 40 minutes or more. .

In the second step of the present invention, similarly to the first step, activated carbon can be packed in a column and used. The present invention does not limit the flow rate in the column at that time, but if the flow rate is higher than an appropriate flow rate, sesaminol triglucoside adsorbed on activated carbon cannot be sufficiently desorbed and eluted and recovered. The appropriate flow rate in the column depends on the column temperature,
It is controlled by the amount of activated carbon, the concentration and amount of ethanol water relative thereto, and the like. For example, a column having a length of 33 with respect to an inner diameter of 1.5 filled with 9 parts by weight (60 parts by volume) of activated carbon adsorbing the adsorbed component at a column temperature of 60 ° C. is passed without circulating 360 parts by volume of 60% by volume ethanol water without circulation. When the solution is liquid, the flow rate in the column is preferably 5 parts by volume / minute or less, more preferably 2 parts by volume / minute or less.

The content of sesaminol triglucoside in the solid content obtained by removing ethanol and water from the ethanol water in which sesaminol triglucoside thus obtained is dissolved can be adjusted to a ratio of 20 to 70% by weight. Various forms of products can be obtained by appropriately performing post-treatment according to the purpose and use using ethanolic water in which sesaminol triglucoside obtained by the method of the present invention is dissolved. For example, 1) ethanol and water are distilled off to obtain a liquid product containing a high concentration of sesaminol triglucoside; 2) ethanol and water are almost completely distilled off to form sesaminol triglucoside. Examples include a solid product containing high purity, and 3) an example of adding a edible solid extender and drying to obtain a granular product or a powder product.

[0019]

DESCRIPTION OF THE PREFERRED EMBODIMENTS Embodiments of the present invention are as follows.
1) to 6) are preferred examples. 1) 100 ° C to 100 parts by weight of sesame seeds defatted with hexane
600 parts by weight of hot water is added and stirred, and 400 parts by weight of an extract containing 0.25 parts by weight of sesaminol triglucoside obtained by separating defatted sesame seeds is obtained. As activated carbon, granular activated carbon derived from wood (Nimura Chemical ( (Specific surface area 1050m2 / g, 1010)
The above extract was passed through a glass column filled with 8 parts by weight (53 parts by volume) of the above pore volume (1.03 ml / g) (insulated at 60 ° C, and thereafter the same) (the flow rate in the column was 1.1 parts by volume / minute). After that, the adsorption component containing sesaminol triglucoside is adsorbed on activated carbon, and then 30% by volume of ethanol is added to a glass column filled with the activated carbon in a wet state to which the adsorption component containing sesaminol triglucoside is adsorbed. First step of obtaining a washed wet activated carbon by passing 180 parts by volume of water, and adding 60% by volume ethanol water to the above glass column.
A second step of adding 360 parts by volume and passing the solution to obtain 360 parts by volume of ethanol water in which 0.07% by weight of sesaminol triglucoside was dissolved, which was dried to a purity of 62% by weight
Of sesaminol triglucoside can be obtained.

2) In the above 1), sesaminol triglucoside is extracted from the sesame seeds defatted by pressing instead of the sesame seeds defatted with hexane.
In the same manner as in the above, a second step for obtaining 360 parts by volume of ethanol water in which sesaminol triglucoside is dissolved in 0.07% by weight is obtained, and when this is dried, sesaminol triglucoside having a purity of 60% by weight can be obtained.

3) In the above 2), the flow rate in the column was adjusted to 1.9 parts by volume / minute, and otherwise the same as in 2) to obtain 360 parts by volume of ethanol water in which 0.07% by weight of sesaminol triglucoside was dissolved. It consists of two steps, and when it is dried, sesaminol triglucoside having a purity of 42% by weight can be obtained.

4) In the above 2), 3 parts by weight of activated carbon were used, and in the first step, 60 parts by volume were used instead of 180 parts by volume of 30% by volume ethanol water, and in the second step, 60% by volume ethanol was used. Instead of 360 parts by volume of water, 120 parts by volume was used, and otherwise the same as in 2) above, and ethanol water 120 containing 0.17% by weight of sesaminol triglucoside was dissolved.
It comprises a second step of obtaining a volume part, and when it is dried, sesaminol triglucoside having a purity of 32% by weight can be obtained.

5) In the first step of 4), 60 parts by volume of 20% by volume ethanol water was used instead of 60 parts by volume of 30% by volume ethanol water, and otherwise the same as in 2) above. The second step is to obtain 120 parts by volume of ethanol water in which 0.19% by weight of nortriglucoside is dissolved, and when it is dried, sesaminol triglucoside having a purity of 31% by weight can be obtained.

6) In the second step of the above 5), 75% by volume of ethanol water is used in place of the 60% by volume of ethanol water, and otherwise, the sesaminol triglucoside is 0.19%. Ethanol water dissolved by weight%
When 120 parts by volume are obtained and dried, a sesaminol triglucoside having a purity of 30% by weight can be obtained.

[0025]

EXAMPLE In the following test categories 1 to 8, tests were conducted to determine the differences in sesaminol triglucoside due to various conditions such as raw materials, adsorbents, types of activated carbon, temperature, and aqueous ethanol concentration. Is shown in the table and figures. Then, Examples 1 to 9 and Comparative Examples 1 to 4 were implemented as Test Section 9, and comparisons between Examples and Comparative Examples were summarized in a table as Test Section 10. Test category 1 (sesame seed raw material for extracting sesaminol glucoside) Test Example 1 For defatted sesame seeds, which is a raw material for extracting sesaminol glucoside, those extracted after roasting and those extracted without roasting , Extracted with hexane without roasting, 3
The types were compared. That is, 600 ml of hot water at 100 ° C. was added to 100 g of each raw material defatted sesame seed, stirred for 5 minutes, filtered under reduced pressure to obtain 400 ml of extract, and the total amount of sesaminol triglucoside contained therein was compared. From these results, it was found that an extract containing substantially the same amount of sesaminol triglucoside was obtained from any of the raw material defatted sesame seeds, and that all of them could be suitably used as raw materials. The results are summarized in Table 1.

Test Category 2 (Adsorption of Sesaminol Triglucoside to Various Adsorbents) Test Example 2 Extraction obtained by adding 600 ml of hot water to 100 g of unroasted and pressed sesame seeds (hereinafter referred to as defatted sesame seeds) in advance. Prepare 400 ml of liquid. Alumina, strong anion exchanger (carrier: polystyrene resin), silica, C18 (carrier:
Silica), magnesium oxide, talc, acid clay, kaolin, bentonite, XAD-2, activated carbon (specific surface area 1050m2 /
g, pore volume of 10 細孔 or more 1.03ml / g)
Stir overnight at 25 ° C, remove the adsorbent by centrifugation, and adsorb the amount obtained by subtracting the amount of sesaminol triglucoside remaining in the liquid after adsorption from the amount of sesaminol triglucoside remaining in the liquid. It was calculated as the amount of sesaminol triglucoside adsorbed by the agent. Some adsorbents adsorbed sesaminol triglucoside, but among them, activated carbon was much higher and showed higher adsorption. The results are summarized in Table 2.

Test Category 3 (Relationship between Type of Activated Carbon and Adsorption of Sesaminol Triglucoside) Test Example 3 Extraction obtained by the same method as in Test Example 2 as a relationship between the type of activated carbon and the adsorption of sesaminol triglucoside. Six types of activated carbon were added to the solution, and the adsorption of different raw materials of sesaminol glucoside to activated carbon was compared. That is, 600 ml of hot water at 100 ° C. was added to 100 g of defatted sesame seeds and stirred to obtain 400 ml of an extract. Add 5g of activated carbon to this and add 2
Stir at 5 ° C for 2 hours and subtract the amount of sesaminol triglucoside remaining in the liquid after adsorption from the amount of sesaminol triglucoside in the extract to calculate the amount as the amount of sesaminol triglucoside adsorbed by activated carbon did. As a result, it was found that the adsorption of sesaminol triglucoside seems to be affected by the pore size. The results are summarized in Table 3.

Test Category 4 (Adsorption condition of sesaminol triglucoside on activated carbon: temperature) Test Example 4 As an adsorption condition of sesaminol triglucoside on activated carbon, the extract obtained by the same method as in Test Example 2 was used. Activated carbon (specific surface area 1050m2 / g, pore volume of 10ml or more 1.03ml / g)
Was added and stirred at each temperature, and the adsorption of sesaminol triglucoside to activated carbon was compared. That is, 600 ml of hot water at 100 ° C. was added to 100 g of defatted sesame seeds, and stirred, and 400 ml
Was obtained. This was divided into 100 ml portions, 5 g of activated carbon was added, and the mixture was stirred at 25 ° C, 40 ° C, 60 ° C, and 80 ° C for 2 hours.After adding activated carbon, 5, 10, 20, 40, 60, 90, and 120 minutes later, The amount obtained by subtracting the amount of sesaminol triglucoside remaining in the liquid after the adsorption was calculated as the amount of sesaminol triglucoside adsorbed by the activated carbon. As the temperature increased, the adsorption rate of sesaminol triglucoside on activated carbon increased, and reached equilibrium at 80 ° C after 90 minutes. The results are summarized in FIG.

Test Category 6 (elution of sesaminol triglucoside from activated carbon: ethanol water concentration) Test Example 6 As a first step and a second step, a wet state of activated carbon adsorbing an adsorption component containing sesaminol triglucoside was used. Ethanol water was added and stirred, and the elution of sesaminol triglucoside from activated carbon in different concentrations of ethanol water was compared. That is, 1.5 kg of defatted sesame seeds
9 l of hot water at 100 ° C. was added to the mixture and stirred to obtain 6 l of an extract. Activated carbon (specific surface area 1050m2 /
g, 10Å or more pore volume 1.03ml / g) Add 5g and add 2 at 60 ℃
After stirring for a period of time, the solution part was separated to obtain each activated carbon in a wet state to which the adsorption component containing sesaminol triglucoside was adsorbed. To each of the activated carbons, 0, 20, 40, 60, 80, and 400 ml of 100% by volume ethanol water were added, and the mixture was stirred at 25 ° C for 2 hours.
The amount of sesaminol glycoside eluted in ethanol water was measured, and the ratio of elution to the amount of sesaminol glycoside originally adsorbed was examined. Sesaminol triglucoside is
The elution was greatest at an ethanol concentration of around 60% by volume, and the same tendency was observed at 60 ° C, but an elution rate higher than 25 ° C was obtained. The results are summarized in Table 4.

Test Category 7 (elution of sesaminol triglucoside from activated carbon: temperature) Test Example 7 As a second step, wetness in which an adsorbed component containing sesaminol triglucoside obtained through the same process as in test section 6 was adsorbed Add 400 ml of 60% by volume ethanol water to activated carbon
The mixture was stirred at 40 ° C., 40 ° C., 60 ° C., and 80 ° C. for 2 hours, and after 5, 10, 20, 40, 60, 90, and 120 minutes after adding ethanol water, the amount of eluted sesaminol triglucoside was measured. As the temperature increased, more sesaminol triglucoside eluted, and reached an equilibrium at 80 ° C after 40 minutes. The results are summarized in FIG.

Test Category 9 (Separation of Sesaminol Triglucoside) Example 1 300 g of defatted sesame seeds obtained by extracting hexane with oil from non-roasted sesame seeds was added with 1800 ml of hot water at 100 ° C. and stirred. ,
Thereafter, the defatted sesame seeds were separated by filtration to obtain 1200 ml of an extract containing 0.75 g of sesaminol triglucoside. Next, activated carbon (specific surface area 1050m2 / g, pore volume of 1.03ml or more 1.03ml / g) 24
g (160 ml) was passed through a glass column filled with the above extract, and as a first step, 540 ml of 30% by volume ethanol water was passed, and finally, as a second step, 1080 ml of 60% by volume ethanol water was added.
And collected. During the process from the adsorption to the elution of sesaminol triglucoside, the column temperature was 60 ° C., and the flow rate in the column was 3.2 ml / min.

Examples 2 to 8, Comparative Examples 1 to 3 Skim sesame seeds 30 obtained by squeezing and extracting oil from non-roasted sesame seeds 30
Separation operations were performed in the same manner as in Example 1 except that 0 g was used, except for the conditions shown in Tables 5 and 6, to obtain ethanol water in which sesaminol triglucoside was dissolved.

Example 9 Skim sesame seeds 30 obtained by squeezing and extracting oil from non-roasted sesame seeds 30
1800 ml of hot water at 100 ° C. was added to 0 g and stirred, and then the defatted sesame seeds were filtered off to remove sesaminol triglucoside by 0.75 g.
1200 ml of extract containing g was obtained. Next, activated carbon (specific surface area 1050m2 / g, pore volume of 10Å or more 1.03ml / g)
9 g (60 ml) was added thereto, and the mixture was stirred at 25 ° C. overnight, and the solution was separated to obtain activated carbon to which an adsorption component containing sesaminol triglucoside was adsorbed. Next, as a first step, 300 ml of 40% by volume ethanol water was added to the wet activated carbon and the mixture was stirred at 25 ° C. for 2 hours to separate and wash the activated carbon to obtain activated carbon. Finally, as the second step, the activated carbon was replaced with
The ethanol evaporated at 80 ° C. was added to the mixture, and the mixture was extracted with reflux, and the activated carbon was separated to obtain ethanol water in which sesaminol triglucoside was dissolved.

Test Category 10 (Analysis of Separated Sesaminol Triglucoside) With respect to ethanol water in which sesaminol triglucoside in which sesaminol triglucoside was dissolved, which was obtained in each of Examples 1 to 9 and Comparative Examples 1 to 4, was dissolved. The concentrations of sesaminol triglucoside and solids contained in the ethanol water were analyzed by the following method. From these results, the recovery rate of sesaminol triglucoside and the purity of sesaminol triglucoside contained in the solid content were calculated by the following formulas 1 and 2. The results are summarized in Table 7.

Analysis of sesaminol triglucoside contained in ethanol water The ethanol water in which sesaminol triglucoside obtained in each example was dissolved was filtered through a Millipore filter, and the filtrate was subjected to high performance liquid chromatography under the following conditions. Then, sesaminol triglucoside contained in ethanol water was analyzed.・ ・ Conditions for high-performance liquid chromatography Fixed layer: Novel Chemical Devosil ODS-10 Column diameter: 6 mm, column length: 250 mm Developing solvent flow rate: 1 ml / min Detector: UV (290 nm)

Analysis of Solids Concentration Contained in Ethanol Water The weight (S1) of ethanol water in which sesaminol triglucoside obtained in each example was dissolved was weighed. Then, after distilling ethanol and water from this ethanol water under reduced pressure,
The weight of the freeze-dried solid was weighed using a freeze dryer (FDU-540 manufactured by Tokyo Rikakikai Co., Ltd.). From these weights, the solid concentration contained in the ethanol water was calculated.

• Recovery rate of sesaminol triglucoside (Y) [Equation 1] Y (%) = ｛(S ₁ × C ₁ ) / (100 × 0.75)｝ × 100 Purity of glucoside (P) [Formula 2] P (%) = (C ₁ / C ₂ ) × 100 [In formulas 1 and 2, Y: recovery rate of sesaminol triglucoside (% by weight) P: in solid content Purity of sesaminol triglucoside contained (wt%) S ₁ : volume of ethanol water in which sesaminol triglucoside is dissolved (ml) C ₁ : concentration of sesaminol triglucoside contained in ethanol water エ タ ノ ー ル% (weight / volume) ｝ C ₂ : Concentration of solid content in ethanol water ｛% (weight /
capacity)}]

[0038]

[Table 1]

[0039]

[Table 2]

[0040]

[Table 3]

[0041]

[Table 4]

[0042]

[Table 5]

[0043]

[Table 6]

[0044]

[Table 7] In Tables 5, 6 and 7, the amount of sesaminol triglucoside contained in the extract used in the first step: 0.75 g Y: recovery rate of sesaminol triglucoside (% by weight) P: contained in solids S1: Purity of sesaminol triglucoside (% by weight) S1: Amount of ethanol water in which sesaminol triglucoside is dissolved (ml) C1: Concentration of sesaminol triglucoside contained in ethanol water [% (weight / volume)] C2: Solid content concentration in ethanol water [% (weight /
capacity)]

As described above, in the Examples, the recovery of sesaminol triglucoside and the purity of sesaminol triglucoside contained in the solid content are both high, and the sesaminol triglucoside can be easily and simply purified with high purity and high yield. It can be seen that the effect of the present invention of separation can be obtained. on the other hand,
In the comparative example, at least one of the recovery rate of sesaminol triglucoside and the purity of sesaminol triglucoside contained in the solid content was low, and the effect of the present invention was not obtained. Recognize.

[0046]

According to the present invention, sesaminol triglucoside useful as a material for foods, pharmaceuticals, cosmetics, etc. can be easily prepared.
This has the effect that separation can be performed with high purity and high yield.

[Brief description of the drawings]

FIG. 1 is a graph showing the relationship between the amount of sesaminol triglucoside adsorbed on activated carbon and temperature.

FIG. 2 is a graph showing the relationship between elution of sesaminol triglucoside from activated carbon and temperature.

Claims (5)

[Claims] 1. A solvent-soluble component containing sesaminol triglucoside is extracted from defatted sesame seeds using a solvent selected from water, ethanol or ethanol water, and the obtained extract is brought into contact with activated carbon to extract the solvent-soluble component. A method for producing sesaminol triglucoside, which comprises adsorbing a part of a solvent-soluble component to activated carbon, and then collecting sesaminol triglucoside from the adsorbed component. 2. The method for producing sesaminol triglucoside according to claim 1, wherein the sesaminol triglucoside is collected from the component adsorbed on the activated carbon through the following first step and second step. First step: by contacting ethanol water or water having an ethanol concentration of 40% by volume or less at 40 ° C. or higher,
A step of washing the activated carbon to which a part of the solvent-soluble component is adsorbed. Second step: The activated carbon washed in the first step and ethanol water having an ethanol concentration in the range of 50 to 98% by volume
A step of desorbing and eluting sesaminol triglucoside by contacting at a temperature of at least ℃ to obtain ethanol water in which sesaminol triglucoside is dissolved. 3. The method for producing sesaminol triglucoside according to claim 2, wherein in the first step, ethanol water has an ethanol concentration of 10 to 40% by volume. 4. The method for producing sesaminol triglucoside according to claim 2, wherein in the second step, the ethanol water has an ethanol concentration of 55 to 75% by volume. 5. The method for producing sesaminol triglucoside according to claim 2, wherein in the second step, the contacting is performed at a temperature from 50 ° C. to the boiling point of the ethanol water.