Method for producing a glucosinolate-containing composition and method for increasing the extraction efficiency of glucosinolates from glucosinolate-containing plants

By using a mixed solvent of ethanol and water and an appropriate extraction temperature, the problems of low extraction efficiency and poor stability of cereal thiol acid in plants are solved, and efficient and stable extraction effect is achieved, which is suitable for food and beverage applications.

JP7672965B2Active Publication Date: 2025-05-08KAGOME
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Patent Information

Application Number
JP2021210065
Authority / Receiving Office
JP · JP
Patent Type
Patents
Current Assignee / Owner
Filing Date
2021-12-24
Publication Date
2025-05-08
Estimated Expiration
2041-12-24

AI Technical Summary

Technical Problem

The prior art is inefficient when extracting cereal thiolates from plants, and the extracted thiolates are prone to deterioration, affecting its stability and functionality.

Method used

The mixed solvent of ethanol and water is used as the extraction agent, and the volume ratio of ethanol is controlled between 1% and 20%, and the extraction temperature is controlled at 60°C or above. These methods are used to improve the extraction efficiency and stability of cereal thiol acid.

Benefits of technology

It significantly improves the extraction efficiency and stability of cereal thiol acid, extends its functional retention time, and is suitable for applications in food and beverages.

✦ Generated by Eureka AI based on patent content.

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Abstract

To enhance an extraction efficiency of a glucosinolate from a glucosinolate-containing plant, in production of a glucosinolate-containing composition.SOLUTION: In order to solve the problem, the present inventors have made intensive studies and discovered that when producing a glucosinolate-containing composition, at least an extraction step is provided. What is extracted in the extraction step is the glucosinolate-containing plant. An extraction solvent used here is a mixed liquid of ethanol and water, a volume ratio of ethanol in the mixed liquid is 1% or more and 20% or less.SELECTED DRAWING: Figure 1
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Description

[Technical field]

[0001] The present invention relates to a method for producing a glucosinolate-containing composition, A method for increasing the efficiency of extraction of glucosinolates from plants. [Background technology]

[0002] Glucosinolates, which are unique to cruciferous plants, have a strong effect on the plant body and the human intestine. It is converted into isothiocyanate by myrosinase in the internal flora and then absorbed into the body. In particular, broccoli sprouts and seeds contain It contains a lot of phophalan glucosinolate (hereinafter referred to as "SGS"). The physiological effects of the converted sulforaphane include detoxification, improving liver function, and antioxidant effects. etc. have been reported. Focusing on this physiological effect, glucosinolates, especially SGS, can be used for various food and beverage applications. This is expected to contribute to the health of many consumers.

[0003] Patent Document 1 discloses a juice composition derived from a Brassicaceae plant, the purpose of which is to The method involves producing juice containing increased amounts of glucosinolates from kale under specific heating conditions. The process involves heating and squeezing the juice.

[0004] Patent Document 2 discloses a method for producing a food product containing a cruciferous plant, the purpose of which is to: Contains significant amounts of indole glucosinolates and their breakdown products that have phase II-inducing potential and foods containing non-toxic concentrations of goitrogenic hydroxybutenyl glucosinolate. The method includes selecting seeds, germinating the seeds, and performing a process from the start of germination to the stage of use. The sprouts are harvested during the cultivation to produce a food product. [Prior art documents] [Patent documents]

[0005] [Patent Document 1] Patent No. 5726535 [Patent Document 2] JP 2000-502245 A Summary of the Invention [Problem to be solved by the invention]

[0006] The challenge in producing glucosinolate-containing compositions is to extract the glucosinolates from plants that contain glucosinolates. The aim is to increase the extraction efficiency of glucosinolates. Sothiocyanate (chemical formula 1) is a useful ingredient from a functional standpoint, but it is volatile and therefore unsafe. It is constant and disappears over time. Therefore, when ingesting, it is recommended to consume it immediately before or after it is absorbed into the body. Therefore, it is preferable that the isothiocyanate be converted to isothiocyanate when used in food and beverages and their raw materials. In the composition, it is preferable that the glucosinolate is in a highly stable state.

[0007] [ka]

[0008] One method for producing a composition containing glucosinolates is to However, the extraction of glucosinolates from glucosinolate-containing plants Many plants also contain myrosinase, which breaks down glucosinolates. Therefore, the glucosinolates were extracted with myrosinase during or after the extraction. It is necessary to pay attention to the decomposition of the

[0009] In addition, even after extracting glucosinolates, there are still glucosinolates in the glucosinolate plants. Therefore, the extraction method of glucosinolates was investigated. However, there is room for further study to improve the extraction efficiency.

[0010] In other words, the problem in producing a glucosinolate-containing composition is The object of the present invention is to increase the efficiency of extraction of glucosinolates from food. [Means for solving the problem]

[0011] In order to solve the above problems, the present inventors have conducted extensive research and discovered glucosinolates. The composition of the solvent allows for highly efficient extraction during extraction. By selecting the appropriate organic solvent and finding the appropriate content ratio as the extraction solvent, This makes it possible to extract glucosinolates efficiently.

[0012] The method for producing a glucosinolate-containing composition includes at least an extraction step. In the extraction step, a glucosinolate-containing plant is extracted by a person or a device. The extraction solvent used here is a mixture of ethanol and water, and the volume ratio of ethanol in the mixture is 1% or more and 20% or less. The temperature of the mixture during the extraction is preferably 60°C or more. In addition, the glucosinolate-containing plant is preferably a Brassicaceae plant. Furthermore, the glucosinolate is preferably glucoraphanin or glucoraphenin.

[0013] The method for increasing the efficiency of extraction of glucosinolates from a glucosinolate-containing plant comprises at least an extraction step. The glucosinolate-containing plant is extracted in the extraction step. The extraction solvent used here is a mixture of ethanol and water, and the volume ratio of ethanol in the mixture is 1% or more and 20% or less. The temperature of the mixture during the extraction is preferably 60°C or more. In addition, the glucosinolate-containing plant is preferably a Brassicaceae plant. Furthermore, the glucosinolate is preferably glucoraphanin or glucoraphenin. Effect of the Invention

[0014] The present invention makes it possible to extract glucosinolates from glucosinolate-containing plants. The goal is to increase efficiency. [Brief description of the drawings]

[0015] [Figure 1] Flowchart of a method for producing a glucosinolate-containing composition DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0016] <Glucosinolate-containing composition> The glucosinolate-containing composition according to the present invention (hereinafter referred to as the "composition"). ) composition, characterized in that it contains glucosinolate. and juice containing glucosinolates, plant extracts containing glucosinolates (extracts ), purified products containing glucosinolates, as well as concentrates, dried products and powders thereof; etc.

[0017] <Glucosinolate> Glucosinolates are derivatives of glucose and amino acids, as shown in the structural formula 2. Glucosinolates are a group of organic compounds that contain sulfur and nitrogen. Examples of the glucosinolate include, but are not limited to, sulforaphane glucosinolate (glucoraphane). (also called guanine), sinigrin, glucoerucin, glucobrassicin, glucoraphene glucosinolate, glucoraphasatin, phenethyl glucosinolate, etc. In particular, sulforaphane glucosinolate is preferred. One or more of the above may be used.

[0018] [ka]

[0019] <Glucosinolate-containing plants and Brassicaceae plants> The glucosinolate-containing plant in the present invention is a plant that contains glucosinolate. In particular, the glucosinolate-containing plant of the present invention is a cruciferous plant. In the present invention, the Brassicaceae plant is preferably a plant belonging to the Brassicaceae family. Examples include cabbage, broccoli, kale, watercress, and co Matsuna, bok choy, radish sprouts, cauliflower, Chinese cabbage, turnip, takana, Kohlrabi, etc. One or more of these plants may be used. All or part of these plant parts (flowers, leaves and stems) may be used, as well as sprouts and seeds. In a particularly preferred embodiment of the present invention, broccoli sprouts or broccoli sprouts may be used. These are cucumber seeds.

[0020] Plant juice is the juice obtained by crushing and squeezing or straining plants, and then concentrating it. These include concentrated juices that have been diluted with other ingredients (e.g. For example, small amounts of salt, spices, food additives, etc. may be contained.

[0021] A plant extract is a substance that is extracted from a plant using a solvent, and It is a concentrated form of

[0022] <Method of producing the glucosinolate-containing composition> The method for producing the present composition (hereinafter referred to as "the present method") mainly comprises the steps of extraction, processing, and These are the heating process, the concentration process, the sterilization process, the filling process, and the cooling process.

[0023] <Extraction (S010)> The purpose of the extraction is to extract glucosinolates from plants that contain glucosinolates. When glucosinolate-containing plants are exposed to the extraction solvent, the glucosinolates are extracted and dissolved. The extraction time can be shortened by increasing the temperature of the extraction solvent. Increasing the temperature can inactivate myrosinase in plants that contain glucosinolates. From this perspective, the temperature at which glucosinolates are extracted from the plant is set at 6 The temperature is 0°C or higher and 95°C or lower, and preferably 70°C or higher and 95°C or lower.

[0024] <Extraction solvent> In the present invention, the extraction solvent used in the extraction is a mixture of an organic solvent and water. The organic solvent is ethanol. The volume ratio of ethanol in the mixture is Preferably, it is 1% or more and 20% or less. More preferably, it is 5% or more and 2 It is less than 0%.

[0025] <Heating (S020)> One of the purposes of heating is to inactivate myrosinase in plants that contain glucosinolates. By carrying out the heating, myrosinase is inactivated and the decomposition of glucosinolate is suppressed. Another purpose of heating is sterilization. The timing of heating is not particularly limited. One embodiment of the heat period is prior to the extraction step. Alternatively, the myrosinase contained in the plant can be inactivated by indirect heating. Another embodiment of the timing of heating is simultaneous with the extraction. One embodiment is simultaneous with or after concentration, which will be described later. The temperature during heating is not particularly limited. From the viewpoint of inactivating myrosinase, the lower limit of the temperature is preferably 60°C. Preferably, it is 70° C. Also, preferably, the upper limit of the temperature is 100° C.

[0026] <Concentration (S030)> The purpose of the concentration is to improve the handling of the composition. By concentrating a liquid composition, The volume of the liquid is reduced, which means the liquid storage cost is reduced. Examples of such methods include vacuum concentration, membrane concentration, and freeze concentration.

[0027] <Sterilization, cooling (S040), filling (S050)> In addition to the above, the present method appropriately employs sterilization, filling and cooling. Any known method may be used, for example, plate sterilization, tubular sterilization, etc. The filling method may be a known method. The filling method may be a known method. The containers may be any known container, for example, cans, bottles, paper containers, polyethylene containers, etc. It is.

[0028] <Glucosinolate-containing foods and beverages> The glucosinolate-containing food and drink according to the present invention (hereinafter referred to as the present food and drink) is a food and drink that contains glucosinolate. It refers to a beverage or food containing glucosinolate. This food and beverage preferably contains, as a raw material, the glucosinolate-containing composition according to the present invention. The beverage is not particularly limited as long as it is generally recognized as a beverage such as a soft drink or a smoothie. This food and beverage includes those containing some solid components such as soup.

[0029] <Physiological activity> The glucosinolate-containing food and beverage has enhanced functionality of glucosinolate. From this perspective, this food and beverage may have at least one functionality selected from the group consisting of liver function improvement effect, blood glucose level improvement effect, diabetes prevention effect, Pylori bacterium sterilization effect, vital capacity and respiratory function improvement effect, LDL cholesterol reduction effect, excretion promotion effect of air pollutants, bowel movement improvement effect, memory and attention improvement effect, schizophrenia alleviation effect, obesity prevention and improvement effect, fatty liver prevention and improvement effect, dementia prevention effect, cognitive function improvement effect, intestinal flora improvement effect, depression prevention effect, prostate prevention effect.

Examples

[0030] The test examples 1 to 5 embody this composition. However, the scope of the claims according to the present invention is not limited by these examples.

[0031] <Measurement of SGS concentration> The measurement method of SGS adopted in this measurement is the HPLC method. The sample was appropriately diluted and filtered through a filter and used as the specimen. The detailed measurement conditions are as follows.

[0032] <HPLC measurement conditions> Apparatus: ACQUITY UPLC H-Class system (manufactured by Waters) ​​​​​​​​​​​Column: ACQUITY CSH C18 (Φ2.1×100 mm, 1.7 μm) (Wa ters Co., Ltd.) Column temperature: 30 °C Sample injection volume: 10 μL Mobile phase A: Ultrapure water: Trifluoroacetic acid = 99.95:0.05 (v:v) Mobile phase B: Methanol: Trifluoroacetic acid = 99.95:0.05 (v:v) Gradient: Maintain the mobile phase B ratio at 0% for 5 minutes Linear gradient of mobile phase B ratio from 0 to 10% in 10 minutes Linear gradient of mobile phase B ratio from 10 to 100% in 5 minutes Maintain the mobile phase B ratio at 100% for 5 minutes Linear gradient of mobile phase B ratio from 100 to 0% in 2 minutes Maintain the mobile phase B ratio at 0% for 5 minutes Flow rate: 0.1 mL / min Detection wavelength: 235 nm

[0033] <SGS recovery rate> In this example, the SGS recovery rate refers to the ratio of the SGS concentration of the sample in each test example when the SGS concentration of the sample in Comparative Example 1 is taken as 100 The numerical values shown in Table 1 and Table 2 are all average values at n = 2

[0034] <Comparative Example 1> Commercially available broccoli seeds (supplier: Plant Life Design) were heat-treated in an autoclave at 90 °C for 10 minutes. To 2 g of the seeds after autoclaving, 10 g of water was mixed, and using a thermostatic bath, it was heated with stirring at 70 °C for 60 minutes. After heating the seeds were removed, the liquid part was recovered, and the SGS concentration of the liquid part was measured

[0035] <Test Examples 1 to 8> Commercially available broccoli seeds (supplier: Plant Life Design) were put into an autoclave Furthermore, heat treatment was performed at 90°C for 10 minutes. For 2 g of the seeds after autoclaving, 10 g of a mixed solution of ethanol and water was mixed, and using a thermostatic bath, it was heated at 70°C for 60 minutes without stirring. The volume ratio of ethanol in the mixed solution was set to 1%, 5%, 10%, 15%, 20%, 30%, 50%, and 70%, and each test section was designated as Test Examples 1 to 8 respectively. After heating, the seeds were removed, the liquid portion was recovered, and the SGS concentration and SGS recovery rate of the liquid portion were measured (Table 1).

[0036] <Test Examples 9 to 12> Seeds of commercially available broccoli (vendor: Plant Life Design) were subjected to heat treatment at 90°C for 10 minutes in an autoclave. For 2 g of the seeds after autoclaving, 10 g of a mixed solution of ethanol and water was mixed, and using a thermostatic bath, it was heated at 70°C for 60 minutes without stirring. The volume ratio of propanol in the mixed solution was set to 10%, 30%, 50%, and 70%, and each test section was designated as Test Examples 9 to 12 respectively. After heating, the seeds were removed, the liquid portion was recovered, and the SGS recovery rate of the liquid portion was calculated (Table 2).

[0037] <Evaluation of Improvement in SGS Extraction Efficiency> In this test, the sections with a higher SGS recovery rate compared to the control section were evaluated as "〇" for the improvement in SGS extraction efficiency. Also, the sections with a lower SGS recovery rate compared to the control section were evaluated as "×" for the improvement in SGS extraction efficiency.

[0038]

Table 1

[0039]

Table 2

[0040] <Results and Summary> When extracting SGS from broccoli seeds, a mixture of water and ethanol was used as the extraction solvent. By using ethanol at 1% or more, the extraction efficiency of SGS was improved. The extraction efficiency of SGS was improved when the mixture of 20% or less of the extractant and the extractant was used. Therefore, when propanol was used, the extraction efficiency of SGS did not improve, but rather decreased. I did.

[0041] From the above test results, it can be seen that when extracting glucosinolates from glucosinolate plants, It was found that a mixture of water and ethanol was effective as a solvent. By using a mixed solvent with an ethanol ratio of 1% or more and 20% or less, It was found that the extraction efficiency of glucosinolates was improved. It is possible to produce glucosinolate-containing compositions with improved efficiency and increased recovery. It was found that... [Industrial Applicability]

[0042] The field of the invention is related to methods for producing glucosinolate-containing compositions, A method for increasing the efficiency of extraction of glucosinolates from plants.

Claims

1. A method for producing a glucosinolate-containing composition comprising at least the following steps: Heating: Here, the glucosinolate-containing plants are heated. Extraction: The heated glucosinolate-containing plant is extracted, the extraction solvent used is a mixture of ethanol and water, and the volume ratio of ethanol in the mixture is 1% or more and 20% or less; The temperature of the mixture during the extraction is 60° C. or higher.

2. The method of claim 1, wherein the glucosinolate-containing plant is a Brassicaceae plant.

3. The method according to claim 1 or 2, wherein the glucosinolate is glucoraphanin or glucoraphenin.

4. A method for increasing the efficiency of extraction of glucosinolates from glucosinolate-containing plants, comprising at least the following steps: Heating: Here, the glucosinolate-containing plants are heated. Extraction: The heated glucosinolate-containing plant is extracted, the extraction solvent used is a mixture of ethanol and water, and the volume ratio of ethanol in the mixture is 1% or more and 20% or less; The temperature of the mixture during the extraction is 60° C. or higher.

5. 5. The method of claim 4, wherein the glucosinolate-containing plant is a Brassicaceae plant.

6. 6. The method of claim 4 or 5, wherein the glucosinolate is glucoraphanin or glucoraphenin.

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