JP7703278B2 - Method for producing glucosinolate-containing plant powder - Google Patents

Description

The present invention relates to a method for producing a glucosinolate-containing plant powder.

In recent years, with the rise of health consciousness, people are paying attention to the nutritional and functional components of food and drink. Among the various foods and drinks available, green juice drinks are widely recognized as a convenient way to ingest the nutritional components of vegetables. Green juice is generally made from green plants such as young barley leaves and kale. In order to process these ingredients into a form suitable for consumption,
Various studies have been conducted so far.

On the other hand, one of the functional ingredients derived from food that has attracted attention is glucosinolate (hereinafter referred to as "
GSLs are contained in plants, such as cruciferous vegetables such as broccoli, cabbage, and radish. It is known that the intake of GSLs can prevent and improve various diseases such as cancer and liver disorders. Ingested GSLs are converted into isothiocyanates (hereinafter also referred to as "ITCs"), and ITCs act as the active form and have the aforementioned preventive and therapeutic effects.
Various studies have been conducted on glucosinolates to develop them into materials.
Patent Document 1 describes a food product and extract containing a cruciferous plant, and the food product contains new shoots obtained by germinating the seeds of a cruciferous plant and cultivating them for a certain period of time.

Patent Document 2 describes a plant powder, which is dried at a certain temperature for a certain period of time and then pulverized to obtain a natural plant material.

Special Publication No. 2000-502245 Special Publication No. 2013-544092

The problem to be solved by the present invention is to provide a plant powder with a high glucosinolate content. Conventional green plant powders such as green juice have a low glucosinolate content. What is required for green plant powders for consumption is to provide a plant powder with a high glucosinolate content.

In order to solve this problem, the present inventors have conducted extensive research and discovered the relationship between the residual amount of glucosinolate and the processing step. With each processing step, the amount of glucosinolate in a processed product of a glucosinolate-containing plant decreases. On the other hand, unless the glucosinolate-containing plant is processed, it is impossible to make it into a form suitable for consumption or to inactivate myrosinase (which breaks down glucosinolate) present in the glucosinolate-containing plant. From this perspective, the present invention is defined as follows.

The manufacturing method of glucosinolate-containing plant powder comprises at least dehydration, non-immersion heating, and drying steps. In the dehydration step, the glucosinolate-containing plant is dehydrated by a person or device. In the non-immersion heating step, the dehydrated glucosinolate-containing plant is heated by a device. Here, non-immersion heating refers to heating in which the object to be heated is not immersed (e.g., in a water bath, a hot bath, etc.). The heating medium used in the heating is preferably one or more of steam and superheated steam. In the drying step, the heated glucosinolate-containing plant is dried by a device.

The method further comprises a cutting step, in which the heated glucosinolate-containing plant is cut by a person or a device, and a crushing step, in which the heated glucosinolate-containing plant is crushed by a person or a device.

The method further comprises a granulation step, in which the dried glucosinolate-containing plant is granulated by a person or a machine. The granulation method is preferably fluidized bed granulation. In addition, the binder in the fluidized bed granulation is preferably one or more of water and a glucosinolate-containing liquid.

Furthermore, it is preferable that the particle size of the glucosinolate-containing plant powder after grinding is such that d10 is 25 μm or less, d50 is 50 μm or less, and d90 is 130 μm or less.

In addition, it is preferable that the particle size of the glucosinolate-containing plant powder after granulation is such that d10 is 30 μm or more, d50 is 60 μm or more, and d90 is 100 μm or more.

The glucoraphanin content of the glucosinolate-containing plant powder obtained by the above-mentioned production method is preferably 5 mg or more per 1 g of the glucosinolate-containing plant powder. Furthermore, the glucosinolate-containing plant used here is preferably a cruciferous vegetable.

The present invention makes it possible to provide a glucosinolate-containing plant powder having a high glucosinolate content, and furthermore, to improve the dispersibility in water and make it suitable for consumption.

Flowchart of the method for producing glucosinolate-containing plant powder

<Glucosinolate-containing plant powder>
The glucosinolate-containing plant powder according to the embodiment of the present invention is a powder that contains at least a glucosinolate-containing plant as a raw material. More specific forms will be described later.

The glucosinolate-containing plant of the present invention may be any plant that contains glucosinolate. In particular, from the viewpoint of containing a large amount of glucosinolate, the glucosinolate-containing plant of the present invention is preferably a vegetable belonging to the Brassicaceae family. More preferably, the glucosinolate content in the glucosinolate-containing plant of the present invention is:
The amount is 1.0 mg or more per gram of the glucosinolate-containing plant. The glucosinolate-containing plant according to the present invention is preferably a green plant. The green plant may be any plant whose color is green. The green color of plants is generally composed of chlorophyll. The glucosinolate-containing plant powder according to the present invention preferably contains chlorophyll from the viewpoint of color.

The dried and ground glucosinolate-containing plant product according to the embodiment of the present invention is obtained by drying and grinding a glucosinolate-containing plant as a raw material, specifically, a glucosinolate-containing plant that has been dried and then ground, a glucosinolate-containing plant that has been cut and dried and then ground, a glucosinolate-containing plant that has been dried and ground at the same time, or the like, is a glucosinolate-containing plant that has been dried and ground.

In addition, the glucosinolate-containing plant powder according to the embodiment of the present invention specifically contains at least a powdered form of a glucosinolate-containing plant, such as the glucosinolate-containing dried and ground product, granulated versions of the glucosinolate-containing dried and ground product, and mixtures of these processed products with other powder compositions.

The glucosinolate-containing plant powder of the present invention is not only composed of glucosinolate extracted from a glucosinolate-containing plant using a solvent. By using the components in the glucosinolate-containing plant without fractionation, the utilization efficiency of the glucosinolate in the glucosinolate-containing plant can be improved. In addition, various nutrients such as dietary fiber that are insoluble in the solvent can be simultaneously ingested when eating or drinking.

<Conceptual configuration of a method for producing glucosinolate-containing plant powder>
This method for producing glucosinolate-containing plant powder (hereinafter sometimes referred to as "this method")
Conceptually, at least the steps of water removal, heating, and drying are included.
Fig. 1 shows the flow of this manufacturing method. This manufacturing method is composed of washing (S10), water removal (S20), heating (S30), cutting (S40), drying (S50), crushing (S60), granulation (S70), and sterilization and filling (S80). However, the above steps and the order of steps are not limited, and steps can be added and the order of steps can be changed as appropriate.

<Cleaning (S10)>
The purpose of washing the glucosinolate-containing plant is to remove foreign matter or reduce the number of bacteria. Examples of foreign matter include mud, soil, sand, etc. that adhere to the green plant glucosinolate-containing plant. The means for washing the glucosinolate-containing plant is not particularly limited, but is preferably contact with water or sterilized water. The method for contacting the plant is not particularly limited, but examples include immersion, spraying, etc. The number of times the glucosinolate-containing plant is washed is one or more times. The washing solution used for washing is not particularly limited, but examples include water, hypochlorous acid, hypochlorite, chlorite, sodium hydroxide, potassium hydroxide, calcined calcium, hydrochloric acid, acetic acid, peracetic acid, citric acid, fumaric acid, ozone, etc. Considering the influence of the remaining residue on the flavor of the final product, the washing solution is preferably water. The temperature of the washing solution is preferably 25°C or less.

<Water removal (S20)>
The purpose of dehydrating a glucosinolate-containing plant is to suppress the loss of glucosinolate during heating, which will be described later. For this purpose, the time of dehydration is before heating. The method of dehydration is not particularly limited, and includes leaving the plant to stand, blowing air, cold air, hot air, centrifugation, vacuum suction, and the use of moisture-absorbing materials or combinations thereof. From the viewpoint of suppressing the decrease in glucosinolate, blowing air, cold air, or hot air is preferable. In the case of methods that can physically damage the plant body, such as centrifugation or hot air at 70°C or higher, myrosinase present in the plant body may be activated, and glucosinolate may be decomposed.

<Heating (S30)>
The purpose of heating glucosinolate-containing plants is to sterilize and inactivate enzymes present in the plant body, especially myrosinase. When plant cells are destroyed by cutting, crushing, etc., myrosinase present in the plant body is released and activated, and breaks down glucosinolates. The broken down glucosinolates become isothiocyanates and glycosides. Isothiocyanates have various functionalities as described below, but are highly volatile and therefore less stable.
Therefore, in foods and beverages, it is preferable to maintain it in the highly stable state of glucosinolate.

The heating method is non-immersion heating. Non-immersion heating refers to heating in which the object to be heated is not immersed (for example, in a water bath, a hot bath, etc.). Specific aspects of non-immersion heating are preferably one or more of dry heat (including hot air heating with dry heat), steam boiling, and superheated steam boiling. In particular, steam boiling and superheated steam boiling are preferable. A method for heating a glucosinolate-containing plant generally involves blanching by immersion in hot water, but this method is not preferable because the glucosinolate in the glucosinolate-containing plant dissolves in the hot water. In addition, steam boiling with steam or superheated steam has good thermal efficiency, can reduce the heating time of the glucosinolate-containing plant, and can suppress oxidation of the components in the plant and enzyme reactions. This makes it possible to make the flavor and color of the final product preferable.

The heating target is not particularly limited as long as it is sufficient to inactivate myrosinase in the glucosinolate-containing plant. For example, the central temperature of the glucosinolate-containing plant may reach 90°C, taking into consideration that the enzyme inactivation temperature of myrosinase is about 70 to 80°C. Since the activity of the myrosinase increases at about 50 to 70°C, during heating,
It is important that the plant body passes through the temperature range as quickly as possible and reaches a temperature that inactivates myrosinase. From this viewpoint, it is preferable to carry out steam cooking with steam or superheated steam cooking. The device used for heating is not particularly limited as long as it is a known device.

<Cutting (S40)>
The purpose of cutting the glucosinolate-containing plant is to reduce the volume and improve the drying efficiency. The timing of the cutting is not particularly limited, but is preferably after heating in order to avoid activation of myrosinase due to cutting. If the cutting is performed before drying, the specific surface area of the glucosinolate-containing plant increases and the drying efficiency improves. In addition, it is preferable to cut after drying in order to avoid the outflow of glucosinolate due to cutting. The method of cutting is not particularly limited. Examples include a slicer, a micro grader, a dice cutter, a comitrol, a food processor, etc. The size of the glucosinolate-containing plant after cutting is not particularly limited, but is 0.5 mm to 5 cm. It is preferably 0.5 mm to 10 mm, more preferably 0.5 mm to 5 mm.

<Drying (S50)>
The purpose of drying glucosinolate-containing plants is to reduce volume and weight, and to improve storage stability. By removing moisture through drying, the volume and weight are reduced, and handling is improved. In addition, by removing moisture, water activity is reduced and bacterial growth is suppressed, improving storage stability. At the same time, changes in components, including glucosinolates, in glucosinolate-containing plants are suppressed, improving the stability of nutritional components, etc.

From the viewpoint of the above purpose, the drying is preferably performed after heating and preferably before grinding. If the drying is performed before heating, myrosinase may be activated when the cells in the glucosinolate-containing plant are destroyed during drying.

The drying method is not particularly limited, and may be, for example, one or a combination of two or more of hot air drying, cold air drying, freeze drying, and reduced pressure drying.
From the viewpoint of increasing the bulk density of the glucosinolate-containing plant powder, it is preferable to at least perform hot air drying. By increasing the bulk density of the glucosinolate-containing plant powder, when mixed with water, it becomes easy to settle in water and the dispersibility is improved. From the viewpoint of improving the color tone and flavor of the glucosinolate-containing plant, it is preferable to perform freeze drying.

The degree of drying is not particularly limited, but from the viewpoint of the above-mentioned purpose, the moisture content is preferably 8.0% by weight or less.
It is preferable that the water content is about 5.0% by weight or less. More preferably, the water content is 5.0% by weight or less.

<Crushing (S60)>
The purpose of crushing a glucosinolate-containing plant is to reduce the volume and improve dispersibility in water. From the viewpoint of the above purpose, the crushing is preferably performed after heating, and more preferably after drying or simultaneously with drying. If the crushing is performed before heating,
Myrosinase in glucosinolate-containing plants is activated, breaking down the glucosinolates. Also, grinding before drying produces a liquid or puree, but drying produces a solid mass that must be ground again after drying.

The pulverization method is not particularly limited, and may be performed by one or a combination of two or more of a pin mill, a cutter mill, a jet mill, an Orient mill, a ball mill, etc. The pulverization may be performed in one stage or in two or more stages.

The degree of pulverization is not particularly limited, but from the viewpoint of the above-mentioned purpose, the particle diameter d10 is preferably 25 μm.
It is preferable that the d50 is 50 μm or less, and the d90 is 130 μm or less. It is also preferable that the volume average diameter (MV) is about 60 μm or less. More preferably, the particle diameter is d10 of 5 μm or more and less than 20 μm, d50 of 20 μm or more and less than 50 μm, and d90 of 50 μm or less.
The particle size is preferably from 100 μm to 100 μm. The mean volume diameter (MV) is more preferably from 20 to 50 μm. If the particle size after pulverization is large, the solid content of the glucosinolate-containing plant does not disperse in water, and floats on the water surface or sinks in the water.

<Granulation (S70)>
The purpose of granulating the glucosinolate-containing plant powder is to improve the flowability of the powder and improve its dispersibility in water. From the viewpoint of this purpose, the timing of granulation is after grinding. The smaller the particle size of the glucosinolate-containing plant powder, the lower the flowability of the powder. This leads to poor handling. In addition, when the particle size of the glucosinolate-containing plant powder is small, it is likely to form lumps when mixed with water and is difficult to disperse. Therefore, dispersibility is improved by granulating with an excipient such as dextrin. In addition, by grinding the dried product of the glucosinolate-containing plant to reduce the particle size and then granulating, it is unlikely to form lumps when mixed with water, and the granulated lumps are loosened in water, the particle size is reduced, and the dispersibility in water is improved and it is unlikely to settle.

The granulation method is not particularly limited, and examples thereof include stirring granulation, dry granulation, extrusion granulation, and fluidized bed granulation. From the viewpoint of improving dispersibility in water (disintegration of particles when mixed with water), the granulation method is
Fluidized bed granulation is preferred. By carrying out the fluidized bed granulation, the adhesion between the fine powder particles becomes relatively weak, the disintegration property of the powder increases, and the dispersibility in water increases.

A known granulation device can be used. The granulation conditions are not particularly limited as long as the granulation is performed to obtain a desired particle size.

The binder used during granulation is not particularly limited, and examples thereof include known excipients, water, plant juices and extracts, etc. From the viewpoint of increasing the glucosinolate content of the glucosinolate-containing plant powder after granulation, the binder is preferably water or a glucosinolate-containing liquid.

<Sterilization and filling (S80)>
In addition to the above, the present method appropriately employs sterilization and filling. The sterilization method may be a known method, for example, sterilization using superheated steam. The sterilization method may be a continuous method, a batch method, or the like. The sterilization conditions are in accordance with various standards (company standards, industry standards, etc.). The filling method may be a known method. Here, the container is sealed. The container into which the glucosinolate-containing plant powder is filled (packed) may be a known one, for example, an aluminum packaging bag.

<Cruciferous vegetables>
Cruciferous vegetables are vegetables whose academic classification is the Brassicaceae family. Examples of cruciferous vegetables include cabbage, broccoli, kale, petit vert, raphanobrassica, watercress, komatsuna, bok choy, radish sprouts, cauliflower,
These include Chinese cabbage, turnip, takana, kohlrabi, etc. The glucosinolate-containing plant powder may be made from all or part of the Brassica vegetable (flowers, leaves, stems, etc.),
Sprouts and seeds can also be used. The glucosinolate-containing plant powder used in this study is:
Of these cruciferous vegetables, one or more may be used, but from the viewpoint of high glucosinolate content, kale or raphanobrassica is preferable.

<Glucosinolate>
Glucosinolates are derivatives of glucose and amino acids, and are a group of organic compounds containing sulfur and nitrogen, as shown by the structural formula 1. The glucosinolates in the present invention are not particularly limited, but examples thereof include glucoraphanin (also called sulforaphane glucosinolate), sinigrin, glucoerucin, glucobrassicin, glucoraphenin, glucoraphasatin, and phenethyl glucosinolate, and in the present invention, glucoraphanin is particularly preferred. Among these glucosinolates, one
Alternatively, a plurality of types may be used.

In the glucosinolate-containing plant powder according to the present invention, the content of glucosinolate is preferably 5 mg or more per gram of the glucosinolate-containing plant powder, more preferably 7 mg or more per gram of the glucosinolate-containing plant powder. In addition, in the glucosinolate-containing plant powder according to the present invention, glucoraphanin (hereinafter also referred to as "GR").
The content of ) is preferably 5 mg or more per gram of glucosinolate-containing plant powder, and more preferably 7 mg or more per gram of glucosinolate-containing plant powder.

<Myrosinase>
Myrosinase is an enzyme that hydrolyzes the glycoside bond of an isothiocyanate glycoside (such as sinigrin) and releases a sulfate group to generate an isothiocyanate from a glucosinolate. In the glucosinolate-containing plant powder according to the present invention, the myrosinase activity is preferably less than 1 unit/g, and more preferably there is no myrosinase activity. No myrosinase activity means that the myrosinase activity is 0 unit/g in the measurement of myrosinase activity described below.

<Myrosinase activity>
Myrosinase activity is the enzyme activity that converts glucosinolates to isothiocyanates (
Myrosinase activity (unit/g) is calculated by reacting myrosinase with a substrate, glucosinolate, measuring the glucosinolate or isothiocyanate content at regular intervals, and then calculating the change based on this.

The glucosinolate content and isothiocyanate content can be measured by a method known to those skilled in the art. For example, HPLC (high performance liquid chromatography) can be used. A specific method for measuring glucosinolates is the method of Fahey et al.
al., Proc. Natl. Acad. Sci. USA, 94, 10367-10372, 1997), and the ITC can be measured according to the method of Han et al. (Han et al., Int. J. Mol. Sci., 12,
This can be done according to, for example,

Myrosinase activity (unit/g) can be evaluated by measuring the content of isothiocyanate converted from glucosinolate by the reaction of myrosinase. Specifically, it can be calculated by the following formula.

<Isothiocyanate>
Isothiocyanate is a general term for substances with the structure shown in Chemical Formula 2, and is found in large quantities in Brassicaceae plants. Although isothiocyanates are useful components from the viewpoint of functionality, they are unstable due to their volatility and may disappear over time. Therefore, when ingested, they are preferably converted to isothiocyanates immediately before ingestion or within the body. Therefore, it is considered preferable that they are in the form of highly stable glucosinolates in foods and beverages.

Here, sulforaphane is a type of isothiocyanate, and is a substance that is generated when glucoraphanin is hydrolyzed by myrosinase. It is preferable that the glucosinolate-containing plant powder according to the present invention is substantially free of sulforaphane.
"Substantially free of sulforaphane" means that the sulforaphane content in the glucosinolate-containing plant powder according to the present invention is less than 0.1 mg/100 g. It can be understood that the low sulforaphane content in the glucosinolate-containing plant powder according to the present invention is one result indicating that there is little reaction by myrosinase in the processing step of the glucosinolate-containing plant.

<Glucosinolate-containing liquid composition>
The glucosinolate-containing liquid composition according to the present invention is a liquid containing at least glucosinolate. Specifically, it is a squeezed juice, extract, or concentrate thereof from a glucosinolate-containing plant, as well as a water-dissolved solution of glucosinolate, etc. The solvent of the glucosinolate-containing liquid composition according to the present invention is not particularly limited, but is preferably water.

<Other ingredients>
The glucosinolate-containing plant powder according to the embodiment of the present invention may contain other raw materials in addition to those made from glucosinolate-containing plants. Specifically, the raw materials include vegetable powders other than those of cruciferous vegetables, food additives, etc. Preferably, the raw materials include a myrosinase-containing composition.

A myrosinase-containing composition is a composition that contains at least myrosinase. By containing a myrosinase-containing composition, myrosinase hydrolyzes glucosinolates during consumption to generate isothiocyanates, improving the utilization efficiency of isothiocyanates in the body. The form of the myrosinase-containing composition is preferably in a dried state, for example, in powder form. This is because the glucosinolate-containing plant powder composition is stored so that the myrosinase does not react with the glucosinolates in the green powder. Examples of myrosinase-containing compositions include dried and crushed mustard seeds.

Examples of food additives include sweeteners, acidulants, nucleic acids, spice extracts, colorants, pH adjusters, antioxidants, preservatives, emulsifiers, nutritional enhancers, thickeners, excipients, etc. In realizing the present invention, the flavor and
From the standpoint of glucosinolate content, it is preferable to refrain from using food additives as much as possible.

<Particle size>
The particle size is the value measured for the long diameter of the particle. Here, the "cumulative a% particle size" is the cumulative frequency calculated in the particle size distribution obtained by measurement, with the total volume of the particle group being 100%,
The cumulative frequency of a particle is defined as the particle diameter at which the cumulative frequency reaches a %. In other words, the cumulative 10% particle diameter (d10) refers to the particle diameter at which the cumulative frequency is 10%. The cumulative 50% particle diameter (d50) refers to the particle diameter at which the cumulative frequency is 50%. The cumulative 90% particle diameter (d90) refers to the particle diameter at which the cumulative frequency is 90%.
The particle size at the point where the volume average diameter is 1/1000 is called the "Volume Average Diameter."
Hereinafter, this is also referred to as "MV." The term "MV" refers to the volume-weighted average particle size of a particle group. The means for measuring particle size is a laser diffraction/scattering type particle size distribution measuring device.

The particle size of the glucosinolate-containing plant powder in the present invention is not particularly limited, but preferably, the particle size after grinding of the glucosinolate-containing plant is d10 of 25 μm or less, d50
It is preferable that the volume average diameter (M
It is preferable that the particle diameter d10 is about 5 μm or less.
d50 is 20 μm or more and less than 50 μm, d90 is 50 μm or more and less than 100
The mean volume diameter (MV) is preferably about 20 μm or more and about 50 μm or less. In addition, the particle diameter of the glucosinolate-containing plant powder after granulation is preferably d10 of 30 μm or more, d50 of 60 μm or more, and d90 of 100 μm or less.
The volume mean diameter (MV) is preferably 60 μm or more. More preferably, d10 is less than 60 μm, d50 is less than 100 μm, and d90 is less than 20 μm.
The particle diameter is preferably 0 μm or less. The volume average diameter (MV) is more preferably 70 μm or more and 100 μm or less. By reducing the particle diameter, the properties become smoother and the particles can be easily applied to various products. The method for reducing the particle diameter may be a known method, but specifically,
Examples of the method include pulverization and micronization using a pulverizer and a finer processor, and fractionation using a sieve.

<Color tone>
In accordance with the present invention, color tone refers to a color characteristic, including lightness, hue, and saturation. In the present invention, color tone is generally defined as L
The L*a*b* (L star, A star, B star) color system is used. The indices of the L*a*b* color system are lightness (L value), chromaticity (hue and saturation) (a value, b value). The method for measuring color tone may be a known method. Measuring devices are commercially available. An example of a measuring means is a color difference meter SP
The camera is an ECTROPHOTOMETER CM-5 (manufactured by Konica Minolta).

The a-value indicates the chromaticity of green, and the lower this value, the closer to green the color is. Also, glucosinolate-containing plants contain enzymes, but if they are crushed or squeezed without being inactivated by heating, or if oxidation is promoted by applying excessive heat, the color will turn brown, the lightness (L-value) will decrease, or the chromaticity of green will decrease (i.e., the a-value will increase).

The color tone of the glucosinolate-containing plant powder of the present invention is not particularly limited, but from the above viewpoints, preferably, the L value is 15 or more and 25 or less, the a value is -5.5 or more and -3 or less, the b value is 9 or more and 12 or less, and the a/b value is -0.7 or more and -0.3 or less.

<Bulk density>
The bulk density is a value obtained by dividing the weight of a powder by the volume, including the voids between particles, of a powder filled in a container of a certain volume in a certain manner, and is expressed in units of g/ml. The bulk density according to the embodiment of the present invention is loose bulk density. A known bulk density measuring device can be used as a measuring device.

The bulk density of the glucosinolate-containing plant powder after granulation according to the present invention is not particularly limited, but is preferably 0.3 or more and 1.0 or less. If the bulk density is low, when mixed with water, the powder floats on the water surface and is difficult to sink in water, resulting in low dispersibility in water.
The bulk density can be increased by granulation or by at least heat drying during drying. In addition, by having the bulk density in the above range, the packing ability into a container is improved.

<Dispersibility>
The dispersibility according to the embodiment of the present invention refers to the dispersibility of the glucosinolate-containing plant powder according to the present invention in water. Dispersion refers to a state in which the dispersed phase is suspended in the dispersion medium. High dispersibility refers to a state in which the dispersed phase is unlikely to settle and is highly stable when suspended in the dispersion medium. Low dispersibility refers to a state in which the dispersed phase is unlikely to diffuse in the dispersion medium and therefore is likely to settle, and is low in stability when suspended in the dispersion medium. In the present invention, the dispersed phase in the dispersion is a solid, and the dispersion medium is a liquid. Specifically, the dispersed phase in the present invention is a glucosinolate-containing plant powder, and the dispersion medium is a water-soluble substance, particularly water. From the above perspective, in order to increase dispersibility, it is effective to reduce the particle size of the dispersed phase.
However, it was found that the smaller the particle size of the glucosinolate-containing plant powder according to the present invention, the more likely it is to form lumps when mixed with water, and the lower the dispersibility. Therefore, by granulating the glucosinolate-containing plant powder, the particle size increases before mixing with water, increasing the bulk density of the glucosinolate-containing plant powder and making it less likely to form lumps,
When mixed with water, the granulated powder disintegrates, reducing the particle size of the glucosinolate-containing plant powder in water and increasing dispersibility.

From this viewpoint, it is preferable that the particle size of the glucosinolate-containing plant powder after granulation is as described above. In addition, the particle size after mixing with water is d10 of 25 μm or less, d50 of 5 μm or less, and
It is preferable that the average particle size (MV) is 100 μm or less, and the average particle size (d90) is 130 μm or less.
More preferably, the particle diameter is d10 of 5 μm or more and less than 20 μm, d50 of 20 μm or more and less than 50 μm, and d90 of 50 μm or more and 100 μm.
The mean diameter by volume (MV) is preferably about 20 μm or more and 50 μm or less. In addition, in order to increase the disintegrability of the glucosinolate-containing plant powder after granulation, the granulation method used for granulation is preferably fluidized bed granulation, and the binder is preferably water or a glucosinolate-containing liquid composition.

[Tests on whether or not water is removed, and on the order of cutting and steaming]
<Comparative Example 1>
100 kg of Raphanobrassica (Kälisch) was washed with water and then cut into pieces of about 2.0 cm x 1.5 cm using a slicer. Then, it was boiled at 100°C in a steaming facility.
The product was heated by steam heating at 40°C for 5 minutes (reaching a product temperature of 90°C), and then cooled to below 70°C by blowing cold air. The product was semi-dried by hot air drying at 65°C for 40 minutes, and then freeze-dried at a shelf temperature of 60°C to 70°C for 24 hours to obtain a dried Raphanobrassica product.

Example 1
After washing with water, 100 kg of Raphanobrassica was heated by steam heating at 100°C for 5 minutes (reaching a product temperature of 90°C), and cooled to below 70°C by blowing cold air. It was then cut into pieces of about 2.0 cm x 1.5 cm using a slicer. This was semi-dried by hot air drying at 65°C for 40 minutes, and then freeze-dried to 60-70°C.
The mixture was dried at 37° C. for 24 hours to obtain dried Raphanobrassica.

Example 2
After washing 100 kg of Raphanobrassica with water, the moisture adhering to the Raphanobrassica was removed by air blowing, and the product was heated by steam heating at 100°C for 5 minutes (product temperature reached 90°C), and cooled to below 70°C by blowing cold air. The product was then cut into pieces of about 2.0 cm x 1.5 cm using a slicer. The pieces were then dried with hot air at 65°C and 100°C.
After semi-drying for 40 minutes, the mixture was freeze-dried at 60°C to 70°C for 24 hours to obtain dried Raphanobrassica.

<Measurement of glucoraphanin content> The glucoraphanin content was measured using HP under the following conditions.
The analysis was carried out by LC method.
Apparatus: ACQUITY UPLC H-Class System (Waters)
Column: ACQUITY CSH C18 (Φ2.1×100 mm, 1.7 μm) (Wa
(Manufactured by TERS)
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: 5 min. Maintain 0% mobile phase B
Linear gradient of mobile phase B from 0 to 10% in 10 minutes
Linear gradient from 10% to 100% mobile phase B in 5 minutes
Maintain 100% mobile phase B for 5 minutes
Linear gradient from 100% to 0% mobile phase B in 2 minutes
Maintain 0% mobile phase B for 5 minutes Flow rate: 0.1 mL/min
Detection wavelength: 235 nm
The glucoraphanin content was calculated from the glucoraphanin concentration in the sample obtained by HPLC analysis and the amount of the sample subjected to extraction.

<Measurement of moisture content and solid content>
The moisture content and solid content were measured by a normal pressure heating and drying method.
The samples were heated at 5° C. for 4 hours, and the moisture content was calculated from the ratio of the weight of the sample before heating to the weight loss before and after heating. The solid content was measured from the ratio of the weight of the sample before heating to the weight of the sample after heating.

<Glucoraphanin (GR) yield>
The yield of glucoraphanin was calculated according to the following formula.
GR yield (%) = 100 × (solid amount of fresh vegetables) × (GR concentration in dried vegetables) / (
(solid amount of dried vegetables) x (GR concentration in fresh vegetables)

<Results>
The results are shown in Table 1. The moisture content, solid amount, and GR concentration were measured for the raw material, fresh Raphano brassica, and Comparative Example 1, Example 1, and Example 2, and the GR yield of each sample was calculated. By performing the cutting process after the heating process, the GR yield increased by 3% (comparison between Example 1 and Comparative Example 1). In addition, by dehydrating fresh Raphano brassica after washing, the GR yield increased by 9% (comparison between Example 1 and Example 2).

<Summary and Consideration>
The reason why cutting after heating resulted in a higher GR yield than cutting after heating is thought to be that heating causes GR to flow out of the plant from the cut surface, and cutting before heating activates myrosinase at the cut surface, which degrades GR.

The reason why GR yield increased when water was removed after washing was thought to be that if water remained on the Raphanobrassica when it was heated, the GR would be washed away.

[Test using water binder granulation]
<Comparative Example 2>
Rafano brassica was heated at 70°C and 180°C in a steam convection oven (Fujimak Co., Ltd.).
After drying for 10 minutes, the mixture was subjected to primary pulverization using a pin mill (manufactured by Nara Machinery Works, Ltd.) to obtain Comparative Example 2.

<Comparative Example 3>
Rafano brassica was heated at 70°C and 180°C in a steam convection oven (Fujimak Co., Ltd.).
After drying treatment under conditions of 1000 min, the mixture was subjected to primary pulverization using a pin mill (manufactured by Nara Machinery Works) and secondary pulverization using a jet mill (Seishin Enterprise Co., Ltd.) to obtain Comparative Example 3.

Example 3
Rafano brassica was heated at 70°C and 180°C in a steam convection oven (Fujimak Co., Ltd.).
After drying for 1 hour under the conditions of 10 minutes, the mixture was first pulverized using a pin mill and then secondarily pulverized using a jet mill. To the mixture, 5% by weight of Fibersol 2 (manufactured by Matsutani Chemical Industry Co., Ltd.), which is a resistant dextrin, was added as an excipient, and 2% by weight of water was added, and the mixture was stirred and granulated for 1 minute using a mixer. The mixture was then passed through a sieve with 500 μm openings and dried at 50° C. for 1 hour, which was designated as Example 3.

Example 4
Raphano brassica was dried using steam convection at 70°C for 180 minutes, then primarily ground using a cutter mill and secondarily ground using a jet mill, and the resulting mixture was granulated in a fluidized bed granulator using water as a binder to prepare Example 4.

<Particle size measurement>
The particle size was measured using a Microtrac MT3300EX (manufactured by Microtrac Bell Co., Ltd.) As the solvent during measurement, ethanol was used to measure the powder particle size before dispersion in water, and water was used to measure the particle size after dispersion in water.

<Dispersibility evaluation>
The dispersibility in water of each powder sample was evaluated. 3.0 g of the powder sample was mixed in 100 ml of water, and the degree of dispersion was confirmed. The dispersibility was evaluated as follows.
A: Easily dispersible and not prone to settling in water B: Easily dispersible, but prone to settling in water C: Disperses with thorough stirring D: Tends to form lumps and is difficult to disperse E: Does not disperse even when thoroughly stirred The degree of dispersibility is rated in the order of A to E, with A being the highest dispersibility and E being the lowest dispersibility.

<Results>
The results are shown in Table 2. It was confirmed that the powder that had been granulated (Example 3) had improved dispersibility compared to the powder before granulation (Comparative Example 3). On the other hand, it was found that the particle size was not sufficiently small in water when the sample of Example 3 was mixed with distilled water. Therefore, the water and solid parts were separated and became non-uniform after being left for only a few minutes. It was confirmed that the particles were separated and the powder returned to its original particle size by applying a physical stimulus of ultrasonic waves thereafter. From this, it was found that the powder and excipient were not separated from the sample of Example 3 by only mixing with water. By performing the granulation method using a fluidized bed granulation method and using water as a binder, it was possible to produce a highly dispersible green powder that had a large particle size before granulation but became small in water when mixed with water (Example 4). From the above, it was found that it is important to perform fine grinding and granulation treatment of the particles in order to improve the dispersibility of the green powder. In particular,
It was found that a fluidized bed granulation method is effective for the granulation method, and that by using water as a binder, a glucosinolate-containing plant powder with a high glucosinolate content can be produced.

[Confirmation of glucosinolate residual rate, myrosinase activity, and sulforaphane content]
Example 5
After washing with water, 100 kg of Raphanobrassica was heated by steam heating at 100°C for 5 minutes (reaching a product temperature of 90°C), and cooled to below 70°C by blowing cold air. It was then cut into pieces of about 2.0 cm x 1.5 cm using a slicer. This was semi-dried by hot air drying at 65°C for 40 minutes, and then freeze-dried to 60-70°C.
The mixture was dried at 37° C. for 24 hours to obtain dried Raphanobrassica.

<Measurement of glucoraphanin content>
The glucoraphanin content was measured by HPLC under the following conditions.
Apparatus: ACQUITY UPLC H-Class System (Waters)
Column: ACQUITY CSH C18 (Φ2.1×100 mm, 1.7 μm) (Wa
(Manufactured by TERS)
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: 5 min. Maintain 0% mobile phase B
Linear gradient of mobile phase B from 0 to 10% in 10 minutes
Linear gradient from 10% to 100% mobile phase B in 5 minutes
Maintain 100% mobile phase B for 5 minutes
Linear gradient from 100% to 0% mobile phase B in 2 minutes
Maintain 0% mobile phase B for 5 minutes Flow rate: 0.1 mL/min
Detection wavelength: 235 nm
The glucoraphanin content was calculated from the glucoraphanin concentration in the sample obtained by HPLC analysis and the amount of the sample subjected to extraction.

<Measurement of moisture content and solid content>
The moisture content and solid content were measured by a normal pressure heating and drying method.
The samples were heated at 5° C. for 4 hours, and the moisture content was calculated from the ratio of the weight of the sample before heating to the weight loss before and after heating. The solid content was measured from the ratio of the weight of the sample before heating to the weight of the sample after heating.

<Glucoraphanin (GR) yield>
The yield of glucoraphanin was calculated according to the following formula.
GR yield (%) = 100 × (solid amount of fresh vegetables) × (GR concentration in dried vegetables) / (
(solid amount of dried vegetables) x (GR concentration in fresh vegetables)

<Measurement of sulforaphane (SFN) content>
The SFN content was measured by HPLC under the following conditions.
Apparatus: ACQUITY UPLC H-Class System (Waters)
Column: ACQUITYBEH C18 (Φ2.1×50 mm, 1.7 μm) (Wat
(Manufactured by ERS)
Column temperature: 35°C
Sample injection volume: 10 μL
Mobile phase: ultrapure water:acetonitrile = 80:20 (v:v)
Flow rate: 0.2mL/min
Detection wavelength: 202 nm
The SFN content was calculated from the SFN concentration in the sample obtained by HPLC analysis and the amount of the sample subjected to extraction.

<Measurement of myrosinase activity>
Myrosinase activity (unit/g) was evaluated by measuring the amount of SFN converted from GR by the reaction of myrosinase. Specifically, it was calculated according to the formula shown in [Equation 1] above.

The myrosinase reaction of dried Raphanobrassica was carried out as follows: GR content 2.0
100 ml of 33 mM phosphate buffer (pH 7.0) adjusted to 100 mg/ml was placed in a stoppered Erlenmeyer flask and incubated at 37°C in a water bath. The dried Raphano Brassica was added to the previously prepared GR solution, mixed well, and the myrosinase reaction was initiated in a water bath at 37°C. 10, 20, and 30 minutes after the start of the reaction, 100 μL each was collected from the reaction solution, mixed with 20 μL of 20% trifluoroacetic acid solution, and stored on ice. After the entire reaction solution had been collected, 0.4 mL of ethyl acetate was added and mixed well. The resulting solution was centrifuged (1000 x g, 4°C, 5 minutes), and 200 μL of the collected supernatant was centrifuged (40
The mixture was dried at 4° C. for 20 minutes. 250 μL of ultrapure water was added, and the dried product was redissolved by ultrasonic treatment. The mixture was centrifuged, and the collected supernatant was used as an HPLC sample for measuring the SFN content.

<Color Tone Measurement>
The analytical instruments and conditions for measuring the color tone are as follows: Each sample was placed in a 30 mm dedicated petri dish and the measurement was carried out.
(Analytical equipment) Spectrophotometer CM-5 type (Konica Minolta)
(Measurement conditions) Regular reflection treatment: SCE
Measurement method: reflectance measurement
Measurement diameter: 30 mm
Light source: D65
Field of view: 10°
Color system: L*a*b*

<Results>
By using a manufacturing method in which Raphanobrassica is treated with steam heating, the yield of glucoraphanin from processing was increased to about 90% (Table 3). The color tone of the dried Raphanobrassica is shown in Table 4. In addition, there was no myrosinase activity, and no sulforaphane was found to be present. The glucoraphanin concentration was 1.01
From fresh Raphanobsracica with a glucoraphanin concentration of 7 mg/g or more, dried Raphanobsracica was obtained with a glucoraphanin concentration of 7 mg/g or more.

The field in which this invention is useful is the production and sale of glucosinolate-containing plant powders.

Claims (4)

A method for producing a glucosinolate-containing plant powder, comprising at least the following steps:
Water removal: The glucosinolate-containing plants are dehydrated, and the water removal method is blowing air, cold air, hot air (excluding those above 70°C) , or using moisture-absorbing materials or a combination of these.
Non-immersion heating: Here, the dehydrated glucosinolate-containing plant is heated by non-immersion heating, and the heating medium used in the non-immersion heating is one or more of steam and superheated steam;
Drying: Here it is the non-immersed heated glucosinolate-containing plant that is dried. The method of claim 1 further comprising the steps of:
Cutting: Here, it is the non-immersed heated glucosinolate-containing plant that is cut. The method of claim 1 or 2 further comprises the steps of:
Grinding: Here, it is the non-soaked, heated glucosinolate-containing plant that is ground. The manufacturing method according to any one of claims 1 to 3, wherein the glucosinolate-containing plant is a cruciferous vegetable.

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