JP6653554B2 - Method for producing citrus peel ground paste - Google Patents

Description

  The present invention relates to a paste obtained by using citrus peel (also referred to simply as “citrus peel”) as a raw material and grinding the paste. In addition, the present invention relates to a method for producing the ground paste, and foods and beverages containing the ground paste.

  It has long been known that citrus peel contains many components that are good for the body. For example, chimp (dried citrus peel) used as a Chinese medicine is famous. The effects of the above-mentioned thimpi include an anti-allergic action, an anti-viral action, an anti-inflammatory action, a tracheal contraction suppression, a sedation action, a central nervous system suppression action and the like. The main components contained in the citrus peel include citrus flavonoids (hesperidin, narilutin, nobiletin), pectin, limonene, and the like. These components (hesperidin and naringin) cause the above antiallergic, antiviral and antiinflammatory effects. And so on. In addition to the chimpanzee, immature fruits are crushed and powdered together with their skins, flavonoids are extracted as typical active ingredients, or flavonoids are aglyconized, and sugar is transferred to flavonoids. However, there is an example in which a material having improved water solubility is used.

  Conventionally, Patent Literature 1 and Patent Literature 2 have been proposed as techniques relating to pastes and functional foods containing citrus peel. In Patent Document 1, as a method for producing the paste, a predetermined amount of water is added to a washed citrus fruit, the fruit and water are boiled under pressure, and a solution containing a fruit extract is mixed with a softened citrus fruit. A step of producing a fruit, a step of putting the solution containing the softened citrus fruit and the fruit extract into a mixer and crushing and mixing, and a solution containing the finely crushed citrus fruit and the fruit extract Into a copper kettle, boiling while stirring, and concentrating the solution to obtain a fruit paste.

  Patent Literature 2 describes, as a food or beverage containing a lemon-derived flavonoid aglycone, a food or beverage obtained by subjecting the lemon-derived flavonoid glycoside to glycosidase treatment.

JP 2006-121950 A Japanese Patent No. 4335555

  Patent Document 1, as described above, describes a method for producing a paste containing pericarp-derived components by boiling and concentrating a solution obtained by pulverizing fruits including pericarp with a mixer, and producing industrial waste. It describes a beverage containing the nutrient portion contained in the citrus fruit without producing it. However, no operation has been performed to increase the absorbability of the flavonoids, and the utilization efficiency of the flavonoids contained therein is considered to be low.

  In addition, Patent Document 2 describes a food or beverage containing a flavonoid aglycone obtained by performing a step of treating a lemon-derived flavonoid glycoside with glycosidase as described above. However, Patent Document 2 does not specify the amount of aglycone. Further, in Examples of Patent Document 2, eriodictyol and diosmetin contained in the water extract of lemon peel are aglyconized, and the flavor and other components of the skin are not mentioned.

  The present invention has been made in order to address such a problem, has a flavor unique to citrus, and has a high absorbency of flavonoids, a high-performance citrus peel paste, a method for producing the same, and a mixture thereof. The purpose is to provide food and drink.

The citrus peel milling paste of the present invention is a citrus peel milling paste, the milling paste contains the citrus peel-derived flavonoid aglycone, the aglycone represented by the following formula abundance ratio is It is at least 90 mmol%.
Aglycone abundance ratio (mmol%) = (mol number of the aglycone / total mole number of the aglycone and the glycoside of the aglycone) × 100

  The ground paste contains at least one selected from hesperetin and naringenin as the aglycone.

  The ground paste contains two or more kinds of the aglycones, and the aglycone abundance ratio of each is 90 mmol% or more.

  The method for producing a citrus peel grinding paste of the present invention is the above-described method for producing a citrus peel grinding paste of the present invention described above. (1) Water is added to citrus peel, which is a residue after squeezing juice from citrus fruits. (2) enzymatic treatment of the flavonoid glycoside contained in the ground material of the pericarp to produce the aglycone. .

  The paste contains hesperetin and naringenin as the aglycone. In the enzymatic degradation step, β-glycosidase at a weight ratio of 0.05% or more is added to the paste, and the enzyme treatment is performed at 45 ° C to 60 ° C for 8 hours or more. Is performed.

  The food and drink of the present invention is characterized by containing the above-mentioned citrus peel grinding paste of the present invention (including the one obtained by the above-mentioned production method).

  The citrus peel milling paste of the present invention is a citrus peel milling paste, which contains flavonoid aglycone derived from citrus peel and has an aglycone represented by a predetermined formula of 90 mmol% or more. It has a unique flavor and high flavonoid absorption.

  In the method for producing a ground citrus peel paste of the present invention, the flavonoids contained therein are aglyconeized at a high conversion rate while leaving various active ingredients and flavors. As a result, it is possible to use a large part of the citrus peel whose use has been limited so far, and it is highly economical, has a flavor unique to citrus, and has a high absorption of flavonoids. Can be manufactured.

  Since the food and drink of the present invention contains the citrus peel ground paste, various high-performance effects resulting from the flavonoids can be obtained.

It is a flowchart of the manufacturing process of the citrus peel grinding paste of this invention. It is a schematic diagram of an intestinal absorption test using Caco-2 cells.

  As described above, citrus peel (peel) contains citrus flavonoids (hesperidin, narirutin), pectin, limonene, and the like as main components, and when taken orally, has an antiallergic effect, an anti-inflammatory effect, and a trachea. Suppression of contraction, sedation and central nervous system suppression are obtained. However, citrus peels are not easily eaten and their use is limited. In addition, most of the citrus flavonoids in the pericarp are glycosides, and after ingestion, sugars are cut off by intestinal bacteria, aglyconeized, and then absorbed into the body, thereby exhibiting efficacy. However, intestinal bacteria vary from person to person and may be difficult to be absorbed. In view of such a point, the citrus peel grinding paste of the present invention converts the citrus peel into a grinding paste and aglycones the flavonoid glycosides contained therein at a high conversion rate. This makes it possible to use a large part of the citrus peel whose use has been limited so far, and to obtain a highly functional citrus peel ground paste having high economic efficiency and high flavonoid absorption.

  The citrus peel grinding paste of the present invention is a citrus peel grinding paste. Citrus fruits are mainly composed of juice, peels (albedo, flavedo), carbohydrates, and sorghum. The grinding paste of the present invention mainly uses pericarp as a material. More specifically, as shown in the later-described paste-forming step, it is preferable to use pericarp, which is a juice residue after squeezing juice from citrus fruits. In addition to the pericarp, the residue contains carcinoma membrane, seeds, cinnamon, and unsqueezed juice (very little).

  Conventionally, flavonoid glycosides contained in citrus fruits are often used after being purified after extraction using a solvent such as water or alcohol (methanol or ethanol). In addition, a crushed dried product may be used as the citrus peel. On the other hand, in the present invention, citrus peel (residue of squeezed fruit) was used as a raw material without drying, etc., and various active ingredients and flavors were left without performing extraction operation and the like. In this state, flavonoid glycosides are aglyconated. For this reason, a flavor unique to citrus can be left in the obtained citrus peel paste.

  The citrus that can be used in the present invention can be selected from citrus belonging to the family Rutaceae, Rutaceae. For example, tanzeros such as seminols, agrifruits, tangeros, etc., citrus fruits such as shiranuhi (Dekopon), nuts cans, hassaku, hyuganatsu, sweeties, etc., oranges such as Valencia orange, navel orange, blood orange, jaffa orange, bergamot, grapefruit , Orange grapefruit, grapefruit, lemon, lime, shikuwasa, daidai, yuzu, kabosu, sudachi, bushkan, citron, etc., perfumed citrus fruits, iyokan, tankan, etc. Mandarins such as mandarin orange, ponkan and Kishu mandarin, and kumquats such as kumquat. These citrus fruits as raw materials may be used alone or in combination of two or more.

  The flavonoid glycoside has a structure in which a flavonoid aglycone and a monosaccharide or a disaccharide are bound by a glycosidic bond. Examples of the flavonoid aglycone contained in the citrus peel grinding paste of the present invention include hesperetin (3 ', 5,7-trihydroxy-4'-methoxyflavanone), naringenin (4', 5,7-trihydroxyflavanone), and naringenin (4 ', 5,7-trihydroxyflavanone). Dictiol, diosmetin and the like. Among these, it is preferable to include at least one selected from hesperetin and naringenin, since antiallergic action, antiviral action, anti-inflammatory action and the like can be expected. Most preferably, it contains both hesperetin and naringenin.

  These flavonoid glycosides include hesperidin, which is a glycoside of hesperetin and rutinose, narirutin, which is a glycoside of naringenin and rutinose, and naringenin and neohesheridose. ), Eriocitrin which is a glycoside of eriodictiol and rutinose, diosmin which is a glycoside of diosmetin and rutinose, and the like. Is mentioned.

The citrus peel grinding paste of the present invention contains the flavonoid aglycone derived from the citrus peel, and the aglycone content ratio (molar ratio) contained in the paste, represented by the following formula, is 90 mmol% or more. Features. By the predetermined manufacturing process described later, this high flavonoid aglycone abundance ratio is realized while retaining the flavor.

Aglycone abundance ratio (mmol%) = (mol number of the aglycone / total mole number of the aglycone and the glycoside of the aglycone) × 100

Here, “the glycoside of aglycone” is a flavonoid aglycone glycoside contained in the citrus peel grinding paste, and is a component contained in the citrus peel as a raw material.

  In the case where the citrus peel grinding paste contains a plurality of types of flavonoid aglycones, the above-mentioned abundance ratio in at least one type of flavonoid aglycone may be within the above range. In order to express high functionality, it is preferable that the above-mentioned abundance ratio in all the flavonoid aglycones contained is within the above range. In particular, in the present invention, it is preferable that the above-mentioned abundance ratio of both hesperetin and naringenin, which are flavonoid aglycones, containing seminol or the like as a raw material is within the above range.

  The method for producing a citrus peel grinding paste of the present invention is the above-described method for producing a citrus peel grinding paste. FIG. 1 shows a flow chart of this manufacturing process. As shown in FIG. 1, this manufacturing process is roughly divided into (1) a paste-forming process for forming a raw material into a paste, and (2) an enzymatic decomposition process for generating aglycone.

(1) Pasting Step The pasting step can be divided into a squeezing step, a grinding step, and a filtration step when subdivided. In the squeezing step, fruit juice is squeezed from citrus fruit as a raw material. The squeezing is performed using a known squeezing machine or the like. As described above, in addition to the pericarp, the squeezed residue also includes a carcass membrane, unsqueezed fruit juice, and the like, and the next grinding step is performed as it is. It is preferable to use an inline juicer as the juicer. In-line juicer, for example, after introducing the citrus fruit as a raw material into the lower cup, lowering the upper cup, pressing the pericarp into the cavity, squeezing the fruit and squeezing the juice, (A paste material according to the present invention) is discharged out of the system.

  In the grinding process, water is first added to the pericarp, which is the juice residue. Water is added to such an extent that cutting and grinding can be performed smoothly. For example, about twice the weight of water is added. This water mixture is ground using a grinder, and if necessary, a cutter, a grinder, a stirrer, and the like. Examples of grinders and cutters that can be used include a mixer, a homogenizer, a microcutter, and a mass colloid (stone-type). The temperature at the time of grinding is room temperature. The degree of grinding is not particularly limited, but the grinding is carried out at least in the enzymatic decomposition step to such an extent that the aglyconization is possible up to the above-mentioned abundance ratio.

  In the filtration step, large fibers and the like are removed from the ground material obtained in the grinding step. The filtration is performed using a filter having a predetermined mesh (about 10 to 48 mesh). Thereby, when the paste is added to food or drink, uncomfortable feeling at the time of eating and drinking can be reduced.

(2) Enzyme Decomposition Step The enzymatic decomposition step is a step in which flavonoid glycosides contained in the ground citrus peel are subjected to an enzyme treatment so that the flavonoid aglycone has the above-mentioned abundance (90 mmol% or more). . Specific examples of the enzyme treatment include glycosidase treatment. That is, β-glycosidase is added to the paste-like triturated material to act, and the glycoside bond of the flavonoid glycoside contained therein is cleaved to produce aglycone. As the β-glycosidase, for example, a purified product using a culture supernatant of Penicillium multicolor or a cell destruction product as a starting material can be used.

  In the enzymatic decomposition step, the treatment temperature is preferably 45C to 60C, more preferably 48C to 55C. Within this temperature range, the enzyme is excellent in reaction temperature and activity, thermal stability, etc., and high effects can be expected. On the other hand, when citrus fruits are subjected to an enzyme treatment in the food field, the treatment may be performed at a temperature lower than the optimum activation temperature of the enzyme (such as less than 40 ° C.) in order to prevent the flavor and aroma from disappearing. . In the paste of the present invention, citrus peel (residue of squeezed fruit) is used as a raw material as it is, and an enzyme treatment is performed on the paste obtained by simply adding water and grinding the citrus peel. It has a moderate peel feeling.

  In this enzymatic decomposition step, the treatment time is a time that enables aglyconation up to the above-mentioned abundance ratio, which is longer than ordinary enzyme treatment, preferably 5 to 30 hours, more preferably 8 to 20 hours. This treatment is performed while maintaining the treatment temperature constant and stirring as necessary. Further, the processing container may be sealed. The amount of the enzyme to be added is 0.05% or more, preferably 0.05% to 3%, more preferably 0.08% to 1.5% by weight based on the total amount of the paste-like ground material. It is. In addition, the pH at the time of the enzyme treatment (glycosidase treatment) is preferably 3 to 6, more preferably 4 to 6, because it shows high activity. In addition, since the pH value of citrus peel (residue of fruit juice) is pH 3-4, it can be processed as it is without any particular pH adjustment.

  When hesperetin and naringenin are contained as the flavonoid aglycone, a preferable condition of the enzymatic decomposition step is to add 0.08 to 1.5% by weight of β-glycosidase to the paste and add 8 to 45 ° C to 60 ° C. It is a step of performing the enzyme treatment for a period of time to 20 hours. More preferably, 1.0% β-glycosidase is added to the paste at a weight ratio of 8 to 20 hours at 50 ° C. After the enzyme treatment, the glycosidase is inactivated.

  The food and drink of the present invention contains the above-mentioned citrus peel grinding paste of the present invention. That is, the paste is mixed with food or beverage. When added to a beverage, the components are easily and uniformly diffused by shaking a little, and the tongue at the time of ingestion is smooth and easy to drink, and has an appropriate peel feeling derived from citrus peel. Also, by kneading the paste into bread dough or the like, it is possible to appropriately give a peel feeling derived from citrus peel as described above. Also, when mixed with foods and beverages, flavors, vitamins, minerals, antioxidants, pigments, emulsifiers, preservatives, seasonings, sweeteners, fruit juices, honey, etc., as long as the purpose of the present invention is not impaired Can also be contained.

  Conventionally, the citrus peel, which has not been easily eaten, can be easily and economically and efficiently ingested by mixing the paste into a food which can be easily consumed. Looking at the domestic market in recent years, the market for functional beverages that support health is expanding, while the market for fruit and vegetable beverages is shrinking. One of the causes is competition with a beverage that claims functionality. By adding the paste to, for example, a citrus juice beverage, it is possible to enhance functionality not attributed to the additive, and to enhance marketability of the citrus juice beverage.

Comparative Example 1 and Comparative Example 2
Ingredients used: Seminole Enzyme amount: 0.01%
Processing temperature: 50 ° C
Processing time: 2, 20 hours

As a paste-forming step, 150 g of residue (mainly composed of pericarp, including a carbohydrate membrane and a small amount of fruit juice, etc., hereinafter referred to simply as "seminole juiced pericarp") after squeezing fruit juice from the fruit of Seminole 300 mL of water was added, and the mixture was cut and ground with a mixer and a homogenizer, and the fiber was removed through 32 mesh. At this time, 231 g of a paste was obtained, and the solid content recovery was 39.8%. As a result of measurement of hesperidin and narirutin as flavonoids contained in the peel after seminole squeezing, 7,069 mg / 100 g of hesperidin and 673 mg / 100 mg of narirutin were contained in the solid content. The measurement was performed by high performance liquid chromatography (HPLC). The paste after removing the fibrous material through 32 mesh contained 7,378 mg / 100 g of hesperidin and 854 mg / 100 g of narirutin in the solid content, and there was no large change in the components before and after grinding and filtration. .

  As an enzymatic degradation step, a β-glycosidase preparation (manufactured by Amano Enzyme Co., trade name: Aromase) having a weight ratio of 0.01% to the paste obtained in the above step was added, and the mixture was heated at 50 ° C. for 2 hours (Comparative Example 1). After decomposing for 20 hours (Comparative Example 2), the enzyme was inactivated by heating. Table 1 below shows the contents of hesperetin (aglycone) and hesperidin and the aglycone abundance ratio (hesperetin / (hesperidin + hesperetin) (mmol%)) in the paste, and Table 2 shows the contents of naringenin (aglycone) and narilthine and the presence of aglycone in the paste. The ratios (naringenin / (narirutin + naringenin) (mmol%)) are shown.

Examples 1 to 3 and Comparative Examples 3 to 6
Ingredients used: Seminole Enzyme amount: 0.1%
Processing temperature: 50 ° C, 40 ° C
Processing time: 1, 2, 4, 8, 16, 20 hours

In the pasting process, 1 L of water was added to 500 g of peel after seminole squeezing, and the mixture was cut and crushed with a mixer and a homogenizer, and the fiber was removed through 32 mesh. At this time, 872 g of a paste was obtained, and the solid content recovery was 56.8%. As a result of measurement of hesperidin and narirutin as flavonoids contained in the peel after seminole squeezing, 5,727 mg / 100 g of hesperidin and 557 mg / 100 mg of narirutin were contained in the solid content. In the paste after removing the fibrous material through 32 mesh, 5,912 mg / 100 g of hesperidin and 581 mg / 100 g of narirutin were contained in the solid content, and there was no large change in the components before and after grinding and filtration. .

  As an enzymatic decomposition step, 0.1% by weight of the paste obtained in the above step was added to a β-glycosidase preparation (manufactured by Amano Enzyme Co., Ltd .: aromase), and the mixture was added at 50 ° C. for 1 hour (Comparative Example 3). 2 hours (Comparative Example 4), 4 hours (Comparative Example 5), 8 hours (Example 1), 16 hours (Example 2), 20 hours (Example 3), and 1 hour at 40 ° C. (Comparative Example) 6) After decomposition, the enzyme was inactivated by heating. Table 3 below shows the contents of hesperetin (aglycone) and hesperidin in the paste and the aglycone abundance ratio (hesperetin / (hesperidin + hesperetin) (mmol%)), and Table 4 shows the contents of naringenin (aglycone) and narilthine and aglycone. The abundance ratio (naringenin / (narirutin + naringenin) (mmol%)) is shown.

Example 4
Ingredients used: Shiranui (Shiranuhi)
Enzyme amount: 0.1%
Processing temperature: 50 ° C
Processing time: 20 hours

In the pasting process, 500 g of residue (mainly composed of pericarp, including a carbohydrate membrane and a small amount of juice, hereinafter referred to simply as "perishable pericarp of Shiranui juice") after squeezing the juice from the fruit of Shiranui. 1 L of water was added, and the mixture was cut and ground with a mixer and a homogenizer, and the fiber was removed through 32 mesh. At this time, 851 g of a paste was obtained, and the solid content recovery was 44.0%. As a result of measuring hesperidin and narirutin as flavonoids contained in the pericarp after juice extraction in Shiranui, 4,165 mg / 100 g of hesperidin and 834 mg / 100 mg of narirutin were contained in the solid content. Further, in the paste after removing the fibrous material through 32 mesh, hesperidin (4,084 mg / 100 g) and nariltin (937 mg / 100 g) were contained in the solid content, and there was no significant change in the components.

  As an enzymatic decomposition step, a 0.1% by weight β-glycosidase preparation (manufactured by Amano Enzyme Co., trade name: Aromase) was added to the paste obtained in the above step, and the mixture was decomposed at 50 ° C. for 20 hours (Example 4). After that, the enzyme was inactivated by heating to prepare a paste. Table 5 below shows the contents of hesperetin (aglycone) and hesperidin and the aglycone abundance ratio (hesperetin / (hesperidin + hesperetin) (mmol%)) in the paste, and Table 6 shows the contents of naringenin (aglycone) and narilthine and the presence of aglycone in the paste. The ratio (naringenin / (narirutin + naringenin) (mmol%)) is shown.

Examples 5 and 6 and Comparative Examples 7 and 8
Ingredients used: Lemon Enzyme amount: 0.1%
Processing temperature: 50 ° C, 40 ° C
Processing time: 1, 8, 20 hours

As a paste-forming step, 500 g of residue (mainly composed of pericarp, including carnivorous membrane and slight juice, etc., hereinafter simply referred to as "lemon juice pericarp") after juice is squeezed from lemon fruit 1 L of water was added, and the mixture was cut and ground with a mixer and a homogenizer, and the fiber was removed through 32 mesh. At this time, 847 g of a paste was obtained, and the solid content recovery was 55.1%. As a result of measuring hesperidin as a flavonoid contained in the pericarp after lemon juice, 2,688 mg / 100 g was contained in the solid content. In the paste after removing the fibrous material through 32 mesh, 2,762 mg / 100 g was contained in the solid content, and there was no large change in the components. The lemon peel hardly contained narirutin, and was not detected in this measurement. As the lemon flavonoids, eriocitrin and the like are known in addition to hesperidin, but the quantification was not performed this time.

  As an enzymatic decomposition step, a β-glycosidase preparation (manufactured by Amano Enzyme Co., trade name: Aromase) having a weight ratio of 0.1% to the paste obtained in the above step was added, and the mixture was treated at 50 ° C. for 8 hours (Example 5). After decomposing for 20 hours (Example 6) and at 40 ° C. for 1 hour (Comparative Example 7) and 20 hours (Comparative Example 8), the enzyme was inactivated by heating. Table 7 below shows the contents of hesperetin (aglycone) and hesperidin in the paste, and the aglycone abundance ratio (hesperetin / (hesperidin + hesperetin) (mmol%)).

[Intestinal absorption test using Caco-2 cells]
The human colon cancer-derived cell Caco-2 forms a monolayer membrane similar to the epithelium of the small intestine when cultured on a porous membrane filter, and selectively permeates (absorbs) the compound. Used for permeability screening. The intestinal absorption model using Caco-2 cells was provided with the paste of Example 3 and the paste not subjected to enzymatic degradation, and the permeability was evaluated. FIG. 2 shows a schematic diagram of an intestinal absorption test using the Caco-2 cells. Each paste was adjusted to a solid content of 5%, diluted with an equal amount of DMSO (dimethyl sulfoxide), added to HBSS (Hanks' Balanced Salt Solutions) 500 μL in 1/100 amount, and added to the Apical (unabsorbed) side. Was. After permeation for 1 hour, the concentrations of hesperidin and hesperetin on the Apical (unabsorbed) side and the Basolateral (absorbed) side were measured.

  As a result, in the paste of Example 3, the concentration of hesperetin on the Apical (unabsorbed) side after permeation for 1 hour was 1,410 ng / 100 ml, and that on the Basolateral (absorbed) side was 480 ng / 100 ml, indicating that hesperetin absorption was confirmed. On the other hand, in the paste not subjected to enzymatic decomposition, the concentration of hesperidin on the Apical (unabsorbed) side was 1,765 ng / 100 ml, and neither hesperidin nor hesperetin was detected on the Basolateral (absorption) side, and hesperetin was not absorbed. That was confirmed. It is known that hesperetin, which is an aglycone, is higher in absorbability into the body than hesperidin. That was confirmed.

  The citrus peel milling paste of the present invention has a flavor unique to citrus fruits, and has a high flavonoid absorbency and a high function, so that it can be suitably used as an additive to various foods and beverages.

Claims (2)

A method for producing a ground paste of citrus peel,
The grinding paste includes hesperetin and naringenin as flavonoid aglycones from peel the citrus state, and are present ratio is more than 90 mmol% of the aglycone represented by the following formula in the該磨grinding paste,
The production method is a process of adding water to the pericarp, which is a residue after squeezing juice from citrus fruits, grinding the paste into a paste, and
Enzymatically decomposing the flavonoid glycosides contained in the ground material of the pericarp to produce the aglycone,
The enzymatic decomposition step is a step of adding 0.05% to 0.3% by weight of β-glycosidase to the paste and performing an enzyme treatment at 45 ° C to 60 ° C for 8 hours to 20 hours. A method for producing a citrus peel ground paste.

Aglycone abundance ratio (mmol%) = (mol number of the aglycone / total mole number of the aglycone and the glycoside of the aglycone) × 100 The method for producing a citrus peel grinding paste according to claim 1, wherein the grinding paste contains two or more types of the aglycones, and the aglycone content ratio of each is 90 mmol% or more.

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