JP6579543B2 - Method for producing citrus extract - Google Patents

Description

  The present invention relates to a method for producing an extract using citrus fruits.

  Citrus fruits have a refreshing aroma, sourness and sweetness, and are widely used not only for raw food but also for processed food materials such as juices, marmalades, and confectionery materials, and seasonings. Citrus fruits contain many functional components such as citric acid, vitamin C, flavonoids, carotenoids, terpenoids and limonoids, and some are used as Kampo ingredients in Oriental medicine including Japan. Many.

  On the other hand, furanocoumarins contained in citrus fruits can cause phototoxic contact dermatitis that causes symptoms such as erythema, pigmentation, and erosion by adhering to the skin, or by taking orally. There is a problem in that it affects the metabolism of the drug and enhances the action or side effect of the drug.

  Various studies have been conducted focusing on various physiological activities brought about by functional components contained in citrus fruits. For example, it is an antioxidant composition (Patent Document 1) characterized by containing water or a hydrous alcoholic extract of citrus fruit peel as an active ingredient, and a food or drink containing eriodictiool and / or diosmethine. An anti-obesity agent containing a hydrophilic component derived from citrus fruits as an active ingredient, which is characterized by having an action of suppressing oxidative denaturation of low-density lipoprotein in blood, The active ingredient contains polyphenol (Patent Document 3), Eriodictiool, Hesperetin, Naringenin, Diosmethine, Eriodictinol glycoside, Hesperetin glycoside, Naringenin glycoside and Xanthine containing as an active ingredient at least one polyphenol selected from diosmethine glycosides Emissions oxidase inhibitors (Patent Document 4) are disclosed.

  In studies aimed at reducing furanocoumarins, for example, lemon oil is distilled under reduced pressure at a temperature and pressure of 120 ° C./10 mmHg or less to obtain a distillate oil. Light obtained by adding an organic solvent to insolubilize and remove furocoumarins, and further adsorbing and removing them with an inorganic adsorbent, and then removing the solvent to produce the oil together with the distillate oil. Non-toxic lemon oil production method (Patent Document 5), natural oil containing psoralens, supercritical carbon dioxide extraction column packed with porous polymer resin using subcritical or supercritical carbon dioxide as fluid A method for producing a natural essential oil containing no psoralens (Patent Document 6) is disclosed, wherein a psoralen in the natural essential oil is fractionated using a chromatographic apparatus.

  Thus, for citrus fruits, there is still a demand for a safe functional material containing useful functional ingredients that it has.

JP-A-8-259945 JP 2004-267155 A JP 2006-321772 A JP 2010-59104 A JP-A-56-70096 Japanese Patent Laid-Open No. 10-316991

  The subject of this invention is providing the manufacturing method of the citrus extract which increased flavanone which is 1 type of a functional component from the citrus fruit as a raw material. Moreover, the subject of this invention is providing the manufacturing method of the citrus extract which reduced the furanocoumarin which has phototoxicity from the citrus fruit as a raw material. Furthermore, the subject of this invention is providing the manufacturing method of the citrus extract which increased the flavanone which is 1 type of a functional component, and reduced the furanocoumarin which has phototoxicity.

  As a result of earnest research, the present inventors, using citrus fruit as a raw material, comprising a step of enzymatic treatment of the raw material, a step of adding fats and oils, and a step of separating and removing the fats and oils, The present inventors have found that the above problems can be solved and completed the present invention.

  That is, the present invention increases flavanone, which is a kind of functional component, by using citrus fruit as a raw material and subjecting the raw material to an enzyme treatment using an enzyme having pectinase activity and an enzyme having β-glucosidase activity. A method for producing a citrus extract is provided. Further, the present invention provides a citrus extract with reduced photo-toxic furanocoumarin by using citrus fruit as a raw material, subjecting the raw material to an enzyme treatment using an enzyme having pectinase activity, and adding and removing oils and fats. The manufacturing method of this is provided. Furthermore, the present invention uses a citrus fruit as a raw material, the raw material is treated with an enzyme having a pectinase activity and an enzyme having a β-glucosidase activity, and after adding and removing oils and fats, functional components are obtained. The present invention provides a method for producing a citrus extract containing a flavanone which is a kind of the above and having reduced photo-toxic furanocoumarin.

The present invention includes the following aspects.
Item (1)
A method for producing a citrus extract, comprising: using a citrus fruit as a raw material, an enzyme treatment using an enzyme having a pectinase activity; and an enzyme treatment using an enzyme having a β-glucosidase activity. A method for producing a citrus extract.
Item (2)
A method for producing a citrus extract, comprising using citrus fruits as a raw material, an enzyme treatment using an enzyme having pectinase activity, an enzyme treatment using an enzyme having β-glucosidase activity, and adding fat A method for producing a citrus extract, comprising: a step; and a step of separating and removing the fats and oils.
Item (3)
A method for producing a citrus extract, comprising using a citrus fruit as a raw material, an enzyme treatment using an enzyme having pectinase activity, a step of adding fats and oils, and a step of separating and removing the fats and oils A method for producing a citrus extract.
Item (4)
The manufacturing method of claim | item (1) or claim | item (2) whose flavanone which a citrus extract contains is a free thing.
Item (5)
Item (1) to Item (4), wherein the citrus is at least one member belonging to the genus Citrus or Fortunella.
Item (6)
The production method according to any one of Items (1) to (5), wherein the raw material is a pulverized product or an extract.
Item (7)
A citrus extract obtained by the production method according to any one of Items (1) to (6).
Item (8)
A food, beverage, quasi drug or feed containing the citrus extract according to item (7).

ADVANTAGE OF THE INVENTION According to this invention, the citrus extract which increased flavanone which is 1 type of a functional component can be provided. Furthermore, according to the present invention, it is possible to provide a citrus extract that increases flavanone, which is a kind of functional component, and reduces phototoxic toxicity such as bergamotine. Moreover, according to this invention, the citrus extract which reduced the phototoxicity furanocoumarins, such as bergamotine, can be provided.
By using the citrus extract according to the present invention, foods, beverages, quasi drugs or feeds utilizing the functionality of flavanone can be provided.

  In the present invention, citrus refers to a plant belonging to any of the genus Citrus, Fortunella, or Poncirus among the plants belonging to the family Rutaceae, in particular, Aurantioidee. Point to. Citrus has, for example, hassaku (Citrus hassaku), lemon (Citrus limon), grapefruit (Citrus x paradisi), yuzu (Citrus junos), bergamot (Citrus x bergamia), bilolo (Citrus us, Citrus unshiu, lime (Citrus aurantifolia), sudachi (Citrus sphaerocarpa), mandarin orange (Citrus reticulata), dai ss (ur), dais itrus iyo), bellows (Citrus natubadaiai), hyuga natsu (Citrus tamurana), buntan (Citrus maxima), tangol (Citrus reticulata) (Fortunella crassifolia), Japanese kumquat (Fortunella margarita), Nagakina kumquat (Fortunella polandara), Fukushu kumquat (Fortunella obobata), Fortunella pincinch (Fortunella pincina) irus trifoliata), and the like. Among these, plants belonging to the genus Citrus or the genus Fortunella, whose fruits are often used for food, are preferred.

  As a raw material used in the present invention, citrus fruits are used. The citrus fruit used as a raw material can be used in a raw state or a dried one. Moreover, the citrus fruit of a raw material may be used individually by 1 type, and may use multiple types together.

  In the present invention, the raw material citrus fruit may be a pulverized product or an extract.

  The pulverized product of citrus fruits may be a pulverized product obtained by pulverizing raw citrus fruits alone or by adding a solvent such as water. The method for pulverizing the raw citrus fruit is not particularly limited, and methods generally used for processing foods can be used alone or in combination. Examples of the equipment used for the pulverization include various cutting machines, pulverizers, and press machines that process using cutting, pulverizing, pressing, friction, air pressure, water pressure, and the like. Furthermore, the pulverized product of citrus fruits may be diluted with water or the like, and an additive such as a pH adjuster may be appropriately blended.

  The extract of a citrus fruit should just be the extract which extracted the citrus fruit of a raw material with water, alcohol, or a water-alcohol mixed solution. The method for extracting the citrus fruit as a raw material is not particularly limited, and known means can be extracted alone or in combination. Examples of extraction methods include room temperature extraction, heat extraction, pressure extraction, stirring extraction, and ultrasonic extraction. The raw material citrus fruit may be extracted as it is, or a chopped or crushed product may be used. The extract of a citrus fruit can use the liquid part obtained after extraction or by solid-liquid separation. Among these, a liquid part obtained by solid-liquid separation after extraction is preferable. Moreover, the concentrate can be used for the extract of a citrus fruit. Furthermore, the citrus fruit extract may be diluted with water or the like, and an additive such as a pH adjuster may be appropriately blended.

  In the present invention, the raw material citrus fruit is subjected to an enzyme treatment using an enzyme having pectinase activity. In the present invention, the enzyme having β-glucosidase activity is brought about when the raw citrus fruit is subjected to enzyme treatment using an enzyme having pectinase activity, and the enzyme treatment is performed using an enzyme having β-glucosidase activity. The effect can be further improved. Moreover, when adding fats and oils, the effect which fats and oils bring can be improved further. The enzyme having pectinase activity used in the present invention may be any enzyme as long as it has pectinase activity that can be used in foods, and may contain the enzyme. The enzyme can also be used in the form of an enzyme preparation. Examples of the enzyme having pectinase activity include, for example, Sumiteam (registered trademark) AP2 (manufactured by Shin Nippon Chemical Industry Co., Ltd.), Sumiteam SPC (same), Sumiteam MC (same), Sumiteam PTE (same), cellulosin (a pectinase preparation). Registered trademark) PE60 (manufactured by HBI Corporation), pectinase G “Amano” (manufactured by Amano Enzyme), pectinase PL “Amano” (same), and the like.

  In the present invention, the temperature at which the raw citrus fruit is enzymatically treated with an enzyme having pectinase activity is usually 20 to 80 ° C, preferably 30 to 75 ° C, more preferably 40 to 70 ° C. Moreover, in this invention, the time which enzyme-processes the raw material citrus fruit using the enzyme which has pectinase activity is 10 minutes-12 hours normally, Preferably it is 30 minutes-6 hours. In the present invention, the amount of the enzyme having pectinase activity can be appropriately changed depending on the treatment temperature and treatment time. For example, the enzyme preparation is usually 0.01 to 5% by weight, preferably 0.05. -3% by weight, more preferably 0.1-2% by weight.

  In the present invention, before the enzyme treatment with an enzyme having pectinase activity, the pH of the raw citrus fruit is preferably adjusted to around the optimum pH of the enzyme having pectinase activity. The pH to be adjusted is usually pH 2-7, preferably pH 2.5-6. In addition, when the said pH adjustment is performed, you may neutralize, after carrying out an enzyme treatment using the enzyme which has pectinase activity. For pH adjustment and neutralization treatment, those generally used in foods and the like as pH adjusters can be used. The pH adjuster is not particularly limited as long as it is designated as at least a food additive. Examples of the pH adjuster include acids, alkalis, and salts thereof, and examples thereof include hydrochloric acid, citric acid, acetic acid, sodium hydroxide, sodium carbonate, and sodium bicarbonate.

  In the present invention, citrus fruit is used as a raw material, and the raw material is subjected to an enzyme treatment using an enzyme having β-glucosidase activity. The enzyme having β-glucosidase activity used in the present invention may be any enzyme that has at least β-glucosidase activity that can be used in food, and may contain the enzyme. It can also be used in the form of an enzyme preparation. Examples of the enzyme having β-glucosidase activity include aromase (registered trademark) (manufactured by Amano Enzyme Co., Ltd.), Sumiteam (registered trademark) BGA (manufactured by Shin Nippon Chemical Industry Co., Ltd.), and rapidase (registered trademark), which are β-glucosidase preparations. Trademark) AR2000 (manufactured by DSM Japan Ltd.) and the like.

  In this invention, the temperature which carries out an enzyme process using the enzyme which has (beta) -glucosidase activity is 20-70 degreeC normally, Preferably it is 30-70 degreeC, More preferably, it is 40-65 degreeC. In the present invention, the enzyme treatment time using an enzyme having β-glucosidase activity is usually 30 minutes to 30 hours, preferably 1 to 24 hours, more preferably 2 to 20 hours. Moreover, in this invention, although the addition amount of the enzyme which has (beta) -glucosidase activity can be suitably changed with process temperature and process time, for example with respect to the fruit of the citrus fruit of a raw material as enzyme preparations, it is usually 0. 01 to 5% by weight, preferably 0.05 to 3% by weight, more preferably 0.1 to 2% by weight.

  In the present invention, before the enzyme treatment with an enzyme having β-glucosidase activity, it is preferable to adjust the pH of the raw citrus fruit to be close to the optimum pH of the enzyme having β-glucosidase activity. The pH to be adjusted is usually pH 2 to 8, preferably pH 2.5 to 6. When the pH is adjusted, neutralization may be performed after the enzyme treatment. For pH adjustment and neutralization treatment, those generally used in foods and the like as pH adjusters can be used. The pH adjuster is not particularly limited as long as it is designated as at least a food additive. Examples of the pH adjuster include hydrochloric acid, citric acid, acetic acid, sodium hydroxide, sodium carbonate, sodium hydrogen carbonate and the like.

In the present invention, the content of flavanone that is one of the functional components contained in the resulting citrus extract is at least greater than the content of flavanone contained in the raw material at the time of use in the production method of the present invention. It only has to be. In the present invention, the flavanone content contained in the obtained citrus extract is preferably 0.1% by weight or more, more preferably 0.2% by weight or more per solid. The production method of the present invention can significantly increase the flavanone content. In particular, as a flavanone peculiar to citrus fruits, eriodict thiol, naringenin or hesperetin can be mentioned, and in the present invention, the content of at least one of these can be increased.
In addition, the flavanone which a citrus extract contains in this invention means the thing of what is called a free state which exists in the state of an aglycon.

  In the present invention, the enzyme deactivation treatment is performed after the enzyme treatment. The enzyme deactivation treatment may be performed so that the enzyme activity does not remain in the finally obtained citrus extract, and the enzyme deactivation treatment conditions are as long as the enzyme used in the enzyme treatment is deactivated. There is no particular limitation.

In the present invention, the raw material citrus fruit may be subjected to a stirring treatment by adding fats and oils. In order to improve the miscibility with fats and oils, the citrus fruit as a raw material is preferably treated with an enzyme using an enzyme having pectinase activity.
In this invention, after adding fats and oils and carrying out a stirring process, the said citrus extract which reduced content of furanocoumarin which has phototoxicity, such as bergamotine, can be manufactured by isolate | separating and removing this fats and oils. In the present invention, an enzyme treatment using an enzyme having β-glucosidase activity and an oil and fat are added and stirred, and then the oil and fat is separated and removed, so that the content of flavanone, which is a kind of functional component, can be efficiently obtained. In addition to increasing the content of citrus fruits, the content of the photo-toxic furanocoumarin such as bergamotine can be effectively reduced. In particular, the furanocoumarins peculiar to citrus fruits include bergapten, bergamotin, or oxypoisedanine. In the present invention, the content of at least one of them can be reduced. In the present invention, the content of furanocoumarin contained in the obtained citrus extract may be reduced as compared to before adding and separating oil and fat, preferably 10 ppm or less per solid, more preferably not. It is detection.
In the case where an oil and fat is added and the stirring treatment is performed, when the enzyme treatment using an enzyme having β-glucosidase activity is performed, it is preferably performed in parallel with the stirring treatment or after the stirring treatment.

  The fats and oils used in the present invention may be any fats and oils that can generally be used for foods and the like, and may contain the fats and oils. Examples of the fats and oils used in the present invention include rice bran oil, rapeseed oil, soybean oil, corn oil, sunflower oil, safflower oil, cottonseed oil, olive oil, sesame oil, peanut oil, grape seed oil, persimmon oil, perilla oil, linseed oil, walnut Oil, mustard oil, pumpkin seed oil, watermelon seed oil, coconut oil, almond oil, hazelnut oil, macadamia nut oil, cashew nut oil, pistachio oil, wheat germ oil, tea seed oil, avocado oil, papaya oil, palm oil, palm kernel Vegetable oils such as oil, coconut oil, cacao butter; animal oils such as lard, head, chicken oil, fish oil, horse oil, whale oil, seal oil, milk fat; and hydrogenated oils, fractionated oils, etc. .

  In the present invention, the method of adding oil and fat and stirring is not particularly limited, and a known means generally used for stirring can be used. As a method of adding fats and oils and stirring, for example, a method of stirring a stirring object with a mechanical or magnetic stirrer using a stirring blade or a stirring bar, a stirring process by blowing a gas such as air or nitrogen into the stirring object And a method of stirring the stirring target by shaking, rotating, or the like a container containing the stirring target.

  In the present invention, the temperature at which the oil and fat is added and stirred may be any temperature as long as the oil or fat to be added has fluidity, but is usually 20 to 100 ° C, preferably 30 to 90 ° C, more preferably 35 to 80. ° C. Moreover, in this invention, the time which adds fats and oils and stir-processes is at least 5 minutes or more, and is normally 10 minutes-30 hours, Preferably it is 20 minutes-24 hours, More preferably, it is 30 minutes-20 hours. Further, in the present invention, the amount of oil and fat to be agitated can be appropriately changed depending on the treatment temperature and the treatment time, but is usually 0 by weight with respect to the solid matter in the treatment liquid to which the oil and fat is added. 2 to 20 times, preferably 0.5 to 15 times, more preferably 1 to 10 times.

  In the present invention, when oil and fat are added and stirring is performed, the used oil and fat is separated and removed. The method for separating and removing the oil and fat is not particularly limited, and can be performed by a known method such as centrifugation, decantation, use of an oil adsorbent or an oil flocculant.

  In the present invention, the raw material citrus fruit may be subjected to an enzyme treatment using an enzyme having cellulase activity or an enzyme having hemicellulase activity. The enzyme having cellulase activity or the enzyme having hemicellulase activity used in the present invention may be any enzyme as long as it can be used in foods, and may contain the enzyme. The enzyme can also be used in the form of an enzyme preparation. Examples of the enzyme having cellulase activity include cellulase preparations such as Sumiteam (registered trademark) AC (manufactured by Shinnippon Chemical Co., Ltd.), Sumiteam C (same), cellulosin (registered trademark) AC40 (manufactured by HBI Corporation), cellulosin. Examples of the enzyme having hemicellulase activity include Sumiteam (registered trademark) ACH (manufactured by Shin Nippon Chemical Industry Co., Ltd.), Sumiteam X (same), and Cellulosin (registered trademark) HC (HTV). Co., Ltd.), Cellulosin TP25 (same as above)

  In the present invention, the temperature at which the raw citrus fruit is enzymatically treated with an enzyme having cellulase activity or an enzyme having hemicellulase activity is usually 20 to 80 ° C, preferably 30 to 75 ° C, more preferably 40 to 70. ° C. Moreover, in this invention, the time which enzyme-treats the raw material citrus fruit using the enzyme which has cellulase activity, or the enzyme which has hemicellulase activity is 10 minutes-12 hours normally, Preferably it is 30 minutes-6 hours. In the present invention, the addition amount of the enzyme having cellulase activity or the enzyme having hemicellulase activity can be appropriately changed depending on the treatment temperature and treatment time. For example, the enzyme preparation is usually 0.01 to 5 wt. %, Preferably 0.05 to 3% by weight, more preferably 0.1 to 2% by weight.

  In the present invention, before enzyme treatment with an enzyme having cellulase activity or an enzyme having hemicellulase activity, the pH of the raw citrus fruit is adjusted to the optimum of the enzyme having cellulase activity or the enzyme having hemicellulase activity. It is preferable to adjust to around pH. The pH to be adjusted is usually pH 2-7, preferably pH 2.5-6. When the pH is adjusted, neutralization may be performed after enzyme treatment using an enzyme having cellulase activity or an enzyme having hemicellulase activity. For pH adjustment and neutralization treatment, those generally used in foods and the like as pH adjusters can be used. The pH adjuster is not particularly limited as long as it is designated as at least a food additive. Examples of the pH adjuster include acids, alkalis, and salts thereof, and examples thereof include hydrochloric acid, citric acid, acetic acid, sodium hydroxide, sodium carbonate, and sodium bicarbonate.

  Since the citrus extract obtained by the present invention has a good flavor and excellent palatability, it can be used as it is, but it can also be used as a liquid part obtained by solid-liquid separation. The method for solid-liquid separation is not particularly limited, and can be performed by a known method such as filtration or centrifugation. Moreover, the citrus extract obtained by the present invention may be used as a concentrate by treating the liquid part as it is or separated into solid and liquid with a concentrator or the like by a conventional method, or may be used after drying. The drying method is not particularly limited, and the drying can be performed using a known means. As a drying method, for example, a known means such as a spray dryer, a drum dryer, a freeze dryer, or an air dryer can be used. Further, an excipient such as dextrin may be added and dried. Further, the product obtained by drying may be pulverized and used as a powder or the like, and if necessary, it can be made into a granule using a granulator or the like.

  The citrus extract obtained by the present invention can be used as it is or diluted with water or the like. Furthermore, the citrus extract obtained by the present invention is suitably used for various processed foods, for example, instant foods, dairy products, confectionery, seasonings, tea beverages, vegetable beverages, soy beverages, soy milk beverages and the like. It can also be added and blended. Moreover, it can also use together with what is used as a raw material or additive of normal food or a drink as needed.

  The citrus extract obtained by the present invention can be used for foods such as foods for specified health use, functional foods, dietary supplements, quasi drugs, feeds, and the like. The form can be ampoules, capsules, pills, tablets, powders, granules, solids, liquids, gels, aerosols, etc., and can be blended in various products. In preparing these products, excipients, binders, lubricants and the like can be appropriately blended.

  EXAMPLES Hereinafter, although an Example is shown and this invention is demonstrated concretely, this invention is not limited by the following examples. In this example, the blending ratio, content ratio, and concentration of each raw material and material are all based on parts by weight unless otherwise specified.

[Preparation 1]
1000 g of washed wasak fruit (hole) was pulverized, 500 g of water was added and mixed, 1.5 g of Sumiteam AP2 as a pectinase preparation was added, and enzyme treatment was performed at 60 ° C. for 2 hours. Next, after performing enzyme deactivation treatment at 90 ° C. for 10 minutes, 750 g of Hassaku extract (solid content: 9%) was obtained by performing solid-liquid separation by filtration using a filter cloth (nonwoven fabric) and collecting the liquid part. 8%, pH 3.2) (Preparation 1) was obtained.

[Example 1]
By adding 0.5 g of aromase, which is a β-glucosidase preparation, to 100 g of Hassaku extract obtained in Preparation 1, and performing enzyme treatment at 60 ° C for 5 hours, followed by enzyme deactivation treatment at 90 ° C for 10 minutes 90 g (solid content 10.2%) (Example 1) of the present invention treated with β-glucosidase was obtained.

[Example 2]
20 g of rice bran oil (rice salad oil: manufactured by Kato Oil Co., Ltd.) was added to 100 g of the hassaku extract obtained in Preparation 1, and the mixture was stirred at room temperature (20 ° C. to 25 ° C.) for 10 minutes. After completion of stirring, the mixture was allowed to stand for 1 hour for separation, and the oil layer (upper layer) was removed to recover the aqueous layer (lower layer). 0.5 g of aromase, which is a β-glucosidase preparation, is added to the recovered aqueous layer, and after enzyme treatment at 60 ° C. for 5 hours, enzyme inactivation treatment is performed at 90 ° C. for 10 minutes. -90 g of citrus extract of the present invention treated with glucosidase (solid content 10.7%) (Example 2) was obtained.

[Example 3]
0.5 g of aromase, which is a β-glucosidase preparation, was added to 100 g of Hassaku extract obtained in Preparation 1, and the enzyme treatment was performed at 60 ° C. for 5 hours, followed by enzyme deactivation treatment at 90 ° C. for 10 minutes. Subsequently, 20 g of rice bran oil (rice salad oil: manufactured by Kato Oil Co., Ltd.) was added and stirred at room temperature (20 ° C. to 25 ° C.) for 10 minutes. After completion of stirring, the mixture was allowed to stand for 1 hour for separation, and the oil layer (upper layer) was removed and the aqueous layer (lower layer) was recovered. Thus, 90 g of the citrus extract of the present invention subjected to β-glucosidase treatment and oil and fat stirring treatment (solid content 11) 0.2%) (Example 3) was obtained.

[Example 4]
20 g of rice bran oil (rice salad oil: manufactured by Kato Oil Co., Ltd.) was added to 100 g of the hassaku extract obtained in Preparation 1, and the mixture was stirred at room temperature (20 ° C. to 25 ° C.) for 10 minutes. After completion of stirring, the mixture was allowed to stand for 1 hour for separation, and the oil layer (upper layer) was removed, and the aqueous layer (lower layer) was recovered. Example 4) was obtained.

[Contrast test 1]
For the citrus extracts of the present invention obtained in Example 1, Example 2, Example 3 and Example 4 and the Hassaku extract obtained in Preparation 1, the content of flavanone (eriodictyol, naringenin and hesperetin) The content of furanocoumarin (bergapten, bergamotin and oxypoisedanine) was measured by high performance liquid chromatography (hereinafter referred to as “HPLC”) under the following measurement conditions. The results are shown in Table 1.

<HPLC measurement conditions: flavanone (eriodictyol, naringenin and hesperetin>
Detector: UV detector (ultraviolet wavelength 260 nm)
Column: Inert Sustain C18 (inner diameter 4.6 mm, length 250 mm)
Mobile phase A: 15% by volume acetonitrile aqueous solution (containing 0.1% by volume phosphoric acid)
Mobile phase B: 40% by volume acetonitrile aqueous solution (containing 0.1% by volume phosphoric acid)
Gradient: Gradient from mobile phase A to mobile phase B (45 minutes)
Flow rate: 1.0 ml / min Column temperature: 40 ° C
Sample: Eriodictyol (manufactured by Wako Pure Chemical Industries, Ltd.), Naringenin (manufactured by Wako Pure Chemical Industries, Ltd.) and Hesperetin (manufactured by Tokyo Chemical Industry Co., Ltd.) are each dissolved in 80% acetonitrile aqueous solution and then diluted appropriately. A calibration curve was created.
Specimen: Each sample diluted appropriately with 80% acetonitrile aqueous solution.

<HPLC measurement conditions: furanocoumarin (bergapten, bergamotin and oxypoisedanine>
Detector: UV detector (ultraviolet wavelength 310 nm)
Column: Inert Sustain Phenyl (inner diameter 4.6 mm, length 250 mm)
Mobile phase A: 40% by volume acetonitrile aqueous solution (containing 0.1% by volume phosphoric acid)
Mobile phase B: acetonitrile gradient: gradient from mobile phase A to mobile phase B (35 minutes)
Flow rate: 1.0 ml / min Column temperature: 40 ° C
Sample: Bergapten (manufactured by Tokyo Chemical Industry Co., Ltd.), bergamotin (manufactured by Wako Pure Chemical Industries, Ltd.) and oxypoisedanine (manufactured by Wako Pure Chemical Industries, Ltd.) were each dissolved in acetonitrile, and then diluted as appropriate. Created a line.
Sample: Each sample diluted appropriately with acetonitrile.

  As shown in Table 1, none of flavanone was detected in the Hassaku extract of Preparation 1, but obtained in Examples 1, 2 and 3 which were enzymatically treated with an enzyme having β-glucosidase activity. In the obtained citrus extract of the present invention, flavanone was significantly detected. In addition, with respect to furanocoumarin, a large amount of furanocoumarin was detected in the extract of preparation 1 but the citrus extract of the present invention obtained in Example 1 contained furanocoumarin as compared with the extract of preparation 1. Furthermore, in the citrus extracts of Examples 2, 3 and 4 of the present invention, it was reduced to a level where no furanocoumarin was detected.

[Preparation 2]
3000 g of lemon fruit (hole) washed with water was pulverized, 1500 g of water was added and mixed, 4.4 g of Sumiteam AP2 as a pectinase preparation was added, and enzyme treatment was performed at 60 ° C. for 2 hours. Subsequently, after enzyme deactivation treatment at 90 ° C. for 10 minutes, the solid liquid is obtained by filtering using a standard sieve conforming to JIS Z8801-1: a sieve having a nominal aperture of 150 μm (hereinafter referred to as “100 mesh”). Separation was performed and the liquid part was recovered to obtain 2050 g of a lemon extract (solid content 8.1%, pH 2.7) (Preparation 2).

[Example 5]
By adding 0.08 g of aromase which is a β-glucosidase preparation to 80 g of the lemon extract obtained in Preparation 2, and performing enzyme treatment at 60 ° C. for 2 hours, followed by enzyme deactivation treatment at 90 ° C. for 10 minutes. Then, 70 g (solid content 7.8%) of the citrus extract of the present invention treated with β-glucosidase (Example 5) was obtained.

[Example 6]
24 g of palm oil (Palm Ace (registered trademark) N: manufactured by Fuji Oil Co., Ltd.) was added to 80 g of the lemon extract obtained in Preparation 2, and the mixture was stirred at room temperature (20 ° C. to 25 ° C.) for 10 minutes. After completion of the stirring, centrifugation (2000 × G, 5 minutes) was performed to remove the oil layer (upper layer) and recover the aqueous layer (lower layer). 0.08 g of aromase, which is a β-glucosidase preparation, was added to the recovered aqueous layer, and after enzyme treatment at 60 ° C. for 2 hours, enzyme inactivation treatment was carried out at 90 ° C. for 10 minutes, so that the oil and fat stirring treatment and β -The citrus extract 70g (solid content 7.9%) (Example 6) of this invention which processed glucosidase was obtained.

[Example 7]
0.08 g of aromase, which is a β-glucosidase preparation, was added to 80 g of the lemon extract obtained in Preparation 2, and the enzyme treatment was performed at 60 ° C. for 2 hours, followed by enzyme deactivation treatment at 90 ° C. for 10 minutes. Subsequently, 24 g of palm oil (Palm Ace N: manufactured by Fuji Oil Co., Ltd.) was added and stirred at room temperature (20 ° C. to 25 ° C.) for 10 minutes. Centrifugation treatment (2000 × G, 5 minutes) after completion of stirring, removing the oil layer (upper layer) and collecting the aqueous layer (lower layer), the citrus extract of the present invention subjected to β-glucosidase treatment and fat stirring treatment 70 g (solid content 7.3%) (Example 7) was obtained.

[Example 8]
24 g of palm oil (Palm Ace N: manufactured by Fuji Oil Co., Ltd.) was added to 80 g of the lemon extract obtained in Preparation 2, and the mixture was stirred at room temperature (20 ° C. to 25 ° C.) for 10 minutes. Centrifugation treatment (2000 × G, 5 minutes) is performed after the stirring is completed, the oil layer (upper layer) is removed, and the aqueous layer (lower layer) is recovered. 6%) (Example 8) was obtained.

[Contrast test 2]
For the citrus extract of the present invention obtained in Example 5, Example 6, Example 7 and Example 8 and the lemon extract obtained in Preparation 2, the content of flavanone (eriodictyol, naringenin and hesperetin) The content of furanocoumarin (bergapten, bergamotin and oxypoisedanine) was measured in the same manner as in comparative test 1. The results are shown in Table 2.

  As shown in Table 2, for flavanone, none was detected in the lemon extract of Preparation 2, but it was obtained in Example 5, Example 6 and Example 7 that were enzymatically treated with an enzyme having β-glucosidase activity. In the obtained citrus extract of the present invention, flavanone was significantly detected. In addition, with respect to furanocoumarin, furanocoumarin was detected in the lemon extract of Preparation 2, but in the citrus extract of the present invention obtained in Example 5, furanocoumarin was reduced as compared with the lemon extract of Preparation 2. Furthermore, in the citrus extracts of the present invention of Example 6, Example 7 and Example 8, it was reduced to a level where furanocoumarin was not detected.

[Example 9]
While adding 70 g of hardened palm oil (Palm Ace N: manufactured by Fuji Oil Co., Ltd.) to the pulverized product (pH 3.1) obtained by pulverizing 350 g of washed grapefruit fruit (hole), Then, 0.35 g of Sumiteam AP2 as a pectinase preparation and 0.35 g of Sumiteam AC (manufactured by Shin Nippon Chemical Industry Co., Ltd.) as a cellulase preparation were added, respectively, and the enzyme treatment was performed at 60 ° C. for 1 hour. Next, after solid-liquid separation is performed by filtration using a filter cloth (nonwoven fabric) and the liquid part is recovered, centrifugal separation (2000 × G, 5 minutes) is performed, and the oil layer (upper layer) is removed to remove the water layer. (Lower layer) was collected. After adding 0.7 g of aromase, which is a β-glucosidase preparation, to the recovered aqueous layer, and performing enzyme treatment at 60 ° C. for 1 hour, enzyme deactivation treatment is performed at 90 ° C. for 10 minutes. -260 g of citrus extract of the present invention treated with glucosidase (solid content 10.2%) (Example 9) was obtained.

[Example 10]
While adding 70 g of hardened palm oil (Palm Ace N: manufactured by Fuji Oil Co., Ltd.) to the pulverized product (pH 3.1) obtained by pulverizing 350 g of washed grapefruit fruit (hole), , 0.7 g of aromase which is a β-glucosidase preparation, 0.35 g of Sumiteam AP2 which is a pectinase preparation, and 0.35 g of Sumiteam AC (manufactured by Shin Nippon Chemical Industry Co., Ltd.) which is a cellulase preparation, respectively, Then, the enzyme treatment was performed at 90 ° C. for 10 minutes. Next, after solid-liquid separation is performed by filtration using a filter cloth (nonwoven fabric) and the liquid part is recovered, centrifugal separation (2000 × G, 5 minutes) is performed, and the oil layer (upper layer) is removed to remove the water layer. By recovering the (lower layer), 260 g (solid content 10.1%) (Example 10) of the citrus extract of the present invention treated with fats and oils and β-glucosidase was obtained.

[Comparative Example 1]
A pulverized product (pH 3.1) obtained by pulverizing 350 g of grapefruit fruit (hole) washed with water, 0.35 g of Sumiteam AP2 which is a pectinase preparation, and Sumiteam AC which is a cellulase preparation (manufactured by Shin Nippon Chemical Industry Co., Ltd.) 0.35 g of each was added, and enzyme treatment was performed at 60 ° C. for 2 hours. Next, after performing enzyme deactivation treatment at 90 ° C. for 10 minutes, 280 g of grapefruit extract (solid content: 9%) was obtained by performing solid-liquid separation by filtration using a filter cloth (nonwoven fabric) and collecting the liquid part. 8%) (Comparative Example 1) was obtained.

[Contrast test 3]
About the citrus extract of the present invention obtained in Example 9 and Example 10 and the grapefruit extract obtained in Comparative Example 1, the content of flavanone (eriodictyol, naringenin and hesperetin) and the furanocoumarin (bergapten, bergamotin) And oxypoisedanine) were measured in the same manner as in Comparative Test 1. The results are shown in Table 3.

  As shown in Table 3, flavanone was significantly detected in the citrus extracts of the present invention obtained in Example 9 and Example 10 obtained by enzymatic treatment using an enzyme having β-glucosidase activity. Furthermore, only a small amount of flavanone was detected in the grapefruit extract of Comparative Example 1 which was not treated with an enzyme having β-glucosidase activity. Moreover, about furanocoumarin, in the citrus extract of this invention obtained in Example 9 and Example 10, compared with the grapefruit extract of the comparative example 1, furanocoumarin is notably reduced. In the citrus fruit extract of the present invention, furanocoumarin was reduced to a level where it was not detected.

[Preparation 3]
After squeezing the yuzu fruit, 200 g of the residue was pulverized, 100 g of water was added and mixed (pH 3.2), 0.3 g of Sumiteam AP2, a pectinase preparation, was added, and the enzyme treatment was performed at 60 ° C. for 2 hours. Went. Next, after performing enzyme deactivation treatment at 90 ° C. for 10 minutes, 200 g of uzu extract (solid content of 10.0 g) was obtained by solid-liquid separation by filtration using a 100 mesh sieve and collecting the liquid part. %) (Preparation 3).

[Example 11]
By adding 0.2 g of aromase, which is a β-glucosidase preparation, to 40 g of the yuzu extract obtained in Preparation 3, and performing enzyme treatment at 60 ° C. for 5 hours, followed by enzyme deactivation treatment at 90 ° C. for 10 minutes. Thus, 35 g (solid content 10.6%) of the citrus extract of the present invention treated with β-glucosidase (Example 11) was obtained.

[Example 12]
8 g of rice bran oil (rice salad oil: manufactured by Kato Oil Co., Ltd.) was added to 40 g of the yuzu extract obtained in Preparation 3, and the mixture was stirred at room temperature (20 ° C. to 25 ° C.) for 10 minutes. After completion of stirring, the mixture was allowed to stand for 1 hour for separation, and the oil layer (upper layer) was removed to recover the aqueous layer (lower layer). 0.2 g of aromase, which is a β-glucosidase preparation, was added to the recovered aqueous layer, and after enzyme treatment at 60 ° C. for 5 hours, enzyme inactivation treatment was performed at 90 ° C. for 10 minutes. -35 g of citrus extract of the present invention treated with glucosidase (solid content 11.4%) (Example 12) was obtained.

[Example 13]
0.2 g of aromase, which is a β-glucosidase preparation, was added to 40 g of the yuzu extract obtained in Preparation 3, and the enzyme treatment was performed at 60 ° C. for 5 hours, followed by enzyme deactivation treatment at 90 ° C. for 10 minutes. Subsequently, 8 g of rice bran oil (rice salad oil: manufactured by Kato Oil Co., Ltd.) was added and stirred at room temperature (20 ° C.) for 10 minutes. After completion of stirring, the mixture was allowed to stand for 1 hour for separation, and the oil layer (upper layer) was removed and the aqueous layer (lower layer) was recovered. Thus, 35 g of the citrus extract of the present invention subjected to β-glucosidase treatment and oil and fat stirring treatment (solid content 11) .3%) (Example 13) was obtained.

[Example 14]
8 g of rice bran oil (rice salad oil: manufactured by Kato Oil Co., Ltd.) was added to 40 g of the yuzu extract obtained in Preparation 3, and the mixture was stirred at room temperature (20 ° C. to 25 ° C.) for 10 minutes. After completion of stirring, the mixture was allowed to stand for 1 hour for separation, and the oil layer (upper layer) was removed, and the aqueous layer (lower layer) was recovered. Example 14) was obtained.

[Contrast test 4]
For the citrus extract of the present invention obtained in Example 11, Example 12, Example 13 and Example 14 and the yuzu extract obtained in Preparation 3, the content of flavanone (eriodictyol, naringenin and hesperetin) The content of furanocoumarin (bergapten, bergamotin and oxypoisedanine) was measured in the same manner as in comparative test 1. The results are shown in Table 4.

  As shown in Table 4, for flavanone, none was detected in the yuzu extract of Preparation 3, but it was obtained in Example 11, Example 12, and Example 13 that were treated with an enzyme having β-glucosidase activity. In the obtained citrus extract of the present invention, flavanone was significantly detected. In addition, for furanocoumarin, furanocoumarin was detected in the yuzu extract of Preparation 3, but in the citrus extract of the present invention obtained in Examples 12, 13 and 14, the yuzu extract of Preparation 3 and In comparison, the level of furanocoumarin was reduced to a level where it was not detected.

[Example 15]
50 g of palm oil (Palm Ace N: manufactured by Fuji Oil Co., Ltd.) was added to 200 g of the Hassaku extract obtained in Preparation 1, and the mixture was stirred at 50 ° C. for 10 minutes. After completion of the stirring, centrifugation (2000 × G, 5 minutes) was performed to remove the oil layer (upper layer) and recover the aqueous layer (lower layer). 0.4 g of aromase, which is a β-glucosidase preparation, was added to the collected aqueous layer, followed by enzyme treatment at 60 ° C. for 2 hours, followed by enzyme deactivation treatment at 90 ° C. for 10 minutes. Next, further centrifugation (2000 × G, 5 minutes) is performed, the supernatant is removed, the precipitate is recovered, and the recovered precipitate is dried using a freeze dryer, so that the oil and fat stirring process and β- A glucosidase-treated citrus extract powder 0.5 g (solid content 95.5%) (Example 15) was obtained.
About the obtained citrus extract powder of the present invention, the content of flavanones (eriodictyol, naringenin and hesperetin) and the content of furanocoumarins (bergapten, bergamotin and oxypoisedanine) are the same as in Comparative Test 1. And measured. The results are shown in Table 5.

  As shown in Table 5, none of flavanones was detected in the Hassaku extract of Preparation 1, but the citrus extract of the present invention obtained in Example 15 obtained by enzyme treatment using an enzyme having β-glucosidase activity. Significantly flavanone was detected in the powder. In addition, with respect to furanocoumarin, a large amount of furanocoumarin was detected in the extract of preparation 1 but the citrus extract of the present invention obtained in Example 15 contained furanocoumarin as compared with the extract of preparation 1. Reduced to an undetectable level.

Claims (4)

  A method for producing a citrus extract, comprising using citrus fruits as a raw material, an enzyme treatment using an enzyme having pectinase activity, an enzyme treatment using an enzyme having β-glucosidase activity, and adding fat A method for producing a citrus extract, comprising: a step; and a step of separating and removing the fats and oils. Flavanone containing citrus extract is of free process according to claim 1. The manufacturing method of Claim 1 or Claim 2 whose citrus is at least 1 sort (s) which belongs to the citrus genus (Citrus) or the kumquat genus (Fortunella). The process according to the raw material, any one of claims 1 to 3 is a pulverized product or extract.