JP4789453B2 - Anthocyanin absorption promoter - Google Patents

Description

  The present invention relates to an anthocyanin absorption accelerator, an anthocyanin absorption promotion method, and an anthocyanin-containing composition having an anthocyanin absorption promotion effect.

  Anthocyanins exist widely in nature, and are widely used as natural pigments in foods, pharmaceuticals, quasi drugs, cosmetics, and the like. In Europe, blueberry anthocyanins have been mainly used as pharmaceuticals in Europe, and recently, even in Japan, attention has been focused on the functionality of anthocyanins as a method other than anthocyanin pigments. For example, an effective pharmacological property has been found for blueberry anthocyanins in the treatment of diseases of peripheral blood vessels (see Patent Document 1). In addition, the present inventors have also found some effective functions in the anthocyanins of Cassis and have filed patent applications (see Patent Document 2).

  Physiologically active substances, not limited to anthocyanins, are absorbed from the digestive tract after ingestion and circulate in the body via blood to exert their pharmacological properties. That is, in order to effectively use its pharmacological properties in the body, it must be taken into the body from the digestive tract. Therefore, in order to efficiently exhibit pharmacological properties, it is desirable that the absorption rate into the body is high.

  In addition, physiologically active substances such as anthocyanins circulating in the body are partly accumulated in organs and the like, but most are excreted in urine and partly excreted in stool via bile. Therefore, the recovery rate in urine has a certain relationship with the absorption rate in the body.

  However, it has been reported that the recovery rate of anthocyanins from the urine (corresponding to the absorption rate in the body) is very low, and even in the highest cases, the anthocyanins recovered in the urine account for 1% of the oral intake. Less than 0.1% for most anthocyanins. Compared to the urinary recovery rate of about 10% for catechins and the like having a similar structure, the urinary recovery rate of 1/100 or less is a major obstacle to the physiological activity of anthocyanins. It has become. As anthocyanins are thus poorly absorbed by the body, no attempt has been made to improve the absorption of anthocyanins into the body, although at least tens to hundreds of mg must be taken. Nor has it been reported.

  Phytic acid is a general term for the hexaphosphate ester of myo-inositol, and is usually widely used in the plant world in the form of a salt, and industrially is a food material prepared from rice bran or corn steep liquor. This phytic acid has a metal ion chelating effect, a fermentation assisting action, a pH buffering action, etc., and is used to prevent struvite formation in shells such as salmon, salmon, shrimp and salmon, and to prevent blackening of shellfish. Yes. Furthermore, it is also used to prevent discoloration and color return of fruit juice and juice (see Patent Document 3). Further, recently, it has been found that it is effective in preventing colorectal cancer (see Patent Document 4). On the other hand, when phytic acid is taken orally, it has been known to inhibit the absorption of minerals such as calcium, magnesium and iron. However, the knowledge about the improvement effect of anthocyanin absorption has not been known.

  On the other hand, the present inventors have disclosed an invention relating to stabilization of a high anthocyanin-containing composition containing phytic acid (see Patent Document 5). However, there was no description on the absorption promoting properties of anthocyanins, and the amount of phytic acid added was low. Patent Document 3 describes a stabilization method by adding rutin and / or quercetin and phytin and / or phytic acid when a red cabbage pigment is added to a beverage or the like. In these methods, the amount of phytin added is recommended to be 100 ppm or less, which is extremely small compared to the present invention.

  As described above, the prior art does not show a measure for promoting the absorption rate of anthocyanins, and the use of phytic acid is only in the case where a small amount is used for stabilizing anthocyanins.

Japanese Patent No. 2967523 International Publication No. 01/01798 Pamphlet Japanese Patent Publication No. 5-67271 Japanese Patent No. 3188897 International Publication No. 01/048091 Pamphlet

  As described above, anthocyanins were considered to have an extremely poor absorption rate and low bioavailability even when compared with other flavonoids having a similar structure. And no method has been found to solve this problem. Under such circumstances, development of a substance that effectively absorbs anthocyanins in the body and exhibits sufficient physiological activity is required, and the present invention aims to solve such problems.

As a result of intensive studies to solve the above problems, the present inventors have found that phytic acid has an anthocyanin absorption promoting effect, and have completed the present invention.
That is, the present invention is an anthocyanin absorption promoter containing phytic acid as an active ingredient.
Furthermore, the present invention is an anthocyanin absorption promotion method characterized by using phytic acid added to anthocyanin.
Furthermore, the present invention is an anthocyanin-containing composition having anthocyanin absorption promoting ability, characterized by containing anthocyanin and phytic acid.

  In each of the above inventions, anthocyanins include those derived from blueberries, bilberries, cassis (black currant), and elderberries. Moreover, the preferable content of phytic acid is 80 mg to 2000 mg per 100 mg of anthocyanin

  By orally ingesting the absorption enhancer of the present invention or the anthocyanin-containing composition containing the absorption enhancer, more anthocyanins are absorbed into the body and their physiological activity can be exhibited more effectively. It was. That is, the effect can be exerted by taking a smaller amount of anthocyanin, and the residence time in the blood is extended, so that the physiological activity can be maintained for a longer period.

  Anthocyanins described in the present invention are a general term for compounds containing a skeleton as shown in the following structural formula. An aglycone alone is particularly called anthocyanidin, and a sugar-bound glycoside is particularly called anthocyanin (or anthocyanin). A substance in which a saccharide such as glucose is bound as a glycoside can also be called an anthocyanidin glycoside. That is, the anthocyanins of the present invention include anthocyanins, anthocyanidins, and anthocyanidin glycosides.

［式中、Ｒ^１およびＲ^２は、同一または異なって水素原子、水酸基またはメトキシ基を表し、Ｇｌｙは、グルコース、ルチノース、アラビノース、ガラクトースなどの糖類基を表す。］

[Wherein, R ¹ and R ² are the same or different and each represents a hydrogen atom, a hydroxyl group, or a methoxy group, and Gly represents a saccharide group such as glucose, rutinose, arabinose, galactose, or the like. ]

  Anthocyanins exist widely in nature, and are widely used in Europe as pharmaceuticals, quasi-drugs, cosmetics, etc., mainly due to their natural pigments and their functionality. For example, a valuable drug for use as a scar formation agent as described in JP-B-59-53883, or for treatment of diseases of peripheral blood vessels using blueberry-derived anthocyanins as described in Japanese Patent No. 2967523 Physical properties have been found. Recently, in Japan, other functions of anthocyanin are attracting attention as a method of using anthocyanins other than pigments.

  Anthocyanins of the present invention are mainly purple sweet potato, red cabbage, red radish, elderberry, grape juice or pericarp, purple corn, red radish, perilla, red rice, black rice, black beans, black sesame, cassis (black currant), Red currant, cowberry, gooseberry, cranberry, salmonberry, bilberry, strawberry, dark sweet cherry, cherry, hibiscus, hakulberry, blackberry, blueberry, plum, whiteberry, boysenberry, mulberry, purple potato, purple yam, It can be produced by extracting from a plant rich in anthocyanins such as raspberry, red currant, logan berry, saffron. The type of anthocyanin used in the present invention is not particularly limited, but the distribution of cyanidin, delphinidin, peonidin, petunidin, malvidin, pelargonidin glucoside, rutinoside, galactoside, arabinoside, dicurcoside, sambubioside and the like extracted from the above plant raw materials. Examples thereof include saccharides and acylated products thereof. Since the anthocyanin absorption promoting effect of the present invention was not particularly specific in these anthocyanins, it is considered that the same effect can be obtained for other anthocyanins and anthocyanins.

  For example, it may be anthocyanins crystallized such as delphinidin-3-glucoside, delphinidin-3-rutinoside and cyanidin-3-glucoside disclosed by the inventors in the pamphlet of WO 02/22847. These compounds are non-toxic and are shown to be present in the blood and organs when taken orally and can therefore be administered or taken orally.

  As raw materials, the above plant raw materials are desirable, and it is preferable to use raw fruits, dried fruits, fruit crushed materials, purees, fresh fruit juices, concentrated fruit juices and the like. Anthocyanins are solvent removal of these raw materials themselves, or processed products obtained by drying, chopping and grinding these raw materials, extracts obtained by adding a solvent to the processed products, and extracts obtained by removing the solvent from the extracts. In addition, fractions and purified products obtained by purifying the product, extract or solvent-removed product by column chromatography or liquid-liquid extraction are also included. When used for food applications, it is preferable to concentrate or extract the above raw materials in a membrane. When membrane concentration is performed, press filtration is required in advance, and before that, pectin inactivation treatment is preferably performed in order to reduce the viscosity of the filtrate. As an extractant in the case of extraction, water, polyhydric alcohols such as 1,3-butylene glycol, propylene glycol, glycerin and diglycerin, lower alcohols such as ethanol, isopropyl alcohol and propyl alcohol, solvents such as acetone, A mixed solvent, preferably water, a polyhydric alcohol, a lower alcohol, a mixed solvent thereof, more preferably water such as warm water or hot water is used. Examples of the form of the extract include an extract containing a solvent and a solvent removed product. However, in the present invention, it is preferable to use a fruit juice membrane concentrate as anthocyanin because the production of the raw material is easy and economical.

  The anthocyanin content of the anthocyanin-containing product of the present invention is determined by HPLC analysis of the preparation of each component of anthocyanin contained therein and measuring the response coefficient (mg / peak area) at 520 nm, which is the main color development region of anthocyanin. It is desirable to decide. However, the anthocyanin component for which no sample is present can be replaced with the response coefficient of the existing cyanidin 3-glucoside. In other words, the sample whose anthocyanin content is to be measured is analyzed by HPLC, the peak area of each component is multiplied by the response coefficient obtained from the standard, the content of each component is calculated, and the content is calculated from the ratio to the injection amount. Calculated as a percentage. Therefore, the content of anthocyanins includes not only the amount of anthocyanidins, which are aglycones, but also the amount of bound sugar.

  As the phytic acid used in the present invention, commercially available products can be used, but those extracted from rice bran, soybean whey, corn, corn steep liquor and the like are preferable. However, it is not limited to these and may be of any origin. The phytic acid content per 100 mg of anthocyanin is preferably 20 mg or more, but as shown in Example 1, it is more preferably 80 mg or more in order to dramatically increase the absorption rate. When the content is too small, the effective effect cannot be exhibited, and when the content is too large, phytic acid is too strong so that it is not suitable for drinking. Conventionally, phytic acid has been known as a stabilizer for anthocyanins, but the amount of phytic acid used for stabilization was sufficient in a small amount. An agent and a composition containing a large amount of phytic acid in anthocyanin having a phytic acid content of 80 mg or more per 100 mg of anthocyanin according to the present invention have not been known. That is, the content of phytic acid described in Japanese Patent Publication No. 5-67271 is much higher than the content of 100 ppm or less, and the usage form is clearly different.

  Food forms containing the anthocyanin absorption promoter of the present invention are beverages, tablet candy (tablets), hard candy, gummy, jelly and other desserts, yogurt, fruit sauce, syrup, water candy, capsule health food Even if the form is solid or liquid, the effect is obtained. The pharmaceutical product may be in any form such as powders, granules, tablets, capsules, syrups and the like.

  The present inventors have found several useful effects in a food composition containing a large amount of anthocyanins derived from cassis in International Publication No. 01/01798 pamphlet, and disclosed food and drink having functionality by blending this with food. is doing. The use of the absorption enhancer of the present invention may be a drug involved in expressing any physiological function. That is, these drugs include eyestrain, eyesight prevention, myopia, blood flow, anticancer, antiviral, antiallergy, anticholesterol, antihypertensive, antiarteriosclerosis Medicine and so on.

  The composition containing the anthocyanin absorption enhancer of the present invention makes use of the anthocyanin absorption promoting effect of the anthocyanin absorption enhancer, and is preferably used for such purposes. Examples of the composition of the present invention include foods, pharmaceuticals, and cosmetics. Among these, it is particularly preferable to apply to foods. In addition to the above-described anthocyanin absorption accelerator of the present invention, the composition can contain any components usually used in these compositions. As such optional components, for example, in the case of foods and pharmaceuticals, excipients, extenders, binders, thickeners, emulsifiers, coloring agents, fragrances, food additives, seasonings, and miso odorants, Examples include disintegrants, pH adjusters, preservatives, oxidation stabilizers, other nutritional ingredients, other medicinal ingredients, and active ingredients such as vitamins.

  Excipients in particular are those of the following categories: hydrophilic agents such as diluents, binders, lubricants, antioxidants, colorants, sweeteners, corrigents, sour agents, wetting agents, sorbitol and cyclodextrins. Gastroresistant film coatings of the type comprising an agent, an osmotic agent such as mannitol, a pH regulator, a stabilizer such as trehalose and mannitol, an adsorbent, a chelating agent and a sequestering agent, and cellulose acetyl phthalate and polymethacrylate An agent or the like is possible.

  In particular, among pH adjusters, acidifying agents of the type including citric acid, hydrochloric acid, lactic acid, tartaric acid, and monoethanolamine, diethanolamine and triethanolamine, potassium citrate, sodium bicarbonate, potassium citrate dihydrate Things can be mentioned.

  The composition of the present invention can be produced by treating these essential components and optional components according to a conventional method. The composition of the present invention thus obtained is excellent in the action of promoting absorption of anthocyanins into the body.

  Hereinafter, the present invention will be described more specifically with reference to Examples and Comparative Examples. However, the technical scope of the present invention is not limited to these examples.

Example 1 Anthocyanin Absorption Accelerator Blueberry Concentrated Fruit Juice 100g (Bx.65, Anthocyanin 0.9% (Anthocyanin 0.9g per 100g of Concentrated Juice)), Phytic Acid 50% Aqueous Solution 5 g was added to prepare 105 g of an anthocyanin absorption promoter.

(Example 2) Composition having anthocyanin absorption promoting ability (1)
As anthocyanin, Cassis polyphenol 20 (manufactured by Meiji Seika Co., Ltd.) was used. This is an anthocyanin extract obtained by membrane concentration and ethanol extraction from cassis, and is a powder containing 24.1% by weight of anthocyanin. Dissolve 1g of this powder in 20ml of distilled water and add 50% aqueous solution of phytic acid as shown in Table 1 as phytic acid (food additive, manufactured by Tsukuno Food Industry Co., Ltd.) to promote the absorption of anthocyanins. Compositions (1-1) to (1-4) having were prepared.

(Example 3) Composition having anthocyanin absorption promoting ability (2)
As anthocyanins, elderberry anthocyanin powder (manufactured by iprona, rubini, anthocyanin content 20% by weight) and bilberry anthocyanin powder (manufactured by Tokiwa Plant Chemical Laboratories, Inc., bilberon 25, anthocyanin content 25% by weight) were used. Dissolve 1 g of elderberry anthocyanin powder in 20 ml of distilled water, and add 0.4 g of 50% phytic acid solution (manufactured by Tsukuno Food Industry Co., Ltd., food additive) as phytic acid to enhance anthocyanin absorption (2) Was prepared. Also, 1 g of bilberry anthocyanin powder is dissolved in 20 ml of distilled water, and 0.4 g of 50% phytic acid solution (manufactured by Tsukuno Food Industry Co., Ltd., food additive) is added as phytic acid to enhance anthocyanin absorption (3 ) Was prepared.

(Example 4) Anthocyanin absorption promoting effect in rats In this test, the compositions (1-1) to (1-4) having anthocyanin absorption promoting ability of Example 2 were used as the anthocyanin composition. Wistar male rats aged 7 weeks old were fasted for 16 hours for 6 rats in each group, and the above compositions (1-1) to (1-4) were orally administered to the stomach once. The test section has a composition as shown in Table 1 of Example 2. Prior to administration to rats, urine was collected up to 4 hours after administration, 4 to 6 hours after administration, and 8 to 24 hours after administration, and the amount of anthocyanin excreted in urine was already reported (Matsumoto et. Al. J. Agric. Food. Chem. 49 (3), 546-1551, 2001). Anthocyanins were not detected in the urine before administration. The results are shown in FIG. From this figure, it can be seen that as the amount of phytic acid added increases, the amount of urinary excretion of anthocyanins increases and the amount of anthocyanins absorbed increases. In particular, it can be seen that by adding 83 mg or more of phytic acid per 100 mg of anthocyanin, the amount of absorption is dramatically increased 10 times or more. In addition, the group with a phytic acid content of 41 mg or less per 100 mg of anthocyanin has the maximum excretion up to 4 hours after administration, whereas the group with a phytic acid content of 83 mg or more has a group of 4-8 hours after administration. However, the amount of excretion was maximum, and an increase in residence time in blood could be expected.

(Example 5) Anthocyanin absorption promoting effect in rats In this test, the compositions (2) and (3) having the anthocyanin absorption promoting ability of Example 3 were used as the anthocyanin composition.

  The test method was the same as in Example 4. After fasting three 7-week-old Wistar male rats in each group for 16 hours, the above compositions (2) and (3) were administered orally once in the stomach. The amount of anthocyanin excreted in urine was measured after collecting urine up to 24 hours. As in Example 4, the test area is 1 g of powder per 1 kg body weight (200 mg as anthocyanin for elderberry, 250 mg as anthocyanin for bilberry). Four groups were set for the test. That is, phytic acid + elderberry group (200 mg phytic acid, 200 mg anthocyanin per kg body weight), elderberry group (200 mg anthocyanin per kg body weight), phytic acid + bilberry group (200 mg phytic acid per kg body weight, 250 mg anthocyanin), bilberry Compared to the group (250 mg of anthocyanin per kg body weight). The total amount of urine excreted up to 24 hours is shown in Table 2. In the phytic acid-containing section (Elderberry 100 mg anthocyanin, phytic acid 100 mg, Bilberry 100 mg anthocyanin 80 mg phytic acid 80 mg), Elderberry 4 times and Bilberry 11 times more excreted in urine. It was confirmed that even elderberry and bilberry have an absorption promoting effect.

(Example 6) Anthocyanin absorption promoting effect in humans As in Example 4, the anthocyanin composition was Cassis Polyphenol 20 (Meiji Seika Co., Ltd.) as anthocyanin, and phytic acid was a 50% aqueous solution of phytic acid (Tsukino Food Industry Co., Ltd.). Manufactured, food additive).

Six healthy men (age 38.2 ± 3.4 years old, weight 73.5 ± 16.9 kg) were fasted for 12 hours, and then the test food was taken. The test foods were the following two types, and 4 mg as anthocyanin and 16.6 mg as cassis polyphenol 20 per kg body weight.
1) Cassis polyphenol 20 powder was dissolved in water and drunk.
2) Cassis polyphenol 20 powder was dissolved in 1% phytic acid aqueous solution and drunk.

  Blood samples were collected before and after ingestion to measure the anthocyanin dynamics in the blood. In addition, urine was collected every 2 hours, and the transition of urinary excretion was measured. The amount of anthocyanin excreted in blood and urine was analyzed according to a previous report (Matsumoto et. Al., J. Agric. Food. Chem. 49 (3), 1546-1551, 2001). The average value of anthocyanin concentration in the blood of six subjects is shown in FIG. 2, and the average value of urinary excretion is shown in Table 3. In the group containing 1% phytic acid, the blood concentration increased on average by about 3 times, and the residence time of anthocyanins in the blood was prolonged. In addition, the amount of urinary excretion also increased dramatically, averaging about 5 times.

(Comparative example 1) Absorption promotion effect of anthocyanin by citric acid As a comparative example, the absorption promotion effect of anthocyanin was compared using citric acid.
As in Example 6, Cassis polyphenol 20 (manufactured by Meiji Seika Co., Ltd.) was used as anthocyanin, and a food additive manufactured by Wako Pure Chemical Industries, Ltd. was used as citric acid.

Four healthy men and women (age 42.3 ± 7.8 years old, weight 69.1 ± 23.6 kg) were fasted for 12 hours, and then the test food was taken. The test foods were the following two types, and 4 mg as anthocyanin and 16.6 mg as cassis polyphenol 20 per kg body weight.
1) Cassis polyphenol 20 powder was dissolved in water and drunk.
2) Cassis polyphenol 20 powder was prepared by dissolving 1.8 g of citric acid in water to a total of 60 g. The citric acid concentration is 3%.

  Blood samples were collected before and after ingestion to measure the anthocyanin dynamics in the blood. In addition, urine was collected every 2 hours, and the transition of urinary excretion was measured by the same method as in the example. Table 4 shows the average values of excretion into the urine of four subjects. Unlike phytic acid shown in Example 6, in the citric acid-containing section, the urinary excretion amount decreased to about one-third on average, and it was found that the absorption promoting effect was low.

Recovery of cassis anthocyanin in urine in rats. Changes in blood levels of anthocyanins

Claims (2)

  An anthocyanin absorption promoter containing phytic acid as an active ingredient.   2. The anthocyanin absorption promoter according to claim 1, wherein the anthocyanin is derived from blueberry, bilberry, cassis (black currant), and elderberry.

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