JP6044944B2 - Process for producing new processed ume products and functional composition, food composition, and pharmaceutical composition using the same - Google Patents

Description

  The present invention relates to a concentrated extract of plum pulp (hereinafter referred to as “plum extract”), a concentrated extract of plum juice (hereinafter referred to as “plum juice extract”), and a concentrated extract of plum vinegar (hereinafter referred to as “plum vinegar extract”). Or, in the process of producing concentrated plum extract such as desalted plum vinegar extract (hereinafter referred to as “desalted plum vinegar extract”), it retains a considerable amount of polyphenols, a useful component of plum, while furfurals associated with heat production Production method (hereinafter referred to as the present production method) with controlled production of ume, which is completely different from conventional plum extract such as plum extract, plum juice extract, plum vinegar extract or desalted plum vinegar extract and its production Regarding the law. Furthermore, it is related with the functional composition obtained by this manufacturing method, and the foodstuff composition and pharmaceutical composition containing this.

  Ume has been known as a healthy food since ancient times, and has been used in various forms such as dried plums, plum juice drinks, and confectionery. In addition, in the case of digestive disorders such as dyspepsia and per meal, ume extract, which is obtained by heating and concentrating plum pulp, is used as a folklore medicine for digestive disorders. In addition, immature ume fruit is made into a traditional Chinese medicine called "Toriume", which is mainly used for digestive diseases.

  Polyphenol has attracted attention as a functional substance involved in the health function of fruits. Polyphenol is a general term for plant components having a plurality of phenolic hydroxyl groups (hydroxy groups) in the same molecule. Polyphenols are said to have antioxidant activity and are effective in preventing lifestyle-related diseases such as arteriosclerosis, stroke, myocardial infarction, diabetes and osteoporosis in addition to anti-carcinogenic activity.

  It is thought that polyphenols contained in plums are also involved in the health functions handed down in plums.

  About 1000 ppm of polyphenols are present in the plum fruit. We have been researching this polyphenol. In particular, we have developed a method for mass production of fruit-derived polyphenols (hereinafter referred to as “plum vinegar polyphenols”) from ume vinegar produced during the production of plum dried, and reported on its chemical analysis and health promotion action (Patent Document 1). Plum vinegar polyphenols are characterized in that citric acid derived from plum fruits and salt added in large quantities during plum drying are removed.

  A functional composition of ume vinegar polyphenol, and an enzyme inhibitor having an α-amylase inhibitory activity and an α-glucosidase inhibitory effect effective for the treatment and prevention of obesity and diabetes, as well as a food composition and specified health care Patents relating to food compositions, quasi-drug compositions, and pharmaceutical compositions have been filed (Patent Document 1). Furthermore, the present inventors have found and published an effect of suppressing an increase in blood pressure with ume vinegar polyphenol. (Non-Patent Document 1)

  The present inventors conducted a safety test of ume vinegar polyphenols and conducted mutagenicity tests such as rat acute toxicity test, rat 28-day subacute toxicity test, mouse 90-day chronic toxicity test, UMU test and mouse micronucleus test. And revealed that it is extremely safe (Non-patent Document 2)

  Siringalesinol, a kind of lignan derivative isolated from plum, has been reported to have an antibacterial action against Helicobacter pylori living in the gastric mucosa (see, for example, Non-Patent Document 3).

  In umeshu, there is rioniresinol, a lignan derivative that is a kind of polyphenol. It is known that this rioniresinol has an antioxidant action (for example, refer nonpatent literature 4).

  It has been reported that chlorogenic acid, which is a kind of polyphenol contained in an extract of plum fruit, has an angiotensin converting enzyme inhibitory activity, an enzyme that converts angiotensin I to angiotensin II that increases blood pressure (non- Patent Document 5).

The plum extract obtained by heating and concentrating plum juice is produced by heat treatment during production to produce 5-hydroxymethyl-2-furfural (hereinafter referred to as HMF) by dehydration of sugars such as glucose and sucrose. It is known that this further produces umefural and the like by ester condensation with citric acid (Non-patent Document 6).
In addition, it has been reported that umefural contained in ume meat extract exhibits an effect of improving blood flow (Non-patent Document 7 and Patent Document 2).

  Moreover, it is reported that the active ingredient which shows the blood flow improvement effect | action of the ground yellow which is a crude drug is HMF (nonpatent literature 8).

  On the other hand, it has been reported that HMF is metabolized to sulfoxymethylfurfural having mutagenicity by liver sulfotransferase (Non-patent Documents 9 and 10).

JP 2009-137929 A JP-A-11-228561

Junpei Yamazaki, 8 others, “Action of Plum Vinegar Polyphenols on SHR Blood Pressure,” Abstracts of Annual Meeting of the Agricultural Chemical Society of Japan, 2011 Annual Meeting p. 62 Yusuke Shiga, Takenori Tsuchida, Takehiro Hara, Kunihiro Kishida, Masanobu Maeda, Kazuhisa Miyashita, Maki Fujiwara, Hayako Yamanishi, Fumiko Yano, Takahiko Mitani Bulletin of Department of Biophysics, Kinki University (2011) Otsuka T, et al., 9 others, “Suppressive effects of fruit-juicecento of Prune cc. on Helicobacter pylori-induced glandular stromachlesin mongolian gerbils.), “Asia Pacific Journal of Cancer Prevention (Asia Pacific Journal of Cancer Pv. 6), Asia Pacific Journal of Cancer Pac. 337-341 Shirasaka Noriaki, 7 others, “Antioxidation of Plum Wine and Isolation and Identification of Antioxidants”, Journal of Japan Society for Food Science and Technology, 1999, Vol. 46, p. 792-798 Ina H (Ina H) and three others, “Effects of Benzoyl glucoside and chlorogenic acid from ume on the plasma levels of corticosteroid (ACTH) and catecholamines in plasma of experimental menopausal rats Acid from Prunusumume on adrenocorticotrophone (ACTH) and categorical levels in Japan of L & B (IC) 2004, Vol. 27, p. 136-137 Ga rattan et al., Journal of hemorheology, (3), p81-87, 2000 Chuda Y. et al. et al. , J. et al. Agric. Food Chem. 47, p828-831, 1999 Matsuda, The 51st Annual Meeting of the Japanese Biopharmaceutical Society, 1A-S1,2000 B. H. Monien et al., Chem. Res. Toxicol. 2009, 22, 1123-1128. Klaus Abraham et al. Mol. Nutr. Food Res. 2011, 55, 667-678

  The object of the present invention is to concentrate polyphenols in the plum pulp, plum juice, plum vinegar, or desalted plum vinegar while suppressing degradation and inhibiting or controlling the production of furfurals such as HMF. It is to provide a new plum extract, a new plum juice extract, a new plum vinegar extract, or a desalted plum vinegar extract (hereinafter collectively referred to as “new plum concentrate extract”) and a method for producing the same.

  Another object of the present invention is to produce a functional composition using a novel concentrated extract having a high polyphenol content.

  As a result of intensive studies to solve the above problems, the present inventors concentrated polyphenols at a high concentration by concentrating plum raw materials such as plum pulp, plum juice, plum vinegar, or desalted plum vinegar in a predetermined temperature range. The present inventors have found that a novel plum concentrated extract with a content of furfurals can be obtained and the present invention has been completed.

The present invention relates to the following plum concentrate extract item 1. A method for producing an enriched plum extract substantially free of furfural, wherein the plum raw material is concentrated at a temperature of 85 ° C. or lower.
Item 2. Item 2. The method for producing an enriched plum extract according to Item 1, wherein the temperature during concentration is 40 to 80 ° C.
Item 3. A method for producing an enriched plum extract containing both plum polyphenol and furfural, wherein the plum raw material is concentrated at a temperature of 80 ° C. or higher and lower than 100 ° C.
Item 4. Item 4. The method for producing an enriched plum extract according to Item 3, wherein the temperature during concentration is 80 to 95 ° C.
Item 5. Item 5. The method for producing an enriched plum extract according to any one of Items 1 to 4, wherein the plum material is selected from the group consisting of plum pulp, plum juice, plum vinegar, and desalted plum vinegar.
Item 6. Plum concentrate extract that is substantially free of furfural and has a residual ratio of neochlorogenic acid and chlorogenic acid of 95% or more.
Item 7. A plum concentrated extract containing furfural, neochlorogenic acid and chlorogenic acid, wherein the residual rate of neochlorogenic acid is 50% or more and the residual rate of chlorogenic acid is 90% or more.
Item 8. Item 8. A functional composition comprising, as a main ingredient, a plum concentrated extract obtained by the production method according to any one of items 1 to 5, or a plum concentrated extract according to item 6 or 7.
Item 9. Item 9. The functional composition according to Item 8, which is a food composition, a quasi-drug composition, or a pharmaceutical composition.

  It is preferable that the functional composition of this invention contains the novel plum concentrated extract obtained by the said manufacturing method.

  Moreover, this invention is a food composition and a pharmaceutical composition containing the said functional composition.

  According to this invention, the functional composition comprised using the novel plum concentrated extract can be obtained. The functional composition of the present invention is rich in polyphenols and is substantially free of furfurals such as HMF, or the content thereof is controlled and is a concentrate, so it is added to general foods, etc. And you can expect a health promotion effect. In addition, the polyphenol used by this invention has safety | security. Therefore, the functional composition of the present invention can be taken for a long time.

FIG. 1 is a high-performance liquid chromatogram showing the effect of heat concentration conditions on the production of furfurals and the degradation of polyphenols in plum juice.

  The method for producing a new concentrated plum extract according to the present invention does not decompose plum phenol, plum juice, plum vinegar, or desalted plum vinegar, or leave 50% or more before concentration, and substantially contain furfurals such as HMF. Do not make it, or concentrate it under the condition that it is produced in an amount of 50% or less compared to conventional plum meat extract ume vinegar extract or the like. The heating and concentration temperature at this time is less than 100 ° C., preferably 95 ° C. or less, more preferably 90 ° C. or less, further preferably 85 ° C. or less, and particularly 80 ° C. or less. Although the minimum of the temperature at the time of concentration is not specifically limited, Usually, it is room temperature or more, Preferably it is 30 degreeC or more, More preferably, it is 40 degreeC or more, More preferably, it is 50 degreeC or more, Especially 60 degreeC or more. When increasing the content of umefural, the temperature during concentration is preferably 80 ° C. or higher, for example, 80 ° C. to less than 100 ° C., preferably 80 ° C. to 95 ° C., more preferably 80 ° C. to 90 ° C., and particularly 80 ° C. to 85 ° C. Is mentioned. The concentration temperature for the production of the plum concentrated extract substantially free of umefural is room temperature to 80 ° C, preferably 40 to 80 ° C, more preferably 50 to 75 ° C. Since the decrease (decomposition) of polyphenol and the increase (generation) of umefural are determined by temperature and time, the content of polyphenol and umefural can be controlled by controlling these. In the examples, the amount of furfural is detected. However, when furfural is produced, furals such as umefural are produced, and therefore furfural is detected as an index of the content of fulars containing umefural.

  The novel plum concentrated extract of the present invention may contain a part of this extract. The novel concentrated extract of the present invention contains many kinds of polyphenols. Among these, a polyphenol used for a specific purpose may be subjected to a sorting process such as filtration, column treatment, and solvent washing. Neochlorogenic acid and chlorogenic acid are particularly important as polyphenols in plum. Since neochlorogenic acid is stable by heat, the content of the concentrated plum extract should remain at 50% by weight or more, preferably 90% by weight or more, more preferably 95% by weight or more before concentration and heating. In addition, since chlorogenic acid is easily decomposed by heat, the content of the concentrated plum extract remains 30% by weight or more, preferably 50% by weight or more, more preferably 90% by weight or more, particularly 95% by weight or more before the concentration heating. It is good.

  There is no restriction | limiting in particular in the form of the functional composition of this invention, A solution, solid may be sufficient, and a mixture with another compound may be sufficient. In the case of a mixture, it may be spray-dried, freeze-dried, or added with a shaping agent such as dextrin.

[Functional composition]
The functional composition of the present invention can be used as it is, but if necessary, various components and additives used in pharmaceuticals, quasi drugs, foods, beverages and the like shown below. The products suitable for the application can be arbitrarily selected and used in combination to make each product form easy to use.

  When the functional composition of the present invention is used for a pharmaceutical product, it can be administered orally. The novel concentrated extract can be formulated with a pharmaceutical carrier and used in the form of tablets, capsules, drinks, troches, solutions, granules, powders and the like. In that case, conventional ingredients such as excipients, lubricants, binders, disintegrants, solvents, suspending agents, stabilizers, colorants, sweeteners and the like can be added as appropriate.

  For example, when ingested orally, it can be ingested by adding to food as a food additive. When used as a food additive, the amount added is not particularly limited, and may be appropriately determined according to the type of food. For example, liquid foods such as soft drinks and carbonated drinks, and solid foods such as confectionery and other various foods can be added and used. In addition, an example of an administration method when administered to the human body as food is as follows. Administration can be performed by various methods, for example, oral administration using tablets, capsules, granules, syrups and the like. The oral preparation can be produced according to a normal production method. For example, excipients such as starch, lactose and mannitol, binders such as sodium carboxymethylcellulose and hydroxypropylcellulose, disintegrants such as crystalline cellulose and carboxymethylcellulose calcium, lubricants such as talc and magnesium stearate, light anhydrous It can be produced as a tablet, capsule, granule, etc. by appropriately combining and formulating a fluidity improver such as silicic acid.

  Specific examples of the use of the functional composition of the present invention in foods include so-called health foods, functional foods, dietary supplements, supplements, foods for specified health use, combined foods for the sick and sick (Ministry of Health, Labor and Welfare) , Special-purpose foods) or elderly foods (Ministry of Health, Labor and Welfare, special-purpose foods). In that case, uncoated tablets, film-coated tablets, dragees, granules, powders, tablets, capsules (hard capsules) And soft capsules.), Chewable type, syrup type, drink type, etc. Specific food products include processed fishery products such as kamaboko, chikuwa, hanpen, processed meat products such as sausage, ham, and wiener, agricultural processed products such as tofu, fried chicken, and konjac, western confectionery, Japanese confectionery, bread, cake Jelly, pudding, snacks, cookies, gum, candy, ramune and other confectionery, raw noodles, Chinese noodles, buckwheat, noodles and other noodles, sauce, soy sauce, dressing, mayonnaise, sauce, honey, powdered candy, syrup , Curry powder, mustard powder, pepper powder and other spices, jams, marmalade, chocolate spreads, pickles, green vegetables, sprinkles, processed vegetables and fruits such as canned and bottled vegetables, fruits, cheese, butter, yogurt, etc. Dairy products, fruit juices, vegetable juices, whey beverages, soft drinks, health teas, medicinal alcoholic beverages, etc. Strong tablets for health for the purpose of (supplement), etc., beverages, food products such health-oriented granulate, etc., animal feed, pet food, etc. as a target.

  The functional composition of the present invention includes quasi-drugs (in-mouth fresheners, dental care, skin care, hair preparations, bath preparations, powdered meals, drinks, healthy stomach fresheners, etc.), animal foods (pet foods) Etc.), animal feed, plant fertilizer and the like.

  The functional composition of the present invention may use additives generally used for granulation, such as excipients, binders, disintegrants, lubricants, talc, and fluidity improvers. For example, starch, lactose, crystalline cellulose such as sodium mannitol carboxymethylcellulose and hydroxypropylcellulose, light anhydrous silicic acid such as carboxymethylcellulose calcium and magnesium stearate, cellulose acetate, chitosan, sodium alginate, calcium alginate, defatted rice sugar , Oil cake, soy flour, wheat flour, silicic anhydride, bran, rice bran flour, calcium carbonate, milk calcium, magnesium oxide, sodium bicarbonate, crystalline cellulose, starch, brewer's yeast, sugar, reduced lactose, vegetable oil By combining and prescribing, it can be produced in the form of tablets, capsules, granules and the like.

  In addition, various additives derived from plant or animal raw materials and other additives can be used in combination as required. These additives are processed in a conventional manner according to the product type and form to be added (for example, grinding, milling, washing, hydrolysis, fermentation, purification, pressing, extraction, fractionation, filtration, drying) , Powdering, granulation, dissolution, sterilization, pH adjustment, deodorization, decolorization, etc., may be arbitrarily selected and combined), and may be selected arbitrarily from various materials. In addition, what is necessary is just to select the solvent used for extraction, considering the usage of the product to be provided, the processing performed later, and the like.

  The functional composition of the present invention includes other moisturizing agents, hormones, sequestering agents, pH adjusting agents, chelating agents, antiseptic / antibacterial agents, cooling agents, stabilizers, emulsifiers, animal / plant proteins and Decomposition product, animal / plant polysaccharide and decomposition product thereof, animal / plant glycoprotein and decomposition product thereof, blood flow promoter, anti-inflammatory agent / antiallergic agent, cell activator, foam enhancer, thickener, Oral preparations, deodorants / deodorants, bitters, seasonings, fermented or the like may be used in combination. By combined use with these, additive and synergistic effects can be expected.

  The safety of the polyphenol contained in the functional composition of the present invention is determined by known safety tests, for example, acute toxicity test in which a single functional composition is administered to rats, repeated oral administration of the functional composition for 28 days. It can be confirmed by a sub-acute toxicity test, a chronic toxicity test in which a functional composition is orally administered to mice for 90 days, a UMU test using Salmonella as a mutagenicity test, a mouse micronucleus test, and the like. The safety of the functional composition of the present invention is confirmed in these tests. As a result, long-term use can be achieved.

(Measurement method of polyphenol residual rate in new plum juice extract)
The following experiment was conducted in order to examine the heating and concentration conditions of plum juice.
Minamitakaume (green fruit stage) was squeezed, and 200 g of the obtained fruit juice was concentrated and dried under the following four conditions (A to D). Condition A (direct flame treatment 100 ° C or higher), condition B (boiled water treatment 90 ° C or higher), condition C (rotary evaporator treatment 80 ° C), condition D (rotary evaporator treatment 60 ° C), chlorogenic acid after redissolving the residue Using polychlorogenic acid as an index, the residual ratio of polyphenol and the presence or absence of furfurals were analyzed by HPLC. The results are shown in FIG. Table 1 shows the effect of heat concentration conditions on the formation of furfurals and the degradation of polyphenols in plum juice.

  Further, Table 2 shows the results of confirming by HPLC the amounts of polyphenol and furfural when changing the heating temperature and heating time of ume pulp. It is clear that furfural forms rapidly at 100 ° C and polyphenols disappear rapidly.

(HPLC analysis conditions)
Apparatus: LC-2010 (manufactured by SHIMADZU)
Mobile phase: 0.1% trifluoroacetic acid aqueous solution: methanol (75:25, v / v)
Column: Hydrosphere C18, 4.6 × 250 mm (manufactured by YMC)
Sample injection volume: 30 μl
Temperature: 40 ° C
Measurement wavelength: 280 nm
Flow rate: 1 ml / min

  According to FIG. 1 and Table 1, a large amount and a large amount of furfurals including HMF were generated under the condition A (open flame treatment of 100 ° C. or more), and the polyphenols chlorogenic acid and neochlorogenic acid disappeared. Production of furfurals was also observed under condition B (boiled water treatment of 90 ° C. or more), and the residual rates of chlorogenic acid and neochlorogenic acid were 94.6% and 52.6%, respectively. In conditions C (rotary evaporator treatment 80 ° C.) and condition D (rotary evaporator treatment 60 ° C.), the formation of furfurals was not observed, and polyphenols remained almost undecomposed (condition C: chlorogenic acid (97 0.4%) neochlorogenic acid (97.0%), condition D: chlorogenic acid (98.7%) neochlorogenic acid (99.1%)). Also in the high performance liquid chromatogram, it is clear that the chromatogram of condition C is the same as the chromatogram of the original juice before heating.

  According to Table 2, furfural is not generated during concentration at 75 ° C or lower, and may not be generated by controlling the time at 80 ° C (60 minutes or less) or may be generated (90 minutes or more, particularly 120 minutes or more). )it can. When producing furfural, it is preferably 80 ° C. or higher, particularly 85 ° C. or higher. On the other hand, polyphenols decompose at a relatively short time at 95 ° C. and quickly at 100 ° C. Therefore, in order to obtain a plum concentrated extract sufficiently containing polyphenol, a short time under reduced pressure is required at a concentration temperature of 95 ° C. The concentration of time is good, and it is desirable that the heating time is short even at 90 ° C. If it is 85 degreeC, even if it heats for a certain period of time, sufficient amount of polyphenol will remain | survive, and at 80 degreeC, the amount of polyphenol before concentration can fully be maintained.

  Thus, it became clear that the amount of polyphenol and furfural (index of memefural) in the plum concentrated extract can be controlled by the temperature and concentration time during concentration.

In Table 1, the amount of furfural “++” indicates that about 50% or more of the full-plum extract of the plum concentrated extract such as the conventional plum meat extract is produced, and “+” indicates the plum concentration such as the plum extract. It shows that the amount of furfural about 10-50% of the extract was detected.

In Table 2,
+/- indicates that the amount of neochlorogenic acid is 90% or more before concentration, the amount of chlorogenic acid is 50% or more before concentration, and furfural is substantially not detected.
+ / ± indicates that the amount of neochlorogenic acid is 90% or more before concentration, the amount of chlorogenic acid is 50% or more before concentration, and furfural is detected about 0.1 to 10% of conventional plum extract It shows that.
+ / + Means that the amount of neochlorogenic acid is 90% or more before concentration, the amount of chlorogenic acid is 50% or more before concentration, and furfural is detected about 10 to 50% of conventional plum extract. Show.
± / + means that the amount of neochlorogenic acid is 30 to 90% before concentration, the amount of chlorogenic acid is 10 to 50% before concentration, and that furfural is detected more than 10% of the conventional plum extract. Show.
-/ + Indicates that the amount of neochlorogenic acid is 30% or less before concentration, the amount of chlorogenic acid is 10% or less before concentration, and furfural is detected at 10% or more of the conventional plum extract.

  From the above, it has been found that by concentrating plum juice at 90 ° C. or lower, desirably 80 ° C. or lower, a new plum juice extract containing polyphenols at a high concentration and containing no furfurals can be obtained.

  The novel plum concentrated extract of the present invention contains a high concentration of polyphenols and does not contain furfurals such as HMF, which are feared for mutagenicity, and thus is a composition that is highly safe and can be expected to promote health. Moreover, since the polyphenol derived from ume is extremely safe and has also been shown to have a health promoting effect, the functional composition obtained in the present invention can be added to foods, pharmaceuticals, and the like.

Claims (3)

In a method for producing a food composition containing a plum concentrate,
A plum raw material selected from plum flesh and plum juice is concentrated at a temperature of 60 to 75 ° C. , and is not heated to 80 ° C. or more, substantially free of furfural , neochlorogenic acid and chlorogenic acid The manufacturing method including the process of manufacturing the said plum concentration extract whose both residual ratios are 95% or more . In the manufacture of quasi-drug compositions containing plum concentrate extract,
A plum raw material selected from plum flesh and plum juice is concentrated at a temperature of 60 to 75 ° C., and is not heated to 80 ° C. or more, substantially free of furfural, neochlorogenic acid and chlorogenic acid The manufacturing method including the process of manufacturing the said plum concentration extract whose both residual ratios are 95% or more. In a method for producing a pharmaceutical composition containing a plum concentrated extract,
A plum raw material selected from plum flesh and plum juice is concentrated at a temperature of 60 to 75 ° C., and is not heated to 80 ° C. or more, substantially free of furfural, neochlorogenic acid and chlorogenic acid The manufacturing method including the process of manufacturing the said plum concentration extract whose both residual ratios are 95% or more.

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