JP2005145933A - Flavonoid composition - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To obtain a flavonoid composition that has reduced astringent taste while remaining physiological effect of flavonoids including feces-deodorizing effect, thus this flavonoid composition can be applied to a wide range of food and beverage by solving the problem that flavonoids have peculiarly strong astringency and the acceptable intake is harshly limited and very difficult, because flavonoids cause excessive numbness in the mouth with unpleasant sensation. <P>SOLUTION: This flavonoid composition includes a flavonoid whose surface is coated with a high molecule bearing uronic acid residual groups. In another embodiment, the high molecule bearing the uronic acid residual groups contains a polyvalent metal ion in the flavonoid composition. <P>COPYRIGHT: (C)2005,JPO&NCIPI

Description

  The present invention relates to a flavonoid composition in which the taste of flavonoids is improved without impairing physiological functions after ingestion of flavonoids orally.

Flavonoids are contained in various plants such as tea, apples, grapes and beans, and have various physiological effects including strong antioxidant action. It is used for various foods and drinks.
As a physiological function of flavonoids, for example, it is considered that anthocyanidin, which is a kind of flavonoid in red wine, suppresses oxidation of LDL cholesterol and prevents heart disease.
Quercetin, catechin, etc., which are a kind of flavonoid in cocoa beans, are known to exhibit antioxidant effects, and further, preventive action against alcoholic gastric mucosal damage and allergy suppressing action (inhibition of human T lymphocyte proliferation) It is known that there is an action and an antibody production inhibitory action by B lymphocytes).
Catechins, one of the flavonoids in green tea, also have anti-oxidant effects, researches have been conducted on cancer and arteriosclerosis preventive effects, and reports on fecal deodorization effects and blood pressure elevation-inhibiting effects are also known. ing.
Isoflavones, a kind of flavonoids in soybean, have been reported in animal experiments to suppress skin cancer and lung cancer and prevent osteoporosis.

Currently, as the aging of society progresses at an accelerated pace, the number of elderly people in need of care has increased, and fecal odor has become a significant source of stress for the person, those who live together or who are involved in care. This odor often leads to a disruption of mental balance. In addition, young women tend to endure constipation outside their homes because of their stool odor, which is a factor in causing constipation.
On the other hand, with regard to malodors in animals, complaints of malodours in livestock are always at the top, and it is always desirable to reduce the smell of feces and urine excreted by industrial animals such as cattle, pigs, horses and chickens. . In recent years, in Japan, with the increase in the elderly population and the nuclear family, the number of families keeping pets has increased rapidly. Especially when they are raised indoors, the smell of pet droppings has become a problem for owners. The number of malodorous complaints that are classified as so-called cities and lifestyles, such as “individual housing / apartments / dormitories”, is increasing. Accordingly, food materials and animal feeds that have a function of deodorizing malodorous substances in feces safely and effectively are strongly desired.
For these reasons, it has become a social demand to reduce or eliminate fecal odor, and among the physiological functions of flavonoids, attention has been paid to the fecal deodorizing effect and research has been conducted.

  Examples of fecal deodorization effects include 35 volunteers who observed the fecal deodorization effect when 300 mg of tea catechin per day was orally ingested for 6 weeks (see Non-Patent Document 1), and the defecation of livestock and pets. An effect of deodorizing (for example, see Patent Document 1) is known.

However, since flavonoids have a unique and strong astringency, when they are ingested as they are, their amount is naturally limited. When a large amount of flavonoid is ingested, it causes discomfort accompanied by severe numbness in the oral cavity, so it is extremely difficult to ingest a large amount of flavonoid as it is. For this reason, in the field of health foods based on flavonoids, tablets (including sugar-coated tablets) or capsules are often used, but powders, granules, There were few products such as liquid.
As a method of reducing astringency while leaving the fecal deodorizing effect, the present applicants have found a method of coating fat and oil on proanthocyanidins, which are flavonoids in grape seeds, in the presence of a polyhydric alcohol fatty acid ester. (See Patent Document 2) However, when applied to foods and drinks, emulsion breakdown may occur under acidic conditions, or the oil coating may be broken by a long heating process, and astringency will be felt again. It turns out that there may be cases.

Koichi Goto et. al. "The Effects of TeaCatechins on Fecal Conditions of Elderly Residents in Long-Term Care Facility" (J. Nutri. Sci. Vitamol, 1999, 45, 135-141). JP-A-5-51 (Page 2-5) Japanese Patent Laid-Open No. 2002-29968 (page 2-9)

  The subject of this invention is providing the flavonoid composition which reduced astringency, and the food / beverage products containing it, leaving the physiological effect including the fecal deodorizing effect which can be used for a wide variety of food / beverage products.

  As a result of intensive studies to solve the above problems, the inventors of the present application coated a plant extract containing a flavonoid as a main component with a polymer having a uronic acid residue. The present inventors have found that a flavonoid composition with improved taste can be provided without impairing physiological effects including effects, and completed the present invention.

  The flavonoid composition characterized by containing a flavonoid coated with a polymer having a uronic acid residue obtained in the present invention has improved taste and reduced astringency and bitterness of the flavonoid. ing. This effect is not lost by heating under acidic conditions, and the flavonoid's in vivo absorbability and fecal deodorizing effect are not impaired, so various foods and drinks can be eaten while maintaining the physiological function of the flavonoid. It can be applied to products.

  The polymer having a uronic acid residue used in the present invention is not particularly limited, and examples thereof include pectin, alginic acid, fucoidan, gum arabic, xanthan gum, dermatan sulfate, chondroitin sulfate, chondroitin, hyaluronic acid, heparin and the like. 1 type or 2 types or more selected from these groups can be used. From the viewpoint of coating formation, one or more selected from the group of pectin, alginic acid or a metal salt thereof is preferable, and alginic acid or a metal salt thereof is more preferable.

In the present invention, in order to make the coating of the polymer having a uronic acid residue stronger, it is desirable to contain a polyvalent metal ion, and it is more desirable to perform crosslinking with the polyvalent metal ion.
Here, the polyvalent metal of the polyvalent metal ion is not particularly limited, and examples thereof include calcium, zinc, magnesium, barium, strontium, copper, iron, aluminum, and cobalt. Of these, calcium, zinc, magnesium, and barium are preferable, and calcium is particularly preferable.
What cross-linked the polymer having a uronic acid residue of the present invention with a polyvalent metal ion is different from a polymer having a uronic acid residue or a monovalent metal ion salt of a polymer having a uronic acid residue, Insoluble in water. In addition, the polymer having a uronic acid residue may exhibit a gel form when it is simply crosslinked with a polyvalent metal ion. However, in the present invention, in order to broaden the range of application to food and drink, Is preferred.

The flavonoid used in the present invention is a kind of polyphenols contained in most plants that perform photosynthesis. Flavonoids can be further classified into flavones, flavonols, isoflavones, anthocyanidins, flavanones, and catechins, and one or more selected from the group containing these derivatives and polymers can be used. Either natural or synthetic can be used, but natural plant extracts are preferred.
The plant that is the raw material of the flavonoid is not particularly limited, but for example, camellia plants such as tea, grape plants such as grapes, akabanae plants such as coffee, aegiriaceae plants such as cacao, and seeds such as buckwheat. Plant, gooseberry, blackcurrant, redcurrant, etc., blueberry, howlberry, black hackleberry, cranberry, cowberry, etc., Gramineae such as red rice, purple maize, mulberry, etc. Plants, honeysuckle plants such as elderberry, black-bellied plum, plum, european blackberry, loganberry, salmonberry, ezostrawberry, strawberry strawberry, blueberry strawberry, Dutch strawberry, blackberry strawberry, morero cherry, Yoshino cherry, cherry tree cherry,甜, Roses such as apples, enjus, red beans, soybeans, tamarind, mimosa, peguasenyaku and other legumes, purple yams and other yamaceous plants, oysters and other oysters, umbilicals and spring chrysanthemum and other asteraceae plants and bananas And other species such as Bacilliaceae plants, Convolvulaceae plants such as Yamakawamurarasaki, Aoiaceae plants such as Roselle, Lamiaceae plants such as red perilla, and Brassicaceae plants such as red cabbage, etc. according to these plants Sites such as pericarp, flowers, leaves, stems, bark, roots, tuberous roots, seeds and seed coats are arbitrarily selected.

Flavonoids can be extracted from these plants with a solvent such as hot water, ethyl acetate, methanol, ethanol, isopropanol.
Among these, flavonoids obtained by extraction from grape seeds that are grape plants or tea leaves that are camellias are preferable. Specific substance names of these flavonoids include anthocyanidin, delphinidin, catechin, gallocatechin, gallocatechin gallate, epicatechin, epicatechin gallate, epigallocatechin, epigallocatechin gallate, theaflavin, etc., one kind selected from these Or the mixture of 2 or more types is mentioned.
Moreover, it does not specifically limit about the purity of the flavonoid in an extract, Preferably it is 40% or more, More preferably, it is 60% or more.
The flavonoid extract is preferably in the form of a solid or powder that is insoluble in fats and oils.
Gravinol (Kikkoman Co., Ltd.), Sun Flavon (Taiyo Kagaku Co., Ltd.), Tea Franc (Itoen Co., Ltd.), San Oolong (Suntory Co., Ltd.), Polyphenon (Tokyo Food Techno Co., Ltd.), etc. Other flavonoid-containing materials can also be used.

A method for obtaining a flavonoid composition containing a flavonoid coated with a polymer having a uronic acid residue according to the present invention is not particularly limited, and includes, for example, a polymer having a uronic acid residue and a flavonoid. It can be obtained by spray drying an aqueous solution.
At that time, after the flavonoid was made into a dispersion-in-oil composition by a method of performing oil coating in the presence of a polyhydric alcohol fatty acid ester, as disclosed in Japanese Patent Application Laid-Open No. 2002-29968 previously filed by the present applicant. Further, polyhydric alcohol fatty acid esters which are made into a W / O / W dispersion can be used. In this case, the flavonoid is preferably a fine powder as described in the prior patent application. Also, polyhydric alcohol fatty acid esters and fats and oils may be those shown in the prior application patent.
It is preferable to coat this flavonoid W / O / W dispersed with a polymer having a uronic acid residue, because it is less likely to taste.

Further, the coating method in the case of coating a polymer having a uronic acid residue with a polymer crosslinked with a polyvalent metal ion is not particularly limited. The coated flavonoid is put into a fluid granulator and fluidized while spraying an aqueous solution containing a polyvalent metal ion while sending warm air, and the polymer having the uronic acid residue on the powder surface is converted to a polyvalent metal ion. It can be obtained by crosslinking. Alternatively, an aqueous solution containing a polymer having a uronic acid residue and a flavonoid can be obtained by making fine particles by a spray drying method, an emulsion method, or the like and then immersing it in an aqueous solution containing a polyvalent metal ion. In addition, an aqueous solution containing a polymer having a uronic acid residue and a flavonoid may be stirred in an aqueous solution containing a polyvalent metal ion, and then insoluble matter may be collected, dried and pulverized to form a granular material.
Further, it is more preferable that the flavonoid is W / O / W dispersed as described above.

  The ratio of the polymer having a uronic acid residue and the flavonoid in the present invention is not particularly limited, but the polymer having a uronic acid residue is preferably 1 to 100 parts by weight with respect to 100 parts by weight of the flavonoid. More preferably, it is 10 to 80 parts by weight, and most preferably 30 to 60 parts by weight. When it is less than this range, the effect of improving the taste by coating is weak, and there is a problem that the taste of flavonoids may appear. On the other hand, when the amount is larger than this range, the amount of the flavonoid which is the main component in the flavonoid composition is reduced, the effect as a flavonoid is lowered, and the composition must be used in a large amount.

  The content of the flavonoid in the flavonoid composition is not particularly limited, but is preferably 1 to 70% by weight, more preferably 2 to 60% by weight, and still more preferably 5 to 50% by weight. is there. When the amount is less than this range, the amount of the flavonoid that is the main agent becomes a trace amount, the effect as a flavonoid is reduced, and there is a problem that a large amount of the composition must be used. In addition, when the amount is larger than this range, the structural viscosity becomes extremely high and the fluidity is lost, so that it is difficult to produce the composition or the subsequent processing characteristics are remarkably narrowed. There is.

The flavonoid composition of the present invention can be applied to various foods and drinks, feeds, pet foods and the like.
The food and drink in the present invention is not particularly limited as long as it is a form that can be taken orally, such as a solution, suspension, powder, or solid molded product. More specifically, instant noodles, retort foods, canned foods, microwave foods, instant soups and miso soups, freeze-dried foods, soft drinks, fruit juice drinks, vegetable drinks, soy milk drinks, coffee drinks, tea drinks Beverages such as powdered beverages, concentrated beverages, nutritional beverages, alcoholic beverages, bread, pasta, noodles, cake mixes, flour products such as fried flour, bread crumbs, rice cakes, caramel, chewing gum, chocolate, cookies, biscuits, cakes, Sweets such as pies, snacks, crackers, Japanese sweets, desserts, sauces, processed tomato seasonings, flavor seasonings, cooking mixes, sauces, dressings, soups, curry and stew seasonings, processing Fats and oils such as butter, margarine and mayonnaise, milk beverages, yogurts, lactic acid bacteria beverages, ice creams, chestnuts Agricultural processing of dairy products such as mussels, frozen foods, processed fishery products such as fish ham and sausages, marine products, processed livestock products such as livestock ham and sausages, canned agricultural products, jams and marmalades, pickles, boiled beans and cereals Products, nutritional foods, liquid foods, oral and tube feedings, baby foods, tablets, capsules and the like.
When processing the flavonoid composition of the present invention into various foods, feeds, pet foods, etc., it may be sterilized. Examples of sterilization include atmospheric steam sterilization, superheated steam sterilization, UHT sterilization, microwave sterilization, retort sterilization, boil sterilization, gas sterilization, electric current sterilization, and radiation sterilization.

When processing the flavonoid composition of the present invention into various foods, feeds, pet foods and the like, various nutritional components and the like can be added. Nutritional components include proteins, peptides, amino acids, lipids, surfactants, saccharides, sugar alcohols, polysaccharides, vitamin A, vitamin B ₁ , vitamin B ₂ , vitamin B ₆ , vitamin B ₁₂ , vitamin C, vitamin D Vitamin E, vitamins such as niacin (nicotinic acid), pantothenic acid, folic acid, essential amino acids such as lysine, threonine, tryptophan, minerals such as calcium, magnesium, iron, zinc, copper and, for example, α- As substances contributing to human health, such as linolenic acid, EPA, DHA, evening primrose oil, octacosanol, casein phosphopeptide (CPP), calcium calcium casein (CCP), dietary fiber, oligosaccharides, and other foods and food additives One or more of the approved useful substances can be used.
When using the flavonoid composition of the present invention as a deodorant food, for the purpose of enhancing the intestinal regulation and deodorizing effect, galactooligosaccharide, fructooligosaccharide, soybean oligosaccharide, xylooligosaccharide, dairy oligosaccharide, raffinose, lactulose, Indigestible oligosaccharides such as palatinose oligosaccharide, nigerooligosaccharide, gentio-oligosaccharide, polydextrose, indigestible dextrin, guar gum enzyme degradation product, psyllium seed coat, glucomannan, agar, water-soluble soybean polysaccharide, water-soluble corn fiber, etc. Intestinal benign bacteria such as dietary fiber, bifidobacteria and lactic acid bacteria, green tea extract, oolong tea extract, mushroom extract, persimmon extract (persimmon astringent), apple extract, wormwood extract, leaves of celery family such as carrot and parsley You may add 1 type, or 2 or more types chosen from a dried material, a spinach extract, etc.

Examples and test examples are given below to specifically show the effects of the present invention, but the present invention is not limited to these examples.
Example 1
Grape seed extract (Gravinol super, proanthocyanidin content 95%, manufactured by Kikkoman Corporation) 100 g and pectin (Neosoft P, Taiyo Chemical Co., Ltd.) 40 g were mixed in 400 g of water and dissolved by heating. The solution was freeze-dried and then pulverized to obtain 138 g of a grape seed extract coated with pectin. (Invention product 1)

Example 2
Heating and melting 48 g of coconut oil (melting point 36 ° C.), mixing 2 g of polyglycerin condensed ricinoleic acid ester (Sunsoft 818DG, manufactured by Taiyo Kagaku Co., Ltd.) and keeping the temperature at 65 ° C. to 70 ° C. in a hot water bath, 40 g of grape seed extract (Gravinol super, proanthocyanidin content 95%, manufactured by Kikkoman Corporation) was added to prepare an oily suspension. This oily suspension was applied to a dyno mill (manufactured by Shinmaru Enterprises Co., Ltd.), and when the average particle size of the grape seed extract became 0.8 μm by laser diffraction type particle size distribution measurement, 10 g of glycerin fatty acid ester (Sunfat PS-68, manufactured by Taiyo Kagaku Co., Ltd.) was mixed to obtain a fine particle dispersion of grape seed extract.
Next, 10 g of pectin (Neosoft P, Taiyo Kagaku Co., Ltd.) is mixed with 400 g of water, 0.5 g of glycerin fatty acid organic acid ester (Sunsoft 621B, Taiyo Kagaku Co., Ltd.), polyglycerin fatty acid ester (Sunsoft Q) -82S (manufactured by Taiyo Kagaku Co., Ltd.) 0.7 g in sequence, dissolved by heating, and while stirring at a homomixer while maintaining 55-65 ° C., dextrin (BLD, manufactured by Sanmatsu Kogyo Co., Ltd.) 8 g and 60 g of the above-obtained grape seed extract finely-divided dispersion obtained by heating were gradually added and emulsified, followed by spray drying and 90 g of grape seed extract coated with pectin. Obtained. (Invention product 2)

Example 3
90 g of grape seed extract coated with pectin obtained in Example 1 was put into a fluid granulator, and while flowing hot air, it was fluidized while spraying 10 g of a 20 wt% calcium chloride aqueous solution. Was subjected to calcium ion cross-linking to obtain 90 g of grape seed extract coated with a calcium cross-linked product of pectin. (Invention product 3)

Example 4
90 g of grape seed extract coated with a calcium cross-linked product of pectin was obtained in the same manner as in Example 3 except that the grape seed extract coated with pectin obtained in Example 2 was used. (Invention product 4)

Example 5
90 g of grape seed extract coated with alginic acid was obtained in the same manner as in Example 2 except that sodium alginate (Kimika Algin, manufactured by Kimika Co., Ltd.) was used instead of pectin as a polymer having a uronic acid residue. (Invention product 5)
Further, in the same manner as in Example 3, 90 g of a grape seed extract coated with calcium alginate was obtained. (Invention product 6)

Example 6
90 g of green tea extract coated with pectin in the same manner as in Example 2 except that green tea extract (Sunflavone HG, flavonoid content 80%, Taiyo Kagaku Co., Ltd.) is used as a flavonoid instead of grape seed extract. Got. (Invention product 7)
In the same manner as in Example 3, 90 g of a green tea extract coated with a calcium cross-linked product of pectin was obtained. (Invention product 8)

Example 7
As a flavonoid, green tea extract (Sunflavone HG, flavonoid content 80%, manufactured by Taiyo Kagaku Co., Ltd.) is used instead of grape seed extract, and as a polymer having uronic acid residues, sodium alginate (Kimika arginine) instead of pectin is used. 90 g of green tea extract coated with sodium alginate was obtained in the same manner as in Example 2 except that Kimika Co., Ltd.) was used. (Invention 9)
Further, in the same manner as in Example 3, 90 g of a green tea extract coated with calcium alginate was obtained. (Invention product 10)

Example 8
50 g of green tea extract (Sunflavone HG, flavonoid content 80%, manufactured by Taiyo Kagaku Co., Ltd.) is dissolved in 500 g of water, 50 g of calcium alginate beads (Flavica Fine S, manufactured by Nisshinbo Co., Ltd.) are added and stirred, and then sprayed. Drying yielded 90 g of green tea extract coated with calcium alginate. (Invention product 11)

Comparative Example 1
In Example 1, 138 g of grape seed extract composition was obtained in the same manner except that dextrin (BLD, manufactured by Sanmatsu Kogyo Co., Ltd.) was used instead of pectin. (Comparative product 1)

Comparative Example 2
In Example 2, 90 g of grape seed extract coated with a polyhydric alcohol fatty acid ester and oil was obtained in the same manner except that dextrin (BLD, manufactured by Sanmatsu Kogyo Co., Ltd.) was used instead of pectin. (Comparative product 2)

Test example 1
About the invention product of the present invention and the comparative product obtained above, astringency is 0 points; no astringency is felt, 1 point; a slight astringency is felt, 2 points; astringency is felt, 3 points; strong astringency 4 points; an extremely strong astringency was evaluated in 5 stages, and the average score of sensory test by 10 panelists was obtained.
The evaluation method is as follows: (1) The sample is directly contained in the mouth, (2) 5% by weight aqueous solution of the sample, (3) 0.5% by weight citric acid is added to the 5% by weight aqueous solution of the sample and heated at 80 ° C. for 30 minutes. The taste was evaluated for each of the three aqueous solutions cooled to room temperature.
The results are shown in Table 1.

  From these results, it was found that the astringent taste of the present invention product was reduced, and even when heated under acidic conditions, the astringency did not appear.

Test example 2
The bioabsorbability of the product of the present invention was tested according to the method of Nakagawa et al. (J. Agric. Food Chemi., 1999, 47, 3967-3933). That is, for 10 healthy men (non-smokers aged 23 to 48 years old), 12 hours before administration of the flavonoid composition, after refusing to eat and drink containing tea and tea-derived ingredients, The green tea extract coated with calcium alginate obtained in Example 7 (product 9 of the present invention) was used as a control product for the remaining half of the five people, and the total catechin content 254 mg ( Orally ingested so that the epigallocatechin gallate content was 82 mg). Blood was collected immediately before oral ingestion and 1 hour after ingestion, and after separating the serum, the epigallocatechin gallate content in the serum was measured. Table 2 shows the epigallocatechin gallate content in serum.

  From this result, it was found that the product of the present invention has in vivo absorbability equivalent to that of the raw material.

Test example 3
Regarding the deodorizing effect of feces, 7 adult males (35 to 45 years old) are grouped, (a) the invention product 2 obtained in Example 2 is used as the group, and (b) group is the raw material. A capsule filled with grape seed extract in a hard capsule was taken each morning for 400 mg in terms of proanthocyanidins for 14 days, and the stool on the day before the internal use, the internal use, the 7th day, and the 14th day was subjected to an odor sensory test. The odor sensory test is the following: 0 points; no odor, 1 point; slightly odor, 2 points; moderate odor, 3 points; very odor Evaluation was made in 5 stages, and the average score of sensory test by 5 panelists was obtained.
The results are shown in Table 3.

  From this result, it was found that the present invention product has a fecal deodorizing effect equivalent to that of the raw material.

Example 9
A flavonoid-added yogurt was prepared by adding 5 g of grape seed extract (product 3 of the present invention) coated with a calcium cross-linked product of pectin obtained in Example 3 to 95 g of commercially available plain yogurt.
The astringent taste of the raw grape seed extract was not felt in this yogurt.

Example 10
6 g of the green tea extract coated with calcium alginate obtained in Example 7 (Product 9 of the present invention) was added to 200 g of a commercially available cake premix and baked at 160 ° C. for 30 minutes according to a conventional method to obtain a pound cake. Prepared.
The astringent taste of the raw green tea extract was not felt in the present pound cake.

  The flavonoid composition characterized by containing a flavonoid coated with a polymer having a uronic acid residue obtained in the present invention has a reduced flavonoid astringency, and is heated by heating under acidic conditions. It turned out that the effect was not lost. Furthermore, since the in vivo absorbability and fecal deodorizing effect of flavonoids are not impaired, they can be applied to various foods and drinks while leaving the physiological functions of flavonoids.

Claims (3)

A flavonoid composition comprising a flavonoid coated with a polymer having a uronic acid residue. The flavonoid composition according to claim 1, wherein the polymer having a uronic acid residue contains a polyvalent metal ion. A food or drink comprising the flavonoid composition according to claim 1 or 2.