JPH0424023B2 - - Google Patents

Description

[Detailed description of the invention]

(Industrial Application Field) This invention relates to foods containing specific oligosaccharides, and its purpose is to make foods contain specific oligosaccharides made of methoxyphenyl glucose extracted from natural products or synthesized. According to
The object of the present invention is to provide a food containing methoxyphenylglucose that can exert a glucose absorption suppressing effect and an antiallergic effect on those who consume the food. (Prior art and its problems) The inventors have been conducting research on anti-allergic and anti-arteriosclerotic substances and glucose absorption inhibitory effects for many years. We have already discovered that the black pigment component extracted from raw sugar has both of these effects as a substance that has both a hardening effect and a glucose absorption suppressing effect, and we have published this on various occasions. In particular, the glucose absorption inhibitory effect refers to the effect of suppressing the absorption of glucose in the body, which in turn suppresses increases in neutral fats, insulin, and lipid peroxides in serum. In recent years, there has been a general trend in the diet of both infants and adults to include more sugar and sugar-based foods such as cooked rice, noodles, bread, potatoes, and various sweets. The amount of glucose tends to increase, and as a result, excess glucose is stored in the body as fat, increasing the tendency for obesity in infants, children, and adults alike. In particular, young infants and children are more likely to develop obesity and hyperlipidemia due to excessive glucose intake, as well as diseases derived from hyperlipidemia. hindrance,
It has been medically clarified that it is likely to cause diabetes and heart disease. Especially among young children, the number of so-called obese children has been rapidly increasing over the past 10 years. In addition, when triglycerides and cholesterol increase in the blood due to excessive intake of carbohydrate-based foods, the clay content of the blood rises, causing a phenomenon known as hemoglobin, which reduces the amount of blood flowing into the capillaries, reducing the amount of blood flowing into the peripheral blood vessels. Nutritional supply in the distribution of blood vessels becomes insufficient,
They cause various skin diseases and various indeterminate complaints, and are more likely to develop diseases such as hyperlipidemia and arteriosclerosis. On the other hand, allergic diseases (such as atopic dermatitis, asthma, and other disorders) are frequently observed in young children, although it is still unclear whether this is directly caused by excessive consumption of carbohydrate-based foods and obesity. In particular, in order to suppress the obesity mentioned above, it is originally necessary to improve the diet and change to a low-carbohydrate diet so as not to eat too many high-carbohydrate foods. The fact that eating habits are controlled throughout a child's life by childhood experiences poses a problem in improving the eating habits mentioned above, and even from daily experience, it is quite difficult to improve high-carbohydrate and overeating. The inventors believe that if it is difficult to improve such dietary tendencies, it is possible to suppress glucose absorption in the body while maintaining high carbohydrate dietary tendencies.
Focusing on the fact that it is ineffective in eliminating obese children who tend to develop obesity, which causes such incurable diseases, we continued our research. (Solution Means of the Invention) Therefore, in light of the above viewpoint, the inventors
After extensive research, and after many failures, they discovered a substance that was extremely safe and had an excellent glucose absorption inhibitory effect. This invention was completed by experimentally discovering that this specific oligosaccharide has a remarkable suppressive effect and furthermore, that the above-mentioned anti-allergic effect is contained in this specific oligosaccharide. That is, the present invention solves all of the above-mentioned conventional problems by providing a food containing a specific oligosaccharide consisting of methoxyphenyl glucose. (Structure of the Invention) In the present invention, methoxyphenylglucoses include all structures in which methoxyphenol and glucose are bonded to an ether, and 2,4,5-methoxyphenyl-O- Glucose can exhibit a glucose absorption inhibitory effect that also has an effective anti-allergic effect. (General formula 1) (General formula 2) There are two methods for obtaining the methoxyphenyl glucose used in this invention: a synthetic method and a natural extraction method. First, as a method for obtaining the natural product ruglucose, There are two methods, a synthesis method and a natural product extraction method. When extracting from a natural product, for example, raw sugar (so-called unrefined sucrose) is usually first prepared from sugar cane or sugar beet. Next, this raw sugar is dissolved in an appropriate amount of water and brought into contact with an adsorbent to adsorb the pigment component to the adsorbent.
After washing the adsorbent with water, the sugar content is further sufficiently removed, and then the adsorbed pigment component is eluted with a solvent. Usually, this elution operation is performed by column chromatography packed with an adsorbent. For example, the adsorbent used in this case is a non-polar polystyrene resin adsorbent such as Amberlite XAD-1, Amberlite XAD-2.
(manufactured by Rohm, & Haas) and Selvachrome YAD-2 (manufactured by Selva) are suitable. From the viewpoint of yield, Selvachrome XAD-2 is most preferred. Further, the amount of adsorbent used is suitably 30 to 300 times (by weight) and preferably 50 to 200 times the amount of the pigment component contained. Furthermore, when eluting the adsorbed pigment components, it is preferable to wash with water before elution to sufficiently remove sugar until the washing liquid loses its sweetness. Elution of the dye component is preferably carried out with a lower alcohol having a concentration of 20% or more, such as methanol or ethanol. In practice, it is preferable to first elute with a low concentration lower alcohol of 20 to 30%, until almost no coloring of the flowing liquid is observed, and then further elute with a high concentration lower alcohol of about 95 to 99%. This is because elution using only high-concentration lower alcohols is undesirable because the yield of the dye component decreases. After the eluent thus obtained was evaporated to dryness,
Purification and fractionation using a silica gel column yields the white specific oligosaccharide used in this invention, namely methoxyphenylglucose. The inventors have experimentally learned that this specific oligosaccharide is included in the pigment component of crude sugar as described above, and that this specific oligosaccharide contains methoxyphenyl glucose as an active ingredient. It is becoming clear. Of the specific oligosaccharides thus obtained, methoxyphenylglucose is contained in a weight ratio of 40% or more, and in particular, 2,5-methoxyphenyl-O-glucose is contained in a weight ratio of about 20% or more. ,4,
5-methoxyphenyl-O-glucose is about 10%
Occupies more than a certain amount. The inventors have experimentally learned that the internal action components of this pigment component are mainly methoxyphenylglucose, which accounts for 40% or more, and that specific oligosaccharides in methoxyphenylglucose account for 15% or more.
Although this was carried out using conventional qualitative and quantitative analysis methods such as TLC, NMR, IR, and UV, the structures of some methoxyphenyl glucoses extracted from natural products are still unclear. do. The methoxyphenylglucose used in this invention may be one in which a phenyl group and a glucose group are chemically ether bonded by an organic synthesis method, and the method of synthesis is not particularly limited. In addition, a synthesis in which a 2,5-methoxyphenyl group or a 2,4.5-methoxyphenyl group in which a methoxy group is substituted at the C ₂ and C ₃ positions and, if necessary, at the C ₄ position, and a glucose group is ether bonded. 2,5-methoxyphenyl-O-glucose or 2,4.5-methoxyphenyl-O-
Glucose and mixtures thereof can also be used effectively. Therefore, the methoxyphenylglucose mentioned in the present invention may be any substance having a methoxyphenylglucose core, and therefore the position of the methoxyl group substituted with the phenyl group does not necessarily have to be at the benzene ring C ₂ , C ₅ or C ₂ , C ₄ , C ₅ , or other positions such as C ₄ may be substituted with a methoxyl group alone. In order to produce a food containing the specific oligosaccharide made of methoxyphenyl glucose according to the present invention using such methoxyphenyl glucose, for example, the amount of methoxyphenyl glucose per day for an adult is 5 to 500 mg, preferably 10 to 500 mg. 300mg 2~
It is desirable that the food be in a form that can be taken in three portions. Examples of such foods include white bread, bread, cooked rice, sweets, and powder foods. Manufactured by mixing these foods at the raw material stage,
Alternatively, it may be mixed with seasonings such as butter, jam, sugar, furikake, etc. and added to the staple food for consumption. In other words, the foods containing the specific oligosaccharide consisting of methoxyphenylglucose as used in the present invention include staple foods, snacks, seasonings (soy oil, sauce, sugar, jam, furikake), side dishes,
It can be suitably used in all food forms, whether in soft drinks, luxury foods, or powder forms. (Test Example) Next, the glucose absorption inhibitory effect and antiallergic effect of the food containing the specific oligosaccharide consisting of methoxyphenyl glucose according to the present invention will be specifically clarified using test examples. Test Example 1 5 kg of Okinawan brown sugar was dissolved in 25 kg of water, poured into a column with an inner diameter of 8 cm packed with polystyrene resin (Selbachrome XAD-2.300 g) dispersed in 1 part of water, and allowed to flow down at a rate of 20 ml/min. Adsorbs the pigment components of brown sugar. Next, rinse under running water until the sweetness disappears to thoroughly remove sugar. After the flowing liquid no longer has any sweet taste, 20% methanol is injected and allowed to flow down at a rate of 10 ml/min to elute the dye from the adsorbent. When there is almost no coloration in the flowing liquid, change the eluent to 95% methanol.
Continue flowing down until the flowing liquid is completely free of color.
The two eluents were combined and evaporated to dryness under reduced pressure below 60°C to obtain 16 g of a brown residue. This material was heated and dissolved in pure ethanol (2), and after cooling, the precipitated cloudy substance was filtered out, and evaporated to dryness under reduced pressure at 60°C or less.
The residue is dried at below 60°C to obtain 15 g of brown powder with no sweet taste. The active ingredient in the obtained brown powder was methoxyphenyl glucose based on the following Rf value of thin layer chromatography and absorption value of infrared absorption spectrum. Thin layer chromatography: When 10 mg is dissolved in 1 ml of water and tested according to the Japanese Pharmacopoeia General Tests Section 26 Thin Layer Chromatography under the following conditions, a single red spot appears at an Rf value of approximately 0.6. Amount of sample attached: 10μ Support: Silica gel 60F254 (manufactured by Merck, thickness:
0.25mm) Developing solvent: Chloroform/methanol/water (65:35:10) Lower layer Developing distance: 10cm Detection: 105 after spraying P-anisaldehyde test solution
Heated at ℃ for 5 minutes Infrared absorption spectrum: vmax (Nujiol): 3300, 1590, 1020, 720
cm ^-1 The obtained brown powder was dissolved in 500 c.c. methanol,
The mixture was purified by column chromatography using a silica gel column using a flowing solution of chloroform, methanol, and water to obtain white crystals of a mixture of 2,5-methoxyphenylglucose and 2,4,5-methoxyphenylglucose. The following tests were conducted using this sample. Wistar male rats (initial weight 80g, 5 per group)
Three groups (~6 fish) were used, and one group (control group) was fed ad libitum with a high-sucrose diet of the following formulation for 2 months. High sucrose diet prescription (in 100g of feed) Casein 15g sucrose 75g Corn oil 5g Crude salt 4g Vitamin A 1g To this, 300IU of Chiyokola A (vitamin A preparation) and 200mg of choline chloride were added. The other two groups were similarly fed with a high sucrose diet + phenylglucose 1 g/Kg and a high sucrose diet + phenylglucose 0.5 g/Kg, respectively. Ten hours after the final feeding, blood was collected from the rats by decapitation, and serum triglycerides (TG), lipid peroxides (LPO), glucose, and insulin were quantified using standard methods. The results are shown in Table 1.

[Table] Test Example 2 NT 7 years old male kindergarten student Height 120cm Weight 37Kg Name of disease: Atopic dermatitis Current history: I had bronchial asthma from 3 years ago, which was treated for other causes and was mostly relieved, but since 1 year ago my whole body She developed erythematous eczema on her skin. She was diagnosed with atopic dermatitis and received various treatments, but it was not cured, and the dermatitis worsened when she ate sugar-containing sweets. Furthermore, she is obese. Treatment progress: Chinese herbal medicine effective against allergies was administered for one month, but no good results were obtained. Therefore, 300 mg of synthetic 2,5-methoxyphenyl-0-glucose with a purity of 99.99% was ingested per day in powder form. With this method, the erythema began to decrease after one month, and the atopic dermatitis was completely cured after two months. In addition, bronchial asthma attacks were no longer observed at all. Also, after 3 months, the weight was 32 kg. Test Example 3 ST 42-year-old female housewife Height 153cm Weight 68kg Disease name: Indeterminate complaint syndrome (psychosomatic disorder) Current illness: Three miscarriages and one surgery for ectopic pregnancy. Since 15 years ago, she has been suffering from occasional headaches and dizziness, her makeup has become extremely difficult to apply, and her entire face has become sooty red and dark with spots, and she was diagnosed with indeterminate complaint syndrome due to other causes. Furthermore, she is obese. Treatment progress: Synthetic 2,5-methoxyphenyl-0-
Glucose and synthetic 2,4,5-methoxyphenyl-0-glucose (both purity 99.99%)
The subjects were instructed to drink a soft drink containing 200 mg (180 c.c. of soft drink) twice a day (400 mg a day), and their progress was observed. After 3 days, my skin feels moisturized and the bulky skin on my face disappears, and after 2 weeks, my makeup glides on better and no longer feels like it doesn't apply evenly or sparsely like it used to. After several months, the soot on my face disappeared, the redness disappeared, and my complexion became brighter. After three months, the spots on my face started to fade. After 4 months, my weight was 60kg. As is clear from the above results, it can be seen that the food containing the specific oligosaccharide made of methoxyphenyl glucose according to the present invention has excellent glucose absorption inhibiting action and antiallergic action.

Claims (1)

[Scope of Claims] 1. A food containing a specific oligosaccharide consisting of methoxyphenyl glucose. 2 The methoxyphenyl glucose is 2,5-
A food containing the specific oligosaccharide according to claim 1, which is methoxyphenyl-0-glucose. 3 The methoxyphenyl glucose is 2,4,
A food containing the specific oligosaccharide according to claim 1, which is 5-methoxyphenyl-0-glucose. 4 The methoxyphenyl glucose is 2,5-
Methoxyphenyl-0-glucose and 2,4,5
-Methoxyphenyl-0-glucose, the food containing the specific oligosaccharide according to claim 1.