JP2018052856A - Arginine supply agent - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide arginine that does not exhibit a bitter or fishy smell suitable for eating and drinking.SOLUTION: An arginine supply agent that does not exhibit a bitter or fishy smell comprising a proteoglycan arginine body obtained by bringing proteoglycan and arginine into contact in an aqueous solution has a dry weight arginine content of at least 20 mass% and absorption peaks in an infrared absorption spectrum measured by the KBr disk transmission method at all the following wave numbers: 1652±10 cm; 1455±10 cm; 1412±10 cm; 1317±10 cm; 1226±10 cm; 1065±10 cm; and 930±10 cm.SELECTED DRAWING: Figure 1

Description

  The present invention relates to a substance containing arginine that does not exhibit bitterness and raw odor.

  Arginine is one of the amino acids that make up protein, and is abundant in meat, seafood, soybeans and the like. Arginine is a non-essential amino acid, but it promotes the secretion of hormones such as growth hormone and insulin, and through the secretion of hormones, the immune system is activated, wound healing is promoted, and the release of nitric oxide, which is involved in vascular relaxation. Involved in important functions in the body, such as the role of Arginine has been widely used as a health supplement since it has been said to recover from fatigue and enhances energy, and if it is deficient, it can cause poor growth.

  Many health supplements take the form of beverages that are easy to ingest, but arginine has a bitter taste and a peculiar odor, which has a problem in palatability. Therefore, there is a method (Patent Document 1) in which one or more amino acids other than L-ascorbic acid, alcohol, and lysine, proline, phenylalanine, histidine, and methionine are included, but it is applicable to non-alcoholic beverages. There are disadvantages that cannot be done and there are limitations on the amino acids to be contained. There is also a method of adding citrus oil (Patent Document 2), but there is a drawback that the flavor is limited to citrus. There is also a method using vitamin B1 and carbonic acid (Patent Document 3), but it is limited to carbonated beverages, vitamin B1 is easily decomposed by alkali, and is unstable to heat when the pH exceeds 5. There are drawbacks such as decomposition is easily promoted by metal ions.

JP 2007-43941 A JP 2007-116939 A JP, 2006-10339, A

  In view of the above problems, an object of the present invention is to provide a novel arginine supply agent that does not exhibit the bitterness and raw odor characteristic of arginine.

In order to achieve the above object, the inventors have found that the following proteoglycan arginine bodies are excellent substances. The proteoglycan arginine obtained by contacting proteoglycan and arginine in an aqueous solution contains 20% by weight or more of arginine per dry weight, and in the infrared absorption spectrum measured by the KBr disk transmission method, wave number 1652 ± 10 cm ⁻¹ , 1455 ± 10 cm ⁻¹ , 1412 ± 10 cm ⁻¹ , 1317 ± 10 cm ⁻¹ , 1226 ± 10 cm ⁻¹ , 1065 ± 10 cm ⁻¹ , 930 ± 10 cm ⁻¹ all have absorption peaks, and 1065 ± the ratio of the absorbance of 1652 ± 10 cm ^-1 to the absorbance of 10 cm ^-1 is 1.5 or more, 1412 ratio of 1065 absorbance ± 10 cm ^-1 to the absorbance of ± 10 cm ^-1 is within 2, to the absorbance of 1412 ± 10 cm ^-1 1226 absorption of ± 10cm ^-1 The ratio of is a proteoglycan arginine of less than 1.2.

  According to the present invention, it is possible to provide arginine that does not exhibit the bitterness and odor characteristic of arginine.

It is a figure showing the infrared absorption spectrum measured by the KBr disk transmission method of the proteoglycan arginine body obtained in Example 1 in connection with the analysis of the proteoglycan arginine body of Example 2 of the present invention. It is a figure showing the infrared absorption spectrum measured by the KBr disk transmission method of the proteoglycan which is a raw material of a comparative example in connection with the analysis of the comparative proteoglycan arginine body of Example 2.

  Hereinafter, the embodiment will be described more specifically.

Arginine in the present invention is an amino acid having a molecular weight of 174.2 represented by a chemical formula of C ₆ H ₁₄ N ₄ O ₂ . The CAS registration number of L-arginine is 74-79-3, and the present invention also covers D-arginine (CAS registration number 157-06-2). The proteoglycan referred to in the present invention is a high molecular compound having a molecular weight of several hundred thousand to several million consisting of a covalently bonded product of glycosaminoglycan and protein present in animals and fish. The proteoglycan referred to in the present invention is the origin, although the molecular weight and the types, amounts, and ratios of amino acids and sugars (neutral sugars, uronic acids, amino sugars, etc.) differ depending on the starting materials and extraction / production conditions. Regardless of the raw material and extraction / manufacturing conditions.

The proteoglycan arginine body of the present invention is a proteoglycan arginine body obtained by contacting proteoglycan and arginine in an aqueous solution, wherein arginine is bound to anions such as carboxylic acid and sulfuric acid in the proteoglycan molecule. It is. The content of arginine is 20% by weight or more based on the dry weight of the proteoglycan arginine body. In the infrared absorption spectrum measured by the KBr disk transmission method, the wave numbers are 1652 ± 10 cm ⁻¹ , 1455 ± 10 cm ^{− 1} , 1412 ± 10 cm ⁻¹ , 1317 ± 10 cm ⁻¹ , 1226 ± 10 cm ⁻¹ , 1065 ± 10 cm ⁻¹ , 930 ± 10 cm ⁻¹ all have absorption peaks and 1652 ± for an absorbance of 1065 ± 10 cm ⁻¹ the ratio of the absorbance of 10 cm ^-1 is 1.5 or more, 1412 ratio of 1065 absorbance ± 10 cm ^-1 to the absorbance of ± 10 cm ^-1 is within 2, of 1226 absorbance ± 10 cm ^-1 to the absorbance of 1412 ± 10 cm ^-1 It is a proteoglycan arginine body with a ratio within 1.2. The absorbance can be calculated from the transmittance by a conventional chemical calculation method. There are various methods for measuring the amount of arginine, such as the ninhydrin method, the Sakaguchi method, the amino acid analysis instrument method, the refractometer by high performance liquid chromatography, and the ultraviolet spectroscopy method. If no other amino acids are present, the ninhydrin method is used. The method is simple.

  In one of the methods for producing a proteoglycan arginine product of the present invention, first, a raw material proteoglycan is brought into contact with a proton-type strongly acidic cation exchange resin. The strongly acidic cation exchange resin is a water-insoluble polymer resin in which a sulfonic acid group ion exchange group is introduced into a carrier. Examples of the carrier include synthetic resins such as styrene, phenol, vinyl, and acrylamide, cellulose, agarose, and dextran. Before using the resin, it is necessary to preliminarily wash it with acid or alkali by a conventional method, and to activate it into proton type with hydrochloric acid or the like. Regarding the amount of strongly acidic cation exchange resin relative to the amount of proteoglycan to be treated, the amount of inorganic ions bound to proteoglycan is greater than the ion exchange capacity of strongly acidic cation exchange resin multiplied by a safety factor. The amount is desired and the contact time with the strongly acidic cation exchange resin should be several minutes or longer. Next, the proteoglycan brought into contact with the strongly acidic cation exchange resin is separated from the resin by a method such as filtration. When the filtered strong acid cation exchange resin is washed with water, the recovery efficiency is good. As another production method, the raw material proteoglycan may be treated with an inorganic acid, citric acid, trifluoroacetic acid, or the like at a low temperature of 15 ° C. or lower to remove the used acid or free low molecules. As the inorganic acid, hydrochloric acid or sulfuric acid of 1M or less is used.

  Next, arginine is added to and brought into contact with the solution containing this proton type proteoglycan, but arginine is required to be 0.5 times or more in weight ratio with respect to 1 weight of proteoglycan. When the solution is stirred or shaken, the production efficiency is good. Arginine can be added or contacted either in solid form or in an aqueous solution. The contact temperature is in the range of 1 ° C. to 60 ° C. and requires several hours or more. Then, after removing excess arginine that is not bound to proteoglycan by dialysis or membrane treatment usually used in chemistry, it may be solidified and powdered. In addition to dialysis and membrane treatment, alcohol, acetone, etc. The proteoglycan arginine body may be precipitated and air-dried with an organic solvent, and powdered. The obtained proteoglycan arginine body is a substance having a high content of arginine that does not exhibit bitterness and odor.

  The product of the present invention may be taken alone or in combination with other health aid ingredients in the form of a powder, or may be in the form of tablets or capsules. Moreover, you may use together with other health supplement components etc. individually as a form of a drink or a drink agent in the state of a solution.

  The present invention will be specifically described below with reference to examples. However, the present invention is described for illustrative purposes only, and the present invention is not limited to these examples.

(Production of proteoglycan arginine)
A strongly acidic cation exchange resin (trade name: Diaion SK1B (Mitsubishi Chemical Corporation)) is packed in a glass column (inner diameter 2.7 cm, height 5 cm), and 1 mL hydrochloric acid 70 mL is flowed down, and the resin is protonated. Activated. After the resin was washed by flowing down 350 mL of deionized water, a solution of 0.10 g of the raw material proteoglycan (Kadohiro Proteoglycan Laboratory) in 10 mL of deionized water was added and allowed to flow down from above the column at room temperature. Thereafter, 90 mL of deionized water was passed through the resin to obtain about 100 mL of an eluate containing proton type proteoglycan. To this eluate, 0.05 g of L-arginine (Wako Pure Chemical Industries, Ltd.) was added and stirred overnight at 4 ° C. It was 6.5 when pH of the solution was measured with a desktop pH meter (F-55, manufactured by Horiba, Ltd.). Next, the entire amount of the solution was put in a cellulose tube for dialysis (Edia Co., Ltd.), both ends of the tube were clipped, and dialyzed using deionized water as an external solution to remove excess arginine. The external liquid was changed three times a day. Three days later, the solution in the cellulose tube for dialysis was collected, concentrated with a rotary evaporator (Tokyo Science Instrument Co., Ltd.), freeze-dried (Tokyo Science Instrument Co., Ltd.), and 0.14 g of a white flocculent solid. Proteoglycan arginine body was obtained.

(Analysis of proteoglycan arginine)
The water content of the proteoglycan arginine body obtained in Example 1 was heated with a thermobalance (Thermo Plus TG8210, manufactured by Rigaku Corporation) at 125 ° C. until the sample weight reached a constant weight, and the weight loss was sampled. Moisture contained in the water. As a result, the water content of the proteoglycan arginine compound obtained in Example 1 was 9.6% by weight.

  The content of arginine in the proteoglycan arginine obtained in Example 1 was determined from a calibration curve using L-arginine (Wako Pure Chemical Industries, Ltd.) as a standard substance by the ninhydrin method which is a colorimetric method. It was 23.6% by weight per dry weight.

The infrared absorption spectrum of the proteoglycan arginine obtained in Example 1 was measured by the KBr disk transmission method. Infrared absorption spectrum, a Fourier transform infrared spectrophotometer using (FT / IR-420, manufactured by JASCO Corporation), measurement range 4000 to 400 ^-1, resolution ^{4 cm -1,} in terms of number of integration 54 It was measured. FIG. 1 is an infrared absorption spectrum of the proteoglycan arginine obtained in Example 1. The horizontal axis of the graph in FIG. 1 represents the wave number (cm ⁻¹ ), and the vertical axis represents the transmittance (%). In FIG. 1, the part which becomes a trough is an absorption peak, and the numbers 1-7 described in the absorption peak show the characteristic peak of a proteoglycan arginine body. Peak 1 has a wave number of 1652 cm ⁻¹ and a transmittance of 15.3% (= absorbance 0.815), Peak 2 has a wave number of 1455 cm ⁻¹ and a transmittance of 71.5% (= absorbance 0.146), and Peak 3 has a wave number of 1412 cm ^{− 1} has a transmittance of 54.3% (= absorbance 0.265), peak 4 has a wave number of 1317 cm ⁻¹ and a transmittance of 81.7% (= absorbance 0.082), peak 5 has a wave number of 1226 cm ⁻¹ and a transmittance of 55.55. 5% (= absorbance 0.256), peak 6 is wavenumber 1065 cm ⁻¹ and transmittance 38.9% (= absorbance 0.410), peak 7 is 930 cm ⁻¹ and transmittance 93.0% (= absorbance 0. 0). 032). The ratio of absorbance at 1226cm ^-1 ratio of absorbance at 1065 cm ^-1 absorbance ratio of 1652 ^-1 to the absorbance at a wavenumber of 1065 cm ^-1 is for the absorbance of 2.0,1412Cm ^-1 it is for the absorbance of 1.5,1412Cm ^-1 1.0. As a comparative example, the infrared absorption spectrum of the raw material proteoglycan was similarly measured by the KBr disk transmission method. FIG. 2 shows the results, where the valley portion is an absorption peak, the number 1 described in the absorption peak is a proteoglycan characteristic peak, and the numbers 2 to 4 are characteristic features approximate to the proteoglycan arginine body. Shows the peak. Peak 1 has a wave number of 1639 cm ⁻¹ and a transmittance of 16.0% (= absorbance 0.796), Peak 2 has a wave number of 1421 cm ⁻¹ and a transmittance of 49.6% (= absorbance 0.305), and Peak 3 has a wave number of 1231 cm ^{−. 1} had a transmittance of 34.7% (= absorbance 0.460), and peak 4 had a wave number of 1067 cm ⁻¹ and a transmittance of 17.6% (= absorbance 0.754). The ratio of absorbance at 1067cm ^-1 to the absorbance at a wavenumber of 1421cm ^-1 is the ratio of the absorbance at 1231cm ^-1 to the absorbance of 2.5,1421Cm ^-1 it was 1.5.

(Sensory test of proteoglycan arginine)
Next, the same treatment as in Example 1 was performed to prepare a proteoglycan arginine body. That is, 0.3 g of a raw material proteoglycan (Kadohiro Proteoglycan Research Institute) was treated with a proton type strongly acidic cation exchange resin (trade name: Diaion SK1B (Mitsubishi Chemical Corporation)), -0.15g of arginine (Wako Pure Chemical Industries, Ltd.) was added, and it stirred at 4 degreeC overnight. Next, this solution is dialyzed against deionized water as an external solution to remove excess arginine, concentrated on a rotary evaporator (Tokyo Science Instruments Co., Ltd.), and then freeze-dried (Tokyo Science Instruments Co., Ltd.). 0.41 g of a white flocculent solid proteoglycan arginine was obtained.

  When five males and females in their twenties or more as test subjects had 5 mL of L-arginine (Wako Pure Chemical Industries, Ltd.) aqueous solution dissolved in deionized water at 0.3 w / v% in their mouths, all five people Declared that he felt bitter and raw. Next, the same 5 proteoglycan arginines prepared above were dissolved in deionized water at 1.3 w / v% (concentration as arginine: 0.3 w / v%), and 5 mL was included in the mouth. As a result, all five people reported that they did not feel bitter and odors.

  By providing arginine that does not exhibit bitterness and raw odor according to the present invention, it can be widely used in foods, particularly in the health food industry.

Claims (1)

The proteoglycan arginine obtained by contacting proteoglycan and arginine in an aqueous solution contains 20% by weight or more of arginine per dry weight, and in the infrared absorption spectrum measured by the KBr disk transmission method, wave number 1652 ± 10 cm ^{− 1} , 1455 ± 10 cm ⁻¹ , 1412 ± 10 cm ⁻¹ , 1317 ± 10 cm ⁻¹ , 1226 ± 10 cm ⁻¹ , 1065 ± 10 cm ⁻¹ , 930 ± 10 cm ⁻¹ all have absorption peaks, and 1065 ± 10 cm ⁻ 1652 the ratio of the absorbance of ± 10 cm ^-1 is 1.5 or more with respect to ¹ absorbance, 1412 1065 ratio of absorbance at ± 10 cm ^-1 is within 2 to the absorbance of ± 10 cm ^-1, 1226 ± to the absorbance of 1412 ± 10 cm ^-1 the ratio of the absorbance of 10cm ^-1 It is within .2, proteoglycan arginine body.

Images