Compositions and methods for preparing and using same

Abstract

The present application provides a composition comprising a wall material and γ-aminobutyric acid, wherein the wall material is one or more selected from the group consisting of β-cyclodextrin and its derivatives, maltodextrin, starch, chitosan, and glucose. The composition of the present application prevents γ-aminobutyric acid from undergoing a Maillard reaction with reducing sugars or carbonyl compounds due to the action of water, and does not produce brown or dark brown polymeric substances, thereby preventing discoloration of the product.

Description

[Technical Field]

[0001] The present application is in the technical field of raw material processing and relates to compositions, methods of preparation and uses. [Background technology]

[0002] Gamma-aminobutyric acid (GABA) is a naturally occurring active amino acid found widely in animals, plants, and microorganisms. It has attracted widespread attention due to its numerous physiological functions, including improving sleep quality, lowering blood pressure, reducing depression and anxiety, slowing aging, and improving brain function. The food safety of GABA is widely recognized in countries such as Japan and the United States, and in 2009, China also approved GABA as a new food ingredient. Research has shown that ingesting a certain amount of GABA from an exogenous source has physiological effects such as improving sleep quality and lowering blood pressure. By adding GABA, a functional factor, to foods to create functional foods, its natural benefits can be fully realized.

[0003] GABA has a strong hygroscopicity, which means that when used in powder formulations, it disperses poorly and is difficult to mix uniformly with other ingredients. In particular, when processing food powder formulations, GABA contains free amino compounds, which easily undergo Maillard reactions with reducing sugars and carbonyl compounds, producing brown or dark brown polymers and changing the color of the product. Summary of the Invention

[0004] The present application provides a composition to solve the problem in the prior art that γ-aminobutyric acid is prone to undergo a Maillard reaction with reducing sugars or carbonyl compounds due to the action of water.

[0005] The technical solution of this application is as follows: 1. A composition comprising a wall material and gamma-aminobutyric acid, the wall material is one or more selected from β-cyclodextrin and its derivatives, maltodextrin, starch, chitosan, and glucose; Preferably, the DE value of the maltodextrin is 5 to 10, and the starch is oxidized starch. composition. 2. The composition comprises a wall material and gamma-aminobutyric acid; Item 1. The composition according to item 1. 3. The mass ratio of the wall material to the γ-aminobutyric acid is (1 to 4):1, preferably (2 to 4):1. Item 1. The composition according to item 1. 4. The wall material comprises β-cyclodextrin and its derivatives, and maltodextrin; Preferably, the mass ratio of the maltodextrin to the β-cyclodextrin and its derivatives is 1:(0.01 to 0.5), preferably 1:(0.2 to 0.3); Item 1. The composition according to item 1. 5. The wall material comprises β-cyclodextrin and its derivatives, and starch; Preferably, the mass ratio of the starch to the β-cyclodextrin and its derivatives is 1:(0.01 to 0.5), preferably 1:(0.2 to 0.3); Item 1. The composition according to item 1. 6. A method for preparing the composition according to any one of items 1 to 5, comprising: Prepare a water solution A of the wall material. Prepare an aqueous solution B of γ-aminobutyric acid. A method for obtaining the composition by mixing an aqueous solution of γ-aminobutyric acid with an aqueous solution of a wall material to obtain aqueous solution C, stirring the mixture, and spray-drying the mixture. 7. In the aqueous solution C, the mass ratio of the total mass of the wall material and the γ-aminobutyric acid to the aqueous solution C is (0.5 to 2.5):10, preferably (1 to 2):10. The method according to item 6. 8. A complex comprising the composition according to any one of items 1 to 5 or a composition prepared by the method according to any one of items 6 to 7. 9. Use of the composition according to any one of items 1 to 5 or the composition prepared by the method according to any one of items 6 to 7 in food and pharmaceutical preparations. 10. Use of the composition according to any one of items 1 to 5 or the composition prepared by the method according to any one of items 6 to 7 in food or pharmaceutical raw materials. 11. Use of the composition according to any one of items 1 to 5 or the composition prepared by the method according to any one of items 6 to 7 for slowing down the Maillard reaction.

[0006] Compared with the prior art, the beneficial effects of the present application are as follows: 1. The composition of the present application prevents gamma-aminobutyric acid from reacting with reducing sugars or carbonyl compounds under the action of water to cause the Maillard reaction, and does not produce brown or dark brown polymeric substances, causing discoloration of the product. 2. The wall material in the composition of the present application can effectively block moisture involved in the browning reaction and effectively protect γ-aminobutyric acid. 3. The wall material in the composition of the present application has strong water absorption properties and can competitively absorb water, slowing down the involvement of moisture in the formulated food in the Maillard reaction of gamma-aminobutyric acid, thereby achieving more significant effects. 4. The present application is simple in operation and easy to control production conditions, which is conducive to industrial production. [Brief explanation of the drawings]

[0007] [Figure 1] Content stability results for several examples. [Figure 2] Maillard reaction color change in some examples. DETAILED DESCRIPTION OF THE INVENTION

[0008] γ-Aminobutyric acid is a white or slightly yellow crystalline powder. It is highly hygroscopic, very soluble in water, slightly soluble in hot ethanol, and insoluble in organic solvents such as benzene, cold ethanol, and ether. It has a slight odor, no optical activity, and is a polar substance. Its melting point is 203-205°C, its relative molecular weight is 103.12, and its molecular formula is CHNO. The dissociation constants of γ-aminobutyric acid are pK = 4.03 and pK = 10.56. γ-Aminobutyric acid usually exists in the form of a zwitterion in aqueous solution, its dissociation is primarily pH-dependent, and its isoelectric point is 7.295. γ-Aminobutyric acid is a non-proteinogenic amino acid with some unique chemical properties. It can undergo hydrocarbylation, acylation, and ninhydrin color reaction.

[0009] γ-aminobutyric acid (γ-ABBA) is attracting increasing attention as a novel food functional factor. Research has shown that γ-ABBA can increase the permeability of neuronal cell membranes to sodium, hyperpolarize the cell membrane, and raise the threshold for initiating action potentials. Therefore, γ-ABBA is an important inhibitory neurotransmitter in the central nervous system of humans and mammals, and is involved in various metabolic activities in the body, possessing potent physiological activities. Its production and application are becoming a hot research area in fields such as food, pharmaceuticals, animal feed, and agriculture. The physiological functions of γ-ABBA are mainly as follows:

[0010] Regulation of cardiovascular function γ-aminobutyric acid (γ-ABBA), an important inhibitory neurotransmitter in the central nervous system, exerts excellent regulatory effects on cardiovascular activity, primarily through regulating heart rate and lowering blood pressure and blood glucose levels. γ-ABBA has a certain pharmacological effect in lowering blood pressure. This is because cerebral blood vessels possess specific neuroreceptors that can bind to γ-ABBA. It is thought that the binding of γ-ABBA to these neuroreceptors can achieve the goal of lowering blood pressure. In experiments, Mao Shikata et al. found that chronic consumption of green tea containing γ-ABBA significantly reduced blood pressure in spontaneously hypertensive rats. Kazami and Inoue K found that the continuous consumption of foods containing γ-ABBA significantly reduced blood pressure in hypertensive patients, but that continued consumption in normotensive individuals did not affect blood pressure, had no effect on other physical indicators, and had no side effects. γ-ABBA can also regulate the vasomotor center by blocking sympathetic nerves, thereby dilating blood vessels and lowering blood pressure. Gamma-aminobutyric acid can lower blood pressure by inhibiting the activity of angiotensin-converting enzyme and vasopressin, an antidiuretic hormone. Gamma-aminobutyric acid can also inhibit the activity of glutamic acid decarboxylase, effectively preventing the decarboxylation of glutamic acid, lowering blood ammonia levels and ensuring human health. Gamma-aminobutyric acid also promotes the binding of glutamic acid and ammonia in the blood to form urea, effectively eliminating ammonia toxins from the body and improving liver and kidney function.

[0011] b. Treatment of epilepsy The number of epilepsy patients in China is reported to be approximately 9 million. The causes of epilepsy are diverse, the underlying mechanism is complex, and it is closely related to central neurotransmitters. Currently, epilepsy is the second most common disease in China, severely affecting people's work and lives. γ-aminobutyric acid (γ-ABBA), an important inhibitory neurotransmitter in the human body, is effective in treating diseases such as epilepsy, insomnia, and Parkinson's syndrome. The central nervous system contains two types of amino acids: excitatory and inhibitory. Excessive excitatory amino acids can reduce neuroinhibitory effects and lead to epilepsy. Numerous studies have shown that γ-ABBA deficiency leads to neuronal hyperexcitability, and that it has specific binding sites in the central nervous system. Binding to these sites increases the permeability of neuronal membranes to Cl, maintaining the cell membrane potential at the resting potential level and weakening synaptic responses to excitatory inputs. Therefore, γ-ABBA can increase the human body's anticonvulsant threshold and effectively treat intractable epilepsy. Okada et al. found that oral intake of rice germ foods containing γ-aminobutyric acid (GAB) can promote sleep, calm nerves, and combat anxiety. It also helps improve symptoms of early psychiatric disorders in elderly people and menopausal symptoms in women. The same study also found that γ-aminobutyric acid content in cerebrospinal fluid (CSF) is negatively correlated with the severity of epilepsy in patients with epilepsy, indicating that low GAB content is associated with epilepsy. Therefore, directly increasing γ-aminobutyric acid content in CSF can be used to treat epilepsy. Research has shown that γ-aminobutyric acid can suppress neural excitation caused by glutamate during severe brain ischemia, thereby reducing neuronal damage. Furthermore, γ-aminobutyric acid is also effective in treating stiff-person syndrome and Parkinson's disease.

[0012] c. Promoting hormone secretion Gamma-aminobutyric acid can regulate the secretion of multiple hormones in the endocrine system, including growth hormone, growth hormone mediators, thyroid hormones, and sex hormones, effectively improving the body's metabolic level. Because gamma-aminobutyric acid directly stimulates the body to secrete necessary hormones, it is safer than directly ingesting exogenous hormones. Research has shown that gamma-aminobutyric acid can regulate the secretion of gonadotropins by suppressing the excitation of certain nerves in the hypothalamus.

[0013] d.Improved liver and kidney function γ-aminobutyric acid inhibits the decarboxylation of glutamic acid, lowering blood ammonia levels. It also has a diuretic effect, excreting excess salt from the body and effectively relieving pressure on the liver and kidneys. Research has shown that γ-aminobutyric acid can activate kidney function. At the same time, γ-aminobutyric acid also inhibits the activity of alkaline phosphatase, and alkaline phosphatase activity is one of the important indicators for evaluating the activation of liver function.

[0014] e. Other features Furthermore, gamma-aminobutyric acid has physiological functions such as preventing obesity, promoting lipid metabolism, preventing vascular sclerosis, repairing skin, and delaying aging. Clinically, gamma-aminobutyric acid can also be used to treat symptoms such as uremia and carbon monoxide poisoning. Gamma-aminobutyric acid also has insecticidal and deodorizing effects.

[0015] Because γ-aminobutyric acid contains a free amino group, when used as a food functional factor, it reacts with reducing sugars and carbonyl compounds in the presence of water, causing the Maillard reaction, which tends to produce brown or dark brown polymeric substances, causing the color of the product to change.

[0016] The present application provides a composition comprising a wall material and γ-aminobutyric acid, wherein the wall material is one or more selected from β-cyclodextrin and its derivatives, maltodextrin, starch, chitosan, and glucose.

[0017] In some embodiments of the present application, the maltodextrin is a maltodextrin with a low DE value, preferably the DE value of the maltodextrin is 5-10. For example, the DE value of maltodextrin can be 5, 6, 7, 8, 9, 10, or any range therebetween.

[0018] In this application, the DE value refers to the proportion of reducing sugars (calculated as glucose) in the dry matter of the syrup. According to national standards, the higher the DE value, the higher the grade of glucose syrup. The DE value can be measured by any method known to those skilled in the art. The specifications for maltodextrin in China's light industry standards are divided into three categories: DE values ​​≦10, ≦15, and ≦20. Low-DE maltodextrin is a widely used food ingredient. Due to its low sweetness, low hygroscopicity, and good solubility, it is often used as a flavor carrier, humectant, film-forming agent, fat substitute, etc.

[0019] In some embodiments of the present application, the DE value is measured by iodometric titration.

[0020] In some embodiments of the present application, the starch is amylose and amylopectin and related modified starches, preferably oxidized starches.

[0021] Native starch is a carbohydrate found in all plants in nature, especially in their seeds, roots, and tubers, where it serves as a source of nutrients for new growth. Starch is a glucose polymer consisting of anhydroglucose units linked together by α-D-glycosidic bonds. The glucose chains can be linear, slightly branched (amylose), or highly branched (amylopectin). Amylose molecules typically have a degree of polymerization between 1000 and 5000, while amylopectin molecules have an average degree of polymerization of over 1,000,000. Starch can be isolated from rice, corn, potato, wheat, cassava (Mandiospermum spp.), manioc, barley, oats, millet, and sorghum, among others. Modified starch is produced by at least partially decomposing natural starch, for example by treating it with inorganic acids, alkaline compounds, bleaching agents, oxidizing agents, enzymes, or acetylating agents. Oxidized starch is obtained by oxidizing starch with an oxidizing agent in an acidic, alkaline, or neutral medium. Oxidized starch lowers the gelatinization temperature of starch, reducing the viscosity of the hot paste and improving its thermal stability. The resulting product is white, transparent, and has excellent film-forming and freeze-thaw resistance. It is a low-viscosity, high-concentration thickener and is widely used in the textile, paper, food, and fine chemical industries.

[0022] In some embodiments of the present application, oxidized starch is measured by any method known to one of skill in the art.

[0023] In some embodiments of the present application, oxidized starch is measured by neutralization titration.

[0024] Cyclodextrins (CD) are formed by the action of cyclodextrin glucose residue transferase on glucose polymers such as starch, glycogen, and maltooligosaccharides. The three most common types are α-, β-, and γ-cyclodextrins. Of the three types, β-cyclodextrin (abbreviated as β-cyclodex, β-CD) is a water-soluble, non-reducing white crystalline or amorphous powder. Its primary structure is a conical cylinder with a central hole and open ends. The hollow structure allows the hydrophobic interior cavity to accommodate many guest molecules, including organic molecules, inorganic molecules, complexes, and inert gas molecules. Therefore, it can form various inclusion compounds through weak noncovalent interactions, thereby altering the physicochemical and biological properties of the guest molecules.

[0025] In some embodiments of the present application, the derivative of β-cyclodextrin is one or more selected from carboxymethyl-β-cyclodextrin, glucosyl-β-cyclodextrin, ethylenediamine-β-cyclodextrin, hydroxyethyl-β-cyclodextrin, hydroxypropyl-β-cyclodextrin, sulfonate-β-cyclodextrin, and quaternary ammonium-β-cyclodextrin.

[0026] In some embodiments of the present application, the composition consists of a wall material and gamma-aminobutyric acid.

[0027] In some embodiments of the present application, the mass ratio of the wall material to the γ-aminobutyric acid is (1-4):1, preferably (2-4):1. For example, the mass ratio of the wall material to the gamma-aminobutyric acid can be 1:1, 2:1, 3:1, 4:1, or any range therebetween.

[0028] In some embodiments of the present application, the wall material comprises β-cyclodextrin and its derivatives, and maltodextrin, and preferably, the mass ratio of the maltodextrin to the β-cyclodextrin and its derivatives is 1:(0.01-0.5), preferably 1:(0.2-0.3). For example, the mass ratio of the maltodextrin to the β-cyclodextrin and its derivatives can be 1:0.5, 1:0.45, 1:0.4, 1:0.35, 1:0.3, 1:0.25, 1:0.2, 1:0.15, 1:0.1, 1:0.05, 1:0.01, or any range therebetween.

[0029] In some embodiments of the present application, the wall material consists of β-cyclodextrin and its derivatives and maltodextrin.

[0030] In some embodiments of the present application, the wall material consists of β-cyclodextrin and maltodextrin.

[0031] In some embodiments of the present application, the wall material consists of β-cyclodextrin and maltodextrin with a DE value of 5-10.

[0032] In some embodiments of the present application, the wall material comprises β-cyclodextrin and its derivatives, and starch. Preferably, the mass ratio of the starch to the β-cyclodextrin and its derivatives is 1:(0.01-0.5), preferably 1:(0.2-0.3). For example, the mass ratio of the starch to the β-cyclodextrin and its derivatives can be 1:0.5, 1:0.45, 1:0.4, 1:0.35, 1:0.3, 1:0.25, 1:0.2, 1:0.15, 1:0.1, 1:0.05, 1:0.01, or any range therebetween.

[0033] In some embodiments of the present application, the wall material consists of β-cyclodextrin and its derivatives and starch.

[0034] In some embodiments of the present application, the wall material consists of β-cyclodextrin and starch.

[0035] In some embodiments of the present application, the wall material consists of β-cyclodextrin and oxidized starch.

[0036] The present application provides a method for preparing the above composition, comprising: Prepare a water solution A of the wall material. Prepare an aqueous solution B of γ-aminobutyric acid. An aqueous solution of γ-aminobutyric acid and an aqueous solution of the wall material are mixed to obtain aqueous solution C, which is then stirred and spray-dried to obtain the composition.

[0037] In some embodiments of the present application, in aqueous solution C, the mass ratio of the total mass of the wall material and the γ-aminobutyric acid to aqueous solution C is (0.5 to 2.5):10, preferably (1 to 2):10. For example, the mass ratio of the total mass of the wall material and the γ-aminobutyric acid to aqueous solution C can be 0.5:10, 0.75:10, 1:10, 1.25:10, 1.5:10, 1.75:10, 2:10, 2.25:10, 2.5:10, or any range therebetween.

[0038] In some embodiments of the present application, in aqueous solution C, the mass ratio of the total mass of the wall material and the γ-aminobutyric acid to aqueous solution C also refers to the solid content, i.e., in aqueous solution C, the solid content is 5 to 25%, preferably 10 to 20%. For example, in aqueous solution C, the solids content can be 5%, 6%, 7%, 8%, 9%, 10%, 11%, 12%, 13%, 14%, 15%, 16%, 17%, 18%, 19%, 20%, 21%, 22%, 23%, 24%, 25%, or any range therebetween.

[0039] In some embodiments of the present application, when solution C is stirred, the stirring temperature is 60 to 70°C, preferably 60 to 65°C. The stirring temperature may be 60°C, 61°C, 62°C, 63°C, 64°C, 65°C, 66°C, 67°C, 68°C, 69°C, 70°C, or any range therebetween.

[0040] In some embodiments of the present application, the spray drying inlet air temperature is 140-145°C and the spray drying outlet air temperature is 95-105°C. The spray drying inlet air temperature may be 140°C, 141°C, 142°C, 143°C, 144°C, 145°C, or any range therebetween. The spray drying outlet air temperature may be 95°C, 96°C, 97°C, 98°C, 99°C, 100°C, 101°C, 102°C, 103°C, 104°C, 105°C, or any range therebetween.

[0041] In some embodiments of the present application, an aqueous solution A of a wall material is prepared, the wall material comprising β-cyclodextrin and its derivatives and maltodextrin, preferably, the mass ratio of the maltodextrin to the β-cyclodextrin and its derivatives is 1:(0.01-0.5), or the wall material comprising β-cyclodextrin and its derivatives and starch, preferably, the mass ratio of the starch to the β-cyclodextrin and its derivatives is 1:(0.01-0.5), and the wall material solution is dissolved in deionized water at 70-80°C, stirred for 10-15 minutes, and cooled to 60-65°C to obtain a homogeneous solution. An aqueous solution B of γ-aminobutyric acid is prepared, and the aqueous solution of γ-aminobutyric acid is mixed with an aqueous solution of the wall material to obtain an aqueous solution C. When stirring solution C, the stirring temperature is controlled to 60 to 65°C, i.e., the temperature before spray drying is controlled to 60 to 65°C. In aqueous solution C, the mass ratio of the total mass of the wall material and the γ-aminobutyric acid to the mass of aqueous solution C is (1 to 2):10 so that the spray drying yield is 80% or more.

[0042] The present application provides a composite comprising the above composition.

[0043] The present application also provides for the use of the composition in food, health care products, and pharmaceutical formulations.

[0044] The present application also provides the use of the composition in food, health care products, and pharmaceutical ingredients.

[0045] The present application also provides the use of the composition to slow the Maillard reaction.

[0046] In the composition provided in the present application, the wall material used can, on the one hand, partially encapsulate γ-aminobutyric acid, and, on the other hand, can competitively absorb water, thereby reducing the probability that γ-aminobutyric acid comes into contact with water and effectively blocking moisture, thereby slowing down the involvement of moisture in the Maillard reaction in the formulated food.

[0047] The ingredients used in this application are safe and reliable, and this method effectively improves the browning problem caused by the Maillard reaction between γ-aminobutyric acid and reducing sugars in formulated foods, expanding the application of γ-aminobutyric acid in the food field. The product is pure in color and tasteless, can be dissolved into water-soluble products, has a simple preparation process, is easy to obtain raw materials, has a high yield, and is easy to popularize and apply.

[0048] [Table 1] [Example]

[0049] Example 1 To prepare aqueous solution A of wall material, 90 g of oxidized starch and 22.5 g of β-cyclodextrin were dissolved in 900 mL of deionized water at 75°C, stirred for 10 minutes, and cooled to 60°C to obtain an aqueous solution of wall material. The mass ratio of oxidized starch to β-cyclodextrin was 1:0.25, and the total mass of the oxidized starch and β-cyclodextrin was 112.5 g. To prepare aqueous solution B of γ-aminobutyric acid, 37.5 g of γ-aminobutyric acid was weighed and dissolved in 100 mL of deionized water to obtain aqueous solution B of γ-aminobutyric acid. The weight percentage of γ-aminobutyric acid in aqueous solution B was 37.5%. The aqueous solution of γ-aminobutyric acid B was gradually added proportionally to the aqueous solution of wall material A to obtain Solution C. In Solution C, the mass ratio of wall material to γ-aminobutyric acid was 3:1, the mass ratio of the total mass of wall material and γ-aminobutyric acid to aqueous solution C was 1.5:10, and the solids content was 15%. After the addition was completed, stirring and homogenization was continued for 30 minutes, the stirring temperature was controlled at 62°C, and then spray-dried in a spray dryer. The inlet air temperature of the spray dryer was 140°C, and the outlet air temperature of the spray dryer was 100°C. 136.8 g of powdery solid was obtained, and γ-aminobutyric acid S1 was prepared.

[0050] Here, the ratio of the mass of the finally obtained powdery solid to the mass of the composition (wall material and γ-aminobutyric acid) was recorded as the yield, and the yield of Example 1 was 91.2%.

[0051] Example 2 The only difference between Example 2 and Example 1 is that in preparing the aqueous solution A of the wall material, 60 g of oxidized starch and 15 g of β-cyclodextrin were dissolved in 900 mL of deionized water at 75°C, the mass ratio of the oxidized starch to β-cyclodextrin was 1:0.25, the total mass of the oxidized starch and β-cyclodextrin was 75 g, the mass ratio of the wall material to γ-aminobutyric acid was 2:1, and the solid content was 11.25%. All other conditions were the same.

[0052] Example 3 The only difference between Example 3 and Example 1 is that in preparing the aqueous solution A of the wall material, 120 g of oxidized starch and 30 g of β-cyclodextrin were dissolved in 900 mL of deionized water at 75°C, the mass ratio of oxidized starch to β-cyclodextrin was 1:0.25, the total mass of oxidized starch and β-cyclodextrin was 150 g, the mass ratio of wall material to γ-aminobutyric acid was 4:1, and the solid content was 18.75%. All other conditions were the same.

[0053] Example 4 The only difference between Example 4 and Example 1 is that in preparing the aqueous solution A of the wall material, 90 g of maltodextrin (the DE value of maltodextrin is 5-10) and 22.5 g of β-cyclodextrin were dissolved in 900 mL of deionized water at 75°C, the mass ratio of the maltodextrin with a DE value of 5-10 to the β-cyclodextrin was 1:0.25, the total mass of the maltodextrin with a DE value of 5-10 and the β-cyclodextrin was 112.5 g, the mass ratio of the wall material to γ-aminobutyric acid was 3:1, and the solid content was 15%; all other conditions were the same.

[0054] Example 5 The only differences between Example 5 and Example 1 are that in preparing aqueous solution A of the wall material, 90 g of oxidized starch and 22.5 g of β-cyclodextrin were dissolved in 1,200 mL of deionized water at 75°C, and in preparing aqueous solution B of γ-aminobutyric acid, 37.5 g of γ-aminobutyric acid was weighed and dissolved in 300 mL of deionized water to obtain aqueous solution B of γ-aminobutyric acid, the mass ratio of oxidized starch to β-cyclodextrin was 1:0.25, the total mass of oxidized starch and β-cyclodextrin was 112.5 g, the mass ratio of wall material to γ-aminobutyric acid was 3:1, and the solid content of the resulting aqueous solution C was 10%; other conditions were the same.

[0055] Example 6 The only differences between Example 6 and Example 1 are that in preparing aqueous solution A of the wall material, 90 g of oxidized starch and 22.5 g of β-cyclodextrin were dissolved in 650 mL of deionized water at 75°C, and in preparing aqueous solution B of γ-aminobutyric acid, 37.5 g of γ-aminobutyric acid was weighed and dissolved in 100 mL of deionized water to obtain aqueous solution B of γ-aminobutyric acid, the mass ratio of oxidized starch to β-cyclodextrin was 1:0.25, the total mass of oxidized starch and β-cyclodextrin was 112.5 g, the mass ratio of wall material to γ-aminobutyric acid was 3:1, and the solid content of the resulting aqueous solution C was 20%; other conditions were the same.

[0056] Example 7 The only difference between Example 7 and Example 1 is that in the preparation of the wall material aqueous solution A, 75 g of oxidized starch and 37.5 g of β-cyclodextrin were dissolved in 900 mL of deionized water at 75°C, the mass ratio of oxidized starch to β-cyclodextrin was 1:0.5, and the total mass of oxidized starch and β-cyclodextrin was 112.5 g; in the preparation of the wall material aqueous solution C, the mass ratio of the wall material to γ-aminobutyric acid was 3:1, and the solid content was 15%; all other conditions were the same.

[0057] Example 8 The only differences between Example 8 and Example 1 are that in the preparation of aqueous solution A of the wall material, 111.3 g of oxidized starch and 1.2 g of β-cyclodextrin were dissolved in 900 mL of deionized water at 75°C, the mass ratio of oxidized starch to β-cyclodextrin was 1:0.011, and the total mass of oxidized starch and β-cyclodextrin was 112.5 g; in aqueous solution C, the mass ratio of wall material to γ-aminobutyric acid was 3:1, and the solid content was 15%; all other conditions were the same.

[0058] Example 9 The only difference between Example 9 and Example 1 is that in preparing the aqueous solution A of the wall material, 112.5 g of maltodextrin (the DE value of maltodextrin is 5 to 10) was dissolved in 900 mL of deionized water at 75°C, and the solid content was 15%. The other conditions were the same.

[0059] Example 10 The only difference between Example 10 and Example 1 is that in preparing the aqueous solution A of the wall material, 112.5 g of oxidized starch was dissolved in 900 mL of deionized water at 75°C, and the solid content was 15%. The other conditions were the same.

[0060] Example 11 The only difference between Example 11 and Example 1 is that in preparing the aqueous solution A of the wall material, 112.5 g of β-cyclodextrin was dissolved in 900 mL of deionized water at 75°C, and the solid content was 15%. All other conditions were the same.

[0061] Example 12 The only difference between Example 12 and Example 1 is that in preparing the aqueous solution A of the wall material, 112.5 g of cornstarch was dissolved in 900 mL of deionized water at 75°C, and the solid content was 15%. The other conditions were the same.

[0062] Example 13 The only difference between Example 13 and Example 1 is that in preparing the aqueous solution A of the wall material, 112.5 g of maltodextrin was dissolved in 900 mL of deionized water at 75°C, and the solid content was 15%. The other conditions were the same.

[0063] Example 14 The difference between Example 14 and Example 1 is that in preparing the aqueous solution A of the wall material, 90 g of oxidized starch and 22.5 g of β-cyclodextrin were dissolved in 1675 mL of deionized water at 75°C. In preparing the aqueous solution B of gamma-aminobutyric acid, 37.5 g of gamma-aminobutyric acid was weighed and dissolved in 200 mL of deionized water to obtain the aqueous solution B of gamma-aminobutyric acid. In the obtained aqueous solution C, the total mass of oxidized starch and β-cyclodextrin was 112.5 g, the mass ratio of the wall material to gamma-aminobutyric acid in the aqueous solution C was 3:1, and the solid content was 8%, except that the other conditions were the same.

[0064] Example 15 The only differences between Example 15 and Example 1 are that in preparing aqueous solution A of the wall material, 90 g of oxidized starch and 22.5 g of β-cyclodextrin were dissolved in 500 mL of deionized water at 75°C, and in preparing aqueous solution B of γ-aminobutyric acid, 37.5 g of γ-aminobutyric acid was weighed and dissolved in 100 mL of deionized water to obtain aqueous solution B of γ-aminobutyric acid. In the resulting aqueous solution C, the total mass of oxidized starch and β-cyclodextrin was 112.5 g, the mass ratio of the wall material to γ-aminobutyric acid in aqueous solution C was 3:1, and the solids content was 25%. All other conditions were the same.

[0065] Example 16 The only difference between Example 16 and Example 1 is that in the preparation of the wall material aqueous solution A, 90 g of cornstarch and 22.5 g of β-cyclodextrin were dissolved in 900 mL of deionized water at 75°C, the mass ratio of cornstarch to β-cyclodextrin was 1:0.25, and the total mass of cornstarch and β-cyclodextrin was 112.5 g; in the preparation of the wall material aqueous solution C, the mass ratio of γ-aminobutyric acid to γ-aminobutyric acid was 3:1, and the solid content was 15%. All other conditions were the same.

[0066] Example 17 The only difference between Example 17 and Example 1 is that in the preparation of the wall material aqueous solution A, 90 g of maltodextrin and 22.5 g of β-cyclodextrin were dissolved in 900 mL of deionized water at 75°C, the mass ratio of maltodextrin to β-cyclodextrin was 1:0.25, and the total mass of maltodextrin and β-cyclodextrin was 112.5 g; in the preparation of the wall material aqueous solution C, the mass ratio of the wall material to γ-aminobutyric acid was 3:1, and the solid content was 15%; all other conditions were the same.

[0067] The parameters for Examples 1 to 17 are shown in Table 2.

[0068] [Table 2-1]

[0069] [Table 2-2]

[0070] Experimental Example 1: Sample Stability Study The samples of Examples 1 to 4, 7 to 13, and 16 to 17 were mixed with maltose, lactose, glucose, fructose, and arabinose in a 1:1 ratio, respectively, and subjected to a high-temperature accelerated test at 60°C. After 14 days, the color change was observed, and the GABA content was detected according to the following method.

[0071] 1. Equipment: High-performance liquid chromatography equipped with a UV detector, autosampler, and data processing system. Chromatography column: Hypersil ODS C18, 5 μm, 4.6 x 250 mm (a chromatography column with equivalent or higher separation efficiency). Analytical balance: accuracy 0.1 mg. Ultrasonic dissolution device.

[0072] 2. Reagents: Methanol (chromatography grade); Acetonitrile (chromatography grade); o-phthalaldehyde (OPA); Crystalline sodium acetate; Glacial acetic acid; γ-aminobutyric acid standard (purity ≥ 99.0%); Boric acid; Sodium hydroxide

[0073] 3. Analysis Procedure Preparation of standard solution: Accurately weigh 0.5 g of γ-aminobutyric acid standard, dissolve in water and make up to 100 mL, mix well, take 10 mL and make up to 100 mL, filter through a 0.22 μm filter membrane, collect the filtrate and use it as the standard solution. Preparation of sample solution: Accurately weigh 0.5 to 2.0 g of sample, dissolve in water and make up to 100 mL, mix well, take 10 mL and make up to 100 mL, filter through a 0.22 μm filter membrane, collect the filtrate and use it as the test sample solution. Preparation of 0.4 mol / L borate buffer: Weigh out 2.47 g of boric acid, add approximately 80 mL of water, adjust the pH to 10.2 with sodium hydroxide, and make up to 100 mL with water. Preparation of derivatization reagent: 0.1 g of o-phthalaldehyde (OPA) was weighed out and dissolved in 1 mL of acetonitrile, and 130 μL of mercaptoethanol was added. 0.4 mol / L borate buffer was added to make up to 10 mL.

[0074] 4. Chromatographic Analysis Conditions Mobile phase A: Weigh out 7.5 g of crystalline sodium acetate, dissolve in water, and make up to 1000 mL. Add 5% acetic acid dropwise to adjust the pH to 7.20 ± 0.02, filter, and set aside. Phase B: Chromatography-grade acetonitrile, filter, and set aside. The mobile phase ratio for the method run is 75% Phase A + 25% Phase B. Flow rate: 1.0 mL / min. Detection wavelength: 338 nm. Column temperature: 40°C.

[0075] 5. Sample Measurement Perform pre-column derivatization using an autosampler, perform chromatographic analysis, record the retention time and peak area of ​​the chromatographic peak, and obtain the area ratio of the peak area to the concentration of the standard solution (dry basis). Repeat this operation six times, and the relative standard deviation should be less than 3%.

[0076] Take the prepared samples for measurement. Prepare two portions of each sample, measure each portion twice, and record the retention time and peak area of ​​the chromatographic peak. The retention times of the sample and the standard solution must be consistent. Calculate the corresponding concentration of γ-aminobutyric acid by the external standard method.

[0077] The content of γ-aminobutyric acid in the sample is calculated according to the following formula:

[0078]

number

[0079] During the ceremony: X1—the content of gamma-aminobutyric acid in the sample; A i - the peak area of ​​γ-aminobutyric acid in the sample; m S - Mass of γ-aminobutyric acid standard (unit: grams (g)); n S - Loss on drying of γ-aminobutyric acid standard; Purity of C-γ-aminobutyric acid standard; V S-Dilution volume of γ-aminobutyric acid standard (unit: milliliters (mL)); A S - peak area of ​​γ-aminobutyric acid standard; m—mass of the weighed sample in grams (g); n—loss on drying of the sample; V—Dilution volume of sample in milliliters (mL). The calculation result will be rounded to the first decimal place.

[0080] The results of Examples 1 to 4, Examples 7 to 13, and Examples 16 to 17 are shown in FIG.

[0081] γ-aminobutyric acid content tests using low-DE maltodextrin (S9), oxidized starch (S10), and β-cyclodextrin (S11) wall materials showed a consistent decrease in γ-aminobutyric acid content after blending with various sugars and accelerating at high temperatures. Among these, the γ-aminobutyric acid content decreased by 60%–70% after blending with glucose and arabinose and accelerating at high temperatures. However, samples S12 and S13, which were prepared using cornstarch and maltodextrin as wall materials, decreased by 67–80% and less than 10%, respectively, after blending with glucose and arabinose and accelerating at high temperatures. This indicates that cornstarch and maltodextrin are less stable to γ-aminobutyric acid. Compared with experimental examples S7 and S8, when samples S1-S4 were blended with glucose, fructose, lactose, arabinose, and maltose, the γ-aminobutyric acid content of S1-S3 and S4 remained almost unchanged after accelerated growth at high temperatures, demonstrating excellent results. The γ-aminobutyric acid content of experimental samples S7 and S8 decreased by approximately 80%. Samples S16 and S17, which were prepared by blending cornstarch and maltodextrin with β-cyclodextrin as wall materials, respectively, also blended with glucose and arabinose. After accelerated growth at high temperatures, the γ-aminobutyric acid content decreased by 75-80% and less than 10%, respectively. Experimental results showed that samples prepared by spray-drying γ-aminobutyric acid with a wall material composed of oxidized starch and β-cyclodextrin in a ratio of 1:0.2-1:0.3 showed improved stability and effective retardation of the Maillard reaction.

[0082] As shown in Figure 2, the color reaction test showed that the samples prepared by spray-drying S1 (oxidized starch:β-cyclodextrin = 1:0.25), S4 (low DE value MD:β-cyclodextrin = 1:0.25), S11 (β-cyclodextrin), S12 (corn starch), and S13 (maltodextrin) with γ-aminobutyric acid showed the smallest color change after blending with various sugars and accelerating under high temperature conditions. The color reaction test showed that the color slowly changed from white to yellow or yellowish, and gradually turned brown or black as the Maillard reaction time increased and the reaction depth deepened.

[0083] [Table 3]

[0084] As can be seen from Table 3 above, the recovery rate of the samples decreases as the solid content increases, and when the solid content is 8% (S14) and 25% (S15), and the moisture content is above 3%, the presence of moisture increases the intensity of the Maillard reaction. Considering the energy consumption, yield, and quality comprehensively, the optimal condition is a solid content of 15%-20%.

Claims

1. A composition comprising a wall material and γ-aminobutyric acid, the wall material is one or more selected from β-cyclodextrin and its derivatives, maltodextrin, starch, chitosan, and glucose; Preferably, the maltodextrin has a DE value of 5 to 10 and the starch is an oxidized starch. composition.

2. The composition according to claim 1, wherein the mass ratio of the wall material to the γ-aminobutyric acid is (1-4):1, preferably (2-4):

1.

3. the wall material comprises β-cyclodextrin and its derivatives, and maltodextrin; Preferably, the mass ratio of the maltodextrin to the β-cyclodextrin and its derivatives is 1:(0.01 to 0.5), preferably 1:(0.2 to 0.3); The composition of claim 1.

4. the wall material comprises β-cyclodextrin and its derivatives, and starch; Preferably, the mass ratio of the starch to the β-cyclodextrin and its derivatives is 1:(0.01 to 0.5), preferably 1:(0.2 to 0.3); The composition of claim 1.

5. A method for preparing the composition according to any one of claims 1 to 4, comprising the steps of: Prepare an aqueous solution A of the wall material; An aqueous solution B of γ-aminobutyric acid is prepared. A method for obtaining the composition by mixing an aqueous solution of γ-aminobutyric acid with an aqueous solution of a wall material to obtain aqueous solution C, stirring the aqueous solution, and spray-drying the aqueous solution C.

6. In the aqueous solution C, the mass ratio of the total mass of the wall material and γ-aminobutyric acid to the aqueous solution C is (0.5 to 2.5):10, preferably (1 to 2):

10. The method of claim 5.

7. A complex comprising the composition according to any one of claims 1 to 4 or the composition prepared by the method according to any one of claims 5 to 6.

8. Use of the composition according to any one of claims 1 to 4 or the composition prepared by the method according to any one of claims 5 to 6 in food and pharmaceutical preparations.

9. Use of the composition according to any one of claims 1 to 4 or the composition prepared by the method according to any one of claims 5 to 6 in food and pharmaceutical raw materials.

10. Use of a composition according to any one of claims 1 to 4 or a composition prepared by a method according to any one of claims 5 to 6 to slow down the Maillard reaction.

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