Low-AGEs content cookies and preparation method thereof

Abstract

The invention relates to the technical field of food, in particular to cookies with low AGEs content and a preparation method of the cookies, and the preparation method comprises the step of adding EGCG esterification products into the cookies, the EGCG esterification product is formed by esterification of EGCG and fatty acyl chloride. Fatty acyl chloride is used for esterification of EGCG, esterification treatment can make EGCG esterification products maintain stability and have better fat solubility, harmful products AGEs can be significantly reduced when the EGCG esterification products are applied to cookies, and the original quality of the cookies is not affected.

Description

Technical Field

[0001] The invention relates to the technical field of food, and in particular to a cookie with low AGEs content and a preparation method thereof. Background Art

[0002] Advanced glycation end products (AGEs) are a series of products produced by non-enzymatic reactions between amino compounds such as proteins or amino acids and carbonyl compounds mainly composed of reducing sugars. Intake from food is the main source of exogenous accumulation of AGEs in the human body. The intake of high-AGE foods will increase the content of AGEs in human blood and urine, thereby increasing the risk of chronic diseases such as diabetes, chronic kidney disease, and cardiovascular disease.

[0003] A variety of reactions will occur in cookies during the baking process, including Maillard reaction, lipid oxidation and caramelization reaction. These reactions are the main ways in which cookies produce quality characteristics and harmful products of thermal processing during baking, including the production of AGEs.

[0004] At present, some studies have been conducted to reduce the formation of AGEs in food by adding exogenous substances, such as using κ-carrageenan to inhibit the formation of AGEs in baked cakes. However, the hardness of the cake is positively correlated with the concentration of κ-carrageenan. The hardness of the cake with 2% (w / w) carrageenan is 42.74% higher than that of the control group, and the taste is unacceptable. There is also a method of using flavonoids, a natural active ingredient, to reduce the content of AGEs in baked foods. Although it does not affect the color and flavor of baked cakes, its inhibition rate of AGEs in baked cakes is not good.

[0005] In summary, in the research field of inhibiting the production of AGEs in baked foods, there is still a lack of a method that can not only maintain the original quality of baked foods but also effectively inhibit the formation of harmful products of thermal processing therein. Summary of the invention

[0006] The inventors have found through research that EGCG esterification products can reduce advanced glycation end products in cookies, and thus propose the present invention.

[0007] Tea polyphenols are polyphenols extracted from tea leaves. Catechins are their main components, and epigallocatechin gallate (EGCG) is the most important active substance.

[0008] EGCG has strong antioxidant capacity and the ability to capture dicarbonyl compounds. It can reduce the generation of harmful products AGEs by scavenging free radicals and capturing dicarbonyl compounds, which are key intermediates in the generation of AGEs. However, EGCG has poor stability and its effect in inhibiting the generation of AGEs is limited during the thermal processing of food. The inventors found that the esterification of EGCG with fatty acid chloride can maintain the stability of the esterified EGCG product and have better fat solubility. Its application in cookies can significantly reduce harmful products AGEs without affecting the original quality of the cookies.

[0009] A method for preparing cookies comprises adding an EGCG esterification product into the cookies; the EGCG esterification product is formed by esterification of EGCG and fatty acid chloride.

[0010] Specifically, the fatty acid chloride is butyryl chloride, such as n-butyryl chloride.

[0011] Specifically, the EGCG esterification product is EGCG monobutyrate, or EGCG dibutyrate, or a mixture of the two (EGCG butyrate for short) generated by a substitution reaction between EGCG and n-butyryl chloride.

[0012] EGCG undergoes a substitution reaction with n-butyryl chloride, and esterification products with different degrees of substitution can be separated from the synthesized crude product, which is mainly a monosubstituted product, named EGCG monobutyrate; it also contains some disubstituted products, named EGCG dibutyrate; the mixture of the two is called EGCG butyrate.

[0013] Specifically, the preparation of the EGCG esterification product is carried out under the condition of using ethyl acetate as the reaction solvent.

[0014] Specifically, the esterification reaction time of EGCG and fatty acyl chloride (such as butyryl chloride) is 1-2 hours, preferably 1.5 hours; the reaction temperature is 40-50°C, preferably 45°C.

[0015] Specifically, based on the total weight of the cookies, the content of the EGCG esterification product in the cookies is 0.01wt%-0.30wt%, preferably 0.25wt%.

[0016] Specifically, the preparation method comprises: blending the EGCG esterification product with shortening, and then preparing dough with other ingredients, and then preparing cookies.

[0017] In the present invention, the ingredients for preparing the cookies can refer to the prior art and are not particularly limited in the present invention.

[0018] The present invention also provides cookies prepared by the method.

[0019] The present invention also provides application of the EGCG esterification product in preparing cookies.

[0020] In some embodiments, the AGEs content in the cookies of the present invention can be reduced to 60%-72%, for example 66.3%.

[0021] The present invention uses the esterification product of EGCG to inhibit the generation of AGEs in cookies, thereby solving the problem of excessive generation of AGEs in baked cookies without affecting the original quality of the cookies.

[0022] Experiments have shown that the esterification product of EGCG has an inhibition rate of 39.4% on the fluorescent AGEs in cookies and a representative substance of non-fluorescent AGEs in cookies, carboxymethyl lysine (N ε The inhibition rate of CML was 33.3%, and that of carboxyethyl lysine (N-(carboxymethyl)lysine, another representative substance of non-fluorescent AGEs in cookies was 33.3%. ε -(carboxyethyl)lysine, CEL) had an inhibition rate of 28.3%, which can achieve a good inhibitory effect.

[0023] The present invention adds EGCG esterification products during the baking process of the cookies, which has little effect on the original color, hardness, moisture content, etc. of the cookies. While retaining the original quality of the cookies, it can also effectively inhibit AGEs generated during the processing, thereby improving the safety of the cookies.

[0024] The method of the present invention is simple and efficient, has good inhibition effect, low cost and does not require expensive equipment, and is suitable for large-scale production. Compared with other technical solutions, the solvent of the present invention has low toxicity and is easy to remove, and the reaction conditions are mild and environmentally friendly, so it is a feasible solution. BRIEF DESCRIPTION OF THE DRAWINGS

[0025] Figure 1 This is the mass spectrum of EGCG and its esterification products EGCG monobutyrate and EGCG dibutyrate. DETAILED DESCRIPTION

[0026] In order to make the above-mentioned objects, features and advantages of the present invention more obvious and easy to understand, the specific embodiments of the present invention are described in detail below in conjunction with the accompanying drawings. In the following description, many specific details are set forth to facilitate a full understanding of the present invention. However, the present invention can be implemented in many other ways different from those described herein, and those skilled in the art can make similar improvements without violating the connotation of the present invention, so the present invention is not limited by the specific implementation disclosed below.

[0027] Unless otherwise specified, various raw materials, reagents, instruments and equipment used in the present invention can be purchased from the market or obtained by existing methods.

[0028] The following is the preparation method of EGCG esterification product:

[0029] 1. EGCG butyrate, EGCG monobutyrate, EGCG dibutyrate

[0030] 1) Take 5 g (10.91 mmol) of EGCG monomer and dissolve it in 50 mL of ethyl acetate. Stir continuously for 30 min in a 45°C water bath to fully dissolve the EGCG in ethyl acetate.

[0031] 2) Add 5 g of sodium bicarbonate to the mixed solution, slowly dropwise add 21.82 mmol of n-butyryl chloride as an acyl donor within 30 min, and continue stirring at 45 °C for 1.5 h to complete the esterification reaction.

[0032] 3) After the reaction is completed, the mixture is cooled to room temperature and filtered. After the filtrate is washed three times with 60° C. distilled water, the ethyl acetate phase is separated and the water therein is removed using anhydrous sodium sulfate.

[0033] 4) Dry in a vacuum oven at 45° C. for 12 h to finally obtain a crude EGCG esterification product, i.e., a crude EGCG butyrate product. The collected powder is sealed and stored in a desiccator for later use.

[0034] The crude product of EGCG esterification product was separated by column chromatography to obtain EGCG monobutyrate and EGCG dibutyrate. The specific steps are as follows: In order to separate the crude product of EGCG esterification product, it was dissolved in a developing agent (petroleum ether: ethyl acetate: formic acid = 1:1:0.05, volume ratio), and petroleum ether, ethyl acetate and formic acid were prepared as an eluent in a volume ratio of 1:1:0.05 for elution, and the compounds in the eluent were monitored by thin layer chromatography technology to collect the target compounds. Finally, nitrogen was used to blow dry the solvent in the collected liquid to obtain two purer monomer products, namely EGCG monobutyrate and EGCG dibutyrate.

[0035] EGCG undergoes a substitution reaction with n-butyryl chloride, and esterification products with different degrees of substitution can be separated from the synthesized crude product, mainly monosubstituted, named EGCG monobutyrate, and also partially disubstituted, named EGCG dibutyrate. The mixture of the two is also called EGCG butyrate.

[0036] 2. EGCG monooctanoate, EGCG dioctanoate

[0037] The preparation method is different from the preparation method of EGCG butyrate only in that n-butyryl chloride is replaced by octanoyl chloride; the crude EGCG esterification product is separated by column chromatography to obtain EGCG monooctanoate and EGCG dioctanoate.

[0038] 3. EGCG monolaurate

[0039] The preparation method is different from the preparation method of EGCG butyrate only in that n-butyryl chloride is replaced by lauroyl chloride; and the crude EGCG esterification product is separated by column chromatography to obtain EGCG monolaurate.

[0040] 4. EGCG monopalmitate

[0041] The preparation method thereof is different from the preparation method of EGCG butyrate only in that n-butyryl chloride is replaced by palmitoyl chloride; and the crude EGCG esterification product is separated by column chromatography to obtain EGCG monopalmitate.

[0042] Example 1

[0043] This embodiment provides a cookie, and the preparation method thereof is as follows:

[0044] (1) Dissolve 0.42 g of EGCG butyrate (i.e., a mixture of EGCG monobutyrate and EGCG dibutyrate) in 32 g of shortening, and quickly stir the shortening in a mixing bowl until it is fluffy. Then, add 33.6 g of sucrose, 1 g of salt, 0.8 g of baking soda, and 0.8 g of skim milk powder, and quickly stir until all are dissolved.

[0045] (2) Mix 1.2 g of high fructose syrup and 17.6 g of deionized water, and thoroughly dissolve 0.4 g of ammonium bicarbonate therein. Pour the resulting mixed solution into a mixing bowl and stir evenly. Then, divide 80 g of flour into three equal parts, pour them into the mixing bowl one by one, and mix evenly.

[0046] (3) Use a mold to process the dough into cookie dough with a diameter of about 5 cm and a thickness of about 2 mm.

[0047] (4) Bake the cookie dough at 205° C. for 11 min to obtain cookies.

[0048] Example 2

[0049] This embodiment provides a cookie with low AGEs content, and the preparation method thereof is different from that of Example 1 only in that EGCG butyrate is replaced by an equal amount of EGCG monobutyrate.

[0050] Example 3

[0051] This embodiment provides a cookie with low AGEs content, and the preparation method thereof is different from that of Example 1 only in that EGCG butyrate is replaced by an equal amount of EGCG dibutyrate.

[0052] Comparative Example 1

[0053] This comparative example provides a cookie, the preparation method of which is different from that of Example 1 only in that EGCG butyrate is not added.

[0054] Comparative Example 2

[0055] This comparative example provides a cookie, and its preparation method is as follows:

[0056] (1) 32 g shortening was placed in a mixing bowl and stirred rapidly until fluffy. Then, 33.6 g sucrose, 1.0 g salt, 0.8 g baking soda, and 0.8 g skim milk powder were added and stirred rapidly until all dissolved.

[0057] (2) Dissolve 0.42g EGCG in 17.6g deionized water, add 1.2g high fructose syrup, mix well, and thoroughly dissolve 0.4g ammonium bicarbonate. Pour the resulting mixed solution into a mixing bowl and stir well. Then, divide 80g flour into three equal parts and pour them into the mixing bowl one by one, making sure to mix thoroughly each time.

[0058] (3) Take the dough out of the mixing bowl and use a mold to shape the dough into cookie dough with a diameter of about 5 cm and a thickness of about 2 mm.

[0059] (4) Bake the cookie dough at 205° C. for 11 min to obtain cookies.

[0060] Comparative Example 3

[0061] This comparative example provides a cookie, the preparation method of which is different from that of Example 1 only in that EGCG butyrate is replaced by an equal amount of tea polyphenol palmitate.

[0062] The baked cookie samples of the above embodiments and comparative examples were cooled down at ambient temperature and subjected to subsequent analysis.

[0063] Experiment 1

[0064] The content of fluorescent AGEs in cookies is evaluated by measuring the fluorescence value. The specific process includes:

[0065] Accurately weigh 250 mg of cookie powder sample, add 4.75 mL of extraction buffer (0.05% Tween-20, 1% SDS, 5% β-mercaptoethanol, 50 mM Tris-HCl, pH 7.4), mix thoroughly and extract in a room temperature water bath oscillator for 12 hours. Collect the supernatant after centrifugation at 10000×g for 20 minutes. Dilute the supernatant appropriately, and then use a fluorescence spectrophotometer to measure the fluorescence signal intensity of the test solution at an excitation wavelength of 325 nm and an emission wavelength of 440 nm.

[0066] The results are shown in Table 1.

[0067] Table 1 Fluorescence intensity of cookies (P<0.05)

[0068] sample Fluorescence intensity (AU) Comparative Example 1 <![CDATA[1627.00±7.94 a ]]> Comparative Example 2 <![CDATA[1022.33±7.64 c ]]> Example 1 <![CDATA[986.23±6.05 d ]]> Comparative Example 3 <![CDATA[1345.33±6.51 b ]]>

[0069] The fluorescence intensity was used as an indicator to evaluate the inhibitory ability of three inhibitors, EGCG (Comparative Example 2), EGCG butyrate (Example 1) and tea polyphenol palmitate (Comparative Example 3), on the formation of fluorescent AGEs during cookie baking. Table 1 shows the inhibitory effect of EGCG, EGCG butyrate and tea polyphenol palmitate on the formation of fluorescent AGEs during cookie baking when the addition amount was 0.25% (w / w). As can be seen from Table 1, the addition of these three inhibitors to cookies can effectively inhibit the formation of fluorescent AGEs. The inhibition rates of EGCG, EGCG butyrate and tea polyphenol palmitate on the formation of fluorescent AGEs in cookies were 37.2%, 39.4% and 17.3%, respectively.

[0070] Experiment 2

[0071] Ultra-high performance liquid chromatography-tandem mass spectrometry (UPLC-MS / MS) was used to quantitatively analyze CML and CEL in the test solution. The specific process included:

[0072] Weigh about 100 mg of cookie powder, add 3 mL of n-hexane, shake vigorously, centrifuge at 6000×g for 10 min, discard the upper solvent, and repeat the degreasing to ensure that the sample is thoroughly degreased. After degreasing, the sample is dried to powder in nitrogen. Add 1.5 mL of sodium borate buffer solution (0.2 mol / L, pH 9.2) and 1 mL of sodium borohydride (1 mol / L dissolved in 0.1 mmol / L sodium hydroxide) to the sample and reduce it overnight at 4°C. Add 4 mL of hydrochloric acid (final concentration of 6 mol / L) to the reduced sample, fill the container with nitrogen, seal it and hydrolyze it at 110°C for 24 hours. After the hydrolysis was completed, the cooled hydrolyzate was filtered and fixed to 10 mL. 500 μL was accurately drawn and dried with nitrogen at 60 °C. 150 μL of an internal standard mixture containing 71.25 ng of d4-CML and 66 ng of d4-CEL was added, and then 2 mL of 0.1 mol / L hydrochloric acid solution was added. After mixing well, it was used for solid phase extraction.

[0073] Solid phase extraction: First, activate the Oasis MCX solid phase extraction column with methanol (3 mL) and equilibrate with 0.1 mol / L hydrochloric acid (3 mL), load the sample at a rate of about 1 to 2 drops / second, then rinse with 0.1 mol / L hydrochloric acid (3 mL) and ultrapure water (3 mL), and finally elute with 95% ammoniated methanol. Dry the eluate with nitrogen at 40°C, redissolve it in 300 μL of ultrapure water, and filter it with a 0.22 μm filter membrane for UPLC-MS / MS detection.

[0074] UPLC conditions: the chromatographic column is a Waters X-Bridge C18 column (2.1×100 mm, 3.5 μm); the column temperature is 35°C; the injection volume is 5 μL; the mobile phase: phase A is ultrapure water, phase B is acetonitrile, flow rate is 0.2 min / mL, 0~0.1 min, 95% A; 0.1~5 min, 40% A; 5~7 min, 0% A; 7~9 min, 0% A; 9~10 min, 95% A.

[0075] MS / MS conditions: ion source mode was ESI+; monitoring mode was MRM; capillary voltage was 3.55 kV; ion source temperature was 150 °C; desolvation temperature was 400 °C; desolvation gas flow rate was 800 L / h; cone gas flow rate was 50 L / h; desolvation gas and cone gas were nitrogen; collision gas was argon.

[0076] The results are shown in Table 2.

[0077] Table 2 Contents of CML and CEL in cookies (P<0.05)

[0078] sample CML (μg / g) CEL(μg / g) Comparative Example 1 <![CDATA[148.21±3.88 a ]]> <![CDATA[115.19±1.13 a ]]> Comparative Example 2 <![CDATA[120.54±0.97 b ]]> <![CDATA[93.58±0.27 b ]]> Example 1 <![CDATA[98.86±2.18 d ]]> <![CDATA[82.58±1.99 d ]]> Comparative Example 3 <![CDATA[113.77±2.30 c ]]> <![CDATA[90.91±0.81 c ]]>

[0079] Table 2 shows the effects of EGCG (Comparative Example 2), EGCG butyrate (Example 1) and tea polyphenol palmitate (Comparative Example 3) on the production of CML and CEL during cookie baking. As can be seen from Table 2, EGCG butyrate has a more significant inhibitory effect on CML and CEL.

[0080] Experiment 3

[0081] The test results of color, hardness and moisture content of the cookies of Comparative Example 1, Comparative Example 2, Example 1 and Comparative Example 3 are shown in Table 3.

[0082] Table 3 Color, hardness and moisture content of cookies (P<0.05)

[0083]

[0084] Table 3 shows the effects of EGCG (Comparative Example 2), EGCG butyrate (Example 1) and tea polyphenol palmitate (Comparative Example 3) on the quality attributes of cookies, including moisture content, color and hardness. The color of cookies will affect the consumer's acceptability; moisture content affects the taste and shelf life. High moisture content may lead to softening, microbial contamination and oil oxidation, reducing its shelf life; hardness is an important indicator for evaluating the texture of cookies, affecting processing and sensory quality. As shown in Table 1, compared with the blank control group (Comparative Example 1), the addition of EGCG, EGCG butyrate and tea polyphenol palmitate had no significant effect on the moisture content and hardness of the cookies, and had little effect on the color of the cookies, which was within the acceptable range for consumers.

[0085] Experiment 4

[0086] In this experiment, the antioxidant capacity of EGCG monobutyrate and EGCG dibutyrate was evaluated by peroxide value (POV). POV is a widely used and accepted indicator of oil stability. The degree of oil oxidation is evaluated by measuring POV during oil oxidation.

[0087] Accurately weigh 0.02g of sample and add it to 100g of soybean oil, mix thoroughly, store the mixture at 60℃ for 15 days, and set the non-added group as the blank control group. The POV of soybean oil after 15 days of storage was determined by titration. Take 0.5mL of sample and 10mL of chloroform-glacial acetic acid mixture (2:3, v / v) and place it in a 100mL iodine flask, add 0.5mL of saturated potassium iodide solution to the flask, cover the bottle cap tightly, shake gently for 30s to mix thoroughly, and react for 3min in a light-proof environment. After the reaction is completed, add 30mL of water to the flask, shake well, and titrate the mixture with sodium thiosulfate standard solution. When the solution color reaches light yellow, it means that the titration end point is approaching. At this time, add 0.5mL of 0.5% starch indicator to the flask and continue titrating. When the blue color in the solution disappears completely, it means that the titration has reached the end point. The calculation formula of POV is:

[0088]

[0089] Where: V and V0 represent the volume of sodium thiosulfate standard solution consumed by the sample and blank sample, in mL; c, the concentration of the sodium thiosulfate standard solution, in mol / L; 0.1269 represents the mass of iodine equivalent to 1.00mL1.000mol / L sodium thiosulfate standard titration solution; m represents the mass of the sample, in g; 100 represents the conversion factor.

[0090] The experimental results are shown in Table 4. As can be seen from Table 4, the introduction of fatty acyl groups increases the lipid solubility of EGCG and its solubility in lipids, making its antioxidant capacity in lipids more effective. Compared with EGCG, EGCG monobutyrate and EGCG dibutyrate can significantly slow down the formation of oxidation products, thereby reducing POV. The increase in the lipid solubility of EGCG esterification products helps them to be more evenly dispersed in lipids, making these products closer to the interface where free radicals are generated.

[0091] Table 4 POV of soybean oil after 15 days of storage (P<0.05)

[0092] sample POV(g / 100g) blank <![CDATA[1.27±0.02 a ]]> EGCG <![CDATA[1.05±0.01 b ]]> EGCG Monobutyrate <![CDATA[0.25±0.00 d <!-- 6 -->]]> EGCG dibutyrate <![CDATA[0.33±0.00 c ]]>

[0093] Experiment 5

[0094] The mass spectra of EGCG and its esterification products EGCG monobutyrate and EGCG dibutyrate are shown in Figure 1 . Figure 1 In the figure, (A) is EGCG; (B) is EGCG monobutyrate; (C) is EGCG dibutyrate.

[0095] EGCG mass spectrum interpretation: In ESI-mode, the signal peak m / z 457 represents EGCG (Mw 458) losing one H +The obtained quasi-molecular ion peak [MH] - , and the other signal peak m / z 915 corresponds to [2M-H] - .

[0096] Explanation of mass spectrum of EGCG monobutyrate: In ESI-mode, the signal peak of m / z 527 corresponds to the loss of one H + The quasi-molecular ion peak formed [MH] - , another signal peak m / z1055 represents [2M-H] - peak.

[0097] Explanation of the mass spectrum of EGCG dibutyrate: In ESI-mode, the signal peak of m / z 597 corresponds to the loss of one H + The quasi-molecular ion peak formed [MH] - , and the other signal peak m / z 1195 represents [2M-H] - peak.

[0098] Experiment 6 Effect of EGCG esterification products on the formation of AGEs in food simulation system

[0099] 1 Experimental methods

[0100] 1.1 Establishment of simulation system

[0101] 100mmol / L glucose, 100mmol / L lysine and 100mmol / L oleic acid were mixed in a citric acid-phosphate buffer solution at pH 7, and then different concentrations of EGCG and its esterification product solutions were added respectively. After mixing evenly, the mixture was placed in a pressure bottle and reacted in an oil bath at 120℃ for 1h. After the reaction was completed, the pressure bottle was placed in ice water for rapid cooling, and the supernatant was centrifuged after cooling to be tested. An equal volume of methanol was used to replace the EGCG and its esterification product solution as the control group.

[0102] 1.2 Determination of fluorescent AGEs content in the simulation system

[0103] The content of fluorescent AGEs in the simulation system was evaluated by measuring the fluorescence value. First, the test solution was diluted by an appropriate multiple, and then the fluorescence signal intensity of the test solution was measured using a fluorescence spectrophotometer at an excitation wavelength of 325 nm and an emission wavelength of 440 nm.

[0104] The calculation formula of fluorescent AGEs inhibition rate is as follows:

[0105]

[0106] 1.3 Determination of the content of non-fluorescent AGEs (represented by CML and CEL) in the simulation system

[0107] The reaction solution was diluted appropriately, 150 μL of the diluted solution was taken, and 150 μL of the internal standard mixture containing 71.25 ng of d4-CML and 66 ng of d4-CEL was added. After mixing evenly, it was filtered through a 0.22 μm filter membrane. UPLC-MS / MS was used to quantitatively analyze CML and CEL in the test solution. Compared with the control group, the inhibition rate of EGCG and its esterification products on CML and CEL at each added concentration was calculated.

[0108] UPLC conditions: the chromatographic column is a Waters X-Bridge C18 column (2.1×100 mm, 3.5 μm); the column temperature is 35°C; the injection volume is 5 μL; the mobile phase: phase A is ultrapure water, phase B is acetonitrile, flow rate is 0.2 min / mL, 0~0.1 min, 95% A; 0.1~5 min, 40% A; 5~7 min, 0% A; 7~9 min, 0% A; 9~10 min, 95% A.

[0109] MS / MS conditions: ion source mode was ESI+; monitoring mode was MRM; capillary voltage was 3.55 kV; ion source temperature was 150 °C; desolvation temperature was 400 °C; desolvation gas flow rate was 800 L / h; cone gas flow rate was 50 L / h; desolvation gas and cone gas were nitrogen; collision gas was argon.

[0110] 2 Experimental results

[0111] 2.1 Effect of EGCG esterification products on the formation of fluorescent AGEs in the simulation system

[0112] The results are shown in Table 5.

[0113] Table 5 Inhibition rate of EGCG and its esterification products on fluorescent AGEs in the simulation system (P<0.05)

[0114]

[0115] Under the conditions of the simulated system, EGCG and its esterification products showed an inhibitory effect on the formation of fluorescent AGEs, and the inhibitory effect gradually increased with the increase of the added amount. Among them, EGCG monobutyrate and EGCG dibutyrate had the strongest inhibitory effect.

[0116] 2.2 Effect of EGCG esterification products on CML content in the simulation system

[0117] The results are shown in Table 6.

[0118] Table 6 Inhibition rate of EGCG and its esterification products on CML in the simulation system (P<0.05)

[0119]

[0120] EGCG and its esterification products all showed inhibitory effects on CML production, among which EGCG monobutyrate and EGCG dibutyrate had the strongest inhibitory effects.

[0121] 2.3 Effect of EGCG esterification products on CEL content in the simulation system

[0122] The results are shown in Table 7.

[0123] Table 7 Inhibition rate of EGCG and its esterification products on CEL in the simulation system (P<0.05)

[0124]

[0125] EGCG and its esterification products all showed inhibitory effects on CEL production, among which EGCG monobutyrate and EGCG dibutyrate had the strongest inhibitory effects.

[0126] The above-mentioned embodiments only express several implementation methods of the present invention, and the descriptions thereof are relatively specific and detailed, but they cannot be understood as limiting the scope of the invention patent. It should be pointed out that, for ordinary technicians in this field, several variations and improvements can be made without departing from the concept of the present invention, and these all belong to the protection scope of the present invention. Therefore, the protection scope of the patent of the present invention shall be subject to the attached claims.

Claims

1. A method for preparing cookies, characterized in that: The method comprises adding an EGCG esterification product into cookies; the EGCG esterification product is formed by esterification of EGCG and fatty acid chloride.

2. The preparation method according to claim 1, characterized in that: The fatty acyl chloride is butyryl chloride, which can be n-butyryl chloride.

3. The preparation method according to claim 1, characterized in that: The EGCG esterification product is EGCG monobutyrate or EGCG dibutyrate or a mixture of the two generated by a substitution reaction between EGCG and n-butyryl chloride.

4. The preparation method according to any one of claims 1 to 3, characterized in that: The esterification reaction time of EGCG and fatty acid chloride is 1-2 hours, preferably 1.5 hours; the reaction temperature is 40-50°C, preferably 45°C.

5. The preparation method according to any one of claims 1 to 4, characterized in that: Based on the total weight of the cookies, the content of the EGCG esterification product in the cookies is 0.01wt%-0.30wt%, preferably 0.25wt%.

6. The preparation method according to any one of claims 1 to 5, characterized in that: include: The EGCG esterification product is mixed with shortening and then mixed with other ingredients to prepare dough, and then cookies are prepared.

7. Cookies prepared by the method according to any one of claims 1 to 6.

8. Application of EGCG esterification products in the preparation of cookies; wherein, The EGCG esterification product is the same as the EGCG esterification product according to any one of claims 1-4.

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