CN115337334A - Application of rosemary alcohol extract in inhibiting AGEs (advanced glycation end products) induced by Methylglyoxal (MGO) - Google Patents
Application of rosemary alcohol extract in inhibiting AGEs (advanced glycation end products) induced by Methylglyoxal (MGO) Download PDFInfo
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Abstract
The invention discloses application of a rosemary alcohol extract in inhibiting AGEs (advanced glycation end products) induced by Methylglyoxal (MGO). MGO is an intermediate product of late glycosylation with direct cytotoxicity. The invention utilizes whey protein isolate and MGO to establish a system, rosemary extract is added into the system, and the influence of AGEs generation on the physicochemical and functional characteristics of the whey protein isolate and the inhibition effect of the rosemary extract on AGEs generation are researched by measuring the structure and function of the whey protein isolate. Therefore, a novel AGEs inhibitor can be developed.
Description
Technical Field
The invention belongs to the technical field of AGEs (advanced glycation end products) inhibitor preparation, and relates to application of a rosemary alcohol extract in inhibiting AGEs (advanced glycation end products) induced by Methylglyoxal (MGO).
Background
Glycosylation (glycosylation) is a key post-translational modification of proteins, and its abnormalities are closely related to pathological processes such as tumorigenesis and inflammatory response, which are involved in various cell biological processes. Advanced Glycation End Products (AGEs) are a general term for a series of irreversible, highly active End Products formed by non-enzymatic glycosylation reactions between the amino groups of proteins, fatty acids or nucleic acids and the aldehyde or ketone groups of reducing sugars, mainly generated by maillard reactions, fat oxidation reactions or polyol degradation pathways. Wherein the Maillard reaction is formed by three steps: first, the aldehyde group of reducing sugars (glucose, pentose, xylose, ribose, etc.) and the amino group of amino acids, polypeptides and proteins form schroff (schiff) by affinity addition reaction under non-enzymatic conditions; unstable schumarine forms stable amadori products (also called early glycosylation products) through rearrangement reaction, and can form a series of unsaturated aldone compounds through dehydrogenation, oxidation and rearrangement reaction, i.e. high activity advanced glycosylation intermediate products (AGIs), such as Methylglyoxal (MGO) which is an intermediate product of CEL formation, etc.; the active unsaturated aldehyde ketone compounds can react with free amino groups and sulfhydryl groups of proteins, amino acids and the like to generate AGEs, so that the AGEs are compounds with complex structures. The Maillard pathway is the most main pathway for forming AGEs in food, and researches show that the level of AGEs in serum of a human body can be increased by taking food-derived AGEs, the food-derived AGEs can be combined with and damage cells of body tissues, so that the aging speed of the human body is accelerated, and further, the occurrence of a plurality of chronic diseases such as diabetes, cardiovascular diseases, cancer, inflammation, atherosclerosis, glomerular sclerosis and the like is initiated or accelerated, and a series of oxidative stress grade combined reactions and inflammatory reactions can be caused by the accumulation of AGEs in the body. Therefore, AGEs in the food have great toxic effect on human bodies, and the reduction of the content of AGEs in the bodies has important significance on human health.
Researchers have studied how to inhibit AGEs, and there are three current approaches: the first is an AGE artificial synthesis inhibitor, such as aminoguanidine, which is a synthetic compound used for treating chronic diseases such as diabetes, and researches show that the aminoguanidine can effectively reduce the formation of AGE, and inhibits the formation of AGE by reacting with glycosylation intermediate products and generating inactive substances through carbonyl reaction; the second is natural inhibitors, including polyphenols (phenolic acids, flavonoids and stilbenes), mostly derived from medicinal and edible plants, previous studies have shown that chlorogenic acid can inhibit AGEs formation, it mainly acts at the stage of conversion of amadori products to glycosylation end products, the effect can reach the same level as standard anti-glycosylation aminoguanidine agents, and curcumin has antioxidant and anti-inflammatory effects, has therapeutic effect on chronic diseases such as diabetes, and mainly inhibits the accumulation of AGEs by two means: scavenging ability and antioxidant ability against Methylglyoxal (MGO); finally, RAGE blockers may be used to inhibit AGEs. Although the artificially synthesized inhibitor has good anti-glycation performance, clinical toxic and side effects of the artificially synthesized inhibitor are a potential threat, for example, metformin, which is used as a main medicament for clinically treating type 2 diabetes, can inhibit glycosylation reaction, but may cause liver and kidney injury after long-term application. Among the marketed AGEs inhibitors, a safe and easily available natural product having a high inhibitory activity, which can reduce the formation of harmful products and the accumulation of AGEs, thereby reducing and preventing the risk of diseases such as diabetic complications, is desirable.
Therefore, with the development of research, it is expected that more methods for preventing and treating diseases will be provided in order to develop safer and more effective drugs, such as AGEs inhibitors extracted from natural materials, or to become a new direction. At present, AGEs inhibitors are mostly artificially synthesized inhibitors, and have good effect but strong clinical toxic and side effects. Researches show that the antioxidant active ingredients can effectively inhibit the formation of AGEs in the food processing process, so that the ingestion of food-derived AGEs is reduced, and therefore, natural substances with the antioxidant active ingredients are important for researches.
Methylglyoxal MGO also known as methylglyoxal, molecular formula C 3 H 4 O 2 It contains two carboxyl functional groups, is very active in chemical property, and is a main precursor of non-fluorescent AGEs. MGO can be produced by human tissue and cell metabolism, or by food processing, and can be ingested by the dietAnd (4) internal accumulation. MGO has direct cytotoxicity, induces nucleic acid and protein to generate non-enzymatic carbonylation reaction to change functions and structures of DNA and protein, induces organism to generate inflammation and oxidative stress reaction to cause apoptosis and tissue injury, so that the MGO has close connection with development of chronic diseases such as diabetes and complications thereof, malignant tumor, cardiovascular disease, metabolic syndrome, neurodegenerative disease and the like, and the MGO can be used as reference to research the effect of rosemary alcohol extract on AGEs generation.
Disclosure of Invention
In view of the deficiencies of the prior art, it is a first object of the present invention to provide a use of rosemary alcohol extracts for inhibiting methylglyoxal, MGO, induced glycosylation end products AGEs.
The preparation process of the rosemary alcohol extract comprises the following steps:
after being dried and crushed, rosemary is placed in an extraction container, ethanol is added, and reflux extraction is carried out twice for 1-2 hours each time; mixing the two extractive solutions, recovering ethanol, concentrating to obtain paste, drying, and pulverizing into fine powder to obtain rosemary alcohol extract; wherein the volume ratio of the air-dried and crushed rosemary to the ethanol is 1.
Preferably, the extraction time per reflux is 1 hour.
Preferably, the volume ratio of the air-dried and crushed rosemary to the ethanol is 1.
Preferably, the volume fraction of ethanol is 95%.
The second purpose of the invention is to provide an inhibitor of AGEs (advanced glycation end products) induced by Methylglyoxal (MGO), which comprises rosemary alcohol extract.
Compared with the prior art, the invention has the beneficial effects that:
the invention provides a rosemary alcohol extract which is a natural substance and has antioxidant active ingredients, which can reduce glycosylation reaction of protein and remarkably inhibit AGEs in a system after MGO treatment, thereby playing roles in protecting protein and reducing the content of AGEs in a human body. Compared with the common artificially synthesized inhibitor, the novel AGEs inhibitor provided by the invention reduces clinical toxic and side effects, is safer and more efficient, and widens the application field of rosemary.
Drawings
FIG. 1 shows the AGEs production results of each group in example 1.
FIG. 2 is the results for the thiol content of each group in example 2, where C: WPI; f: WPI + MGO; m 0.5 : 500ppm of WPI, MGO and rosemary alcohol extract; m 1 : 1000ppm of WPI + MGO + rosemary alcohol extract; m is a group of 2 : WPI + MGO + rosemary alcohol extract 2000ppm.
FIG. 3 is the tryptophan fluorescence intensity for each group in example 3, wherein C: WPI; f: WPI + MGO; m 0.5 : 500ppm of WPI, MGO and rosemary alcohol extract; m 1 : 1000ppm of WPI + MGO + rosemary alcohol extract; m 2 : WPI + MGO + rosemary alcohol extract 2000ppm.
FIG. 4 is the magnitude of the solubilities of the various groups of proteins of example 4, wherein C: WPI; f: WPI + MGO; m is a group of 0.5 : 500ppm of WPI, MGO and rosemary alcohol extract; m is a group of 1 : 1000ppm of WPI + MGO + rosemary alcohol extract; m is a group of 2 : WPI + MGO + rosemary alcohol extract 2000ppm.
FIG. 5 is the hydrophobicity of the groups of proteins in example 5, wherein C: WPI; f: WPI + MGO; m 0.5 : 500ppm of WPI, MGO and rosemary alcohol extract; m 1 : 1000ppm of WPI + MGO + rosemary alcohol extract; m 2 : WPI + MGO + rosemary alcohol extract 2000ppm.
FIG. 6 shows the results of protein concentration detection by SDS-PAGE in example 6, wherein C: WPI; f: WPI + MGO; m 0.5 : 500ppm of WPI, MGO and rosemary alcohol extract; m 1 : 1000ppm of WPI + MGO + rosemary alcohol extract; m is a group of 2 : WPI + MGO + rosemary alcohol extract 2000ppm.
Detailed Description
The present invention is further analyzed with reference to the following specific examples.
The invention establishes a glycosylation system by taking whey protein isolate as a protein model to research the harmful effect of the generation of AGEs on the physicochemical and functional characteristics of the whey protein isolate, adds rosemary extract into the system to research the cleaning effect of different concentration adding conditions of the rosemary extract on an AGEs intermediate product MGO and the protective effect on the damage of protein, and researches the influence of the generation of AGEs on the physicochemical and functional characteristics of the whey protein isolate and the inhibition effect of the rosemary extract on the generation of AGEs by measuring the structure and function of the whey protein isolate.
5mL systems are established, and 5 groups of samples are designed in total, namely a pure protein WPI group (group C), a WPI + MGO group (group F) and a WPI + MGO + rosemary alcohol extract 500ppm group (M) 0.5 Group), WPI + MGO + Rosmarinus officinalis alcohol extract 1000ppm group (M) 1 Group), WPI + MGO + Rosmarinus officinalis alcohol extract 2000ppm group (M) 2 Group), the components are grouped as follows:
group C: 2.5mL of a whey protein isolate solution having a mass concentration of 14mg/mL and 5mL of a total of 2.5mL of LPBS solution were used as blanks.
And F group: 2.5mL of whey protein isolate solution with a mass concentration of 14mg/mL, 0.5mL of methylglyoxal solution with a mass concentration of 25.6mg/mL, and 2mL of PBS solution, and 5mL in total, were used as a control group.
M 0.5 Group (2): 2.5mL whey protein isolate solution with mass concentration of 14mg/mL, 0.5mL methylglyoxal solution with mass concentration of 25.6mg/mL, 0.25mL rosemary alcohol extract with mass concentration of 10mg/mL, and 1.75mL PBS solution, wherein the total volume is 5mL.
M 1 Group (2): 2.5mL whey protein isolate solution with mass concentration of 14mg/mL, 0.5mL methylglyoxal solution with mass concentration of 25.6mg/mL, 0.5mL rosemary alcohol extract with mass concentration of 10mg/mL, and 1.5mL PBS solution, wherein the total volume is 5mL.
M 2 Group (2): 2.5mL whey protein isolate solution with mass concentration of 14mg/mL, 0.5mL methylglyoxal solution with mass concentration of 25.6mg/mL, 1mL rosemary alcohol extract with mass concentration of 10mg/mL, and 1mL PBS solution, wherein the total volume is 5mL.
Mixing the above materials, reacting in 75 deg.C constant temperature water bath for 2 hr, and freezing for storage. Three sets of replicates were set for each sample.
Example 1: effect of Rosemary alcohol extracts on AGEs production
To further confirm the effect of the rosemary extract on MGO treatment-induced protein glycosylation, fluorimetry was used to determine C, F, M 0.5 、M 1 、M 2 AGEs were produced in five whey protein isolate glycosylation systems.
Experimental results as shown in fig. 1, the AGEs content in the system significantly increased after MGO was added to WPI (P < 0.05), whereas the AGEs content significantly decreased after further addition of the rosemary extract to the system, and the fluorescence intensity of AGEs decreased with increasing concentration of rosemary extract (P < 0.05).
Example 2: effect of Rosemary alcohol extract on protein thiol content
50 μ l of C, F, M with a concentration of 7mg/mL were taken separately 0.5 、M 1 、M 2 Putting five groups of protein solutions to be detected into a 2mL centrifuge tube, adding 800 mu L of 8M urea-Tris, and then adding 100 mu L of DTNB; at the same time, a control group was prepared by adding 50. Mu.l of C, F, M at a concentration of 7mg/mL 0.5 、M 1 、M 2 Adding five groups of protein solutions to be detected into a 2mL centrifuge tube, and adding 800 mu L of 8M urea-Tris; setting a blank control, using Tris-Gly to replace protein solution as a reagent blank, fully shaking all samples, and standing for thirty minutes at room temperature in a dark place. After standing, 200. Mu.L of the supernatant was pipetted into an ELISA plate and the absorbance at 412nm was measured. Using molar extinction coefficient 13600M -1 cm -1 The total thiol content was calculated. The calculation formula is as follows:
wherein 0.625 is the liquid volume coefficient in the ELISA plate, 13600 is the molar extinction coefficient, 0.35 is the protein mass (mg), 0.95 is the liquid volume (mL), 1000000 is used for unit conversion, and the final unit is mmol/gpro.
The experimental results are shown in FIG. 2. Thiol modification of proteins is one of the important post-translational modifications of proteins, and is involved in various cell biological processes. The ability of AGEs to react with amino, sulfhydryl and guanidine functional groups in proteins has been indicated in previous literature reports, resulting in denaturation of the target protein. We can find that the amount of sulfhydryl groups in the system does not change significantly after the addition of MGO (P > 0.05), but that the amount of protein sulfhydryl groups in the system decreases significantly after the addition of rosemary alcohol extract and decreases with increasing concentration of rosemary alcohol extract (P < 0.05).
Example 3: influence of Rosemary alcohol extract on Tryptophan fluorescence intensity
Respectively taking 5mLC, F and M 0.5 、M 1 、M 2 Adding 5mL20% TCA reagent into five groups of protein liquid to be tested, and centrifuging at 10000g and 25 ℃ for 2min. Centrifuging, discarding supernatant, re-dissolving the precipitate with 5mL of 10mM PBS, dissolving, diluting to 1mg/mL, placing the diluted protein solution in an ELISA plate, and measuring by using an ELISA reader. The parameters were EX (excitation wavelength) at 295nm, EM range 300-400nm. The smoothing process selects the window point number 18 using Origin2018 to plot.
A decrease in the fluorescence of the protein's solid tryptophan is also indicative of its oxidation. Thus, we further examined the tryptophan fluorescence intensity of the protein, and the results are shown in FIG. 3. The tryptophan fluorescence intensity of the protein is reduced after the MGO is added, and the tryptophan fluorescence intensity is more obviously reduced after the rosemary alcohol extract is further added, and the tryptophan fluorescence intensity is dose-dependent with the concentration of the rosemary alcohol extract.
Example 4: effect of Rosemary alcohol extracts on protein solubility
The magnitude of protein solubility is influenced by conditions such as pH, ionic strength, temperature, solvent type, etc. To investigate the effect of rosemary alcohol extract on protein solubility, the solubility of whey protein was investigated using biuret reaction.
Respectively taking 300 mu LC, F and M 0.5 、M 1 、M 2 Centrifuging five groups of samples at the rotating speed of 5000rab for 15min, taking 100 mu L of supernatant, and respectively adding 400 mu L of biuret to wait for reaction for 30min; another 100. Mu.L sample was added with 400. Mu.L biuret respectively and the reaction was waited for 30min. After the reaction is finished, 200 mu L of liquid to be detected is put on an enzyme label plate, and the absorbance of the liquid is measured at the wavelength of 540 nm. Taking BSA as standard protein, dissolving in ddH2O to make a standard curve, calculating the protein concentration of each group of data before and after centrifugation by using the BSA standard curve, and finally obtaining the required protein solubility by a formula of 100% protein concentration after centrifugation/original liquid protein concentration(％)。
Results figure 4 shows that the solubility of the protein increases to some extent after MGO was added, but the solubility of the protein decreases significantly after further addition of the rosemary alcohol extract and is dose-dependent (P < 0.05) with the concentration of the rosemary alcohol extract.
Example 5: effect of Rosemary alcohol extract on protein surface hydrophobicity
The surface hydrophobicity characteristic is measured by using 8-anilino-1-naphthalene sodium sulfonate ANS as a fluorescent probe. C, F, M were mixed with PBS buffer (10mM, pH7.4) 0.5 、M 1 、M 2 The five histone samples were diluted to concentrations of 0.1, 0.2, 0.3, 0.4 and 0.5mg/mL, respectively. After 3. Mu.LANS reagent was injected into the microplate, 0.2mL of the diluted protein sample was added thereto. The fluorescence intensity of the sample was measured at an excitation wavelength of 365nm and an emission wavelength of 484 nm. And (4) determining the obtained data, and making a scatter diagram according to the concentration proportion, wherein the obtained slope is the protein surface hydrophobicity index.
The hydrophobicity of the protein is beneficial to the protein to fold inwards to form a secondary structure, further form a structural domain, a tertiary structure and the like, and ensure the stability of the protein. However, as shown in fig. 5, the hydrophobicity of the protein was significantly reduced after the addition of MGO, and the hydrophobicity of the protein was more significantly reduced after the further addition of the rosemary alcohol extract, and there was a certain correlation with the concentration of the added rosemary alcohol extract (P < 0.05).
Example 6: effect of Rosemary alcohol extracts on protein Secondary Structure
Determined by SDS-PAGE electrophoresis. Preparing 12% separation gel and concentrated gel, wherein the sample loading of Marker is 3 μ l, the sample loading of the rest each hole is 8 μ l, switching on the power supply to carry out SDS-polyacrylamide gel electrophoresis, firstly running 80V until the Marker exceeds the concentrated gel, and then switching to 120V. Carefully taking off the gel after electrophoresis, dyeing with Coomassie brilliant blue staining solution for 30min, taking out the gel, washing, immersing in destaining solution, placing on a shaking table for oscillation destaining, and destaining for two times. The first time is 1 hour, and the second time is 1.5 hours, until the decolored solution has no obvious color. The gel was removed and placed in a gel imager for photographic analysis.
The whey protein mainly comprises beta-lactoglobulin (beta-Lg), alpha-lactalbumin (alpha-La), bovine Serum Albumin (BSA) and immunoglobulin (IgG), and the four types of protein account for more than 95 percent of the total whey protein. The molecular weight of alpha-La in the lactalbumin is 14.147-14.175 ku, and the molecular weight is the minimum in the milk protein; the molecular weight of beta-Lg was approximately 18ku and the molecular weight of BSA was 66ku. We observed the protein level in each sample after SDS-PAGE using coomassie blue staining as shown in figure 6, which shows a lighter band with MGO addition and a darker band with further rosemary extract, with a darker and denser continuum in the high relative molecular mass region.
Example 7: effect of Rosmarinus officinalis alcohol extract on protein digestibility
Digestibility was determined by OPA method. C. F, M 0.5 、M 1 、M 2 Taking 2mL of each tube of the five groups of sample systems, adjusting the pH value to 1.5, standing at the constant temperature of 37 ℃ for 10min, taking out, adding 90 mu l of gastric enzyme, standing at 37 ℃, dividing the standing time into five time points, taking out 30 mu l of each tube, adding 600 mu l of OPA, keeping the temperature at 37 ℃ for 2min, and measuring the absorbance at 340 nm; after the second time point is 60min, taking out and repeating the operation of the first time point; then, after the pH value of the rest samples is adjusted to 7, 100 mu l of pancreatin is added, the mixture is placed at 37 ℃ for 30min, namely, the third time point-90 min, and the operation of the first time point is repeated; continuously keeping the temperature for 30min to a fourth time point-120 min, and repeating the operation of the first time point; and finally, continuously keeping the temperature for 60min to a fifth time point of-180 min, and repeating the operation of the first time point. The final result is the absorbance value of the sample at five time points, which is substituted into the serine standard curve to obtain the corresponding concentration, and the degree of hydrolysis DH can reflect the protein digestibility since the value is in direct proportion to the amount of free amino groups and hydrolyzed peptide bonds. The formula is as follows:
where 7 is the protein concentration (mg/mL), 30 is the volume of sample added (. Mu.l) and 8.8 is the amount of peptide bonds per kg of WPI (mol/kg). The results are shown in Table 1.
TABLE 1 changes in protein digestibility
The protein can be fully digested into amino acid and short peptide by human body is a big premise that the protein is absorbed by human body and then exerts various physiological functions, and the undigested protein can be fermented by intestinal bacteria to generate toxic and harmful metabolites. Thus, protein digestibility is an indicator of its nutritional value. Moreover, in previous studies it was pointed out that oxidation leads to a reduced digestibility of proteins. To clarify the effect of rosemary extract on protein digestibility, we used whey protein in the gastro-trypsin treatment system and found that protein digestibility was significantly reduced after MGO treatment, but increased again after further rosemary extract addition (P < 0.05).
Claims (9)
1. Application of rosemary alcohol extract in inhibiting AGEs (advanced glycation end products) induced by Methylglyoxal (MGO).
2. Use according to claim 1, wherein said rosemary alcohol extract is prepared as follows:
after being dried and crushed, the rosemary is placed in an extraction container, ethanol is added, and reflux extraction is carried out twice, wherein each time lasts for 1-2 hours; mixing the two extractive solutions, recovering ethanol, concentrating to obtain paste, drying, and pulverizing into fine powder to obtain rosemary alcohol extract; wherein the volume ratio of the air-dried and crushed rosemary to the ethanol is 1.
3. The use according to claim 2, wherein the extraction time per reflux is 1 hour.
4. Use according to claim 2, wherein the volume ratio of air-dried disintegrated rosemary to ethanol is 1.
5. Use according to claim 2, wherein the ethanol is present in a volume fraction of 95%.
6. An AGEs inhibitor induced by methylglyoxal MGO, which is characterized by comprising rosemary alcohol extract.
7. The methylglyoxal MGO-induced AGEs inhibitor according to claim 6, wherein said rosemary alcohol extract is prepared by the following process:
after being dried and crushed, the rosemary is placed in an extraction container, ethanol is added, and reflux extraction is carried out twice, wherein each time lasts for 1-2 hours; mixing the two extractive solutions, recovering ethanol, concentrating to obtain paste, drying, and pulverizing into fine powder to obtain rosemary alcohol extract; wherein the volume ratio of the air-dried and crushed rosemary to the ethanol is 1.
8. The methylglyoxal MGO-induced AGEs inhibitor according to claim 7, wherein the time for each reflux extraction is 1 hour, and the volume ratio of the air-dried disintegrated rosemary to ethanol is 1.
9. The methylglyoxal MGO-induced AGEs inhibitor according to claim 7, wherein said ethanol is present in a 95% volume fraction.
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| CN102286059A (en) * | 2011-09-08 | 2011-12-21 | 南京泽朗医药科技有限公司 | Method for extracting ursolic acid, carnosic acid and rosmarinic acid from rosmarinus officinalis |
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