CN111991560A - Method for enhancing light stability of isoorientin and application thereof - Google Patents
Method for enhancing light stability of isoorientin and application thereof Download PDFInfo
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- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/02—Inorganic compounds
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
- A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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- B22F9/00—Making metallic powder or suspensions thereof
- B22F9/16—Making metallic powder or suspensions thereof using chemical processes
- B22F9/18—Making metallic powder or suspensions thereof using chemical processes with reduction of metal compounds
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y40/00—Manufacture or treatment of nanostructures
Abstract
The invention provides a method for enhancing the light stability of isoorientin and application thereof, belonging to the technical field of chemical material performance improvement.
Description
Technical Field
The invention belongs to the technical field of chemical material performance improvement, relates to improvement of isoorientin performance, and particularly relates to a method for enhancing the light stability of isoorientin and application of the isoorientin.
Background
Isoorientin is isoorientin IA tetrahydroxyflavone compound, also called 3 ', 4', 5, 7-tetrahydroxyflavone-6-O-beta-D-glucopyranoside or luteolin 6-C-glucoside, has molecular formula of C21H2OO11Molecular weight is 448.38, and its chemical structural formula is shown in FIG. 1. The isoorientin solid is light yellow powder, the steam density is 15.48, and the melting point/freezing point is 237-239 ℃. It is widely used in food such as cucumber, buckwheat, passion flower, etc., and has antioxidant, antiinflammatory, antibacterial, hepatoprotective, and intestinal flora regulating effects. But the isoorientin has limited application due to the performance of isoorientin, such as:
1. isoorientin is extremely unstable and can be easily photolyzed, and the biological activity of isoorientin is greatly reduced in a bright environment, so that the application of isoorientin in the pharmaceutical industry is limited;
2. the isoorientin is difficult to be absorbed by human bodies due to poor water solubility, and the application of the isoorientin in the food industry is limited.
Disclosure of Invention
Aiming at the problems of extremely unstable isoorientin, easy photolysis, poor water solubility and the like, the invention provides a method for enhancing the light stability of isoorientin and application thereof, the prepared isoorientin-silver nanoparticle compound has good biological safety, can better inhibit the activity of alpha-glucosidase and pancreatic lipase, and has the effect of preventing diabetes and obesity, and the specific technical scheme is as follows:
the method for enhancing the light stability of isoorientin is characterized in that dispersed silver nanoparticles are used as carriers, so that isoorientin is attached to the surfaces of the silver nanoparticles to form an isoorientin-silver nanoparticle compound with good light stability.
The preparation method of the isoorientin-silver nanoparticle compound comprises the following steps:
1) mixing a corn starch water solution, a silver nitrate water solution and a sodium citrate water solution according to a volume ratio of 20-60: 50-99: 3-8, reacting in a water bath, stirring, centrifuging, and drying the centrifuged precipitate to obtain silver nanoparticles;
2) dispersing the silver nanoparticles obtained in the step 1) with ultrapure water, adding the dispersion into the isoorientin solution, stirring under a water bath condition, cooling, centrifuging, and drying the centrifuged precipitate to obtain the isoorientin-silver nanoparticle compound.
Further limiting, the mass concentration of the corn starch aqueous solution is 1-3%, the molar concentration of the silver nitrate aqueous solution is 1-2 mM, and the molar concentration of the sodium citrate aqueous solution is 0.01-0.03 mol/L.
Further limiting, the temperature of the water bath reaction in the step 1) is 60-80 ℃.
Further limiting, the mass concentration of the isoorientin solution in the step 2) is 0.1-2 mg/mL.
Further limiting, the temperature of the water bath in the step 2) is 20-40 ℃.
The isoorientin-silver nanoparticle complex prepared by the preparation method of the isoorientin-silver nanoparticle complex.
The isoorientin-silver nanoparticle complex is applied to inhibiting cytotoxicity.
The isoorientin-silver nanoparticle complex is applied to the aspect of inhibiting the activity of alpha-glucosidase.
The isoorientin-silver nanoparticle complex is applied to the inhibition of pancreatic lipase activity.
Compared with the prior art, the invention has the beneficial effects that:
1. according to the method for enhancing the light stability of isoorientin, isoorientin is attached to the surfaces of silver nanoparticles to form the silver nanoparticles loaded with the isoorientin, namely the isoorientin-silver nanoparticle complex is formed, the isoorientin-silver nanoparticle complex still contains 98.4% of isoorientin after being irradiated by an ultraviolet lamp for 1 hour, and compared with the pure isoorientin, the stability of the isoorientin is greatly improved.
2. The isoorientin-silver nanoparticle compound prepared by the invention is simple in preparation process, and the isoorientin-silver nanoparticle compound can well inhibit cytotoxicity and has good biological safety; meanwhile, the isoorientin-silver nanoparticle compound can inhibit the activities of alpha-glucosidase and pancreatic lipase, increases the water solubility of isoorientin, is easier to absorb by a human body, enables the inhibition rate of the isoorientin on the activities of the alpha-glucosidase and the pancreatic lipase to be not less than 57% and 19.4%, can play roles in preventing diabetes and obesity, and can be better applied to the pharmaceutical industry and the food industry.
Drawings
FIG. 1 shows the chemical structural formula of isoorientin;
fig. 2 is an ultraviolet absorption spectrum of isoorientin and isoorientin-silver nanoparticle complexes;
fig. 3 is a fourier infrared spectrum of isoorientin and isoorientin-silver nanoparticle complexes;
fig. 4 is a transmission electron microscope image of isoorientin and isoorientin-silver nanoparticle complexes;
fig. 5 is a photostability chart of isoorientin and isoorientin-silver nanoparticle complexes;
fig. 6 shows the action of isoorientin and isoorientin-silver nanoparticle complexes on human hepatocyte viability;
fig. 7 shows the effect of isoorientin and isoorientin-silver nanoparticle complexes on alpha-glucosidase activity;
fig. 8 shows the effect of isoorientin and isoorientin-silver nanoparticle complexes on pancreatic lipase activity.
Detailed Description
The technical solutions of the present invention will be further explained below with reference to the drawings and examples, but the present invention is not limited to the embodiments explained below.
The method for enhancing the light stability of isoorientin comprises the following steps: the method is characterized in that the isoorientin is attached to the surfaces of silver nanoparticles by using the dispersed silver nanoparticles as carriers to form the isoorientin-silver nanoparticle compound with good light stability.
The preparation method of the isoorientin-silver nanoparticle compound comprises the following steps:
1) mixing a corn starch water solution, a silver nitrate water solution and a sodium citrate water solution according to a volume ratio of 20-60: 50-99: 3-8, reacting in a water bath, stirring, centrifuging, and drying the centrifuged precipitate to obtain silver nanoparticles;
2) dispersing the silver nanoparticles obtained in the step 1) with ultrapure water, adding the dispersion into the isoorientin solution, stirring under a water bath condition, cooling, centrifuging, and drying the centrifuged precipitate to obtain the isoorientin-silver nanoparticle compound.
Preferably, the mass concentration of the corn starch aqueous solution is 1-3%, the molar concentration of the silver nitrate aqueous solution is 1-2 mM, and the molar concentration of the sodium citrate aqueous solution is 0.01-0.03 mol/L.
Preferably, the temperature of the water bath reaction in the step 1) is 60-80 ℃.
Preferably, the mass concentration of the isoorientin solution in the step 2) is 0.1-2 mg/mL.
Preferably, the temperature of the water bath in the step 2) is 20-40 ℃.
The isoorientin-silver nanoparticle complex prepared by the preparation method of the isoorientin-silver nanoparticle complex.
The isoorientin-silver nanoparticle complex is applied to inhibiting cytotoxicity.
The isoorientin-silver nanoparticle complex is applied to the aspect of inhibiting the activity of alpha-glucosidase.
The isoorientin-silver nanoparticle complex is applied to the inhibition of pancreatic lipase activity.
Example 1
The preparation method of the isoorientin-silver nanoparticle compound comprises the following steps:
1) mixing a corn starch aqueous solution with the mass concentration of 2%, a silver nitrate aqueous solution with the molar concentration of 1.5mM and a sodium citrate aqueous solution with the molar concentration of 0.02mol/L according to the volume ratio of 30: 66: 4, performing water bath reaction at 70 ℃, stirring for 2 hours, centrifuging, and drying the centrifuged precipitate to obtain silver nanoparticles;
2) dispersing the silver nanoparticles prepared in the step 1 with ultrapure water, adding isoorientin solution with the volume of 6mL and the mass concentration of 1mg/mL, stirring for 30 hours under the condition of water bath at the temperature of 30 ℃, centrifuging for 30 minutes at the rotating speed of 10000rmp, and drying the centrifuged precipitate to obtain the isoorientin-silver nanoparticle compound.
Referring to fig. 2, the composite rate of the isoorientin-silver nanoparticle composite is 76.6% by calculation of ultraviolet spectrum.
Example 2
The preparation method of the isoorientin-silver nanoparticle compound comprises the following steps:
1) mixing a corn starch aqueous solution with the mass concentration of 1%, a silver nitrate aqueous solution with the molar concentration of 1mM and a sodium citrate aqueous solution with the molar concentration of 0.01mol/L according to the volume ratio of 60: 99: 8, performing water bath reaction at 60 ℃, stirring for 1 hour, centrifuging, and drying the centrifuged precipitate to obtain silver nanoparticles;
2) dispersing the silver nanoparticles prepared in the step 1 by using ultrapure water, adding isoorientin solution with the volume of 5mL and the mass concentration of 0.1mg/mL, stirring for 48 hours under the water bath condition of 20 ℃, centrifuging for 30 minutes at the rotating speed of 8000rmp, and drying the centrifuged precipitate to obtain the isoorientin-silver nanoparticle composite.
Example 3
The preparation method of the isoorientin-silver nanoparticle compound comprises the following steps:
1) mixing a corn starch aqueous solution with the mass concentration of 3%, a silver nitrate aqueous solution with the molar concentration of 2mM and a sodium citrate aqueous solution with the molar concentration of 0.03mol/L according to the volume ratio of 20: 50: 3, performing water bath reaction at 80 ℃, stirring for 3 hours, centrifuging, and drying the centrifuged precipitate to obtain silver nanoparticles;
2) dispersing the silver nanoparticles prepared in the step 1 with ultrapure water, adding isoorientin solution with the volume of 3mL and the mass concentration of 2mg/mL, stirring for 10 hours under the condition of water bath at 40 ℃, centrifuging for 30 minutes at the rotating speed of 12000rmp, and drying the centrifuged precipitate to obtain the isoorientin-silver nanoparticle compound.
To illustrate the performance of the isoorientin-silver nanoparticle complexes of the present invention, the following tests were performed:
test 1: structural performance index test
Experimental groups: isoorientin-silver nanoparticle complexes prepared in example 1
Control group: silver nanoparticles
Referring to FIG. 3, it can be seen that the IR spectrum of isoorientin and its composite is 3425.3cm-1And 2941.28cm-1Has unique peaks belonging to O-H and C-H groups of isoorientin, and peaks of C-O, C ═ C and aromatic C ═ C respectively appearing at 1641.33, 1446.27 and 1431.13cm-1To (3). The infrared spectrum of the isoorientin-silver nanoparticle complex shows that all representative peaks are at respective positions, and the absorbance changes slightly, so that the isoorientin is successfully loaded on the silver nanoparticles to form the isoorientin-silver nanoparticle complex.
Referring to fig. 4, it can be seen from transmission electron micrographs of isoorientin and isoorientin-silver nanoparticle complexes that the isoorientin-silver nanoparticle complexes are spherical particles. By comparison, it was found that the particle size of the silver nanoparticles was smaller than that of the isoorientin-silver nanoparticle complex particles under the same magnified visual field.
Test 2: photostability test of isoorientin-silver nanoparticle complexes
Experimental groups: isoorientin-silver nanoparticle complexes prepared in example 1
Control group: isoorientin
Referring to fig. 5, it can be seen from the light stability chart of isoorientin and the isoorientin-silver nanoparticle complexes that the concentration of isoorientin is gradually reduced along with the extension of the irradiation time of the ultraviolet lamp, and after the irradiation time is 1 hour, the concentration of isoorientin is only 78.1%, but the concentration of isoorientin in the isoorientin-silver nanoparticle complexes is still 98.4%, and the concentration is almost not changed, which indicates that the isoorientin-silver nanoparticle complexes are not easily photolyzed, i.e., the isoorientin-silver nanoparticle complexes have stronger light stability, and can better maintain the functional activity of isoorientin.
Test 3: biological safety test of isoorientin-silver nanoparticle complex
Experimental groups: isoorientin-silver nanoparticle complexes prepared in example 1
Control group: isoorientin
The cell activity of the isoorientin-silver nanoparticle complex on HL-7702 human liver cells is determined by adopting an MTT staining method.
Referring to fig. 6, the isoorientin and the isoorientin-silver nanoparticle complex have the effect on the activity of human hepatocytes, after the isoorientin and the isoorientin-silver nanoparticle complex with the same concentration are respectively applied to the hepatic cells of the HL-7702, the cell activity of the hepatic cells of the HL-7702 is 132.18%, and after the isoorientin is applied, the cell activity of the hepatic cells of the HL-7702 is 103.87%, which indicates that the isoorientin-silver nanoparticle complex has no influence on the cell activity of the hepatic cells of the HL-7702, i.e., the isoorientin-silver nanoparticle complex does not generate toxicity to the hepatic cells of the HL-7702, and has good biological safety.
The same test method is used for measuring human pancreatic cells, human myocardial cells and human stem cells, the conclusion that the human pancreatic cells, the human myocardial cells and the human stem cells are the same as the human liver cells is obtained, and the isoorientin-silver nanoparticle compound prepared by the invention can well inhibit cytotoxicity and has good biological safety.
Test 4: test for inhibiting activity of alpha-glucosidase by isoorientin-silver nanoparticle complex
Experimental groups: isoorientin-silver nanoparticle complexes prepared in example 1
Control group: isoorientin
Alpha-glucosidase is a membrane-bound enzyme that breaks down carbohydrates in food into glucose, but large amounts of glucose accumulate in the blood leading to diabetes. Therefore, if the activity of alpha-glucosidase is inhibited, diabetes can be prevented.
Mixing 80 μ L of isoorientin-silver nanoparticle complex solution of 60 μ g/mL, 80 μ L of isoorientin-silver nanoparticle complex solution of 90 μ g/mL, 80 μ L of isoorientin-silver nanoparticle complex solution of 120 μ g/mL, 80 μ L of isoorientin solution of 60 μ g/mL, 80 μ L of isoorientin solution of 90 μ g/mL, and 80 μ L of isoorientin solution of 60 μ g/mLAdding mL isoorientin solution, 80 μ L, and 120 μ g/mL isoorientin solution into 6 parts of glucosidase solution containing 20 μ L and 20 μ g/mL phosphate buffer solution, respectively, incubating at 37 deg.C for 5min, adding 100 μ L and 4mM phosphate buffer solution containing 4-nitrophenyl- β -D-glucopyranoside, incubating at 37 deg.C for 30min, adding 100 μ L and 4mM Na2CO3The solution stops the reaction. The absorbance is measured at 412nm by using a microplate reader, and the alpha-glucosidase inhibition rate is calculated according to the following formula:
α -glucosidase inhibition (%) 100- (sample absorbance/blank absorbance × 100)
As can be seen from fig. 7, the inhibition rate of the isoorientin-silver nanoparticle complex on alpha-glucosidase is obviously increased with the increase of the concentration, and when the concentration is 120 μ g/mL, the inhibition rate of the isoorientin-silver nanoparticle complex on alpha-glucosidase is 57%, and the inhibition rate of the isoorientin on alpha-glucosidase is 51%.
Therefore, the isoorientin-silver nanoparticle complex has stronger inhibition capability on the activity of the alpha-glucosidase than isoorientin.
Test 5: test for inhibiting pancreatic lipase activity by isoorientin-silver nanoparticle complex
Experimental groups: isoorientin-silver nanoparticle complexes prepared in example 1
Control group: isoorientin
Pancreatic lipase is an important gastrointestinal enzyme that hydrolyzes triacylglycerols to glycerol and fatty acids, resulting in obesity. Therefore, obesity can be prevented if the activity of pancreatic lipase is inhibited.
Dissolving 5.0mg/mL of pancreatic lipase in 1M tris (hydroxymethyl) aminomethane buffer solution with a pH of 8.5, dissolving 4-nitrophenyl caprylate substrate with dimethyl sulfoxide, diluting with 5.0mM ethanol to prepare a pancreatic lipase solution, adding 100.0mac L of isoorientin-silver nanoparticle complex solution of 8. mu.g/mL, 100.0mac L of isoorientin-silver nanoparticle complex solution of 10. mu.g/mL, 100.0mac L of isoorientin-silver nanoparticle complex solution of 20. mu.g/mL, 100.0mac L of isoorientin-silver nanoparticle complex solution of 8. mu.g/mL, 100.0mac L of isoorientin solution of 10. mu.g/mL, 100.0mac L of isoorientin solution of 20. mu.g/mL, and 20. mu.g/mL of isoorientin solution to 6 parts of 100.0mac L of pancreatic lipase solution, incubating at 37 ℃ for 25min, adding 100.0 mol/L4-nitrophenyl caprylate, incubating at 37 deg.C for 25min, and measuring absorbance at 412nm with microplate reader. The pancreatic lipase inhibition rate was calculated as follows:
pancreatic lipase inhibition (%) 100- (sample absorbance/blank absorbance × 100)
As can be seen with reference to figure 8,
with the increase of the concentration, the inhibition rate of the isoorientin-silver nanoparticle complex on pancreatic lipase is obviously increased, and when the concentration is 20 mug/mL, the inhibition rate of the isoorientin-silver nanoparticle complex on pancreatic lipase is 19.4%, and the inhibition rate of isoorientin on pancreatic lipase is 11.4%.
Therefore, the isoorientin-silver nanoparticle complex has stronger inhibition capability on pancreatic lipase activity than isoorientin.
Therefore, the isoorientin-silver nanoparticle complex can be used for inhibiting cytotoxicity, has an obvious inhibition effect on the cytotoxicity and has good biological safety; can also be used for inhibiting the activity of alpha-glucosidase and pancreatic lipase, the inhibition rates of the activity of the alpha-glucosidase and the pancreatic lipase are not less than 57 percent and 19.4 percent respectively, the effects of preventing diabetes and obesity can be achieved, and the preparation method is better applied to the fields of medicine and food.
Claims (10)
1. The method for enhancing the light stability of isoorientin is characterized in that the method is to use dispersed silver nanoparticles as carriers to enable the isoorientin to be attached to the surfaces of the silver nanoparticles to form the isoorientin-silver nanoparticle compound with good light stability.
2. The preparation method of the isoorientin-silver nanoparticle compound is characterized by comprising the following steps of:
1) mixing a corn starch water solution, a silver nitrate water solution and a sodium citrate water solution according to a volume ratio of 20-60: 50-99: 3-8, reacting in a water bath, stirring, centrifuging, and drying the centrifuged precipitate to obtain silver nanoparticles;
2) dispersing the silver nanoparticles obtained in the step 1) with ultrapure water, adding the dispersion into the isoorientin solution, stirring under a water bath condition, cooling, centrifuging, and drying the centrifuged precipitate to obtain the isoorientin-silver nanoparticle compound.
3. The method for preparing the isoorientin-silver nanoparticle compound according to claim 2, wherein the mass concentration of the corn starch aqueous solution is 1-3%, the molar concentration of the silver nitrate aqueous solution is 1-2 mM, and the molar concentration of the sodium citrate aqueous solution is 0.01-0.03 mol/L.
4. The method for preparing the isoorientin-silver nanoparticle complex according to claim 3, wherein the temperature of the water bath reaction in the step 1) is 60-80 ℃.
5. The method for preparing the isoorientin-silver nanoparticle complex according to claim 2, wherein the mass concentration of the isoorientin solution in the step 2) is 0.1-2 mg/mL.
6. The method for preparing the isoorientin-silver nanoparticle composite according to claim 5, wherein the water bath temperature in the step 2) is 20-40 ℃.
7. The isoorientin-silver nanoparticle complex prepared by the method for preparing the isoorientin-silver nanoparticle complex according to claim 2.
8. The use of the isoorientin-silver nanoparticle complex of claim 7 for inhibiting cytotoxicity.
9. The use of the isoorientin-silver nanoparticle complex of claim 7 for inhibiting the activity of α -glucosidase.
10. The use of the isoorientin-silver nanoparticle complex of claim 7 for inhibiting pancreatic lipase activity.
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| CN116076512A (en) * | 2023-03-16 | 2023-05-09 | 云南省农业科学院生物技术与种质资源研究所 | Application of isoorientin compound |
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| AU2018101555A4 (en) * | 2017-12-15 | 2018-11-29 | Northwest Institute Of Plateau Biology, Chinese Academy Of Sciences | Application of isoorientin in the preparation of insulin-resistant related diseases |
| CN110179998A (en) * | 2019-06-06 | 2019-08-30 | 中国科学院长春应用化学研究所 | A kind of nano particle, preparation method and application |
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| AU2018101555A4 (en) * | 2017-12-15 | 2018-11-29 | Northwest Institute Of Plateau Biology, Chinese Academy Of Sciences | Application of isoorientin in the preparation of insulin-resistant related diseases |
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| CN116076512A (en) * | 2023-03-16 | 2023-05-09 | 云南省农业科学院生物技术与种质资源研究所 | Application of isoorientin compound |
| CN116076512B (en) * | 2023-03-16 | 2023-06-02 | 云南省农业科学院生物技术与种质资源研究所 | Application of isoorientin compound |
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