CN108743607B - Tea saponin selenium complex, tea saponin selenium nanoparticles, and preparation method and application thereof - Google Patents
Tea saponin selenium complex, tea saponin selenium nanoparticles, and preparation method and application thereof Download PDFInfo
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K33/00—Medicinal preparations containing inorganic active ingredients
- A61K33/04—Sulfur, selenium or tellurium; Compounds thereof
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0053—Mouth and digestive tract, i.e. intraoral and peroral administration
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
- A61P39/06—Free radical scavengers or antioxidants
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/321—Polymers modified by chemical after-treatment with inorganic compounds
- C08G65/328—Polymers modified by chemical after-treatment with inorganic compounds containing other elements
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/331—Polymers modified by chemical after-treatment with organic compounds containing oxygen
- C08G65/332—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing carboxyl groups, or halides, or esters thereof
- C08G65/3324—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing carboxyl groups, or halides, or esters thereof cyclic
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/338—Polymers modified by chemical after-treatment with inorganic and organic compounds
Abstract
The invention discloses a tea saponin selenium complex, which structurally consists of 2 molecules of tea saponin, 1 selenium atom and 2 molecules of polyethylene glycol. The invention also discloses a theasaponin selenium nanoparticle containing the theasaponin selenium complex, which comprises the following components in percentage by weight: (1) dissolving theasaponin in water, adding glucoamylase, and keeping the temperature at 35-55 ℃ for 4-12 h; standing for layering, and collecting precipitate; (2) dissolving the precipitate with an ethanol water solution, adding a selenium dioxide ethanol solution with the mass of 2-5% of the precipitate and 5-20% of polyethylene glycol, and reacting at 60-70 ℃ for 6-8 h; (3) concentrating under reduced pressure to evaporate ethanol, filtering with 0.22-0.45 μm filter membrane, and freeze drying. Meanwhile, the invention also discloses theasaponin selenium nanoparticles and application thereof. The theasaponin selenium complex can effectively reduce the biotoxicity of inorganic selenium, exert the synergistic effect of theasaponin and selenium, improve the antioxidant and free radical scavenging capabilities, and can be used for preparing anti-aging medicaments.
Description
Technical Field
The invention relates to application of tea saponin, in particular to a tea saponin selenium complex, tea saponin selenium nanoparticles, and a preparation method and application thereof.
Background
During the metabolism process of human body, due to charge transfer, covalent bonds in compound molecules are continuously subjected to homolytic cleavage, so that outer orbitals have unpaired electrons, thereby generating free radicals such as hydroxyl radical (. OH) and superoxide anion radical (O)2 -Cndot.). Free radicals generated in the body have strong oxidizing property, and excessive free radicals seriously damage tissues and cells of the body, thereby causing chronic diseases and aging. The natural product contains rich saponin, flavone, polysaccharide and other components, and has the function of eliminating free radicals in vitro, but most of the components are poor and unstable in organism absorption and have poor in vivo activity effect.
The tea saponin is a main pentacyclic triterpene compound in tea seeds and consists of a sugar body, a ligand and an organic acid. The tea saponin has strong oxidation resistance and can better eliminate active oxygen free radicals, thereby having the anti-aging effect. However, the tea saponin has large molecular weight, is not easy to absorb, is easy to degrade in vivo and has poor stability.
Selenium is a trace element necessary for human bodies, is an important component of glutathione peroxidase and selenium-P protein in the human bodies, and plays a role in balancing oxidation-reduction potential states in the human bodies, so the selenium has certain oxidation resistance and anti-aging effects. Compared with inorganic selenium, the organic selenium has the characteristics of higher bioavailability and bioactivity, lower biotoxicity and the like, but the natural organic selenium compounds are very few.
Disclosure of Invention
In order to overcome the defects in the prior art, the invention aims to provide the theasaponin selenium complex, which can effectively reduce the biotoxicity of inorganic selenium, play the synergistic effect of theasaponin and selenium and improve the oxidation resistance and free radical scavenging capacity.
The invention also aims to provide the theasaponin selenium nanoparticles containing the theasaponin selenium complex, which have the advantages of good water solubility, easy absorption and high bioavailability.
The invention also aims to provide the preparation method of the theasaponin selenium nanoparticles, which has the advantages of simple preparation process, mild reaction conditions and convenience for industrial production.
The fourth purpose of the invention is to provide the application of the theasaponin selenium nanoparticles.
The purpose of the invention is realized by the following technical scheme:
a theasaponin selenium complex has the following structure:
wherein n is 3 to 50.
A method for preparing theasaponin selenium nanoparticles comprising the theasaponin selenium complex of claim 1, comprising the steps of:
(1) dissolving theasaponin in water with the mass 15-30 times that of theasaponin, adding glucoamylase, and keeping the temperature at 35-55 ℃ for 4-12 hours; standing for layering, and collecting precipitate;
(2) dissolving the precipitate with an ethanol water solution, adding a selenium dioxide ethanol solution with the mass of 2-5% of the precipitate and 5-20% of polyethylene glycol, and reacting at 60-70 ℃ for 6-8 h;
(3) concentrating under reduced pressure to evaporate ethanol, filtering with a filter membrane of 0.22-0.45 μm, and freeze-drying to obtain theasaponin selenium nanoparticles.
The addition amount of the glucoamylase in the step (1) is that 500-5000U of glucoamylase is added to every 100g of theasaponin.
The volume fraction of the ethanol water solution in the step (2) is 70-85%, and the addition amount of the ethanol water solution is 10-20 mL/g of the liquid-solid ratio of the ethanol water solution to the precipitate.
The molecular weight of the polyethylene glycol in the step (2) is 400-6500 Da.
The selenium dioxide ethanol solution comprises 10-20% by mass.
And (3) carrying out reduced pressure concentration for 1-3 h under the conditions of 0.01-0.1 MPa, 50-70 ℃.
The theasaponin selenium nano-particles prepared by the preparation method of the theasaponin selenium nano-particles.
The theasaponin selenium nano-particles are applied to preparing anti-aging medicaments for eliminating in-vivo free radicals.
The anti-aging drug is in an oral or injection dosage form.
Compared with the prior art, the invention has the following advantages and beneficial effects:
(1) the invention hydrolyzes the tea saponin by a biological enzyme method to obtain the saponin with small molecular weight and removed glycosyl, so that the biological activity of the saponin is further enhanced.
(2) The theasaponin organic selenium can effectively reduce the biotoxicity of inorganic selenium, exert the synergistic effect of the theasaponin and the selenium and improve the oxidation resistance and the free radical scavenging capacity.
(3) The tea saponin organic selenium nano-particles have good water solubility, easy absorption and high bioavailability.
(4) The preparation process is simple, the reaction condition is mild, and the industrial production is convenient.
Detailed Description
The present invention will be described in further detail with reference to examples, but the embodiments of the present invention are not limited thereto.
Example 1
(1) Dissolving 1kg of theasaponin in 15kg of water, adding glucoamylase with activity unit of 5000U, and keeping the temperature at 35 deg.C for 12 hr; standing for layering, and collecting precipitate;
(2) dissolving 100g of precipitate with 1L of 70% ethanol water solution, adding 2g of 20% selenium dioxide ethanol solution and 5g of polyethylene glycol (1200Da, n is approximately equal to 9), and reacting at 60 ℃ for 8 h;
(3) concentrating under reduced pressure at 70 deg.C under 0.1MPa for 1 hr to remove ethanol, filtering with 0.22 μm filter membrane, and freeze drying to obtain 105g theasaponin selenium nanoparticles.
Example 2
(1) Dissolving 1kg of theasaponin in 30kg of water, adding active unit 50000U of glucoamylase, and keeping the temperature at 55 deg.C for 4 hr; standing for layering, and collecting precipitate;
(2) dissolving 100g of precipitate with 2L of 85% ethanol water solution, adding 5g of 10% selenium dioxide ethanol solution and 20g of polyethylene glycol (650Da, n is approximately equal to 5), and reacting at 60 ℃ for 6 h;
(3) concentrating under reduced pressure at 50 deg.C under 0.01MPa for 3 hr to remove ethanol, filtering with 0.45 μm filter membrane, and freeze drying to obtain 119g theasaponin selenium nanoparticles.
Example 3
(1) Dissolving 1kg of theasaponin in 20kg of water, adding 10000U of glucoamylase with activity unit, and keeping the temperature at 45 deg.C for 6 h; standing for layering, and collecting precipitate;
(2) dissolving 100g of precipitate with 1.5L of ethanol water solution with volume fraction of 75%, adding 3g of selenium dioxide ethanol solution with mass fraction of 15% and 10g of polyethylene glycol (2000Da, n is approximately equal to 15), and carrying out reflux reaction at 65 ℃ for 7 h;
(3) concentrating under reduced pressure at 60 deg.C under 0.05MPa for 2 hr to remove ethanol, filtering with 0.35 μm filter membrane, and freeze drying to obtain 108g theasaponin selenium nanoparticles.
Example 4
(1) Dissolving 1kg of theasaponin in 16kg of water, adding glucoamylase with activity unit of 8000U, and keeping temperature at 40 deg.C for 10 hr; standing for layering, and collecting precipitate;
(2) dissolving 100g of precipitate with 1.4L of ethanol water solution with volume fraction of 80%, adding 4g of selenium dioxide ethanol solution with mass fraction of 16% and 12g of polyethylene glycol (400Da, n is approximately equal to 3), and reacting for 7h at 65 ℃;
(3) concentrating under reduced pressure at 65 deg.C under 0.06MPa for 1.5 hr to remove ethanol, filtering with 0.4 μm filter membrane, and freeze drying to obtain theasaponin selenium nanoparticles 110 g.
Example 5
(1) Dissolving 1kg of theasaponin in 25kg of water, adding glucoamylase with activity unit 40000U, and keeping the temperature at 40 deg.C for 8 hr; standing for layering, and collecting precipitate;
(2) dissolving 100g of precipitate with 1.8L of ethanol water solution with volume fraction of 75%, adding 3g of selenium dioxide ethanol solution with mass fraction of 14% and 8g of polyethylene glycol (4000Da, n is approximately equal to 30), and reacting at 67 ℃ for 7.5 h;
(3) concentrating under reduced pressure at 55 deg.C under 0.02MPa for 2.5 hr to remove ethanol, filtering with 0.3 μm filter membrane, and freeze drying to obtain theasaponin selenium nanoparticles 107 g.
Example 6
(1) Dissolving 1kg of theasaponin in 18kg of water, adding glucoamylase with activity unit of 20000U, and keeping temperature at 45 deg.C for 7 hr; standing for layering, and collecting precipitate;
(2) dissolving 100g of precipitate with 1.6L of 77% ethanol water solution, adding 3.5g of 16% selenium dioxide ethanol solution and 14g of polyethylene glycol (6500Da, n is approximately equal to 50), and reacting at 70 ℃ for 6.5 h;
(3) concentrating under reduced pressure at 65 deg.C under 0.03MPa for 2 hr to remove ethanol, filtering with 0.22 μm filter membrane, and freeze drying to obtain theasaponin selenium nanoparticles 113 g.
Example 7
Taking 10g of the theasaponin selenium nanoparticles obtained in the embodiment 1-6, mixing with 30g of a mixture of starch, lactose and crystalline cellulose in a ratio of 7:2:1 and 1% of magnesium stearate uniformly, and preparing into tablets by a tablet machine.
Example 8
Taking 10g of the theasaponin selenium nanoparticles prepared in the examples 1-6, adding 30g of medicinal starch, uniformly mixing, performing wet granulation, adjusting with ethanol, loosening the prepared particles, sieving with a 20-mesh sieve, and drying in the air. Drying, and encapsulating to obtain capsule containing the sasanquasaponin derivative.
Test 1
Particle size and structure characterization of theasaponin selenium nanoparticles prepared in examples 1-6
The method comprises the following steps: after the theasaponin selenium nanoparticles prepared in examples 1 to 6 were dispersed in water, the particle size thereof was measured by a malvern nano-particle sizer; preparing 1mg/mL sample solution by using DMSO as a solvent, and scanning by using an ultraviolet spectrophotometer; preparing a KBr sheet, and performing infrared spectrum scanning; each constituent element was analyzed.
As a result: the average particle diameters of the theasaponin selenium nanoparticles prepared in examples 1 to 6 are 152nm, 213nm, 168nm, 154nm, 175nm and 183nm, respectively. Ultraviolet scanning shows that characteristic peaks of the tea saponin are subjected to red shift; the infrared spectrum shows that the peak of aldehyde group of the complex (1721 cm)-1) Disappeared at 723cm-1A new broad peak is added, and the peak is a stretching vibration peak for forming a bond between selenium and oxygen, which indicates Se4 +And the coordination reaction is carried out with the aldehyde group of the sasanquasaponin. The element analysis result shows that the proportion of the tea saponin, the selenium atom and the polyethylene glycol is 2:1:2, and the tea saponin has the following structure:
wherein n is 3 to 50.
Test 2
10g of the theasaponin selenium nanoparticles obtained in examples 1 to 6 were dissolved in 1000mL of polysorbate, and the solution was filled into a vial to prepare an injection.
The theasaponin selenium nanoparticles have obvious anti-aging effect, and are proved by the following experiments:
the antioxidant effect experiment of the theasaponin selenium nanoparticles on aging mice:
the method comprises the following steps: taking 110 mice with the weight of 20 +/-2 g, and randomly dividing the mice into a normal control group, a model group, a positive control group (VE), a high-low dose group of theasaponin selenium nanoparticles in example 1, a high-low dose group of theasaponin selenium nanoparticles in examples 2-6 and a camellia saponin group, wherein each group comprises 10 mice. The corresponding drugs are infused into the stomachs of the experimental groups, and when the drugs are administered, the mice of the model group and the drug group are injected with 0.5mL (160mg/kg) of 5 percent D-galactose subcutaneously at the neck and the back every day, the control group is injected with equivalent physiological saline, after 6 weeks of molding, blood is taken from eye sockets, after cervical vertebra is removed and the patients die, liver and brain tissues are separated, and the SOD activity and the MDA content of serum and tissues are measured and calculated according to the operation method of a test kit.
As a result: the content of MDA in serum, liver and brain tissue of aging model mouse caused by D-galactose is obviously increased, and the activity of free radical related scavenging enzyme SOD is reduced. Examples 1-6 theasaponin selenium nanoparticles can significantly reduce the MDA (lipid peroxidation) final product in serum, liver and brain tissues of aging mice, while the activity of SOD (superoxide dismutase) is increased, which is significantly superior to that of theasaponin group and has dose dependence. The effect of the theasaponin selenium nanoparticles shows that the theasaponin selenium nanoparticles enhance the antioxidant function of organisms and have the anti-aging effect. The results are shown in tables 1 and 2.
TABLE 1 Effect of theasaponin selenium nanoparticles on MDA content in serum, liver and brain of aging mice ((
n＝10)
TABLE 2 Effect of theasaponin selenium nanoparticles on SOD activity in serum, liver and brain of aging mice: (
n＝10)
The above embodiments are preferred embodiments of the present invention, but the present invention is not limited to the above embodiments, and any other changes, modifications, substitutions, combinations, and simplifications which do not depart from the spirit and principle of the present invention should be construed as equivalents thereof, and all such changes, modifications, substitutions, combinations, and simplifications are intended to be included in the scope of the present invention.
Claims (7)
1. The tea saponin selenium complex is characterized by having the following structure:
wherein n is 3 to 50.
2. A method for preparing theasaponin selenium nanoparticles comprising the theasaponin selenium complex of claim 1, comprising the steps of:
(1) dissolving theasaponin in water with the mass 15-30 times that of theasaponin, adding glucoamylase, and keeping the temperature at 35-55 ℃ for 4-12 hours; standing for layering, and collecting precipitate;
(2) dissolving the precipitate with an ethanol water solution, adding a selenium dioxide ethanol solution with the mass of 2-5% of the precipitate and 5-20% of polyethylene glycol, and reacting at 60-70 ℃ for 6-8 h;
(3) concentrating under reduced pressure to evaporate ethanol, filtering with a filter membrane of 0.22-0.45 μm, and freeze-drying to obtain theasaponin selenium nanoparticles;
adding 500-5000U of glucoamylase into every 100g of theasaponin in the step (1);
the volume fraction of the ethanol aqueous solution in the step (2) is 70-85%, and the addition amount is that the liquid-solid ratio of the ethanol aqueous solution to the precipitate is (10-20) mL/g;
the molecular weight of the polyethylene glycol in the step (2) is 400-6500 Da.
3. The method for preparing theasaponin selenium nanoparticles as claimed in claim 2, wherein the weight percentage of the selenium dioxide ethanol solution is 10-20%.
4. The method for preparing theasaponin selenium nanoparticles as claimed in claim 2, wherein the conditions of the reduced pressure concentration in step (3) are 0.01-0.1 MPa, the temperature is 50-70 ℃, and the time is 1-3 h.
5. The theasaponin selenium nanoparticles prepared by the method for preparing theasaponin selenium nanoparticles as claimed in any one of claims 2 to 4.
6. The use of theasaponin selenium nanoparticles as claimed in claim 5, for the preparation of an anti-aging medicament for scavenging free radicals in the body.
7. The use of theasaponin selenium nanoparticles as claimed in claim 6, wherein the anti-aging pharmaceutical dosage form is oral or injectable.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102030804A (en) * | 2010-10-21 | 2011-04-27 | 华南理工大学 | Method for preparing theasapogenol |
| CN105461781A (en) * | 2015-12-17 | 2016-04-06 | 华南理工大学 | Tea sapogenin zinc complex and preparation method as well as use thereof |
| CN107635561A (en) * | 2015-03-31 | 2018-01-26 | 株式会社爱茉莉太平洋 | Contain composition of the theasapogenol derivative as active component |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102030804A (en) * | 2010-10-21 | 2011-04-27 | 华南理工大学 | Method for preparing theasapogenol |
| CN107635561A (en) * | 2015-03-31 | 2018-01-26 | 株式会社爱茉莉太平洋 | Contain composition of the theasapogenol derivative as active component |
| CN105461781A (en) * | 2015-12-17 | 2016-04-06 | 华南理工大学 | Tea sapogenin zinc complex and preparation method as well as use thereof |
Non-Patent Citations (2)
| Title |
|---|
| Synthesis and neuroprotective effects of the complex nanoparticles of iron and sapogenin isolated from the defatted seeds of Camellia oleifera;Qian Yang 等;《Pharmaceutical Biology》;20161209;第55卷(第1期);参见全文 * |
| 含硒高分子: 一类新型生物材料;曹玮 等;《化学通报》;20131231;第76卷(第4期);参见第291页第1段,第292页图式1 * |
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