CN117694535A - Method for preparing curcumin-arylcurcumone nanocrystalline, preparation and application - Google Patents
Method for preparing curcumin-arylcurcumone nanocrystalline, preparation and application Download PDFInfo
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- LUEWUZLMQUOBSB-GFVSVBBRSA-N mannan Chemical class O[C@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@@H](O[C@@H]2[C@H](O[C@@H](O[C@H]3[C@H](O[C@@H](O)[C@@H](O)[C@H]3O)CO)[C@@H](O)[C@H]2O)CO)[C@H](O)[C@H]1O LUEWUZLMQUOBSB-GFVSVBBRSA-N 0.000 description 1
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Landscapes
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicinal Preparation (AREA)
Abstract
The invention discloses a method for preparing curcumin-arylcurcumone nanocrystalline, a preparation and application thereof, wherein curcumin powder is added into a fenugreek gum solution with the mass fraction of 1-2% under stirring to ensure that the final concentration of curcumin is 1-2%, then arylcurcumone and an emulsifying agent are added to ensure that the final concentration of arylcurcumone is 1-2%, and the final concentration of the emulsifying agent is 0.1-0.5%, and uniformly mixed to obtain a curcumin-arylcurcumone crystal mixed solution; the curcumin-arylcurcumone crystal mixed liquid is sheared at high speed and homogenized at high pressure to prepare curcumin-arylcurcumone nanocrystalline liquid, and then the curcumin-arylcurcumone nanocrystalline liquid is dried to obtain the curcumin-arylcurcumone nanocrystalline preparation. The invention uses food-grade polysaccharide fenugreek gum as a stabilizer to prepare the curcumin-arylcurcumone nanocrystalline preparation, improves the dispersibility and bioavailability of curcumin and arylcurcumone on the premise of retaining the bioactivity of curcumin and arylcurcumone, and the product is food-grade and can be used for preparing nutritional preparations for supplementing curcumin.
Description
Technical Field
The invention relates to a method for preparing curcumin-arylcurcumone nanocrystalline, a preparation and application thereof.
Background
Curcumin and arylcurcumone are active ingredients derived from Curcuma rhizome, and have molecular formula C 21 H 20 O 6 And C 15 H 22 O has various activities such as anti-inflammatory, anti-tumor, antioxidant and liver protecting. However, curcumin and arylcurcuminones have a solubility in water of less than 0.01% and are hardly absorbed by the human body after oral administration. This is an important factor that hinders curcumin, arylcurcuminones as nutritional supplements. In recent years, more researches are carried out on preparing curcumin and arylcurcuminones into amorphous states, so that the solubility and bioavailability of the curcumin and arylcurcuminones are improved. However, a large amount of organic reagents are required to dissolve curcumin and arylcurcuminones in the production process, and the explosion risk exists. And the residual organic solvent may be harmful to the producer and the taker.
Nanocrystalline is a new drug delivery method that has been developed in recent years to significantly increase the absorption efficiency of the human body. The principle is that the water-insoluble medicine is mechanically broken into nano-level crystals, so that intestinal cells can be directly absorbed through endocytosis, thereby improving the bioavailability of the medicine. Currently, more than 20 nanocrystalline drugs are approved for sale. The nanocrystalline drug is prepared by a mechanical method, does not need an organic solvent, is safe to produce and is environment-friendly. The nanocrystalline drug requires the addition of stabilizers to prevent the nanocrystals from aggregating. Stabilizers are generally amphiphilic polymers. Almost all stabilizers reported at present are synthetic high molecular materials such as polyvinyl alcohol PVA, poloxamer P188, polyethylene glycol PEG4000, etc. These synthetic polymeric materials have not been used for food due to safety issues. Polysaccharides are natural high molecular materials, are often used as stabilizers and emulsifiers in foods, and are expected to replace synthetic high molecular materials as stabilizers for nanocrystalline delivery systems. However, the stability of the synthesized polymer material to the nanocrystalline drug cannot be achieved. There remains a need to further optimize formulations that can efficiently stabilize nanocrystalline delivery systems.
The fenugreek gum is derived from fenugreek seeds, is a heterogeneous polysaccharide consisting of a beta- (1-4) -D-manna main chain and a single D-galactose branch connected by alpha- (1-6), belongs to a novel functional dietary fiber raw material, and is commonly used as a stabilizer and an emulsifier in foods. The main chain of the mannans of the fenugreek gum is hydrophobic, and the galactose side chains are hydrophilic, so that the fenugreek gum is an amphiphilic polysaccharide. The prior art has no report that the fenugreek gum is used for nanocrystalline preparation.
Disclosure of Invention
The invention aims to provide a novel method for preparing curcumin-arylcurcumone nanocrystals.
The invention adopts the technical scheme that:
a method of preparing curcumin-arylcurcumone nanocrystals, the method comprising the steps of:
(1) Preparing curcumin-arylcurcumone crystal mixed solution: adding curcumin powder into a fenugreek gum solution with the mass fraction of 1-2% under stirring to ensure that the final concentration of curcumin is 1-2%, adding aromatic turmeric ketone and an emulsifying agent to ensure that the final concentration of aromatic turmeric ketone is 1-2%, and uniformly mixing to ensure that the final concentration of the emulsifying agent is 0.1-0.5%, thereby obtaining a curcumin-aromatic turmeric ketone crystal mixed solution;
(2) Shearing the curcumin-arylcurcumone crystal mixed liquid at a high speed to obtain a curcumin-arylcurcumone crystal suspension, and homogenizing the curcumin-arylcurcumone crystal suspension at a high pressure to obtain the curcumin-arylcurcumone nanocrystalline liquid.
In the step (1), the fenugreek gum solution is generally prepared by the following method: and adding the fenugreek gum into water according to the mass fraction of 1-2%, and uniformly stirring for 1-2 hours at the temperature of 50-60 ℃ at the speed of 450 r/min to obtain a fully-swelled fenugreek gum solution.
Preferably, the mass fraction of the fenugreek gum solution is 1.5%.
Preferably, the final concentration of curcumin is 1.5% and the final mass concentration of arylcurcuminones is 1%.
The emulsifier is Tween or span, preferably Tween 80.
The final mass concentration of the emulsifier is preferably 0.1-0.2%.
In the step (2), a high-speed shearing machine is generally used for shearing the curcumin-arylcurcumone crystal suspension at a high speed, the rotating speed is 8000-10000 rpm, and the time is 5-7 min, so that the uniform curcumin-arylcurcumone crystal suspension is obtained.
In the step (3), a high-pressure homogenizer is generally used for homogenizing the curcumin-aryl curcumone crystal suspension at high pressure, and the homogenizing steps are as follows: stabilizing for 2 min under normal pressure, wherein the pressure is 100 bar, homogenizing for 3-4 times, and obtaining uniform curcumin-arylcurcumone nanocrystalline liquid.
In the curcumin-arylcurcumone nanocrystalline liquid prepared by the invention, curcumin and arylcurcumone exist in a nanocrystalline form.
The method may further comprise the steps of:
drying the curcumin-arylcurcumone nanocrystalline liquid to obtain the curcumin-arylcurcumone nanocrystalline preparation.
Further, the drying step is preferably:
adding food grade silicon dioxide with the final concentration of 0.001-0.005% into the curcumin-arylcurcumone nanocrystalline liquid, and then pouring into a plate for forced air drying to obtain a curcumin-arylcurcumone nanocrystalline dry product; pulverizing the curcumin-arylcurcumone nanocrystalline dry product to powder below 200 meshes to obtain the curcumin-arylcurcumone nanocrystalline preparation.
The final concentration of the food grade silica is preferably 0.002%.
The invention also provides the curcumin-arylcurcumone nanocrystalline preparation prepared by the method.
And the application of the curcumin-arylcurcumone nanocrystalline preparation in preparing curcumin supplementary nutrition preparation.
Such formulations include, but are not limited to, beverages, capsules, powders, tablets, and the like.
The preparation method adopted by the invention is a pure mechanical method, and the curcumin-arylcurcumone nanocrystalline prepared by the invention inherits the pharmacological activity of curcumin and arylcurcumone, so that the stability of the curcumin-arylcurcumone nanocrystalline is obviously improved.
The invention utilizes the characteristic of the trigonella foenum-graecum amphiphilic polysaccharide, can be adsorbed on the surfaces of hydrophobic curcumin and arylcurcumone nanocrystals in a water phase, and plays a role of a stabilizer. And the fenugreek gum can be slowly fermented and decomposed by intestinal microorganisms in the intestinal tract, so that the slow release of curcumin and aromatic curcumone can be realized.
The invention has the beneficial effects that:
1. is suitable for water-oil insoluble compounds, and solves the problem of drug delivery necessary for non-dissolution.
2. The food-grade natural high polymer polysaccharide is taken as a stabilizer, meets the national standard GB2760 of food additives, is safe and healthy, is edible, and can be used for preparing various nutritional foods.
3. The nutrient preparation is prepared by a purely mechanical mode, the process is simple, and the potential hazard of the organic reagent is eliminated.
4. In the prepared preparation, curcumin and aryl curcuminoid exist in a nanocrystalline form, so that the physicochemical stability of the curcumin and the aryl curcuminoid is improved.
5. The aryl curcuminones are added into the curcumin product for the first time, so that the efficacy of the curcumin nanocrystalline is improved, and the strong turmeric flavor is endowed.
6. Food-grade SiO is added 2 As an anticaking agent, aggregation of the powder formulation is inhibited.
7. A small amount of food-grade emulsifier is used, and the amount of the emulsifier is very small, and the fenugreek gum is mainly used as a main stabilizer.
According to the invention, a pure mechanical method is adopted, the food-grade polysaccharide fenugreek gum is used as a stabilizer to prepare the curcumin-arylcurcumone nanocrystalline delivery system, the dispersibility and bioavailability of curcumin and arylcurcumone are improved on the premise of retaining the bioactivity of curcumin and arylcurcumone, and the stabilizer is food-grade polysaccharide, so that the product can be used for preparing a nutritional food preparation.
Drawings
Fig. 1 is an X-ray diffraction pattern of curcumin crystals and curcumin-arylcurcumone nanocrystalline formulation prepared in example 1.
FIG. 2 is a TEM image of the curcumin-arylcurcumone nanocrystalline formulation prepared in example 1; wherein a is: scale 1 μm; b, drawing: scale 100nm.
FIG. 3 is a graph showing physicochemical and functional properties of the curcumin-arylcurcumone nanocrystal preparation prepared in example 1; wherein a is a histogram of average particle size and thermal stability; panel B is a histogram of in vitro antioxidant and anticancer cell proliferation activity; panel C is an in vitro dissolution profile of simulated gastric fluid in vitro (pH 1.2); panel D is an in vitro dissolution profile of simulated intestinal fluid (pH 7.4) in vitro.
Detailed Description
In order to make the technical solution of the present application more clear, the technical solution of the present invention will be described in detail below with reference to the accompanying drawings and examples, which belong to the protection scope of the present invention, but do not limit the protection scope of the present invention.
Example 1 curcumin-arylcurcumone nanocrystalline formulation for use in preparing a curcumin-arylcurcumone supplement beverage, the steps of:
(1) Precisely weighing 15 g of the fenugreek gum powder, placing in 1L of water, and stirring at constant speed of 450 r/min at 60 ℃ for 1 h to obtain fully swelled fenugreek gum solution.
(2) Precisely weighing 15 g curcumin powder, and adding into the uniformly stirred fenugreek gum solution obtained in the step 1 to make the total mass fraction of the solid powder be 3%. Continuously stirring at 60 ℃ at a constant speed of 450 r/min for 1 h, adding 10g of arylcurcuminoids and 2g of tween 80 to make the final mass fraction of the arylcurcuminoids be 1% and 0.2%, and uniformly mixing to obtain the curcumin-arylcurcuminoids crystal mixed solution.
(3) And (3) shearing the curcumin-arylcurcumone crystal mixed solution obtained in the step (2) at a high speed by using a high-speed shearing machine, wherein the rotating speed is 8000 rpm, and the time is 5 min, so that the uniform curcumin-arylcurcumone crystal suspension is obtained.
(4) Homogenizing the curcumin-arylcurcumone crystal suspension obtained in the step 3 at high pressure by using a high-pressure homogenizer, wherein the homogenizing steps are as follows: stabilizing for 2 min under normal pressure, homogenizing for 3 times at 100 bar to obtain uniform curcumin-arylcurcumone nanocrystalline liquid.
(5) Weighing food-grade SiO with mass fraction of 0.002% 2 Adding the curcumin-arylcurcumone nanocrystalline liquid obtained in the step 4, uniformly mixing, pouring the mixture into a plate, drying the mixture in an oven at 50 ℃ in a blasting way for 24 h, and crushing the curcumin-arylcurcumone nanocrystalline dried product to below 200 meshes by using a small traditional Chinese medicine crusher to obtain the curcumin-arylcurcumone nanocrystalline preparation. Physical and chemical properties and in-vitro dissolution rate are detected, and the results are shown in figures 1-3.
(6) Precisely weighing 1 g curcumin-arylcurcumone nanocrystalline preparation, dissolving in 100 mL water, and stirring uniformly to obtain curcumin-arylcurcumone supplementary beverage.
The X-ray diffraction patterns of the curcumin crystals and the curcumin-arylcurcumone nanocrystalline preparation prepared in example 1 are shown in fig. 1. The results in fig. 1 show that there is a diffraction peak specific to curcumin in the curcumin-arylcurcumone nanocrystalline formulation, indicating that the method does not destroy the crystal structure of curcumin during preparation.
A TEM image of the curcumin-arylcurcumone nanocrystalline formulation prepared in example 1 is shown in fig. 2, in which a is: scale 1 μm; b, drawing: scale 100nm. The results of FIG. 2 show that the nanocrystals exhibit better dispersibility, with the nanocrystal particle size being about 200-500 nm.
The physicochemical and functional characteristics of the curcumin-arylcurcumone nanocrystalline preparation prepared in example 1 are shown in fig. 3, wherein a is a histogram of average particle size and thermal stability; panel B is a histogram of in vitro antioxidant and anticancer cell proliferation activity; panel C is an in vitro dissolution profile of simulated gastric fluid in vitro (pH 1.2); panel D is an in vitro dissolution profile of simulated intestinal fluid (pH 7.4) in vitro.
The results in fig. 3 show that the particle size of the curcumin-arylcurcumone nanocrystalline preparation reaches the nanoscale compared with the pure curcumin product, and the thermal stability is greatly improved. The in vitro oxidation resistance is improved, the protein denaturation inhibition activity is greatly improved, and the curcumin-arylcurcumone nanocrystalline preparation can improve the anti-inflammatory effect of curcumin single substances and enhance the protection effect on proteins. In addition, the anti-cancer cell proliferation activity of the curcumin-arylcurcumone nanocrystalline preparation is improved to 90%, and the effect is obviously improved.
From the in vitro dissolution curve, the in vitro dissolution of the curcumin-arylcurcumone nanocrystalline preparation in simulated gastric fluid is more than 10 times of curcumin, and the in vitro dissolution of the curcumin-arylcurcumone nanocrystalline preparation in simulated intestinal fluid can reach 70%, so that the bioavailability is remarkably improved.
Example 2 curcumin-arylcurcumone nanocrystalline formulation was used to prepare curcumin-arylcurcumone supplement capsules, which were prepared as follows:
(1) Precisely weighing 10g of the fenugreek gum powder, placing in 1L water, and stirring at a constant speed of 450 r/min at 60 ℃ for 1 h to obtain fully swelled fenugreek gum solution.
(2) Precisely weighing 20 g curcumin powder, and adding into the uniformly stirred fenugreek gum solution obtained in the step 1 to make the total mass fraction of the solid powder be 3%. Continuously stirring at 60 ℃ at a constant speed of 450 r/min for 1 h, adding 1% and 0.15% of arylcurcuminoids and tween 80, and uniformly mixing to obtain curcumin-arylcurcuminoids crystal mixed solution.
(3) And (3) shearing the curcumin-arylcurcumone crystal mixed solution obtained in the step (2) at a high speed by using a high-speed shearing machine, wherein the rotating speed is 8000 rpm, and the time is 5 min, so that the uniform curcumin-arylcurcumone crystal suspension is obtained.
(4) Homogenizing the curcumin-arylcurcumone crystal suspension obtained in the step 3 at high pressure by using a high-pressure homogenizer, wherein the homogenizing steps are as follows: stabilizing for 2 min under normal pressure, and circulating at 100 bar for 3 times to obtain uniform curcumin-arylcurcumone nanocrystalline liquid.
(5) Weighing food-grade SiO with mass fraction of 0.002% 2 Adding into step 4And (3) uniformly mixing the curcumin-arylcurcumone nanocrystalline liquid, pouring the mixture into a plate, drying the mixture in an oven at 50 ℃ in a blasting way for 24 h, and crushing the curcumin-arylcurcumone nanocrystalline dried product to below 200 meshes by using a small traditional Chinese medicine crusher to obtain the curcumin-arylcurcumone nanocrystalline preparation.
(6) And (3) placing the 0.25 g curcumin-arylcurcumone nanocrystalline preparation into a purchased enteric capsule to obtain the curcumin-arylcurcumone supplementing capsule.
Claims (10)
1. A method for preparing curcumin-arylcurcumone nanocrystals, characterized in that the method comprises the steps of:
(1) Preparing curcumin-arylcurcumone crystal mixed solution: adding curcumin powder into a fenugreek gum solution with the mass fraction of 1-2% under stirring to ensure that the final concentration of curcumin is 1-2%, adding aromatic turmeric ketone and an emulsifying agent to ensure that the final concentration of aromatic turmeric ketone is 1-2%, and uniformly mixing to ensure that the final concentration of the emulsifying agent is 0.1-0.5%, thereby obtaining a curcumin-aromatic turmeric ketone crystal mixed solution;
(2) Shearing the curcumin-arylcurcumone crystal mixed liquid at a high speed to obtain a curcumin-arylcurcumone crystal suspension, and homogenizing the curcumin-arylcurcumone crystal suspension at a high pressure to obtain the curcumin-arylcurcumone nanocrystalline liquid.
2. The method of claim 1, wherein in step (1), the fenugreek gum solution is prepared by: and adding the fenugreek gum into water according to the mass fraction of 1-2%, and uniformly stirring for 1-2 hours at the temperature of 50-60 ℃ at the speed of 450 r/min to obtain a fully-swelled fenugreek gum solution.
3. The method of claim 1, wherein in the step (1), the mass fraction of the fenugreek gum solution is 1.5%.
4. The method of claim 1, wherein in step (1), the final concentration of curcumin is 1.5% and the final concentration of arylcurcuminoids is 1%.
5. The method of claim 1, wherein in step (1), the emulsifier is tween or span.
6. The method of claim 1, wherein in step (1), the final mass concentration of the emulsifier is 0.1-0.2%.
7. The method of claim 1, further comprising the steps of:
drying the curcumin-arylcurcumone nanocrystalline liquid to obtain the curcumin-arylcurcumone nanocrystalline preparation.
8. The method of claim 7, wherein the drying step is:
adding food grade silicon dioxide with the final concentration of 0.001-0.005% into the curcumin-arylcurcumone nanocrystalline liquid, and then pouring into a plate for forced air drying to obtain a curcumin-arylcurcumone nanocrystalline dry product; pulverizing the curcumin-arylcurcumone nanocrystalline dry product to powder below 200 meshes to obtain the curcumin-arylcurcumone nanocrystalline preparation.
9. A curcumin-arylcurcumone nanocrystalline formulation prepared by the method of claim 7 or 8.
10. Use of a curcumin-arylcurcumone nanocrystalline formulation as claimed in claim 9 in the preparation of a curcumin supplementary nutritional formulation.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202311645725.1A CN117694535A (en) | 2023-12-04 | 2023-12-04 | Method for preparing curcumin-arylcurcumone nanocrystalline, preparation and application |
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| Application Number | Priority Date | Filing Date | Title |
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| CN202311645725.1A CN117694535A (en) | 2023-12-04 | 2023-12-04 | Method for preparing curcumin-arylcurcumone nanocrystalline, preparation and application |
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| CN202311645725.1A Pending CN117694535A (en) | 2023-12-04 | 2023-12-04 | Method for preparing curcumin-arylcurcumone nanocrystalline, preparation and application |
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| Country | Link |
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