CN115919765A - Nanoemulsion based on cinnamyl aldehyde and application thereof - Google Patents
Nanoemulsion based on cinnamyl aldehyde and application thereof Download PDFInfo
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Abstract
The invention discloses a nanoemulsion based on cinnamaldehyde and application thereof. Based on the characteristic that cinnamaldehyde is oily liquid, the nanoemulsion and the drug-loaded nanoemulsion are prepared by taking cinnamaldehyde as an oil phase, so that the solubility and the stability of cinnamaldehyde in water are improved, and the drug effect is enhanced; experimental data show that both the nanoemulsion and the drug-loaded nanoemulsion have the effect of resisting hepatic fibrosis.
Description
Technical Field
The invention relates to the technical field of pharmaceutical preparations, in particular to a nano-emulsion based on cinnamaldehyde and application thereof.
Background
Hepatic fibrosis is a pathological process of abnormal proliferation of connective tissues of the liver caused by acute and chronic liver injury. The primary diseases such as viral hepatitis, excessive alcohol intake, fatty liver disease, cholestasis and the like can cause repeated damage and repair of liver cells, and finally generate fibrosis pathological changes. Early hepatic fibrosis is reversible, and reversal regression can be realized through intervention such as drug therapy, so that diagnosis and treatment of early hepatic fibrosis are very important, otherwise, liver cirrhosis can be developed, even hepatocellular carcinoma can be further developed, and the life health of a patient is seriously damaged. Liver fibrosis cannot be self-healed, and primary diseases and liver fibrosis need to be treated at the same time. However, at present, no effective drug treatment method specific to hepatic fibrosis exists, and hepatic fibrosis is often difficult to reverse. Therefore, the anti-hepatic fibrosis medicine is still a hot point for research and development of liver and gall disease medicines, and has profound significance for human health cause by blocking and even reversing hepatic fibrosis process through medicine treatment.
The cinnamaldehyde is an aldehyde natural organic compound extracted from a traditional Chinese medicinal and edible plant (cinnamon), and is a light yellow oily liquid at room temperature. The structural formula of cinnamaldehyde is as follows:
cinnamaldehyde has pharmacological activities such as anti-inflammatory and anti-oxidation, but a literature report that cinnamaldehyde is related to treatment of liver diseases is not found yet.
Disclosure of Invention
Aiming at the technical problems in the prior art, the invention provides a nanoemulsion based on cinnamaldehyde and application thereof.
The invention discloses a cinnamaldehyde-based nanoemulsion which comprises cinnamaldehyde, an emulsifier and water.
Preferably, the nanoemulsion further comprises a fat-soluble drug.
Preferably, the fat-soluble drug comprises valsartan or vitamin a.
Preferably, the mass ratio of the cinnamaldehyde to the emulsifier to the vitamin A to the water is 12:6-18:1-4:100, respectively;
the mass ratio of the cinnamaldehyde to the emulsifier to the valsartan to the water is 60:60:6:500.
preferably, the nanoemulsion further comprises a co-emulsifier.
Preferably, the emulsifier comprises any one or a combination of the following ingredients: polyoxyethylene castor oil (EL) and polyoxyethylene hydrogenated castor oil (EH); the coemulsifier comprises: ethanol, propylene glycol, polyethylene glycol 400 or n-butanol.
Preferably, the preparation method of the nanoemulsion comprises the following steps: mixing cinnamaldehyde and an emulsifier uniformly to obtain a first oil phase system; and dropwise adding water into the first oil phase system, and stirring to obtain the nanoemulsion.
Preferably, the preparation method of the nanoemulsion comprises the following steps: mixing cinnamaldehyde, an emulsifier and a fat-soluble drug uniformly to obtain a second oil phase system; and dropwise adding water into the second oil phase system, and stirring to obtain the drug-loaded nanoemulsion.
Preferably, the nanoemulsion is used for preparing medicines or foods for resisting hepatic fibrosis.
Preferably, the medicine is used for prolonging the retention time of cinnamaldehyde and fat-soluble medicines in the intestinal tract and enhancing the intestinal absorption of the medicines, thereby enhancing the anti-hepatic fibrosis efficacy of the medicines.
Compared with the prior art, the invention has the beneficial effects that:
based on the characteristic that cinnamaldehyde is oily liquid, the nanoemulsion and the drug-loaded nanoemulsion are prepared by taking cinnamaldehyde as an oil phase, so that the solubility and the stability of cinnamaldehyde in water are improved, and the drug effect is enhanced; experimental data show that both the nanoemulsion and the drug-loaded nanoemulsion have the effect of resisting hepatic fibrosis.
Drawings
FIG. 1 is a flow chart of a nanoemulsion preparation method of the present invention;
FIG. 2 is a graph of fluorescein imaging results;
FIG. 3 is a graph showing the result of staining a liver tissue sample.
Detailed Description
In order to make the objects, technical solutions and advantages of the embodiments of the present invention clearer, the technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the drawings in the embodiments of the present invention, and it is obvious that the described embodiments are some embodiments of the present invention, but not all embodiments. All other embodiments, which can be obtained by a person skilled in the art without any inventive step based on the embodiments of the present invention, are within the scope of the present invention.
The invention is described in further detail below with reference to the attached drawing figures:
a cinnamaldehyde-based nanoemulsion comprises cinnamaldehyde, an emulsifier, and water. The nano-emulsion increases the solubility and stability of the cinnamaldehyde in water and enhances the drug effect; the anti-hepatic fibrosis effect is embodied in a specific test.
The emulsifier comprises any one or combination of the following components: tween 80, polyoxyethylene castor oil (EL) and polyoxyethylene hydrogenated castor oil (EH).
As shown in fig. 1, the preparation method of the nanoemulsion comprises the following steps:
step S1: the cinnamaldehyde and the emulsifier are uniformly mixed to obtain a first oil phase system.
Step S2: and dropwise adding water into the first oil phase system, and stirring to obtain the nanoemulsion.
The oil phase can be added with fat-soluble drugs to form a drug-loaded nanoemulsion, and the fat-soluble drugs comprise valsartan or vitamin A (Va), but are not limited to the valsartan or the vitamin A. The preparation method of the drug-loaded nanoemulsion comprises the following steps:
step 101: and mixing the cinnamaldehyde, the emulsifier and the fat-soluble medicine uniformly to obtain a second oil phase system.
Step 102: and dropwise adding water into the second oil phase system, and stirring to obtain the drug-loaded nanoemulsion.
Emulsifier screening
The preparation method of the nano-emulsion comprises the following steps:
step 201: weighing 600mg of cinnamaldehyde and 300-900mg of emulsifier at room temperature, and mixing uniformly to obtain a first oil phase system.
Step 202: 5ml of water is added into the first oil phase system drop by drop, and the rotating speed of 600rpm is kept in the dropping process, so that a uniform dispersion system, namely the cinnamaldehyde nanoemulsion, is formed spontaneously.
Step 203: the types and the dosages of the emulsifying agents are respectively inspected, and the grain diameter, PD I (polydispersity index) and appearance of the cinnamaldehyde nanoemulsion are used as inspection indexes; after standing at 4 ℃ for 7 days, the particle size, PD I and appearance of the cinnamaldehyde nanoemulsion were measured again. The measurement results are shown in table 1:
TABLE 1
In Table 1, EL is polyoxyethylene castor oil and RH is polyoxyethylene hydrogenated castor oil. The results in Table 1 show that the preferable combination of the type and amount of the emulsifier is that when cinnamaldehyde is used as the oil phase and Tween 80 is used as the emulsifier, an emulsion with uniform particle size is difficult to form, PDI is large, and the layering phenomenon occurs after the emulsion is placed; taking cinnamaldehyde as an oil phase, taking polyoxyethylene castor oil EL as an emulsifier, and forming the nanoemulsion with uniform particle size when the mass ratio of the emulsifier to the cinnamaldehyde is greater than 0.5, particularly greater than or equal to 1; when the emulsifier is polyoxyethylene hydrogenated castor oil RH, the nanoemulsion with uniform particle size can be formed, but when the mass ratio of the emulsifier to the cinnamaldehyde is more than or equal to 1, PDI is large, the particle size uniformity is poor, and when the dosage of the emulsifier is increased, the layering phenomenon is easy to occur after standing.
Component screening of drug-loaded nano-emulsion
The drug-loaded nanoemulsion is prepared by taking cinnamaldehyde as an oil phase, polyoxyethylene castor oil EL or polyoxyethylene hydrogenated castor oil RH as an emulsifier and adopting vitamin A or valsartan as a fat-soluble drug. The preparation method comprises the following steps:
step 301: weighing 600mg of cinnamaldehyde, 300-900mg of emulsifier and 50-200mg of Va at room temperature, and uniformly mixing to obtain a third oil phase system. Or under the condition of room temperature, weighing 600mg of cinnamaldehyde and 600mg of emulsifier EL, uniformly mixing, adding valsartan in times, adding 60mg of valsartan in total, and dissolving to obtain a fourth oil phase system.
Step 302: 5ml of water is dropwise added into the third oil phase system or the fourth oil phase system, and the rotation speed of 600rpm is kept in the dropwise adding process, so that a uniform dispersion system, namely the drug-loaded nano-emulsion/drug-loaded emulsion, is spontaneously formed.
Step 303: detecting the particle size, PDI and appearance of the prepared drug-loaded nanoemulsion (cinnamaldehyde-Va); after being placed at 4 ℃ for 7 days, the particle size, PDI and appearance of the drug-loaded nano-emulsion are detected again. The results are shown in table 2:
TABLE 2
Example 24, the particle size of the drug-loaded nanoemulsion (cinnamaldehyde-valsartan) prepared based on the fourth oil phase system is 141.2nm, the pd I is 0.27, and the appearance is good, so that the prepared cinnamaldehyde-valsartan drug-loaded nanoemulsion with uniform particle size is obtained; and after standing for 3 days, the particle size, PD I and appearance are not obviously changed.
From examples 10 to 23: when the oil phase is cinnamaldehyde, the entrapped drug is Va, and the emulsifier is polyoxyethylene hydrogenated castor oil RH, the cinnamaldehyde-Va drug-loaded emulsion with uniform particle size is difficult to form, and the PD I is large. The oil phase is cinnamaldehyde, the entrapped drug is Va, and when the emulsifier is polyoxyethylene castor oil EL, the cinnamaldehyde-Va drug-loaded nanoemulsion with uniform particle size can be formed. When the dosage of EL is 600mg, the maximum drug loading of Va is 100mg. Wherein, PD I is less than or equal to 0.3 and is used as a measurement index of uniform particle size.
Screening of co-emulsifier:
the cinnamaldehyde-Va drug-loaded nanoemulsion is prepared by taking cinnamaldehyde as an oil phase, polyoxyethylene castor oil EL as an emulsifier, va as a fat-soluble drug and respectively taking absolute ethyl alcohol, propylene glycol, PEG400 and n-butyl alcohol as auxiliary emulsifiers.
The preparation method comprises the following steps:
step 401: weighing 600mg of cinnamaldehyde, 600mg of EL, 50-150mg of Va and 1 ml of coemulsifier under the condition of room temperature, and uniformly mixing to obtain a third oil phase system.
Step 402: and (3) dropwise adding 5ml of water into the third oil phase system, and keeping the rotating speed of 600rpm in the dropwise adding process to spontaneously form a uniform dispersion system, namely the cinnamaldehyde-Va drug-loaded nanoemulsion.
Step 403: inspecting the types of the auxiliary emulsifying agents, and detecting the particle size, PD I and appearance of the cinnamaldehyde-Va drug-loaded nanoemulsion newly prepared under different conditions; after being placed at 4 ℃ for 7 days, the particle size, PD I and appearance of the drug-loaded nano-emulsion are detected again. The results are shown in table 3:
TABLE 3
From the results in Table 3, it can be seen that: when the oil phase is cinnamaldehyde, the entrapped drug is Va, the emulsifier is polyoxyethylene castor oil EL, and the co-emulsifier is absolute ethyl alcohol, propylene glycol and n-butyl alcohol, the drug-loaded nanoemulsion with uniform particle size and stable placement is difficult to form. When polyethylene glycol 400 (PEG 400) was added, stable nanoemulsions could be formed, but with a large PD I (> 0.3). Referring to the results of tables 2 and 3, it can be seen that the co-emulsifier is not an essential component for forming the nanoemulsion/drug-loaded nanoemulsion, and the co-emulsifier was not added in the subsequent study of the present invention.
And (3) detecting the content stability:
the cinnamaldehyde bulk drug (dispersed in water), the cinnamaldehyde nanoemulsion prepared in example 8 and the cinnamaldehyde-Va drug loaded nanoemulsion prepared in example 18 were placed in penicillin bottles, sealed and protected from light, placed at 25 ℃ and 4 ℃, and sampled and measured on different days for cinnamaldehyde content, and the results are shown in table 4:
TABLE 4
The results in table 4 show that the nanoemulsion obviously improves the stability of the cinnamaldehyde content, and the stability of the cinnamaldehyde-Va drug-loaded nanoemulsion is better than that of the cinnamaldehyde nanoemulsion.
And (3) in vivo distribution detection:
experimental animals: KM male mice, weight 25-35g.
Free fluorescein group (18): 18 KM mice were randomly selected as a free fluorescein group (referred to as "free group"), and after fasting for 12 hours, a sample solution containing fluorescein DER was administered by gavage 1 time (DR is a lipid-soluble cell membrane fluorescent probe; DR was diluted with olive oil to form a homogeneous oily liquid), and the administration dose of DR was 1mg/kg.
Cinnamaldehyde nanoemulsion group (18): 18 KM mice were randomly selected as cinnamaldehyde nanoemulsion groups (abbreviated as "nanoemulsion groups"), and after fasting for 12 hours, the cinnamaldehyde nanoemulsion of example 8, which was loaded with DIR at a dose of 1mg/kg and 360mg/kg, was administered by gavage for 1 time.
cinnamaldehyde-Va drug-loaded nanoemulsion group (18): 18 KM mice are randomly selected as a cinnamaldehyde-Va drug-loaded nanoemulsion group (called a drug-loaded group for short), after fasting for 12 hours, the example 18 cinnamaldehyde-Va drug-loaded nanoemulsion carrying the D IR is administered by gavage for 1 time, the administration dose of the D IR is 1mg/kg, and the administration dose of the cinnamaldehyde is 360mg/kg.
After the administration of the above groups, the mice were sacrificed by over-anesthesia in batches for a predetermined time (4 to 72 hours), and then the liver, intestine, spleen, and kidney were harvested for imaging. Because the fluorescein DR and the cinnamaldehyde are both fat-soluble and are simultaneously contained in the nanoemulsion, the DR content and the cinnamaldehyde content are in positive correlation in the research system. The fluorescence imaging results as shown in fig. 2 show that: compared with the free group and the nano-emulsion group, the drug-loaded group obviously prolongs the intestinal retention time of the drug and enhances the intestinal absorption of the drug. In addition, compared with the free group, the nanoemulsion group and the emulsion of the drug-loaded group can obviously improve the content of the DIR, namely the content of cinnamaldehyde in the liver. Especially, the liver accumulation of drug-loaded cinnamaldehyde is the largest, and accumulation still exists after 72 hours of administration; compared with the nanoemulsion group, the Va of the cinnamaldehyde-Va drug-loaded nanoemulsion has an intestinal retention effect, can prolong the intestinal absorption time of the drug, shows a certain liver targeting property, and enables the drug to be stored in the liver for a long time.
And (3) testing the drug effect:
experimental animals: SD male rats weighing 180-200g.
Cholestatic liver fibrosis (BDL) animal model: 30 experimental animals are fasted for 12 hours before operation; and (3) operation: anaesthetizing with isoflurane, opening abdomen under aseptic condition, lifting liver margin, pulling open duodenum, separating common bile duct by 2-3cm, ligating twice with 000-gauge silk at the position near duodenum and the position near hepatic portal, cutting common bile duct from the middle of two ligation positions, suturing incision after restoring liver to original position, anaesthetizing and waking animal, and drinking water freely.
BDL model group (6): 6 of the above BDL model animals were used as BDL model group (abbreviated as "model group") and 1 saline was administered by gavage every day starting on day 2 after surgery.
Bulk drug control group (6): taking 6 of the BDL modeling animals as a raw material drug comparison group (referred to as a comparison group for short), and performing gavage on the BDL modeling animals for 1 time every day from the 2 nd day after the operation, wherein the cinnamaldehyde is diluted by olive oil to form uniform oily liquid, and the single administration dosage is 120mg/kg/day.
Cinnamaldehyde nanoemulsion group (6): 6 of the BDL molded animals were taken as cinnamaldehyde nanoemulsion group (abbreviated as "nanoemulsion group"), and the cinnamaldehyde nanoemulsion of example 8 was administered in a dose of 120mg/kg/day by gavage 1 time per day starting on day 2 after the surgery.
cinnamaldehyde-Va drug-loaded nanoemulsion group (6): 6 of the BDL modeling animals are taken as a cinnamaldehyde-Va drug-loaded nanoemulsion group (called a drug-loaded group for short), and the cinnamaldehyde-Va drug-loaded nanoemulsion of the embodiment 18 is administrated by gavage 1 time every day from the 2 nd day after the operation, wherein the administration dose is 120mg/kg/day.
Sham group (Sham group, 6): fasting the experimental animals for 12 hours before operation; and (3) operation: after isoflurane anesthesia is carried out, the abdomen is opened under the aseptic operation condition, then the incision is sutured, and after the animal is anesthetized to be awake, the animal can eat normally and drink water freely; beginning on day 2 post-surgery, 1 saline was administered daily for gavage.
After 14 days of administration (or physiological saline), the above groups were fasted for 12 hours, and then samples of blood, bile, liver tissue, etc. were collected. Serum was taken for biochemical indicator detection of serum, and the detection results are shown in table 5. The serum biochemical index detection result shows that compared with a BDL model group, the nanoemulsion group and the drug-loaded group can both significantly reduce ALT, AST and TBA levels in serum, which indicates that the cinnamaldehyde nanoemulsion and the cinnamaldehyde-Va drug-loaded nanoemulsion can both significantly improve the liver function level of a BDL rat, and the cinnamaldehyde-Va drug-loaded nanoemulsion has a better in-vivo anti-hepatic fibrosis effect; and the contrast group of the bulk drugs has no obvious improvement on serum biochemical indexes. Alanine Aminotransferase (ALT), aspartate Aminotransferase (AST) and Total Bile Acid (TBA) are used to measure liver function.
TABLE 5
| Index (I) | Model set | Artificial operation group | Comparison group | Nano-emulsion group | Drug-loaded medicine |
| ALT | 113.57±15.27*** | 46.50±3.39 | 105.57±22.79 | 81.80±11.56## | 85.17±16.85## |
| AST | 577.43±115.23*** | 106.50±15.64 | 529.29±153.85 | 437.60±91.13# | 400.67±120.19# |
| TBA | 278.96±65.22*** | 48.52±41.38 | 254.69±64.37 | 243.38±47.36 | 204.15±54.70# |
Wherein, is expressed as significantly different P <0.001 compared to sham group; # indicates a significant difference compared to the model group, P <0.05; # indicates significant difference compared to model group, P <0.01.
Paraffin sections were prepared from the liver tissue samples of each group, and hematoxylin-eosin staining (H & E staining), sirius red staining, and Masson staining were performed, respectively, and the staining results are shown in fig. 3. The results show that: compared with the sham operation group, the hyperplasia and necrosis of the bile duct of the model group animal are obviously increased, which indicates that the model is successfully made; compared with the model group, the proliferation and necrosis of the bile duct of the control group are not obviously reduced; after the drug delivery, the nanoemulsion group and the drug-loaded group can improve the hyperplasia and the necrosis of the bile duct of the liver, and the improvement of the drug-loaded group is more obvious.
The collagen deposition in the liver can be seen by the sirius red staining, and the more the collagen deposition, the more serious the degree of liver fibrosis is. The model group can show serious collagen deposition, compared with the comparison group, the collagen deposition is not obviously reduced, the collagen deposition of the nanoemulsion group and the drug-loaded group after the drug is administered is obviously reduced, and the effect of the drug-loaded group is better.
Masson staining can reveal fibrous connective tissue in the liver, with more fibrous connective tissue proliferation evidencing higher degree of liver fibrosis. The model group can show severe fibroconnective tissue hyperplasia, compared with the comparative group, the comparative group does not obviously inhibit the fibroconnective tissue hyperplasia, the nanoemulsion group and the drug-loaded group can obviously inhibit the fibroconnective tissue hyperplasia after administration, and the drug-loaded group has better effect.
The section dyeing result shows that the cinnamaldehyde nanoemulsion and the cinnamaldehyde-Va drug-loaded nanoemulsion can improve the hepatic fibrosis degree of a BDL model rat, and the drug-loaded nanoemulsion has a better in-vivo hepatic fibrosis resistance effect. Wherein, the vitamin A is stored in the liver and has certain liver targeting property. From this, it is presumed that fat-soluble vitamins such as vitamin D, vitamin E, and vitamin K, and drugs stored or metabolized in the liver can also be used for preparing the drug-loaded nanoemulsion of the present invention.
The nano-emulsion and the drug-loaded nano-emulsion can be used as food or medicine, and can also be used for preparing anti-hepatic fibrosis drugs or food. Is used for prolonging the retention time of cinnamaldehyde and fat-soluble drugs in intestinal tracts and enhancing the intestinal absorption of the drugs, thereby enhancing the anti-hepatic fibrosis drug effect.
The above is only a preferred embodiment of the present invention, and is not intended to limit the present invention, and various modifications and changes will occur to those skilled in the art. Any modification, equivalent replacement, or improvement made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (10)
1. A cinnamaldehyde-based nanoemulsion characterized by comprising cinnamaldehyde, an emulsifier, and water.
2. The nanoemulsion of claim 1, further comprising a lipid-soluble drug.
3. The nanoemulsion of claim 1, wherein the lipid-soluble drug comprises valsartan or vitamin a.
4. The nanoemulsion of claim 3, wherein the mass ratio of cinnamaldehyde to the emulsifier to the vitamin A to the water is 12:6-18:1-4:100, respectively;
the mass ratio of the cinnamaldehyde to the emulsifier to the valsartan to the water is 60:60:6:500.
5. the nanoemulsion of claim 1, further comprising a co-emulsifier.
6. The nanoemulsion of claim 5, wherein the emulsifier comprises any one or a combination of the following ingredients: polyoxyethylene castor oil and polyoxyethylene hydrogenated castor oil;
the coemulsifier comprises: ethanol, propylene glycol, polyethylene glycol 400 or n-butanol.
7. The nanoemulsion of claim 1, wherein the nanoemulsion is prepared by a method comprising:
mixing cinnamaldehyde and an emulsifier uniformly to obtain a first oil phase system;
and dropwise adding water into the first oil phase system, and stirring to obtain the nanoemulsion.
8. The nanoemulsion of claim 7, wherein the preparation method of the nanoemulsion comprises:
mixing the cinnamaldehyde, the emulsifier and the fat-soluble medicine uniformly to obtain a second oil phase system;
and dropwise adding water into the second oil phase system, and stirring to obtain the drug-loaded nanoemulsion.
9. Use of a nanoemulsion according to any of claims 1-8, for the preparation of a drug or a food product against liver fibrosis.
10. The use according to claim 9, for prolonging the residence time of cinnamaldehyde and a lipid soluble drug in the intestinal tract and enhancing the intestinal absorption of the drug, thereby enhancing the anti-hepatic fibrosis effect.
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