CN113855688A - Application of Vina-ginsenoside R18 in preparation of anti-dengue virus pharmaceutical preparation - Google Patents
Application of Vina-ginsenoside R18 in preparation of anti-dengue virus pharmaceutical preparation Download PDFInfo
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- CN113855688A CN113855688A CN202111367196.4A CN202111367196A CN113855688A CN 113855688 A CN113855688 A CN 113855688A CN 202111367196 A CN202111367196 A CN 202111367196A CN 113855688 A CN113855688 A CN 113855688A
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- A61K31/7034—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin
- A61K31/704—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin attached to a condensed carbocyclic ring system, e.g. sennosides, thiocolchicosides, escin, daunorubicin
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Abstract
The invention discloses a dammarane type tetracyclic triterpene monomer compound vina-ginsenoside R18:
Description
Technical Field
The invention relates to application of vina-ginsenoside R18 in preparation of a dengue virus resistant pharmaceutical preparation, and belongs to the technical field of antiviral.
Background
Dammarane-type tetracyclic triterpene compounds are main components of Panax ginseng (Panax ginseng) and Panax notoginseng (Panax notoginseng) belonging to Araliaceae. Modern researches show that the dammarane type tetracyclic triterpene compounds have various pharmacological effects of resisting virus, resisting tumor, regulating immunity, resisting oxidation and the like. In the aspect of antivirus, the compounds can obviously inhibit the replication of various viruses such as hepatitis C virus (Hepatology,2017,66: 758-. A dammarane type tetracyclic triterpene monomer compound vina-ginsenoside R18 is separated from pseudo-ginseng, and pharmacological actions related to the virus resistance of the compound are not reported in research.
Dengue virus (DENV) belongs to a member of the flaviviridae family of the flaviviridae genus, and members of the same genus include: japanese encephalitis virus, West Nile virus, St.Louis encephalitis virus, yellow fever virus, etc. The virus has an RNA genome capsid in the shape of a dumbbell, rod or sphere with a diameter of 40-50 nm. Can be cultured and propagated in brain and tissue cells of mice, and is most sensitive to Aedes albopictus pure cell strain (C6/36). Dengue virus has 1-4 serotypes, wide serological cross reaction exists among the serotypes, and abnormal secondary infection can cause the phenomenon of antibody-dependent infection enhancement (ADE).
Dengue virus (DENV) infection is the most prevalent arbovirus disease in humans today. According to WHO estimates that 25-30 million people worldwide face the risk of Dengue virus infection, about 5 million to 1 million cases of Dengue Fever (DF) occur each year, and patients show symptoms of high fever, headache, myalgia, arthralgia and rash, and 50 million of the cases develop more serious Dengue Hemorrhagic Fever (DHF) and Dengue Shock Syndrome (DSS), with the mortality rate of 5% -10%. The virus is transmitted from person to person primarily through aedes aegypti and aedes albopictus. The virus is mainly prevalent in more than one hundred countries and regions, such as southeast Asia, America, eastern Mediterranean, Africa, etc.
According to the estimation of the world health organization, about 5 million to 1 hundred million people worldwide infect dengue fever virus to cause dengue fever, and the clinical symptoms are mainly shown as follows: fever, rash, headache and myalgia; dengue virus infectors may develop more serious conditions, dengue hemorrhagic fever and dengue shock syndrome, with about 25 to 50 million people statistically expressing dengue hemorrhagic fever every year worldwide. Dengue fever is also popular in China in a large scale, severe epidemic is outbreaked in Guangdong province in 2014, and the number of the outbreaks reaches 47143; outbreaks again in 2019, and the number of the disease people in China reaches 22599. Dengue has become a major public health problem in our country and even the world.
Along with the change of global climate, the acceleration of urbanization process, frequent communication of personnel and the increase of labor personnel in dengue epidemic areas in China, the threat of dengue virus epidemic still exists, and the climate and environment of partial areas in China are suitable for the survival of the transmission medium of the dengue virus, thereby providing conditions for the transmission of the virus.
At present, no effective vaccine or drug is available for preventing and treating diseases caused by dengue virus, so that the search for effective anti-dengue virus drugs is of great significance.
Disclosure of Invention
In order to solve the technical problems, the pharmacology of resisting the dengue virus is further researched, and the vina-ginsenoside R18 is found to have an antiviral effect and can obviously inhibit the replication of the dengue virus.
Therefore, one of the objects of the present invention is to provide the use of vina-ginsenoside R18 in the preparation of a pharmaceutical formulation against dengue virus.
Another objective of the invention is to provide an anti-dengue virus pharmaceutical preparation, which comprises a therapeutically effective amount of vina-ginsenoside R18, and also comprises pharmaceutic adjuvants or other compatible medicines.
The above medicinal adjuvants refer to conventional medicinal excipient, such as solvent, disintegrating agent, correctant, antiseptic, colorant and binder, or their combination.
The other compatible medicines are prepared by taking vina-ginsenoside R18 with effective dose as a raw material and then adding other natural medicines or chemicals with anti-inflammatory, immune enhancement or antiviral activity.
Wherein the anti-inflammatory drug is selected from: (1) acetylsalicylates including aspirin and the like; (2) non-acetylsalicylate including magnesium salicylate, sodium salicylate, choline magnesium salicylate, diflunisal (diflunisal), salsalate; (3) non-salicylates including ibuprofen, indomethacin (indomethacin), flurbiprofen, phenoxyibuprofen, naproxen, nabumetone (naproxone), piroxicam (piroxicam), phenylbutazone, diclofenac, fenprofen, ketoprofen, ketorolac, tetrachlorofenamic acid, sulindac, tolmetin, and the like.
The immune enhancing drug is selected from: levamisole (LMS), interleukin 2 (TCGF), Interferon (IFN), Transfer Factor (TF), thymosin (thymosin), cyclosporine (cyclosporine a), and extracts from ginseng, astragalus, schisandra, wolfberry, codonopsis pilosula, cordyceps sinensis, ganoderma lucidum and tremella, etc.
The antiviral active agent is selected from: (1) non-ring-opening nucleosides including Zidovudine (Zidovudine), Stavudine (Stavudine), Lamivudine (Lamivudine), Zalcitabine (Zalcitabine), and the like; (2) open-ring nucleosides including acyclovir (Aciclovir), Ganciclovir (Ganciclovir), Penciclovir (Penciclovir), Famciclovir (Famcclovir), Adefovir Dipivoxil (Adefovir Dipivoxil); (3) non-nucleosides including Nevirapine (Nevirapine), Efavirenz (Efavirenz); (4) protease inhibitors including Saquinavir (Saquinavir), Indinavir (Indinavir), Nelfinavir (Nelfinavir); (4) other types, including Ribavirin (Ribavirin), Amantadine Hydrochloride (Hydrochloride), Rimantadine Hydrochloride (Hydrochloride), foscarnet sodium, and Oseltamivir Phosphate (Oseltamivir Phosphate), among others.
It is another object of the present invention to provide a pharmaceutical composition comprising vina-ginsenoside R18 as an active ingredient.
The invention also provides an anti-dengue virus medicine, which at least comprises vina-ginsenoside R18 with effective treatment amount and pharmaceutically acceptable auxiliary materials.
Preferably, the pharmaceutical composition of the present invention comprises 0.1 to 99.9% by weight of vina-ginsenoside R18 as an active ingredient, more preferably 0.15 to 20% by weight of vina-ginsenoside R18 as an active ingredient, more preferably 0.2 to 10% by weight of vina-ginsenoside R18 as an active ingredient, more preferably 0.4 to 5% by weight of vina-ginsenoside R18 as an active ingredient.
The acceptable auxiliary materials do not damage the pharmaceutical activity of the vina-ginsenoside R18 of the invention, and the effective dosage thereof, namely the dosage when the pharmaceutical carrier acts, is nontoxic to human body.
The acceptable excipients include, but are not limited to: lecithin, aluminum stearate, alumina, ion exchange materials, self-emulsifying drug delivery systems, tweens or other surfactants, serum proteins, buffer substances such as phosphates, glycine, sorbic acid, water, salts, electrolytes such as protamine sulfate, disodium hydrogen phosphate, potassium hydrogen phosphate, sodium chloride, zinc salts, magnesium silicate, mixtures of saturated fatty acid partial glycerides, and the like.
Other conventional pharmaceutical adjuvants such as binder (e.g. microcrystalline cellulose), filler (e.g. starch, glucose, anhydrous lactose and lactose beads), disintegrant (e.g. crosslinked PVP, croscarmellose sodium, low-substituted hydroxypropylcellulose), lubricant (e.g. magnesium stearate), and absorption enhancer, adsorption carrier, flavoring agent, sweetening agent, excipient, diluent, wetting agent, etc.
The present invention further provides a pharmaceutical composition comprising vina-ginsenoside R18 as an active ingredient according to claim 1, and a pharmaceutically acceptable carrier, excipient or diluent.
The medicinal excipient comprises one or more of solvent, disintegrant, correctant, antiseptic, colorant and binder.
The vina-ginsenoside R18 and pharmaceutical compositions thereof according to the present invention can be prepared according to conventional methods in the art and can be administered by enteral or parenteral or topical routes. Wherein the intestinal administration preparation comprises capsule, tablet, oral liquid, granule, pill, powder, pellet, paste, etc.; parenteral preparations include injections and the like; formulations for topical administration include creams, patches, ointments, sprays, and the like.
The administration route of the vina-ginsenoside R18 and the pharmaceutical composition thereof can be oral, sublingual, transdermal, intramuscular or subcutaneous, skin mucosa, vein, urethra, vagina and the like.
Compared with the prior art, the invention has the following advantages and technical effects:
the vina-ginsenoside R18 has strong in-vitro anti-dengue virus activity, can block 2-type dengue virus from being adsorbed to host cells, effectively block 2-type dengue virus from entering the host cells, can remarkably inhibit 2-type dengue virus from being replicated in the cells, has an obvious inhibiting effect on the synthesis of virus E protein and NS1 protein in the replication process of 2-type dengue virus, and indicates that the compound has good medicinal prospect.
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FIG. 1 shows the MTT method for detecting drug toxicity.
FIG. 2 shows the pathological effect of cells under microscope (40 times) and the death of cells detected by CCK8 method.
FIG. 3 shows the pathological effect of cells under microscope (40 times) and the death of cells detected by CCK8 method.
FIG. 4 shows the pathological effect of cells under a microscope (40 times) and the death of cells detected by the CCK8 method.
FIG. 5 shows the expression level of viral proteins observed under a confocal microscope (400-fold).
Detailed Description
The present invention will be described in further detail with reference to examples and drawings, but the present invention is not limited thereto.
The vina-ginsenoside R18 used in the examples of the present invention is prepared by separating ginseng or notoginseng (certified by medical college of Chinese university) from plant Araliaceae, and its structure is identified by UV, MS, NMR and other spectral methods, and its purity is more than 98% by HPLC-DAD peak area normalization method.
Example 1 toxicity of Vina-ginsenoside R18 on BHK-21 cells
Test method BHK-21 cells in logarithmic growth phase were taken at 1X 105The cell density of each/mL is inoculated in a 96-well plate, each well is 100 mu L, a control group and a drug group with different concentrations are arranged, and the cytotoxicity is detected by adopting an MTT method after 4 days.
The results of the experiment in FIG. 1 show that Vina-ginsenoside R18 has a half inhibitory concentration of 54.11. mu.M on BHK-21 cells and is substantially non-toxic to cells at a concentration of 25. mu.M.
Example 2Vina-ginsenoside R18 blocks the adsorption of dengue virus type 2 to host cells
Test method BHK-21 cells in logarithmic growth phase were taken at 1X 105Cell density per mL was seeded in 96-well plates at 100 μ L per well. The model group was infected with 200PFU of DENV-2, the drug group was administered 200PFU of DENV-2 and vina-ginsenoside R18(6.25, 12.5, 25 μ M) at the same time, cultured at 4 deg.C for 1h, virus and drug solution were discarded, 2% maintenance solution was added, and the mixture was placed at 37 deg.C and 5% (v/v) CO2The cultivation is continued in the incubator. After 4d, the blocking effect of the drug on the attachment of the type 2 dengue virus to the host cell was confirmed by observing cytopathic and death conditions.
The results of the experiment in FIG. 2 show that Vina-ginsenoside R18 dose-dependently blocks dengue virus type 2 from adsorbing to the host cell.
Example 3Vina-ginsenoside R18 blocks entry of dengue virus type 2 into host cells
Test method BHK-21 cells in logarithmic growth phase were taken at 1X 105Cell density per mL was seeded in 96-well plates at 100 μ L per well. The model group and the drug group were infected with 200PFU of DENV-2, cultured at 4 ℃ for 1h, and then virus was discarded, and the drug group was administered with vina-ginsenoside R18(6.25, 12.5, 25. mu.M), and then placed in a container of 37℃、5％(v/v)CO2The culture box of (2) for 1 h. Then the liquid medicine is discarded, 2 percent maintenance liquid is added, and the mixture is continuously put into an incubator at 37 ℃ for culture. The blocking effect of the drug on the entry of dengue-2 virus into the host cells was determined by observing cytopathic and death after 4 d.
The results of the experiment in FIG. 3 show that Vina-ginsenoside R18 is effective in blocking dengue virus type 2 from entering the host cell.
Example 4Vina-ginsenoside R18 inhibits dengue virus type 2 replication in cells
Test method BHK-21 cells in logarithmic growth phase were taken at 1X 105Cell density per mL was seeded in 96-well plates at 100 μ L per well. The model group and the drug group were infected with 200PFU of DENV-2 respectively and placed at 37 ℃ and 5% (v/v) CO2After culturing for 1h in the incubator of (1), the virus was discarded, and the drug group was administered with vina-ginsenoside R18(6.25, 12.5, 25. mu.M) or RV (20. mu.M), and placed at 37 ℃ with 5% (v/v) CO2The culture is continued in the incubator, and after 4d, the inhibition effect of the drug on the replication of the type 2 dengue virus in the cells is determined by observing the pathological changes and death conditions of the cells.
The experimental results of fig. 4 show that Vina-ginsenoside R18 can significantly inhibit the replication of dengue virus type 2 in cells.
Example 5Vina-ginsenoside R18 inhibits viral protein synthesis during dengue virus type 2 replication
Test method BHK-21 cells in logarithmic growth phase were taken at 1X 105Cell density per mL was seeded in confocal culture dishes at 1mL per dish. The model group and the drug group were infected with 200PFU of DENV-2 respectively and placed at 37 ℃ and 5% (v/v) CO2After culturing for 1h in the incubator of (1), the virus was discarded, and the drug group was administered with vina-ginsenoside R18 (25. mu.M) or RV (20. mu.M), and placed at 37 ℃ with 5% (v/v) CO2The culture was continued in the incubator, and after 2d, the expression of the viral E protein and NS1 protein was observed by confocal microscopy.
The test result of fig. 5 shows that Vina-ginsenoside R18 has obvious inhibition effect on the synthesis of virus E protein and NS1 protein during the replication of dengue virus type 2.
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 (10)
- Application of vina-ginsenoside R18 in preparation of anti-dengue virus pharmaceutical preparations.
- 2. The use according to claim 1, wherein the medicament comprises a therapeutically effective amount of vina-ginsenoside R18 and a pharmaceutically acceptable excipient.
- 3. The use according to claim 2, wherein the pharmaceutical formulation further comprises a drug compatible with vina-ginsenoside R18.
- 4. The use according to claim 1, wherein the anti-dengue virus drugs are all formulated as capsules, granules, tablets, injections, liposomal nanoparticles, sustained release agents, controlled release agents or dispersible tablets.
- 5. A pharmaceutical composition comprising vina-ginsenoside R18 as an active ingredient according to claim 1, and a pharmaceutically acceptable carrier, excipient or diluent.
- 6. The composition of claim 5, wherein the pharmaceutically acceptable excipient comprises one or a combination of two or more of a solvent, a disintegrant, a flavoring agent, a preservative, a coloring agent, and a binder.
- 7. The composition according to claim 5, which can be prepared according to the conventional methods in the art and can be administered by the enteral or parenteral or topical route.
- 8. The composition of claim 7, wherein the enterally administrable formulation is a capsule, tablet, oral liquid, granule, pill, powder, pellet, or ointment.
- 9. The composition of claim 7, wherein the parenteral formulation is an injection.
- 10. The composition of claim 7, wherein the topical route of administration formulation is a cream, patch, ointment, or spray.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114933626A (en) * | 2022-04-27 | 2022-08-23 | 云南大学 | Ginsenoside Rb 1 Derivatives and uses thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2019098787A1 (en) * | 2017-11-17 | 2019-05-23 | 한국화학연구원 | Arbovirus infection inhibitor |
| CN112689510A (en) * | 2020-03-31 | 2021-04-20 | 菲尼克斯生物技术公司 | Methods and compositions for treating coronavirus infection |
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- 2021-11-18 CN CN202111367196.4A patent/CN113855688A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2019098787A1 (en) * | 2017-11-17 | 2019-05-23 | 한국화학연구원 | Arbovirus infection inhibitor |
| CN112689510A (en) * | 2020-03-31 | 2021-04-20 | 菲尼克斯生物技术公司 | Methods and compositions for treating coronavirus infection |
Non-Patent Citations (2)
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| POWERS CN等: "An In-Silico Investigation of Phytochemicals as Antiviral Agents Against Dengue Fever", 《COMB CHEM HIGH THROUGHPUT SCREEN》 * |
| RU-FENG WANG等: "Chemical transformation and target preparation of saponins in stems and leaves of Panax notoginseng", 《J GINSENG RES.》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114933626A (en) * | 2022-04-27 | 2022-08-23 | 云南大学 | Ginsenoside Rb 1 Derivatives and uses thereof |
| CN114933626B (en) * | 2022-04-27 | 2024-02-09 | 云南大学 | Ginsenoside Rb 1 Derivatives and uses thereof |
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