CN112933080B - Application of elephantopus scaber lactone compound in preparing medicine with respiratory syncytial virus resisting effect - Google Patents
Application of elephantopus scaber lactone compound in preparing medicine with respiratory syncytial virus resisting effect Download PDFInfo
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- CN112933080B CN112933080B CN202110077893.XA CN202110077893A CN112933080B CN 112933080 B CN112933080 B CN 112933080B CN 202110077893 A CN202110077893 A CN 202110077893A CN 112933080 B CN112933080 B CN 112933080B
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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
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/365—Lactones
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
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Abstract
The invention relates to the technical field of medicinal chemistry, and particularly discloses an application of elephantolide compounds in preparing a medicament with an effect of resisting respiratory syncytial virus. The elephantopin lactone compound is selected from any one or more of elephantopin lactone, allopatricolor lactone, isodeoxyelephantopin lactone and deoxyelephantopin lactone. Experiments show that: the elephantopin lactone, the allopatricolor lactone, the isodeoxyelephantopin lactone and the deoxyelephantopin lactone all show certain respiratory syncytial virus resisting activity.
Description
Technical Field
The invention relates to the technical field of medicinal chemistry, in particular to application of elephantopin lactone compounds in preparing a medicament with an effect of resisting respiratory syncytial virus.
Background
Respiratory Syncytial Virus (RSV) infection is widespread worldwide, is universally susceptible to populations, and can occur as a result of repeated infections and co-infections with multiple Respiratory viruses. Thus, RSV is a common human pathogen and poses a threat to the health of newborns worldwide. The infection routes of RSV are mainly divided into air transmission and contact transmission, and the RSV can enter a human body through eyes, nose and throat, so that people or objects carrying RSV by contacting at a short distance have a certain infection risk, especially infants or people with low immunity. The clinical manifestations are mainly high fever, chest distress, shortness of breath, wheezing, cough and other upper respiratory tract infection symptoms, and long-term infection can cause viruses to enter lower respiratory tract to cause bronchiolitis, pneumonia and the like. Infants are one of the main population with lower respiratory tract infection, wherein pneumonia and bronchiolitis are one of the main causes of hospitalization and death of infants. In addition, the elderly and people with low immunity are also the main pathogens of lower respiratory tract infections. RSV is reported by the WHO to infect about 6.4 million people per year with a mortality rate of about 0.25%.
The safe and effective RSV vaccine can prevent the lower respiratory tract diseases of high-risk people caused by RSV infection, and reduce the hospitalization rate and the death rate. The formalin fire vaccine studied in the 20 th century was the first RSV vaccine, but it eventually ended up failing. Although a variety of vaccines, such as live attenuated vaccines, vector vaccines, subunit vaccines, etc., have been developed in the late stage, no safe and effective RSV vaccine has been developed yet for clinical use.
At present, the clinical medicines for resisting RSV infection are few in types, mainly ribavirin, palivizumab (Palivizumab) and some Chinese patent medicines with broad-spectrum antiviral effect. A large amount of clinical data show that the ribavirin has extremely strong side effects, is not suitable for pregnant women and children, and is mostly used for severe patients; the action mechanism of broad-spectrum antiviral Chinese patent medicines, such as lotus antipyretic granules/capsules, antipyretic and yanning capsules and the like, on RSV infection is not clear.
Therefore, there is an urgent need to develop further drugs having an anti-respiratory syncytial virus effect so as to provide more drug options for patients with different symptoms at different ages.
Elephantopus scaber seed lactone, allopatricolor seed lactone, isodeoxyelephantopus scaber lactone and deoxyelephantopus scaber lactone are known compounds separated in the research process of the anterior elephantopus scaber and elephantopus tomentosus of the subject group; for example, chinese patent CN111116603A also discloses a method for preparing isodeoxyelephantolide and deoxyelephantolide from elephantopus scaber. Although the group of subjects of the present invention reported that elephantopus scaber and elephantopus tomentosus have an antiviral effect in the previous studies; however, the study in the early stage of the subject group only reports that the caffeoylquinic acid component in the elephantopus scaber has the effect of resisting the respiratory syncytial virus; for example, patents CN102219687A and CN 102219686A in the previous stage of the subject group disclose that a series of caffeoylquinic acid components have the effect of resisting respiratory syncytial virus; before the invention is completed, the subject group does not find that the elephantopus scaber seed lactone, the allopatricolor seed lactone, the isodeoxyelephantopus scaber seed lactone and the deoxyelephantopus scaber seed lactone also have the effect of resisting respiratory syncytial virus; it is also unexpected that elephantopin lactone, allopatricolor lactone, isodesoxyelephantopin lactone and desoxyelephantopin lactone have respiratory syncytial virus resisting effect.
In the past, chinese patent CN 111848640A discloses the application of elephantopus scaber lactone compounds in the preparation of anti-inflammatory drugs; chinese patent CN 111084773A discloses the use of deoxyelephantolide or isodeoxyelephantolide in the preparation of anti-pulmonary fibrosis drugs; in document 1 (Xu G, liang Q, gong Z, et al. Anti tumor activities of the four seeds of bile lactones from Elephantopus scaber L [ J ]. Exp Oncol,2006,28 (2): 106-9), compounds such as Elephantopus scaber lactone, allopatricolor lactone, deoxyelephantopus lactone, isodeoxyelephantopus lactone, etc. extracted and separated from Elephantopus scaber were tested for activity against tumor cell growth in vitro. The result shows that elephantopin lactone, deoxyelephantopin lactone and isodeoxyelephantopin lactone obtained by extraction and separation from elephantopin have obvious antitumor activity; further, document 2 (Chan C K, chan G, awang K, et al. Deoxylephantopin from electrochemical cells inhibitors HCT116Human Colective Carbonisatus Cell Growth through Apoptosis and Cell Cycle arm [ J ]. Molecules,2016,21 (3): 385.), document 3 (Mehmood T, maryam A, ghramh H, et al, deoxylephantopin and Isodeoxylephantopin as Potential Anticancer Agents with Effects on Multiple signalling Pathways [ J ]. Molecules,2017,22 (6): 1013.), and document 4 (Verma S, rai V, awasthe N, et al, isodeoxylephantopin, a Sesquiterpen inductor ROS deoxygenization, supress NF-kappaB Activation, modulates LncRNA Expression and Exhibit Activities Agents approach [ J ]. Sci Rep.3763, 3763 × 3763 (1): 17980) also disclose anti-tumor activity of bile lactones and allophanolide.
In summary, the prior art does not disclose that the elephantopin lactone compound has antiviral effect, but only discloses that the elephantopin lactone compound has anti-inflammatory, anti-pulmonary fibrosis, anti-tumor effect and the like. Therefore, based on the prior art, the skilled in the art cannot expect that the elephantopus scaber lactone compound has an antiviral effect, and more specifically, the elephantopus scaber lactone compound has an anti-RSV virus effect, and especially, the elephantopus scaber lactone, the allopatricolor lactone, the isodeoxyelephantopus scaber lactone and the deoxyelephantopus scaber lactone have an anti-RSV virus effect.
Disclosure of Invention
In order to overcome the defects of the prior art in the development of anti-RSV medicaments, the invention provides the application of the elephantopus scaber lactone compound in the preparation of medicaments with the effect of resisting respiratory syncytial viruses.
The technical scheme of the invention is as follows:
the invention provides an application of a elephantopus scaber lactone compound in preparing a medicament with an effect of resisting respiratory syncytial virus, wherein the elephantopus scaber lactone compound is selected from any one or more than one of elephantopus scaber seed lactone, allopatricolor seed lactone, isodeoxyelephantopus scaber lactone and deoxyelephantopus scaber lactone.
Preferably, the elephantolide compound is selected from a mixture of isodeoxyelephantolide and deoxyelephantolide; wherein the weight ratio of the isodeoxyelephantopin lactone to the deoxyelephantopin lactone is 1-3:1.
Further preferably, the weight ratio of the isodeoxyelephantolide to the deoxyelephantolide is 2:1.
Preferably, the medicine contains a therapeutically effective amount of elephantopin lactone compounds and a pharmaceutically acceptable carrier.
Preferably, the medicament is prepared into powder, pills, tablets, capsules, oral liquid, aerosol or injection.
Preferably, the elephantopin lactone compound is separated from elephantopin scaber or elephantopin scaber.
The invention also provides a medicament for resisting respiratory syncytial virus, the active ingredients of which comprise any one or more than one of elephantopus scaber seed lactone, allopatricolor seed lactone, isodeoxyelephantopus scaber lactone and deoxyelephantopus scaber lactone.
Preferably, the effective components comprise isodeoxycholic acid and deoxyelephantolide; wherein the weight ratio of the isodeoxyelephantolide to the deoxyelephantolide is 1-3:1.
Further preferably, the weight ratio of the isodeoxyelephantolide to the deoxyelephantolide is 2:1.
Preferably, the medicament is in the form of powder, pills, tablets, capsules, oral liquid, aerosol or injection.
Has the advantages that: in the research process, the elephantopin lactone, the allopatricolor lactone, the isodeoxycholic acid lactone and the deoxyelephantopin lactone are surprisingly found to have the effect of resisting the respiratory syncytial virus; the application of elephantopin lactone, allopatricolor lactone, isodesoxyelephantopin lactone and desoxyelephantopin lactone in preparing the medicine with the function of resisting respiratory syncytial virus is provided for the first time; the inventor further researches show that the combination of the isodeoxycholic acid and the deoxycholic acid has a synergistic effect on resisting the respiratory syncytial virus, and the combination of the isodeoxycholic acid and the deoxycholic acid achieves a more excellent effect on resisting the respiratory syncytial virus.
Detailed Description
The present invention will be further explained with reference to specific examples, which are not intended to limit the present invention in any way.
EXAMPLE 1 Studies on anti-RSV Activity of Dichrolide Compounds
The anti-RSV activity of the elephantopinolide compound is tested by adopting a plaque reduction experiment method, and the specific method is as follows: (1) HEp-2 cells were plated in 24-well cell culture plates (1 mL per well, cell density 2X 10) 5 cell/mL), followed by 37 ℃ C., 5% CO 2 Culturing in an incubator until a cell monolayer grows; (2) 100 mu L of respiratory syncytial virus suspension with the concentration of 100 mu L and different drug concentration are added into each hole, and a cell control group and a virus control group are arranged at the same time; standing at 37 deg.C, 5% CO 2 Culturing in an incubator for 2h. The cross is gently shaken every 15min to ensure that the virus is uniformly and fully adsorbed and penetrates into cells; (3) After the virus is adsorbed for 2 hours, removing virus liquid, washing for 2 times by PBS, adding 0.5mL of agarose gel covering liquid into each hole, adding 0.5mL of medicine with corresponding concentration after the covering liquid is solidified, and adding equal-volume maintenance liquid into a cell control group and a virus control group; (4) Placing the 24-hole plate in a cell culture box for culturing for 4-5 days, adding 10% formaldehyde for fixing overnight, removing agarose gel, dyeing with 1% crystal violet for 30min, washing the 24-hole plate with tap water, and air dryingAnd counting the number of plaques. Calculating the plaque inhibition rate of the sample, and further calculating the median inhibition concentration IC50; plaque inhibition rate = [ (number of plaques of virus group-number of plaques of drug group)/number of empty of virus group]×100％。
The method is adopted to test the respiratory syncytial virus resistance activity of the following experimental group medicines; the test results are shown in Table 1.
Experimental group 1: elephantopus scaber seed lactone;
experimental group 2: allopatricolor bile lactone;
experimental group 3: isodeoxyelephantolide;
experimental group 4: deoxycholic acid lactone;
experimental group 5: the elephantopus scaber seed lactone and the allopatricopus scaber seed lactone are combined according to the mass ratio of 1:1;
experimental group 6: the elephantopus scaber seed lactone and the isodeoxyelephantopus scaber lactone are combined according to the mass ratio of 1:1;
experimental group 7: combining allopatricolor lactone and isodeoxyelephantolide 5363 in a mass ratio of 1:1;
experimental group 8: combining allopatricolor lactone and deoxyelephantopin lactone according to the mass ratio of 1:1;
experimental group 9: the combination of the isodeoxyelephantolide and the deoxyelephantolide in a mass ratio of 1:1;
experimental group 10: the combination of the isodeoxyelephantolide and the deoxyelephantolide in a mass ratio of 2:1;
experimental group 11: the combination of the isodeoxyelephantolide and the deoxyelephantolide according to the mass ratio of 3:1.
TABLE 1 results of anti-RSV activity test of elephantolide compounds
| Experimental group | Composition (I) | IC50(μg/mL) |
| Experimental group 1 | Didancao herb seed lactone | 25.45 |
| Experimental group 2 | Isoelephantopus scaber seed lactone | 30.29 |
| Experimental group 3 | Isodeoxyelephantolide | 3.17 |
| Experimental group 4 | Deoxycholic acid lactone | 10.25 |
| Experimental group 5 | Elephantopus scaber seed lactone =1:1 | 27.39 |
| Experimental group 6 | Elephantopus scaber seed lactone, isodeoxyelephantopus scaber lactone =1:1 | 15.39 |
| Experimental group 7 | Allopatricolol lactone, isodeoxyelephantolide =1:1 | 17.22 |
| Experimental group 8 | The allopatricolor lactone is deoxyelephantolor lactone =1:1 | 18.40 |
| Experimental group 9 | Isodeoxyelephantolide, deoxyelephantolide =1:1 | 1.62 |
| Experimental group 10 | Isodeoxyelephantolide, deoxyelephantolide =2:1 | 0.95 |
| Experimental group 11 | Isodeoxyelephantolide, deoxyelephantolide =3:1 | 1.37 |
As can be seen from the results of the RSV resistant activity tests of the experimental groups 1-4 in the table 1, the elephantopin lactone, the allopatricolor lactone, the isodeoxycholic lactone and the deoxyelephantopin lactone all have a certain respiratory syncytial virus resistant function; the isodeoxyelephantopinolide has the optimal effect of resisting respiratory syncytial virus, and the inhibition effect on the respiratory syncytial virus is far better than elephantopinolide, allopatricolol lactone and deoxyelephantopinolide.
As can be seen from the results of the anti-RSV activity tests of the experimental groups 5 to 11: only after the isodeoxyelephantolide and the deoxyelephantolide are combined, the synergistic effect of resisting the respiratory syncytial virus is achieved; the combination of the elephantopin lactone, the allopatricolor lactone, the isodeoxyelephantopin lactone and the deoxyelephantopin lactone does not show a synergistic effect against respiratory syncytial virus.
EXAMPLE 2 preparation of tablets
Mixing 1g of elephantopin, allopatricolor lactone, isodeoxyelephantopin and deoxyelephantopin with 27g of microcrystalline cellulose and 2g of magnesium stearate respectively, mixing, and making into tablet with weight of 300 mg/tablet with single punch.
EXAMPLE 3 preparation of tablets
Mixing 0.5g of isodeoxyelephantolide and deoxyelephantolide with 27g of microcrystalline cellulose and 2g of magnesium stearate respectively, mixing, and making into tablet with weight of 300 mg/tablet with single punch.
EXAMPLE 4 preparation of capsules
Mixing 1g of elephantopin, allopatricolor lactone, isodeoxyelephantopin and deoxyelephantopin with 27g of lactose and 2g of magnesium stearate, and making into capsule in an amount of 300mg per capsule.
EXAMPLE 5 preparation of capsules
Mixing 0.5g of isodeoxyelephantolide and deoxyelephantolide, 27g of lactose and 2g of magnesium stearate respectively, and filling 300mg of the mixture into capsules to prepare capsules.
Claims (6)
1. The application of the elephantopus scaber lactone compound in preparing the medicine with the effect of resisting respiratory syncytial virus is characterized in that the elephantopus scaber lactone compound is selected from any one or more than one of elephantopus scaber seed lactone, allopatricolor seed lactone, isodeoxyelephantopus scaber lactone and deoxyelephantopus scaber lactone.
2. The use of the elephantolide compounds according to claim 1 for the preparation of a medicament with anti-respiratory syncytial virus effect, wherein said elephantolide compounds are selected from the group consisting of isodeoxycholic and mixture of deoxycholic; wherein the weight ratio of the isodeoxyelephantolide to the deoxyelephantolide is 1-3:1.
3. The use of elephantopinolide compounds according to claim 2 in the preparation of a medicament with anti-respiratory syncytial virus effect, wherein the weight ratio of isodeoxyelephantopinolide to deoxyelephantopinolide is 2:1.
4. The use of the elephantolide compound according to claim 1 in the preparation of a medicament with anti-respiratory syncytial virus effect, wherein said medicament comprises a therapeutically effective amount of elephantolide compound and a pharmaceutically acceptable carrier.
5. The application of the elephantolide compound in preparing the medicine with the effect of resisting the respiratory syncytial virus according to claim 1, wherein the medicine is prepared into powder, pills, tablets, capsules, oral liquid, aerosol or injection.
6. The use of the elephantolide compounds according to claim 1 in the preparation of a medicament having an anti-respiratory syncytial virus effect, wherein the elephantolide compounds are isolated from elephantopus scaber or elephantopus tomentosus.
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| CN202110077893.XA CN112933080B (en) | 2021-01-20 | 2021-01-20 | Application of elephantopus scaber lactone compound in preparing medicine with respiratory syncytial virus resisting effect |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN102219686A (en) * | 2011-04-22 | 2011-10-19 | 暨南大学 | Caffeoyl derivative and use of coffeeoyl derivative in preparing drugs against respiratory syncytial viruses |
| CN102219687B (en) * | 2011-04-22 | 2013-09-04 | 暨南大学 | Elephantopus scaber extract as well as preparation method and applications thereof in preparing antiviral drugs |
| CN111084773B (en) * | 2020-01-03 | 2022-06-07 | 仁合熙德隆药业有限公司 | Application of desoxyelephantolide or isodesoxyelephantolide in preparation of anti-pulmonary fibrosis drugs |
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