CN107753480B - Application of praeruptorin in preparation of drug for protecting liver injury - Google Patents
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Abstract
The invention relates to 1 coumarin compound praeruptorin separated and prepared from peucedanum praeruptorum and application thereof in preparing drug-induced liver injury protection drugs and health products. Through in vivo and in vitro experimental research, the peucedanum praeruptorum dunn monomer compound is found to have pharmacological activity of resisting drug-induced liver injury for the first time. The chemical components have good drug-resistant liver injury effect, and are beneficial to research and development of novel drug-resistant liver injury protection drugs and health care products.
Description
Technical Field
The invention relates to the field of medicines, in particular to application of an effective coumarin monomer compound praeruptorin in the traditional Chinese medicine of peucedanum praeruptorum in preparing a medicine for protecting liver injury.
Background
The liver is the largest digestive gland in the human body, dominates the metabolism of the human body and is a huge 'chemical plant' in the human body. Liver damage is a common pathological condition of many liver diseases, and is mainly manifested by hepatocyte necrosis or apoptosis, hepatocyte degeneration, hepatocyte steatosis, cholestatic damage and inflammatory reaction. Long-term liver injury is an important factor causing liver fibrosis, even liver cirrhosis and liver cancer.
Among the investigated people in China, the number of the liver injury reaches 1.3 hundred million, and the number of the death people is nearly 50 million due to the liver injury disease. In recent years, with the rapid increase of the types of clinical medicines and the increase of the probability of self-administration or random increase of the dosage of the medicines of patients, the incidence rate of the hepatic injury caused by the medicines is correspondingly increased, and more than 900 medicines (such as carbon tetrachloride, bromobenzene, halothane, antituberculosis drugs, antibiotics, non-steroidal anti-inflammatory drugs and the like) are determined to cause the hepatic injury caused by the medicines according to statistics. Drug-induced liver injury has seriously threatened human health and life, and the protection of liver health is an unbearable task in front of us.
Modern medicine does not have specific medicines for treating liver injury, mostly adopts rest, diet adjustment, vitamin supplement and symptomatic treatment (antiviral medicines, immunoregulation medicines and liver protection and enzyme reduction medicines are selected), and severe patients need to be forced to stop taking medicines so as to avoid liver injury. The traditional Chinese medicine and the preparation thereof are quite common in China for treating liver diseases at present, modern pharmacological research shows that a plurality of traditional Chinese medicines (including compound medicines, single medicinal materials and monomer components) can effectively treat or improve liver injury diseases, and the traditional Chinese medicines gradually and widely pay attention to the liver-protecting effect, small toxic and side effects and multi-component and multi-target effects.
Radix Peucedani is the dried root of Peucedanum praeruptorum Dunn of Umbelliferae, and has effects of lowering qi, eliminating phlegm, dispelling pathogenic wind and clearing heat. Can be used for treating lung heat, phlegm stagnation, affection of exogenous wind-heat, cough, asthma, excessive phlegm, yellow and viscous phlegm, fullness and stuffiness in chest and diaphragm, etc.; its main pharmacological actions include resisting myocardial ischemia, resisting oxidation, resisting tumor, resisting bacteria, resisting inflammation, reducing blood pressure, relieving cough and eliminating phlegm, etc. The radix Peucedani mainly contains coumarins, and angular dihydropyrane coumarins as effective components, such as praeruptorin A, praeruptorin B, praeruptorin C, praeruptorin D, and praeruptorin E. Recent researches prove that the main pharmacological effects of the coumarin components of the peucedanum include bacteriostasis, antioxidation, anti-inflammation, anti-tumor, myocardial protection, phlegm elimination, cough relieving and the like (inner Mongolian medicine, 2017, 2 (3): 142-. In addition, it has been found that peucedanum praeruptorum dunn has pharmacological activity against hyperlipidemia, hyperglycemia, nonalcoholic fatty liver disease, type 2 diabetes and the like (patent application No. 201710046028.2).
In addition, the coumarin compounds also widely exist in other traditional Chinese medicines (such as notopterygium root, angelica dahurica, fructus cnidii, fructus psoraleae and the like), and researches show that the coumarin compounds have various biological activities, such as HIV resistance, cancer resistance, blood pressure reduction, arrhythmia resistance, osteoporosis resistance, bacteria resistance and the like (Chinese traditional medicine journal, 2005, 30 (6): 410-414; Chinese new medicine journal, 2013, 22 (20): 2392-. In addition, some coumarin compounds have liver protection activity, including osthole (Chinese medicine pharmacology and clinic, 2006, 22 (2): 21-22), corallin (Arch Pharm Res, 1993,16 (1): 13-17) and 8-methoxy psoralen (Chinese modern application pharmacy, 2012, 29 (8): 682-; it is also found that 5 furocoumarins in Changium smyrnioides root bark have the activity of inhibiting liver cancer cell proliferation (Chinese J.T. J.Med., 2012, 18 (6): 203-.
However, until now, no report has been made on the pharmacological action of Peucedanum praeruptorum Linn on drug-induced liver injury.
Disclosure of Invention
The invention aims to provide application of an effective monomer compound of radix peucedani in preparing a drug for protecting liver injury.
The compound researched by the invention relates to 1 angular dihydropyranocoumarin compound separated and prepared from the Chinese medicinal material peucedanum praeruptorum, and the compound has the following chemical structure, can be separated and prepared from natural medicines, and can also be prepared by chemical synthesis.
The invention is realized by investigating the compound pair carbon tetrachloride (CCl)4) The survival rate of primary hepatocytes of injured suckling mice, the influence of alanine Aminotransferase (ALT), aspartate Aminotransferase (AST), Malondialdehyde (MDA) and superoxide dismutase (SOD), and the effect of praeruptorin on drug-induced liver injury is found for the first time.
The invention examines the compound pair CCl4ALT and AST contents in blood serum of an injured mouse, liver morphology, influences of liver index, MDA, SOD and Glutathione (GSH) in liver, and influences of MDA, ATP enzyme activity and membrane potential in liver cell mitochondria, and the peucedanum praeruptorum dunn is found to have the effect of resisting drug-induced liver injury for the first time.
Pharmacological experiments show that the pharmacological activity of 1 effective monomer component in the peucedanum praeruptorum dunn for resisting drug-induced liver injury can be used for preparing drugs and health care products with corresponding effects, and the research and development of novel drug-induced liver injury protection drugs and health care products are facilitated.
The medicament can be any pharmaceutically acceptable dosage form, including tablets, capsules, oral liquid, syrup, granules, pills, powder, ointment, pellets, injection, suppositories, creams, sprays, dripping pills, patches, sustained-release preparations, controlled-release preparations and the like.
The oral liquid preparations may be in the form of aqueous or oily solutions, suspensions, emulsions, syrups or elixirs, which may contain conventional additives, including solvents such as water, ethanol and the like, suspending agents such as sorbitol, syrup, methyl cellulose, gelatin, hydroxyethyl cellulose and the like, emulsifying agents such as lecithin, sorbitan monooleate, acacia and the like, and preservatives such as p-hydroxybenzoic ester, propylparaben, sorbic acid and the like.
The oral solid preparation may contain conventional excipients such as binders, fillers, diluents, lubricants, disintegrants, coloring agents, flavoring agents and wetting agents, and fillers suitable for coating tablets if necessary include cellulose, mannitol, lactose and other similar fillers. Suitable disintegrants include starch, polyvinylpyrrolidone and starch derivatives, such as sodium starch glycolate. Suitable lubricants include magnesium stearate. Suitable wetting agents include sodium lauryl sulfate.
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FIG. 1 test monomer Compound Pair CCl4The effects of pathological changes of liver tissue of injured mice
FIG. 1 pathological changes of mouse liver (. times.200) in normal group (A), model group (B), silibinin group (C), praeruptorin 8mg/kg group (D), praeruptorin 16mg/kg group (E), praeruptorin 32mg/kg group (F)
The normal group liver tissue structure is clear and visible, the liver cells are arranged in order and have consistent size, the liver cell cables are obviously radial, and the sink area has no pathological changes such as degeneration, necrosis, inflammatory cell infiltration and the like; the liver cells of the mouse in the model group are obviously edematous, ballooning, disorderly arranged liver cords, and have punctate necrosis, and the liver parenchyma has more inflammatory cell infiltration; the visible inflammatory cell infiltration of the liver tissue of the silybin group is obviously reduced compared with that of the model group, and the liver cells have no obvious change; the dose groups of peucedanum praeruptorin have different degrees of inflammatory cell infiltration, but are obviously reduced compared with the model group.
Detailed Description
In order to better explain the substance content of the invention which can be used for preparing the drug for protecting liver injury and the health care product, the invention is further explained by the specific experimental examples. The following examples are illustrative and are not intended to limit the invention in any way.
Example 1: effect of test monomeric Compounds on carbon tetrachloride-injured primary hepatocytes of suckling mice
1 materials, reagents and apparatus
1.1 Main materials and reagents
The test compound controls (Peucedanum praeruptorum, Silibinin) were purchased from Doppel Biotechnology, Inc.; l-02 cells (Shanxi Yuan Biotech Co., Ltd.); DMEM/F12 medium (Gibco, USA); fetal bovine serum (Gibco, USA); CCK-8 cell proliferation assay kit (Solebao Biotechnology Co., Ltd.); carbon tetrachloride (CCl)4) (Sigma); penicillin streptomycin double antibody (Gibco, USA); PBS (sulibao biotechnology limited); 96-well cell culture plates (Thermo corporation); 0.22um filters (Corning); blood counting plates (dandri scientific medical supplies factory, zhenjiang); ALT, AST, SOD and MDA detection kit (Nanjing institute of bioengineering).
1.2 Main instruments
5％CO2Incubator (Thermo corporation); table centrifuges (Changshan instrument centrifuge instruments, Inc.); biosafety cabinets (suzhou decontamination equipment ltd); microplate reader (TECAN); -80 ℃ refrigerator (Thermo company).
2 method
2.1 preparation of test sample solution
An appropriate amount of each test compound control is dissolved in DMSO, and the test sample dissolved in DMSO is diluted to a desired concentration with physiological saline.
2.2 modeling and drug delivery
Cell plating: resuspend the cells to a concentration of 1X 10510000 cells (100. mu.L) per well per mL, 3 replicates of cell placement, 37℃5％CO2After 12h of culture, each experimental drug was treated for 24 h. Then, a final concentration of 10mmol/LCCl was added per well4Placing at 37 ℃ with 5% CO2And culturing for 6 h.
The experimental groups included: blank (medium only); a normal group; solvent control (1 ‰ DMSO); solvent control + CCl4(model group); silybin group (concentration 60. mu. mol/mL) + CCl4(positive control group); peucedanum praeruptorum dunn (concentration 80. mu. mol/mL, 160. mu. mol/mL, 320. mu. mol/mL) + CCl4。
2.3 cell viability assay (CCK-8 method)
Changing 100. mu.L/well serum-free medium, adding 10. mu.L/well CCK-8 stock solution, 5% CO2The mixture is incubated in an incubator for 2h, and the absorbance at 450nm is measured.
2.4 determination of ALT, AST, MDA, SOD content
The assay was performed according to the specific procedures of the kit instructions.
2.5 calculation and statistics
Cell viability (% relative number of viable cells) — a (dosed) -a (blank)/a (0 dosed) -a (blank) × 100;
SPSS17.0 software calculated and counted ANOVA one-way variance analysis significant differences (P < 0.05).
3 results of the experiment
Compound pair CCl4Influence of injured suckling mouse primary hepatocyte survival rate, ALT, AST, MDA and SOD
Silibinin (positive control) can play a role in protecting liver cells, and the research shows that the silybin can obviously improve CCl4The survival rate of the damaged liver cells, the ALT, AST and MDA contents and the SOD content are obviously reduced, which indicates that the cell pathological model is reliable. Compared with the model group, the CCl can be obviously improved in each dose group of the praeruptorin4The survival rate of the damaged liver cells can be obviously reduced, and the ALT and AST contents can be obviously reduced; meanwhile, the dose groups of 80 mug/mL and 160 mug/mL of peucedanum praeruptorum dunn can also obviously increase the SOD content and obviously reduce the MDA content. The results indicate that the compound has anti-drug liver injury activity (table 1).
TABLE 1 test Compound vs CCl4The influence of primary hepatocytes survival, ALT, AST, MDA, SOD in the injured suckling mice (n ═ 3,
)
in comparison with the set of models,#P<0.05，##P<0.01，###P<0.001。
example 2: influence of tested monomeric compound on various indexes of mouse liver and serum damaged by carbon tetrachloride
1 materials, reagents and apparatus
1.1 animals
The male clean-grade Kunming mouse of 5-6 weeks old weighs 18-22 g, is purchased from Liaoning Changsheng biotechnology Limited company, and has a quality qualification certificate number: SCXK (Liao) 2015-0001. Before the experiment, all animals were adapted to 3 days. During the acclimatization period, animals had free access to food and free access to water. Keeping the breeding room quiet, keeping the indoor temperature at 23-25 ℃, keeping the humidity at 55% -75%, lighting by a fluorescent lamp, keeping the lighting for 12h and dark for 24h every day.
1.2 Main materials and reagents
The tested compound control (praeruptorin and silibinin) is purchased from Dolpheder biotechnology, Inc.; ALT, AST, MDA, SOD, GSH, Na+-K+-ATPase, Ca2+-Mg2+ATP enzyme assay kits are purchased from Nanjing institute of bioengineering; the BCA protein concentration determination kit is purchased from Biyuntian biotechnology research institute; CCl4And (5) analyzing and purifying.
1.3 Main instruments
MilllI-Q ultrapure water system (Millipore, USA); electron analytical balance, PB-10pH meter (Sartorius, Germany); glass homogenizers (Ningbo Xinzhi Biotech, Inc.); UV-1800PC type UV-visible spectrophotometer (soaring technologies, Inc. Shanghai); infinite M200Pro multifunctional enzyme-linked immunosorbent assay (Dongshen Innovative biotechnology limited)Company);
plus384 light-absorbing microplate reader (Molecular Devices, usa); HR/16M high speed refrigerated centrifuge (Hunan Hexi instrumentation, Inc.).
2 method of experiment
Male mice of Kunming species, randomly divided into 6 groups of 10 mice each, normal (normal saline) and model (0.1% CCl)4Peanut oil), silibinin (positive control group, 16mg/kg), and praeruptorin low-medium dosage group (8mg/kg, 16mg/kg, 32 mg/kg); each group of mice was gavaged with 10mL/kg for 7 days 1 time a day, and the molding was started 1h after the last administration. Mixing CCl4Dissolving in peanut oil to obtain 0.1% CCl4And (3) carrying out intraperitoneal injection on the peanut oil solution according to the dose of 10mL/kg, and establishing a mouse acute liver injury model. Normal groups were injected intraperitoneally with equal amounts of peanut oil.
After poisoning, fasting is performed without water prohibition, 16h later, the eyeball is picked to take blood, the whole blood is placed at room temperature for 2h, and then serum is separated and stored at-80 ℃ for later use; immediately taking blood, removing cervical vertebra to kill the mouse, quickly dissecting liver, rinsing with 4 deg.C pre-cooled physiological saline to remove surface floating blood, wiping with filter paper, weighing, and calculating liver index. Selecting 3 mice from each group, taking the liver at the same position, cutting tissue blocks, and fixing in 10% formalin for 24h for pathological section examination; storing the rest liver in a refrigerator at-80 deg.C, taking out when detecting, weighing 0.2g of the liver, placing in a glass homogenizer, shearing, adding 2mL of pre-cooled normal saline, making into 10% tissue homogenate in ice water bath, centrifuging at 3000rpm for 10min, and storing the supernatant at 4 deg.C for use.
3 index detection
3.1 liver index
The livers were dissected and weighed, and the liver index was calculated as [ weight of liver g/weight g ] x 100%.
3.2 serum Biochemical index determination
The ALT and AST in the serum are measured by an improved Reishi method according to the specific steps of the kit instruction.
3.3 Biochemical index determination of liver tissue
Taking 100 mu L of liver tissue homogenate, and measuring the contents of MDA, SOD and GSH in the liver tissue according to the operation of a kit instruction.
3.4 histopathological Observation
Liver tissue is fixed in 10% formalin fixing solution for 24 hr, washed with water, gradient-eluted with ethanol, xylene-transparent, paraffin-embedded, cut into 4 μm thick slices, and observed by HE staining.
3.5 hepatocyte mitochondria-related indices
3.5.1 hepatocyte mitochondrial isolation
Taking out mouse liver stored in refrigerator at-80 deg.C, cutting liver tissue of each group, washing residual blood with pre-cooled physiological saline, trimming connective tissue, sucking water with filter paper, and weighing (about 0.1 g); transferring the liver tissue to a pre-cooled glass homogenizer tube orifice, shearing the liver tissue into a non-obvious tissue block by using pre-cooled scissors, adding 1mL of pre-cooled mitochondrion separating medium (0.21M mannitol, 0.07M sucrose, 10mM Tris base, 1mM EDTA, 0.5mM EGTA, pH to 7.4), and homogenizing for 10 times in ice-water bath; transferring the tissue homogenate liquid into 1.5mL centrifuge tubes respectively, centrifuging at 4 ℃ and 1000 Xg for 10min, discarding the precipitate, transferring the supernatant liquid into another centrifuge tube, centrifuging at 4 ℃ and 10000 Xg for 10min, and obtaining the precipitate, namely the hepatocyte mitochondria.
3.5.2 hepatocyte mitochondrial Membrane potential assay
Extracting liver cell mitochondria, adding mitochondrial membrane potential measuring medium (0.25M sucrose, 5mM MgCl2, 10mM KCl, 5mM KH2P04, 10mM Hepes, 10mM succinate, pH 7.4), mixing to obtain suspension, and measuring mitochondrial protein concentration by using BCA protein concentration measuring kit; and adding 2.9mL of measuring medium into 100 mu L of mitochondrion suspension, adding 5 mu L of rhodamine 123, uniformly mixing, keeping the temperature at 37 ℃ for 30min, and measuring the fluorescence intensity at the excitation light wavelength of 484nm and the emission wavelength of 534 nm.
3.5.3 determination of liver cell mitochondria MDA content and ATPase activity
Extracting liver cell mitochondria, adding normal saline, mixing uniformly to form suspension, and measuring the protein concentration of the mitochondria by using a BCA protein concentration measuring kit; respectively taking 100 μ L of the granulesMeasuring MDA and Na in liver cell mitochondria according to the operation of kit instructions+-K+-ATPase and Ca2+-Mg2+-the activity of an ATPase.
4. Statistical treatment of each group of data with mean ± standard deviation
Representing data processed using SPSS 11.0 statistical software analysis, comparison between groups using one-way analysis of variance, P<0.05 was considered statistically different.
5 results of the experiment
5.1 test Compound Pair CCl4Effect of liver index in injured mice
Compared with the normal group, the liver weight and liver index of the model group mice are obviously increased, which indicates that the liver is damaged; compared with the model group, the liver weight and liver index of the silibinin group (positive control) mice are obviously reduced, which indicates that the silibinin can effectively relieve CCl4The resulting liver damage; like silybin, the liver index of each dose group of peucedanum praeruptorin was significantly reduced (compared with the model group), indicating that peucedanum praeruptorin has anti-drug liver injury activity (table 1).
TABLE 1 test monomer Compound vs CCl4Effect of liver index in injured mice: (
n＝10)
In comparison with the set of models,#P<0.05，##P<0.01，###P<0.001。
5.2 test monomer Compound Pair CCl4Influence of injured mouse serum ALT and AST
Compared with the normal group, the ALT and AST in the serum of the mouse in the model group are obviously increased, and the model building is successful; compared with the model group, ALT and AST in the serum of the mice in the silibinin group are obviously reduced, which shows that silibinin can effectively relieveCCl4The resulting liver damage; compared with the model group, the serum ALT and AST of the mice of the dose groups of 16mg/kg and 32mg/kg of peucedanum praeruptorum dunn are obviously reduced, and the serum AST content of the mice of the dose group of 8mg/kg is obviously reduced, which indicates that the peucedanum praeruptorum dunn has the activity of resisting drug-induced liver injury (Table 2).
TABLE 2 test monomer Compound vs CCl4Influence of serum ALT and AST in injured mice: (
n＝10)
In comparison with the set of models,#P<0.05。
5.3 test monomer Compound Pair CCl4Effect of damaging MDA, SOD and GSH in mouse liver
Compared with the normal group, the MDA content in the liver of the mouse in the model group is obviously increased, the contents of SOD and GSH are obviously reduced, and the model building is successful; compared with the model group, the content of MDA in the liver of the mouse with the silibinin group is obviously reduced, and the content of SOD and GSH is obviously increased, which shows that the silibinin can effectively relieve CCl4The resulting liver damage; compared with the model group, the peucedanum praeruptorum dunn dosage groups of 8mg/kg, 16mg/kg and 32mg/kg can obviously reduce the MDA content and increase the GSH content, and the 8mg/kg dosage group can also obviously increase the SOD content, which indicates that the peucedanum praeruptorum dunn has the activity of resisting drug-induced liver injury (Table 3).
TABLE 3 test monomer Compound vs CCl4Influence of damaged mouse liver MDA, SOD and GSH content: (n＝10)
In comparison with the set of models,#P<0.05，##P<0.01。
5.4 test monomer Compound Pair CCl4Effect of injuring mouse liver mitochondria MDA, ATPase and membrane potential
Compared with the normal group, the MDA content in liver mitochondria of the model group mice is obviously increased, and Na+-K+-ATPase and Ca2 +-Mg2+The activity of ATP enzyme is obviously reduced, the fluorescence intensity of mitochondria of liver cells is obviously increased, and mitochondrial membrane potential collapse is caused, which indicates that the modeling is successful; compared with the model group, the content of MDA in the liver of the mouse with the silibinin group is obviously reduced, and Na is+-K+-ATPase and Ca2+-Mg2+The activity of ATP enzyme is obviously improved, the fluorescence intensity of mitochondria is obviously reduced, thereby alleviating the degree of membrane potential collapse, and showing that silibinin can effectively alleviate CCl4Resulting in liver damage. Compared with a model group, each dose group of peucedanum praeruptorum dunn can obviously reduce the content of MDA; meanwhile, the Na content of the groups with the dosages of 16mg/kg and 32mg/kg can be obviously increased+-K+-ATPase and Ca2+-Mg2+ATPase activity, and can significantly reduce fluorescence intensity and inhibit mitochondrial membrane potential reduction, and the result shows that the praeruptorin can regulate mitochondrial function and resist drug-induced liver injury (Table 4).
TABLE 4 test monomer Compound vs CCl4Effects of Damage to mouse liver mitochondria MDA, ATPase and Membrane potential (
n＝10)
In comparison with the set of models,#P<0.05，##P<0.01。
Claims (1)
1. the application of praeruptorin in preparing the drug for protecting liver injury has the following structural formula:
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