CN115212196B - Application of aeginetia mulosa polyene compound - Google Patents

Application of aeginetia mulosa polyene compound Download PDF

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CN115212196B
CN115212196B CN202210987194.3A CN202210987194A CN115212196B CN 115212196 B CN115212196 B CN 115212196B CN 202210987194 A CN202210987194 A CN 202210987194A CN 115212196 B CN115212196 B CN 115212196B
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liver
polyene
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CN115212196A (en
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阮丽君
宋志军
姚彩云
缪剑华
吴云秋
杨晓男
闫炳雄
刘喜慧
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Guangxi Botanical Garden of Medicinal Plants
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Abstract

The invention discloses a new application of an aeginetia polyene compound, which refers to the application of the aeginetia polyene compound as an active ingredient in preparing a medicine or health-care food for preventing or treating liver diseases. The experimental results show that: the aeginetia sinensis polyene E and the figwort red acid can improve the survival rate of HepG2 cells induced by APAP, and show a certain protective activity on liver cells; both Aeginetia sinensis polyene E and radix scrophulariae red acid can effectively reduce CCl 4 The ALT value, AST value, MDA value and ROS value of liver disease rats are caused, the SOD activity of liver tissues of rats can be obviously improved, and the liver disease rats have certain prevention and treatment effects on the occurrence and development of liver injury. Therefore, the application of the aeginetia-polyene compound serving as an active ingredient in preparing a medicament or health-care product for preventing and treating liver diseases has important significance in research and application of the aeginetia-polyene compound.

Description

Application of aeginetia mulosa polyene compound
Technical Field
The invention belongs to an application of an aeginetia polyene compound, and particularly relates to a preparation method of the aeginetia polyene compound in preparation of a medicament capable of improving survival rate of HepG2 cells induced by APAP and a medicament capable of reducing oxidative stress level of liver tissues of rats with liver diseases caused by CCl 4.
Background
The liver is a central organ for metabolism and nutrition of human body, not only completes synthesis and decomposition of carbohydrate, protein and fat, but also most endogenous and exogenous metabolic end products need to be transformed by the liver. Liver diseases are one of the common diseases in modern life, when liver functions are problematic, the digestive functions are directly affected, and the digestive functions are reduced, so that appetite is lost, absorption is easily affected, if the digestive functions are absorbed for a long time, the human body cannot be provided with enough energy, further, the human body is easy to fatigue, mental and dizziness and tinnitus are not concentrated, and even the human body is distracted.
Liver diseases, i.e., liver injury, mainly include viral hepatitis, alcoholic hepatitis and drug-induced hepatitis, which are clinically manifested as liver necrosis, fatty liver, cholestasis, liver fibrosis, cirrhosis, liver cancer, etc., and currently, the treatment of liver injury is still a global serious problem. Carbon tetrachloride is a liver fibrosis inducer and is often used in experiments of acute liver injury, namely, a mouse liver injury model is obtained by injecting carbon tetrachloride, and the liver injury is judged by detecting the content of glutamic pyruvic transaminase (ALT/GPT), glutamic oxaloacetic transaminase (AST/GOT) and superoxide dismutase (SOD) and propylene glycol (MDA) in the serum of the mouse.
Aeginetia polyene compounds, including Aeginetia polyene E (Aeginetin), radix scrophulariae red acid (Azafrin), are extracted from Orobanchaceae (Orobanchaceae), aeginetia (Aeginetia), and carotenoid, and are commonly used for treating sore throat, cough, infantile hyperpyrexia, urinary tract infection, osteomyelitis, and venomous snake bite.
However, up to now, no research report on the use of Aeginetia polyene compounds in preventing or treating liver diseases is seen.
Disclosure of Invention
The object of the present invention is to solve at least the above drawbacks and to provide advantages to be described later.
To achieve these objects and other advantages and in accordance with the purpose of the invention, there is now provided the use of the aeginetia-polyene compound as a sole active ingredient for the preparation of a medicament for improving the survival rate of APAP-induced HepG2 cells and a medicament for reducing the oxidative stress level of CCl4 induced liver tissue of liver disease rats.
In the scheme, the aeginetia polyene compound is specifically used as an active ingredient for preparing a medicament for preventing or treating liver diseases, and can be prepared into an oral medicament or a non-oral medicament; wherein, the oral administration can be made into any conventional dosage forms such as tablet, capsule, powder, granule, etc.; the medicine can be made into injection for non-oral administration. Therefore, the method is suitable for various application scenes and has good market prospect.
Preferably, the aeginetia polyene compound has the following chemical structural formula, namely chemical formula I:
the method comprises the steps of carrying out a first treatment on the surface of the Wherein n is greater than or equal to 1.
Preferably, the compound is aeginetone, and has the following chemical structural formula, namely chemical formula II:
。
preferably, the compound is figwort red acid, and has the following chemical structural formula, namely chemical formula III:
。
the preparation method of the aeginetia polyene compound is characterized by comprising the following steps of:
step one, obtaining and crushing the wild rice to obtain wild rice powder.
And step two, repeatedly leaching the wild rice powder for 3 times by using an ethanol solution with the volume fraction of 70% -80%, and combining the liquid obtained by leaching for 3 times into leaching liquid.
And thirdly, filtering and concentrating the obtained leaching solution under reduced pressure to obtain crude extract.
And step four, dissolving the crude extract with water to obtain crude extract, and sequentially extracting with petroleum ether and ethyl acetate to obtain the wild rice ethyl acetate extract.
And fifthly, dissolving the aeginetia volvata ethyl acetate extract by adopting methanol, filtering, separating by an MCI column, concentrating 60% methanol eluent, and separating out yellow solid to obtain the aeginetia volvata polyene E.
Wherein, the feed liquid ratio of the aeginetia powder to the ethanol solution is 1: 10-30 parts; the volume ratio of the ethyl acetate to the crude extract is 0.5-2: 1.
the preparation method of the aeginetia polyene compound is characterized by comprising the following steps of:
step one, obtaining and crushing the wild rice to obtain wild rice powder.
And step two, repeatedly leaching the wild rice powder for 3 times by using an ethanol solution with the volume fraction of 70% -80%, and combining the liquid obtained by leaching for 3 times into leaching liquid.
And thirdly, filtering and concentrating the obtained leaching solution under reduced pressure to obtain crude extract.
And step four, dissolving the crude extract with water to obtain crude extract, and sequentially extracting with petroleum ether and ethyl acetate to obtain the wild rice ethyl acetate extract.
And fifthly, dissolving the aeginetia indica ethyl acetate extract by adopting methanol, filtering, separating by an MCI column, concentrating an 85% methanol eluent, and separating out red solid to obtain the aeginetia indica polyene compound figwort red acid.
Preferably, the MCI column is an 8×20 cm small pore resin column; MCI column separations specifically included: methanol-water ratio is adopted for column passing; the gradient elution was set to 100 for pure water to methanol ratio: 0. 80: 20. 60: 40. 40: 60. 15: 85. 0:100, eluting 1L per scale.
Preferably, the medicament is a pharmaceutical preparation prepared by taking the aeginetia volvata compound as the only active ingredient and adding a pharmaceutically acceptable carrier.
The invention has the advantages that:
firstly, the invention can promote the aeginetia polyene compound to fully exert the medicinal value, and has important significance for research and application of the aeginetia polyene compound.
Secondly, the aeginetia E and the figwort red acid are extracted from the aeginetia plants to prepare the medicine for preventing and treating liver diseases, so that the pain and trouble caused by surgical excision, chemotherapy, radiotherapy and the like can be reduced.
In addition, when the aeginetia polyene compound disclosed by the invention is used as an active ingredient for preparing a medicine or health-care food for preventing or treating liver diseases, the aeginetia polyene compound can be prepared into oral medicines or non-oral medicines; wherein, the oral administration can be made into any conventional dosage forms such as tablet, capsule, powder, granule, etc.; the medicine can be made into injection for non-oral administration. Therefore, the method is suitable for various application scenes and has good market prospect.
Detailed Description
The present invention is described in further detail below with reference to examples to enable those skilled in the art to practice the invention by reference to the specification.
It will be understood that terms, such as "having," "including," and "comprising," as used herein, do not preclude the presence or addition of one or more other elements or groups thereof.
The experimental methods described in the following embodiments are conventional methods unless otherwise indicated, and the reagents and materials are commercially available.
Example 1
1 extraction and separation of Aeginetia polyene compounds
Step one, taking the dry whole plant 20 kg of the aeginetia indica and crushing to obtain aeginetia indica powder.
Dispersing the wild rice powder in an ethanol solution with the volume fraction of 70-80%, soaking for 5 days at normal temperature, extracting for 3 times, and combining the liquid obtained by 3 times of leaching into leaching liquor; wherein, the feed liquid ratio of the aeginetia powder to the ethanol solution is 1: 10-30.
And thirdly, filtering and concentrating the leaching solution obtained in the second step under reduced pressure to obtain crude extract.
Dissolving the crude extract with water to obtain a crude extract, extracting with petroleum ether to remove fat-soluble impurities, and then extracting the crude extract with ethyl acetate to obtain an wild rice ethyl acetate extract; wherein the volume ratio of the ethyl acetate to the crude extract is 0.5-2: 1.
dissolving the aeginetia indica ethyl acetate extract by using methanol, filtering, separating by using an 8 multiplied by 20 cm small-hole resin column (MCI filler), concentrating 60% methanol eluent, and separating out yellow solid which is aeginetia indica polyeneE, wherein the total weight of the aeginetia indica polyeneE is 6.8 g; concentrating 85% methanol eluent to obtain red solid which is 0.6 g of the figwort red acid; wherein the weight ratio of the ethyl acetate extract to the MCI filler is 1: 40-50 parts; the elution process adopts water-methanol gradient elution, and the gradient elution is set to be that the ratio of pure water to methanol is 100 respectively: 0. 80: 20. 60: 40. 40: 60. 15: 85. 0:100, eluting 1L per scale.
2 structural identification of Aeginetia polyene compounds
2.1 Structure of Aeginetia polyene compound:
2.2 Nuclear magnetic resonance data of the Compound Aeginetiene E (Varian-600 MHz NMR):
1 H NMR (600 MHz，d-CD 3 OD):δ H 7.33 (d，J = 11.8 Hz， 1H)， 7.05 – 6.94 (m， 1H)， 6.81 (dd，J = 15.0， 11.5 Hz， 1H)， 6.67 – 6.57 (m， 1H)， 6.43 (d，J = 9.8 Hz， 1H)， 6.40 (d，J = 8.9 Hz， 1H)， 6.32 (d，J = 12.6 Hz， 1H)， 6.30 (d，J = 16.2 Hz， 1H)， 6.21 (d，J = 11.3 Hz， 1H)， 2.03 (s，3H)， 2.00 (s，3H)， 1.95 (s，3H)， 1.91 – 1.86 (m， 1H)， 1.85 – 1.78 (m， 1H)， 1.71 (td，J = 13.1， 3.2 Hz， 1H)， 1.47 (d，J = 12.4 Hz， 1H)， 1.40 – 1.33 (m， 1H)， 1.21 (s，3H)， 1.17 (d，J = 13.5 Hz， 1H)， 1.09 (s，3H)， 0.81 (s，3H).
13 C-NMR(151 MHz，d-CD 3 OD):δ C 171.96， 141.20， 140.38， 137.92， 137.73， 137.27， 135.52， 132.52， 132.35， 131.80， 129.17， 127.91， 127.35， 80.71， 76.02， 39.68， 37.47， 36.76， 27.55， 27.37， 25.75， 19.09， 13.26， 12.95， 12.83。
2.3 Nuclear magnetic resonance data of the compound figwort red acid:
1 H NMR (600 MHz，d-CD 3 OD):δ H 7.38 (d，J = 15.5 Hz， 1H)， 6.96 – 6.87 (m， 1H)， 6.78 (dd，J = 15.0， 11.5 Hz， 1H)， 6.75 – 6.66 (m， 1H)， 6.60 (d，J = 11.7 Hz， 1H)， 6.42 (dd，J = 15.5， 10.5 Hz， 2H)， 6.32 (d，J = 11.9 Hz， 2H)， 6.29 (d，J = 16.0 Hz， 1H)， 6.21 (d，J = 11.4 Hz， 1H)， 5.87 (d，J = 15.5 Hz， 1H)， 2.02 (s， 3H)， 2.00 (s， 3H)， 1.95 (s， 3H)， 1.92 – 1.88 (m， 1H)， 1.83 (d，J = 3.7 Hz， 1H)， 1.71 (td，J = 13.1， 3.3 Hz， 1H)， 1.47 (d，J = 13.1 Hz， 2H)， 1.40 – 1.35 (m， 2H)， 1.29 (s， 2H)， 1.21 (s， 3H)， 1.17 (d，J = 13.1 Hz， 1H)， 1.09 (s， 3H)， 0.81 (s， 3H).
13 C-NMR(151 MHz，d-CD 3 OD):δ C 170.97， 159.59， 150.61， 140.84， 140.18， 138.10， 137.44， 135.56， 135.40， 134.48， 132.93， 132.34， 131.93， 129.98， 127.47， 117.19， 80.71， 76.02， 39.68， 37.46， 36.76， 27.56， 27.38， 25.75， 19.09， 13.26， 12.92， 12.56。
3. activity test of Aeginetia mulosa
3.1 protective Activity of Aeginetia polyene Compounds on APAP-induced HepG2 cells
(1) Test method
Step a, taking a human liver cancer cell strain HepG2 in logarithmic growth phase, preparing a single cell suspension from the HepG2 cell culture solution by using an RPMI-1640 culture solution containing 10% fetal bovine serum, inoculating into a 96-well plate according to the amount of 2000 cells per well, placing 100 mu l per well volume into 5% CO 2 The cells were incubated at 37℃for 24 hours.
Step b, the medicinal components are an aeginetiene E group and a radix scrophulariae red acid group, and the cells are treated by aeginetiene E or radix scrophulariae red acid and acetaminophen (APAP, 8 mM) respectively; the positive control group treated cells with APAP and Bicyclol (Bicyclol) together; model groups were treated with acetaminophen; the blank group is not processed. The above groups were treated and incubated for 24 hours.
And c, after the incubation is finished, adding 5 mg/ml MTT solution into each hole, continuously culturing for 4 hours, absorbing and discarding the culture solution, adding DMSO, shaking uniformly, incubating for 3 hours, and finally measuring an OD value at 517 nm on an ELISA monitor, and calculating the cell survival rate (%).
(2) Calculation of cell viability
Cell viability% = experimental OD value/blank OD x 100%. The results are shown in Table 2.
Table 1: aeginetide and figwort red acid have protective activity on HepG2 hepatocytes (n=5, ** P＜0.01）
project Cell viability%
Blank group 100.0±4.25
Model group 48.13±3.25
Positive control group 64.32±1.25 **
Aeginetia volvata E group 57.85±2.31 **
Radix scrophulariae red acid group 54.23±0.92 **
(3) Analysis of results
Compared with the model group, the aeginetia volvata E and the figwort red acid can improve the survival rate of HepG2 cells induced by APAP, and show a certain protective activity on liver cells.
3.2 Balanophora japonica thunb polyene pair CCl 4 Protective effect on liver injury of rats
(1) Inspection method
Preparing a solution: the aeginetia volvata E and the figwort red acid are weighed for a certain amount, and dissolved by 0.5 percent CMC-Na to prepare the concentration of 100 mg/mL.
Animal administration: 40 male rats were randomly divided into a blank group, a model group, an Aeginetia sinensis E, and a radix scrophulariae red acid group, each group of 10 rats. The aeginea E and the figwort red acid groups are administrated according to 100 mg/Kg by gastric lavage, and the normal control group and the model group are respectively administrated with 0.5% CMC-Na solution with the same quantity, and the gastric lavage is carried out for 1 time a day and for 7d continuously. After the last dose of 2 h, all groups of mice except the blank group were intraperitoneally injected with 0.2% carbon tetrachloride (CCl 4 ) Is 20 mL/Kg of olive oil solution. After 16 h, the mice were weighed, euthanized, and blood samples and liver tissue were collected for further testing.
And (3) detection: serum is detected by a kit, and serum glutamic pyruvic transaminase (ALT) and glutamic oxaloacetic transaminase (AST) are measured according to the specification. Liver tissue was weighed 200. 200 mg, homogenized in 1.8. 1.8 mL pre-chilled normal saline, centrifuged at 1500 Xg for 5 min, and the homogenate was collected. The homogenate was first assayed for protein concentration according to the Bio-Rad protein assay kit method. Then, the homogenate is taken and the SOD activity, MDA content and ROS production level of the homogenate are detected according to the specification steps of the detection kit. Finally, the content of the factors in the homogenate is normalized according to the protein concentration.
(2) Test results
The test results are expressed as mean.+ -. Standard deviation (mean.+ -. SD), and the mean values between the sets of data are compared in pairs using a one-way anova followed by the SNK-q test. At P <0.05, the difference is considered statistically significant. The results are shown in Table 2.
Table 2: influence of Aeginetia sinensis E and radix scrophulariae Red on serum index of rat (n=8)
Project ALT(IU/L) AST(IU/L) MDA(nmol/mgprot) SOD(U/ml) ROS(%)
Blank group 45.34±9.83 256.54±3.27 3.78±0.04 835.54±84.81 105.21±29.11
Model group 263.16±50.26 500.26±85.12 8.95±1.03 629.68±63.03 260.88±35.21
Aeginetia indica polyene E 68.66±21.03 290.12±22.31 4.26±0.11 812.16±84.00 155.47±10.12
Radix scrophulariae red acid 82.10±36.12 322.52±36.03 4.77±0.41 851.60±94.84 126.81±20.13
(3) Analysis of results
The ALT and AST activities in the rat serum of the model group were significantly increased compared with the control group (P<0.01). ALT and AST activities were reduced in rat serum from Aeginetia polyene E group and radix scrophulariae red group compared to model group (P<0.01 No obvious difference exists between the aeginetia volvata E group and the radix scrophulariae red acid group. These results demonstrate that both Aeginetia polyene E and figwort red acid can alleviate CCl 4 Resulting in liver injury in liver disease rats.
The antioxidant enzyme SOD activity in rat liver tissue of model group is obviously reduced (P)<0.01 A) is provided; compared with the model group, the SOD activities in the liver tissues of rats of the Aeginetia polyene E group and the radix scrophulariae red acid group are obviously increased (P)<0.01 And the radix scrophulariae red acid group is more remarkable than the Aeginetia zizaniae E group. The MDA content in rat liver tissue was significantly increased in model group compared to the blank group (P<0.01 Reflecting the increased degree of lipid peroxidation in rats; compared with the model group, the MDA content in rat liver tissue of the Aeginetia polyene E group and the radix scrophulariae red acid group is obviously reduced (P<0.01). Detection of ROS levels in rat liver showed increased ROS production levels in rat liver tissue of the model group compared to the blank group (P<0.01 A) is provided; compared with the model group, the level of ROS production in rat liver tissues of the Aeginetia polyene E group and the radix scrophulariae red acid group is obviously reduced (P)<0.01 High dose group)Has obvious effect (P)<0.01). The results show that the aeginetia stock E and the radix scrophulariae red acid can reduce CCl 4 Resulting in oxidative stress levels in liver tissue of liver disease rats.
Although embodiments of the invention have been disclosed above, they are not limited to the use listed in the specification and embodiments. It can be applied to various fields suitable for the present invention. Additional modifications will readily occur to those skilled in the art. Therefore, the invention is not to be limited to the specific details disclosed herein without departing from the general concepts defined in the claims and the equivalents thereof.

Claims (2)

1. The application of the aeginea polyene compound is characterized in that the radix scrophulariae red acid is used as the only active ingredient for preparing medicines capable of improving the survival rate of HepG2 cells induced by APAP and medicines capable of reducing the oxidative stress level of liver tissues of rats with liver diseases caused by CCl 4;
the figwort red acid has the following chemical structural formula, which is called as chemical formula III for short:
。
2. the use of the aeginetia polyene compound as claimed in claim 1, wherein the medicament is a pharmaceutical preparation prepared by taking figwort red acid as the only active ingredient and adding a pharmaceutically acceptable carrier.
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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH07258158A (en) * 1994-03-14 1995-10-09 Marigen Sa Biotenside solvent for medicine and cosmetic
CN102772397A (en) * 2012-08-06 2012-11-14 上海中医药大学 New application of azafrin
CN103254163A (en) * 2013-05-17 2013-08-21 南京泽朗医药科技有限公司 Preparation method of aeginetolide

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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