CN112645808A - 5-hydroxy-1, 7-diphenyl-3-heptanone separated from galangal and application thereof - Google Patents
5-hydroxy-1, 7-diphenyl-3-heptanone separated from galangal and application thereof Download PDFInfo
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Abstract
The invention discloses 5-hydroxy-1, 7-diphenyl-3-heptanone separated from galangal and application thereof, wherein the 5-hydroxy-1, 7-diphenyl-3-heptanone provided by the invention has obvious improvement on sugar tolerance after being dried, and the 5-hydroxy-1, 7-diphenyl-3-heptanone has obvious effect of improving IR. The compounds can upregulate the transcriptional level of Nrf2mRNA and downstream target genes.
Description
Technical Field
The invention relates to the technical field of natural medicines, and particularly relates to 5-hydroxy-1, 7-diphenyl-3-heptanone separated from galangal and application thereof.
Background
Rhizoma Alpiniae Officinarum is dried rhizome of Alpinia Officinarum (Alpinia officinarum Hance) of Alpinia of Zingiberaceae, has effects of warming spleen and stomach for dispelling cold, warming and dredging channels for relieving pain, regulating stomach function, calming adverse qi, activating qi-flowing, and removing food stagnation, and can be used for treating abdominal psychroalgia, stomach cold emesis, etc. Chemical research shows that the galangal mainly contains flavonoids, volatile oil and diphenyl heptane compounds. Pharmacological research shows that the compound has various pharmacological effects of resisting diabetes, ulcer, vomit, inflammation and the like. Galangal extracts are reported to have significant hypoglycemic effects. In China, researches report that galangal extract and dibenzoheptane compounds have remarkable effect of improving insulin resistance. However, the current reports lack deeper research and cannot well determine the specific influence of the separated and extracted 5-hydroxy-1, 7-diphenyl-3-heptanone from galangal on diabetes.
Disclosure of Invention
The invention aims to provide 5-hydroxy-1, 7-diphenyl-3-heptanone separated from galangal and application thereof, wherein the 5-hydroxy-1, 7-diphenyl-3-heptanone is separated from galangal extracts through chemical component research, and the 5-hydroxy-1, 7-diphenyl-3-heptanone has activity of promoting differentiation of preadipocytes to different degrees, so as to solve the problems in the background technology.
In order to achieve the purpose, the invention provides the following technical scheme:
a method for separating 5-hydroxy-1, 7-diphenyl-3-heptanone from rhizoma Alpiniae Officinarum comprises the following steps:
step 1: extracting rhizoma Alpiniae Officinarum extract by pulverizing 42kg of rhizoma Alpiniae Officinarum, refluxing with 80% ethanol under heating for 3 times (2 hr each time) at a ratio of 1:10, mixing filtrates, and concentrating to 10L;
step 2: separation and purification: adding a small amount of galangal extract into a liquid separation bottle, adding a large amount of ethyl acetate, sufficiently shaking, standing for more than 1 hour, and obviously layering, respectively taking an upper layer liquid and a lower layer liquid, spotting the plates, and inspecting at 254nm, wherein if the lower layer liquid has no spots on the plates and the upper layer liquid has spots, the extraction is finished;
and step 3: after extraction, combining supernatant liquid, carrying out rotary evaporation and evaporation to obtain galangal extract, wherein 55g of the obtained extract is loaded on a column according to a ratio of 1:7, the loading amount of silica gel is 385g, the silica gel protection column is 55g, and the above eluent is respectively mixed with petroleum ether: ethyl acetate: (30:1), (25:1), (20:1), (15:1), (10:1), (5:1) and (5:3) by eluting DH6 (5-hydroxy-1, 7-diphenyl-3-heptanone) at 10: 1.
Further, slag of the lower layer liquid is added to the lower layer liquid in the step 2 as much as possible.
Further, the lower layer liquid point plate in the step 2 is developing solvent petroleum ether, ethyl acetate 5: 2.
Further, the supernatant of step 3 was an ethyl acetate layer.
Further, the pharmaceutical composition comprises 5-hydroxy-1, 7-diphenyl-3-heptanone or a pharmaceutically acceptable derivative and a pharmaceutically acceptable carrier.
Furthermore, the 5-hydroxy-1, 7-diphenyl-3-heptanone or the pharmaceutically acceptable derivatives thereof are used for preparing the medicines for treating diseases caused by insulin resistance.
Further, the diseases caused by insulin resistance include diabetes, hyperuricemia, hyperlipidemia, metabolic syndrome, obesity, and cardiovascular diseases.
The invention provides another technical scheme that: application of 5-hydroxy-1, 7-diphenyl-3-heptanone separated from rhizoma Alpiniae Officinarum in preparing antioxidant food, health product or medicine is provided.
Compared with the prior art, the invention has the beneficial effects that: after the extract is subjected to dry prediction, the random blood sugar level of a mouse is remarkably reduced, the sugar tolerance is remarkably improved, and the IR improving effect of the galangal extract is remarkable. The effect of 5-hydroxy-1, 7-diphenyl-3-heptanone, one of the obtained components, on the Nrf2/ARE pathway of liver cells under the action of high sugar. The compounds can upregulate the transcriptional level of Nrf2mRNA and downstream target genes.
Drawings
FIG. 1 is an overall block diagram of a path generation system of the present invention;
FIG. 2 is a schematic diagram showing the effect of the active ingredient of Alpinia galanga DH6 of the present invention on HepG2 cell proliferation;
FIG. 3 is a schematic diagram showing the sugar consumption of DH6 in 15min on HepG2 cells according to the present invention for high sugar-dry prognosis;
FIG. 4 is a schematic illustration of the effect of different high carbohydrate stem prognostic drugs of the present invention on carbohydrate uptake in HepG2 cells;
FIG. 5 is a schematic representation of the effect of DH6 of the present invention on ROS in IR-HepG2 cells;
FIG. 6 is a schematic diagram showing the effect of DH6 on SOD in IR-HepG2 cells;
FIG. 7 is a schematic diagram showing the effect of DH6 on the protein expression level of Nrf 2;
FIG. 8 is a diagram showing the effect of DH6 on the expression level of HO-1 protein.
Detailed Description
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 only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
A method for separating 5-hydroxy-1, 7-diphenyl-3-heptanone from rhizoma Alpiniae Officinarum comprises the following steps:
extracting rhizoma Alpiniae Officinarum extract by pulverizing 42kg of rhizoma Alpiniae Officinarum, refluxing with 80% ethanol under heating for 3 times (2 hr each time) at a ratio of 1:10, mixing filtrates, and concentrating to 10L; separation and purification: adding a small amount of rhizoma Alpiniae Officinarum extract into a liquid separating bottle, adding a large amount of ethyl acetate, shaking thoroughly, standing for more than 1 hr to separate layers, collecting supernatant and subnatant (adding residue of subnatant as much as possible), spotting plates (developing agent petroleum ether: ethyl acetate: 5:2), and detecting at 254nm to finish extraction if the subnatant has no spot on the plate and the supernatant has spot. After extraction, the upper layer liquid (ethyl acetate layer) is taken and combined, steamed and evaporated to dryness to obtain the galangal extract. 55g of the obtained extract is loaded on a column according to the ratio of 1:7, the sample loading amount of silica gel is 385g, and the column is protected by the silica gel. Respectively eluting with petroleum ether: ethyl acetate: (30:1), (25:1), (20:1), (15:1), (10:1), (5:1) and (5:3) and DH6 (5-hydroxy-1, 7-diphenyl-3-heptanone) is obtained by eluting at 10:1, and the structural formula is shown in figure 1.
Pharmacodynamic experiments prove that:
effect of DH6 on HepG2 cell proliferation
As shown in FIG. 2, the survival rate of HepG2 cells was not significantly affected at DH6 concentrations of 0-100. mu. mol/L compared to the normal control group. Compare # to blank set: p <0.05, # #: p <0.01, ####:: p <0.001, n ═ 4.
Effect of DH6 on sugar consumption by IR-HepG2 cells
As shown in fig. 3, the consumption of glucose by cells was significantly reduced (p <0.01) compared to the normal control group by the IR model group induced by high glucose, indicating that the IR model induction was successful and that the cells in the model group were resistant to insulin. After the treatment of adding the positive drug, namely the rosiglitazone, compared with a normal control group, the glucose consumption has obvious difference; the glucose consumption was significantly increased for the rosiglitazone group (p <0.05) compared to the model group, indicating that the positive drug group had improved sugar consumption by IR-HepG2 cells.
Compared with a normal control group, the DH6 active ingredient can improve the sugar consumption of IR-HepG2 cells, and when the concentration of DH8 is 10uM, 20uM and 50uM, the sugar consumption is not significantly different from that of a blank group, and is significantly different from that of a model group (p < 0.05). Indicating that DH6 can effectively improve the consumption of glucose by IR-HepG2 cells.
In fig. 3, drug groups compared to model groups: p <0.05, p <0.01, p: p <0.001, n ═ 4. Model set #: p <0.05, # #: p <0.01, ####:: p <0.001, n ═ 4.
Effect of DH6 on sugar consumption by IR-HepG2 cells
In the experiment, 2-NBDG fluorescent detection tracer is adopted to observe the glucose uptake condition of cells after DH6 drug treatment. As shown in FIG. 4, the glucose uptake of the cells was significantly reduced (P <0.001) by the group of insulin resistance models induced by high glucose compared to the normal control group, indicating that the IR model was successfully induced and the cells of the group produced IR. After the positive drug-rosiglitazone is added for treatment, the glucose intake is not obviously different from that of a normal control group; compared with the model group, the glucose uptake of the cells of the rosiglitazone group (p <0.05) is remarkably increased, indicating that the positive drug can effectively improve the glucose uptake of the IR-Hep G2 cells. Compared with the model group, the relative uptake fluorescence values of glucose at the concentrations of DH6 of 10. mu.M, 20. mu.M and 100. mu.M were significantly different from the model group (p < 0.001). Indicating that DH6 can effectively improve the glucose uptake of IR-HepG2 cells.
In fig. 4, drug groups compared to model groups: p <0.05, p <0.01, p: p <0.001, n ═ 4. Model set #: p <0.05, # #: p <0.01, ####:: p <0.001, n ═ 4.
4. Effect of drugs on intracellular ROS levels in insulin resistance model
In the experiment, a fluorescent probe DCFH-DA is used for staining, and then the cell is placed on a flow cytometer for detecting the intracellular ROS level. Through analysis, the results are shown in fig. 5, compared with a normal control group, the ROS level in the model group is increased with a great significance (P < 0.001); compared with the model group, the positive control group (with the most significant difference (P <0.001) between the model groups, and the DH6 concentration of 10uM, has no significant difference between the model groups, but with the DH6 concentration of 20uM and 50uM, has significant difference between the model groups (P <0.05), and the DH6 significantly reduces the ROS level in IR-Hep G2 cells and shows significant antioxidant activity.
In fig. 5, drug groups compared to model groups: p <0.05, p <0.01, p: p <0.001, n ═ 4. Model set #: p <0.05, # #: p <0.01, ####:: p <0.001, n ═ 4.
5. Effect of drugs on the Activity of antioxidant enzyme SOD in insulin resistance model cells
When oxidative stress occurs, the body can generate a series of antioxidant reactions to protect cells. SOD is one of important antioxidant enzymes for preventing free radical damage in organisms, can clear free radicals in cells to protect the cells, and can reflect the capability of the cells for clearing oxygen free radicals. The effect of DH6 on SOD activity in IR-HepG2 cells is shown in FIG. 6, and the results show that DH6 promotes the release of SOD. Compared with a normal control group, the SOD activity in the model group is reduced remarkably (P <0.001), the activity of the SOD in the rosiglitazone group is not significantly different from that in the normal control group, and compared with the model group, the SOD activity in the IR-HepG2 cell is increased remarkably when the concentration of DH6 reaches 20uM and 50uM (P < 0.05).
In fig. 6, drug groups compared to model groups: p <0.05, p <0.01, p: p <0.001, n ═ 4. Model set #: p <0.05, # #: p <0.01, ####:: p <0.001, n ═ 4.
Glucose consumption experimental study shows that DH6 can increase sugar consumption of IR-HepG2 cells, and has better improving effect on sugar metabolism of IR-HepG2 cells. DH8 can effectively reduce ROS in the model and improve the activity of antioxidant substances.
Experiment of DH6 activating Nrf2/ARE Signal pathway
(1) Nrf2 protein
The nuclear transcription factor Nrf2 has the effect of resisting oxidative stress, and after DH6 is administrated, the protein expression level of Nrf2 is obviously increased, which indicates that DH6 can play the role of resisting oxidative stress by activating Nrf2, thereby improving insulin resistance caused by high sugar, and the result is shown in figure 7. Single factor analysis of variance was used for comparisons between groups, and differences were considered statistically significant when P < 0.05. # p <0.05, # p <0.01, # p <0.001 compared to the blank group; compared to the model group, p <0.05, p <0.01, p < 0.001.
(2) HO-1 protein
Heme oxygenase-1 (HO-1) is a related protein downstream of Nrf2, the HO-1 pathway is a typical defense system of cells against oxidative stress, and after administration, the HO-1 protein expression is remarkably increased, which shows that DH6 can play a role in resisting oxidative stress by activating the downstream HO-1 protein of Nrf2, thereby improving insulin resistance caused by high sugar, and the result is shown in figure 8.
A HepG2 cell model (IR-HepG2 cell) of insulin resistance is established based on oxidative stress, and the model is utilized to research a specific mechanism and a signal path of action of improving the insulin resistance action of 5-hydroxy-1, 7-diphenyl-3-heptanone. The research on whether the active ingredient DHs of the galangal can improve the oxidative stress and the sugar metabolism in the IR-HepG2 cell through the Nrf2-AER signal or not is carried out, the network pharmacological mechanism of improving the insulin resistance of the active ingredient of the galangal through the Nrf2-AER signal channel is clarified, and the research helps develop the galangal ingredient medicine for improving the insulin resistance.
The experimental result shows that the galangal extract, particularly 5-hydroxy-1, 7-diphenyl-3-heptanone, has a remarkable treatment effect on the early stage of diabetes, particularly the 5-hydroxy-1, 7-diphenyl-3-heptanone has a remarkable effect of improving insulin resistance, and a new progress is made on the basis of the former people. The research finds that the improvement of Insulin Resistance (IR) of the galangal 5-hydroxy-1, 7-diphenyl-3-heptanone is closely related to the activation of Nrf2/ARE pathway.
The effect of the obtained component 5-hydroxy-1, 7-diphenyl-3-heptanone on the Nrf2/ARE pathway of liver cells under the action of high sugar was observed. The compounds can upregulate the transcriptional level of Nrf2mRNA and downstream target genes.
The above description is only for the preferred embodiment of the present invention, but the scope of the present invention is not limited thereto, and any person skilled in the art should be able to cover the technical solutions and the inventive concepts of the present invention within the technical scope of the present invention.
Claims (4)
1. A5-hydroxy-1, 7-diphenyl-3-heptanone isolated from Alpinia officinarum Hance is characterized by comprising 5-hydroxy-1, 7-diphenyl-3-heptanone or a pharmaceutically acceptable derivative and a pharmaceutically acceptable carrier.
2. The isolated 5-hydroxy-1, 7-diphenyl-3-heptanone from galangal as claimed in claim 1, wherein 5-hydroxy-1, 7-diphenyl-3-heptanone or a pharmaceutically acceptable derivative thereof is used for the preparation of a medicament for the treatment of diseases caused by insulin resistance.
3. The isolated 5-hydroxy-1, 7-diphenyl-3-heptanone of galangal as claimed in claim 2, wherein the disorders caused by insulin resistance comprise diabetes, hyperuricemia, hyperlipidemia, metabolic syndrome, obesity, cardiovascular disease.
4. Use of 5-hydroxy-1, 7-diphenyl-3-heptanone isolated from galangal as claimed in claim 1 for the preparation of an antioxidant food, health product or pharmaceutical.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114533711A (en) * | 2022-03-08 | 2022-05-27 | 海南医学院 | Application of diphenyl heptanone compound in preparation of lipid metabolism improving drugs and compound preparation method |
| CN114686424A (en) * | 2022-03-09 | 2022-07-01 | 海南医学院 | Method for regulating C/EBP alpha gene expression and C/EBP alpha expression inhibitor |
| CN115671086A (en) * | 2022-11-09 | 2023-02-03 | 海南医学院第二附属医院 | Application of 5-hydroxy-1,7-diphenyl-3-heptanone or medicinal derivative in preparation of drugs for treating hepatitis and liver cancer |
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| CN108066683A (en) * | 2018-01-25 | 2018-05-25 | 海南医学院 | Application of the galangal in the drug or health products for preparing the gastric ulcer that prevention and treatment non-steroidal anti-inflammatory drugs triggers |
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2021
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| CN108066683A (en) * | 2018-01-25 | 2018-05-25 | 海南医学院 | Application of the galangal in the drug or health products for preparing the gastric ulcer that prevention and treatment non-steroidal anti-inflammatory drugs triggers |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114533711A (en) * | 2022-03-08 | 2022-05-27 | 海南医学院 | Application of diphenyl heptanone compound in preparation of lipid metabolism improving drugs and compound preparation method |
| CN114533711B (en) * | 2022-03-08 | 2024-01-30 | 海南医学院 | Application of diphenyl heptanone compounds in preparation of drugs for improving lipid metabolism and preparation method of compounds |
| CN114686424A (en) * | 2022-03-09 | 2022-07-01 | 海南医学院 | Method for regulating C/EBP alpha gene expression and C/EBP alpha expression inhibitor |
| CN114686424B (en) * | 2022-03-09 | 2023-09-22 | 海南医学院 | Method for regulating and controlling C/EBP alpha gene expression and C/EBP alpha expression inhibitor |
| CN115671086A (en) * | 2022-11-09 | 2023-02-03 | 海南医学院第二附属医院 | Application of 5-hydroxy-1,7-diphenyl-3-heptanone or medicinal derivative in preparation of drugs for treating hepatitis and liver cancer |
| CN115671086B (en) * | 2022-11-09 | 2024-01-23 | 海南医学院第二附属医院 | Application of 5-hydroxy-1, 7-diphenyl-3-heptanone in preparation of medicines for preventing or treating liver cancer |
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