CN115109015A - C16-Megastigmane compound and preparation method and application thereof - Google Patents
C16-Megastigmane compound and preparation method and application thereof Download PDFInfo
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Abstract
The invention provides a C16-Megastigmane compound and a preparation method and application thereof. Experiments prove that the C16-Megastigmane compound can inhibit lipid accumulation in a HepG2 high-fat cell model induced by oleic acid, reduce the contents of Total Cholesterol (TC) and total Triglyceride (TG) in the HepG2 high-fat cell model, and can be used as a lipid-lowering drug.
Description
Technical Field
The invention belongs to the technical field of medicines, and particularly relates to a C16-Megastigmane compound, a preparation method thereof and application thereof as an anti-hyperlipidemia medicine.
Background
Hyperlipidemia refers to increased levels of Total Cholesterol (TC), Triglycerides (TG) and low-density lipoprotein cholesterol (LDL-C) in plasma, as well as decreased levels of high-density lipoprotein cholesterol (HDL-C), associated with increased production or delayed degradation of atherosclerotic lipoprotein particles, or decreased synthesis or increased degradation of protective lipoprotein particles (XIE W, ZHAO Y, DU L. journal of Ethnopharmacology,2012,140(2): 345-. The incidence of atherosclerosis and heart disease is closely related to excessive blood lipid levels, while lowering total cholesterol levels in serum can reduce the incidence of myocardial infarction and coronary heart disease. Therefore, lowering blood lipids is an effective measure for preventing cardiovascular and cerebrovascular diseases, and is also a necessary method (CROOKE R M, GRAHAM J, LEMONIDIS K M, et al. journal of Lipid Research,2005,46(5): 872-.
Ramose scouring rush (Equisetum ramosissimum Desf. subsp. debale (Roxb. ex V auch.) Hauke) is a plant of the genus Equisetum in the family Equisetaceae, and the compounds isolated from the plant at present are mainly flavonoids, sterols, phenolic acids, alkaloids, Megastigmanes, etc., while the Megastigmanes isolated from the plant at present are all C13-Megastigmane, and the C16-Megastigmane compounds have never been reported; in addition, reports of the hypolipidemic activity of the plant mainly focus on the aspect of crude extracts of the plant, and no report is found about the hypolipidemic activity research of Megastigmane compounds.
Disclosure of Invention
An object of the present invention is to provide compounds of the C16-Megastigmane class.
Another object of the present invention is to provide a process for the preparation of C16-Megastigmane compounds.
It is another object of the present invention to provide a pharmaceutical composition.
Another object of the present invention is to provide the use of a compound of the C16-Megastigmane class or a pharmaceutical composition comprising the same.
Thus, according to one aspect, the present invention provides a compound of the C16-Megastigmane class, or a pharmaceutically acceptable ester thereof, said compound of the C16-Megastigmane class being selected from the following compounds 1-4:
according to another aspect, the present invention provides a process for preparing the above-mentioned C16-Megastigmane compound, comprising the steps of:
s1, reflux-extracting the dried aerial parts of the equisetum ramosissimum with 50-70% ethanol (for example, 8-15 times of the weight), and concentrating the extracting solution to obtain a concentrate;
s2, suspending the concentrate obtained in the step 1) with water, performing D101 type macroporous adsorption resin column chromatography, and performing gradient elution by using water-ethanol with the volume ratio of 100:0, 70:30, 40:60 and 5:95 as eluent to obtain fractions Fr.1, Fr.2, Fr.3 and Fr.4, wherein the fraction Fr.2 is obtained under the condition of 70: 30;
s3, separating the fraction Fr.2 by polyamide column chromatography, and performing gradient elution by using methanol-water as an eluent in a volume ratio of 0:100, 10:90, 60:40 and 100:0 to obtain fractions Fr.2-1, Fr.2-2, Fr.2-3, Fr.2-4 and Fr.2-5, wherein the fraction Fr.2-2 is obtained under a condition of 10: 90;
s4, separating the fraction Fr.2-2 by Sephadex LH-20 gel column chromatography, eluting with methanol-water at a volume ratio of 10:90 as eluent at equal intervals to obtain fractions Fr.2-2-1, Fr.2-2-2, Fr.2-2-3, Fr.2-2-4, Fr.2-2-5, Fr.2-2-6 and Fr.2-2-7 in sequence;
s5, performing ODS column chromatography on the fraction Fr.2-2-7 to obtain fractions Fr.2-2-7-1, Fr.2-2-7-2, Fr.2-2-7-3 and Fr.2-2-7-4 by gradient elution with methanol-water as an eluent in a volume ratio of 5:95, 10:90, 15:85, 20:80 and 30:70, wherein the fractions Fr.2-2-7-4 are obtained under a condition of 15: 85;
s6, passing the fraction Fr.2-2-7-4 through a C18 chromatographic column, eluting by using acetonitrile-water as a mobile phase with the volume ratio of 20:80, and sequentially obtaining fractions Fr.2-2-7-4-1 and Fr.2-2-7-4-2;
s7, passing the fraction Fr.2-2-7-4-1 through a CHIRALPAK IG chromatographic column, and eluting by using acetonitrile-water as a mobile phase in a volume ratio of 15:85 to sequentially obtain a compound 1 and a compound 2;
s8, passing the fraction Fr.2-2-7-4-2 through a CHIRALPAK IG chromatographic column, and eluting by using acetonitrile-water as a mobile phase in a volume ratio of 20:80 to sequentially obtain a compound 3 and a compound 4.
According to another aspect, the present invention provides a pharmaceutical composition comprising one or more selected from the following compounds 1-4, pharmaceutically acceptable esters thereof:
in some embodiments, the pharmaceutical composition may further comprise one or more pharmaceutically acceptable carriers. Such pharmaceutically acceptable carriers may be well known in the art and include, for example, fillers, diluents, solvents, sweeteners, surfactants, odorants, flavoring agents, lubricants, and the like.
According to another aspect, the invention provides the use of the C16-Megastigmane compound or the pharmaceutically acceptable ester thereof in the preparation of a medicament for reducing blood fat.
According to another aspect, the invention provides the use of the pharmaceutical composition in the preparation of a medicament for reducing blood lipid.
Experiments prove that the C16-Megastigmane compound can inhibit lipid accumulation in a HepG2 high-fat cell model induced by oleic acid, reduce the contents of Total Cholesterol (TC) and total Triglyceride (TG) in the HepG2 high-fat cell model, and can be used as a lipid-lowering drug. The C16-Megastigmane compound can be used as a drug, and the drug can be a monomer.
The present invention has been described in detail hereinabove, but the above embodiments are merely illustrative in nature and are not intended to limit the present invention. Furthermore, there is no intention to be bound by any theory presented in the preceding prior art or the summary or the following examples.
Unless expressly stated otherwise, a numerical range throughout this specification includes any sub-range therein and any numerical value incremented by the smallest sub-unit within a given value. Unless expressly stated otherwise, numerical values throughout this specification represent approximate measures or limitations to the extent that such deviations from the given values, as well as embodiments having approximately the stated values and having the exact values stated, are included. Other than in the operating examples provided at the end of the detailed description, all numbers expressing quantities or conditions of parameters (e.g., quantities or conditions) used in the specification (including the appended claims) are to be understood as being modified in all instances by the term "about" whether or not "about" actually appears before the number. "about" means that the numerical value so stated is allowed to be somewhat imprecise (with some approach to exactness in that value; about or reasonably close to that value; approximately). As used herein, "about" refers to at least variations that can be produced by ordinary methods of measuring and using such parameters, provided that the imprecision provided by "about" is not otherwise understood in the art with this ordinary meaning. For example, "about" can include variations of less than or equal to 10%, less than or equal to 5%, less than or equal to 4%, less than or equal to 3%, less than or equal to 2%, less than or equal to 1%, or less than or equal to 0.5%.
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FIG. 1 shows the effect of compound at a concentration of 20 μm on lipid droplet formation in HepG2 cells. A scale: 50 μm.
Figure 2 shows the effect of compounds at a concentration of 20 μ Μ on Total Cholesterol (TC) and total Triglyceride (TG) content in HepG2 cells.
Detailed Description
The following examples will further illustrate the present invention with reference to the accompanying drawings.
The experimental procedures used in the following examples are all conventional procedures unless otherwise specified.
Materials, reagents and the like used in the following examples are commercially available unless otherwise specified.
Examples
Example 1: preparation of C16-Megastigmane compound
1. Preparation of the compound:
1) crushing the dried overground part of the equisetum ramosissimum, adding 50-70% ethanol in an amount which is 8-15 times that of the crushed overground part of the equisetum ramosissimum, performing reflux extraction for a plurality of times, combining extracting solutions, filtering, and performing reduced pressure concentration to obtain a concentrate;
2) suspending the concentrate obtained in the step 1) with water, then carrying out chromatography by using a D101 type macroporous adsorption resin column (phi 20cm is multiplied by 200cm, Tianjin allows resin Co., Ltd.), and carrying out gradient elution by using water-ethanol as an eluent with the volume ratio of 100:0, 70:30, 40:60 and 5:95 respectively to obtain fractions Fr.1, Fr.2, Fr.3 and Fr.4, wherein the fraction Fr.2 is obtained under the condition of 70: 30;
3) separating the fraction Fr.2 by polyamide column chromatography (phi 14cm × 70cm, Qingdao ocean chemical Co., Ltd.), gradient eluting with methanol-water at volume ratio of 0:100, 10:90, 60:40, 100:0 as eluent, mixing the eluates by thin layer chromatography to obtain fractions Fr.2-1, Fr.2-2, Fr.2-3, Fr.2-4, and Fr.2-5, wherein the fraction Fr.2-2 is obtained at 10: 90;
4) subjecting fraction Fr.2-2 to Sephadex LH-20 gel column (phi 4cm × 120cm, Pharmacia) chromatography, eluting with methanol-water at volume ratio of 10:90, and performing TLC analysis to obtain fractions Fr.2-2-1, Fr.2-2-2, Fr.2-2-3, Fr.2-2-4, Fr.2-2-5, Fr.2-2-6, and Fr.2-2-7;
5) subjecting fraction Fr.2-2-7 to ODS column (phi 4cm × 20cm, Pharmacia) chromatography, eluting with methanol-water at volume ratio of 5:95, 10:90, 15:85, 20:80, and 30:70 as eluent, and performing thin layer chromatography to obtain fraction Fr.2-2-7-1, fraction Fr.2-2-7-2, fraction Fr.2-2-7-3, and fraction Fr.2-2-7-4, wherein fraction Fr.2-2-7-4 is obtained at 15: 85;
6) subjecting fraction Fr.2-2-7-4 to C18 chromatographic column (Φ 4.6mm × 250mm, Nacalai tesque Co., Ltd.), eluting with acetonitrile-water at a volume ratio of 20:80 as mobile phase at a flow rate of 1mL/min, and obtaining fraction Fr.2-2-7-4-1 and fraction Fr.2-2-7-4-2 according to 208nm liquid chromatogram, wherein fraction Fr.2-2-7-4-1 is eluted at 20 min, and fraction Fr.2-2-7-4-2 is eluted at 35 min;
7) subjecting the fraction Fr.2-2-7-4-1 to CHIRALPAK IG chromatographic column (phi 4.6mm × 250mm, Daluol drug chiral technology Co., Ltd.), eluting with acetonitrile-water at volume ratio of 15:85 as mobile phase at flow rate of 1mL/min, and obtaining compound 1 and compound 2 according to 208nm liquid chromatogram, wherein compound 1 is obtained by eluting in 14 min, and compound 2 is obtained by eluting in 15.5 min;
8) subjecting the fraction Fr.2-2-7-4-2 to CHIRALPAK IG chromatographic column (phi 4.6mm × 250mm, Daluol drug chiral technology Co., Ltd.), eluting with acetonitrile-water at a volume ratio of 20:80 as mobile phase at a flow rate of 1mL/min, and obtaining compound 3 and compound 4 according to 208nm liquid chromatogram, wherein compound 3 is eluted at 20 min and compound 4 is eluted at 21 min.
Example 2: structural identification of the compounds:
process for preparing compounds 1 H-NMR and 13 the C-NMR data are shown in Table 1.
Table 1: of compounds 1 to 4 1 H-NMR and 13 C-NMR data (CD) 3 OD)
1 H NMR(600MHz)； 13 C NMR(150MHz)
Example 3: in vitro lipid-lowering activity of C16-Megastigmane compounds
1. Effect of compounds on lipid droplet formation in HepG2 cells by oil red O staining
1.1 Experimental methods
(1) Plate paving: 50000 cells/hole of HepG2 in logarithmic phase are inoculated in a 24-hole plate, and 500 mu L of culture solution/hole;
(2) preparation of sample solution: monomeric compounds 1-4 were each prepared in DMSO to 50mM for use.
(3) Adding medicine: HepG2 cells were cultured for 12 hours, and after the confluency reached 70-80% by microscopic observation, the cells were starved for 12 hours by changing to serum-free DMEM medium at 500. mu.L per well. After 12h, the blank was replaced with 500. mu.L of serum-free medium, and the other groups were supplemented with 500. mu.L/well of inducer Oleic Acid (OA) (final concentration 80. mu.M). Adding a compound to be tested into the administration group, wherein the final concentration of the monomer compound is 20 mu M, and incubating in an incubator for 24 h;
(4) dyeing: after 24h incubation, the medium was discarded, washed 1 time with PBS (pre-cooled at 4 ℃ C.) buffer, and 500. mu.L of 4% paraformaldehyde fixative was added to each well and fixed overnight at 4 ℃. The paraformaldehyde fixing solution is discarded, the fixed solution is washed by PBS for 1 time, 60% isopropanol is rinsed for 10min to enhance the permeability of cell walls, 60% isopropanol is absorbed, 500 mu L of 0.3% oil red O staining solution is added into each hole, the dyeing is carried out for 1h under the room temperature condition, then the fixed solution is rapidly rinsed by 60% isopropanol for 1 time, and the buffer solution of PBS is washed for 1 time. Then, cell nucleus staining is carried out, and after staining is carried out for 10 minutes by sapanwood, the cell nucleus is rinsed for 2 times by PBS;
(5) and (4) observation: the formation of red lipid droplets in the cells was observed using an inverted microscope.
1.2 results of the experiment
The results of the oil red O staining experiments (see figure 1) show that the compounds inhibit oleic acid-induced lipid droplet formation in HepG2 cells at a concentration of 20 μ M.
2. Evaluation of in vitro lipid-lowering Activity of Compounds by assay of TC and TG content in HepG2 cells
2.1 Experimental methods
(1) Plate paving: HepG2 cells in logarithmic growth phase were inoculated in 6-well plates at a density of 2X 10 5 2 mL/hole of culture solution;
(2) preparation of sample solution: monomeric compounds 1-4 were each prepared in DMSO to 50mM for use.
(3) Adding medicine: culturing for 12h, observing the fusion degree to 70-80% by microscope, and then replacing with serum-free DMEM medium, wherein each well contains 500 μ L of the serum-free DMEM medium, and starving the cells for 12 h. After 12h, the blank was replaced with 500. mu.L of serum-free medium, and the other groups were supplemented with 500. mu.L/well of the inducer oleic acid OA (final concentration 80. mu.M). Adding a compound to be tested into the administration group, wherein the final concentration of the monomer compound is 20 mu M, and incubating in an incubator for 24 h;
(4) and (3) measuring TC and TG contents:
1) protein cleavage: after 24h incubation, cells were placed on ice, the medium was discarded and washed 2 times with PBS (pre-chilled at 4 ℃ C.) buffer. Add 100. mu.L of cell lysate to each well and lyse for 5 min on ice. The cells were scraped off with a pipette tip or cell scraper and transferred to a pre-chilled 1.5mL EP tube. Place on ice, vortex 1 time every 10min, 3 times in total.
2) And (3) measuring TC and TG contents: the test is carried out according to the steps of TC \ TG kit specifications (Nanjing Kangji science and technology Co., Ltd., product numbers A110-1-1 and A111-1-1), and the specific steps are as follows: adding the cell lysate into a 96-well plate according to the table 2, setting 3 multiple wells for each sample, uniformly mixing after adding, placing in an incubator at 37 ℃ for incubation for 10min, and then measuring the OD value at 492 nm.
Table 2: measurement of TC and TG contents
3) Protein concentration determination: the remaining sample solution was centrifuged at 4 ℃ and 12000rpm for 10min, and the supernatant was collected to determine the protein concentration by BCA method.
4) And (3) calculating:
cholesterol TC content (mmol/gprot) ═ sample OD value-blank OD value)/(calibration well OD value-blank OD value) × 5.17mmol/L
Triglyceride TG content (mmol/gprot) ═ sample OD value-blank OD value)/(calibration well OD value-blank OD value) × 2.26mmol/L
2.2 results of the experiment
The results of the TC and TG assay experiments (see fig. 2) show that compounds 1, 2 and 4 can inhibit oleic acid-induced intracellular cholesterol synthesis from HepG2 at a concentration of 20 μ M, and compounds 1-4 can inhibit oleic acid-induced intracellular triglyceride synthesis from HepG2 at a concentration of 20 μ M.
The above-described embodiments are merely preferred embodiments of the present invention, and should not be construed as limiting the scope of the invention. All equivalent changes and modifications made within the scope of the present invention shall fall within the scope of the present invention.
Claims (7)
1. A C16-Megastigmane class compound or a pharmaceutically acceptable ester thereof, said C16-Megastigmane class compound being selected from the group consisting of compounds 1-4:
2. a method for preparing a C16-Megastigmane compound, wherein the C16-Megastigmane compound is selected from the following compounds 1-4:
the preparation method comprises the following steps:
s1, reflux-extracting the dried aerial parts of the pennisetum purpureum with 50-70% ethanol, and concentrating the extracting solution to obtain a concentrate;
s2, suspending the concentrate obtained in the step 1) with water, performing D101 type macroporous adsorption resin column chromatography, and performing gradient elution by using water-ethanol with the volume ratio of 100:0, 70:30, 40:60 and 5:95 as eluent to obtain fractions Fr.1, Fr.2, Fr.3 and Fr.4, wherein the fraction Fr.2 is obtained under the condition of 70: 30;
s3, separating the fraction Fr.2 by polyamide column chromatography, and performing gradient elution by using methanol-water as an eluent in a volume ratio of 0:100, 10:90, 60:40 and 100:0 to obtain fractions Fr.2-1, Fr.2-2, Fr.2-3, Fr.2-4 and Fr.2-5, wherein the fraction Fr.2-2 is obtained under a condition of 10: 90;
s4, separating the fraction Fr.2-2 by Sephadex LH-20 gel column chromatography, eluting with methanol-water at a volume ratio of 10:90 as eluent at equal intervals to obtain fractions Fr.2-2-1, Fr.2-2-2, Fr.2-2-3, Fr.2-2-4, Fr.2-2-5, Fr.2-2-6 and Fr.2-2-7 in sequence;
s5, performing ODS column chromatography on the fraction Fr.2-2-7 to obtain fractions Fr.2-2-7-1, Fr.2-2-7-2, Fr.2-2-7-3 and Fr.2-2-7-4 by gradient elution with methanol-water as an eluent in a volume ratio of 5:95, 10:90, 15:85, 20:80 and 30:70, wherein the fractions Fr.2-2-7-4 are obtained under a condition of 15: 85;
s6, passing the fraction Fr.2-2-7-4 through a C18 chromatographic column, and eluting by using acetonitrile-water as a mobile phase with the volume ratio of 20:80 to sequentially obtain a fraction Fr.2-2-7-4-1 and a fraction Fr.2-2-7-4-2;
s7, passing the fraction Fr.2-2-7-4-1 through a CHIRALPAK IG chromatographic column, and eluting by using acetonitrile-water as a mobile phase in a volume ratio of 15:85 to sequentially obtain a compound 1 and a compound 2;
s8, passing the fraction Fr.2-2-7-4-2 through a CHIRALPAK IG chromatographic column, and eluting by using acetonitrile-water as a mobile phase in a volume ratio of 20:80 to sequentially obtain a compound 3 and a compound 4.
3. A pharmaceutical composition comprising one or more selected from the following compounds 1-4, pharmaceutically acceptable esters thereof:
4. the pharmaceutical composition of claim 3, wherein the pharmaceutical composition further comprises one or more pharmaceutically acceptable carriers.
5. The pharmaceutical composition according to claim 4, wherein the pharmaceutically acceptable carrier is one or more selected from the group consisting of fillers, diluents, solvents, sweeteners, surfactants, odorants, flavoring agents and lubricants.
6. Use of the C16-Megastigmane of claim 1 or a pharmaceutically acceptable ester thereof for the manufacture of a hypolipidemic agent.
7. Use of a pharmaceutical composition according to any one of claims 3-5 in the preparation of a medicament for lowering blood lipid.
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| CN115490584A (en) * | 2022-09-28 | 2022-12-20 | 厦门中药厂有限公司 | Megastigmane compound and preparation method and application thereof |
| CN115557923A (en) * | 2022-09-28 | 2023-01-03 | 厦门中药厂有限公司 | C16-ionol compound and preparation method and application thereof |
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| XU XIAO-HONG等: "Megastigmanes and Flavonoid Glycosides of Equisetum debile", 《CHIN J NAT MED.》 * |
| 黄丹娜等: "节节草的研究进展", 《广西中医药》 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115490584A (en) * | 2022-09-28 | 2022-12-20 | 厦门中药厂有限公司 | Megastigmane compound and preparation method and application thereof |
| CN115557923A (en) * | 2022-09-28 | 2023-01-03 | 厦门中药厂有限公司 | C16-ionol compound and preparation method and application thereof |
| CN115557923B (en) * | 2022-09-28 | 2023-09-05 | 厦门中药厂有限公司 | C16-ionol compound and preparation method and application thereof |
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| CN115109015B (en) | 2023-06-27 |
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