CN115109015B - 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 content of Total Cholesterol (TC) and total Triglyceride (TG) in the HepG2 high-fat cell model, and can be used as a hypolipidemic medicament.
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 elevated levels of Total Cholesterol (TC), triglycerides (TG) and low density lipoprotein cholesterol (LDL-C) in plasma, as well as reduced levels of high density lipoprotein cholesterol (HDL-C), associated with increased or delayed formation or 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): 345-367;EA TON C B,MD,MS.Primary Care:Clinics in Office Practice,2005,32 (4): 1027-1055). 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 lipid is an effective measure for preventing cardiovascular and cerebrovascular diseases, and is also an essential method (CROOKE R M, GRAHAM M J, LEMONIDIS K M, et al, journal of Lipid Research,2005,46 (5): 872-884;SONG D X,JIANG J G.Archives of Medical Research,2018,48 (7): 569-581;HERTZ R,SHEENA V,KALDERON B,et al.Biochemical Pharmacology,2001,61 (9): 1057-1062.).
Pennisetum (Equisetum ramosissimum Desf. Subsp. Deable (Roxb. Ex V.auch.) Hauke) is a plant of the genus Equisetum of the family Equisetaceae, and compounds isolated from the plant at present are mainly flavonoids, sterols, phenolic acids, alkaloids, megastimans, etc., whereas Megastimans isolated from the plant before have been C13-Megastimans, and no C16-Megastimans compounds have been reported; in addition, the report of the hypolipidemic activity of the plant is mainly focused on the aspect of crude extracts, but the research on the hypolipidemic activity of Megastigmane compounds is not reported.
Disclosure of Invention
It is an object of the present invention to provide compounds of the C16-Megastgmane class.
Another object of the invention is to provide a process for the preparation of C16-Megastgmane-like compounds.
It is another object of the present invention to provide a pharmaceutical composition.
It is a further object of the present invention to provide the use of a C16-Megastigmane compound or a pharmaceutical composition comprising the same.
Thus, according to one aspect, the present invention provides a C16-Megastigmane compound or a pharmaceutically acceptable ester thereof, said C16-Megastigmane compound being selected from the following compounds 1 to 4:
according to another aspect, the present invention provides a process for preparing the above-mentioned C16-Megastigmane-like compound, comprising the steps of:
s1, reflux-extracting the dry aerial parts of the pennisetum sinese by using 50% -70% ethanol (for example, 8-15 times by weight), and concentrating the extracting solution to obtain a concentrate;
s2, suspending the concentrate obtained in the step 1) by water, and then performing column chromatography by using D101 type macroporous adsorption resin, wherein water-ethanol with the volume ratio of 100:0, 70:30, 40:60 and 5:95 is used as an eluent for gradient elution 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 taking methanol-water with the volume ratio of 0:100, 10:90, 60:40 and 100:0 as an eluent 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 the condition of 10:90;
s4, separating the fraction Fr.2-2 by Sephadex LH-20 gel column chromatography, and isocratically eluting with methanol-water with a volume ratio of 10:90 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, subjecting the fraction Fr.2-2-7 to ODS column chromatography, and performing gradient elution by taking methanol-water with a volume ratio of 5:95, 10:90, 15:85, 20:80 and 30:70 as an eluent to obtain fractions Fr.2-2-7-1, fr.2-2-7-2, fr.2-2-7-3 and Fr.2-2-7-4, wherein the fractions Fr.2-2-7-4 are obtained under the condition of 15:85;
s6, eluting the fraction Fr.2-2-7-4 by using an C18 chromatographic column and acetonitrile-water with the volume ratio of 20:80 as a mobile phase to sequentially obtain the fraction Fr.2-2-7-4-1 and the fraction Fr.2-2-7-4-2;
s7, passing the fraction Fr.2-2-7-4-1 through a CHIRALPAK IG chromatographic column, eluting with acetonitrile-water with a volume ratio of 15:85 as a mobile phase, and sequentially obtaining a compound 1 and a compound 2;
s8, passing the fraction Fr.2-2-7-4-2 through a CHIRALPAK IG chromatographic column, eluting with acetonitrile-water as a mobile phase in a volume ratio of 20:80, and sequentially obtaining a compound 3 and a compound 4.
According to another aspect, the present invention provides a pharmaceutical composition comprising one or more of the following compounds 1-4, pharmaceutically acceptable esters thereof:
in some embodiments, the pharmaceutical composition may further comprise one or more pharmaceutically acceptable carriers. The pharmaceutically acceptable carrier may be any known in the art including, for example, fillers, diluents, solvents, sweeteners, surfactants, odorants, flavoring agents, lubricants and the like.
According to another aspect, the invention provides the use of a compound of the C16-Megastigmane class as described above or a pharmaceutically acceptable ester thereof in the preparation of a hypolipidemic agent.
According to another aspect, the present invention provides the use of the above pharmaceutical composition for the preparation of a hypolipidemic agent.
Experiments prove that the C16-Megastigmane compound can inhibit lipid accumulation in a HepG2 high-fat cell model induced by oleic acid, reduce the content of Total Cholesterol (TC) and total Triglyceride (TG) in the HepG2 high-fat cell model, and can be used as a hypolipidemic medicament. The C16-Megastigmane compound can be used as a medicament, and the composition of the medicament can be a monomer.
The present invention has been described in detail hereinabove, but the above embodiments are merely exemplary 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 summary or the following examples.
Unless explicitly stated otherwise, numerical ranges throughout this application include any subrange therein and any numerical value incremented by the smallest subunit in which a given value is present. Unless explicitly stated otherwise, numerical values throughout this application represent approximate measures or limits to include minor deviations from the given value and ranges of embodiments having about the stated value and having the exact value noted. Except in the operating examples provided last, all numerical values of parameters (e.g., amounts or conditions) in this application (including the appended claims) are to be understood in all cases as modified by the term "about" whether or not "about" actually appears before the numerical value. "about" means that the recited value allows for slight imprecision (with some approximation to the exact value; approximately or reasonably close to the value; approximated). "about" as used herein at least means variations that can be produced by ordinary methods of measuring and using these parameters if the imprecision provided by "about" is not otherwise understood in the art with this ordinary meaning. For example, "about" may include a change 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%.
Drawings
FIG. 1 shows the effect of compounds on the formation of lipid droplets in HepG2 cells at a concentration of 20. Mu.M. Ruler: 50 μm.
FIG. 2 shows the effect of compounds on Total Cholesterol (TC) and total Triglyceride (TG) levels in HepG2 cells at 20. Mu.M concentration.
Detailed Description
The invention will be further illustrated by the following examples in conjunction with the accompanying drawings.
The experimental methods used in the examples below are conventional methods unless otherwise specified.
Materials, reagents and the like used in the examples described below are commercially available unless otherwise specified.
Examples
Example 1: preparation of the C16-Megastigmane compound
1. Preparation of the compound:
1) Pulverizing the dry aerial parts of the pennisetum sinese, adding 8-15 times of 50% -70% ethanol, reflux-extracting for several times, mixing the extracting solutions, filtering, and concentrating under reduced pressure to obtain a concentrate;
2) Suspending the concentrate obtained in the step 1) with water, and then subjecting to D101 macroporous adsorption resin column (phi 20cm×200cm, tianjin allowed resin Co., ltd.) chromatography, and gradient eluting with water-ethanol as eluent at volume ratio of 100:0, 70:30, 40:60, 5:95 to obtain fractions Fr.1, fr.2, fr.3, fr.4, wherein fraction Fr.2 is obtained under 70:30 condition;
3) Separating fraction Fr.2 by polyamide column (phi 14cm×70cm, qingdao ocean chemical Co., ltd.) chromatography, gradient eluting with methanol-water with volume ratio of 0:100, 10:90, 60:40, 100:0, and bottling by thin layer chromatography analysis to obtain fractions Fr.2-1, fr.2-2, fr.2-3, fr.2-4, fr.2-5, wherein the fraction Fr.2-2 is obtained under 10:90 condition;
4) Separating fraction Fr.2-2 by Sephadex LH-20 gel column (phi 4 cm. Times.120 cm, pharmacia company), isocratically eluting with methanol-water with volume ratio of 10:90, and bottling by thin layer chromatography 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, fr.2-2-7;
5) Subjecting the fraction Fr.2-2-7 to ODS column (phi 4cm×20cm, pharmacia) chromatography, gradient eluting with methanol-water as eluent at volume ratio of 5:95, 10:90, 15:85, 20:80, 30:70, and bottling by thin layer chromatography to obtain fractions Fr.2-2-7-1, fr.2-2-7-2, fr.2-2-7-3, fr.2-2-7-4, wherein the fractions Fr.2-2-7-4 are obtained under 15:85;
6) Subjecting fraction Fr.2-2-7-4 to C18 chromatographic column (phi 4.6mm× 250mm,Nacalai tesque company), eluting with acetonitrile-water at volume ratio of 20:80 as mobile phase at flow rate of 1mL/min, and eluting according to 208nm liquid chromatogram to obtain fraction Fr.2-2-7-4-1, wherein fraction Fr.2-2-7-4-1 is obtained by eluting at 20 min, and fraction Fr.2-2-7-4-2 is obtained by eluting at 35 min;
7) Subjecting fraction Fr.2-2-7-4-1 to CHIRALPAK IG chromatographic column (phi 4.6mm×250mm, daxillon pharmaceutical chiral technology Co., ltd.) with acetonitrile-water as mobile phase at volume ratio of 15:85 and flow rate of 1mL/min, eluting to obtain compound 1 and compound 2 according to 208nm liquid chromatogram, wherein compound 1 is eluted at 14 min, and compound 2 is eluted at 15.5 min;
8) The fraction Fr.2-2-7-4-2 was passed through CHIRALPAK IG column chromatography (phi 4.6mm×250mm, daxillon pharmaceutical chiral technology Co., ltd.) and eluted with acetonitrile-water as mobile phase at a volume ratio of 20:80 at a flow rate of 1mL/min to obtain compound 3 and compound 4 according to a 208nm liquid chromatogram, wherein compound 3 was eluted at 20 min and compound 4 was eluted at 21 min.
Example 2: structural identification of the compound:
of compounds 1 H-NMR 13 The C-NMR data are shown in Table 1.
Table 1: compounds 1 to 4 1 H-NMR 13 C-NMR data (CD) 3 OD)
1 H NMR(600MHz)； 13 C NMR(150MHz)
Example 3: the C16-Megastigmane compound has the in-vitro lipid-lowering activity
1. Observation of Compounds on the formation of lipid droplets in HepG2 cells Using the oil Red O staining method
1.1 Experimental methods
(1) And (3) paving: taking 50000 HepG2 cells/hole in logarithmic growth phase, inoculating into a 24-hole plate, and culturing 500 mu L/hole;
(2) Preparation of sample solution: monomer compounds 1-4 were prepared with DMSO at 50mM, respectively, for use.
(3) Adding the medicine: hepG2 cells were cultured for 12h, and after the degree of fusion reached 70-80% by microscopic observation, the cells were starved for 12h by changing to serum-free DMEM medium, 500. Mu.L per well. After 12h, the blank group was changed to 500. Mu.L of serum-free medium, and the other groups were added with the inducer Oleic Acid (OA) per well (final concentration 80. Mu.M), 500. Mu.L/well. Adding a compound to be detected into the administration group, wherein the final concentration of the monomer compound is 20 mu M, and incubating in an incubator for 24 hours;
(4) Dyeing: after 24h incubation, the medium was discarded, washed 1 time with PBS (pre-chilled at 4 ℃) buffer, and 500. Mu.L of 4% paraformaldehyde fixative was added to each well to fix overnight at 4 ℃. The paraformaldehyde fixative was discarded, washed 1 time with PBS, rinsed with 60% isopropanol for 10min to enhance cell wall permeability, blotted with 60% isopropanol, stained with 500 μl of 0.3% oil red O stain per well for 1 hour at room temperature, then rinsed 1 time with 60% isopropanol, and washed 1 time with PBS buffer. Then, cell nuclei were stained, stained with light sappan wood for 10 minutes, and rinsed 2 times with PBS;
(5) And (3) observation: the intracellular red lipid droplet formation was observed using an inverted microscope.
1.2 experimental results
The results of the oil red O staining experiments (see fig. 1) show that the compounds inhibit oleic acid-induced lipid drop formation in HepG2 cells at a concentration of 20 μm.
2. Evaluation of Compounds for in vitro lipid lowering Activity by HepG2 intracellular TC, TG content assay
2.1 Experimental methods
(1) And (3) paving: inoculating HepG2 cells in logarithmic growth phase into 6-well plate with density of 2×10 5 2 mL/well of culture solution;
(2) Preparation of sample solution: monomer compounds 1-4 were prepared with DMSO at 50mM, respectively, for use.
(3) Adding the medicine: culturing for 12h, changing into serum-free DMEM medium after observing the fusion degree to 70-80% by microscope, and starving the cells for 12h with 500 mu L per well. After 12h, the blank group was changed to 500. Mu.L of serum-free medium and the other groups were added the inducer oleic acid OA (final concentration 80. Mu.M) per well, 500. Mu.L/well. Adding a compound to be detected into the administration group, wherein the final concentration of the monomer compound is 20 mu M, and incubating in an incubator for 24 hours;
(4) TC, TG content measurement:
1) Protein cleavage: after 24h incubation, the cells were placed on ice, the medium was discarded and washed 2 times with PBS (pre-chilled at 4 ℃). mu.L of cell lysate was added to each well and lysed on ice for 5 minutes. Cells were scraped off with a gun or cell scraper and transferred to a pre-chilled 1.5mL EP tube. Placed on ice and vortexed 1 time every 10min and 3 times altogether.
2) TC, TG content measurement: the test is carried out according to the steps of a TC/TG kit instruction book (Nanjing established technology Co., ltd., product number A110-1-1, A111-1-1), and the specific steps are as follows: the cell lysate was added to a 96-well plate according to Table 2, 3 multiplex wells were provided for each sample, mixed well after addition, incubated in an incubator at 37℃for 10min, and then OD values at 492nm were measured.
Table 2: TC, TG content determination
3) Protein concentration determination: the remaining sample solution was centrifuged at 12000rpm at 4℃for 10min, and the supernatant was assayed for protein concentration by BCA.
4) And (3) calculating:
cholesterol TC content (mmol/gprot) = (sample OD value-blank OD value)/(calibrated well OD value-blank OD value) ×5.17mmol/L
Triglyceride TG content (mmol/gprot) = (sample OD value-blank OD value)/(calibrated well OD value-blank OD value) ×2.26mmol/L
2.2 experimental results
TC and TG content measurement experiment results (see FIG. 2) show that the compounds 1, 2 and 4 can inhibit oleic acid-induced synthesis of cholesterol in HepG2 cells at the concentration of 20 mu M, and the compounds 1-4 can inhibit oleic acid-induced synthesis of triglyceride in HepG2 cells at the concentration of 20 mu M.
The above-described embodiments are merely preferred embodiments of the present invention and should not be construed as limiting the scope of the present invention. All equivalent changes and modifications within the scope of the present invention are intended to be covered by the present invention.
Claims (7)
1. A C16-Megastigmane compound selected from the following compounds 1-4:
2. a method for preparing a C16-Megastigmane compound, the C16-Megastigmane compound being selected from the following compounds 1 to 4:
the preparation method comprises the following steps:
s1, reflux-extracting the dry aerial parts of the herba inulae with 50% -70% ethanol, and concentrating the extracting solution to obtain a concentrate;
s2, suspending the concentrate obtained in the step 1) by water, and then performing column chromatography by using D101 type macroporous adsorption resin, wherein water-ethanol with the volume ratio of 100:0, 70:30, 40:60 and 5:95 is used as an eluent for gradient elution 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 taking methanol-water with the volume ratio of 0:100, 10:90, 60:40 and 100:0 as an eluent 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 the condition of 10:90;
s4, separating the fraction Fr.2-2 by Sephadex LH-20 gel column chromatography, and isocratically eluting with methanol-water with a volume ratio of 10:90 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, subjecting the fraction Fr.2-2-7 to ODS column chromatography, and performing gradient elution by taking methanol-water with a volume ratio of 5:95, 10:90, 15:85, 20:80 and 30:70 as an eluent to obtain fractions Fr.2-2-7-1, fr.2-2-7-2, fr.2-2-7-3 and Fr.2-2-7-4, wherein the fractions Fr.2-2-7-4 are obtained under the condition of 15:85;
s6, eluting the fraction Fr.2-2-7-4 by using an C18 chromatographic column and acetonitrile-water with the volume ratio of 20:80 as a mobile phase to sequentially obtain the 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, eluting with acetonitrile-water with a volume ratio of 15:85 as a mobile phase, and sequentially obtaining a compound 1 and a compound 2;
s8, passing the fraction Fr.2-2-7-4-2 through a CHIRALPAK IG chromatographic column, eluting with acetonitrile-water as a mobile phase in a volume ratio of 20:80, and sequentially obtaining a compound 3 and a compound 4.
3. A pharmaceutical composition comprising one or more of the following compounds 1-4:
4. the pharmaceutical composition of claim 3, wherein the pharmaceutical composition further comprises one or more pharmaceutically acceptable carriers.
5. The pharmaceutical composition of claim 4, wherein the pharmaceutically acceptable carrier is one or more selected from the group consisting of a filler, a diluent, a solvent, a sweetener, a surfactant, an odorant, a fragrance, and a lubricant.
6. Use of a C16-Megastigmane compound according to claim 1 for the preparation of a hypolipidemic medicament.
7. Use of a pharmaceutical composition according to any one of claims 3-5 for the preparation of a hypolipidemic medicament.
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| DE2960136D1 (en) * | 1978-02-09 | 1981-03-26 | Givaudan & Cie Sa | Megastigman-4,7-oxides(i) and 7-oxabicyclo(3,3,0)-octanes (ii), process for the preparation of (i) and (ii), use of (i) and (ii) as fragrances and/or flavours, and fragrance and/or flavour compositions containing (i) or (ii) |
| CN101167904B (en) * | 2007-11-09 | 2010-07-21 | 北京中科雍和医药技术有限公司 | Medicinal composition for treating hyperlipemia and its preparing process |
| JP5620629B2 (en) * | 2008-02-29 | 2014-11-05 | 学校法人近畿大学 | Fat metabolism improving agent obtained from hanging bonsai, medicine or food containing the fat metabolism improving agent, and novel megastigman and flavonoid compound obtained from hanging bonsai |
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