CN111943920B - Phloroglucinol compound Hyperacmosin D and application thereof in preparation of antidiabetic drugs - Google Patents
Phloroglucinol compound Hyperacmosin D and application thereof in preparation of antidiabetic drugs Download PDFInfo
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- CN111943920B CN111943920B CN201910401940.4A CN201910401940A CN111943920B CN 111943920 B CN111943920 B CN 111943920B CN 201910401940 A CN201910401940 A CN 201910401940A CN 111943920 B CN111943920 B CN 111943920B
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Abstract
The invention relates to a phloroglucinol compound Hyperacmosin D obtained by first extraction and separation from hypericum aculeatum (Hypericum acmosepaium N.Robson), a preparation method and application thereof. The biological activity test shows that: the compound Hyperacmosin D has good hypoglycemic effect, and can be used for preparing antidiabetic drugs.
Description
Technical Field
The invention relates to the technical field of medicines. Relates to a phloroglucinol compound Hyperacmosin D extracted and separated from aerial parts of hypericum (Hypericum acmosepaium N.Robson), a preparation method thereof and application thereof in antidiabetic activity treatment.
Background
The Hypericum acuminatum is a plant of Hypericum of Guttiferae, and is also called: the balsam pear tree. Distributed in Guangxi, sichuan, guizhou, yunnan and other places in China. The Chinese medicinal composition is used for relieving inflammation and swelling, and treating hepatitis. The chemical components of the traditional Chinese medicine are less studied in modern times, and the traditional Chinese medicine is not used as a traditional Chinese medicine prescription. However, a great number of documents report that phloroglucinol compounds have a series of good pharmacological activities such as antivirus, anti-inflammatory and the like, and hypericum japonicum is rich in phloroglucinol components, so that further research and explanation on chemical components and potential effects of the phloroglucinol compounds are significant in playing roles.
Disclosure of Invention
The invention solves the technical problem of providing a phloroglucinol compound Hyperacmosin D and pharmaceutically acceptable salts thereof, which are extracted and separated from hypericum acuminatum for the first time, and a preparation method and application thereof.
In order to solve the technical problems of the invention, the invention provides the following technical scheme:
according to the technical scheme, the invention provides a phloroglucinol compound Hyperacmosin D and pharmaceutically acceptable salts thereof, and the compound has the following structure:
the second aspect of the technical scheme of the invention provides a preparation method of a phloroglucinol compound Hyperacmosin D, which is separated from aerial parts of hypericum acuminatum, and comprises the following specific steps:
extracting: extracting ground parts of the crushed hypericum japonicum with ethanol, and concentrating the obtained extracting solution to obtain crude extract; dissolving the crude extract in water, suspending uniformly, extracting with petroleum ether, and concentrating the obtained extract to obtain petroleum ether extract.
Separating: carrying out silica gel column chromatography on petroleum ether extract, and carrying out gradient elution for the first time by petroleum ether/ethyl acetate, wherein the volume ratio of petroleum ether/ethyl acetate is 1:0, further performing reduced pressure column chromatography by using a medium pressure chromatographic gel packing, eluting with 75% ethanol, 85% ethanol, 95% ethanol and acetone, eluting with two column volumes of each solvent, wherein each column volume is a component, and the total number of the components is A, B, C, D, E, F, G, H, further performing silica gel column chromatography by using 85% ethanol eluting component C, performing gradient elution with petroleum ether/ethyl acetate for the second time, eluting with two column volumes of each solvent, and sequentially performing gradient elution with petroleum ether/ethyl acetate at a concentration of volume ratio of 1:0,9:1,4:1,2:1,0:1, obtaining 20 components in total of C1-C20, wherein the volume ratio of petroleum ether to ethyl acetate is 9:1 elution part No. C6 prepared high performance liquid chromatography column with methanol/water volume ratio 95:5 eluting to obtain the compound Hyperacmosin D.
In the above preparation method, in the extraction step, the ethanol used was 95% ethanol.
In the above preparation method, in the extraction step, the extraction adopts a method of heating reflux extraction.
In the preparation method, in the separation step, the gradient elution concentration of petroleum ether/ethyl acetate for the first time is sequentially 1 by volume: 0,9:1,2:1,0:1.
in the preparation method, in the separation step, the gradient elution concentration of the petroleum ether/ethyl acetate for the second time is sequentially 1 by volume: 0,9:1,4:1,2:1,0:1.
in the above preparation method, in the separation step, the column packing of the preparative HPLC is reverse-phase octadecyl bonded silica gel.
According to a third aspect of the technical scheme, the invention provides a pharmaceutical composition, which is characterized by comprising the phloroglucinol compound in claim 1 and pharmaceutically acceptable salts or additives, and the application of the phloroglucinol compound in claim 1 and pharmaceutically acceptable salts thereof in antidiabetic therapeutic drugs.
The pharmaceutical compositions may be prepared according to methods well known in the art. Any dosage form suitable for human or animal use may be made by combining the compounds of the invention with one or more pharmaceutically acceptable solid or liquid excipients and/or adjuvants. The compounds of the present invention are typically present in the pharmaceutical compositions thereof in an amount of 0.1 to 95% by weight.
The compounds of the present invention or pharmaceutical compositions containing them may be administered in unit dosage form by the enteral or parenteral route, such as oral, intravenous, intramuscular, subcutaneous, nasal, oral mucosal, ocular, pulmonary and respiratory, cutaneous, vaginal, rectal, etc.
The dosage form may be a liquid, solid or semi-solid dosage form. The liquid preparation can be solution (including true solution and colloid solution), emulsion (including o/w type, w/o type and multiple emulsion), suspension, injection (including injection solution, powder injection and transfusion), eye drop, nasal drop, lotion, liniment, etc.; the solid dosage forms can be tablets (including common tablets, enteric coated tablets, buccal tablets, dispersible tablets, chewable tablets, effervescent tablets, orally disintegrating tablets), capsules (including hard capsules, soft capsules and enteric coated capsules), granules, powder, micropills, dripping pills, suppositories, films, patches, aerosol (powder) and sprays; the semisolid dosage form may be an ointment, gel, paste, or the like.
The compound of the invention can be prepared into common preparations, slow release preparations, controlled release preparations, targeted preparations and various microparticle administration systems.
For the preparation of the compounds of the present invention into tablets, various excipients known in the art may be widely used, including diluents, binders, wetting agents, disintegrants, lubricants, cosolvents. The diluent can be starch, dextrin, sucrose, glucose, lactose, mannitol, sorbitol, xylitol, microcrystalline cellulose, calcium sulfate, calcium hydrogen phosphate, calcium carbonate, etc.; the wetting agent can be water, ethanol, isopropanol, etc.; the binder may be starch slurry, dextrin, syrup, mel, glucose solution, microcrystalline cellulose, acacia slurry, gelatin slurry, sodium carboxymethyl cellulose, methyl cellulose, hydroxypropyl methylcellulose, ethyl cellulose, acrylic resin, carbomer, polyvinylpyrrolidone, polyethylene glycol, etc.; the disintegrating agent can be dry starch, microcrystalline cellulose, low-substituted hydroxypropyl cellulose, cross-linked polyvinylpyrrolidone, cross-linked sodium carboxymethyl cellulose, sodium carboxymethyl starch, sodium bicarbonate and citric acid, polyoxyethylene sorbitol fatty acid ester, sodium dodecyl sulfonate, etc.; the lubricant and cosolvent can be talcum powder, silicon dioxide, stearate, tartaric acid, liquid paraffin, polyethylene glycol, etc.
The tablets may be further formulated into coated tablets, such as sugar coated tablets, film coated tablets, enteric coated tablets, or bilayer and multilayer tablets.
In order to prepare the administration unit into a capsule, the compound of the present invention as an active ingredient may be mixed with a diluent and a cosolvent, and the mixture may be directly placed in a hard capsule or a soft capsule. The active ingredient of the compound can be prepared into particles or pellets by mixing with a diluent, an adhesive and a disintegrating agent, and then placed into hard capsules or soft capsules. The various diluents, binders, wetting agents, disintegrants and co-solvents used to prepare tablets of the compounds of the invention may also be used to prepare capsules of the compounds of the invention.
For the preparation of the compound of the present invention into injection, water, ethanol, isopropanol, propylene glycol or their mixture may be used as solvent, and appropriate amount of solubilizer, cosolvent, pH regulator and osmotic pressure regulator commonly used in the art may be added. The solubilizer or cosolvent can be poloxamer, lecithin, hydroxypropyl-beta-cyclodextrin, etc.; the pH regulator can be phosphate, acetate, hydrochloric acid, sodium hydroxide, etc.; the osmotic pressure regulator can be sodium chloride, mannitol, glucose, phosphate, acetate, etc. For example, mannitol, glucose, etc. can be added as propping agent for preparing lyophilized powder for injection.
In addition, colorants, preservatives, fragrances, flavoring agents, or other additives may also be added to the pharmaceutical formulation, if desired.
For the purpose of administration, the drug or the pharmaceutical composition of the present invention can be administered by any known administration method to enhance the therapeutic effect.
The dosage of the pharmaceutical composition of the present invention may vary widely depending on the nature and severity of the disease to be prevented or treated, the individual condition of the patient or animal, the route of administration and the dosage form, etc. Generally, the suitable daily dosage of the compounds of the present invention will range from 0.001 to 5mg/Kg of body weight. The above-mentioned dosages may be administered in one dosage unit or in several dosage units, depending on the clinical experience of the physician and the dosage regimen involved in the application of other therapeutic means.
The compounds or compositions of the present invention may be administered alone or in combination with other therapeutic or symptomatic agents. When the compound of the present invention has a synergistic effect with other therapeutic agents, its dosage should be adjusted according to the actual circumstances.
According to a fourth aspect of the technical scheme, the invention provides application of a compound Hyperacmosin D and pharmaceutically acceptable salts thereof in preparation of antidiabetic medicines.
Beneficial technical effects
The invention adopts a method for evaluating the glucose consumption experiment and the hepatic cell injury protection effect caused by APAP in vitro by using a monomer compound. Experiments prove that the compound Hyperacmosin D has better hypoglycemic effect and can be used for preparing antidiabetic drugs.
Drawings
Fig. 1: effect of Hyperacmosin D on glucose consumption by HepG2 cells. Veh: normal control; ins: insulin.
Detailed Description
The chemical formula of Hyperacmosin D (the arabic numerals in the formula are the index of carbon atoms in the chemical structure) referred to in the examples is as follows:
EXAMPLE 1 preparation of Hyperacmosin D
Extracting: 17.0kg of aerial parts of dry hypericum (Hypericum acmosepaium N.Robson) are crushed and extracted for 3 times by heating and refluxing with 95% ethanol, and the obtained extract is decompressed and concentrated to obtain crude extract; dissolving the crude extract in water, suspending uniformly, extracting with petroleum ether for three times, and concentrating the obtained extract under reduced pressure to obtain petroleum ether extract.
Separating: subjecting petroleum ether extract to silica gel column chromatography, subjecting the petroleum ether extract to silica gel column chromatography, gradient eluting with petroleum ether/ethyl acetate,
the gradient elution concentrations of petroleum ether/ethyl acetate were in sequence with a volume ratio of 1:0,9:1,2:1,0:1.
combining similar fractions according to TLC anisaldehyde color development to obtain 11 components Fr.1-11;
wherein the volume ratio of the component Fr.1, namely petroleum ether/ethyl acetate is 1: the eluted part 0 is further subjected to MCI pressure-reducing column chromatography, eluting with 75%, 85%, 95% ethanol and acetone,
the similar fractions were combined according to TLC development to give 8 fractions A, B, C, D, E, F, G, H.
The component C is further subjected to silica gel column chromatography, petroleum ether/ethyl acetate gradient elution is carried out,
petroleum ether/ethyl acetate volume ratio 1:0,9:1,4:1,2:1,0:1.
the similar fractions were combined according to TLC anisaldehyde color development to give 20 fractions, petroleum ether/ethyl acetate volume ratio 9: the eluted fraction of 1 is component C6.
Through preparative HPLC [ C ] 18 Column (5 μm,250×10 mm) methanol/water 95:5 volume ratio elution, flow rate 3mL/min, detection at 254nm wavelength) to give the compound Hyperacmosin D (12 mg).
And (3) structural identification: according to the conventional technology of modern spectrum such as NMR, HRESIMS, UV, IR and optical rotation, the chemical structure of the compound Hyperacmosin D is determined, and the physicochemical properties are as follows:
Hyperacmosin D：
colorless oily with formula C 37 H 58 O 6 ；
UV spectrum (MeOH) lambda max (logε)204(3.84)nm；
IR (KBr) v of infrared spectrum max ；3397,2969,2925,1758,1715,1448,1380cm -1 ；
Round dichromatic ECD (MeOH) lambda max (Δε)312.5(-2.76)nm；
High resolution mass spectrum HRESIMS m/z 621.41256[ M+Na] + (calculated for C 37 H 58 O 6 ,621.41168)；
Nuclear magnetic resonance hydrogen spectrum of Hyperacmosin D 1 H NMR (500 MHz) and nuclear magnetic resonance carbon spectrum 13 C NMR (125 MHz) data are shown in Table I.
TABLE I Hyperacmosin D 1 H and 13 C NMR(ppm in CDCl 3 )
experimental example 1 Effect of Hyperacmosin D on glucose consumption in cells
Experimental sample
Configuration of the sample solution to be tested: the test sample was the pure compound prepared in example 1 (Hyperacmosin D). Accurately weighing a proper amount of sample, and preparing a 0.1M storage solution by using DMSO for pharmacological activity test.
Cell lines: human liver cancer HepG2 cells. Growing in DMEM culture solution (penicillin 100U/ml, streptomycin 100 μg/ml) containing 10% foetal calf serum at 37deg.C under 5% CO 2 Saturated humidity. Passaging was digested with 0.25% trypsin and 0.02% edta.
Experimental method
HepG2 cells were inoculated into 96-well cell culture plates, and after 24 hours of culture, the sugar-free medium was changed the next day for dosing, and positive drug control groups (insulin), solvent blank control groups and model groups were set at the same time, the concentration of insulin was 0.03. Mu.M, and the drug action concentrations were 0.1. Mu.M and 1. Mu.M. After 24h incubation, the supernatant was taken for glucose consumption, CCK8 was added for cell viability, 10. Mu.L of supernatant medium was aspirated per well, and 10. Mu.L of standard curve (0,0.8125,1.625,3.25,6.5, 13 mM) per well was plated in 96-well plates. Detecting by using a Zhongsheng north glucose control detection kit (hexokinase method), adding R1, incubating at 37 ℃ for 5min, and reading absorbance at the wavelength of 340 nm. R2 was added to each well, and incubated at 37℃for 5min, and absorbance was read at 340 nm. The absolute glucose consumption was calculated from the standard curve, and the relative glucose consumption was calculated from the cell viability values, as shown in FIG. 1.
Experimental results
Hyperacmosin D significantly promoted glucose consumption in HepG2 cells, and the promotion was concentration dependent, similar to positive insulin, with significant statistical differences compared to the normal control group. Therefore, the Hyperacmosin D has a good hypoglycemic effect.
Conclusion of the experiment
The compound Hyperacmosin D has a good hypoglycemic effect, so that the Hyperacmosin D can be used for preparing antidiabetic medicines.
Claims (4)
1. A phloroglucinol compound having the chemical formula:
2. a process for the preparation of phloroglucinol according to claim 1, comprising the steps of:
extracting: extracting ground parts of hypericum (Hypericum acmosepaium N.Robson) with ethanol, and concentrating the extractive solution to obtain crude extract; dissolving the crude extract in water, uniformly suspending, extracting with petroleum ether, and concentrating the obtained extract to obtain petroleum ether extract;
separating: carrying out silica gel column chromatography on petroleum ether extract, and carrying out gradient elution for the first time by petroleum ether/ethyl acetate, wherein the volume ratio of petroleum ether/ethyl acetate is 1:0, further performing reduced pressure column chromatography by using a medium pressure chromatographic gel packing, eluting with 75% ethanol, 85% ethanol, 95% ethanol and acetone, eluting with two column volumes of each solvent, wherein each column volume is a component, and the total number of the components is A, B, C, D, E, F, G, H, further performing silica gel column chromatography by using 85% ethanol eluting component C, performing gradient elution with petroleum ether/ethyl acetate for the second time, eluting with two column volumes of each solvent, and sequentially performing gradient elution with petroleum ether/ethyl acetate at a concentration of volume ratio of 1:0,9:1,4:1,2:1,0:1, obtaining 20 components in total of C1-C20, wherein the volume ratio of petroleum ether to ethyl acetate is 9:1 elution part No. C6 prepared high performance liquid chromatography column with methanol/water volume ratio 95: eluting to obtain a compound Hyperacmosin D;
in the extraction step, the ethanol adopted is 95% ethanol; the extraction method is heating reflux extraction;
in the separation step, the gradient elution concentration of petroleum ether/ethyl acetate for the first time is sequentially as volume ratio of 1:0,9:1,2:1,0:1, a step of; the prepared high performance liquid chromatographic column filler is reverse phase octadecyl bonded silica gel.
3. A pharmaceutical composition comprising a phloroglucinol compound of claim 1 or a pharmaceutically acceptable salt thereof and an additional agent.
4. Use of a phloroglucinol compound of claim 1, or a pharmaceutically acceptable salt thereof, in the manufacture of an antidiabetic agent.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101264122A (en) * | 2007-03-16 | 2008-09-17 | 中国医学科学院药物研究所 | Hypericum extract, its making method and medicinal composition and use for treating diabetes |
| CN106916133A (en) * | 2017-01-18 | 2017-07-04 | 东北大学 | A kind of phloroglucin derivative with suppression PTP1B activity and preparation method thereof, application |
| CN109044999A (en) * | 2018-10-15 | 2018-12-21 | 上海市第六人民医院 | Hyperforine promotes white adipose milkproduct in preparation and improves the purposes in the active drug of brown fat |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101264122A (en) * | 2007-03-16 | 2008-09-17 | 中国医学科学院药物研究所 | Hypericum extract, its making method and medicinal composition and use for treating diabetes |
| CN106916133A (en) * | 2017-01-18 | 2017-07-04 | 东北大学 | A kind of phloroglucin derivative with suppression PTP1B activity and preparation method thereof, application |
| CN109044999A (en) * | 2018-10-15 | 2018-12-21 | 上海市第六人民医院 | Hyperforine promotes white adipose milkproduct in preparation and improves the purposes in the active drug of brown fat |
Non-Patent Citations (1)
| Title |
|---|
| 贯叶金丝桃的化学成分研究;时梦娇 等;《中国中药杂志》;20180731;第43卷(第13期);第2726-2731页 * |
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