CN111943920A - Pheracimin D as phloroglucinol compound and application thereof in preparation of antidiabetic drugs - Google Patents
Pheracimin D as phloroglucinol compound and application thereof in preparation of antidiabetic drugs Download PDFInfo
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- CN111943920A CN111943920A CN201910401940.4A CN201910401940A CN111943920A CN 111943920 A CN111943920 A CN 111943920A CN 201910401940 A CN201910401940 A CN 201910401940A CN 111943920 A CN111943920 A CN 111943920A
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- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
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Abstract
The invention relates to a phloroglucinol compound Hyperacmosin D extracted and separated from Hypericum aceseparium N.Robson for the first time, a preparation method and application thereof. The biological activity test shows that: the compound Hyperacmosin D has good blood sugar reducing 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 the overground part of Hypericum acesepatum N.Robson, a preparation method thereof and application thereof in anti-diabetic active treatment.
Background
The hypericum perforatum is a plant of hypericum genus of gamboge family, which is also called as: a fragrant needle tree. Is distributed in Guangxi, Sichuan, Guizhou, Yunnan and other places in China. Is used for diminishing inflammation and swelling, treating hepatitis and the like in folk. The chemical components of the traditional Chinese medicine are rarely researched at present and are not used as the traditional Chinese medicine in the common prescription. However, a great deal of literature reports that phloroglucinol compounds have a series of good pharmacological activities such as antivirus and anti-inflammation, and hypericum cuspidatum is rich in rich phloroglucinol components, so that further research and explanation on chemical components and potential effects of phloroglucinol compounds are very meaningful.
Disclosure of Invention
The invention aims to provide a phloroglucinol compound Hyperacmosin D extracted and separated from hypericum acutum for the first time, a pharmaceutically acceptable salt thereof, a preparation method and application thereof.
In order to solve the technical problem, the invention provides the following technical scheme:
the first aspect of the technical scheme of the invention is to provide a phloroglucinol compound Hyperacmosin D and pharmaceutically acceptable salts thereof, wherein the structure of the compound is as follows:
the second aspect of the technical scheme of the invention provides a preparation method of phloroglucinol compound Hyperacmosin D, which is obtained by separating from the overground part of hypericum acutangula and comprises the following specific steps:
extraction: extracting the ground overground part of the hypericum perforatum with ethanol, and concentrating the obtained extracting solution to obtain a crude extract; dissolving the crude extract in water, suspending uniformly, extracting with petroleum ether, and concentrating the obtained extract to obtain petroleum ether extract.
Separation: performing silica gel column chromatography on the petroleum ether extract, and performing gradient elution by using petroleum ether/ethyl acetate for the first time, wherein the volume ratio of the petroleum ether to the ethyl acetate is 1: and (3) performing reduced pressure column chromatography on the elution part of 0 by using a medium-pressure chromatographic gel filler, eluting with 75% ethanol, 85% ethanol, 95% ethanol and acetone, eluting each solvent by using two column volumes, wherein each column volume is one component to obtain eight components with the number of A, B, C, D, E, F, G, H, performing silica gel column chromatography on the 85% ethanol elution component C, performing gradient elution on petroleum ether/ethyl acetate for the second time, eluting each solvent by using two column volumes, and sequentially performing volume ratio of gradient elution concentration of the petroleum ether/ethyl acetate to 1: 0,9: 1,4: 1,2: 1,0: 1, obtaining 20 components of C1-C20, wherein the volume ratio of petroleum ether/ethyl acetate is 9: 1 elution fraction No. C6 was purified by preparative hplc on a methanol/water volume ratio of 95: and 5, eluting to obtain the compound Hyperacmosin D.
In the above preparation method, in the extraction step, the ethanol used is 95% ethanol.
In the above preparation method, in the extraction step, the extraction is performed by heating reflux extraction.
In the preparation method, in the separation step, the concentration of the first petroleum ether/ethyl acetate gradient elution is sequentially 1: 0,9: 1,2: 1,0: 1.
in the preparation method, in the separation step, the concentration of the second petroleum ether/ethyl acetate gradient elution is 1: 0,9: 1,4: 1,2: 1,0: 1.
in the above preparation method, in the separation step, the chromatographic column packing of the preparative HPLC is reverse-phase octadecyl bonded silica gel.
In a third aspect of the present invention, there is provided a pharmaceutical composition, wherein the pharmaceutical composition contains the phloroglucinol compound according to claim 1, and pharmaceutically acceptable salts or additives, and the use of the phloroglucinol compound according to claim 1 and pharmaceutically acceptable salts thereof in antidiabetic drugs.
The pharmaceutical composition may be prepared according to methods well known in the art. The compounds of the invention may be formulated into any dosage form suitable for human or animal use by combining them with one or more pharmaceutically acceptable solid or liquid excipients and/or adjuvants. The compounds of the present invention are generally present in the pharmaceutical compositions in an amount of from 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 enteral or parenteral routes, such as oral, intravenous, intramuscular, subcutaneous, nasal, oromucosal, ophthalmic, pulmonary and respiratory, dermal, vaginal, rectal, and the like.
The dosage form for administration may be a liquid dosage form, a solid dosage form, or a semi-solid dosage form. The liquid dosage forms can be solution (including true solution and colloidal solution), emulsion (including o/w type, w/o type and multiple emulsion), suspension, injection (including water injection, powder injection and infusion), eye drop, nose drop, lotion, liniment, etc.; the solid dosage form can be tablet (including common tablet, enteric coated tablet, buccal tablet, dispersible tablet, chewable tablet, effervescent tablet, orally disintegrating tablet), capsule (including hard capsule, soft capsule, and enteric coated capsule), granule, powder, pellet, dripping pill, suppository, pellicle, patch, aerosol (powder), spray, etc.; semisolid dosage forms can be ointments, gels, pastes, and the like.
The compound can be prepared into common preparations, sustained release preparations, controlled release preparations, targeting preparations and various particle drug delivery systems.
For tableting the compound of the present invention, a wide variety of excipients known in the art may be used, including diluents, binders, wetting agents, disintegrants, lubricants, and solubilizers. The diluent can be starch, dextrin, sucrose, glucose, lactose, mannitol, sorbitol, xylitol, microcrystalline cellulose, calcium sulfate, calcium hydrogen phosphate, calcium carbonate, etc.; the humectant can be water, ethanol, isopropanol, etc.; the binder can be starch slurry, dextrin, syrup, Mel, glucose solution, microcrystalline cellulose, acacia slurry, gelatin slurry, sodium carboxymethylcellulose, methylcellulose, hydroxypropyl methylcellulose, ethyl cellulose, acrylic resin, carbomer, polyvinylpyrrolidone, polyethylene glycol, etc.; the disintegrant may be dry starch, microcrystalline cellulose, low-substituted hydroxypropyl cellulose, crosslinked polyvinylpyrrolidone, crosslinked sodium carboxymethylcellulose, sodium carboxymethyl starch, sodium bicarbonate and citric acid, polyoxyethylene sorbitol fatty acid ester, sodium dodecyl sulfate, etc.; the lubricant and cosolvent may be talc, silica, 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 double-layer and multi-layer tablets.
To encapsulate the administration unit, the active ingredient of the compound of the present invention may be mixed with a diluent and a cosolvent, and the mixture may be directly placed in a hard capsule or soft capsule. Or the effective component of the compound of the invention can be prepared into granules or pellets with diluent, adhesive and disintegrating agent, and then placed into hard capsules or soft capsules. The diluents, binders, wetting agents, disintegrants, and cosolvents used to prepare the compound tablets of the present invention can also be used to prepare capsules of the compounds of the present invention.
For preparing the compound of the present invention into injection, water, ethanol, isopropanol, propylene glycol or their mixture can be used as solvent, and appropriate amount of solubilizer, cosolvent, pH regulator, and osmotic pressure regulator commonly used in the art can 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 and glucose can be added as proppant for preparing lyophilized powder for injection.
In addition, colorants, preservatives, flavors, or other additives may also be added to the pharmaceutical preparation, if desired.
For the purpose of administration and enhancing the therapeutic effect, the drug or pharmaceutical composition of the present invention can be administered by any known administration method.
The dosage of the pharmaceutical composition of the compound of the present invention to be administered 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 and dosage form of administration, and the like. Generally, a suitable daily dosage range for a compound of the invention is 0.001-5mg/Kg body weight. The above-described dosage may be administered in one dosage unit or divided into several dosage units, depending on the clinical experience of the physician and the dosage regimen including the use 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 is used in a synergistic manner with other therapeutic agents, the dosage thereof should be adjusted according to the actual circumstances.
The fourth aspect of the technical scheme of the invention provides application of a compound Hyperacmosin D and pharmaceutically acceptable salts thereof in preparing antidiabetic drugs.
Advantageous technical effects
The invention adopts a method for evaluating the protection effect of a monomeric compound on glucose consumption experiments and in vitro APAP-induced liver cell injury. Experiments prove that the compound Hyperacmosin D has better blood sugar reducing effect and can be used for preparing antidiabetic medicaments.
Drawings
FIG. 1: effect of Hyperacmosin D on glucose consumption by HepG2 cells. Veh: normal control; ins: insulin.
Detailed Description
The chemical structural formula of Hyperacmosin D (the arabic number in the structural formula is the index position of a carbon atom in the chemical structure) referred to in the examples is as follows:
example 1 preparation of Hyperacmosin D
Extraction: pulverizing 17.0kg aerial part of Hypericum perforatum (Hypericum acmosepatum N.Robson), extracting with 95% ethanol under reflux for 3 times, and concentrating the extractive solution under reduced pressure 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.
Separation: performing silica gel column chromatography on the petroleum ether extract, performing gradient elution by using petroleum ether/ethyl acetate,
the concentration of petroleum ether/ethyl acetate gradient elution is 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 component Fr.1 is petroleum ether/ethyl acetate volume ratio of 1: performing MCI reduced pressure column chromatography on the eluted part 0, eluting with 75%, 85%, 95% ethanol and acetone,
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 and gradient elution by petroleum ether/ethyl acetate,
petroleum ether/ethyl acetate volume ratio 1: 0,9: 1,4: 1,2: 1,0: 1.
color development according to TLC anisaldehyde combined similar fractions yielded 20 fractions with a petroleum ether/ethyl acetate volume ratio of 9: 1 fraction eluted, component C6.
By preparative HPLC [ C ]18Column (5 μm, 250 × 10mm) methanol/water 95: 5 volume ratio elution, flow rate of 3mL/min, detection at 254nm wavelength, to obtain the compound Hyperacmosin D (12mg) of the invention.
And (3) structural identification: the chemical structure of the compound Hyperacmosin D is determined by various modern spectral techniques such as NMR, HRESIMS, UV, IR, optical rotation and the like, and the physicochemical properties are as follows:
Hyperacmosin D：
colorless oil, molecular formula C37H58O6；
Ultraviolet spectrum UV (MeOH) lambdamax(log)204(3.84)nm；
Infrared Spectrum IR (KBr) vmax；3397,2969,2925,1758,1715,1448,1380cm-1；
Circular dichroism chromatography ECD (MeOH) lambdamax(Δ)312.5(-2.76)nm；
High resolution mass spectrum HRESIMS M/z 621.41256[ M + Na ]]+(calculated for C37H58O6,621.41168)；
Nuclear magnetic resonance hydrogen spectrum of Hyperacmosin D1H NMR (500MHz) and NMR carbon Spectroscopy13C NMR (125MHz) data are shown in Table 1.
Of Hyperacmosin D described in Table 11H and13C NMR(ppm in CDCl3)
experimental example 1 Effect of Hyperacmosin D on cellular glucose consumption
Experimental sample
Preparation of a tested sample solution: the test sample was the pure compound prepared in example 1 (Hyperacmosin D). An appropriate amount of sample was accurately weighed and prepared into 0.1M stock solution using DMSO for pharmacological activity testing.
Cell lines: human liver cancer HepG2 cells. Growth in DMEM medium (containing penicillin 100U/ml and streptomycin 100. mu.g/ml) containing 10% fetal bovine serum at 37 deg.C and 5% CO2And saturation humidity. The passage was digested with a solution containing 0.25% trypsin and 0.02% EDTA.
Experimental methods
HepG2 cells were inoculated in 96-well cell culture plates, and after 24h of culture, the next day low-sugar medium was changed and dosed, while positive drug control group (insulin ), solvent blank control group and model group were set, with insulin concentration of 0.03. mu.M, and drug action concentrations of 0.1. mu.M and 1. mu.M. After 24h incubation, supernatants were removed for glucose consumption and cell viability was determined by adding CCK8, 10. mu.L of supernatant medium was aspirated into each well and 10. mu.L of standard (0, 0.8125, 1.625, 3.25, 6.5, 13mM) was pipetted into 96-well plates. Detecting with Zhongsheng Bei glucose control detection kit (hexokinase method), adding R1, incubating at 37 deg.C for 5min, and reading absorbance value at wavelength of 340 nm. R2 was added to each well, and the wells were incubated at 37 ℃ for 5min, and absorbance was read at a wavelength of 340 nm. The absolute glucose consumption was calculated from the standard curve and the relative glucose consumption was calculated from the cell viability values, the results are shown in FIG. 1.
Results of the experiment
The Hyperacmosin D obviously promotes the consumption of glucose in HepG2 cells, the promoting effect of the Hyperacmosin D is concentration-dependent, and the Hyperacmosin D is similar to the positive drug insulin and has obvious statistical difference compared with a normal control group. Therefore, the Hyperacmosin D has better hypoglycemic effect.
Conclusion of the experiment
The compound Hyperacmosin D has better blood sugar reducing effect, so the compound Hyperacmosin D can be used for preparing antidiabetic medicaments.
Claims (8)
1. A phloroglucinol compound with the chemical structural formula as shown in the specification and pharmaceutically acceptable salts thereof:
2. the method of claim 1, comprising the steps of:
extraction: extracting aerial parts of pulverized Hypericum perforatum (Hypericum acmosepatum N.Robson) with ethanol, and concentrating the obtained extractive 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;
separation: performing silica gel column chromatography on the petroleum ether extract, and performing gradient elution by using petroleum ether/ethyl acetate for the first time, wherein the volume ratio of the petroleum ether to the ethyl acetate is 1: and (3) performing reduced pressure column chromatography on the elution part of 0 by using a medium-pressure chromatographic gel filler, eluting with 75% ethanol, 85% ethanol, 95% ethanol and acetone, eluting each solvent by using two column volumes, wherein each column volume is one component to obtain eight components with the number of A, B, C, D, E, F, G, H, performing silica gel column chromatography on the 85% ethanol elution component C, performing gradient elution on petroleum ether/ethyl acetate for the second time, eluting each solvent by using two column volumes, and sequentially performing volume ratio of gradient elution concentration of the petroleum ether/ethyl acetate to 1: 0,9: 1,4: 1,2: 1,0: 1, obtaining 20 components of C1-C20, wherein the volume ratio of petroleum ether/ethyl acetate is 9: 1 elution fraction No. C6 was purified by preparative hplc on a methanol/water volume ratio of 95: and 5, eluting to obtain the compound Hyperacmosin D.
3. The method of claim 2, wherein the ethanol used in the extracting step is 95% ethanol.
4. The method according to claim 2, wherein the extraction step is carried out by heating and refluxing.
5. The method according to claim 2, wherein in the separation step, the concentration of the first petroleum ether/ethyl acetate gradient elution is in the order of volume ratio of 1: 0,9: 1,2: 1,0: 1.
6. the method according to claim 2, wherein the preparative high performance liquid chromatography column packing material in the separation step is reverse-phase octadecyl bonded silica gel.
7. A pharmaceutical composition comprising the phloroglucinol compound of claim 1, and a pharmaceutically acceptable salt or additive.
8. Use of phloroglucinol compounds according to claim 1 and pharmaceutically acceptable salts thereof for the preparation of a medicament for treating diabetes.
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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 |
|---|
| 时梦娇 等: "贯叶金丝桃的化学成分研究", 《中国中药杂志》 * |
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