CN110452110A - A kind of phloroglucinol derivatives natural drug and its preparation method and application - Google Patents
A kind of phloroglucinol derivatives natural drug and its preparation method and application Download PDFInfo
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- CN110452110A CN110452110A CN201810425488.0A CN201810425488A CN110452110A CN 110452110 A CN110452110 A CN 110452110A CN 201810425488 A CN201810425488 A CN 201810425488A CN 110452110 A CN110452110 A CN 110452110A
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
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- C—CHEMISTRY; METALLURGY
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- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/657—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings
- C07C49/683—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings having unsaturation outside the aromatic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/93—Spiro compounds
- C07C2603/95—Spiro compounds containing "not free" spiro atoms
- C07C2603/96—Spiro compounds containing "not free" spiro atoms containing at least one ring with less than six members
- C07C2603/97—Spiro compounds containing "not free" spiro atoms containing at least one ring with less than six members containing five-membered rings
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Abstract
The present invention relates to one kind to extract isolated phloroglucinol derivatives compound a syconone C, Its Preparation Method And Use for the first time from Chinese hyperici,herba (Hypericum ascyron L.).Biological activity test is shown: the compound has protection activity to hepatocellular injury caused by APAP, so that it can be used for preparing liver protection class drug.
Description
Technical field
The present invention relates to pharmaceutical technology fields.It is related to from Chinese hyperici,herba (Hypericum ascyron L.) aerial part
Extract isolated new phloroglucinol derivatives natural drug asyconone C with liver protective effect and preparation method thereof and
Application in Liver protection treatment
Background technique
Hyperici,herba is Guttiferae hypericum, and in addition to Qinghai, Xinjiang, all parts of the country are distributed.Hyperici,herba bitter,
It is cold in nature；Have the function of cooling blood and hemostasis, purging fire for removing toxin；For treating haematemesis, hemoptysis, bleeding, rheumatism, dysentery, hepatitis, irascibility head
Bitterly, jaundice and boil etc..
Summary of the invention
The technical problem to be solved by the present invention is to provide extract isolated phloroglucinol derivatives for the first time from hyperici,herba
Close object asyconone C, Its Preparation Method And Use.
To solve technical problem of the invention, the present invention provides the following technical scheme that
The first aspect of technical solution of the present invention there is provided phloroglucinol derivatives compound a syconone C,
There is provided the preparation sides of phloroglucinol derivatives compound a syconone C for the second aspect of technical solution of the present invention
Method, it is isolated from hyperici,herba aerial part, the specific steps are as follows:
It extracts: the hyperici,herba aerial part of crushing is extracted with ethyl alcohol, obtain coarse extract after the concentration of gained extracting solution；This is thick
Medicinal extract is dissolved in water, and petroleum ether extraction is used after being suspended uniformly, obtains petroleum ethereal extract after the concentration of gained extract liquor.
Separation: the petroleum ethereal extract is subjected to silica gel column chromatography, with petrol ether/ethyl acetate gradient elution, according to TLC
Colour developing merges similar fraction and obtains 12 component Fr.1~12；Wherein component Fr.1, that is, petrol ether/ethyl acetate volume ratio 1:0 is washed
De- part further progress silica gel column chromatography is merged similar with petroleum ether/chloroform volume ratio 4:1 isocratic elution according to TLC colour developing
Fraction obtains 5 components A, B, C, D, E, F.The further silica gel column chromatography of component F, with petrol ether/ethyl acetate gradient elution, stone
Oily ether/ethyl acetate volume ratio 9:1 elution fraction F5 obtains this hair through preparative HPLC with methanol/water volume ratio 95:5 elution
Bright compound a syconone C.
In the above preparation method, in extraction step, the ethyl alcohol used is 95% ethyl alcohol.
In the above preparation method, in extraction step, the method used of extracting is heating and refluxing extraction.
In the above preparation method, in separating step, the concentration of the gradient elution of first time petrol ether/ethyl acetate according to
Secondary is volume ratio 1:0,50:1,20:1,9:1,4:1,1:1.
In the above preparation method, in separating step, the concentration of the gradient elution of second of petrol ether/ethyl acetate according to
Secondary is volume ratio 1:0,9:1,4:1,2:1,0:1.
In the above preparation method, in separating step, the chromatographic column filler of the preparative HPLC is reverse phase octadecane
Base bonded silica gel.
There is provided a kind of pharmaceutical compositions for the third aspect of technical solution of the present invention, which is characterized in that the drug
Composition contains phloroglucinol derivatives compound and pharmaceutically acceptable salt or additives described in claim 1.
The pharmaceutical composition can be prepared according to method well known in the art.It can be by by the compounds of this invention and a kind of or more
The pharmaceutically acceptable solid of kind or liquid excipient and/or adjuvant combine, and any dosage form used suitable for human or animal is made.
Content of the compounds of this invention in its pharmaceutical composition is usually 0.1-95 weight %.
The compounds of this invention can be administered in a unit containing its pharmaceutical composition, and administration route can be enteron aisle
Or non-bowel, such as oral, intravenous injection, intramuscular injection, subcutaneous injection, nasal cavity, oral mucosa, eye, lung and respiratory tract, skin,
Vagina, rectum etc..
Form of administration can be liquid dosage form, solid dosage forms or semisolid dosage form.Liquid dosage form can be solution (including
True solution and colloidal solution), emulsion (including o/w type, w/o type and emulsion), suspension, injection (including liquid drugs injection, powder-injection
And infusion), eye drops, nasal drop, lotion and liniment etc.；Solid dosage forms can be tablet (including ordinary tablet, enteric coatel tablets, lozenge,
Dispersible tablet, chewable tablets, effervescent tablet, oral disnitegration tablet), capsule (including hard capsule, soft capsule, capsulae enterosolubilis), granule, dissipate
Agent, pellet, dripping pill, suppository, film, patch, the agent of gas (powder) mist, spray etc.；Semisolid dosage form can be ointment, gel
Agent, paste etc..
It is sustained release preparation, controlled release preparation, targeting preparation and various that the compounds of this invention, which can be made ordinary preparation, also be made,
Particulate delivery system.
In order to which tablet is made in the compounds of this invention, various excipient well known in the art can be widely used, including dilute
Release agent, binder, wetting agent, disintegrating agent, lubricant, cosolvent.Diluent can be starch, dextrin, sucrose, glucose, cream
Sugar, mannitol, sorbierite, xylitol, microcrystalline cellulose, calcium sulfate, calcium monohydrogen phosphate, calcium carbonate etc.；Wetting agent can be water, second
Alcohol, isopropanol etc.；Adhesive can be starch slurry, dextrin, syrup, honey, glucose solution, microcrystalline cellulose, Arabic gum
Slurry, gelatine size, sodium carboxymethylcellulose, methylcellulose, hydroxypropyl methyl cellulose, ethyl cellulose, acrylic resin, card
Wave nurse, polyvinylpyrrolidone, polyethylene glycol etc.；Disintegrating agent can be dried starch, microcrystalline cellulose, low substituted hydroxy-propyl fiber
Element, crosslinked polyvinylpyrrolidone, croscarmellose sodium, sodium carboxymethyl starch, sodium bicarbonate and citric acid, polyoxy second
Alkene sorbitan fatty acid ester, dodecyl sodium sulfate etc.；Lubricant and cosolvent can be talcum powder, silica, tristearin
Hydrochlorate, tartaric acid, atoleine, polyethylene glycol etc..
Tablet can also be further made to coating tablet, such as sugar coated tablet, thin membrane coated tablet, enteric coated tablets or double
Synusia and multilayer tablet.
In order to which capsule is made in administration unit, effective component the compounds of this invention and diluent, cosolvent can be mixed
It closes, mixture is placed directly in hard capsule or soft capsule.It can also effective component the compounds of this invention is first and diluent, bonding
Particle or pellet is made in agent, disintegrating agent, then is placed in hard capsule or soft capsule.It is used to prepare each dilute of the compounds of this invention tablet
Release agent, binder, wetting agent, disintegrating agent, cosolvent kind can also be used for preparing the capsule of the compounds of this invention.
For injection is made in the compounds of this invention, water, ethyl alcohol, isopropanol, propylene glycol or their mixture can be used
Make solvent and appropriate solubilizer commonly used in the art, cosolvent, pH adjusting agent, osmotic pressure regulator is added.Solubilizer or hydrotropy
Agent can be poloxamer, lecithin, hydroxypropyl-β-cyclodextrin etc.；PH adjusting agent can be phosphate, acetate, hydrochloric acid, hydrogen
Sodium oxide molybdena etc.；Osmotic pressure regulator can be sodium chloride, mannitol, glucose, phosphate, acetate etc..Such as prepare freeze-dried powder
Mannitol, glucose etc. can be also added as proppant in injection.
In addition, if desired, colorant, preservative, fragrance, corrigent or other additions can also be added into pharmaceutical preparation
Agent.
To reach medication purpose, enhance therapeutic effect, drug of the invention or pharmaceutical composition well known can be given with any
The administration of prescription method.
The dosage of the compounds of this invention pharmaceutical composition is according to the property and serious journey to be prevented or be treated disease
The individual instances of degree, patient or animal, administration route and dosage form etc. can have large-scale variation.In general, of the present inventionization
The daily Suitable dosage ranges for closing object are 0.001-5mg/Kg weight.Above-mentioned dosage with a dosage unit or can be divided into several
Dosage unit administration, this depends on the clinical experience of doctor and includes the dosage regimen with other treatment means.
The compound of the present invention or composition can individually be taken, or merge use with other treatment drug or symptomatic drugs.
When the compound of the present invention and other therapeutic agents, which exist, to act synergistically, its dosage should be adjusted according to the actual situation.
There is provided phloroglucinol derivatives compound a syconone C in preparation liver protection for the fourth aspect of technical solution of the present invention
Purposes in class drug.
Advantageous effects
The present invention tests the protection activity for the HepG2 cell that asyconone C damages paracetamol using mtt assay.
Experiment confirms that asyconone C has apparent protection activity to the liver cell of damage caused by above-mentioned APAP.Therefore, of the invention
Asyconone C can be used as prepare liver protection class drug.
Specific embodiment
(Arabic numerals in structural formula are the chemical structural formula of signified asyconone C in the following example
The mark of carbon atom in chemical structure):
The preparation of asyconone C described in embodiment 1
It extracts: by dry hyperici,herba aerial part 75.0kg, with 95% ethyl alcohol heating and refluxing extraction 3 times after crushing, institute
It obtains after extracting solution is concentrated under reduced pressure and obtains coarse extract；The coarse extract is dissolved in water, after being suspended uniformly three times with petroleum ether extraction, gained extraction
Petroleum ethereal extract is obtained after taking liquid to be concentrated under reduced pressure.
Separation: petroleum ethereal extract carry out silica gel column chromatography by the petroleum ethereal extract carry out silica gel column chromatography, with petroleum ether/
Ethyl acetate gradient merges similar fraction according to TLC colour developing and obtains 12 component Fr.1~12；Wherein component Fr.1, that is, stone
Oily ether/ethyl acetate volume ratio 1:0 elution fraction further progress silica gel column chromatography, with petroleum ether/chloroform 4:1 isocratic elution,
Merge similar fraction according to TLC colour developing and obtains 5 components A, B, C, D, E, F.The further silica gel column chromatography of component F, with petroleum ether/
Ethyl acetate gradient, petrol ether/ethyl acetate volume ratio 9:1 elution fraction, that is, component F5 is through preparative HPLC [C18 column
(10 μm, 250 × 20mm) methanol/water 95:5 volume ratio elutes, and detects under flow velocity 6mL/min, 254nm wavelength], obtain the present invention
Compound a syconone C (5mg).
Structural Identification: routinely through the various moderns spectral technique such as NMR, HRESIMS, UV, IR and optically-active, it is determined that chemical combination
The chemical structure of object asyconone C, physicochemical property are as follows:
Colorless oil, molecular formula C26H34O2,[α]20D+76.9(c 0.05,MeOH)；
Ultraviolet spectra UV (MeOH) λmax258 (4.12) (log ε), 292 (3.31) nm；
Infrared spectroscopy IR (KBr) νmax: 1704,1666,1598,1450；
High resolution mass spectrum HRESIMS m/z 379.2637 [M+H]+(calculated for C26H35O2,379.2637)；
Nuclear magnetic resonance spectroscopy1H NMR (500MHz) and carbon-13 nmr spectra13C NMR (125MHz) data are shown in Table one,
Asyconone C described in table one1H 13C and NMR (ppm in CDCl3)
Embodiment 2asyconone C causes hepatocellular injury protection activity to be tested external APAP.
Laboratory sample
The configuration of sample solution: test sample is the sterling compound (asyconone C) prepared in embodiment 1.
Appropriate amount of sample is accurately weighed, the solution of 10mM/mL is configured to using DMSO, is tested for pharmacological activity.
Cell strain: human hepatoma HepG2 cell.Containing 10% fetal calf serum DMEM culture solution (100U/ml containing penicillin,
100 μ g/ml of streptomysin) in growth, condition of culture be 37 DEG C, 5%CO2, saturated humidity.With containing 0.25% trypsase and
0.02%EDTA liquid had digestive transfer culture.
Experimental method
Using MTT method.After culture for 24 hours, non-toxic concn is added in 96 porocyte culture plates in HepG2 cell inoculation
Untested compound and paracetamol (APAP, final concentration 8mM), while setting positive drug control group (bicyclic alcohols, bicyclol), molten
Agent blank control group and model group.Continue function cells 48h.Culture solution is discarded, 100 μ l of MTT (0.5mg/ml) liquid is added in every hole,
Continue to cultivate 4h, discard MTT liquid, 150 μ l of DMSO is added in every hole, mixes oscillator oscillation, surveys at microplate reader 570nm wavelength
Determine absorbance value.
Cell survival rate (%)=(administration group OD average value/solvent control group OD average value) × 100%.
Experimental result
APAP 8mM acts on HepG2 cell 48h, generates significant damage, cell survival rate 20.96% to HepG2 cell.
Under current experimental program, asyconone C is shared in 10 μM of concentration with APAP, equal to HepG2 cellular damage caused by the latter
There is significant protective effect (cell survival rate 31.58%), there is statistical difference compared with model group.
Experiment conclusion
Compound a syconone C causes hepatocellular injury to have preferable protective effect, therefore, this hair external APAP
Bright asyconone C can be used for preparing in the drug of liver protection.
Claims (9)
1. the following phloroglucinol derivatives compound of a kind of chemical structural formula:
2. the preparation method of phloroglucinol derivatives compound described in claim 1, which is characterized in that this method includes following step
It is rapid:
It extracts: the hyperici,herba aerial part of crushing is extracted with ethyl alcohol, obtain coarse extract after the concentration of gained extracting solution；By the coarse extract
It is dissolved in water, petroleum ether extraction is used after being suspended uniformly, obtains petroleum ethereal extract after the concentration of gained extract liquor；
Separation: petroleum ethereal extract carries out silica gel column chromatography, with petrol ether/ethyl acetate gradient elution, wherein petroleum ether/acetic acid
The elution fraction further progress silica gel column chromatography of ethyl ester volume ratio 1:0, with petroleum ether/chloroform volume ratio 4:1 elution, eluent
Further progress silica gel column chromatography, with petrol ether/ethyl acetate gradient elution, wherein petrol ether/ethyl acetate volume ratio 9:1
Elution fraction obtains phloroglucinol derivatives compound through preparative HPLC with methanol/water volume ratio 95:5 elution.
3. preparation method according to claim 2, which is characterized in that in extraction step, the ethyl alcohol used is 95% ethyl alcohol.
4. preparation method according to claim 2, which is characterized in that in extraction step, it is described extract the method that uses for
Heating and refluxing extraction.
5. preparation method according to claim 2, which is characterized in that in separating step, first time petrol ether/ethyl acetate
The concentration of gradient elution be followed successively by volume ratio 1:0,50:1,20:1,9:1,4:1,1:1.
6. preparation method according to claim 2, which is characterized in that in separating step, second of petrol ether/ethyl acetate
The concentration of gradient elution be followed successively by volume ratio 1:0,9:1,4:1,2:1,0:1.
7. preparation method according to claim 2, characterized in that in separating step, the chromatography of the preparative HPLC
Column packing is reverse phase octadecyl silane.
8. a kind of pharmaceutical composition, which is characterized in that the pharmaceutical composition contains phloroglucinol derivatives described in claim 1
Compound and pharmaceutically acceptable salt or additives.
9. phloroglucinol derivatives compound described in claim 1 is preparing the purposes in hepatic.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113444062A (en) * | 2020-03-27 | 2021-09-28 | 中国医学科学院药物研究所 | Phlebendrin F as phloroglucinol compound and application thereof in resisting liver injury |
| CN115181024A (en) * | 2021-04-07 | 2022-10-14 | 中国医学科学院药物研究所 | Phloroglucinol compound and application thereof in resisting liver injury |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113444062A (en) * | 2020-03-27 | 2021-09-28 | 中国医学科学院药物研究所 | Phlebendrin F as phloroglucinol compound and application thereof in resisting liver injury |
| CN115181024A (en) * | 2021-04-07 | 2022-10-14 | 中国医学科学院药物研究所 | Phloroglucinol compound and application thereof in resisting liver injury |
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