CN109096238A - A kind of flavone compound and preparation method and medical application - Google Patents
A kind of flavone compound and preparation method and medical application Download PDFInfo
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- CN109096238A CN109096238A CN201810953058.6A CN201810953058A CN109096238A CN 109096238 A CN109096238 A CN 109096238A CN 201810953058 A CN201810953058 A CN 201810953058A CN 109096238 A CN109096238 A CN 109096238A
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- flavone compound
- celery
- ethyl alcohol
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
- C07D311/64—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with oxygen atoms directly attached in position 8
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/06—Antigout agents, e.g. antihyperuricemic or uricosuric agents
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids
Abstract
The present invention provides a kind of flavone compound and preparation method and medical applications, provide a kind of new compound, inhibiting hyperuricemia drug and acute gouty arthritis drug can be prepared, toxicology data, which is shown, to have no toxic side effect, as antipodagric new drug development is prevented, tool has great advantage and good prospect；The present invention also provides the preparation methods of the compound, and using celery seed as raw material, extraction efficiency is high, extract at low cost, good perfection easy to operate.
Description
Technical field
The present invention provides a kind of flavone compounds, while additionally providing the preparation method of compound, further open
The medical application of the compound belongs to medicine pharmaceutical technology field.
Background technique
Gout is the metabolic disease as caused by hyperuricemia, and the following uric acid crystal is deposited in joint and tissue
In.Gout is the crystal correlation arthropathy caused by monosodium urate salt (MSU) deposition, with purine metabolic disturbance and uric acid excretion
Hyperuricemia caused by reducing is directly related, refers in particular to acute gouty arthritis and chronic gouty calculus disease, main to wrap
Acute attack arthritis, tophus formation, tophaceous chornic arthritis, urate nephropathy and uric acid lithangiuria are included,
Severe one may occur in which joint deformity and renal insufficiency.The disease incidence and popularity degree of gout are increasing always in decades.Single sodium
Urate crystals can cause inflammatory reaction in joint and tissue, therefore the purpose of gout clinical treatment is to reduce uric acid level simultaneously
Cure inflammation.Hyperuricemia is one of current most common metabolic disease.High lithemia level in blood causes joint and kidney
Crystallization in dirty, and it is well-known gout, the major risk factors of cardiovascular disease and diabetes.
Uric acid excretion disorder caused by hyperuricemia is mainly increased by uric acid level or multi-mechanism.Currently on the market
There is the drug of relevant treatment hyperuricemia and gout.Wherein, the drug for controlling urarthritis symptom mainly wraps
Include colchicin, non-steroid anti-inflammatory drug and glucocorticoid etc.；Inhibiting hyperuricemia class drug mainly includes inhibiting uric acid raw
Patent medicine (such as Allopurinol) and promotion uric acid discharge medicine (such as Benzbromarone and probenecid).But there is side effect that can especially add
The burden of weight people's liver and kidney.Therefore, seek preferably harmless drug will certainly become future therapeutic gout with
The trend of hyperuricemia.
Celery is the umbellate form flower biennial herbaceous plant of section.Seashore in source area, there are about 20 kinds, with being distributed in whole world temperate zone
Area.Celery seed be celery seed, be commonly applied in flavouring and food, its vitamin and volatile aromatic rich at
Point, there is fabulous medical value.Celery seed tea has obvious action to blood pressure lowering, norcholesterol, promotion sleep.Traditional Chinese Medicine is recognized
There is air-dispersing for celery seed, reduce swelling, diuresis, reduce blood pressure and other effects.It is mainly used for treating hypertension, reducing blood lipid, anti-oxidant, anti-
Helicobacter pylori, treatment gastric ulcer, enteritis, bronchitis etc. is as a kind of diuretics for effectively treating cystitis and nephrosis
Clinically apply.
Summary of the invention
The present invention provides a kind of flavone compound, have in terms of inhibiting hyperuricemia and antigout preferable prevention and
Therapeutic effect.
The invention also discloses a kind of preparation method of flavone compound, celery oil is extracted from celery seed, then from
Celery oil extracts flavone compound.
A kind of flavone compound of the present invention, title are as follows: 2-(2,4- dihydroxy -5- methoxyphenyl) -5,7-
Dihydroxy -4H- chromene -4- ketone, has following structure formula:
(structural formula 1)
Molecular formula are as follows: C1507H12；Molecular weight are as follows: 304.241.
A kind of preparation method of the above-mentioned flavone compound of the present invention, comprising the following steps:
1) by 5~10s of celery seed crushed after being dried；
2) smashed celery seed is extracted with supercritical carbon dioxide extraction equipment: extracting pressure 25Mpa, temperature 30
℃；Separating pressure 8Mpa, 32 DEG C of temperature: each extraction time is 2 hours and every 15 minutes collection celery oil；
3) celery oil and the ethyl alcohol of volume fraction 70% carry out being mixed and heated to 80 DEG C of refluxing extractions twice according to the ratio of 1:5,
Combined extract recycles ethyl alcohol, and extracting solution volatilizes under 80 DEG C of water bath conditions, carries out vacuum freeze drying later and obtains celery oil
Flavones；
4) the celery oil flavones extracted first is purified to obtain Primary purification part with macroreticular resin XAD-16 pillar.It uses later
Polyamide column is further purified and is dried in vacuo, and obtaining purification part is flavone compound.
A kind of medical application of the flavone compound of the present invention in preparation inhibiting hyperuricemia drug.
A kind of flavone compound of the present invention is preparing the medical application in acute gouty arthritis drug.
The flavone compound that purifying is obtained carries out the animal model experiment of inhibiting hyperuricemia, observes Flavonoid substances
To hyperuricemia therapeutic effect.Experiment shows that the flavone compound being prepared can be substantially reduced hyperuricemia mouse
Serum uric acid level, anti-trioxypurine effect are related with the activity of xanthine oxidase is inhibited.Illustrate the flavonoids being prepared
Close object has preferable preventive and therapeutic action in terms of inhibiting hyperuricemia and antigout.
The positive effect of the present invention is: providing a kind of new compound, can prepare inhibiting hyperuricemia drug and acute
Urarthritis drug, toxicology data, which is shown, to have no toxic side effect, as preventing that antipodagric new drug development, tool have great advantage
And good prospect；The present invention also provides the preparation methods of the compound, and using celery seed as raw material, extraction efficiency is high, extraction at
This low, good perfection easy to operate.
Detailed description of the invention:
Fig. 1 is the influence of arthroncus of the present invention to rat.
Specific embodiment:
The following are specific embodiments of the present invention, it will be appreciated by those of skill in the art that this is merely illustrative, this
The protection scope of invention is defined by the appended claims, those skilled in the art without departing substantially from the principle of the present invention and
Under the premise of essence, many changes and modifications may be made, these change and modification each fall within the present invention
Protection scope.
Embodiment 1:
The preparation of celery oil: weighing celery seed 500g, is crushed celery seed with pulverizer；Weigh smashed celery seed
300g is extracted with supercritical carbon dioxide extraction equipment, extraction kettle pressure 25Mpa, and 32 DEG C of temperature；I pressure 8Mpa is separated,
35 DEG C of temperature；Separate II pressure 6Mpa, 35 DEG C of temperature；It is extracted after temperature and pressure reaches setting value: every time when extraction
Between 2 hours and to collect celery oil from separating still every 15 minutes；The purifying work of Flavonoid substances in celery celery oil
Skill are as follows: ethyl alcohol is extracted twice → combining extraction liquid → recycling ethyl alcohol and → vacuum freeze drying → celery oil flavones is concentrated.It will
The celery oil flavones extracted loads macroreticular resin XAD-16 pillar, and after being activated well, wet process loading crude extract is successively used
Water, 10% ethyl alcohol, 20% ethanol elution, 30% ethyl alcohol, 50% ethyl alcohol, 70% ethyl alcohol, 95% ethanol elution is complete, collects each eluent,
Rotary evaporation recycles ethyl alcohol, and concentrate is in 80 DEG C.It is volatilized in water-bath, is dried in vacuo, obtains Primary purification part.Load polyamides
Amine column takes the Primary purification part of 30% ethyl alcohol, 50% ethanol eluate, mixes polyamide column on sample after processing, successively use water, 30%
Ethanol elution collects 30% eluent, rotary evaporation, and concentrate is volatilized in 80 DEG C of water-baths, is dried in vacuo, obtains purification part
As flavone compound (referring to structural formula 1).
Embodiment 2:
The preparation of celery oil: weighing celery seed 300g, is crushed celery seed with pulverizer；Weigh smashed celery seed
200g is extracted with supercritical carbon dioxide extraction equipment, extracting pressure 25Mpa, and 35 DEG C of temperature；I pressure 10Mpa is separated,
35 DEG C of temperature；Separate II pressure 8Mpa, 35 DEG C of temperature.It is extracted after temperature and pressure reaches setting value；Extraction every time
Time is 2 hours and collected celery oil from separating still every 15 minutes；The purifying of Flavonoid substances in celery celery oil
Technique are as follows: ethyl alcohol is extracted twice → combining extraction liquid → recycling ethyl alcohol and → vacuum freeze drying → celery oil flavones is concentrated；
The celery oil flavones extracted is loaded into macroreticular resin XAD-16 pillar, after being activated well, wet process loading crude extract, successively
With water, 10% ethyl alcohol, 20% ethanol elution, 30% ethyl alcohol, 50% ethyl alcohol, 70% ethyl alcohol, 95% ethanol elution is complete, collects each elution
Liquid, rotary evaporation recycle ethyl alcohol, and concentrate is in 80 DEG C.It is volatilized in water-bath, is dried in vacuo, obtains Primary purification part.It loads poly-
Amide column takes the Primary purification part of 30% ethyl alcohol, 50% ethanol eluate, mixes polyamide column on sample after processing, successively use water,
30% ethanol elution collects 30% eluent, rotary evaporation, and concentrate is volatilized in 80 DEG C of water-baths, is dried in vacuo, obtains purifying portion
Divide is flavone compound (referring to structural formula 1).
Embodiment 3:
The preparation of celery oil: weighing celery seed 200g, is crushed celery seed with pulverizer；Weigh smashed celery seed
100g is extracted with supercritical carbon dioxide extraction equipment, extracting pressure 25Mpa, and 30 DEG C of temperature；I pressure 8Mpa is separated, temperature
35 DEG C of degree；Separate II pressure 6Mpa, 35 DEG C of temperature.It is extracted after temperature and pressure reaches setting value.Each extraction time
Celery oil is collected from separating still for 2 hours and every 15 minutes；The purifying process of Flavonoid substances in celery celery oil
Are as follows: ethyl alcohol is extracted twice → combining extraction liquid → recycling ethyl alcohol and → vacuum freeze drying → celery oil flavones is concentrated；It will extraction
The celery oil flavones of taking-up loads macroreticular resin XAD-16 pillar, and after being activated well, wet process loading crude extract is successively used
Water, 10% ethyl alcohol, 20% ethanol elution, 30% ethyl alcohol, 50% ethyl alcohol, 70% ethyl alcohol, 95% ethanol elution is complete, collects each eluent,
Rotary evaporation recycles ethyl alcohol, and concentrate is in 80 DEG C.It is volatilized in water-bath, is dried in vacuo, obtains Primary purification part.Load polyamides
Amine column takes the Primary purification part of 30% ethyl alcohol, 50% ethanol eluate, mixes polyamide column on sample after processing, successively use water, 30%
Ethanol elution collects 30% eluent, rotary evaporation, and concentrate is volatilized in 80 DEG C of water-baths, is dried in vacuo, obtains purification part
As flavone compound (referring to structural formula 1).
Following tests is application of the flavone compound of the invention being prepared in medical application
Test example 1: the present invention, the influence to Oteracil Potassium and yeast extract solution induced mice hyperuricemia
Flavone compound (referred to as: the present invention) prepared by embodiment 1, embodiment 2, embodiment 3 is divided into two dosage groups:
3g/kg, 1.5g/kg, 0.75g/kg, with olive oil at the suspension of (1.2g/ml, 0.6g/ml, 0.3g/ml) concentration.It is non-
Bu Sita piece olive oil at 0.6g/ml concentration suspension.The dosage of yeast soln is 20g/kg.
Male Balb/c mouse 78 of 18-22 grams are taken, are randomly divided by weight: Normal group, model control group, sun
Property control group Febustat piece 6mg/kg, 1 ~ embodiment 3:3g/kg, 1.5g/kg, 0.75g/kg group of the embodiment of the present invention, administration
Group is outer for every group 12, and blank, model, positive controls are every group 14.From daystart, every morning Febustat
Corresponding solution is given in group, present invention group each group stomach-filling；Every afternoon, it is molten to give yeast for the equal stomach-filling of remaining each group in addition to blank group
Liquid.The group that stomach-filling is not required in experimentation then gives equivalent olive oil as control.From the 5th day to the 7th day, in yeast stomach-filling
After 1 h, in addition to blank group, each group be injected intraperitoneally Oteracil Potassium solution, dosage 300mg/kg.Blank group injects equivalent
Physiological saline.After the last administration, be spaced 3 hours after in it is interior adjoin take blood, 3000r/min be centrifuged 10min.Supernatant is taken after centrifugation again,
3000r/min centrifugation 5min takes supernatant.Each group mouse blood uric acid is measured by kit method and xanthine oxidase is horizontal.
Influence of the present invention to hyperuricemia mouse uric acid level and xanthine oxidase level the results are shown in Table 1, table 2:
Table 1 is the influence of Oteracil Potassium Yu yeast extract solution induced mice uric acid
| Group | Dosage (/kg) | Administration route | Size of animal (only) | UA (χ ± SD, μm ol/L) |
| Normal control | 20ml | ig | 14 | 261.2383±88.43 |
| Model comparison | 20ml | ig | 14 | 348.601±60.299# |
| Febustat | 6mg | ig | 14 | 59.615±18.044** |
| Embodiment 1 | 3.00g | ig | 12 | 247.668±86.524* |
| Embodiment 2 | 1.50 | ig | 12 | 203.282±61.749* |
| Embodiment 3 | 0.75g | ig | 12 | 171.332±48.777** |
Compared with normal group, #P < 0.05；Compared with model group, */* * P < 0.05, P < 0.01；
Table 2 is the influence of Oteracil Potassium Yu yeast extract solution induced mice XOD
| Group | Dosage (/kg) | Administration route | Size of animal (only) | XOD (χ ± SD, U/L) |
| Normal control | 20ml | ig | 14 | 0.05197±0.00607 |
| Model comparison | 20ml | ig | 14 | 0.06227±0.00952# |
| Febustat | 6mg | ig | 14 | 0.05538±0.00503 |
| Embodiment 1 | 3.00g | ig | 12 | 0.04762±0.004338** |
| Embodiment 2 | 1.50 | ig | 12 | 0.05083±0.00545 |
| Embodiment 3 | 0.75g | ig | 12 | 0.05272±0.00495* |
Conclusion: the present invention is compared with normal group, #P < 0.05；Compared with model group, */* * P < 0.05, P < 0.01.Prove the present invention
It is horizontal to can reduce the gentle xanthine oxidase of hyperuricemia mouse retention sour water.
Test example 2: the present invention is to the arthritic relaxation effect of rat acute gout row
Flavone compound 2-(2,4- dihydroxy -5- methoxyphenyl prepared by embodiment 1, embodiment 2, embodiment 3) -5,
Three dosage groups of 7- dihydroxy -4H- chromene -4- ketone (the referred to as present invention): 2g/kg, 0.5g/kg, with olive oil at concentration
The solution of 0.4g/ml, 0.1g/ml.Colchicines tablets olive oil at concentration 0.04mg/ml suspension.
180-200gWistar male rat 72 are selected, is randomly divided into blank control group by weight, model control group is positive
Control group, 2-(2,4- dihydroxy -5- methoxyphenyl) -5,7- dihydroxy -4H- chromene -4- ketone group: 2g/kg, 1g/kg,
0.5g/kg.According to dosage gastric infusion is primary daily for every group of 12 groups of animals, and continuous 8 days, control group and model group gave equivalent
Olive oil.After 5th day stomach-filling 1h, in the uric acid sodium solution of rat knee joints chamber injection 30g/L, volume injected is 100 μ L.It is empty
White group of injection same amount of normal saline is as control.Measure 0h, 12h respectively, for 24 hours with the rat articular perimeter of 48h.After data processing
The swelling rate in joint is obtained, as a result such as Fig. 1, compared with normal group, P < 0.05/P < 0.01 #/##；Compared with model group, * P <
0.05；Show that all administration groups have inhibiting effect to the arthroncus of rat.
Claims (4)
1. a kind of flavone compound, title are as follows: 2-(2,4- dihydroxy -5- methoxyphenyl) -5,7- dihydroxy -4H- chromene -
4- ketone, it is characterised in that have following structure formula:
Molecular formula are as follows: C1507H12；Molecular weight are as follows: 304.241.
2. a kind of preparation method of flavone compound as described in claim 1, comprising the following steps:
1) by 5~10s of celery seed crushed after being dried；
2) smashed celery seed is extracted with supercritical carbon dioxide extraction equipment: extracting pressure 25Mpa, temperature 30
℃；Separating pressure 8Mpa, 32 DEG C of temperature: each extraction time is 2 hours and every 15 minutes collection celery oil；
3) celery oil and the ethyl alcohol of volume fraction 70% carry out being mixed and heated to 80 DEG C of refluxing extractions twice according to the ratio of 1:5,
Combined extract recycles ethyl alcohol, and extracting solution volatilizes under 80 DEG C of water bath conditions, carries out vacuum freeze drying later and obtains celery oil
Flavones；
4) the celery oil flavones extracted is first purified to obtain Primary purification part, Zhi Houyong with macroreticular resin XAD-16 pillar
Polyamide column is further purified and is dried in vacuo, and obtaining purification part is flavone compound.
3. a kind of medical application of the flavone compound as described in claim 1 in preparation inhibiting hyperuricemia drug.
4. a kind of flavone compound as described in claim 1 is preparing the medical use in acute gouty arthritis drug
On the way.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114317102A (en) * | 2021-12-02 | 2022-04-12 | 山东省农业科学院 | Preparation method of celery seed oil and product thereof |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN105560262A (en) * | 2016-01-04 | 2016-05-11 | 中国科学院昆明植物研究所 | Application of Graveobioside A in preparation of drugs or healthcare food for preventing hyperuricemia and gout |
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2018
- 2018-08-21 CN CN201810953058.6A patent/CN109096238A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105560262A (en) * | 2016-01-04 | 2016-05-11 | 中国科学院昆明植物研究所 | Application of Graveobioside A in preparation of drugs or healthcare food for preventing hyperuricemia and gout |
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| MD. AZIZ ABDUR RAHMAN，等: "Isoetin 5"-Methyl Ether, A Cytotoxic Flavone from Trichosanthes kirilowii", 《BULL. KOREAN CHEM. SOC.》 * |
| 姚芳芳，等: "槲皮素和芹菜素对高尿酸血症大鼠血尿酸及抗氧化能力的影响", 《食品科学》 * |
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| CN114317102A (en) * | 2021-12-02 | 2022-04-12 | 山东省农业科学院 | Preparation method of celery seed oil and product thereof |
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Application publication date: 20181228 |