CN107805234A - The method that Quercetin is extracted from desmodium - Google Patents
The method that Quercetin is extracted from desmodium Download PDFInfo
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- CN107805234A CN107805234A CN201711044809.4A CN201711044809A CN107805234A CN 107805234 A CN107805234 A CN 107805234A CN 201711044809 A CN201711044809 A CN 201711044809A CN 107805234 A CN107805234 A CN 107805234A
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- desmodium
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- quercetin
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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
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/28—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only
- C07D311/30—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only not hydrogenated in the hetero ring, e.g. flavones
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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
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/40—Separation, e.g. from natural material; Purification
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- Organic Chemistry (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention discloses the method that Quercetin is extracted from desmodium, comprise the steps:Comprise the following steps:1) desmodium is cleaned up, dried, crushed with pulverizer, sieved;2) Subcritical Water Extraction:The raw material handled well is placed in extraction kettle, add the hydroxyethyl cellulose equivalent to the parts by weight of raw material 0.001, deionized deoxygenated water is injected in kettle, 170 185 DEG C of extraction temperature, the 10Mpa of pressure 8, the 1.0h of extraction time 0.5, desmodium is extracted, extraction terminates, pressure release, extract flows into collecting tank and is cooled to room temperature, obtains extract;3) purify:The extract that step 2) is obtained concentrates, and carries out column chromatography by macroreticular resin, 50%v/v ethanol elution, obtains eluent, concentrate, dries, obtain finished product.
Description
Technical field
The present invention relates to the extracting method of biological technical field, and in particular to the method that Quercetin is extracted from desmodium.
Background technology
Quercetin (Quercetin), also known as:Quercetin, Quercetin, molecular formula C15H10O7, molecular weight 302.23, physics and chemistry
Matter:Yellow needles, glacial acetic acid is dissolved in, alkaline aqueous solution is in yellow, is practically insoluble in water, and ethanol solution taste is very bitter.Quercitrin
Element category flavone compound, exists more in the form of glucoside, Quercetin is can obtain through sour water solution.Quercetin can be used as medicine, tool
There are preferable eliminating the phlegm, antitussive action, and have certain antiasthmatic effect.In addition with reduce blood pressure, strengthen capillary resistance,
Reduce the effect such as capillary fragility, reducing blood lipid, coronary artery dilator, increase coronary blood flow.For treating chronic bronchial
It is scorching.Also there is auxiliary therapeutic action to coronary heart disease and hyperpietic.
Desmodium is the fresh of Ofthe Primulaceae Lysimachia christinae (Lysimachiachristinae Hance) or is dried complete
Grass, main product is in Jiangsu, Guangdong, Sichuan, Guangxi.In addition, the ground such as Zhejiang, Hunan, Fujian also produces.Desmodium contain phenolic constituent,
The compositions such as flavonoids, glycoside, tannin, volatile oil, amino acid, choline, sterol, potassium chloride, lactone.According to the literature, money
The effect of grass tool row's stone, it is mainly used in treating the diseases such as jaundice with damp-heat pathogen, liver and bile stone, lithangiuria, bacterium infection.
Extraction of the prior art to flavones, ultrasonic extraction method Flavonoid substances mainly are used, its principle is ultrasonic
Destruction of the cavitation to cell membrane, contributing to the release and dissolution of flavone compound, ultrasonic wave makes extract solution constantly shake,
Promote solutes accumulation, concussion effect caused by ultrasonic wave may additionally facilitate the release, diffusion and dissolving of intracellular matter, be advantageous to carry
The recovery rate of high extract.The fuel factor of ultrasonic wave makes water temperature at 57 DEG C, there is water-bath effect to raw material substantially simultaneously.Therefore, surpass
Sonic method shortens extraction time, improves the extraction rate of active ingredient, the utilization rate of raw material relative to heating extraction.Have big
Measure document report and extract Flavonoid substances from the root of kudzu vine, Chinese celery, duck wheat, ginkgo leaf etc..
Existing extracting process, application steam distillation and organic solvent extractionprocess in terms of volatile oil are at present should
With widest traditional plant volatile oil or the extracting process of active ingredient, but operating time length, high energy consumption, poor selectivity, have
The defects of solvent easily remains is so that the industrialization of both conventional methods, scale application are greatly limited.SFE technologies
So that its is nontoxic, residual quantity is low, active ingredient is not easy the advantages that destroyed and enjoys praise.But due to common solvent C02With non-pole
Property and relative molecular mass it is small the characteristics of so that it is relatively low to the solubility of Cucumber, selectivity is not high and makes extraction effect simultaneously
It is undesirable, often extraction yield is improved by adding entrainer in practical operation, after extraction terminates, it is necessary to try to remove volatilization
Entrainer in oil, this certainly will cause the complexity of technique and the loss and oxidation of volatile component;Do not dissolved in additionally, due to water
C02, thus overcritical C02Often raw material need to be pre-dried for extraction process, adds additional cost, also make phenolic compound oily
Lose.In addition, when volatile oil is extracted from plant, due to overcritical C02Not only to volatile oil but also to the change of low polarity
Wax, aliphatic acid, coloring matter and resin in compound such as cuticula also have a similar dissolubility, these materials in extraction process
Also can be extracted, it is cumbersome and to equipment although purer volatile oil can also be obtained using complicated system
It is it is required that also more harsh.
The critical pressure of water and critical-temperature are respectively 22.1MPa and 374 DEG C, in f>374 DEG C, p>Under the conditions of 22.1MPa,
The dielectric constant of water is 5-15.It is referred to as in the low temperature pressure more slightly lower with 22.1MPa than 374.2 DEG C into the water of liquid condition
" subcritical water ".Heat water to more than boiling point, below critical point, and control system pressure makes water remain liquid, this shape
The water of state is referred to as subcritical water, and it is referred to as superheated water and high-temperature water also to have it in the literature.Under usual conditions, water is polar compounds
Thing.Under 505kPa pressure, raise (50-300 DEG C) with temperature, its dielectric constant is decreased to 1 by 70, that is to say, that its property by
It is highly polar to fade to nonpolar, solute can be extracted from high to low by polarity.Under conditions of temperature and pressure is all higher,
The polarity of water reduces, can be with extracting apolar compound;Under conditions of temperature and pressure is all relatively low, the polarity of water improves, can be with
Extract polar compound.During actual extraction, because the influence that influences be not so good as temperature of the pressure to dielectric constant is big, so
Mainly the dielectric constant of water is controlled by adjusting temperature.Due to be without using acid, alkali and catalyst water under high thermal high
Treatment technology, therefore the extracting method of subcritical water is referred to as " green facture ".In addition, extraction can be in the several seconds
Completed in several minutes of short time, so with the advantages of can carrying out continuous processing.Subcritical Water Extraction technology is natural
There is very much prospect in the extraction of the active component in product field.
The content of the invention
It is an object of the invention to provide the method that Quercetin is extracted from desmodium, has technique simple, is adapted to production, when
Between it is short the advantages that.
The present invention is achieved through the following technical solutions.
The method that Quercetin is extracted from desmodium, specifically comprises the following steps:
1) desmodium is cleaned up, dried, crushed with pulverizer, sieved;
2) Subcritical Water Extraction:The raw material handled well is placed in extraction kettle, added equivalent to the parts by weight of raw material 0.001
Hydroxyethyl cellulose, deionized deoxygenated water is injected in kettle, 170-185 DEG C of extraction temperature, pressure 8-10Mpa, extraction time
0.5-1.0h, desmodium is extracted, extraction terminates, pressure release, and extract flows into collecting tank and is cooled to room temperature, is extracted
Liquid;
3) purify:The extract that step 2) is obtained is concentrated, and column chromatography, 50% (v/v) second are carried out by macroreticular resin
Alcohol elutes, and obtains eluent, concentrates, and dries, obtains finished product.
Sieving described in step 1) of the present invention, preferably cross 20-80 mesh sieves.
Deionized deoxygenated water is injected in kettle described in step 2), preferably by deionized deoxygenated water with less than 10mL/min's
In flow velocity injection kettle, solid-liquid ratio 1:2-3.
Concentration described in step 3), preferable temperature control≤50 DEG C, and vacuum control is concentrated into -0.08 ± 0.01MPa
0.95-1.05g/ml。
Macroreticular resin described in step 3), resin model preferred D101, DM130 and AB-8.
Column chromatography, preferably wet method dress post, sample concentration 8.0mg/mL, loading are carried out by macroreticular resin described in step 3)
Measure as 3BV, during elution, be first washed with water closely colourless to efflux, then use 6BV 50% (v/v) ethanol elution, collect elution
Liquid.
Compared with prior art, advantages of the present invention:
1st, in the prior art, either ultrasonic extraction method, heating extraction, enzymolysis and extraction etc., ash rate is higher, typically exists
3-5% or so, and many American-European clients also require ash content below 3% while high content is required now, and existing work
Skill, traditional technique can not directly produce the product of such specification.And the Quercetin that the method for the present invention obtains, content exist
More than 99.5%, ash content is below 1.5%.
2nd, for the present invention in Subcritical Water Extraction, it is crucial that a certain amount of hydroxyethyl cellulose is added in material.Preceding
If the phase it was found that, do not add hydroxyethyl cellulose, directly using Subcritical Water Extraction, obtained final products ash
Divide (3% or so) compared to the prior art there is no otherness, and add hydroxyethyl cellulose, then can significantly reduce final production
Product ash content (less than 1.5%), analysis are because extraction quantity is with extraction temperature and extraction time during Subcritical Water Extraction
Increase and increase, extract the dissolution of product, while active component dissolution, the dissolution of other compositions can also increased,
And with the addition of hydroxyethyl cellulose, a certain degree of parcel is formd to the material of extraction, can be in the molten of active component
Go out and prevent from reaching a balance between the dissolutions of other impurities.
3rd, the purifying after existing extracting method, the reuse of resin, typically at 3-4 times, the rate of recovery of Quercetin can under
Drop, content is caused to decline, it is necessary to regenerate, and the method for using the present invention, resin may be reused more than 8 times, just need to regenerate,
A large amount of man-hours and cost are saved.
Embodiment
With embodiment, the invention will be further described below, but the invention is not limited in these embodiments.
Embodiment 1:
The method that Quercetin is extracted from desmodium, specifically comprises the following steps:
1) desmodium is cleaned up, dried, crushed with pulverizer, cross 20 mesh sieves;
2) Subcritical Water Extraction:The raw material handled well is placed in extraction kettle, added equivalent to the parts by weight of raw material 0.001
Hydroxyethyl cellulose, deionized deoxygenated water is injected in kettle with the flow velocity less than 10mL/min, 170-185 DEG C of extraction temperature, pressure
Power 8-10Mpa, extraction time 0.5h, is extracted to desmodium, and extraction terminates, pressure release, and extract is flowed into collecting tank and cooled down
To room temperature, extract is obtained;
3) purify:The extract that step 2) is obtained concentrates, temperature control≤50 DEG C, vacuum control -0.08 ±
0.01MPa, 0.95-1.05g/ml is concentrated into, column chromatography, sample concentration 8.0mg/mL, loading are carried out by DM130 macroreticular resins
Measure as 3BV, during elution, be first washed with water closely colourless to efflux, then use 6BV 50% (v/v) ethanol elution, collect elution
Liquid, concentrate, dry, obtain finished product.
Embodiment 2:
The method that Quercetin is extracted from desmodium, specifically comprises the following steps:
1) desmodium is cleaned up, dried, crushed with pulverizer, cross 40 mesh sieves;
2) Subcritical Water Extraction:The raw material handled well is placed in extraction kettle, added equivalent to the parts by weight of raw material 0.001
Hydroxyethyl cellulose, deionized deoxygenated water is injected in kettle with the flow velocity less than 10mL/min, 170-185 DEG C of extraction temperature, pressure
Power 8-10Mpa, extraction time 1.0h, is extracted to desmodium, and extraction terminates, pressure release, and extract is flowed into collecting tank and cooled down
To room temperature, extract is obtained;
3) purify:The extract that step 2) is obtained concentrates, temperature control≤50 DEG C, vacuum control -0.08 ±
0.01MPa, 0.95-1.05g/ml is concentrated into, column chromatography, sample concentration 8.0mg/mL, loading are carried out by AB-8 macroreticular resins
Measure as 3BV, during elution, be first washed with water closely colourless to efflux, then use 6BV 50% (v/v) ethanol elution, collect elution
Liquid, concentrate, dry, obtain finished product.
Embodiment 3:
The method that Quercetin is extracted from desmodium, specifically comprises the following steps:
1) desmodium is cleaned up, dried, crushed with pulverizer, cross 80 mesh sieves;
2) Subcritical Water Extraction:The raw material handled well is placed in extraction kettle, added equivalent to the parts by weight of raw material 0.001
Hydroxyethyl cellulose, deionized deoxygenated water is injected in kettle with the flow velocity less than 10mL/min, 170-185 DEG C of extraction temperature, pressure
Power 8-10Mpa, extraction time 1.0h, is extracted to desmodium, and extraction terminates, pressure release, and extract is flowed into collecting tank and cooled down
To room temperature, extract is obtained;
3) purify:The extract that step 2) is obtained concentrates, temperature control≤50 DEG C, vacuum control -0.08 ±
0.01MPa, 0.95-1.05g/ml is concentrated into, column chromatography, sample concentration 8.0mg/mL, loading are carried out by D101 macroreticular resins
Measure as 3BV, during elution, be first washed with water closely colourless to efflux, then use 6BV 50% (v/v) ethanol elution, collect elution
Liquid, concentrate, dry, obtain finished product.
In early stage, by contrast experiment, effect is carried out to Different Extraction Method and has compared (the same embodiment of following purification steps
3):
Comparative example 1:
The preparation of water extraction extract solution:Dry desmodium coarse powder (crossing 20 mesh sieves) 10g, water 10mL is weighed, soaks 30min,
Boil rear slow fire and decoct 40min slowly, filtered while hot with 4 layers of gauze, the dregs of a decoction add water 100mL, decoct 30min after boiling slowly again, filter while hot
Cross, merge decocting liquid twice, be concentrated to 20mL, 50% methanol dissolves and is settled to 50mL.
Comparative example 2:
The preparation of alcohol extracting method extract solution:Dry desmodium coarse powder (crossing 20 mesh sieves) 10g is weighed, adds 60% ethanol 100mL, returns
Stream twice, first time 2h, second of 1.5h, merges extract solution twice, is concentrated to 20mL, 50% methanol dissolves and is settled to
50mL。
Comparative example 3:
The preparation of enzymatic isolation method extract solution:Dry desmodium coarse powder (crossing 20 mesh sieves) 10g is weighed, adds 10 times of amount water to mix, then
Cellulase 006g, enzymolysis 1h (temperature 50 C, pH 6) are added, is then carried with 60% ethanol solution relative to 6 times of amounts of coarse powder
1h, cooling filtration are taken, the dregs of a decoction add 5 times of 60% alcohol reflux 30min of amount, cooling filtration, discard the dregs of a decoction, merge extract solution, concentration
To 20mL, 50% methanol dissolves and is settled to 50mL.
Comparative example 4:
The preparation of ultrasonic method extract solution:Coarse powder is ground into, weighs 30.0g, is put into 1000mL flask, adds 60%
Ethanol, it is put into ultrasonic machine and after ultrasonic extraction 30min at a temperature of 50 DEG C, stops ultrasound, filtering, merge extract solution, recovery
Solvent.
Experimental example
1st, quercetin content assay method (HPLC)
Chromatographic condition C18Chromatographic column (4.6mm × 250mm, 5 μm);Mobile phase is second eyeball (A):The formic acid of volume fraction 0.1%
The aqueous solution (B), Detection wavelength 254nm, flow velocity 1.0ml/min, column temperature are 30 DEG C;The μ L of sample size 10.
As a result:
2nd, resin stability is investigated:The D101 type dried resin lOg of pretreatment are weighed, wet method is fitted into chromatographic column, with 20mg/
ML loading 10mL, after 60mL water washings, with 50% ethanol elution to colourless, collection 8-48mL section eluents, then with largely
Water rinses pillar to without alcohol taste, and this process is 1 cycle.This process is repeated, collects the eluent of each collection, and is concentrated, is done
It is dry, weigh, calculate content.
Resin measures quercetin content (%) after being reused many times
When resin is reused 4 times, compared to for the first time, have dropped 3.5%, resin repeats the quercetin content of embodiment 3
During using 8 times, the quercetin content of embodiment 3 have dropped 5.4%, far better than comparative example compared to for the first time.
3rd, in the experiment of early stage, in Subcritical Water Extraction, applicant also added in material a certain amount of xanthans,
CMC, but effect and unobvious, compared with the technique without addition, effect does not have otherness.
Claims (6)
1. the method for Quercetin is extracted from desmodium, it is characterised in that comprise the following steps:
1) desmodium is cleaned up, dried, crushed with pulverizer, sieved;
2) Subcritical Water Extraction:The raw material handled well is placed in extraction kettle, adds the hydroxyl second equivalent to the parts by weight of raw material 0.001
Base cellulose, deionized deoxygenated water is injected in kettle, 170-185 DEG C of extraction temperature, pressure 8-10Mpa, extraction time 0.5-
1.0h, desmodium is extracted, extraction terminates, pressure release, and extract flows into collecting tank and is cooled to room temperature, obtains extract;
3) purify:The extract that step 2) is obtained is concentrated, and column chromatography is carried out by macroreticular resin, 50%v/v ethanol elution,
Eluent is obtained, is concentrated, dries, obtains finished product.
2. the method according to claim 1 that Quercetin is extracted from desmodium, it is characterised in that:Mistake described in step 1)
Sieve, was 20-80 mesh sieves.
3. the method according to claim 1 that Quercetin is extracted from desmodium, it is characterised in that:General described in step 2)
It is with the flow velocity injection kettle less than 10mL/min by deionized deoxygenated water in deionized deoxygenated water injection kettle.
4. the method according to claim 1 that Quercetin is extracted from desmodium, it is characterised in that:It is dense described in step 3)
Contracting, temperature control≤50 DEG C, vacuum control are concentrated into 0.95-1.05g/ml in -0.08 ± 0.01MPa.
5. the method according to claim 1 that Quercetin is extracted from desmodium, it is characterised in that:It is big described in step 3)
Hole resin, resin model are selected from D101, DM130 and AB-8.
6. the method according to claim 1 that Quercetin is extracted from desmodium, it is characterised in that:It is logical described in step 3)
Cross macroreticular resin and carry out column chromatography, be wet method dress post, sample concentration 8.0mg/mL, applied sample amount 3BV, during elution, be first washed with water
It is closely colourless to efflux, 6BV 50%v/v ethanol elutions are then used, collect eluent.
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Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1931228A (en) * | 2006-09-25 | 2007-03-21 | 沈阳药科大学 | Lysimachia herb total flavone extract and its prepn process |
CN103432196A (en) * | 2012-12-06 | 2013-12-11 | 重庆科瑞制药(集团)有限公司 | Desmodium styracifolium total flavonoids and preparation method of Desmodium styracifolium total flavonoids and total polysaccharides |
CN104224863A (en) * | 2014-06-25 | 2014-12-24 | 苏州凯祥生物科技有限公司 | Application of herba lysimachiae total flavonoids in preparation of medicine for relieving hyperuricemia |
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2017
- 2017-10-31 CN CN201711044809.4A patent/CN107805234A/en active Pending
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
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CN1931228A (en) * | 2006-09-25 | 2007-03-21 | 沈阳药科大学 | Lysimachia herb total flavone extract and its prepn process |
CN103432196A (en) * | 2012-12-06 | 2013-12-11 | 重庆科瑞制药(集团)有限公司 | Desmodium styracifolium total flavonoids and preparation method of Desmodium styracifolium total flavonoids and total polysaccharides |
CN104224863A (en) * | 2014-06-25 | 2014-12-24 | 苏州凯祥生物科技有限公司 | Application of herba lysimachiae total flavonoids in preparation of medicine for relieving hyperuricemia |
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