CN107652179A - A kind of method that forulic acid is extracted from Desmodium styracifolium - Google Patents
A kind of method that forulic acid is extracted from Desmodium styracifolium Download PDFInfo
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- CN107652179A CN107652179A CN201711044789.0A CN201711044789A CN107652179A CN 107652179 A CN107652179 A CN 107652179A CN 201711044789 A CN201711044789 A CN 201711044789A CN 107652179 A CN107652179 A CN 107652179A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/47—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/48—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
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Abstract
The invention discloses a kind of method that forulic acid is extracted from Desmodium styracifolium, comprise the steps:Comprise the following steps:1) Desmodium styracifolium 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, 160 170 DEG C of extraction temperature, the 10Mpa of pressure 8, the 1.0h of extraction time 0.5, Desmodium styracifolium 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 a kind of that forulic acid is extracted from Desmodium styracifolium
Method.
Background technology
Forulic acid (Ferulic acid), alias ferulic acid, molecular formula, C10H10O4, molecular weight:
194.19, it is one of derivative of cinnamic acid (also known as cinnamic acid, the acrylic acid of 3 phenyl 2, molecular structure).Forulic acid can be removed certainly
By base, promote to remove the generation of the enzyme of free radical, increase Glutathione S transferase and the activity of quinone reductase, and suppress tyrosine
Enzymatic activity, to adjust human physiological functions.Pharmacological action:With platelet aggregation-against, suppress platelet 5-HT release, suppression
The generation of platelet thrombus element A2 (TXA2) processed, strengthen prostaglandin activity, analgesia, alleviate the effect such as vasopasm.It is production
For treating the base stock of the disease medicine such as cardiovascular and cerebrovascular disease and Neuroleptic Leukocytopenia.As Sodium Ferulate, Limai capsule, Mrs are oral
Liquid etc., it can play a part of vigorous and graceful and protection skin in human body simultaneously.
Desmodium styracifolium (Herba Desmodii styracifolii) is parts of generic medicinal plants, is wide money in legume
The ground drying nest of careless [Desmodium styracifolium (Osh.) Merr.], is embodied in《People's Republic of China's medicine
Allusion quotation》In versions in 2010.Former plant is suffruticose draft, is distributed in the provinces and regions such as Guangdong, Guangxi, Fujian, Hunan, and Guangdong is medicinal material
Main producing region, be mainly used as medicine with its branches and leaves, have clearing heat and expelling damp, it is treating stranguria, row stone function, for urinary tract infections, stone in urinary system,
The illnesss such as cholecystolithiasis, ephritis edema.The prescription of lithangiuria illness is cured mainly, much using Desmodium styracifolium as monarch drug in a prescription, its curative effect is quite
It is good.Desmodium styracifolium has the hot dampness removing that disappears, Tonglin Paishi effect, contains all multicomponents such as flavonoids, saponins, tannin and alkaloid.
Proved by pharmacological research:The general flavone of Desmodium styracifolium possesses the effect that prevention calcinm oxalate calculus is formed and recurred, in addition, also having
The effect of significant anti-inflammatory and increase coronary blood flow etc..
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 a kind of method that forulic acid is extracted from Desmodium styracifolium, has technique simple, is adapted to
Production, the advantages that time is short.
The present invention is achieved through the following technical solutions.
A kind of method that forulic acid is extracted from Desmodium styracifolium, specifically comprises the following steps:
1) Desmodium styracifolium 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, 160-170 DEG C of extraction temperature, pressure 8-10Mpa, extraction time
0.5-1.0h, Desmodium styracifolium is extracted, extraction terminates, pressure release, and extract flows into collecting tank and is cooled to room temperature, is extracted
Take 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 forulic acid that the method for the present invention obtains, content exist
More than 99.0%, 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 forulic acid 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:
A kind of method that forulic acid is extracted from Desmodium styracifolium, specifically comprises the following steps:
1) Desmodium styracifolium 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, 160-170 DEG C of extraction temperature, pressure
Power 8-10Mpa, extraction time 0.5h, is extracted to Desmodium styracifolium, and extraction terminates, pressure release, and extract flows into cold in collecting tank
But 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:
A kind of method that forulic acid is extracted from Desmodium styracifolium, specifically comprises the following steps:
1) Desmodium styracifolium 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, 160-170 DEG C of extraction temperature, pressure
Power 8-10Mpa, extraction time 1.0h, is extracted to Desmodium styracifolium, and extraction terminates, pressure release, and extract flows into cold in collecting tank
But 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:
A kind of method that forulic acid is extracted from Desmodium styracifolium, specifically comprises the following steps:
1) Desmodium styracifolium 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, 160-170 DEG C of extraction temperature, pressure
Power 8-10Mpa, extraction time 1.0h, is extracted to Desmodium styracifolium, and extraction terminates, pressure release, and extract flows into cold in collecting tank
But 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:Weigh dry Desmodium styracifolium coarse powder (crossing 20 mesh sieves) 10g, water 10mL, immersion
30min, boiling 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, 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 styracifolium coarse powder (crossing 20 mesh sieves) 10g is weighed, adds 60% ethanol 100mL,
Backflow 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 styracifolium coarse powder (crossing 20 mesh sieves) 10g is weighed, adds 10 times of amount water to mix,
Cellulase 006g, enzymolysis 1h (temperature 50 C, pH 6) are added, then with 60% ethanol solution relative to 6 times of amounts of coarse powder
1h, cooling filtration are extracted, 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, dense
20mL is reduced to, 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, ferulaic acid content assay method (HPLC)
Chromatographic condition C18Chromatographic column (4.6mm × 250mm, 5 μm);Mobile phase is methanol:1% glacial acetic acid (45:55), detect
Wavelength is 320nm, and flow velocity 1.0ml/min, column temperature is 25 DEG C;Detection wavelength 270nm, 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 ferulaic acid content (%) after being reused many times
When resin is reused 4 times, compared to for the first time, have dropped 3.2%, resin repeats the ferulaic acid content of embodiment 3
During using 8 times, the ferulaic acid content of embodiment 3 have dropped 5.0%, 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)
- A kind of 1. method that forulic acid is extracted from Desmodium styracifolium, it is characterised in that comprise the following steps:1) Desmodium styracifolium 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, 160-170 DEG C of extraction temperature, pressure 8-10Mpa, extraction time 0.5- 1.0h, Desmodium styracifolium 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 is carried out by macroreticular resin, 50%v/v ethanol elution, Eluent is obtained, is concentrated, dries, obtains finished product.
- A kind of 2. method that forulic acid is extracted from Desmodium styracifolium according to claim 1, it is characterised in that:Step 1) institute The sieving stated, it was 20-80 mesh sieves.
- A kind of 3. method that forulic acid is extracted from Desmodium styracifolium according to claim 1, it is characterised in that:Step 2) institute That states injects deionized deoxygenated water in kettle, is with the flow velocity injection kettle less than 10mL/min by deionized deoxygenated water.
- A kind of 4. method that forulic acid is extracted from Desmodium styracifolium according to claim 1, it is characterised in that:Step 3) institute The concentration stated, temperature control≤50 DEG C, vacuum control are concentrated into 0.95-1.05g/ml in -0.08 ± 0.01MPa.
- A kind of 5. method that forulic acid is extracted from Desmodium styracifolium according to claim 1, it is characterised in that:Step 3) institute The macroreticular resin stated, resin model are selected from D101, DM130 and AB-8.
- A kind of 6. method that forulic acid is extracted from Desmodium styracifolium according to claim 1, it is characterised in that:Step 3) institute That states carries out column chromatography by macroreticular resin, is wet method dress post, sample concentration 8.0mg/mL, applied sample amount 3BV, during elution, first , the subsequent 50%v/v ethanol elution of using 6BV closely colourless to efflux, collection eluent is washed with water.
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Cited By (1)
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CN107674066A (en) * | 2017-10-31 | 2018-02-09 | 桂林纽泰生物科技有限公司 | A kind of method that Isoschaftoside is extracted from Desmodium styracifolium |
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