CN104744489B - Method for preparing high-purity oridonin by taking rabdosia rubescens as raw material - Google Patents
Method for preparing high-purity oridonin by taking rabdosia rubescens as raw material Download PDFInfo
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Abstract
The invention belongs to the field of biochemical industry, and particularly relates to a method for preparing high-purity oridonin by taking rabdosia rubescens as a raw material. According to the process, accurate coupling among various operation units is realized by adequately utilizing the similarity principle of a solvent and a compound during a separation and extraction process. The process mainly comprises the following steps: adjusting the polarity of the solvent and designing a two-time reflux extraction process to obtain aqueous solution containing oridonin; designing a macroporous resin dynamic separation process so as to primarily enrich oridonin from the aqueous solution; carrying out decolouration and further impurity removal on the extract obtained after pre-purification by a three-solvent two-phase extraction technology; carrying out an ultrasound-assisted cooling crystallization technology to further obtain oridonin crystals. The method disclosed by the invention overcomes such defects in the existing preparation method as high organic solvent consumption, complicated process and difficulty in realizing large-scale production, and develops a new Chinese style production process with low cost, high benefit and high-purity output for oridonin.
Description
Technical field
The invention belongs to biological chemical field, more particularly, to a kind of is raw material preparation high-purity winter icepro using Jiyuan Rabdosia rubescens
The method of careless A prime.
Background technology
Rabdosia rubescens are a kind of herbaceous plant of Chun Xing section Rabdosia, and its stem and leaf can be used as medicinal.This plant is extensive
It is distributed in provinces and regions on the south the Huanghe valley, wherein Jiyuan, Henan is the main place of production of this plant.Rabdosia rubescens have heat-clearing and toxic substances removing, antiinflammatory stops
Bitterly, stomach invigorating promoting blood circulation and its antineoplastic effect.And include this plant in the pharmacopeia published in 1977, medical treatment among the people
Historical data also once demonstrated that this plant can be used for treating multiple diseases such as esophageal carcinoma and medical value is notable.Once report in document
Road, contains multiple terpene substances in the stem of Rabdosia rubescens and leaf, including: diterpene, monoterpene, sesquiterpene and triterpene etc..Remove
Terpenoid accounts for outside main component, also has other native compounds to exist in this plant of Rabdosia rubescens, such as volatile oil, glycoside, polysaccharide, Huang
Ketone etc..Shown according to current pharmacology activity research result, the main compound playing clinical therapeutic efficacy in Rabdosia rubescens becomes
Dividing is rubescensine A.
Rubescensine A, its molecular formula is c20h28o6, molecular weight less, is worth for 364.42.Its compound scaffold such as Fig. 1.
This compound of forefathers' document report is easily soluble in methanol and acetone, insoluble in benzene, ether and chloroform, conventional Rabdosia rubescens production technology
In concentrate on the thinking of report organic solvent abstraction impurity removal and improve the purity of target product, organic solvent (petroleum ether and chlorine
Imitate) consumption is excessive, and it is not easy to the large-scale production of active skull cap components, and the technique productions of correlation are coarse, product matter
Amount is not high.
The design of native compound separation-extraction technology considers the similarity between target compound and impurity, then basis first
The structure of target compound comes the solvent of selective extraction, the eluting solvent during column chromatography for separation, the solvent of extraction and crystallization
Solvent.In technique, the Coupling Design between each operating unit depends on the similarity of target product and impurity, and institute in separation system
The similarity having compound structure is to be determined by the initial operating unit that extracts again.In addition, acetate-methanol-water
The three phase extraction of composition has no that report to purify decolouring in the purifying technique of rubescensine A, and this step is tied for ultrasonic wave added
The carrying out of brilliant final purification has been cooked the preparation ensureing crystal color and luster.
Content of the invention
It is an object of the invention to provide a kind of method preparing rubescensine A using Rabdosia rubescens, to solve above-mentioned asking
Topic.The embodiment provides a kind of method preparing rubescensine A using Jiyuan Rabdosia rubescens, comprise the steps:
A kind of method preparing high-purity rubescensine A using Rabdosia rubescens is it is characterised in that comprise the steps:
1) extraction process twice of rubescensine A
First have to through pulverizing for the Rabdosia rubescens stem in this technological design and leaf, its ground product carries out two kinds of solvents and carries
Take, first, dehydrated alcohol reflux, extract, extraction time is 1-3h, and the volume ratio extracting raw materials quality with Extraction solvent is 1:10-
13, the unit that this is measured is g/ml.Extracting temperature is 80 DEG C, and after extracting twice, united extraction liquid rotary evaporation is to extracting liquid volume
It is the 1/100 of former extracting liquid volume.Add water in extractor, its volume is the half of ethanol amount used, and at 100 DEG C, backflow carries
Take 1-3h.
2) hp-20 macroporous adsorbent resin industry prepurification experimental design
The macroporous resin column chromatography experiment of two kinds of scales, the i.e. bench scale of rubescensine A is accurately provided in this patent
Experiment and pilot-scale experiment.Specifically it is listed below:
Diameter for the glass packed column of bench scale and height are respectively 3cm and 100cm, hp-20 model macropore tree
The packing volume of fat is 300ml, and sample concentration is 0.5-0.65mg/ml, flow velocity 2-3.5ml/min, and loading volume is 5-6l.Wash
Separation of flow speed is 2-3.5ml/min, after washing 1500-2000ml, the ethanol elution being 20% with volume content, and front 1500-
2000ml is used for remove impurity, with being followed by the eluent that 7000-9000ml contains rubescensine A.
The diameter of the chromatographic column of pilot-scale and height are respectively 12cm and 2m.The hp-20 macroporous resin of 40l is packed into
In pillar, control sample solution concentration scope is 1-1.5mg/ml, flow rates 300-350ml/min of loading, and loading time is
11-13h.In elution step, flow velocity is 300-400ml/min, after the water elution of 200-280l, in the volume with 200-280l
Content is 20% ethanol water remove impurity, finally, is that 20% ethanol solution is used for eluting with the volume content of 900-1200l
Rubescensine A.
3) three kinds of solvent (acetate-methanol-aqueous solution) extraction decolourings remove impurity further
First, configuration volume content is 29% methanol aqueous solution, then by bodies such as ethyl acetate and this methanol aqueous solutions
Form three kinds of solution two-phase systems after long-pending mixing.It is pure that single extraction liquid volume and resin prepurification obtain containing in extractum
Rubescensine A mass ratio is 1:9-15, and the unit that this is measured is l/g.After extraction, collect ethyl acetate phase, rotation obtains after being evaporated
To rubescensine A extractum.
4) ultrasonic assistant crystallisation by cooling obtains the crystal of rubescensine A
Configuration volume content is 33% methanol aqueous solution, and the extractum obtaining after extraction is dissolved in this methanol aqueous solution
In, the concentration controlling rubescensine A is 45-53mg/ml, and ultrasonic in subsequent ultrasonic cleaner, ultrasonic temperature is 25 DEG C, surpasses
The sound time is 15-20min, and the big grain nucleus of white separates out, 4-6 DEG C of Refrigerator store 2 days, -8 DEG C of crystallization 10-12 hours afterwards.Centrifugation
Obtain solid crystal product, with the water washing product of 2l twice, be centrifuged after being statically placed in respectively every time 2 hours in -8 DEG C of crystallizer
Obtain white powder, drying machine drying obtains rubescensine A powder.
Further, step 1) volume ratio of extracting raw materials quality and Extraction solvent is 1:11, the unit that this is measured is g/ml,
The extraction time of ethanol is 2h, and the extraction time of water is also 2h.
Further, step 2) bench scale technique in, sample solution concentration be 0.55mg/ml, flow velocity be 2.5ml/min,
Loading volume is 6l.Elution flow rate is 2ml/min, and the volume of water lotion is 1800ml, is 20% second with 2000ml volume content
Alcohol-water solution volume is remove impurity, is subsequently that 20% ethanol water is collected winter of obtaining of prepurification and insulted with the volume content of 9000ml
Careless A prime product.Step 2) in pilot-scale technique, sample solution concentration is 1mg/ml, and loading flow velocity is 300ml/min, during loading
Between be 12h, elution flow rate be 300ml/min.Volume 200l of water lotion, is that 20% ethanol water is used with 240l volume content
In remove impurity, subsequently, it is that 20% ethanol water collects the rubescensine A product that prepurification obtains with the volume content of 1200l.
Further, step 3) single extraction liquid volume and resin prepurification obtain the pure Rabdosia rubescens first that contains in extractum
Plain mass ratio is 1:10, and the unit that this is measured is l/g.
Further, step 4) will after extraction the methanol 48mg/ml that the extractum that obtains is dissolved in 33% rubescensine A molten
Liquid, ultrasonic time 20min it can be seen that the big grain nucleus having white separates out, 4 DEG C of Refrigerator stores 2 days, -8 DEG C of crystallization 12h afterwards.
Compared with the rubescensine A production technology in existing document, the invention has the advantages that: used in this technique
Reagent be mainly water, dehydrated alcohol uses ethyl acetate and a small amount of first although also having in crucial extraction and crystalline element
Alcohol, but both reagent is micro with respect to water and ethanol consumption.A complete set of technique has avoided existing rubescensine A purification literary composition
The big organic reagent of multiple toxicity such as petroleum ether, chloroform, acetone and ether of being previously mentioned in offering.This technique introduces macroporous resin
Column chromatography for separation operating unit, this cell process operating condition is gentle, there is not environmental pollution, introduces three phase extraction skill in extraction
The reagent that art takes full advantage of three kinds of high isopolarities in solvent polarity table adjusts the effect that proportioning achieves decolorization and purification, finally surpasses
Sound wave assisting crystallisation technology has obtained 98% rubescensine A product, and this process costs is cheap, process is simple, yield
Height, suitable large-scale industrial production.
Brief description
Fig. 1 is chromatogram and this compound chemical structure figure of Rabdosia rubescens water crude extract
Fig. 2 is the process chart that a kind of utilization Jiyuan Rabdosia rubescens prepare high-purity rubescensine A
Fig. 3 is the analysis chart of the purity that the embodiment of the present invention 1 utilizes analytical type high-performance liquid chromatogram determination rubescensine A
Fig. 4 is the qualification figure that the embodiment of the present invention 1 is identified to product using mass spectrum
Specific embodiment
In order that the objects, technical solutions and advantages of the present invention become more apparent, below in conjunction with drawings and Examples, right
The present invention is described in further detail.It should be appreciated that described herein be embodied as only in order to explain the present invention, not
For limiting invention.
To joining shown in Fig. 4, Fig. 1 is the chemical molecules structure chart of rubescensine A to ginseng Fig. 1；Fig. 2 is that the present invention is a kind of to be utilized
The flow chart that Jiyuan Rabdosia rubescens prepare the method for rubescensine A；Fig. 3 is that the embodiment of the present invention 1 utilizes analytical type high-efficient liquid phase color
Spectrum measures the analysis chart of rubescensine A purity；Fig. 4 is the identification that the embodiment of the present invention 1 is identified to product using mass spectrum
Figure.
Embodiments of the present invention provide the method preparing rubescensine A using Rabdosia rubescens, comprise the following steps:
1) extraction process twice of rubescensine A
First have to through pulverizing for the Rabdosia rubescens stem in this technological design and leaf, its ground product carries out two kinds of solvents and carries
Take, first, dehydrated alcohol reflux, extract, extraction time is 1-3h (can be 1h, 2h, 3h), extracts raw materials quality molten with extraction
The volume ratio of agent is 1:10-13 (can be 1:10,1:11,1:12,1:13), and the unit that this is measured is g/ml.Extracting temperature is
80 DEG C, after extracting twice, united extraction liquid rotary evaporation to extracting liquid volume is the 1/20 of former extracting liquid volume.To in extractor
Add water, its volume is the half of ethanol amount used, at 100 DEG C, reflux, extract, 1-3h (can be 1h, 2h, 3h).
2) hp-20 macroporous adsorbent resin industry prepurification experimental design
Macroporous resin is one kind industrial column chromatography filled media very well as a kind of organic polymer spherical medium.Natural
In the prepurification commercial production of compound, this macroporous resin packed column can play the effect of its efficiently concentrating compound well
Fruit is capable of dynamically to the adsorption of native compound and this operating unit of column chromatography depending on resin polymer itself
Produce.In that patent, we to have selected hp-20 after having taken into full account the property of this triterpenoid compound of rubescensine A big
Macroporous adsorbent resin is tested as the filled media of pillar, the macroporous resin column chromatography having carried out two kinds of scales:
Diameter for the glass packed column of bench scale and height are respectively 3cm and 100cm, hp-20 model macropore tree
The packing volume of fat is 300ml, and sample concentration (can be 0.5mg/ml, 0.55mg/ml, 0.6mg/ for 0.5-0.65mg/ml
Ml, 0.65mg/ml), flow velocity 2-3.5ml/min (can be 2ml/min, 2.5ml/min, 3ml/min, 3.5ml/min), loading
Volume is 5-6l (can be 5l, 5.2l, 5.4l, 5.6l, 5.8l, 6l).Elution flow rate (can be 2ml/ for 2-3.5ml/min
Min, 2.5ml/min, 3ml/min, 3.5ml/min), washing 1500-2000ml (can for 1500ml, 1600ml, 1700ml,
1800ml, 1900ml, 2000ml) after, the ethanol elution being 20% with volume content, front 1500-2000ml (can be
1500ml, 1600ml, 1700ml, 1800ml, 1900ml, 2000ml) it is used for remove impurity, with being followed by 7000-9000ml (can be
7000ml, 7500ml, 8000ml, 8500ml, 9000ml) eluent containing rubescensine A.
The diameter of the chromatographic column of pilot-scale and height are respectively 12cm and 2m.The hp-20 macroporous resin of 40l is packed into
In pillar, control sample solution concentration scope (can be 1mg/ml, 1.1mg/ml, 1.2mg/ml, 1.3mg/ for 1-1.5mg/ml
Ml, 1.4mg/ml, 1.5mg/ml), flow rates 300-350ml/min of loading (can for 300ml, 310ml, 320ml,
330ml, 340ml, 350ml), loading time is 11-13h (can be 11h, 11.5h, 12h, 12.5h, 13h).In elution step
Flow velocity is 300-400ml/min (can be 320ml/min, 340ml/min, 360ml/min, 380ml/min, 400ml/min),
After water elution with 200-280l (can be 200l, 220l, 240l, 260l, 280l), with 200-280l (can for 200l,
220l, 240l, 260l, 280l) volume content be 20% ethanol water remove impurity, finally, with 900l-1200l (can be
900l, 950l, 1000l, 1050l, 1100l, 1150l, 1200l) volume content be 20% ethanol solution be used for eluting
Rubescensine A.
3) three kinds of solvent (acetate-methanol-aqueous solution) extraction decolourings remove impurity further
Process before the extractum that macroporous resin prepurification is obtained is crystallized extracts.This step is for the color having obtained
The highly purified rubescensine A product in pool is most important.The methanol that configuration volume content is 29% is first had to water-soluble in this step
Liquid, then forms three kinds of solution two-phase systems by after ethyl acetate and the mixing of this methanol aqueous solution equal-volume.Single extraction liquid
The pure rubescensine A mass ratio that volume and resin prepurification obtain containing in extractum be 1:9-15 (can for 1:9,1:10,
1:11,1:12,1:13,1:14,1:15), the unit that this is measured is l/g.After extraction, collect ethyl acetate phase, after rotation is evaporated
Obtain rubescensine A extractum.
4) ultrasonic assistant crystallisation by cooling obtains the crystal of rubescensine A
Configuration volume content is 33% methanol aqueous solution, and the extractum obtaining after extraction is dissolved in this methanol aqueous solution
In, control rubescensine A concentration be 45-53mg/ml (can be 45mg/ml, 46mg/ml, 47mg/ml, 48mg/ml,
49mg/ml, 50mg/ml, 51mg/ml, 52mg/ml, 53mg/ml), ultrasonic in subsequent ultrasonic cleaner, ultrasonic temperature is 25
DEG C, ultrasonic time is 15-20min (can be 15min, 16min, 17min, 18min, 19min, 20min), and the big grain of white is brilliant
Core separates out, 4-6 DEG C of (can be 4 DEG C, 5 DEG C, 6 DEG C) Refrigerator store 2 days, afterwards -8 DEG C of crystallization 10-12h (can for 10h, 11h,
12h).Centrifugation obtains solid crystal product, with the water washing product of 2l twice, is statically placed in 2h in -8 DEG C of crystallizer every time respectively
Centrifugation obtains white powder afterwards, and drying machine drying obtains rubescensine A powder.
In this patent, whole rubescensine A production technology comprises four crucial operating units, between four units accurately
The point of penetration of coupling linking is exactly the thinking selecting solvent according to chromatogram.According in solvent polarity table, polarity is from big to small
It is sequentially water (polarity index is 10.2), methanol (polarity index 5.1), ethyl acetate (polarity index 4.4), (polarity refers to ethanol
Number 4.3).Our technique exactly have chosen the maximum solvent of these four polarity in solvent polarity table.In the stage of extraction, ethanol is first
First as initial Extraction solvent, the Rabdosia rubescens stem after pulverizing and leaf powder are extracted, according to the molecule of rubescensine A
Formula structure and molecular size range, theoretically can be determined that is under suitable commercial operating conditions, and ethanol is can be close
Completely extract in raw material contained thus rubescensine A.With ethanol as polarity yardstick minimum point, water is permissible
As the peak of polarity yardstick, thus, the extractum obtaining is carried out with second extraction to obtain containing Rabdosia rubescens after ethanol extraction
For the purpose of the Aqueous extracts of A prime, done preparation for the carrying out of macroporous resin column chromatography prepurification simultaneously.
The foundation of analytical type high performance liquid chromatography detection condition is not only extremely closed for the accurately qualitative and quantitative of compound
Important, it is even more the reliable criterion that crucial solvent in each lock out operation unit selects design.Used Rabdosia rubescens in this patent
The chromatographic test strip part of A prime is as follows: under ultraviolet detection wavelength 242nm, c18 enlightening horse pillar is fixing phase, methanol and aqueous solution
As mobile phase, proportion of mobile phase changes over as follows: in 0-22min, the ratio of methanol and water is: 53:47；22-30min
Interior, the ratio of water is reduced to 0 from 47%；In 30-38min, the ratio of methanol rises to 53%；38-45min, first alcohol and water ratio
Example is maintained at 53:47, and under this chromatographic test strip part, detection obtains Fig. 1 after the aqueous solution containing rubescensine A.
The retention time embodying rubescensine A in chromatogram is 19.07min, and in corresponding mobile phase, the ratio of methanol is classified as
53%.In macroporous resin column chromatography, purification thinking concentrates on and selects water and ethanol maximum and polarity minimum respectively as polarity
Solvent obtains eluting solvent after adjusting the two proportioning.Both solvents are not only in place in four kinds of solvents that we are considered
Put and be in two ends, for two kinds of middle solvents, water and environment protection type ethanol avirulence, it is suitable in the conduct of prepurification stage
Eluant occurs.In chromatographic test strip part, methanol is chosen as eluant, but, if selecting methanol to occur in greatly as eluant
If the hole resin pillar prepurification stage, the boiling point of methanol is high also to bring difficulty to the revolving after prepurification, lead to energy consumption
Greatly.By contrast, ethanol is more suitable.
When second alcohol and water is as the eluant of macroporous resin column chromatography, pushing away by analytical type chromatogram principle
Can be regarded as and occur being used as the foundation that during resin chromatography separates, eluant selects for this patent core.In the prepurification stage, remove impurity is point
From main target, from chromatogram, exist obvious impurity peaks 1 target product go out peak position before, this is miscellaneous
The retention time of matter is 9.408min.Polarity parameters and retention time are simultaneously introduced reckoning below: ethanol in resin eluant
Concentration=9.408/19.07 × 53% × 4.3/5.1=22.05% ≈ 20%, select 20% ethanol water as eluting
Agent is to have a mind to have slowed down elution speed to ensure that Chinese style column chromatography obtains the purity of product and the stability of dynamic desorption.
Select water, methanol, this three kinds of solvents of ethyl acetate in three kinds of solvent extractions, be only primarily due to the polarity of methanol
Less than water, the two forms aqueous solution.Usually introduce in common technique is the two-phase extraction technique of ethyl acetate and water, this kind of
Selecting can be with water significantly split-phase based on ethyl acetate.When methanol is introduced into simultaneously as the third solvent in extraction,
Methanol is still dissolved in aqueous solution, and whole extraction system is divided into biphase.Equally, propose one according to chromatogram and determine extraction
The amount taking methanol in methanol aqueous solution is methanol proportioning=9.408/19.07 × 53%=26.14%, and this data is as basic
Reference, in actual extraction technique, by the concentration of methanol expanded to 29% be in order to reduce extraction times cost-effective while
To increase the dynamics of remove impurity and decolouring.
Still select methanol aqueous solution to carry out dissolution extraction as initial solvent in ultrasonic wave added crystalline portion and obtain Rabdosia rubescens
A prime extractum, the methanol ratio in this operation still carries out a primitive decision by the appearance time of chromatogram.In view of this step
It has been that in purification, final step purpose obtains the rubescensine A that High Purity water rubescensine A is standard substance purity (98%).
So also emphasis considers the retention time (13.94min) of impurity peaks 2 in the calculating of methanol aqueous solution concentration, its result of calculation is
(13.94+9.408)/2/19.07 × 53%=32.44%, according to its result of calculation, finally will be molten for crystallization dissolving in this patent
Agent is set to 33% methanol aqueous solution.
In this embodiment, take full advantage of Jiyuan Rabdosia rubescens plant resourceses, develop new with bar, environmental protection and
The rubescensine A isolating and purifying out high-purity (98%) of suitable industrial mass production, and all can guarantee that in operating unit
The response rate of rubescensine A is more than or equal to 90%.
With reference to specific embodiment, the present invention will be further described, but these embodiments and do not lie in restriction this
The protection domain of invention.
Embodiment 1: the Rabdosia rubescens stem of 5kg and leaf were pulverized 20 mesh sieve, powder is immersed in the dehydrated alcohol of 50l
In, after reflux, extract, 2h at 80 DEG C, filter, filtering residue repeats above operation under the same conditions with the dehydrated alcohol of 50l again.
After extracting solution merges twice, revolving to 1l, remaining for 1l revolving ethanol extract is added 25l water, in 100 DEG C of 2h that flow back,
Afterwards, the quality of the rubescensine A obtaining is the 0.4% of raw material weight.
300ml hp-20 model macroporous resin is packed into the glass chromatography column that a diameter of 3cm height is 100cm, loading
Concentration is 0.5mg/ml, flow velocity 2.5ml/min, and loading volume is 5.2l, after elution flow rate is for 2ml/min washing 2000ml, uses
2000ml volume content is 20% ethanol aqueous wash removing impurities matter, uses 7000ml volume content to be 20% ethanol water eluting afterwards
Rubescensine A product.The response rate is 90%, and product purity is 63.74%.
First, configuration 234ml volume content is 29% methanol aqueous solution, then by ethyl acetate and this methanol aqueous solution
Form three kinds of solution two-phase systems, that is, single extraction liquid volume and resin prepurification obtain containing in extractum after equal-volume mixing
Pure rubescensine A mass ratio be 1:10, and this unit of measuring is l/g.After extraction, collect ethyl acetate phase, rotation
Rubescensine A extractum is obtained after being evaporated.This unit response rate is 93%, and product purity brings up to 78%.
Configuration volume content is 33% methanol aqueous solution, and the extractum obtaining after extraction is dissolved in this methanol aqueous solution
In, the concentration controlling rubescensine A is 50mg/ml, and ultrasonic in subsequent ultrasonic cleaner, ultrasonic temperature is 25 DEG C, when ultrasonic
Between be 20min, the big grain nucleus of white separates out, 6 DEG C of Refrigerator stores 2 days, -8 DEG C of crystallization 12h afterwards.The response rate of this unit is
91%, the purity of the rubescensine A finally obtaining is 97.1%.
Embodiment 2: the Rabdosia rubescens of 5kg were pulverized 20 mesh sieve, powder is immersed in the dehydrated alcohol of 55l, 80
After reflux, extract, 3h at DEG C, filter, filtering residue repeats above operation under the same conditions with the dehydrated alcohol of 55l again.Carry twice
After taking liquid to merge, revolving to 1.1l, remaining for 1.1l revolving ethanol extract is added 27.5l water, in 100 DEG C of 2h that flow back,
Afterwards, the quality of the rubescensine A obtaining is the 0.42% of raw material weight.
300ml hp-20 model macroporous resin is packed into the glass chromatography column that a diameter of 3cm height is 100cm, loading
Concentration is 0.55mg/ml, flow velocity 2.5ml/min, and loading volume is 6l, after elution flow rate is for 2ml/min washing 1800ml, uses
2000ml volume content is 20% ethanol aqueous wash removing impurities matter, uses 9000ml volume content to be 20% ethanol water eluting afterwards
Rubescensine A product.The response rate is 92%, and product purity is 61.74%.
First, configuration 303.6ml volume content is 29% methanol aqueous solution, then will be water-soluble to ethyl acetate and this methanol
Form three kinds of solution two-phase systems, that is, single extraction liquid volume and resin prepurification obtain containing in extractum after the mixing of liquid equal-volume
The pure rubescensine A mass ratio having is 1:10, and this unit measured is l/g.After extraction, collect ethyl acetate phase, rotation
Turn and obtain rubescensine A extractum after being evaporated.This unit response rate is 93.07%, and product purity brings up to 77.45%.
Configuration volume content is 33% methanol aqueous solution, and the extractum obtaining after extraction is dissolved in this methanol aqueous solution
In, the concentration controlling rubescensine A is 48mg/ml, and ultrasonic in subsequent ultrasonic cleaner, ultrasonic temperature is 25 DEG C, when ultrasonic
Between be 20min, the big grain nucleus of white separates out, 4 DEG C of Refrigerator stores 2 days, -8 DEG C of crystallization 11h afterwards.The response rate of this unit is
91%, the purity of the rubescensine A finally obtaining is 98.01%.Mass Spectrometer Method result such as Fig. 4 of this product, this compound
[m-h+]=363.18.
Embodiment 3: the Rabdosia rubescens stem of 5kg and leaf were pulverized 20 mesh sieve, powder is immersed in the dehydrated alcohol of 60l
In, after reflux, extract, 3h at 80 DEG C, filter, filtering residue repeats above operation under the same conditions with the dehydrated alcohol of 60l again.
After extracting solution merges twice, revolving, to 1.2l, remaining for 1.2l revolving ethanol extract is added 30l water, in 100 DEG C of 1h that flow back,
Finally, the quality of the rubescensine A obtaining is the 0.411% of raw material weight.
300ml hp-20 model macroporous resin is packed into the glass chromatography column that a diameter of 3cm height is 100cm, loading
Concentration is 0.6mg/ml, flow velocity 2ml/min, and loading volume is 5.8l, after elution flow rate is for 2.5ml/min washing 1500ml, uses
1700ml volume content is 20% ethanol aqueous wash removing impurities matter, uses 8000ml volume content to be 20% ethanol water eluting afterwards
Rubescensine A product.The response rate is 89.11%, and product purity is 60.74%.
First, configuration 232ml volume content is 29% methanol aqueous solution, then by ethyl acetate and this methanol aqueous solution
Form three kinds of solution two-phase systems, that is, single extraction liquid volume and resin prepurification obtain containing in extractum after equal-volume mixing
Pure rubescensine A mass ratio be 1:15, and this unit of measuring is l/g.After extraction, collect ethyl acetate phase, rotation
Rubescensine A extractum is obtained after being evaporated.This unit response rate is 89.31%, and product purity brings up to 75.02%.
Configuration volume content is 33% methanol aqueous solution, and the extractum obtaining after extraction is dissolved in this methanol aqueous solution
In, the concentration controlling rubescensine A is 50mg/ml, and ultrasonic in subsequent ultrasonic cleaner, ultrasonic temperature is 25 DEG C, when ultrasonic
Between be 20min, the big grain nucleus of white separates out, 6 DEG C of Refrigerator stores 2 days, -8 DEG C of crystallization 12h afterwards.The response rate of this unit is
92.3%, the purity of the rubescensine A finally obtaining is 96.07%.
Embodiment 4: the Rabdosia rubescens stem of 5kg and leaf were pulverized 20 mesh sieve, powder is immersed in the dehydrated alcohol of 50l
In, after reflux, extract, 1h at 80 DEG C, filter, filtering residue repeats above operation under the same conditions with the dehydrated alcohol of 50l again.
After extracting solution merges twice, revolving to 1l, remaining for 1l revolving ethanol extract is added 25l water, in 100 DEG C of 2h that flow back,
Afterwards, the quality of the rubescensine A obtaining is the 0.392% of raw material weight.
300ml hp-20 model macroporous resin is packed into the glass chromatography column that a diameter of 3cm height is 100cm, loading
Concentration is 0.65mg/ml, flow velocity 2ml/min, and loading volume is 5l, after elution flow rate is for 2.5ml/min washing 1500ml, uses
1900ml volume content is 20% ethanol aqueous wash removing impurities matter, uses 8000ml volume content to be 20% ethanol water eluting afterwards
Rubescensine A product.The response rate is 90%, and product purity is 60.74%.
First, configuration 250ml volume content is 29% methanol aqueous solution, then by ethyl acetate and this methanol aqueous solution
Form three kinds of solution two-phase systems, that is, single extraction liquid volume and resin prepurification obtain containing in extractum after equal-volume mixing
Pure rubescensine A mass ratio be 1:13, and this unit of measuring is l/g.After extraction, collect ethyl acetate phase, rotation
Rubescensine A extractum is obtained after being evaporated.This unit response rate is 88.07%, and product purity brings up to 76.45%.
Configuration volume content is 33% methanol aqueous solution, and the extractum obtaining after extraction is dissolved in this methanol aqueous solution
In, the concentration controlling rubescensine A is 49mg/ml, and ultrasonic in subsequent ultrasonic cleaner, ultrasonic temperature is 25 DEG C, when ultrasonic
Between be 19min, the big grain nucleus of white separates out, 4 DEG C of Refrigerator stores 2 days, -8 DEG C of crystallization 12h afterwards.The response rate of this unit is
91.01%, the purity of the rubescensine A finally obtaining is 97.36%.
Embodiment 5: the Rabdosia rubescens stem of 5kg and leaf were pulverized 20 mesh sieve, powder is immersed in the dehydrated alcohol of 65l
In, after reflux, extract, 2h at 80 DEG C, filter, filtering residue repeats above operation under the same conditions with the dehydrated alcohol of 65l again.
After extracting solution merges twice, revolving, to 1.3l, remaining for 1.3l revolving ethanol extract is added 32.5l water, flows back at 100 DEG C
2h, finally, the quality of the rubescensine A obtaining is the 0.421% of raw material weight.
300ml hp-20 model macroporous resin is packed into the glass chromatography column that a diameter of 3cm height is 100cm, loading
Concentration is 0.55mg/ml, flow velocity 2ml/min, and loading volume is 5l, after elution flow rate is for 2ml/min washing 1500ml, uses
1900ml volume content is 20% ethanol aqueous wash removing impurities matter, uses 8000ml volume content to be 20% ethanol water eluting afterwards
Rubescensine A product.The response rate is 90.11%, and product purity is 63.10%.
First, configuration 196.42ml volume content is 29% methanol aqueous solution, then by ethyl acetate and this methanol-water
Form three kinds of solution two-phase systems, that is, single extraction liquid volume and resin prepurification obtain in extractum after the mixing of solution equal-volume
The pure rubescensine A mass ratio containing is 1:14, and this unit measured is l/g.After extraction, collect ethyl acetate phase,
Rotation obtains rubescensine A extractum after being evaporated.This unit response rate is 89.07%, and product purity brings up to 76.15%.
Configuration volume content is 33% methanol aqueous solution, and the extractum obtaining after extraction is dissolved in this methanol aqueous solution
In, the concentration controlling rubescensine A is 53mg/ml, and ultrasonic in subsequent ultrasonic cleaner, ultrasonic temperature is 25 DEG C, when ultrasonic
Between be 18min, the big grain nucleus of white separates out, 4 DEG C of Refrigerator stores 2 days, -8 DEG C of crystallization 12h afterwards.The response rate of this unit is
93.01%, the purity of the rubescensine A finally obtaining is 96.16%.
Embodiment 6: the Rabdosia rubescens stem of 5kg and leaf were pulverized 20 mesh sieve, powder is immersed in the dehydrated alcohol of 60l
In, after reflux, extract, 2h at 80 DEG C, filter, filtering residue repeats above operation under the same conditions with the dehydrated alcohol of 60l again.
After extracting solution merges twice, revolving, to 1.2l, remaining for 1.2l revolving ethanol extract is added 30l water, in 100 DEG C of 2h that flow back,
Finally, the quality of the rubescensine A obtaining is the 0.4203% of raw material weight.
40l hp-20 model macroporous resin is packed into the glass chromatography column that a diameter of 12cm height is 2m, sample concentration
For 1.2mg/ml, flow velocity 320ml/min, loading time is 11h, and elution flow rate is 300ml/min, after washing 200l, uses 280l
Volume content is 20% ethanol aqueous wash removing impurities matter, uses 1200l volume content to be 20% ethanol water eluting Rabdosia rubescens afterwards
A prime product.The response rate is 91.21%, and product purity is 59.17%.
First, configuration 21.12l volume content is 29% methanol aqueous solution, then will be water-soluble to ethyl acetate and this methanol
Form three kinds of solution two-phase systems, that is, single extraction liquid volume and resin prepurification obtain containing in extractum after the mixing of liquid equal-volume
The pure rubescensine A mass ratio having is 1:12, and this unit measured is l/g.After extraction, collect ethyl acetate phase, rotation
Turn and obtain rubescensine A extractum after being evaporated.This unit response rate is 90.07%, and product purity brings up to 75.45%.
Configuration volume content is 33% methanol aqueous solution, and the extractum obtaining after extraction is dissolved in this methanol aqueous solution
In, the concentration controlling rubescensine A is 48mg/ml, and ultrasonic in subsequent ultrasonic cleaner, ultrasonic temperature is 25 DEG C, when ultrasonic
Between be 20min, the big grain nucleus of white separates out, 4 DEG C of Refrigerator stores 2 days, -8 DEG C of crystallization 11h afterwards.The response rate of this unit is
90.07%, the purity of the rubescensine A finally obtaining is 98.%.
Embodiment 7: the Rabdosia rubescens stem of 5kg and leaf were pulverized 20 mesh sieve, powder is immersed in the dehydrated alcohol of 50l
In, after reflux, extract, 1h at 80 DEG C, filter, filtering residue repeats above operation under the same conditions with the dehydrated alcohol of 50l again.
After extracting solution merges twice, revolving to 1l, remaining for 1l revolving ethanol extract is added 25l water, in 100 DEG C of 1h that flow back,
Afterwards, the quality of the rubescensine A obtaining is the 0.396% of raw material weight.
40l hp-20 model macroporous resin is packed into the glass chromatography column that a diameter of 12cm height is 2m, sample concentration
For 1.2mg/ml, flow velocity 310ml/min, loading time is 11.5h, and elution flow rate is 320ml/min, after washing 240l, uses
280l volume content is 20% ethanol aqueous wash removing impurities matter, uses 1200l volume content to be 20% ethanol water eluting winter afterwards
LINGCAO A prime product.The response rate is 90.01%, and product purity is 58.17%.
First, configuration 23.33l volume content is 29% methanol aqueous solution, then will be water-soluble to ethyl acetate and this methanol
Form three kinds of solution two-phase systems, that is, single extraction liquid volume and resin prepurification obtain containing in extractum after the mixing of liquid equal-volume
The pure rubescensine A mass ratio having is 1:11, and this unit measured is l/g.After extraction, collect ethyl acetate phase, rotation
Turn and obtain rubescensine A extractum after being evaporated.This unit response rate is 90.07%, and product purity brings up to 76.17%.
Configuration volume content is 33% methanol aqueous solution, and the extractum obtaining after extraction is dissolved in this methanol aqueous solution
In, the concentration controlling rubescensine A is 52mg/ml, and ultrasonic in subsequent ultrasonic cleaner, ultrasonic temperature is 25 DEG C, when ultrasonic
Between be 17min, the big grain nucleus of white separates out, 4 DEG C of Refrigerator stores 2 days, -8 DEG C of crystallization 11h afterwards.The response rate of this unit is
90.07%, the purity of the rubescensine A finally obtaining is 96.99%.
Embodiment 8: the Rabdosia rubescens stem of 5kg and leaf were pulverized 20 mesh sieve, powder is immersed in the dehydrated alcohol of 55l
In, after reflux, extract, 2h at 80 DEG C, filter, filtering residue repeats above operation under the same conditions with the dehydrated alcohol of 55l again.
After extracting solution merges twice, revolving, to 1.1l, remaining for 1.1l revolving ethanol extract is added 27.5l water, flows back at 100 DEG C
2h, finally, the quality of the rubescensine A obtaining is the 0.424% of raw material weight.
40l hp-20 model macroporous resin is packed into the glass chromatography column that a diameter of 12cm height is 2m, sample concentration
For 1.5mg/ml, flow velocity 350ml/min, loading time is 12h, and elution flow rate is 400ml/min, after washing 200l, uses 200l
Volume content is 20% ethanol aqueous wash removing impurities matter, uses 900l volume content to be 20% ethanol water eluting Rabdosia rubescens first afterwards
Plain product.The response rate is 87.01%, and product purity is 55.17%.
First, configuration 14.62l volume content is 29% methanol aqueous solution, then will be water-soluble to ethyl acetate and this methanol
Form three kinds of solution two-phase systems, that is, single extraction liquid volume and resin prepurification obtain containing in extractum after the mixing of liquid equal-volume
The pure rubescensine A mass ratio having is 1:15, and this unit measured is l/g.After extraction, collect ethyl acetate phase, rotation
Turn and obtain rubescensine A extractum after being evaporated.This unit response rate is 88.07%, and product purity brings up to 74.17%.
Configuration volume content is 33% methanol aqueous solution, and the extractum obtaining after extraction is dissolved in this methanol aqueous solution
In, the concentration controlling rubescensine A is 53mg/ml, and ultrasonic in subsequent ultrasonic cleaner, ultrasonic temperature is 25 DEG C, when ultrasonic
Between be 18min, the big grain nucleus of white separates out, 6 DEG C of Refrigerator stores 2 days, -8 DEG C of crystallization 11h afterwards.The response rate of this unit is
90%, the purity of the rubescensine A finally obtaining is 96.03%.
Embodiment 9: the Rabdosia rubescens stem of 5kg and leaf were pulverized 20 mesh sieve, powder is immersed in the dehydrated alcohol of 55l
In, after reflux, extract, 2h at 80 DEG C, filter, filtering residue repeats above operation under the same conditions with the dehydrated alcohol of 55l again.
After extracting solution merges twice, revolving, to 1.1l, remaining for 1.1l revolving ethanol extract is added 27.5l water, flows back at 100 DEG C
2h, finally, the quality of the rubescensine A obtaining is the 0.427% of raw material weight.
40l hp-20 model macroporous resin is packed into the glass chromatography column that a diameter of 12cm height is 2m, sample concentration
For 1mg/ml, flow velocity 300ml/min, loading time is 12h, and elution flow rate is 300ml/min, after washing 200l, uses 240l body
Long-pending content is 20% ethanol aqueous wash removing impurities matter, uses 1200l volume content to be 20% ethanol water eluting Rabdosia rubescens first afterwards
Plain product.The response rate is 92.13%, and product purity is 61.11%.
First, configuration 21.6l volume content is 29% methanol aqueous solution, then by ethyl acetate and this methanol aqueous solution
Form three kinds of solution two-phase systems, that is, single extraction liquid volume and resin prepurification obtain containing in extractum after equal-volume mixing
Pure rubescensine A mass ratio be 1:10, and this unit of measuring is l/g.After extraction, collect ethyl acetate phase, rotation
Rubescensine A extractum is obtained after being evaporated.This unit response rate is 93.03%, and product purity brings up to 77.78%.
Configuration volume content is 33% methanol aqueous solution, and the extractum obtaining after extraction is dissolved in this methanol aqueous solution
In, the concentration controlling rubescensine A is 48mg/ml, and ultrasonic in subsequent ultrasonic cleaner, ultrasonic temperature is 25 DEG C, when ultrasonic
Between be 20min, the big grain nucleus of white separates out, 4 DEG C of Refrigerator stores 2 days, -8 DEG C of crystallization 12h afterwards.The response rate of this unit is
90.01%, the purity of the rubescensine A finally obtaining is 98.02%.
Embodiment 10: the Rabdosia rubescens stem of 5kg and leaf were pulverized 20 mesh sieve, powder is immersed in the dehydrated alcohol of 65l
In, after reflux, extract, 2h at 80 DEG C, filter, filtering residue repeats above operation under the same conditions with the dehydrated alcohol of 65l again.
After extracting solution merges twice, revolving, to 1.3l, remaining for 1.3l revolving ethanol extract is added 32.5l water, flows back at 100 DEG C
2h, finally, the quality of the rubescensine A obtaining is the 0.421% of raw material weight.
40l hp-20 model macroporous resin is packed into the glass chromatography column that a diameter of 12cm height is 2m, sample concentration
For 1.4mg/ml, flow velocity 330ml/min, loading time is 12.5h, and elution flow rate is 380ml/min, after washing 280l, uses
280l volume content is 20% ethanol aqueous wash removing impurities matter, uses 10500l volume content to be 20% ethanol water eluting winter afterwards
LINGCAO A prime product.The response rate is 89.83%, and product purity is 58.21%.
First, configuration 38.5l volume content is 29% methanol aqueous solution, then by ethyl acetate and this methanol aqueous solution
Form three kinds of solution two-phase systems, that is, single extraction liquid volume and resin prepurification obtain containing in extractum after equal-volume mixing
Pure rubescensine A mass ratio be 1:9, and this unit of measuring is l/g.After extraction, collect ethyl acetate phase, rotation
Rubescensine A extractum is obtained after being evaporated.This unit response rate is 93.03%, and product purity brings up to 77.80%.
Configuration volume content is 33% methanol aqueous solution, and the extractum obtaining after extraction is dissolved in this methanol aqueous solution
In, the concentration controlling rubescensine A is 51mg/ml, and ultrasonic in subsequent ultrasonic cleaner, ultrasonic temperature is 25 DEG C, when ultrasonic
Between be 15min, the big grain nucleus of white separates out, 5 DEG C of Refrigerator stores 2 days, -8 DEG C of crystallization 12h afterwards.The response rate of this unit is
90.64%, the purity of the rubescensine A finally obtaining is 97.04%.
Claims (5)
1. a kind of method preparing high-purity rubescensine A using Rabdosia rubescens is it is characterised in that comprise the steps:
1) extraction process twice of rubescensine A
First have to through pulverizing for the Rabdosia rubescens stem in this technological design and leaf, its ground product carries out two kinds of solvent extractions, first
First, dehydrated alcohol reflux, extract, extraction time is 1-3h, and the volume ratio extracting raw materials quality with Extraction solvent is 1:10-13, should
The unit measured is g/ml；Extracting temperature is 80 DEG C, and after extracting twice, united extraction liquid rotary evaporation is former to extracting liquid volume
The 1/100 of extracting liquid volume；Add water in extractor, its volume is the half of ethanol amount used, at 100 DEG C, reflux, extract, 1-
3h；
2) hp-20 macroporous adsorbent resin industry prepurification experimental design
Provide the macroporous resin column chromatography experiment of two kinds of scales, that is, the bench scale experiment of rubescensine A and pilot-scale are real
Test, according to scale selection one；Specific as follows:
Diameter for the glass packed column of bench scale and height are respectively 3cm and 100cm, hp-20 model macroporous resin
Packing volume is 300ml, and sample concentration is 0.5-0.65mg/ml, flow velocity 2-3.5ml/min, and loading volume is 5-6l；Eluting stream
Speed is 2-3.5ml/min, after washing 1500-2000ml, the ethanol elution being 20% with volume content, and front 1500-2000ml uses
In remove impurity, with being followed by the eluent that 7000-9000ml contains rubescensine A；
The diameter of the chromatographic column of pilot-scale and height are respectively 12cm and 2m；The hp-20 macroporous resin of 40l is packed into pillar
In, control sample solution concentration scope is 1-1.5mg/ml, flow rates 300-350ml/min of loading, and loading time is 11-
13h；In elution step, flow velocity is 300-400ml/min, after the water elution of 200-280l, in the volume content with 200-280l
For 20% ethanol water remove impurity, finally, it is that 20% ethanol solution is used for eluting winter icepro with the volume content of 900-1200l
Careless A prime；
3) three kinds of solvents, it may be assumed that acetate-methanol-aqueous solution, extract decolouring remove impurity further
First, configuration volume content is 29% methanol aqueous solution, then mixes ethyl acetate and this methanol aqueous solution equal-volume
Form three kinds of solution two-phase systems after conjunction；The pure winter that single extraction liquid volume and resin prepurification obtain containing in extractum insults
Careless A prime mass ratio is 1:9-15, and the unit that this is measured is l/g；After extraction, collect ethyl acetate phase, rotation obtains the winter after being evaporated
LINGCAO A prime extractum；
4) ultrasonic assistant crystallisation by cooling obtains the crystal of rubescensine A
Configuration volume content is 33% methanol aqueous solution, the extractum obtaining is dissolved in this methanol aqueous solution, control after extraction
The concentration of rubescensine A processed is 45-53mg/ml, ultrasonic in subsequent ultrasonic cleaner, and ultrasonic temperature is 25 DEG C, ultrasonic time
For 15-20min, the big grain nucleus of white separates out, 4-6 DEG C of Refrigerator store 2 days, -8 DEG C of crystallization 10-12h afterwards；Centrifugation obtains solid
Crystalline product, with the water washing product of 2l twice, centrifugation after being statically placed in 2h in -8 DEG C of crystallizer respectively every time obtains white powder
End, drying machine drying obtains rubescensine A powder.
2. method according to claim 1 is it is characterised in that step 1) extract the volume ratio of raw materials quality and Extraction solvent
For 1:11, the unit that this is measured is g/ml, and the extraction time of ethanol is 2h, and the extraction time of water is also 2h.
3. method according to claim 1 is it is characterised in that step 2) in the technique of bench scale, sample solution concentration is
0.55mg/ml, flow velocity is 2.5ml/min, and loading volume is 6l；Elution flow rate is 2ml/min, and the volume of water lotion is
1800ml, is remove impurity with 2000ml volume content for 20% ethanol water volume, with the volume content of 9000ml is subsequently
20% ethanol water collects the rubescensine A product that prepurification obtains；Step 2) in pilot-scale technique, sample solution concentration
For 1mg/ml, loading flow velocity is 300ml/min, and loading time is 12h, and elution flow rate is 300ml/min；The volume of water lotion
200l, is that 20% ethanol water is used for remove impurity with 240l volume content, subsequently, is 20% ethanol with the volume content of 1200l
Aqueous solution collects the rubescensine A product that prepurification obtains.
4. method according to claim 1 is it is characterised in that step 3) single extraction liquid volume obtained with resin prepurification
The pure rubescensine A mass ratio containing in extractum is 1:10, and the unit that this is measured is l/g.
5. method according to claim 1 is it is characterised in that step 4) extractum that will obtain after extraction is dissolved in volume and contains
Measure as in 33% methanol, forming the rubescensine A supersaturated solution that concentration is 48mg/ml, be positioned in ultrasonic reactor
Ultrasonic time 20min；After a large amount of crystal suction out, 4 DEG C of Refrigerator stores 2 days, -8 DEG C of crystallization 12h afterwards.
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| CN110092796B (en) * | 2018-01-27 | 2021-04-09 | 南京工业大学 | Method for extracting and separating oridonin |
| CN116003428A (en) * | 2022-11-28 | 2023-04-25 | 常州大学 | Method for extracting and synchronously separating oridonin and rosmarinic acid |
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| CN101817831A (en) * | 2009-12-23 | 2010-09-01 | 南京泽朗医药科技有限公司 | Method for extracting oridonin from rabdosia rubescens and purifying oridonin |
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