CN103610708B - The preparation technology of low acid high-purity terpene lactones extract in a kind of Cortex Ginkgo - Google Patents
The preparation technology of low acid high-purity terpene lactones extract in a kind of Cortex Ginkgo Download PDFInfo
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Abstract
The invention discloses the preparation technology of low acid high-purity terpene lactones extract in a kind of Cortex Ginkgo, with Cortex Ginkgo as raw material, size-reduced to coarse powder, the ethanol extraction of high concentration, concentrating, dilute, through polycaprolactam adsorption and desorption by resin, eluent concentrates, ethyl alcohol recrystallization, the coarse crystallization obtained separates through high performance liquid chromatography, prepares terpene lactones extract, its total lactones content >=95%, total ginkgolic acids content≤1ppm.The present invention overcomes existing production technology defect, there is the features such as stable processing technique is controlled, easy and simple to handle, product quality is high and stablizes, finished product yield is high, production cost is relatively low, and Cortex Ginkgo can be turned waste into wealth, give full play to its economic worth.
Description
Technical field
The present invention relates to the preparation technology of low acid high-purity terpene lactones extract in a kind of Cortex Ginkgo, belong to Chinese medicine preparation
Technical field.
Background technology
Folium Ginkgo terpene lactones is distinctive important activity compound in a class Folium Ginkgo and Cortex Ginkgo, by sesquiterpene lactones and
Diterpenoid-lactone forms, and main component includes ginkalide A, ginkalide B, ginkalide C, bilobalide J and bilobalide.Silver
Fructus Pruni acid (GA) is the toxic and side effects composition in Folium Ginkgo extract, has the effects such as sensitization, cytotoxicity and immunotoxicity,
Be there is potential hazard in human health, be primarily present in Folium Ginkgo, ginkgo nut and Cortex Ginkgo；Germany started tight in 1997
In lattice restriction gingko leaf preparation, GA level is at below 5ppm, and European Pharmacopoeia has continued to use the GA bound requirements of 5ppm in GBE standard,
Chinese Pharmacopoeia version in 2010 also limits GA content in GBE should be at below 10ppm.
Folium Ginkgo terpene lactones has suppression platelet aggregation, inhibition thrombosis, protection vascular endothelial cell, expands crown moving
Arteries and veins etc. act on, for strong platelet activating factor (PAF) antagonist.In bilobalide, each lactone role is different,
The wherein PAF(platelet activating factor of ginkalide B) the activity of the anti-PAF of selectivity the strongest, be secondly ginkalide A and silver
Fructus Pruni lactone C；Ginkalide A has angst resistance effect, ginkalide B and C the most not to have angst resistance effect；Bilobalide is neural
System, psychotic medicine, to age and the moronism phenomenon occurred has unusual curative effect, be also used for treat neuropathy, encephalopathy
And myelopathy, symptom includes: paraesthesia, collapses from physical exhaustion or peralytic dementia, improper neural reflex, amyotrophy, muscle spasm,
Tremble, superficiality or the imbalance of degree of depth sensitivity, to have a headache and extremity pain, language is lacked of proper care, vision and audition imbalance, profound dizzy, neural mistake
It is in harmonious proportion and lacks centrality, hypomnesis and disorientation etc..
Folium Ginkgo terpene lactones extract, in addition to as pharmaceutical raw material, is the most also largely used to health product and food
Exploitation, is used, therefore, in recent years, to terpene on domestic and international market in a large number as a kind of excellent dietary supplement abroad
The demand of lactone extract is continuously increased.And the terpene lactones extract of the overwhelming majority derives from Folium Ginkgo in the market, for
In Cortex Ginkgo, the exploitation of lactone extract is less.
Owing in Determination of ginkgolides relatively Cortex Ginkgo, content is high, and Terpene Lactones in Extract Ginkgo biloba L content reaches
6-12%, therefore the preparation of current most of terpene lactones extract isolateds from Folium Ginkgo or Folium Ginkgo extract are relevant
Document report is also a lot, but the cost of material of Folium Ginkgo or extract is higher.Owing in Cortex Ginkgo, terpene lactones total content is only
About 0.1-0.2%, is typically regarded as waste disposal by common people, and on market, the terpene lactones extract price of purity >=90% is number
Ten thousand to ten ten thousand yuan of per kilograms, prepare high-purity terpene lactones extract with cheap Cortex Ginkgo for raw material industrialization and have relatively
Big potential market.
Through retrieval, document and the patent prepared about Cortex Ginkgo terpene lactones extract at present are less, such as document " Semen Ginkgo
Terpene lactones Study on extraction in root bark " in only investigated root bark lactone content measure Extraction technique, the biggest production
Technique.The preparation technology of part research report uses water, alkaline soak or reflux, extract, such as patent 97107809.2 " Semen Ginkgo
The extracting method of lactone and the preparation containing bilobalide ", 201110071505.3 " the Hydrolysis kinetics sides of a kind of bilobalide
Method " and 201210116022.5 " extracting separating bilobalide A, B, C, J, M and the technique of bilobalide ", due to Folium Ginkgo terpene lactones
Polarity is less, is insoluble in water, is soluble in the organic solvent such as ethanol, methanol, therefore uses the lactone rate of transform of extraction process by water to be far below
Alcohol extraction process, extraction efficiency is relatively low；And potass extraction also can destroy the bilobalide that wherein content is higher.Part research also has pin
Separation to wherein GA, GC monomer, such as patent 201010294667.9 " a kind of extraction ginkalide A, C from ginkgo root bark
Processing technology " and 201110067186.9 " from Cortex Ginkgo separate, the methods of purification ginkalide C ", monomer preparation point
From technique relatively complicated, have lost other terpene lactones compositions simultaneously, production cost far above mixing lactone preparation cost,
Big production uses organic solvent extraction higher to producing equipment requirements, and safety exists certain hidden danger, and lactone GA, GC monomer is opened
The market demand that the market demand sent out can not show a candle to lactone extract is big, is not suitable for being prepared on a large scale.
Summary of the invention
It is an object of the invention to: utilize cheap Cortex Ginkgo raw material, it is provided that a kind of stable processing technique is controlled, operation
The preparation technology of the high-purity Folium Ginkgo terpene lactones easy, finished product rate of transform height, product quality are high and stable, production cost is relatively low,
Cortex Ginkgo is turned waste into wealth, gives full play to its economic worth.
To achieve these goals, the technical solution used in the present invention includes:
The invention provides the preparation technology of low acid high-purity terpene lactones extract in a kind of Cortex Ginkgo, with Cortex Ginkgo
For raw material, Cortex Ginkgo is pulverized, and adds ethanol solution and extracts；Extracting solution concentrates, and dilute is washed through polycaprolactam resin absorption
De-；Collect absorption residual liquid and water elution liquid, concentrate, use ethyl alcohol recrystallization；Separate through high performance liquid chromatography, obtain terpene lactones and extract
Thing, its total lactones content >=95%, total ginkgolic acids content≤1ppm, the finished product rate of transform is high, and technique perseverance stability is good.
The present invention specifically comprises the following steps that
Step 1, ethanol extraction: take the Cortex Ginkgo after pulverizing, the mass fraction adding 10-15 times amount is 60-80% ethanol water
Solution reflux, extract, 2-3 time, extracting solution is concentrated into without alcohol, obtains concentrated solution；Wherein ethanol content ＜ 5%.
Owing in root bark, fibre composition is more, degree of grinding difference can directly affect extraction efficiency, the most of the present invention
Pulverizing after root bark be clearly: be crushed to coarse powder, i.e. cross 24 mesh sieves.
The 60-80% ethanol water reflux, extract, of described 10-15 times amount 2-3 time, optimum condition is by 12 times amount
70% ethanol water heating and refluxing extraction 3 times.
Step 2, polycaprolactam resin purification: concentrated solution adds purified water and is diluted to density and is 1.0-1.1g/mL(50 DEG C),
Upper polycaprolactam resin, adds the water elution of 3-4 times of column volume, collects absorption residual liquid and water elution liquid, concentrates, obtains thick paste.
It is 1.01-1.03 g/mL(50 DEG C that described upper prop liquid is preferably diluted to density).
Described polyamide granularity is 100-200 mesh.
The consumption optimum condition of described washing is the purified water eluting adding 3 times of column volumes.
Gained thick paste density is 1.2-1.5 g/mL(50 DEG C), optimum condition is 1.3-1.4 g/mL.
Step 3, the preparation of coarse crystallization: it is 20-40% that thick paste adds a certain amount of ethanol to solution concentration, and 60 DEG C of water-baths add
Heat makes it be completely dissolved, and filters, and filtrate puts refrigerator cold-storage, recrystallization；After crystallization, mother solution repeats operation, obtains coarse crystallization；
Described ethanol water optimum condition is 30% ethanol water.
Described refrigerator cold-storage condition is 0-4 DEG C, preserves 8-12h；Preferably recrystallization refrigerator cold-storage condition is 0-2 DEG C.
Preferably mother solution recrystallization number of times is 3 times.
Step 4, preparative separation: coarse crystallization proper amount of methanol water dissolution, separate through high performance liquid chromatography, repeat sample introduction, close
And interior esteratic site fraction, concentrating under reduced pressure, it is dried, obtains the terpene lactones extract of purity >=95%.
Described proper amount of methanol water dissolution, optimum condition is to add the methanol aqueous solution that mass fraction is 60-80%, tepidarium
Heating so that it is be in supersaturation dissolved state.
Described high performance liquid chromatography separates, and optimum condition is for using C18 preparative hplc post, and flowing is 30-50% first mutually
Alcohol-water, ultraviolet detection wavelength is 218nm, and flow velocity is 200-500mL/min, and sample size is 50-100mL/ time, repeats sample introduction, receives
Five lactone fractions between collection BB to GB.
One of the preferred drying under reduced pressure of described drying mode, lyophilization or microwave drying.
In Cortex Ginkgo of the present invention, the preparation technology of low acid high-purity terpene lactones extract, uses 60-80% second in step 1
Alcohol-water solution is as Extraction solvent, in the case of ensureing that lactone extracts completely, has abandoned the entrance of the big polar component of part, has subtracted
Having lacked interference, this is also that research technique need not one of principal element using organic solvent extraction.
Step 2 uses polycaprolactam resin to be purified, and can remove part liposoluble constituent, to reduce its counterweight knot
The interference of brilliant process, has especially carried out effective removal to the known toxicity composition ginkgoic acid in root bark, for ensureing product matter
Amount safety serves good control action.
Step 3 by the recrystallization for several times of low alcoholic degree ethanol, the total lactones rate of transform in gained coarse crystallization reach 80% with
On, total lactones content reaches about 95%, has reached good recrystallization effect.
Step 4 uses high performance liquid chromatography to separate, and collects at the lactone fraction of 5 interior compositions from BB to GB, separates and want
Ask just much lower more than separating monomer, the repeatable recycling of mobile phase methanol-water of employing, significantly reduce and produce into
This, preparation amount can reach the production requirement of more than feather weight, meets production expection.
In a kind of Cortex Ginkgo that the present invention proposes, the preparation technology of low acid high-purity terpene lactones extract, has the most excellent
Point:
1. the high-purity Folium Ginkgo terpene lactones extract produced by the present invention, total lactones content >=95%, total ginkgolic acids content
≤ 1ppm, product quality is high and stable；
2. the finished product rate of transform of the present invention is high, as the total lactones rate of transform reaches more than 80%, total lactones content reach 95% with
On；
3. the inventive method need not organic solvent extraction, has production technology safe and stable controlled, easy and simple to handle, raw
Product cost is relatively low, good in economic efficiency advantage.
(4) specific embodiments:
The following examples, are used for further illustrating and describing the present invention, but are not meant to that the present invention shows fully in this.Real
Execute the most concrete numerical value that value in example is scope of the present invention, be and can implement.
The bilobalide content assaying method that this research uses is shown in the relevant item of " Chinese Pharmacopoeia " Folium Ginkgo extract；High
The chromatographic condition of effect liquid phase separation is as follows:
Chromatographic column: Agilent C18 pursuit preparative hplc post；
Flowing phase: 30-50% methanol-water；
Ultraviolet detection wavelength: 218nm；
Flow velocity: 200-500mL/min；
Sample size: 50-100mL/ time.
Embodiment 1
Cortex Ginkgo, roguing, it is crushed to coarse powder (crossing 24 mesh sieves), takes Cortex Ginkgo coarse powder 100kg, adding mass fraction is
The ethanol 1000kg of 60%, heating and refluxing extraction 2 times, merge twice extracting solution, be evaporated to without alcohol that (ethanol content is less than
5%), concentrated solution is obtained；Being diluted with water to 50 DEG C of lower densities is 1.0g/mL, 100 mesh polycaprolactam resin absorption on diluent, uses
The purified water eluting of 3 times of column volumes, collects absorption residual liquid and water elution liquid, is evaporated to density 1.25g/mL(50 DEG C),
Thick paste；Adding a certain amount of ethanol to solution concentration is 20%, and 60 DEG C of heating in water bath make it be completely dissolved, and filters, and filtrate is put rapidly
Refrigerator cold-storage 8h, recrystallization, its refrigerator cold-storage temperature is 0-4 DEG C；After recrystallization, mother solution is again according to above-mentioned recrystallization method repeatedly
Recrystallization 3 times, merges all crystallizations, obtains coarse crystallization；Coarse crystallization separates through high performance liquid chromatography, repeats sample introduction, merges and collects BB
Five lactone fractions between GB, concentrate, drying under reduced pressure (60 DEG C/0.08MPa), obtain high-purity Folium Ginkgo terpene lactones extract.Produce
The product total lactones rate of transform is 80.7%, and total lactones content is 96.2%, and total ginkgolic acids content is 0.52ppm.
Embodiment 2
Take Cortex Ginkgo coarse powder 100kg, add 80% ethanol 1200kg, heating and refluxing extraction 3 times, merge twice extracting solution,
Being evaporated to without alcohol, being diluted with water to 50 DEG C of lower densities is 1.05g/mL, and on diluent, 200 mesh polycaprolactam resins are inhaled
Attached, with the purified water eluting of 4 times of column volumes, collect absorption residual liquid and water elution liquid, be evaporated to density 1.42g/mL(50
DEG C), adding a certain amount of ethanol to solution concentration is 40%, and 60 DEG C of heating in water bath make it be completely dissolved, and filters, and filtrate is put rapidly
Refrigerator cold-storage 12h, recrystallization.After recrystallization, mother solution recrystallization 3 times the most repeatedly, merge all crystallizations, obtain coarse crystallization.Coarse crystallization warp
High performance liquid chromatography separates, and repeats sample introduction, merges five the lactone fractions collected between BB to GB, concentrates, drying under reduced pressure, obtains high-purity
Degree Folium Ginkgo terpene lactones extract.The total lactones rate of transform is 86.1%, and total lactones content is 97.1%, and total ginkgolic acids content is
0.37ppm。
Embodiment 3
Take Cortex Ginkgo coarse powder 500kg, add 70% ethanol 7500kg, heating and refluxing extraction 3 times, merge twice extracting solution,
Being evaporated to without alcohol, being diluted with water to 50 DEG C of lower densities is 1.10g/mL, and on diluent, 300 mesh polycaprolactam resins are inhaled
Attached, with the purified water eluting of 4 times of column volumes, collect absorption residual liquid and water elution liquid, be evaporated to density 1.31g/mL(50
DEG C), adding a certain amount of ethanol to solution concentration is 30%, and 60 DEG C of heating in water bath make it be completely dissolved, and filters, and filtrate is put rapidly
Refrigerator cold-storage 10h, recrystallization.After recrystallization, mother solution recrystallization 3 times the most repeatedly, merge all crystallizations, obtain coarse crystallization.Coarse crystallization warp
High performance liquid chromatography separates, and repeats sample introduction, merges five the lactone fractions collected between BB to GB, concentrates, drying under reduced pressure (60 DEG C/
0.08MPa), high-purity Folium Ginkgo terpene lactones extract is obtained.The total lactones rate of transform is 84.3%, and total lactones content is 95.8%, always silver
Fructus Pruni acid content is 0.69ppm.
Embodiment 4
Take Cortex Ginkgo coarse powder 500kg, add 75% ethanol 6000kg, heating and refluxing extraction 3 times, merge twice extracting solution,
Being evaporated to without alcohol, being diluted with water to 50 DEG C of lower densities is 1.04g/mL, and on diluent, 100 mesh polycaprolactam resins are inhaled
Attached, with the purified water eluting of 4 times of column volumes, collect absorption residual liquid and water elution liquid, be evaporated to density 1.29g/mL(50
DEG C), adding a certain amount of ethanol to solution concentration is 30%, and 60 DEG C of heating in water bath make it be completely dissolved, and filters, and filtrate is put rapidly
Refrigerator cold-storage 10h, recrystallization.After recrystallization, mother solution recrystallization 3 times the most repeatedly, merge all crystallizations, obtain coarse crystallization.Coarse crystallization warp
High performance liquid chromatography separates, and repeats sample introduction, merges five the lactone fractions collected between BB to GB, concentrates, drying under reduced pressure, obtains high-purity
Degree Folium Ginkgo terpene lactones extract.The total lactones rate of transform is 85.3%, and total lactones content is 96.4%, and total ginkgolic acids content is
0.28ppm。
Embodiment 5
Take Cortex Ginkgo coarse powder 500kg, add 75% ethanol 5500kg, heating and refluxing extraction 3 times, merge twice extracting solution,
Being evaporated to without alcohol, being diluted with water to 50 DEG C of lower densities is 1.07g/mL, and on diluent, 200 mesh polycaprolactam resins are inhaled
Attached, with the purified water eluting of 4 times of column volumes, collect absorption residual liquid and water elution liquid, be evaporated to density 1.35g/mL(50
DEG C), adding a certain amount of ethanol to solution concentration is 30%, and 60 DEG C of heating in water bath make it be completely dissolved, and filters, and filtrate is put rapidly
Refrigerator cold-storage 10h, recrystallization.After recrystallization, mother solution recrystallization 3 times the most repeatedly, merge all crystallizations, obtain coarse crystallization.Coarse crystallization warp
High performance liquid chromatography separates, and repeats sample introduction, merges five the lactone fractions collected between BB to GB, concentrates, drying under reduced pressure (60 DEG C/
0.08MPa), high-purity Folium Ginkgo terpene lactones extract is obtained.The total lactones rate of transform is 84.6%, and total lactones content is 95.8%, always silver
Fructus Pruni acid content is 0.74ppm.
Embodiment 6
Survey according to the preparation method of number of patent application 201110071505.3 " a kind of Hydrolysis kinetics method of bilobalide "
Customize to obtain the rate of transform of finished product, the content of lactone.Specific as follows:
Take after Cortex Ginkgo is pulverized and cross 40 mesh sieves, weigh 50kg, add sodium acetate solution 200L, soak 3 hours, filter, abandon
Go filtrate, obtain filtering residue；Filtering residue adds 50-70 DEG C of hot water extraction 3 times, adds hot water 300L every time, and extraction time is 4 hours/time, mistake
Filter, obtains lixiviating solution；Lixiviating solution is concentrated into the 1/10 of cumulative volume, obtains concentrated solution；Concentrated solution 95% ethanol water of 4 times amount
Dissolve, stir 40min, filter, filtrate recycling ethanol, to alcoholic degree ＜ 5%, obtain without alcohol concentrated solution；Concentrated solution ethyl acetate extracts
Taking 3 times, ethyl acetate is 1:2 with the ratio of concentrated solution, combining extraction liquid；Extract concentrates, drying under reduced pressure (60 DEG C/
0.08MPa), lactone extract is obtained.Recording total lactones content is 78.4%, and the total lactones rate of transform is 56.8%.Result shows, should
It is relatively low that method prepares the lactone extract rate of transform, and total lactones content is the highest.
Claims (7)
1. a preparation technology for low acid high-purity terpene lactones extract in Cortex Ginkgo, is former with size-reduced Cortex Ginkgo
Material, adds ethanol solution and extracts；Extracting solution concentrates, and dilute, through polycaprolactam adsorption and desorption by resin；Collect absorption residual liquid and
Water elution liquid, concentrates, adds ethanol solution recrystallization；Separate through high performance liquid chromatography again, obtain low acid high-purity terpene lactones and extract
Thing, its total lactones content >=95%, total ginkgolic acids content≤1ppm；Concrete preparation process is as follows: 1) take the Radix Ginkgo after pulverizing
Skin, adds 60-80% ethanol water reflux, extract, 2-3 time, and extracting solution is concentrated into without alcohol, obtains concentrated solution；2) concentrated solution adds purified water
Being diluted to 50 DEG C of lower densities is 1.0-1.1g/mL, upper polycaprolactam resin, washing, collects absorption residual liquid and water elution liquid, dense
Contracting, obtains thick paste；3) thick paste adds ethanol to solution concentration is 20-40%, and 60 DEG C of heating in water bath make it be completely dissolved, and filter, filtrate
Put refrigerator cold-storage, recrystallization；Mother liquor concentrations after crystallization, then with 30% ethanol water recrystallization of 20-30 times amount, operate 3 times,
Obtain coarse crystallization；4) coarse crystallization proper amount of methanol water dissolution, separates through high performance liquid chromatography, repeats sample introduction, and in merging, esteratic site evaporates
Point, concentrating under reduced pressure, it is dried, obtains the low acid terpene lactones extract of purity >=95%.
Preparation technology the most according to claim 1, is characterized in that the 60-80% ethanol water described in step 1) is: often public
Jin Cortex Ginkgo adds the 60-80% ethanol water of 10-15 times, reflux, extract,.
Preparation technology the most according to claim 1, is characterized in that being concentrated into described in step 1) without alcohol is: be concentrated into ethanol
Content is less than 5%.
Preparation technology the most according to claim 1, is characterized in that step 2) described in polyamide granularity be 100-200
Mesh；The consumption of described washing is 3-4 times of column volume；Described thick paste be 50 DEG C of lower densities be 1.2-1.5 g/mL.
Preparation technology the most according to claim 1, is characterized in that the filtrate described in step 3) is put refrigerator cold-storage and is: filtrate is put
0-4 DEG C of refrigerator, Cryoprecipitation 8-12h.
Preparation technology the most according to claim 1, is characterized in that the coarse crystallization proper amount of methanol water dissolution described in step 4)
For: coarse crystallization adds the methanol aqueous solution that mass fraction is 60-80%, and tepidarium is heated so that it is be in supersaturation dissolved state.
Preparation technology the most according to claim 1, is characterized in that being separated into through high performance liquid chromatography described in step 4): adopt
With C18 preparative hplc post, flowing is 30-50% methanol-water mutually, and ultraviolet detection wavelength is 218nm, and flow velocity is 200-500mL/
Min, sample size is 50-100mL/ time, repeats sample introduction, collects five lactone fractions of BB, GJ, GC, GA and GB.
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| CN102627656A (en) * | 2012-04-19 | 2012-08-08 | 曹明成 | Process for extraction and separation of ginkgolides A, B, C, J, M and bilobalide |
| CN102659808A (en) * | 2012-04-23 | 2012-09-12 | 成都百裕科技制药有限公司 | Extraction separation method of ginkgolides |
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| CN102627656A (en) * | 2012-04-19 | 2012-08-08 | 曹明成 | Process for extraction and separation of ginkgolides A, B, C, J, M and bilobalide |
| CN102659808A (en) * | 2012-04-23 | 2012-09-12 | 成都百裕科技制药有限公司 | Extraction separation method of ginkgolides |
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