CN105273037B - The method of separation and Extraction triptolide from tripterygium wilfordii plant - Google Patents
The method of separation and Extraction triptolide from tripterygium wilfordii plant Download PDFInfo
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Abstract
The invention belongs to Natural Medicine Chemistry, a kind of method of separation and Extraction triptolide in being related to plant from tripterygium wilfordii.Methods described comprises the following steps：1. extraction and alkali process；2. remove low pole material；With 3. column chromatographies.The method of the present invention has the following advantages that：Before column chromatography, the extraction feed liquid to tripterygium wilfordii plant carries out alkali process, some impurity components is entered water layer, alkyl chloride hydrocarbon layers impurity component is reduced, in follow-up column chromatography procedure, simplifies operation, and elution speed is fast, not viscous；Extraction times are reduced, and solvent load is greatly decreased, so that operating environment improves, and it is cost-effective；The high performance preparative liquid chromatography method that high cost need not be carried out is purified；The extraction efficiency of triptolide is high, and recovery rate can reach 0.0062wt%, and purity is up to 99.9%；Due to being the routine operation of chemical field in this method, it is easy to large-scale production.
Description
Technical field
The invention belongs to Natural Medicine Chemistry, the side of separation and Extraction triptolide in being related to a kind of plant from tripterygium wilfordii
Method.
Background technology
Tripterygium wilfordii be it is a kind of be with Chinese characteristics, the clinically higher Chinese medicine of applicating frequency, it is to difficulties such as autoimmunity diseases
The property controlled disease has preferable curative effect, has the irreplaceable effect of other similar medicines, therefore be up-and-coming medicinal raw material.
Tripterygium wilfordii complex chemical composition, pharmacological action extensively, has important clinical value, still, be applied at present
Clinical various Tripterygium Preparations are substantially the crude extract of tripterygium wilfordii, even if many glucoside pieces are nor pure active component, therefore are caused
Clinical application curative effect is slow, consumption is big, toxic side effect is big.According to the pharmacology after a large amount of activity test results of study and structure of modification
It is demonstrated experimentally that clinical various Tripterygium Preparations should develop in small and small toxicity the direction of pure, dosage towards raw material, therefore to thunder
The separation of public rattan medicinal active ingredient, extraction, prepare with scale are particularly important.
Triptolide (also known as triptolide) is one of principle active component of tripterygium wilfordii plant, triptolide
Chemical constitution be diterpenoid-lactone class formation, its structural formula is as follows：
At present from tripterygium wilfordii plant separation and Extraction triptolide pass through frequently with method be by tripterygium root, stem or leaf
Chromatography is carried out with solvent extraction, then by extract, then is crystallized.
The extracting method of triptolide is optimized Shen Qiulin etc., and it uses methanol to soak Common Threewingnut Root
Carry, then carry out ultrasonically treated and filtering, extracted after filtrate concentration with chloroform, chloroform extract is concentrated under reduced pressure into paste, then
Neutral alumina column chromatography is carried out to the paste, eluent is methanol:Ethyl acetate:Ether=1:2:1 (volume ratio) (Shen Qiu
Woods etc., triptolide modifiedly extracted method [J], University Of Agriculture and Forestry In Fujian's journal (natural science edition), 2012,41 (4)：488-
492).The advantage of this method is, with ultrasonically treated after alcohol extracting, effectively increases the recovery rate of triptolide.But, the party
Method is disadvantageous in that, by methanol extraction, chloroform extraction before column chromatography, the step of not going the removal of impurity before extraction,
The paste that chloroform extract is obtained is dense black, complicated component, and viscosity is big, dissolves highly difficult, even more viscous during column chromatography, post scanning frequency
Degree is very slow, is unfavorable for amplification production.Once reported for work and handle this condensed cream, the 8th~10 with diameter 30cm, column length 1.8m silicagel columns
Talent receives purpose thing.
Chinese patent application CN101367862A discloses one kind quickly and massively separating high purity tripterygium wilfordii from tripterygium wilfordii
The method of A prime, this method include alcoholic solvent heating extraction, petroleum ether extraction, chloroform or dichloromethane extraction, column chromatography,
Efficiently prepare liquid phase separation and crystallization.Wherein, petroleum ether extraction can remove impurity, such chloroform or dichloromethane extraction concentration
After obtained thick yellow precipitate rather than black paste, so as to reduce the burden of column chromatography.But, in the method, root
According to embodiment, petroleum ether extraction, dichloromethane is extracted, and each 3 times or 5 times, extraction times are more, and solvent load is big；In chromatogram
In column chromatography, using gradient eluent, operate not easy；In addition, in purge process, high performance preparative liquid chromatography has been used,
Cost is very high.
Because content of the triptolide in tripterygium wilfordii plant is very low, have been reported that, from velamen of Tripterygium wilfordii, radical center and full root
The extracted amount of middle triptolide is respectively 0.001wt%, 0.0004wt% and 0.0018wt%.Therefore, how effectively from
The research of separation and Extraction triptolide, i.e. Optimized Extraction Process, simplify procedures in tripterygium wilfordii plant, reduce solvent and use
Amount, reduces extraction cost, has very important significance.
The content of the invention
In view of drawbacks described above present in prior art, it is an object of the invention to provide a kind of technique is simple, high income,
Product purity is high, environment-friendly and is suitable for the side of separation and Extraction triptolide from tripterygium wilfordii plant of large-scale production
Method.
According to the present invention, the method for separation and Extraction triptolide from tripterygium wilfordii plant that the present invention is provided includes as follows
Step：
1. extraction and alkali process
Soak extraction is carried out with the mixed liquor of alcohol and water to tripterygium root, stem and/or the net medicine materical crude slice of leaf, leaching liquor is obtained；It is right
The leaching liquor, which is concentrated under reduced pressure, boils off alcohol, obtains concentrate；The chloralkane of 1~5 times of volume of concentrate is added into the concentrate
Solvent, then adds alkali, stratification after uniform mixing, obtains water layer and alkyl chloride hydrocarbon layers；
2. remove low pole material
The alkyl chloride hydrocarbon layers liquid pressure-reducing that above-mentioned steps 1 are obtained is concentrated into dope, should using non-polar solven dissolution
Methanol, methanol and water mixed liquid or acetone, the dissolution fluid concentration of gained are added in low pole material in dope, not molten thing
To dry, solid dried object is obtained；
3. column chromatography
The solid dried object obtained to above-mentioned steps 2 carries out silica gel column chromatography, isolated triptolide crystal.
The method of separation and Extraction triptolide from tripterygium wilfordii plant to the present invention is described in more detail below.
In step 1 extraction and alkali process：
The net medicine materical crude slice of tripterygium root, stem and/or leaf used, usual root, stem using 1~2mm × 10~30mm (diameter ×
It is long) bulk, leaf is the blade after clean dry, and the net medicine materical crude slice moisture requirement of the tripterygium root, stem, leaf<15wt%.
The mixed liquor of the alcohol and water is preferably the mixed liquor of first alcohol and water or second alcohol and water, and more preferably ethanol and
The mixed liquor of water；In the mixed liquor of alcohol and water, alcohol and water by volume 1~9：1 mixing, more preferably alcohol and water by volume 8：
1 mixing；
Soak extraction is carried out with the mixed liquor of alcohol and water to tripterygium root, stem and/or the net medicine materical crude slice of leaf, solid-liquid ratio is the drink
The weight ratio of the mixed liquor of piece and alcohol and water, generally 1：2~8；In soak extraction, boiled in the mixed liquor of normal temperature to alcohol and water
Immersion is extracted for 2~12 hours at temperature in point temperature range, preferably heats soak extraction, and most preferably micro-boiling soak extraction；
As needed, soak extraction can be repeated 1~3 time；
The chlorinated paraffin solvent is dichloroethanes, dichloromethane or chloroform, and preferably dichloroethanes or trichlorine
Methane；
The alkali can be sodium hydroxide or potassium hydroxide, and the alkali can be added in the form of solid or its aqueous solution,
And added preferably in the form of 0.2N~40N sodium hydroxides or potassium hydroxide aqueous solution, stratification after uniform mixing is resulting
The volume ratios of water layer and alkyl chloride hydrocarbon layers be 0.8~1.2：1, while the concentration of alkali is 0.08N~1.2N in water layer, and preferably
For 0.1N~0.8N, most preferably 0.2N~0.6N；
It can further include in step 1 extraction and alkali process and use water layer the chlorinated paraffin solvent
It is stripped, and the chlorinated paraffin solvent extract is incorporated in alkyl chloride hydrocarbon layers.
Part triptolide exists in derivative tripchlorolide form in tripterygium wilfordii, and this derivative can be with
Converted under appropriate environment：
Be not difficult to find out, handled with alkali from transforming relationship above, some impurity are transferred to water layer, and triptolide not by
Influence, and under alkaline environment, triptolide is changed into branch with what tripchlorolide form was present.It can be seen that,
This transforming relationship is the process rationality of the invention and property has given to prove in theory in high yield.
, can be more specifically by following operation in the step 2 removes low pole material：
The alkyl chloride hydrocarbon layers liquid pressure-reducing that above-mentioned steps 1 are obtained is concentrated into dope, adds silica gel and stirs, then
It is dried under reduced pressure, obtains powdered crude product；With the low pole material in the non-polar solven dissolution powdered crude product, in not molten thing plus
Enter methanol, methanol and water mixed liquid or acetone, the dissolution fluid of gained is concentrated to dryness, and obtains solid dried object；
The silica gel added into dope is generally 100~200 mesh, and the weight ratio of silica gel and dope is 0.5~2：
1, and preferably 1：1.
The non-polar solven is n-hexane or hexamethylene, and powdered crude product can be rushed repeatedly with n-hexane or hexamethylene
It is washed till n-hexane or hexamethylene eluate color is very light almost colourless；And add methanol, methanol in backward not molten thing and mixed with water
Liquid or acetone, are preferably added to acetone, and the addition of the solvent can be per g powdered 3~20ml of crude product, preferably 5~12ml.
In step 3 column chromatography：
The silicagel column uses 200~300 mesh silica gel, and uses wet method dress post；
Cyclohexane-ethyl acetate mixed liquor is used to be eluted for mobile phase, and preferred volume ratio is 1.5~1：1 ring
Hexane-ethylacetate mixed liquor, more preferably volume ratio 1：1 cyclohexane-ethyl acetate mixed liquor；In column chromatography procedure, adopt
Tracked with TLC, Kedd reagent colour developments, collect and merge the reception liquid with single triptolide spot, be concentrated under reduced pressure into small
Volume, is placed in refrigerator cold-storage, makes precipitation crystal；Crystal after precipitation uses acetone recrystallization again, and filtering is dried under reduced pressure, obtains nothing
Color needle-like triptolide crystal.
Compared with prior art, in the plant of the invention from tripterygium wilfordii separation and Extraction triptolide method have it is as follows
Advantage：(1) before column chromatography, alkali process is carried out to the extraction feed liquid of tripterygium wilfordii plant, make some impurity component structures by
Destruction, switchs to water-soluble and enters water layer, so that alkyl chloride hydrocarbon layers impurity component is reduced, do not have after being concentrated under reduced pressure from oil-soluble
There is black paste, in follow-up column chromatography procedure, simplify operation, elution speed is fast, not viscous, and is washed without gradient
It is de-；(2) extraction times are reduced, and solvent load is greatly decreased, so that operating environment improves, and it is cost-effective；(3) it is high without carrying out
The high performance preparative liquid chromatography method of cost is purified；(4) extraction efficiency of triptolide is high, and recovery rate can reach
0.0062wt%, and purity is up to 99.9%；(5) due to be in this method chemical field routine operation, be easy to big rule
Mould is produced.
Brief description of the drawings
Fig. 1 and Fig. 2 are respectively triptolide1H-NMR and13C-NMR spectrograms.
Embodiment
Hereafter, come that the present invention is described further in conjunction with specific embodiments, embodiments below is only used for illustrating
The bright present invention, and the scope of the present invention is not limited to this.
The content of triptolide is detected in embodiment below using high performance liquid chromatography (HPLC), chromatographic condition is such as
Under：
Chromatographic column：Chemcosorb5ODS-H, 25cm length × 4.6mm I.D., 5 μm of granularities
Column temperature：25℃
Mobile phase：(25:12:63) acetonitrile：Methanol：6mM sodium phosphates (pH3.2)
Flow velocity：1.0mL/min
Sample size：10μL
Detection wavelength：220nm
Embodiment 1
The separation and Extraction triptolide from tripterygium wilfordii plant as follows：
1. extraction and alkali process
The 1000g tripterygium wilfordiis branch net medicine materical crude slice of stem is weighed, 6 times, 5 times and 5 of charged material weight are pressed to the net medicine materical crude slice of tripterygium wilfordii branch stem
Times 80% ethanol-water mixture (v/v) micro-boiling extract three times, extract 3 respectively, 2,2 hours；Merge the leach cooking liquid after filtering,
It is concentrated under reduced pressure and boils off ethanol, obtains 1200ml concentrate；It is sufficiently stirred for 1500ml dichloroethanes and the concentrate, then
500~600ml 0.35N sodium hydrate aqueous solutions are added, are sufficiently stirred for；Then, stirring is stopped, stratification obtains dense black
Water layer and the bright dichloroethanes layer of yellow, the water layer is stripped with 800ml dichloroethanes again, by dichloroethanes extract with
Above-mentioned dichloroethanes is laminated simultaneously；
2. remove low pole material
Above-mentioned steps 1 are merged into obtained dichloroethanes liquid and are concentrated under reduced pressure into dope, the mesh silica gel of 15g100~200 is added
Stir, then flat beach is dried under reduced pressure in stainless steel disc in the drying box less than 60 DEG C, obtain the light yellow yellow that arrives
Powdered crude product 25g, uses HPLC to detect triptolide content for 0.27wt%；
The light yellow powdered crude products to yellow of 25g obtained above are poured into 250ml beakers or is filled in and can pressurize
Glass column in, soaked with 100ml hexamethylenes, filtering drains, be repeated 3 times to extraction hexamethylene liquid color very it is light almost without
Color；Then, the filter residue drained is transferred in beaker, pours into 200ml acetone, stir, acetone solution is extracted in filtering out, by this
Acetone solution is concentrated under reduced pressure into dry, obtains the cotton-shaped dried objects of about 6g, uses HPLC to detect triptolide content for 1.15wt%；
3. column chromatography
3 × 110cm glass column is filled with 200~300 mesh silica gel 260g, silica gel is infiltrated with mobile phase and fills post, it is above-mentioned
The cotton-shaped dried objects of 6g that step 2 is obtained loading after a small amount of flowing phased soln, mobile phase is volume ratio 1：1 hexamethylene-acetic acid
Ethyl ester mixed liquor, is then eluted with the mobile phase, is tracked using TLC, and Kedd reagent colour developments are collected and merged with single
Reception liquid (the R of triptolide spotf=about 0.6), small size is concentrated under reduced pressure into, refrigerator cold-storage is placed in, makes precipitation crystal；Analysis
Crystal after going out uses acetone recrystallization again, and filtering is dried under reduced pressure, obtains colourless needles triptolide crystal 62mg, uses
HPLC detects purity 99.5%.
Triptolide is confirmed as through nuclear magnetic resonance spectroscopy,1H-NMR and13C-NMR spectrograms are referring to Fig. 1 and Fig. 2.
Embodiment 2
The separation and Extraction triptolide from tripterygium wilfordii plant as follows：
1. extraction and alkali process
400kg tripterygium wilfordii ramose root core medicine materical crude slice is weighed, to the tripterygium wilfordii ramose root core medicine materical crude slice 2000L, 1600L and 1600L
80% ethanol-water mixture (v/v) micro-boiling is extracted three times, extract 3 respectively, 2,2 hours；Merge the leach cooking liquid after filtering, decompression
Concentration boils off ethanol, obtains about 480L concentrate；It is sufficiently stirred for 480L dichloroethanes and the concentrate, stands 2 hours,
40L 20wt% sodium hydrate aqueous solutions are then added, 10min is sufficiently stirred for；Then, stirring is stopped, standing overnight makes layering,
Obtain dense black water layer and the bright dichloroethanes layer of yellow；
2. remove low pole material
The dichloroethanes liquid that above-mentioned steps 1 are obtained is concentrated under reduced pressure into dope, adds the mesh silica gel stirring of 3kg100~200
Uniformly, then flat beach in stainless steel disc, is dried under reduced pressure in the drying box less than 60 DEG C, obtains the light yellow powder to yellow
Shape crude product 5.65kg；
The light yellow powdered crude product 400g to yellow obtained above is poured into large beaker or is filled in what can be pressurizeed
In glass column, soaked with 1500ml hexamethylenes, filtering drains, the hexamethylene liquid color being repeated 3 times to extraction is very light almost colourless
(hexamethylene can be reclaimed, and be reused)；Then, the filter residue drained is transferred in beaker, pours into 3000ml acetone, fully stir
Mix uniform, acetone solution is extracted in filtering out, the acetone solution is concentrated under reduced pressure into dry, obtain the cotton-shaped dried objects of about 72g；
3. column chromatography
12 × 110cm glass column, volume ratio 1 are filled with 200~300 mesh silica gel 4000g：1 cyclohexane-ethyl acetate
Mixed liquor mobile phase wet method is filled, the cotton-shaped dried objects of the 72g that above-mentioned steps 2 are obtained loading after a small amount of flowing phased soln, so
Eluted, tracked using TLC with the mobile phase afterwards, Kedd reagent colour developments are collected and merged with single triptolide spot
Reception liquid (the R of pointf=about 0.6), small size is concentrated under reduced pressure into, refrigerator cold-storage is placed in, makes precipitation crystal；Crystal after precipitation is again
With acetone recrystallization, filtering is dried under reduced pressure, obtains colourless needles triptolide crystal 920mg, and purity is detected using HPLC
99.9%.
Claims (8)
1. the method for separation and Extraction triptolide, comprises the following steps in a kind of plant from tripterygium wilfordii：
1. extraction and alkali process
Soak extraction is carried out with the mixed liquor of alcohol and water to tripterygium root, stem and/or the net medicine materical crude slice of leaf, leaching liquor is obtained；To the leaching
Extract, which is concentrated under reduced pressure, boils off alcohol, obtains concentrate；The chlorinated paraffin solvent of 1~5 times of volume of concentrate is added into the concentrate,
Alkali is then added, stratification after uniform mixing obtains water layer and alkyl chloride hydrocarbon layers；
2. remove low pole material
The alkyl chloride hydrocarbon layers liquid pressure-reducing that above-mentioned steps 1 are obtained is concentrated into dope, adds silica gel and stirs, then depressurizes
Dry, obtain powdered crude product；With the low pole material in the non-polar solven dissolution powdered crude product, first is added in not molten thing
Alcohol, methanol and water mixed liquid or acetone, the dissolution fluid of gained are concentrated to dryness, and obtain solid dried object；
3. column chromatography
The solid dried object progress silica gel column chromatography that above-mentioned steps 2 are obtained, isolated triptolide crystal,
Wherein, in step 1 extraction and alkali process, the alkali is added in the form of solid or its aqueous solution, uniformly
Stratification after mixing, resulting water layer and the volume ratio of alkyl chloride hydrocarbon layers are 0.8~1.2：1, at the same in water layer alkali it is dense
Spend for 0.08N~1.2N；
In step 2 removes low pole material, the silica gel added into dope is the weight of 100~200 mesh, silica gel and dope
The ratio between amount is 0.5~2：1；The non-polar solven is n-hexane or hexamethylene, with n-hexane or hexamethylene to powdered crude product
Rinse very light almost colourless to n-hexane or hexamethylene eluate color repeatedly；And added in backward not molten thing methanol, methanol with
Water mixed liquid or acetone, the addition of the solvent is per the powdered 3~20ml of crude product of g.
2. according to the method described in claim 1, it is characterized in that, in step 1 extraction and alkali process, used
Tripterygium root, stem use the bulk of 1~2mm diameter × 10~30mm length, and leaf is the blade after clean dry, and the tripterygium wilfordii
The net medicine materical crude slice moisture requirement ＜ 15wt% of root, stem, leaf；
The mixed liquor of the alcohol and water is the mixed liquor of first alcohol and water or second alcohol and water；
The weight ratio of the mixed liquor of the medicine materical crude slice and alcohol and water is 1：2~8；
Soak 2~12 hours and extract at temperature in the mixed liquor boiling point temperature range of normal temperature to alcohol and water.
3. method according to claim 2, it is characterized in that, in step 1 extraction and alkali process, the alcohol and
The mixed liquor of water is the mixed liquor of second alcohol and water, in the mixed liquor of alcohol and water, alcohol and water by volume 1~9：1 mixing；
The extraction uses micro-boiling soak extraction, and repeats soak extraction 1~3 time.
4. method according to claim 3, it is characterized in that, in step 1 extraction and alkali process, in alcohol and water
Mixed liquor in, alcohol and water by volume 8：1 mixing.
5. method according to any one of claim 1 to 4, it is characterized in that, in step 1 extraction and alkali process
In, the chlorinated paraffin solvent is dichloroethanes, dichloromethane or chloroform；The alkali is sodium hydroxide or potassium hydroxide.
6. method according to claim 5, it is characterized in that, in step 1 extraction and alkali process, the chloro
Alkane solvent is dichloroethanes or chloroform；The concentration of alkali is 0.1N~0.8N in water layer.
7. method according to claim 6, it is characterized in that, in step 1 extraction and alkali process, it can also enter
One step includes being stripped water layer with the chlorinated paraffin solvent, and the chlorinated paraffin solvent extract is incorporated into alkyl chloride
In hydrocarbon layers.
8. according to the method described in claim 1, it is characterized in that, in step 3 column chromatography, the silicagel column uses 200
~300 mesh silica gel, and use wet method dress post；
Volume ratio is used for 1.5~1：1 cyclohexane-ethyl acetate mixed liquor is that mobile phase is eluted；In column chromatography procedure
In, tracked using TLC, Kedd reagent colour developments, collect and merge the reception liquid with single triptolide spot, be concentrated under reduced pressure
To small size, refrigerator cold-storage is placed in, makes precipitation crystal；Crystal after precipitation uses acetone recrystallization again, and filtering is dried under reduced pressure, obtained
To colourless needles triptolide crystal.
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