CN102603852A - Preparation method of tripterine - Google Patents
Preparation method of tripterine Download PDFInfo
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- CN102603852A CN102603852A CN2011100261915A CN201110026191A CN102603852A CN 102603852 A CN102603852 A CN 102603852A CN 2011100261915 A CN2011100261915 A CN 2011100261915A CN 201110026191 A CN201110026191 A CN 201110026191A CN 102603852 A CN102603852 A CN 102603852A
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- tripterine
- alcohol
- dissolving
- preparation
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- KQJSQWZMSAGSHN-JJWQIEBTSA-N celastrol Chemical compound C([C@H]1[C@]2(C)CC[C@@]34C)[C@](C)(C(O)=O)CC[C@]1(C)CC[C@]2(C)C4=CC=C1C3=CC(=O)C(O)=C1C KQJSQWZMSAGSHN-JJWQIEBTSA-N 0.000 title claims abstract description 25
- 238000002360 preparation method Methods 0.000 title claims abstract description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 45
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 22
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims abstract description 18
- 238000010992 reflux Methods 0.000 claims abstract description 17
- 238000001035 drying Methods 0.000 claims abstract description 4
- 230000008021 deposition Effects 0.000 claims description 26
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 24
- 238000002425 crystallisation Methods 0.000 claims description 12
- 230000008025 crystallization Effects 0.000 claims description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 11
- 238000009413 insulation Methods 0.000 claims description 8
- 241000545405 Tripterygium Species 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 5
- 230000007935 neutral effect Effects 0.000 claims description 5
- 238000001914 filtration Methods 0.000 abstract description 10
- 239000013078 crystal Substances 0.000 abstract description 9
- 238000000034 method Methods 0.000 abstract description 8
- 230000001988 toxicity Effects 0.000 abstract description 2
- 231100000419 toxicity Toxicity 0.000 abstract description 2
- 239000002244 precipitate Substances 0.000 abstract 7
- 229910052799 carbon Inorganic materials 0.000 abstract 2
- 239000000047 product Substances 0.000 abstract 2
- 239000003153 chemical reaction reagent Substances 0.000 abstract 1
- 239000012535 impurity Substances 0.000 abstract 1
- 238000009776 industrial production Methods 0.000 abstract 1
- 238000004064 recycling Methods 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 238000000605 extraction Methods 0.000 description 13
- 239000000243 solution Substances 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 7
- 239000007788 liquid Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 239000000284 extract Substances 0.000 description 4
- 239000012046 mixed solvent Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 230000001105 regulatory effect Effects 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 241000208365 Celastraceae Species 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 238000005303 weighing Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 240000006739 Celastrus paniculatus Species 0.000 description 2
- 235000017186 Celastrus paniculatus Nutrition 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 239000000287 crude extract Substances 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- -1 triterpene compound Chemical class 0.000 description 2
- 238000002137 ultrasound extraction Methods 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 230000005526 G1 to G0 transition Effects 0.000 description 1
- 235000000336 Solanum dulcamara Nutrition 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000017531 blood circulation Effects 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 238000001784 detoxification Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- GCFHZZWXZLABBL-UHFFFAOYSA-N ethanol;hexane Chemical compound CCO.CCCCCC GCFHZZWXZLABBL-UHFFFAOYSA-N 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000003808 methanol extraction Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000000934 spermatocidal agent Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a preparation method of tripterine, and the method comprises the following steps: crushing triperygium wilfordii roots, adding 5-7 times amount of 85-90% alcohol, refluxing for 2-3 times, and decolorizing the extracting solution by virtue of active carbon; recycling the alcohol from the destaining solution until the alcohol concentration is 55-65%, standing the destaining solution to precipitate, filtering out precipitates, dissolving the precipitates in 5-7 times amount of an alkaline alcohol solution, filtering out insolubles, adjusting the pH value of the filtered solution to 3-5, standing the solution to precipitate, filtering out precipitates, dissolving the precipitates in 3-5 times amount of the alkaline alcohol solution, filtering insolubles, adjusting the pH value of the filtered solution to 7, standing the solution to precipitate, filtering out precipitates, adding ethyl acetate into the precipitates to reflux and dissolve the precipitates, filtering the dissolvent solution, standing the filtered solution to crystallize, filtering out the crystal, adding 90-95% alcohol into the crystal, refluxing and dissolving the crystal, decolorizing the crystal alcohol solution by the active carbon, insulating and crystallizing the decolorized solution, finally drying the obtained crystal to obtain the tripterine pure product. The preparation method of the tripterine is convenient and simple, the impurity of the obtained product is high, the toxicity of used reagents is small, and the preparation method of the tripterine is suitable for industrial production.
Description
Technical field:
The invention belongs to the Natural Medicine Chemistry field, particularly relate to a kind of preparation method of Tripterine.
Background technology:
Tripterine is a triterpene compound, is celastrin again, molecular formula C
29H
38O
4, molecular weight 450.61, molecular structure:
Tripterine is red needle crystal, fusing point 185-200 ℃, is dissolved in methyl alcohol, ethanol, acetone, ETHYLE ACETATE, chloroform etc.; Be insoluble in water; Modern medicine study shows that it has very strong antioxygenation, and anticancer disease new vessel nucleus formation is arranged; The resisting rheumatoid disease effect is arranged, spermicide effect etc. is arranged.
Trypterygine is the Celastraceae plant, and root, leaf, flower and fruit are used as medicine, and have and dispel rheumatism, and be promoting blood circulation and removing obstruction in channels, swelling and pain relieving, desinsection detoxification.
Existing Tripterine preparation technology has:
The method that this patent of patent " a kind of method for preparing Tripterine " adopts is utilization chloroform ultrasonic extraction, solvent pairs eluting silica gel column chromatography and mixed solvent recrystallization etc.
Patent " a kind of preparation method of celastrin ", this patent disclosed method are to get Celastraceae plant root of Panicled Bittersweet root skin, pulverize, and add the methyl alcohol that its quality 4-5 doubly measures volume; Insert in the ultrasonic extraction device supersound extraction 1-3 time, united extraction liquid filters reclaim under reduced pressure methyl alcohol; Residue adds the alkali aqueous solution dissolving, filters, and filtrating is regulated the pH value to 3-5 with the Hydrogen chloride acid solution, leaves standstill; Filter, get filter residue, join on the alumina chromatographic column, the use volume ratio is methyl alcohol-chloroform mixed solvent wash-out of 3: 1; Collect the elutriant that 2-4 doubly measures column volume, decompression and solvent recovery also concentrates, and adding volume ratio is 1; 1 ethanol-normal hexane mixed solvent crystallization, fractional crystallization promptly gets.
Patent " a kind of method of in the Root of Oriental Bittersweet skin, extracting Tripterine ", this special disclosed method be for being solvent with rudimentary chloroparaffin, heating and refluxing extraction; The mass ratio of root skin powder and solvent 1: 3～20; Time is no less than 2 hours, obtains medicinal extract shape primary extract behind the extracting solution precipitation, in primary extract, adds 50～70% methyl alcohol or ethanolic soln then; Fully stir, leave standstill extraction, obtain thick paste shape crude extract behind the extraction liquid precipitation; Described purifying is to use the column chromatography separating purification of stationary phase as purification on normal-phase silica gel or reverse phase silica gel after crude extract uses dissolve with methanol, collects elutriant, obtains Powdered extract after the precipitation drying, uses the ethanol-water mixed solvent recrystallization at last.
Document " is used the preparation of novel vertical adverse current chromatogram and is separated the celastrin in the Stem of Oriental Bittersweet ", and the document adopts high speed adverse current chromatogram to prepare Tripterine.
As stated, mostly existing technology is to adopt column chromatography or preparation liquid phase at the preparation Tripterine, and preparation amount is less, and industrialization degree is low.
Summary of the invention:
The technical problem that present method will solve provides a kind of preparation method of Tripterine, and this method is easy to industriallization, and products obtained therefrom content is high.
In order to realize above-mentioned purpose of the present invention, the invention provides following technical scheme:
A kind of preparation method of Tripterine is characterized in that may further comprise the steps: get tripterygium root and pulverize, add 5-7 and doubly measure the 85-90% alcohol reflux 2-3 time, extracting solution adds activated carbon decolorizing; Destainer reclaims ethanol to determining alcohol 55-65%, places deposition, and throw out leaches, and doubly measures the alkaline alcohol solution dissolving with 5-7; Leach insolubles, regulate pH3-5, place deposition, leach deposition; Doubly measure the alkaline alcohol dissolving with 3-5 again, filter and regulate the neutral deposition of placing of pH, leach deposition; The ethyl acetate backflow dissolving is filtered, and places crystallization; Crystallisate leaches and adds activated carbon decolorizing with the dissolving of 90-95% alcohol reflux, destainer insulation crystallization, and crystallisate is drying to obtain the pure article of Tripterine.
Described alkaline alcohol is the ethanolic soln (containing sodium hydroxide 0.4-0.8%) of 70-85%.
The used acid of said adjusting pH is concentrated hydrochloric acid.
50-55 ℃ of described insulation Tc.
Advantage of the present invention is:
1) adopt extraction using alcohol, alcohol toxicity is little, and higher than the methanol extraction content under the equal conditions, is prone to purifying, and is lower than chloroform extraction cost;
2) adopt lower concentration alcohol deposition, can remove solvent components in the low alcohol, shortened the production cycle and reduced production cost;
3) adopting dissolving of twice alkali alcohol and insulation crystallization, is to utilize triterpene acids and alkali to combine solubleness to become big, and the character that acid adjustment is separated out is again removed low polar material;
4) whole technological operation is simple, and facility investment is less, and industrialization degree is high.
To combine embodiment to further specify the present invention below, but the scope that the present invention requires to protect is not limited to following embodiment.
Embodiment:
Embodiment 1
Tripterygium root is pulverized, and takes by weighing 1kg, adds 7 times of amount 85% alcohol reflux hour, leaches extracting solution, adds 5 times of amount 85% ethanolic soln refluxing extraction 1 hour again; United extraction liquid adds 100g pharmaceutical powder shaped activated carbon, and 80 ℃ decoloured 1 hour, the filtering gac, and destainer reclaims ethanol to determining alcohol 55%; Placed deposition 8 hours, throw out leaches, and gets throw out 32g, with 220ml70% ethanolic soln (containing sodium hydroxide 0.4%); Fully stirring and dissolving leaches insolubles, and concentrated hydrochloric acid is regulated pH3, places deposition; Leach deposition, use 100ml70% alcoholic solution (containing sodium hydroxide 0.4%) dissolving again, filter and regulate the neutral deposition of placing of pH, leach deposition; With the ethyl acetate backflow dissolving, filter, place crystallization, crystallisate leaches again with adding activated carbon decolorizing after the dissolving of 95% alcohol reflux; 55 ℃ of insulations of destainer crystallization, crystallisate leaches, dry red needle crystal Tripterine product 3.4g, the content 99.1% of getting.
Embodiment 2
Tripterygium root is pulverized, and takes by weighing 1kg, adds 7 times of amount 90% alcohol reflux hour, leaches extracting solution, adds 5 times of amount 90% ethanolic soln refluxing extraction 1 hour again; United extraction liquid adds 150g pharmaceutical powder shaped activated carbon, and 80 ℃ decoloured 1 hour, the filtering gac, and destainer reclaims ethanol to determining alcohol 65%; Placed deposition 12 hours, throw out leaches, and gets throw out 28g, with 140ml85% ethanolic soln (containing sodium hydroxide 0.8%); Fully stirring and dissolving leaches insolubles, and concentrated hydrochloric acid is regulated pH5, places deposition; Leach deposition, use 80ml85% ethanolic soln (containing sodium hydroxide 0.8%) dissolving again, filter and regulate the neutral deposition of placing of pH, leach deposition; With the ethyl acetate backflow dissolving, filter, place crystallization, crystallisate leaches again with adding activated carbon decolorizing after the dissolving of 90% alcohol reflux; 50 ℃ of insulations of destainer crystallization, crystallisate leaches, dry red needle crystal Tripterine product 3.8, the content 98.6% of getting.
Embodiment 3:
Tripterygium root is pulverized, and takes by weighing 10kg, adds 7 times of amount 85% alcohol reflux hour, leaches extracting solution, adds 5 times of amount 85% ethanolic soln refluxing extraction 1 hour again; United extraction liquid adds 1kg pharmaceutical powder shaped activated carbon, and 80 ℃ decoloured 1 hour, the filtering gac, and destainer reclaims ethanol to determining alcohol 60%; Placed deposition 10 hours, throw out leaches, and gets throw out 306g, with 1.6L85% ethanolic soln (containing sodium hydroxide 0.8%); Fully stirring and dissolving leaches insolubles, and concentrated hydrochloric acid is regulated pH3, places deposition; Leach deposition, use 1Lml85% ethanolic soln (containing sodium hydroxide 0.8%) dissolving again, filter and regulate the neutral deposition of placing of pH, leach deposition; With the ethyl acetate backflow dissolving, filter, place crystallization, crystallisate leaches again with adding activated carbon decolorizing after the dissolving of 90% alcohol reflux; 50 ℃ of insulations of destainer crystallization, crystallisate leaches, dry red needle crystal Tripterine product 35g, the content 98.8% of getting.
Claims (4)
1. the preparation method of a Tripterine is characterized in that may further comprise the steps: get tripterygium root and pulverize, add 5-7 and doubly measure the 85-90% alcohol reflux 2-3 time, extracting solution adds activated carbon decolorizing; Destainer reclaims ethanol to determining alcohol 55-65%, places deposition, and throw out leaches, and doubly measures the alkaline alcohol solution dissolving with 5-7; Leach insolubles, regulate pH3-5, place deposition, leach deposition; Doubly measure the alkaline alcohol dissolving with 3-5 again, filter and regulate the neutral deposition of placing of pH, leach deposition; The ethyl acetate backflow dissolving is filtered, and places crystallization; Crystallisate leaches and adds activated carbon decolorizing with the dissolving of 90-95% alcohol reflux, destainer insulation crystallization, and crystallisate is drying to obtain the pure article of Tripterine.
2. according to the preparation method of the said Tripterine of claim 1, it is characterized in that the described alkaline alcohol of step is the ethanolic soln (containing sodium hydroxide 0.4-0.8%) of 70-85%.
3. according to the preparation method of the said Tripterine of claim 1, it is characterized in that the used acid of step said adjusting pH is concentrated hydrochloric acid.
4. according to the preparation method of the said Tripterine of claim 1, it is characterized in that 50-55 ℃ of the described insulation Tc of step.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2011100261915A CN102603852A (en) | 2011-01-25 | 2011-01-25 | Preparation method of tripterine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2011100261915A CN102603852A (en) | 2011-01-25 | 2011-01-25 | Preparation method of tripterine |
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| Publication Number | Publication Date |
|---|---|
| CN102603852A true CN102603852A (en) | 2012-07-25 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2011100261915A Pending CN102603852A (en) | 2011-01-25 | 2011-01-25 | Preparation method of tripterine |
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| Country | Link |
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| CN (1) | CN102603852A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106243181A (en) * | 2016-07-29 | 2016-12-21 | 合肥中科玛卡生物技术有限公司 | A kind of method extracting tripterine from Fructus Momordicae charantiae |
| CN107987118A (en) * | 2018-01-17 | 2018-05-04 | 贵州民族大学 | A kind of isolation and purification method of Celastrol |
| CN112574182A (en) * | 2020-10-12 | 2021-03-30 | 江西中医药大学 | Effective part of tripterygium wilfordii macrocyclic polyamine alkaloid and preparation method thereof |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1915280A (en) * | 2006-09-06 | 2007-02-21 | 天津医科大学 | Method of supercritical CO2 for extracting terpenoid of effective component of triperygium wilfordii, and composition |
| CN1917893A (en) * | 2004-02-09 | 2007-02-21 | 美国泛华医药公司 | Methods for isolation of triptolide compounds from tripterygium wilfordii |
| CN101638425A (en) * | 2009-08-24 | 2010-02-03 | 安徽省科学技术研究院 | Method for extracting tripterine from celastrus orbiculatus root cortex |
-
2011
- 2011-01-25 CN CN2011100261915A patent/CN102603852A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1917893A (en) * | 2004-02-09 | 2007-02-21 | 美国泛华医药公司 | Methods for isolation of triptolide compounds from tripterygium wilfordii |
| CN1915280A (en) * | 2006-09-06 | 2007-02-21 | 天津医科大学 | Method of supercritical CO2 for extracting terpenoid of effective component of triperygium wilfordii, and composition |
| CN101638425A (en) * | 2009-08-24 | 2010-02-03 | 安徽省科学技术研究院 | Method for extracting tripterine from celastrus orbiculatus root cortex |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106243181A (en) * | 2016-07-29 | 2016-12-21 | 合肥中科玛卡生物技术有限公司 | A kind of method extracting tripterine from Fructus Momordicae charantiae |
| CN107987118A (en) * | 2018-01-17 | 2018-05-04 | 贵州民族大学 | A kind of isolation and purification method of Celastrol |
| CN112574182A (en) * | 2020-10-12 | 2021-03-30 | 江西中医药大学 | Effective part of tripterygium wilfordii macrocyclic polyamine alkaloid and preparation method thereof |
| CN112574182B (en) * | 2020-10-12 | 2023-08-04 | 江西中医药大学 | Tripterygium wilfordii macrocyclic polyamine alkaloid effective part and preparation method thereof |
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Application publication date: 20120725 |