CN1800188A - Method for separating and preparing triptolide diol from tripterygium wilfordii - Google Patents
Method for separating and preparing triptolide diol from tripterygium wilfordii Download PDFInfo
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- CN1800188A CN1800188A CN 200610048993 CN200610048993A CN1800188A CN 1800188 A CN1800188 A CN 1800188A CN 200610048993 CN200610048993 CN 200610048993 CN 200610048993 A CN200610048993 A CN 200610048993A CN 1800188 A CN1800188 A CN 1800188A
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- triptodiolide
- obtains
- trypterygine
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- raw material
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- 238000000034 method Methods 0.000 title claims abstract description 15
- 241000830536 Tripterygium wilfordii Species 0.000 title claims abstract description 11
- 235000015398 thunder god vine Nutrition 0.000 title claims abstract description 10
- YKUJZZHGTWVWHA-UHFFFAOYSA-N triptolide Natural products COC12CC3OC3(C(C)C)C(O)C14OC4CC5C6=C(CCC25C)C(=O)OC6 YKUJZZHGTWVWHA-UHFFFAOYSA-N 0.000 title abstract 5
- -1 triptolide diol Chemical class 0.000 title 1
- 239000002994 raw material Substances 0.000 claims abstract description 24
- 239000007787 solid Substances 0.000 claims abstract description 24
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims abstract description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 17
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims abstract description 13
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000000741 silica gel Substances 0.000 claims abstract description 12
- 229910002027 silica gel Inorganic materials 0.000 claims abstract description 12
- 238000002425 crystallisation Methods 0.000 claims abstract description 10
- 230000008025 crystallization Effects 0.000 claims abstract description 10
- 241001234523 Velamen Species 0.000 claims abstract description 8
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims abstract description 8
- 238000000605 extraction Methods 0.000 claims abstract description 8
- 239000012074 organic phase Substances 0.000 claims abstract description 3
- PUJWFVBVNFXCHZ-SQEQANQOSA-N Tripdiolide Chemical compound O=C1OCC([C@@H]2C3)=C1[C@@H](O)C[C@]2(C)[C@]12O[C@H]1[C@@H]1O[C@]1(C(C)C)[C@@H](O)[C@]21[C@H]3O1 PUJWFVBVNFXCHZ-SQEQANQOSA-N 0.000 claims description 43
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 30
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 30
- 239000000284 extract Substances 0.000 claims description 20
- 239000002904 solvent Substances 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 18
- 229960001701 chloroform Drugs 0.000 claims description 14
- 239000012043 crude product Substances 0.000 claims description 12
- 229960001866 silicon dioxide Drugs 0.000 claims description 11
- 238000001953 recrystallisation Methods 0.000 claims description 9
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 7
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 7
- 230000007935 neutral effect Effects 0.000 claims description 7
- 239000003960 organic solvent Substances 0.000 claims description 7
- 238000010828 elution Methods 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 4
- 241000545405 Tripterygium Species 0.000 claims description 4
- 238000004440 column chromatography Methods 0.000 claims description 3
- 238000000638 solvent extraction Methods 0.000 claims description 3
- 238000003912 environmental pollution Methods 0.000 claims description 2
- 239000012467 final product Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000012046 mixed solvent Substances 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 1
- 239000000126 substance Substances 0.000 abstract description 11
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 4
- DFBIRQPKNDILPW-CIVMWXNOSA-N Triptolide Chemical compound O=C1OCC([C@@H]2C3)=C1CC[C@]2(C)[C@]12O[C@H]1[C@@H]1O[C@]1(C(C)C)[C@@H](O)[C@]21[C@H]3O1 DFBIRQPKNDILPW-CIVMWXNOSA-N 0.000 abstract 4
- 239000003153 chemical reaction reagent Substances 0.000 abstract 1
- 238000002156 mixing Methods 0.000 abstract 1
- 239000012071 phase Substances 0.000 description 14
- 238000002360 preparation method Methods 0.000 description 6
- 230000006837 decompression Effects 0.000 description 5
- 238000011084 recovery Methods 0.000 description 5
- 238000003810 ethyl acetate extraction Methods 0.000 description 4
- 238000010898 silica gel chromatography Methods 0.000 description 4
- 239000003814 drug Substances 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 230000003509 anti-fertility effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 230000036039 immunity Effects 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
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- Steroid Compounds (AREA)
Abstract
The invention discloses a method for separating preparing for triptolide ethylene alcohol from Tripterygium wilfordii. It uses the Tripterygium wilfordii velamen extraction of triptolide ethylene alcohol as raw material and uses mixing reagent to eject a plurality of times to obtain the solid substance which uses organic solution to eject a plurality of times, it collects the organic phase and evaporate to dryness to obtain the solid substance, and then it coats primary silica gel column or normal alumina column and uses carrene, chloroform or dichloromethane to clean it to obtain the triptolide ethylene alcohol course product, and then it uses carreen-ether crystallization to obtain the triptolide ethylene alcohol coarse-grain, it obtains the purifying grain by re-crystallizing two times.
Description
Technical field
The present invention relates to a kind of method for preparing Triptodiolide of from trypterygine, separating.
Background technology
Trypterygine (Tripterygium Wilfordii Hook.f.) is to defend the Mao Ke tripterygium plant, and the whole world has 4 kinds, in homemade 4 kinds, 3 kinds of be used as medicine (chief editor such as Li Ruilin, research of trypterygine and clinical application, first versions, Beijing, China Science Tech Publishing House, 1989:11-12).Because trypterygine has significantly physiologically active such as anti-inflammatory, immunity, antitumor, anticancer, antifertility, be widely used in (Zhou Xue-ping et al. on the treatment of diseases such as rheumatosis, tetter, ephrosis, Journal of Traditional ChineseMedicine (Engl.), 2004,24 (2): 83-87; Hua Guo et al., World Journal ofGastroenterology (Engl.), 2003,9 (7): 1550-1553; Wang Li-Ling et al., Chinese Journal of Integrative Medicine (Engl.), 2003,9 (3): 191-194; HuYong-Xiu et al., Chinese Medical Journal (Engl.), 2003,116 (2): 284-287; Qian, Shao Zhen et al., Contraception, 1995,51 (2): 121-129).
Triptodiolide (Tipdiolide), molecular formula is C
20H
24O
7, be (Journal of the American Chemical Society, S.Morris Kupchan etal, 1972,94 (20): 7194) of a kind of diterpene-kind compound in the trypterygine.Triptodiolide (having another name called Triptodiolide) is (Zhang Chongpu etc., Acta Pharmaceutica Sinica, 1993,28 (2): 110-115 of one of main active ingredient in the trypterygine; Zhang Jianwei etc., practical andrology magazine, 1996,2 (2): 81-84; Zhang Liang etc., China Medicine University's journal, 1990,21 (4): 251-256), be the main active compound in the Chinese medicine Glucosidorum Tripterygll Totorum (Zhang Chongpu etc., Chinese Pharmaceutical Journal, 1994,29 (8): 493-495).
Existing bibliographical information separates the method that obtains Triptodiolide and is generally and adopts Radix Tripterygii Wilfordii extract through column chromatography (Lin Sui etc. repeatedly, Acta Pharmaceutica Sinica, 2005,40 (7): 632-635), process is loaded down with trivial details, length consuming time, document (Wen-Zhen Gu is also arranged, et al. International Journal ofImmunopharmacology, 1995,17 (5): 351-356) report adopts the preparation of preparation high performance liquid phase to separate Triptodiolide, is that each sample introduction operation sample is few, the cost height, also have report to adopt the multidimensional adverse current chromatogram to prepare Triptodiolide (Jun Wei et al., Journal of Liquid Chromatography ﹠amp; Related Technologies, 2005,28:1903-1911),, this method is equipped with but being not suitable for the Triptodiolide large-scale separation.The present invention adopts organic solvent commonly used that Radix Tripterygii Wilfordii extract is separated, through solvent extraction simply several times, cross a chromatography column at last, use the single organic solvent wash-out, crystallization just can obtain the Triptodiolide coarse-grain, and recrystallization can obtain pure crystalline substance twice.
Summary of the invention
The purpose of this invention is to provide a kind of method for preparing Triptodiolide of from trypterygine, separating.
It is that the tripterygium root peel extract that contains Triptodiolide is done raw material, with mixed extractant solvent for several times, the solids that obtains is dispersed in the water with organic solvent extraction for several times, collects organic phase, last silicagel column of the solids that evaporate to dryness obtains or neutral alumina post, with methylene dichloride, trichloromethane or ethylene dichloride wash-out, obtain the Triptodiolide crude product,, obtain the Triptodiolide coarse-grain with methylene dichloride-ether crystallization, recrystallization twice promptly gets pure crystalline substance
Advantage of the present invention is: trypterygine is widely distributed at southern china, therefore cheap and easy to get, simple for process, quick, begin through simple extraction for several times from raw material, cross a chromatography column for last, use the single organic solvent wash-out, crystallization just can obtain the Triptodiolide coarse-grain, and recrystallization can obtain pure crystalline substance twice.Solvent for use is substantially all recyclable, and environmental pollution is little, and the Triptodiolide cost that is obtained is lower, purity is high, is fit to industrial scale production.
Embodiment
Step of the present invention is as follows:
1) velamen of Tripterygium wilfordii is pulverized, velamen of Tripterygium wilfordii is pulverized (crossing 60 mesh sieves), with (80-95%) ethanol lixiviate of 8 times of amounts 3-5 time, each 10 hours, merge to concentrate and reclaim ethanol and obtain medicinal extract, medicinal extract with ethyl acetate or chloroform extraction for several times, extract carries out silica gel or neutral alumina column chromatography, and with methyl alcohol-chloroform (3: 97,5: 95,10: 90) gradient elution, substep is collected, concentrating under reduced pressure contains the Triptodiolide part, and evaporate to dryness gained solid is that raw material gets final product
2) raw material propyl carbinol: the solvent systems extracted several times of ethanol: water=30-35: 0.1-0.5: 30-35, thin-layer chromatography detects, and collects the following phase that contains Triptodiolide, and concentrating under reduced pressure reclaims solvent, obtains solids.
3) step 2 extracts the solids that obtains and is dispersed in usefulness ethyl acetate in the water, trichloromethane or extracted with diethyl ether several, phase in the collection, and decompression and solvent recovery obtains solids.
4) silicagel column or neutral alumina post on the solids that obtains of step 3, methylene dichloride, trichloromethane or ethylene dichloride wash-out are collected elutriant, and concentrating under reduced pressure reclaims organic solvent, obtains the Triptodiolide crude product.
5) the Triptodiolide crude product obtains the Triptodiolide coarse-grain with methylene dichloride-ether crystallization, and recrystallization twice promptly gets pure crystalline substance.
Embodiment 1:
Velamen of Tripterygium wilfordii passes through ethanol lixiviate, ethyl acetate extraction, silica gel column chromatography, and usefulness methyl alcohol-chloroform (3: 97,5: 95,10: 90) gradient elution, substep is collected, and concentrating under reduced pressure contains the Triptodiolide part, and evaporate to dryness gained solid is a raw material.Raw material propyl carbinol: ethanol: the solvent systems of water=30: 0.1: 30 (v/v) extracts.At first place separating funnel, add the 10g raw material and rocked standing demix 3 minutes by above-mentioned volume ratio preparation 0.5l solvent, isoequilibrium is after for some time, tell up and down two-phase, extract again 3 times according to above-mentioned steps behind the last phase concentrating under reduced pressure, merge concentrated mutually down solids.The solids that obtains is dispersed in the water, add the 100ml ethyl acetate, according to ethyl acetate: the ratio extraction of water=1: 1 (v/v) 2 times, phase decompression and solvent recovery in the collection, the Triptodiolide crude product that obtains cross silicagel column (crude product/silica gel=1: 30, w/w), use the methylene dichloride wash-out, methylene dichloride-ether crystallization obtains coarse-grain, and recrystallization obtains the pure crystalline substance of Triptodiolide for twice, and yield is 0.95% (in raw material).
Embodiment 2:
Velamen of Tripterygium wilfordii passes through ethanol lixiviate, ethyl acetate extraction, silica gel column chromatography, and usefulness methyl alcohol-chloroform (3: 97,5: 95,10: 90) gradient elution, substep is collected, and concentrating under reduced pressure contains the Triptodiolide part, and evaporate to dryness gained solid is a raw material.Raw material propyl carbinol: ethanol: the solvent systems of water=30: 0.2: 30 (v/v) extracts.At first place separating funnel, add the 10g raw material and rocked standing demix 3 minutes by above-mentioned volume ratio preparation 0.5l solvent, isoequilibrium is after for some time, tell up and down two-phase, extract again 3 times according to above-mentioned steps behind the last phase concentrating under reduced pressure, merge concentrated mutually down solids.The solids that obtains is dispersed in the water, add the 100ml ether, according to ether: the ratio extraction of water=1: 1 (v/v) 2 times, phase decompression and solvent recovery in the collection, the Triptodiolide crude product that obtains cross silicagel column (crude product/silica gel=1: 30, w/w), use the trichloromethane wash-out, methylene dichloride-ether crystallization obtains coarse-grain, and recrystallization obtains the pure crystalline substance of Triptodiolide for twice, and yield is 0.91% (in raw material).
Embodiment 3:
Velamen of Tripterygium wilfordii passes through ethanol lixiviate, ethyl acetate extraction, silica gel column chromatography, and usefulness methyl alcohol-chloroform (3: 97,5: 95,10: 90) gradient elution, substep is collected, and concentrating under reduced pressure contains the Triptodiolide part, and evaporate to dryness gained solid is a raw material.Raw material propyl carbinol: ethanol: the solvent systems of water=35: 0.1: 35 (v/v) extracts.At first place separating funnel, add the 10g raw material and rocked standing demix 3 minutes by above-mentioned volume ratio preparation 0.5l solvent, isoequilibrium is after for some time, tell up and down two-phase, extract again 3 times according to above-mentioned steps behind the last phase concentrating under reduced pressure, merge concentrated mutually down solids.The solids that obtains is dispersed in the water, add the 100ml ethyl acetate, according to ethyl acetate: the ratio extraction of water=1: 1 (v/v) 2 times, phase decompression and solvent recovery in the collection, the Triptodiolide crude product that obtains cross the neutral alumina post (crude product/neutral alumina=1: 30, w/w), use the ethylene dichloride wash-out, methylene dichloride-ether crystallization obtains coarse-grain, and recrystallization obtains the pure crystalline substance of Triptodiolide for twice, and yield is 0.92% (in raw material).
Embodiment 4: velamen of Tripterygium wilfordii passes through ethanol lixiviate, ethyl acetate extraction, silica gel column chromatography, and usefulness methyl alcohol-chloroform (3: 97,5: 95,10: 90) gradient elution, substep is collected, and concentrating under reduced pressure contains the Triptodiolide part, and evaporate to dryness gained solid is a raw material.Raw material propyl carbinol: ethanol: the solvent systems of water=35: 0.5: 35 (v/v) extracts.At first place separating funnel by above-mentioned volume ratio preparation 0.5l solvent,, add the 10g raw material and rocked 3 minutes, standing demix, isoequilibrium are told two-phase up and down after for some time, extract again 3 times according to above-mentioned steps behind the last phase concentrating under reduced pressure, merge concentrate mutually down solids.The solids that obtains is dispersed in the water, add the 100ml ethyl acetate, according to ethyl acetate: the ratio extraction of water=1: 1 (v/v) 2 times, phase decompression and solvent recovery in the collection, the Triptodiolide crude product that obtains cross silicagel column (crude product/silica gel=1: 30, w/w), use the methylene dichloride wash-out, methylene dichloride-ether crystallization obtains coarse-grain, and recrystallization obtains the pure crystalline substance of Triptodiolide for twice, and yield is 0.85% (in raw material).
Claims (5)
1. one kind is separated the method for preparing Triptodiolide from trypterygine; it is characterized in that: it is that the tripterygium root peel extract that contains Triptodiolide is done raw material; with mixed extractant solvent for several times; the solids that obtains is dispersed in the water with the organic solvent extraction several; collect organic phase; last silicagel column of the solids that evaporate to dryness obtains or neutral alumina post; use methylene dichloride; trichloromethane or ethylene dichloride wash-out; obtain the Triptodiolide crude product; with methylene dichloride-ether crystallization; obtain the Triptodiolide coarse-grain, recrystallization twice, it is raw materials used cheap and easy to get promptly to get pure brilliant the present invention; environmental pollution is little; simple for process; fast, the Triptodiolide cost that is obtained is lower; the purity height is fit to industrial scale production.
2. a kind of method for preparing Triptodiolide of from trypterygine, separating according to claim 1, it is characterized in that: the described extracting method that contains the tripterygium root peel extract of Triptodiolide is: velamen of Tripterygium wilfordii is pulverized (crossing 60 mesh sieves), with (80-95%) ethanol lixiviate of 8 times of amounts 3-5 time, each 10 hours, merge the concentrated ethanol that reclaims and obtain medicinal extract, medicinal extract with ethyl acetate or chloroform extraction for several times, extract carries out silica gel or neutral alumina column chromatography, with methyl alcohol-chloroform (3: 97,5: 95,10: 90) gradient elution, substep is collected, concentrating under reduced pressure contains the Triptodiolide part, and evaporate to dryness gained solid is that raw material gets final product.
3. a kind of method for preparing Triptodiolide of separating from trypterygine according to claim 1, it is characterized in that: described mixed solvent is the mixture of propyl carbinol, ethanol, water.
4. mixed solvent according to claim 3 is characterized in that: the ratio of described mixed solvent is: propyl carbinol: ethanol: water=30-35: 0.1-0.5: 30-35
5. a kind of method for preparing Triptodiolide of separating from trypterygine according to claim 1, it is characterized in that: described organic solvent is ethyl acetate, trichloromethane or ether.
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CNB2006100489935A CN100422191C (en) | 2006-01-11 | 2006-01-11 | Method for separating and preparing triptolide diol from tripterygium wilfordii |
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CNB2006100489935A CN100422191C (en) | 2006-01-11 | 2006-01-11 | Method for separating and preparing triptolide diol from tripterygium wilfordii |
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CN1800188A true CN1800188A (en) | 2006-07-12 |
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Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101088519B (en) * | 2007-07-17 | 2010-08-18 | 上海美通生物科技有限公司 | Tripterygium glycosides extract and its extraction process |
CN101481401B (en) * | 2008-04-10 | 2012-05-23 | 中国科学院上海药物研究所 | Tripterygium wilfordii diterpenoid lactone derivative, pharmaceutical composition thereof and use in genital system tumor resistance |
CN104231032A (en) * | 2013-06-13 | 2014-12-24 | 宁波工程学院 | Method for separating tripdiolide from Tripterygium Wilfordii Hook F leaves |
CN105601700A (en) * | 2016-01-07 | 2016-05-25 | 江西中医药大学 | Method for preparing tripdiolide from tripterygium wilfordii |
CN106153794A (en) * | 2015-04-10 | 2016-11-23 | 浙江海洋学院 | The method of triptolide in a kind of microwave radiation exaraction/HPLC detection tripterygium leaf |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1052861A (en) * | 1989-12-22 | 1991-07-10 | 中国医学科学院皮肤病研究所 | The preparation method of wilfordii alcoholic lactone and antifertility purposes |
-
2006
- 2006-01-11 CN CNB2006100489935A patent/CN100422191C/en not_active Expired - Fee Related
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101088519B (en) * | 2007-07-17 | 2010-08-18 | 上海美通生物科技有限公司 | Tripterygium glycosides extract and its extraction process |
CN101481401B (en) * | 2008-04-10 | 2012-05-23 | 中国科学院上海药物研究所 | Tripterygium wilfordii diterpenoid lactone derivative, pharmaceutical composition thereof and use in genital system tumor resistance |
CN104231032A (en) * | 2013-06-13 | 2014-12-24 | 宁波工程学院 | Method for separating tripdiolide from Tripterygium Wilfordii Hook F leaves |
CN106153794A (en) * | 2015-04-10 | 2016-11-23 | 浙江海洋学院 | The method of triptolide in a kind of microwave radiation exaraction/HPLC detection tripterygium leaf |
CN105601700A (en) * | 2016-01-07 | 2016-05-25 | 江西中医药大学 | Method for preparing tripdiolide from tripterygium wilfordii |
CN105601700B (en) * | 2016-01-07 | 2019-05-17 | 江西中医药大学 | The method of triptolide is prepared from tripterygium wilfordii |
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