CN101974005A - Preparation method of high-content sesquiterpenoids tripterygium alkaloid - Google Patents
Preparation method of high-content sesquiterpenoids tripterygium alkaloid Download PDFInfo
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Abstract
The invention discloses a method of separately preparing high-content sesquiterpenoids tripterygium alkaloid monomers by using semi-preparation chromatography, comprising the following steps of: with tripterygium ethyl acetate extract waste liquid subjected to the removal of triptolide and tripdiolide as a raw material, leaching by chloralkane; recrystallizing by using lower alcohol as a solvent; next, preparing the high-content sesquiterpenoids tripterygium alkaloid monomers by adopting inverse high-efficiency liquid phase semi-preparation chromatography; adopting on-line ultraviolet detection; collecting objectives; and obtaining four sesquiterpenoids tripterygium alkaloid monomers (wilfortrine, wilfordine, tripterygiumgyrine and wilforine) with content which is greater than 99.0 percent after freezing and drying. Due to the adoption of the disclosed preparation method, the separated product has the advantages of high purity, short process, low cost and easy industrialization.
Description
Technical field
The invention belongs to medical technical field, be specifically related to a kind of preparation method of high-load sesquiterpenoids trypterygine alkaloid monomer.
Background technology
Trypterygine (Tripterygium wilfordii Hook.f.) is the Celastraceae tripterygium plant, be used as medicine with root, leaf, flower and fruit,,, significant curative effect is all arranged as rheumatoid arthritis, chronic nephritis, lupus erythematosus, contact dermatitis etc. to the treatment autoimmune disorder.Put down in writing according to " middle traditional Chinese medicines are planted will ", wilforine, wilfordine and diterpenoid-lactone, galactitol all have tangible anti-tumor activity, mouse leukemia and human nasopharyngeal carcinoma all there is restraining effect, can make the blood flow increasing of arteriole diastole on every side, lower the resistance of peripheral blood flow, the obstruction of microcirculation improvement, the effect of invigorating blood circulation.Multiple abnormalism reaction there is the hormonelike anti-inflammatory action with non-bacteria inflammation.
The trypterygine complex chemical composition, pharmacological action is extensive, and important clinical application value is arranged.But, limited the popularization of clinical application because the trypterygine toxic side effect is big.Should further strengthen active ingredients of thunder god vine is efficiently extracted, is purified into to trypterygine pharmaceutical chemistry, pharmacological action and Study of Clinical Application, for the further development and use research of the quality monitoring of the trypterygine prepared slices of Chinese crude drugs and trypterygine Chinese medicinal materials lays the foundation.
The trypterygine alkaloid is one of main active ingredient of trypterygine, it is the main object that people study always, the higher relatively trypterygine alkaloid of content wherein particularly, as: wilfortrine (wilfortrine), wilfordine (wilfordine), Wilforgine 20 (wilforgine) and Wilforine (wilforine) etc.The preparation of trypterygine alkaloid monomer at present mainly adopt liquid/liquid extraction method column chromatography chromatography (Lin Sui, Li Yuanchao, Sakurai letter, Guo Shunmin, Deng Fuxiao. the research of trypterygine sesquiterpene alkaloids, Botany Gazette, 2001,43 (6): 647-649; Chen Junyuan, Xia Zhilin, Deng Fuxiao. the improvement of trypterygine alkaloid extracting technique, Chinese Journal of Pharmaceuticals, 1989,20 (11): 484-485) and high-speed countercurrent chromatography (High-speed countercurrent chromatography, HSCCC) (CN100422188C) etc., main employing trypterygine rhizome is a raw material, the trypterygine alkaloid monomer content that obtains is generally about 95% or lower, its purity is difficult to satisfy the requirement of the pharmaceutical reference substance of trypterygine alkaloid monomer, also is unfavorable for the further research of trypterygine sesquiterpenoids alkaloid pharmacology.
Summary of the invention
The objective of the invention is to deficiency, a kind of half preparative chromatography separation purification method of high-load trypterygine alkaloid monomer is provided at existing trypterygine alkaloid monomer technology of preparing.
The preparation method's of high-content sesquiterpenoids trypterygine alkaloid monomer concrete steps are as follows:
1) will remove trypterygine vinyl acetic monomer medicinal extract waste liquid behind triptolide and the Triptodiolide, easy volatile organic acid with 5~15g/L, or the easy volatile alkali regulator solution pH value of 5~20g/L is to 6-10.5, carry out recrystallization, the solvent of recrystallization is a lower alcohol, the temperature of recrystallization is 0~40 ℃, obtains the thick total alkaloids of trypterygine;
2) with the thick total alkaloids of trypterygine, after being 55: 45~99: 1 acetonitrile and water mixed solvent dissolving with volume ratio, using volume ratio is that 55: 45~99: 1 acetonitrile and water mixed solvent is moving phase, flow velocity with 0.2~2.0mL/min, in 0~40 ℃ of temperature range, on the anti-phase half preparative chromatography post of C18, realize separating of wilfortrine, wilfordine, Wilforgine 20 and Wilforine, detect by on-line ultraviolet, obtain wilfortrine, wilfordine, Wilforgine 20 and Wilforine.
Described wilfortrine, wilfordine, Wilforgine 20 and Wilforine are the sesquiterpenoids alkaloid, the alkaloidal molecular structural formula of sesquiterpenoids:
Ac=acetate,Bz=benzoyl,Fur=furanoyl。
Described C18 chromatographic column is common C18 post.Described C18 chromatographic column is preferably Hypersil C18 chromatographic column.
Described lower alcohol is methyl alcohol, ethanol or Virahol.Described lower alcohol is preferably methyl alcohol.The ratio of described acetonitrile and water is 75: 25, and described flow rate of mobile phase is 1.0mL/min, and described column temperature is 30 ℃.Described easy volatile organic acid is acetic acid, hydrochloric acid or formic acid.Described easy volatile organic acid is preferably acetic acid, and acetate concentration is 10g/L.Described easy volatile alkali is ammoniacal liquor, and the concentration of ammoniacal liquor is 10g/L.
The used raw material of the present invention is the trypterygine vinyl acetic monomer medicinal extract waste liquid that removes triptolide and Triptodiolide, and the cost of material cost is low, belongs to utilization of waste material.Used various chemical reagent is general, easily purchase.Chromatographic separation and collect and can realize automatization, easy and simple to handle, the wilfortrine of acquisition, wilfordine, Wilforgine 20 and Wilforine product content height (>99.0%) are applicable to half preparative chromatograph of various models.
The present invention is described further below in conjunction with embodiment and accompanying drawing, but be not limited to the scope of present embodiment.
Description of drawings
Fig. 1 is that trypterygine alkaloid half preparative chromatography of embodiment 1 flows out the ultraviolet color atlas; Moving phase be acetonitrile/water=(60: 40, v/v) HPLC figure; Among the figure, peak 1,2,3,4 is respectively wilfortrine, wilfordine, Wilforgine 20 and Wilforine;
Fig. 2 is that trypterygine alkaloid half preparative chromatography of embodiment 3 flows out the ultraviolet color atlas; Moving phase be acetonitrile/water=(75: 25, v/v) HPLC figure; Among the figure, peak 1,2,3,4 is respectively wilfortrine, wilfordine, Wilforgine 20 and Wilforine;
Fig. 3 (a) is the one-level mass spectrum of the trypterygine alkaloid wilfortrine under the positive ion mode of atmospheric pressure chemical ionization source (APCI) that obtains in the direct injection mode that obtained by embodiment 3;
Fig. 3 (b) is the one-level mass spectrum of the trypterygine alkaloid wilfordine under the positive ion mode of atmospheric pressure chemical ionization source (APCI) that obtains in the direct injection mode that obtained by embodiment 3;
Fig. 3 (c) is the one-level mass spectrum of the trypterygine alkaloid Wilforgine 20 under the positive ion mode of atmospheric pressure chemical ionization source (APCI) that obtains in the direct injection mode that obtained by embodiment 3;
Fig. 3 (d) is the one-level mass spectrum of the trypterygine alkaloid Wilforine under the positive ion mode of atmospheric pressure chemical ionization source (APCI) that obtains in the direct injection mode that obtained by embodiment 3.
Embodiment
Embodiment 1:
Get 5.0g oneself remove the trypterygine vinyl acetic monomer medicinal extract waste liquid of triptolide and Triptodiolide, volatilize solvent after, take by weighing 2.0g in beaker, use the 10mL chloroform extraction at every turn, repeat 3 times, the combined chloroform layer obtains chloroform medicinal extract after volatilizing; The acetic acid extraction of chloroform medicinal extract usefulness 10g/L is 3 times then, merge acetic acid extraction liquid, regulate pH to 10 with 10g/L ammoniacal liquor again, cross deionized water wash 5 times of filter cake thing, oven dry obtains thick total alkaloids, adds the dissolve with methanol of 30.0mL then, at room temperature carry out recrystallization, the raw material that obtains with recrystallization carries out chromatographic separation.
The thick total alkaloids of trypterygine that recrystallization is obtained, after being 60: 40 acetonitrile and water mixed solvent dissolving with volume ratio, using volume ratio is that 60: 40 acetonitrile and water mixture is moving phase, flow velocity with 1.0mL/min, when 30 ℃ of temperature, on the anti-phase semipreparative column of Hypersil C18, separate, adopt online ultraviolet detection, the detection wavelength is 230nm, collect the compound of each chromatographic peak correspondence respectively, get wilfortrine, wilfordine, Wilforgine 20 and 4 kinds of sesquiterpenoids trypterygines of Wilforine alkaloid after the vacuum-drying.
Embodiment 2:
Get 5.0g oneself remove the trypterygine vinyl acetic monomer medicinal extract waste liquid of triptolide and Triptodiolide, volatilize solvent after, take by weighing 2.0g in beaker, use the 10mL chloroform extraction at every turn, repeat 3 times, the combined chloroform layer obtains chloroform medicinal extract after volatilizing; The formic acid extraction of chloroform medicinal extract usefulness 10g/L is 3 times then, merge formic acid extraction liquid, regulate pH to 6 with 15g/L formic acid ammoniacal liquor again, cross deionized water wash 5 times of filter cake thing, oven dry obtains thick total alkaloids, adds the Virahol dissolving of 20.0mL then, at room temperature carry out recrystallization, the raw material that obtains with recrystallization carries out chromatographic separation.
The thick total alkaloids of trypterygine that recrystallization is obtained, after being 99: 1 acetonitrile and water mixed solvent dissolving with volume ratio, using volume ratio is that 99: 1 acetonitrile and water mixture is moving phase, flow velocity with 0.2mL/min, when 40 ℃ of temperature, on the anti-phase semipreparative column of Hypersil C18, separate, adopt online ultraviolet detection, the detection wavelength is 230nm, collect the compound of each chromatographic peak correspondence respectively, get wilfortrine, wilfordine, Wilforgine 20 and 4 kinds of sesquiterpenoids trypterygines of Wilforine alkaloid after the vacuum-drying.
Embodiment 3:
Get 10.0g oneself remove the trypterygine vinyl acetic monomer medicinal extract waste liquid of triptolide and Triptodiolide, volatilize solvent after, take by weighing 2.0g in beaker, use the 10mL chloroform extraction at every turn, repeat 3 times, the combined chloroform layer obtains chloroform medicinal extract after volatilizing; The acetic acid extraction of chloroform medicinal extract usefulness 10g/L is 3 times then, merge acetic acid extraction liquid, regulate pH to 10 with 8g/L ammoniacal liquor again, cross deionized water wash 5 times of filter cake thing, oven dry obtains thick total alkaloids, adds the dissolve with methanol of 10.0~50.0mL then, at room temperature carry out recrystallization, the raw material that obtains with recrystallization carries out chromatographic separation.
The thick total alkaloids of trypterygine that recrystallization is obtained, after being 75: 25 acetonitrile and water mixed solvent dissolving with volume ratio, using volume ratio is that 75: 25 acetonitrile and water mixture is moving phase, flow velocity with 1.0mL/min, when 25 ℃ of temperature, on the anti-phase semipreparative column of Hypersil C18, separate, adopt online ultraviolet detection, the detection wavelength is 230nm, collect the compound of each chromatographic peak correspondence respectively, get wilfortrine, wilfordine, Wilforgine 20 and 4 kinds of sesquiterpenoids trypterygines of Wilforine alkaloid after the vacuum-drying.
Embodiment 4:
Get 5.0g oneself remove the trypterygine vinyl acetic monomer medicinal extract waste liquid of triptolide and Triptodiolide, volatilize solvent after, take by weighing 2.0g in beaker, use the 10mL chloroform extraction at every turn, repeat 3 times, the combined chloroform layer obtains chloroform medicinal extract after volatilizing; The hydrochloric acid extraction of chloroform medicinal extract usefulness 10g/L is 3 times then, merge hydrochloric acid extraction liquid, regulate pH to 6 with 5g/L hydrochloric acid again, cross deionized water wash 5 times of filter cake thing, oven dry obtains thick total alkaloids, adds the dissolve with ethanol of 20.0mL then, at room temperature carry out recrystallization, the raw material that obtains with recrystallization carries out chromatographic separation.
The thick total alkaloids of trypterygine that recrystallization is obtained, after being 55: 45 acetonitrile and water mixed solvent dissolving with volume ratio, using volume ratio is that 55: 45 acetonitrile and water mixture is moving phase, flow velocity with 2.0mL/min, when 0 ℃ of temperature, on the anti-phase semipreparative column of Hypersil C18, separate, adopt online ultraviolet detection, the detection wavelength is 230nm, collect the compound of each chromatographic peak correspondence respectively, get wilfortrine, wilfordine, Wilforgine 20 and 4 kinds of sesquiterpenoids trypterygines of Wilforine alkaloid after the vacuum-drying.
Embodiment 5:
Get 10.0g oneself remove the trypterygine vinyl acetic monomer medicinal extract waste liquid of triptolide and Triptodiolide, volatilize solvent after, take by weighing 2.0g in beaker, use the 10mL chloroform extraction at every turn, repeat 3 times, the combined chloroform layer obtains chloroform medicinal extract after volatilizing; The acetic acid extraction of chloroform medicinal extract usefulness 15g/L is 3 times then, merge acetic acid extraction liquid, regulate pH to 10.5 with 12g/L ammoniacal liquor again, cross deionized water wash 5 times of filter cake thing, oven dry obtains thick total alkaloids, adds a certain amount of dissolve with methanol then, at room temperature carry out recrystallization, the raw material that obtains with recrystallization carries out chromatographic separation.
The thick total alkaloids of trypterygine that recrystallization is obtained, after being 75: 25 acetonitrile and water mixed solvent dissolving with volume ratio, using volume ratio is that 75: 25 acetonitrile and water mixture is moving phase, flow velocity with 1.0mL/min, when 30 ℃ of temperature, on the anti-phase semipreparative column of Hypersil C18, separate, adopt online ultraviolet detection, the detection wavelength is 230nm, collect the compound of each chromatographic peak correspondence respectively, get wilfortrine, wilfordine, Wilforgine 20 and 4 kinds of sesquiterpenoids trypterygines of Wilforine alkaloid after the vacuum-drying.
The foregoing description is used for the present invention that explains, rather than limits the invention, and in the protection domain of spirit of the present invention and claim, to any modification and the change that the present invention makes, all is included into protection scope of the present invention.
Embodiment 6:
Get 5.0g oneself remove the trypterygine vinyl acetic monomer medicinal extract waste liquid of triptolide and Triptodiolide, volatilize solvent after, take by weighing 2.0g in beaker, use the 10mL chloroform extraction at every turn, repeat 3 times, the combined chloroform layer obtains chloroform medicinal extract after volatilizing; The formic acid extraction of chloroform medicinal extract usefulness 10g/L is 3 times then, merge formic acid extraction liquid, regulate pH to 10 with 20g/L ammoniacal liquor again, cross deionized water wash 5 times of filter cake thing, oven dry obtains thick total alkaloids, adds the dissolve with ethanol of 20.0mL then, at room temperature carry out recrystallization, the raw material that obtains with recrystallization carries out chromatographic separation.
The thick total alkaloids of trypterygine that recrystallization is obtained, after being 55: 45 acetonitrile and water mixed solvent dissolving with volume ratio, using volume ratio is that 55: 45 acetonitrile and water mixture is moving phase, flow velocity with 0.2mL/min, when 30 ℃ of temperature, on the anti-phase semipreparative column of Hypersil C18, separate, adopt online ultraviolet detection, the detection wavelength is 230nm, collect the compound of each chromatographic peak correspondence respectively, get wilfortrine, wilfordine, Wilforgine 20 and 4 kinds of sesquiterpenoids trypterygines of Wilforine alkaloid after the vacuum-drying.
Claims (10)
1. the preparation method of a high-content sesquiterpenoids trypterygine alkaloid monomer is characterized in that concrete steps are as follows:
1) will remove trypterygine vinyl acetic monomer medicinal extract waste liquid behind triptolide and the Triptodiolide, easy volatile organic acid with 5~15g/L, or the easy volatile alkali regulator solution pH value of 5~20g/L is to 6-10.5, carry out recrystallization, the solvent of recrystallization is a lower alcohol, the temperature of recrystallization is 0~40 ℃, obtains the thick total alkaloids of trypterygine;
2) with the thick total alkaloids of trypterygine, after being 55: 45~99: 1 acetonitrile and water mixed solvent dissolving with volume ratio, using volume ratio is that 55: 45~99: 1 acetonitrile and water mixed solvent is moving phase, flow velocity with 0.2~2.0mL/min, in 0~40 ℃ of temperature range, on the anti-phase half preparative chromatography post of C18, realize separating of wilfortrine, wilfordine, Wilforgine 20 and Wilforine, detect by on-line ultraviolet, obtain wilfortrine, wilfordine, Wilforgine 20 and Wilforine.
2. the preparation method of a kind of high-content sesquiterpenoids trypterygine alkaloid monomer according to claim 1, it is characterized in that described wilfortrine, wilfordine, Wilforgine 20 and Wilforine are the sesquiterpenoids alkaloid, the alkaloidal molecular structural formula of sesquiterpenoids:
Ac=acetate,Bz=benzoyl,Fur=furanoyl。
3. the preparation method of a kind of high-content sesquiterpenoids trypterygine alkaloid monomer according to claim 1 is characterized in that described C18 chromatographic column is common C18 post.
4. the preparation method of a kind of high-content sesquiterpenoids trypterygine alkaloid monomer according to claim 3 is characterized in that described C18 chromatographic column is a Hypersil C18 chromatographic column.
5. the preparation method of a kind of high-content sesquiterpenoids trypterygine alkaloid monomer according to claim 1 is characterized in that described lower alcohol is methyl alcohol, ethanol or Virahol.
6. the preparation method of a kind of high-content sesquiterpenoids trypterygine alkaloid monomer according to claim 5 is characterized in that described lower alcohol is a methyl alcohol.
7. the preparation method of a kind of high-content sesquiterpenoids trypterygine alkaloid monomer according to claim 1, the ratio that it is characterized in that described acetonitrile and water is 75: 25, and described flow rate of mobile phase is 1.0mL/min, and described column temperature is 30 ℃.
8. the preparation method of a kind of high-content sesquiterpenoids trypterygine alkaloid monomer according to claim 1 is characterized in that described easy volatile organic acid is acetic acid, hydrochloric acid or formic acid.
9. the preparation method of a kind of high-content sesquiterpenoids trypterygine alkaloid monomer according to claim 8 is characterized in that described easy volatile organic acid is an acetic acid, and acetate concentration is 10g/L.
10. the preparation method of a kind of high-content sesquiterpenoids trypterygine alkaloid monomer according to claim 1 is characterized in that described easy volatile alkali is ammoniacal liquor, and the concentration of ammoniacal liquor is 10g/L.
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Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
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CN104817565A (en) * | 2015-03-17 | 2015-08-05 | 宁波市疾病预防控制中心 | Method for efficient extraction of tripterygium wilfordii alkaloids by ionic liquid |
CN112194619A (en) * | 2020-11-09 | 2021-01-08 | 重庆市中药研究院 | Isonicotinic acid derivative VIII with platelet aggregation resisting, anti-tumor and immunosuppressive activities and application thereof |
CN112225694A (en) * | 2020-11-06 | 2021-01-15 | 重庆市中药研究院 | Nicotinic acid derivative I with anti-inflammatory, immunosuppression and platelet aggregation resistance and application thereof |
CN112225693A (en) * | 2020-11-06 | 2021-01-15 | 重庆市中药研究院 | Nicotinic acid derivative IV with immunosuppression, platelet aggregation inhibition and blood glucose reduction activities and application thereof |
CN112250624A (en) * | 2020-11-06 | 2021-01-22 | 重庆市中药研究院 | Nicotinic acid derivative VII with anti-inflammatory, anti-platelet aggregation and immunosuppressive activities and application thereof |
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CN1911932A (en) * | 2006-08-25 | 2007-02-14 | 浙江大学 | Method for separating preparing tripterygium wilfordii monomer from tripterygium wilfordii by countercurrent flow chromatography |
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CN1911932A (en) * | 2006-08-25 | 2007-02-14 | 浙江大学 | Method for separating preparing tripterygium wilfordii monomer from tripterygium wilfordii by countercurrent flow chromatography |
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《第五届全国雷公藤学术会议论文汇编》 20080930 黄文华 等 雷公藤药材中 个生物碱成分的含量测定及其质量评价 133-138 1-10 , 2 * |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
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CN104817565A (en) * | 2015-03-17 | 2015-08-05 | 宁波市疾病预防控制中心 | Method for efficient extraction of tripterygium wilfordii alkaloids by ionic liquid |
CN112225694A (en) * | 2020-11-06 | 2021-01-15 | 重庆市中药研究院 | Nicotinic acid derivative I with anti-inflammatory, immunosuppression and platelet aggregation resistance and application thereof |
CN112225693A (en) * | 2020-11-06 | 2021-01-15 | 重庆市中药研究院 | Nicotinic acid derivative IV with immunosuppression, platelet aggregation inhibition and blood glucose reduction activities and application thereof |
CN112250624A (en) * | 2020-11-06 | 2021-01-22 | 重庆市中药研究院 | Nicotinic acid derivative VII with anti-inflammatory, anti-platelet aggregation and immunosuppressive activities and application thereof |
CN112194619A (en) * | 2020-11-09 | 2021-01-08 | 重庆市中药研究院 | Isonicotinic acid derivative VIII with platelet aggregation resisting, anti-tumor and immunosuppressive activities and application thereof |
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