CN104031008B - 一种紫杉醇粗提物的制备方法 - Google Patents
一种紫杉醇粗提物的制备方法 Download PDFInfo
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- CN104031008B CN104031008B CN201410300569.XA CN201410300569A CN104031008B CN 104031008 B CN104031008 B CN 104031008B CN 201410300569 A CN201410300569 A CN 201410300569A CN 104031008 B CN104031008 B CN 104031008B
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- taxol
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- 229930012538 Paclitaxel Natural products 0.000 title claims abstract description 50
- 229960001592 paclitaxel Drugs 0.000 title claims abstract description 50
- RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 title claims abstract description 50
- 239000000287 crude extract Substances 0.000 title claims abstract description 20
- 238000002360 preparation method Methods 0.000 title claims abstract description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 60
- 239000002904 solvent Substances 0.000 claims abstract description 25
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims abstract description 24
- 238000003756 stirring Methods 0.000 claims abstract description 21
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 17
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 claims abstract description 15
- 238000000605 extraction Methods 0.000 claims abstract description 14
- 241000196324 Embryophyta Species 0.000 claims abstract description 11
- 238000002156 mixing Methods 0.000 claims abstract description 10
- 239000000706 filtrate Substances 0.000 claims abstract description 9
- 239000002893 slag Substances 0.000 claims abstract description 9
- 238000001914 filtration Methods 0.000 claims abstract description 8
- 238000002386 leaching Methods 0.000 claims abstract description 8
- 241001149649 Taxus wallichiana var. chinensis Species 0.000 claims abstract description 7
- 244000144992 flock Species 0.000 claims abstract description 6
- 239000012535 impurity Substances 0.000 claims abstract description 6
- 238000001556 precipitation Methods 0.000 claims abstract description 6
- 238000005204 segregation Methods 0.000 claims abstract description 6
- 238000001291 vacuum drying Methods 0.000 claims abstract description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 238000001035 drying Methods 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 5
- 238000000034 method Methods 0.000 abstract description 11
- 239000012141 concentrate Substances 0.000 abstract description 4
- 239000002131 composite material Substances 0.000 abstract 1
- 230000006837 decompression Effects 0.000 abstract 1
- 239000000284 extract Substances 0.000 description 30
- 239000000243 solution Substances 0.000 description 30
- 239000012071 phase Substances 0.000 description 28
- 239000000126 substance Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 244000162450 Taxus cuspidata Species 0.000 description 3
- 235000009065 Taxus cuspidata Nutrition 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 238000000638 solvent extraction Methods 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- 238000009834 vaporization Methods 0.000 description 3
- 230000008016 vaporization Effects 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- NBEMQPLNBYYUAZ-UHFFFAOYSA-N ethyl acetate;propan-2-one Chemical compound CC(C)=O.CCOC(C)=O NBEMQPLNBYYUAZ-UHFFFAOYSA-N 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 238000003808 methanol extraction Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 208000003174 Brain Neoplasms Diseases 0.000 description 1
- 206010006187 Breast cancer Diseases 0.000 description 1
- 208000026310 Breast neoplasm Diseases 0.000 description 1
- 201000003741 Gastrointestinal carcinoma Diseases 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 description 1
- 206010025323 Lymphomas Diseases 0.000 description 1
- 102000029749 Microtubule Human genes 0.000 description 1
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- 206010028980 Neoplasm Diseases 0.000 description 1
- 206010033128 Ovarian cancer Diseases 0.000 description 1
- 206010061535 Ovarian neoplasm Diseases 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- ZCHPKWUIAASXPV-UHFFFAOYSA-N acetic acid;methanol Chemical compound OC.CC(O)=O ZCHPKWUIAASXPV-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 229930013930 alkaloid Natural products 0.000 description 1
- 150000003797 alkaloid derivatives Chemical class 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Natural products CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 1
- WBKFWQBXFREOFH-UHFFFAOYSA-N dichloromethane;ethyl acetate Chemical compound ClCCl.CCOC(C)=O WBKFWQBXFREOFH-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 201000002313 intestinal cancer Diseases 0.000 description 1
- 201000005202 lung cancer Diseases 0.000 description 1
- 208000020816 lung neoplasm Diseases 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 201000001441 melanoma Diseases 0.000 description 1
- 210000004688 microtubule Anatomy 0.000 description 1
- 230000029115 microtubule polymerization Effects 0.000 description 1
- 150000007523 nucleic acids Chemical class 0.000 description 1
- 102000039446 nucleic acids Human genes 0.000 description 1
- 108020004707 nucleic acids Proteins 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 239000000651 prodrug Substances 0.000 description 1
- 229940002612 prodrug Drugs 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 229930000044 secondary metabolite Natural products 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000000194 supercritical-fluid extraction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 238000002137 ultrasound extraction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D305/00—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms
- C07D305/14—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms condensed with carbocyclic rings or ring systems
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
Abstract
Description
D1(%) | 5 | 10 | 15 | 20 | 25 | 30 |
P1(%) | 6.85 | 6.69 | 6.57 | 6.44 | 6.22 | 5.93 |
P2(%) | 0.084 | 0.091 | 0.095 | 0.098 | 0.098 | 0.099 |
收率(%) | 84.2 | 88.6 | 91.5 | 92.4 | 89.2 | 85.9 |
Claims (6)
Priority Applications (1)
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CN201410300569.XA CN104031008B (zh) | 2014-06-30 | 2014-06-30 | 一种紫杉醇粗提物的制备方法 |
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CN201410300569.XA CN104031008B (zh) | 2014-06-30 | 2014-06-30 | 一种紫杉醇粗提物的制备方法 |
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CN104031008A CN104031008A (zh) | 2014-09-10 |
CN104031008B true CN104031008B (zh) | 2015-12-09 |
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Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
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CN106176835A (zh) * | 2016-07-12 | 2016-12-07 | 江西省科学院应用化学研究所 | 一种用于同步提取红豆杉黄酮和多糖的萃取液及其方法 |
CN110845449A (zh) * | 2019-10-12 | 2020-02-28 | 普洱大华林业科技有限公司 | 一种红豆杉提取紫杉醇的方法 |
Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5475120A (en) * | 1990-11-02 | 1995-12-12 | University Of Florida | Method for the isolation and purification of taxol and its natural analogues |
CN1687044A (zh) * | 2005-04-05 | 2005-10-26 | 杨雪峰 | 一种紫杉醇纯品的生产方法 |
CN1774431A (zh) * | 2003-02-27 | 2006-05-17 | 沙彻姆制药国际公司 | 从天然原料分离和提纯紫杉醇的改进方法 |
CN102408318A (zh) * | 2011-12-07 | 2012-04-11 | 福建紫杉园生物有限公司 | 一种提取并纯化红杉醇的方法 |
CN103145653A (zh) * | 2013-04-12 | 2013-06-12 | 江苏斯威森生物医药工程研究中心有限公司 | 一种10-去乙酰基巴卡亭ⅲ的高效提取纯化工艺 |
CN103172598A (zh) * | 2013-03-26 | 2013-06-26 | 四川祥光农业科技开发有限公司 | 从红豆杉枝叶中提取紫杉醇的方法 |
CN103193735A (zh) * | 2013-03-26 | 2013-07-10 | 安徽和华生物医药科技有限公司 | 红豆杉紫杉醇活性提取物的提取方法 |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH06157329A (ja) * | 1992-11-19 | 1994-06-03 | Mitsui Toatsu Chem Inc | タキソール類含有レジンの効率的な抽出方法 |
KR0150337B1 (en) * | 1995-04-29 | 1998-10-15 | Samyang Zenex Co Ltd | A method for isolating taxol from taxus genus plant by chromatography |
-
2014
- 2014-06-30 CN CN201410300569.XA patent/CN104031008B/zh active Active
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5475120A (en) * | 1990-11-02 | 1995-12-12 | University Of Florida | Method for the isolation and purification of taxol and its natural analogues |
CN1774431A (zh) * | 2003-02-27 | 2006-05-17 | 沙彻姆制药国际公司 | 从天然原料分离和提纯紫杉醇的改进方法 |
CN1687044A (zh) * | 2005-04-05 | 2005-10-26 | 杨雪峰 | 一种紫杉醇纯品的生产方法 |
CN102408318A (zh) * | 2011-12-07 | 2012-04-11 | 福建紫杉园生物有限公司 | 一种提取并纯化红杉醇的方法 |
CN103172598A (zh) * | 2013-03-26 | 2013-06-26 | 四川祥光农业科技开发有限公司 | 从红豆杉枝叶中提取紫杉醇的方法 |
CN103193735A (zh) * | 2013-03-26 | 2013-07-10 | 安徽和华生物医药科技有限公司 | 红豆杉紫杉醇活性提取物的提取方法 |
CN103145653A (zh) * | 2013-04-12 | 2013-06-12 | 江苏斯威森生物医药工程研究中心有限公司 | 一种10-去乙酰基巴卡亭ⅲ的高效提取纯化工艺 |
Non-Patent Citations (6)
Title |
---|
曼地亚红豆杉枝条中紫杉醇的超声提取研究;满瑞林 等;《化学研究与应用》;20081215;第20卷(第12期);第1637-1640页,1.2.3 实验步骤 * |
紫杉醇分离提取工艺的探讨;贾祥臣 等;《化学世界》;20071101;第125-129页 * |
紫杉醇初分离工艺中的除杂方法比较;吴倩 等;《天然产物研究与开发》;20050630;第17卷(第3期);第320-324页,摘要,1.2.6 酸碱液沉淀法除杂 * |
紫杉醇提取纯化技术研究进展;赵广河 等;《食品与发酵工业》;20080530;第34卷(第5期);第138-142页 * |
紫杉醇的提取与纯化技术;韩金玉 等;《中草药》;20001025;第31卷(第10期);第789-792页,1 溶剂萃取法 * |
红豆杉中提取紫杉醇研究进展;彭天浩 等;《农产品加工(学刊)》;20130630(第6期);第57-62页 * |
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Publication number | Publication date |
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CN104031008A (zh) | 2014-09-10 |
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Effective date of registration: 20180910 Address after: 250000 3, building 302, ten road 9777, Lixia District, Ji'nan, Shandong. Patentee after: Shandong Meihua Environmental Technology Co., Ltd. Address before: 250014 room 402, West unit 14, Lin Jing villa, 3366 east road ten, Lixia District, Ji'nan, Shandong. Patentee before: Niu Zhaoying |
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Effective date of registration: 20200116 Address after: 250001 No.7 scientific research building 310, No.554, Zhengfeng Road, high tech Zone, Jinan City, Shandong Province Patentee after: Shandong Yingxiu Environmental Technology Co., Ltd Address before: 250000 3, building 302, ten road 9777, Lixia District, Ji'nan, Shandong. Patentee before: Shandong Meihua Environmental Technology Co., Ltd. |