CN110845451A - Method for extracting paclitaxel from taxus chinensis - Google Patents
Method for extracting paclitaxel from taxus chinensis Download PDFInfo
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- CN110845451A CN110845451A CN201911191817.0A CN201911191817A CN110845451A CN 110845451 A CN110845451 A CN 110845451A CN 201911191817 A CN201911191817 A CN 201911191817A CN 110845451 A CN110845451 A CN 110845451A
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- 229930012538 Paclitaxel Natural products 0.000 title claims abstract description 55
- 229960001592 paclitaxel Drugs 0.000 title claims abstract description 55
- 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 55
- 241001149649 Taxus wallichiana var. chinensis Species 0.000 title claims abstract description 31
- 238000000034 method Methods 0.000 title claims abstract description 25
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 57
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims abstract description 39
- 238000000605 extraction Methods 0.000 claims abstract description 17
- 239000012046 mixed solvent Substances 0.000 claims abstract description 17
- 239000000047 product Substances 0.000 claims abstract description 13
- 239000011265 semifinished product Substances 0.000 claims abstract description 12
- 238000002386 leaching Methods 0.000 claims abstract description 11
- 239000000843 powder Substances 0.000 claims abstract description 11
- 239000002994 raw material Substances 0.000 claims abstract description 9
- 238000002360 preparation method Methods 0.000 claims abstract description 7
- 238000013375 chromatographic separation Methods 0.000 claims abstract description 6
- 239000013078 crystal Substances 0.000 claims abstract description 6
- 238000001035 drying Methods 0.000 claims abstract description 6
- 238000003756 stirring Methods 0.000 claims abstract description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 238000010298 pulverizing process Methods 0.000 claims abstract description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 34
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 33
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 21
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 16
- 239000011347 resin Substances 0.000 claims description 14
- 229920005989 resin Polymers 0.000 claims description 14
- 238000004440 column chromatography Methods 0.000 claims description 13
- 239000003795 chemical substances by application Substances 0.000 claims description 11
- 238000002791 soaking Methods 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 9
- 238000001914 filtration Methods 0.000 claims description 8
- 150000007524 organic acids Chemical class 0.000 claims description 7
- 238000002156 mixing Methods 0.000 claims description 5
- 238000001291 vacuum drying Methods 0.000 claims description 5
- 239000003292 glue Substances 0.000 claims description 4
- 239000000463 material Substances 0.000 claims description 4
- 238000003828 vacuum filtration Methods 0.000 claims description 2
- 238000009776 industrial production Methods 0.000 abstract description 7
- 230000007547 defect Effects 0.000 abstract description 4
- 239000012535 impurity Substances 0.000 description 6
- 241001116500 Taxus Species 0.000 description 5
- 230000000694 effects Effects 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- DBXFAPJCZABTDR-KUEXGRMWSA-N Cephalomannine Natural products O=C(O[C@@H]1C(C)=C2[C@@H](OC(=O)C)C(=O)[C@]3(C)[C@@H](O)C[C@@H]4[C@](OC(=O)C)([C@H]3[C@H](OC(=O)c3ccccc3)[C@@](O)(C2(C)C)C1)CO4)[C@@H](O)[C@H](NC(=O)/C(=C\C)/C)c1ccccc1 DBXFAPJCZABTDR-KUEXGRMWSA-N 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- 229940123237 Taxane Drugs 0.000 description 2
- DBXFAPJCZABTDR-WBYYIXQISA-N cephalomannine Chemical compound O([C@@H]1[C@]2(O)C[C@@H](C(=C([C@@H](OC(C)=O)C(=O)[C@]3(C)[C@@H](O)C[C@H]4OC[C@]4([C@H]31)OC(C)=O)C2(C)C)C)OC(=O)[C@H](O)[C@@H](NC(=O)C(/C)=C/C)C=1C=CC=CC=1)C(=O)C1=CC=CC=C1 DBXFAPJCZABTDR-WBYYIXQISA-N 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 238000000053 physical method Methods 0.000 description 2
- 206010058467 Lung neoplasm malignant Diseases 0.000 description 1
- 206010025323 Lymphomas Diseases 0.000 description 1
- 206010033128 Ovarian cancer Diseases 0.000 description 1
- 206010061535 Ovarian neoplasm Diseases 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 229940041181 antineoplastic drug Drugs 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 201000010989 colorectal carcinoma Diseases 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 201000010536 head and neck cancer Diseases 0.000 description 1
- 208000014829 head and neck neoplasm Diseases 0.000 description 1
- 201000005202 lung cancer Diseases 0.000 description 1
- 208000020816 lung neoplasm Diseases 0.000 description 1
- 201000001441 melanoma Diseases 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method 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)
- Epoxy Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
Abstract
The invention relates to the technical field of Chinese yew processing, in particular to a method for extracting paclitaxel from Chinese yew. The extraction method comprises the following steps: A) leaching: pulverizing branches and leaves of Yunnan taxus chinensis serving as raw materials into coarse powder by a pulverizer; B) concentration: b, concentrating the combined extract in the step A in a concentration pot in vacuum to a concentration end point to obtain a concentrated extract; C) and (3) extraction: repeatedly extracting the extract with ethyl acetate to obtain extract; D) chromatographic separation: dissolving the extract with methanol, adding water with the volume of 15-20% of that of the methanol, and drying for 2-4 hours to obtain a taxol semi-finished product; E) preparation: and E, adding the taxol semi-finished product obtained in the step E into a mixed solvent, and stirring while adding until crystals appear to obtain the taxol finished product. Aiming at the defects of the prior art, the invention solves the problem of low efficiency of paclitaxel extraction in the prior art, has simple process and high product quality, and can meet the requirement of industrial production.
Description
Technical Field
The invention relates to the technical field of Chinese yew processing, in particular to a method for extracting paclitaxel from Chinese yew.
Background
Paclitaxel is a natural organic compound extracted from Taxus chinensis, and has remarkable effects in treating ovarian cancer, lung cancer, carcinoma of large intestine, melanoma, head and neck cancer, lymphoma, cerebroma, etc. The Food and Drug Administration (FDA) approved marketing as early as 1992. Taxol has been extracted from the bark of Taxus chinensis for a long time, and the bark of Taxus chinensis is a non-renewable resource, so that the raw material for obtaining taxol is very limited, and the preparation cost is high and the price is high. Moreover, the yew is a natural rare anticancer plant which is recognized in the world and is endangered to be extinct, the growth speed is slow under natural conditions, the regeneration capability is poor, and the yew plant resource can be seriously damaged only by taking the yew bark as the taxol extraction raw material. Paclitaxel, which is the most effective natural antitumor drug found at present, is usually extracted from the bark of yew, which seriously damages the plant resources of yew; the technology for extracting taxol from the branches and leaves of the taxus chinensis is partially imperfect, and has the defects of low yield, long production period and the like. In addition, the traditional process enriches the content of the components from about three percent to ten percent, at least 3 times of column chromatography is needed, and the processing cost is high.
Disclosure of Invention
Aiming at the defects of the prior art, the invention provides a method for extracting paclitaxel from taxus chinensis with reliable performance, solves the problem of low extraction efficiency of paclitaxel in the prior art, has simple process and high product quality, and can meet the requirement of industrial production.
The technical scheme of the invention is realized as follows: a method for extracting paclitaxel from taxus chinensis is characterized by comprising the following steps: the method comprises the following steps:
A) and leaching:
pulverizing branches and leaves of Yunnan taxus chinensis serving as raw materials into coarse powder by a pulverizer; adding an extracting agent into the obtained coarse powder according to the mass-volume ratio g: mL of 1: 4-7 in an extraction tank, soaking for 8-12 h at room temperature, filtering, continuously adding the extracting agent into filter residues, repeatedly soaking for 2-3 times, and combining leaching solutions;
B) and concentrating:
b, concentrating the combined extract in the step A in a concentration pot in vacuum to a concentration end point to obtain a concentrated extract;
C) and (3) extracting:
repeatedly extracting the extract with ethyl acetate, combining the extract phases, concentrating under normal pressure until no solvent exists, and then concentrating under reduced pressure under vacuum until the end point of concentration; extracting with n-hexane repeatedly, removing extract phase, concentrating under normal pressure until no n-hexane exists, and concentrating under vacuum under reduced pressure until the concentration end point to obtain extract;
D) and (3) chromatographic separation: dissolving the extract with methanol, adding water with the volume of 15-20% of that of the methanol, uniformly mixing, performing reversed-phase resin column chromatography, collecting eluate containing paclitaxel, adding the eluate into the reversed-phase resin column for column chromatography, collecting eluate containing paclitaxel, performing reduced pressure concentration and draining at 60-70 ℃, and drying at 40-50 ℃ for 2-4 hours to obtain a paclitaxel semi-finished product;
E) and (3) preparation: and E, adding the paclitaxel semi-finished product obtained in the step E into a mixed solvent, stirring while adding until crystals appear, standing at room temperature for 12-24 hours, carrying out vacuum filtration, and carrying out vacuum drying at 50-60 ℃ for 6-8 hours to obtain a paclitaxel finished product.
Preferably, the extractant in the step A is organic acid with the concentration of 0.1-0.2%, acetone solution with the concentration of 1-3% and methanol solution with the concentration of 1-2%, and the volume ratio of the extractant to the acetone solution is 1:1.5: 2.
In the step A, the branches and leaves of the Yunnan taxus chinensis are crushed into 150-200 meshes, and the crushing temperature is not more than 60 degrees.
Preferably, in the step E, the mixed solvent is n-hexane, ethyl acetate, ethanol and dichloromethane, and the volume ratio of the mixed solvent to the dichloromethane is 6:3:2: 5.
Preferably, the type of the reversed-phase resin in the step D is RPR, and the mass ratio of the materials to the glue is 1: 2-4.
The invention solves the defects in the background technology and has the following beneficial effects:
the invention solves the problem of low efficiency of paclitaxel extraction in the prior art, has simple process and high product quality, and can meet the requirement of industrial production. The selected extraction solvents are organic acid with the concentration of 0.1-0.2%, acetone solution with the concentration of 1-3% and methanol solution with the concentration of 1-2%, the dosage of the extraction solvents is small, the extraction is sufficient, the taxanes can be extracted to the maximum extent, the yield is high, the content of the extract is rapidly enriched after the extract is treated by a physical method, and the impurity removal effect is obvious; is very suitable for industrial production; the mixed solvent of the invention is n-hexane, ethyl acetate, ethanol and dichloromethane, can enrich the content of more than 20 percent by at least more than 70 percent after column chromatography is carried out for one time, remove a large amount of stubborn impurities such as cephalomannine and the like, control the impurities within 0.5 percent, effectively improve the quality of paclitaxel products, reduce the process load for subsequent processes, have short production period, save the cost and are very suitable for industrial production.
Detailed Description
Example 1
The method for extracting the taxol from the taxus chinensis comprises the following steps:
A) and leaching:
taking 300kg of Yunnan taxus chinensis branches and leaves as raw materials, and grinding the raw materials into coarse powder by a grinder; pulverizing branches and leaves of Taxus chinensis to 200 mesh at a temperature not higher than 60 deg. Adding an extracting agent into the obtained coarse powder according to the mass-volume ratio g: mL of 1:5 in an extraction tank, soaking for 10h at room temperature, filtering, continuously adding the extracting agent into filter residues, repeatedly soaking for 3 times, and combining three leaching solutions; the extractant is 0.15% organic acid, 2% acetone solution, and 1.5% methanol solution, and its volume ratio is 1:1.5: 2.
B) And concentrating:
concentrating the combined extract in the step (A) in a concentration pot under vacuum to a concentration end point to obtain a concentrated extract;
C) and (3) extracting:
repeatedly extracting the extract with ethyl acetate, combining the extract phases, concentrating under normal pressure until no solvent exists, and then concentrating under reduced pressure under vacuum until the end point of concentration; extracting with n-hexane repeatedly, removing extract phase, concentrating under normal pressure until no n-hexane exists, and concentrating under vacuum under reduced pressure until the concentration end point to obtain extract;
D) and (3) chromatographic separation: dissolving the extract with methanol, adding water with the volume being 18% of that of the methanol, uniformly mixing, performing reversed-phase resin column chromatography, collecting eluate containing paclitaxel, adding the eluate into the reversed-phase resin column for column chromatography, collecting eluate containing paclitaxel, concentrating under reduced pressure at 65 ℃, draining, and drying at 45 ℃ for 2-4 hours to obtain a paclitaxel semi-finished product; the model of the reverse phase resin is RPR, and the mass ratio of the material to the glue is 1: 2-4.
E) And (3) preparation: and (E) adding the taxol semi-finished product obtained in the step (E) into a mixed solvent, wherein the mixed solvent is n-hexane, ethyl acetate, ethanol and dichloromethane, and the volume ratio of the mixed solvent to the dichloromethane is 6:3:2: 5. Stirring while adding until crystals appear, standing at room temperature for 12-24 h, vacuum filtering, and vacuum drying at 55 deg.C for 7h to obtain paclitaxel product. Finally obtaining a taxol finished product; 99.62%, yield 82.3%.
Example 2
The method for extracting the paclitaxel from the taxus chinensis is characterized by comprising the following steps: the method comprises the following steps:
A) and leaching:
taking 500kg of Yunnan taxus chinensis branches and leaves as raw materials, and crushing the Yunnan taxus chinensis branches and leaves into coarse powder by a crusher, wherein the Yunnan taxus chinensis branches and leaves are crushed into 150 meshes, and the crushing temperature is not more than 60 degrees. Adding an extracting agent into the obtained coarse powder according to the mass-volume ratio g: mL of 1:4 in an extraction tank, soaking for 8 hours at room temperature, filtering, continuously adding the extracting agent into filter residues, repeatedly soaking for 2 times, and combining the two leaching solutions; the extractant is 0.1% organic acid, 1% acetone solution, and 1% methanol solution, and its volume ratio is 1:1.5: 2.
B) And concentrating:
concentrating the combined extract in the step (A) in a concentration pot under vacuum to a concentration end point to obtain a concentrated extract;
C) and (3) extracting:
repeatedly extracting the extract with ethyl acetate, combining the extract phases, concentrating under normal pressure until no solvent exists, and then concentrating under reduced pressure under vacuum until the end point of concentration; extracting with n-hexane repeatedly, removing extract phase, concentrating under normal pressure until no n-hexane exists, and concentrating under vacuum under reduced pressure until the concentration end point to obtain extract;
D) and (3) chromatographic separation: dissolving the extract with methanol, adding water accounting for 15% of the volume of the methanol, mixing uniformly, performing reversed-phase resin column chromatography, collecting eluate containing paclitaxel, adding the eluate into the reversed-phase resin column for column chromatography, collecting eluate containing paclitaxel, concentrating under reduced pressure at 60 ℃, draining, and drying at 40 ℃ for 2-4 hours to obtain a paclitaxel semi-finished product; the model of the reverse phase resin is RPR, and the mass ratio of the material to the glue is 1: 2-4.
E) And (3) preparation: and (E) adding the taxol semi-finished product obtained in the step (E) into a mixed solvent, wherein the mixed solvent is n-hexane, ethyl acetate, ethanol and dichloromethane, and the volume ratio of the mixed solvent to the dichloromethane is 6:3:2: 5. Stirring while adding until crystals appear, standing at room temperature for 12h, vacuum filtering, and vacuum drying at 50 deg.C for 6h to obtain taxol product. Finally obtaining a taxol finished product; 98.62% and a yield of 80.2%.
Example 3
The method for extracting the taxol from the taxus chinensis comprises the following steps:
A) and leaching:
taking 800kg of Yunnan taxus chinensis branches and leaves as raw materials, and grinding into 200-mesh coarse powder by a grinder; adding an extracting agent into the obtained coarse powder according to the mass-volume ratio g: mL of 1:7 in an extraction tank, soaking for 12h at room temperature, filtering, continuously adding the extracting agent into filter residues, repeatedly soaking for 3 times, and combining the leaching solutions; the extractant is 0.2% organic acid, 3% acetone solution, and 2% methanol solution, and its volume ratio is 1:1.5: 2.
B) And concentrating:
concentrating the combined extract in the step (A) in a concentration pot under vacuum to a concentration end point to obtain a concentrated extract;
C) and (3) extracting:
repeatedly extracting the extract with ethyl acetate, combining the extract phases, concentrating under normal pressure until no solvent exists, and then concentrating under reduced pressure under vacuum until the end point of concentration; extracting with n-hexane repeatedly, removing extract phase, concentrating under normal pressure until no n-hexane exists, and concentrating under vacuum under reduced pressure until the concentration end point to obtain extract;
D) and (3) chromatographic separation: dissolving the extract with methanol, adding water with a volume of 20% of that of the methanol, mixing, performing reversed-phase resin column chromatography, collecting eluate containing paclitaxel, adding the eluate into the reversed-phase resin column for column chromatography, collecting eluate containing paclitaxel, concentrating under reduced pressure at 70 deg.C, draining, and drying at 50 deg.C for 4 hr to obtain paclitaxel semi-finished product;
E) and (3) preparation: and (E) adding the taxol semi-finished product obtained in the step (E) into a mixed solvent, wherein the mixed solvent is n-hexane, ethyl acetate, ethanol and dichloromethane, and the volume ratio of the mixed solvent to the dichloromethane is 6:3:2: 5. Stirring while adding until crystals appear, standing at room temperature for 24h, vacuum filtering, and vacuum drying at 60 deg.C for 8h to obtain taxol product.
The selected extraction solvents are organic acid with the concentration of 0.1-0.2%, acetone solution with the concentration of 1-3% and methanol solution with the concentration of 1-2%, the dosage of the extraction solvents is small, the extraction is sufficient, the taxanes can be extracted to the maximum extent, the yield is high, the content of the extract is rapidly enriched after the extract is treated by a physical method, and the impurity removal effect is obvious; is very suitable for industrial production; the mixed solvent is n-hexane, ethyl acetate, ethanol and dichloromethane in a volume ratio of 6:3:2:5, can enrich the content of more than 20% by at least 70% after column chromatography is carried out for one time, remove a large amount of stubborn impurities such as cephalomannine and the like, control the impurities within 0.5%, effectively improve the quality of paclitaxel products, reduce the process load for subsequent processes, have short production period, save the cost and are very suitable for industrial production.
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention, and any modifications, equivalents, improvements and the like that fall within the spirit and principle of the present invention are intended to be included therein.
Claims (5)
1. A method for extracting paclitaxel from taxus chinensis is characterized by comprising the following steps: the method comprises the following steps:
A) and leaching:
pulverizing branches and leaves of Yunnan taxus chinensis serving as raw materials into coarse powder by a pulverizer; adding an extracting agent into the obtained coarse powder according to the mass-volume ratio g: mL of 1: 4-7 in an extraction tank, soaking for 8-12 h at room temperature, filtering, continuously adding the extracting agent into filter residues, repeatedly soaking for 2-3 times, and combining leaching solutions;
B) and concentrating:
b, concentrating the combined extract in the step A in a concentration pot in vacuum to a concentration end point to obtain a concentrated extract;
C) and (3) extracting:
repeatedly extracting the extract with ethyl acetate, combining the extract phases, concentrating under normal pressure until no solvent exists, and then concentrating under reduced pressure under vacuum until the end point of concentration; extracting with n-hexane repeatedly, removing extract phase, concentrating under normal pressure until no n-hexane exists, and concentrating under vacuum under reduced pressure until the concentration end point to obtain extract;
D) and (3) chromatographic separation: dissolving the extract with methanol, adding water with the volume of 15-20% of that of the methanol, uniformly mixing, performing reversed-phase resin column chromatography, collecting eluate containing paclitaxel, adding the eluate into the reversed-phase resin column for column chromatography, collecting eluate containing paclitaxel, performing reduced pressure concentration and draining at 60-70 ℃, and drying at 40-50 ℃ for 2-4 hours to obtain a paclitaxel semi-finished product;
E) and (3) preparation: and E, adding the paclitaxel semi-finished product obtained in the step E into a mixed solvent, stirring while adding until crystals appear, standing at room temperature for 12-24 hours, carrying out vacuum filtration, and carrying out vacuum drying at 50-60 ℃ for 6-8 hours to obtain a paclitaxel finished product.
2. The method for extracting paclitaxel from taxus chinensis as claimed in claim 1, wherein the extracting agent in step a is organic acid with concentration of 0.1-0.2%, acetone solution with concentration of 1-3% and methanol solution with concentration of 1-2%, and volume ratio is 1:1.5: 2.
3. The method for extracting paclitaxel from taxus chinensis as claimed in claim 1, wherein in the step A, the branches and leaves of Yunnan taxus chinensis are crushed into 150-200 meshes, and the crushing temperature is not more than 60 °.
4. The method of extracting paclitaxel from taxus chinensis according to claim 1, wherein in the step E, the mixed solvent is n-hexane, ethyl acetate, ethanol and dichloromethane, and the volume ratio is 6:3:2: 5.
5. The method for extracting paclitaxel from taxus chinensis according to claim 1, wherein the reverse phase resin type in the step D is RPR, and the mass ratio of the material to the glue is 1: 2-4.
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| CN106749113A (en) * | 2016-11-21 | 2017-05-31 | 江苏红豆杉药业有限公司 | A kind of method that utilization taxusyunnanensis waste residue prepares Japanese yew alcohol medicinal extract |
| CN108101869A (en) * | 2017-12-20 | 2018-06-01 | 上海金和生物制药有限公司 | A kind of extracting method of natural Japanese yew alcohol |
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