CN101020671A - Process of separating and purifying taxol efficiently - Google Patents
Process of separating and purifying taxol efficiently Download PDFInfo
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- CN101020671A CN101020671A CN 200610047378 CN200610047378A CN101020671A CN 101020671 A CN101020671 A CN 101020671A CN 200610047378 CN200610047378 CN 200610047378 CN 200610047378 A CN200610047378 A CN 200610047378A CN 101020671 A CN101020671 A CN 101020671A
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Abstract
The present invention relates to process of separating and purifying taxol efficiently, and has the features of simple technological process and high product yield. The process includes an extracting procedure, a degumming procedure and a separating and purifying procedure. The degumming procedure adopts high pressure silica gel column chromatography; and the separating and purifying procedure adopts crystallization in an acetone-petroleum ether system to separate the extracted matter into taxol, cephalotmannine and 7-epitaxol. The present invention can obtain taxol of content not lower than 99.5 %, cephalotmannine of content 0.15 %, and 7-epitaxol of content 0.10 %.
Description
Technical field
The present invention relates to technical field of pharmaceuticals, exactly is a kind of novel method of separating and purifying taxol efficiently.Particularly provide tripping silica gel column chromatography column chromatography to remove colloid, utilized acetone-sherwood oil system crystallization taxane compounds to be separated into the method for taxol, Cephalomannine, 7-Epitaxol 3 parts.
Background technology:
Taxol becomes the focus of attracting attention in the whole world as novel cancer therapy drug from being found to, and people have bet huge energy, and each details of separation and purification process has all been carried out detailed research, the progressively perfect requirement of production technique.At present the extraction and purification process of taxol has solvent extration, Solid-Phase Extraction, chromatography, membrane separation process, supercritical extraction, ion exchange method, key compound dissociate method and chemical reaction method.The shortcoming that these technologies exist mostly is: yield is low, technical process is long, throughput is little etc.
More existing technologies are mostly delivered with the form of patent.Young has described a semipreparative production technique of taxol, and process comprises carries out methanol extraction to bark dry powder, concentrates the back dilute with water, then with chloroform mixing phase-splitting; The chloroform phase dehydration, evaporated under reduced pressure; Load on the semipreparative normal phase silicagel column methylene dichloride/acetone gradient elution: the cut that contains taxol is once more through a semipreparative normal-phase chromatography process, and elutriant changes normal hexane/Virahol/methyl alcohol into and carries out the constant speed wash-out; Can obtain a small amount of pure product of paclitaxel at last.This technology is just carried out as a research, and the process scale is less, and the pattern and the result of gradient elution wherein also has been discussed.A technological process, isolation of taxol from the T.brevifolia bark have been described at U.S. Pat P5475120 by Polyscience company.Process comprises: methyl alcohol or alcohol extraction bark, extraction liquid concentrate removes most of organic alcohol; The concentrated solution dichloromethane extraction, the extraction liquid concentrate drying is to powder; Powder juice dissolves with acetone and Li Geluoyin (1: 1), and indissolvable component removes by filter; Filtrate the concentrating of containing taxol is dissolved in acetone-Li Geluoyin solution of 30%, filters through the Florisfi post; Effusive taxol component crystallization purifying is twice from post; The crystalline taxol further separates in silicagel column, and in this step, the most close analogue Cephalomannine separates from taxol; Effusive taxol recrystallize is twice from post; Unsegregated mixture and other solutes, circular treatment obtains pure taxol.This technology does not add any processing, and directly with the silicagel column isolation of taxol with support, solvent-oil ratio is big, the shortcoming that separation cycle is also long.
In some initial separating technologies of taxol, chromatographic process adopts positive usually.Along with going deep into of research, in recent years, the separation and purification that many reversed-phase preparative chromatography technologies are used for taxol has appearred, wherein graduate Liu of Beijing chemical industry metallurgical open record and the work of Yang Xuefeng very representative, 1996, reported with the fix technological process of phase reverse phase separation purification of paclitaxel of a class multi-hole type vinylbenzene one dialkylene benzene polymer microsphere, the moving phase of selecting is acetone or methanol, gradient elution, can make taxol (purity surpasses 99%, and yield is higher than 80%) and some other similar substance block prosperous IIIe cephalomannine etc. with the three step post looks processes of diving and obtain purifying as crust.This method selectivity is good, but a shortcoming that is difficult to overcome is still arranged in their technology, is exactly that cost is too high, about 1 ton/200,000 yuan of used fixed phase stuffing.Improve in correlation technique, the cost of manufacture of polymer carrier is expected to realize industrialized production after reducing.Similar simultaneously, Lu Dayan etc. have studied with the fix technological process of reversed phase chromatography separation purification of paclitaxel of phase of gac.A United States Patent (USP) in 1999 has been reported and has a kind ofly been composed and separate pure process with the Phenylalkyl chromatographic grade resin relative taxanes material that fixes, the purity of taxol can surpass 98.5%, in addition, 10-deactyltaxol, 7-e-taxol, cephalomannine, baccatin III, crust Bu Ting V, 7-epi-DAB, DAB and 9-dihydro-13-acetylbaccat i nIII (DIIB) etc. can obtain purifying simultaneously.Though the technology of reversed phase chromatography separation purification of paclitaxel does not still have industrialized report at present, relative and normal-phase chromatography technology, reverse-phase chromatography technology, reverse-phase chromatography has lot of advantages undoubtedly.At first, it does not consume a large amount of organic solvents, and environmental pollution is less; And people advance some specific bonding phases of special introducing in the exploitation reverse phase filler, make reverse phase filler that better choice be arranged, and cause the target product rate of recovery also very valuable aspect low in the irreversible adsorption that overcomes purification on normal-phase silica gel.Therefore, the technology of researching and developing a kind of simple and convenient, product rate of recovery height, preparation taxol in enormous quantities with low cost has realistic meaning really very much.
Summary of the invention:
The method that the purpose of this invention is to provide a kind of separating and purifying taxol efficiently is for preparation taxol in enormous quantities provides that a kind of technology is simple and convenient, product rate of recovery height, novel method with low cost.
Technological process of the present invention is:
-extraction is the extract that raw material obtains to contain taxol with the Ramulus et folium taxi cuspidatae;
-remove colloid, remove the colloid impurity in the extract;
-separation and purification is characterized in that removing the gelationus process and is:
-high pressure silica gel column chromatography column chromatography is removed colloid, simultaneously taxane compounds is separated into taxol, Cephalomannine, 7-Epitaxol 3 parts.Content of taxol 〉=99.5%, the Cephalomannine content that uses present method preparation is 0.15%, 7-Epitaxol content is 0.10%.
Among the preparation method of paclitaxel extract of the present invention, with the bark of Ramulus et folium taxi cuspidatae after pulverizing is raw material, spill smart 35-55 ℃ of thermal backflow lixiviate 3 times through 80%～95%, 50-70 ℃ of vacuum decompression is concentrated into heat and surveys the extract that proportion 1.1～1.2g/ml chloroform extraction obtains to contain taxol.
Removing in the assorted method of colloid in the paclitaxel extract of the present invention, content of taxol is the sample of 5-25%, high pressure silica gel column chromatography column chromatography, with ethyl acetate one hexanaphthene wash-out, target compound taxol section cut concentrate drying, acetone-sherwood oil crystallization 3 times, suction filtration, it is 65% taxol that 50 ℃ of vacuum decompression dryings obtain purity, and the taxol yield reaches 80%.
Removing in the assorted method of colloid in the paclitaxel extract of the present invention, high pressure silica gel column chromatography column chromatography is meant silica gel: the 200-300 order, material glue is than 1: 6-6: 1, wash-out pressure 10-20MPa.
Removing in the assorted method of colloid in the paclitaxel extract of the present invention, the column chromatography wash-out is a gradient elution, or etc. the degree stepwise elution, ethyl acetate one hexanaphthene is an eluent.During Deng degree stepwise elution, the concentration difference with 10% is a spacer, and every section elution volume is a 2-3 column volume, eluent flow rate be 1-2 column volume/hour.
Among the preparation method of taxol of the present invention, separate taxane compounds and press dry weight calculating adding analytical pure acetone, heating for dissolving is complete, and at the uniform velocity whipped state adds down the analytical pure sherwood oil, reaches 1 ° of muddy state to solution, 50 ℃ of heating, leave standstill after-filtration, xln washs 2 times at least with acetone-sherwood oil mixing solutions, drains, vacuum-drying, product through HPLC detect that content of taxol reaches 99.5%, Cephalomannine content is 0.15%, 7-Epitaxol content is 0.10%.
The taxol production process is seen accompanying drawing:
Advantage of the present invention is: the technology that the invention provides a kind of simple and convenient, product rate of recovery height, preparation taxol in enormous quantities with low cost.
Description of drawings:
Fig. 1 is a process flow sheet of the present invention.
Embodiment
Embodiment 1: the extract that obtains 1% content of taxol
Bark of Ramulus et folium taxi cuspidatae airing (moisture content 12%), take by weighing the bark fines 500kg behind the crushing screening (40 order), 3 times (2500L * 1,1800L * 2,12hr * 3) are extracted in 55 ℃ of thermal cyclings of 95 ° of alcohol, merge 3 times alcoholic extract, (vacuum tightness-0.05Mpa-0.06MPa) is concentrated into 100L alcohol extracting cream for 60 ℃ of vacuum decompressions, chloroform extraction 3 times (100L * 3,4hr * 3), merge 3 times chloroform extraction liquid, normal pressure is concentrated into the semi-fluid shape, 45 ℃ of dryings, obtain pressed powder 6.8kg, content of taxol 1.02%.
The removal of embodiment 2. pigment impurity obtains content of taxol 5-8% work in-process
Pressed powder 6.8kg adds chloroform 20L dissolving fully after the chloroform extraction drying, adds 100-200 order silica gel 15.6kg stirring and evenly mixing, 40 ℃ of dry 48hr (every 4hr stirs once in the process), chromatography column on the material glue of dry back (silicon school 4.7kg, φ 216mm * 1500mm).Methyl alcohol one 0%-2% of chloroform system (V/V) gradient elution (flow velocity 85-100ml/min), Fractional Collections (every section 4-5L), branch merges (merging by preceding impurity, taxol/Cephalomannine, three parts of rear impurity) after TLC detects, (vacuum tightness-0.01Mpa-0.02MPa) concentrates and reclaims chloroform and methyl alcohol taxol/60 ℃ of vacuum decompressions of Cephalomannine part, get enriched material 912g, content of taxol 7.6%.
Embodiment 3. gummy class Impurity removals obtain content of taxol 20-25% work in-process
The enriched material 912g of content of taxol 7.6% adds acetone 2700ml dissolving fully, add 100-200 order silica gel 1.8kg stirring and evenly mixing, 40 ℃ of dry 48hr (every 4hr stirs once in the process), chromatography column (200-300 order silica gel 7.3kg on the material glue of dry back, φ 200mm * 1500mm), 25-35% (v/v) acetone one sherwood oil gradient elution (flow velocity 60-80ml/min), Fractional Collections (every section 3.5-4L), branch merges (presses preceding impurity after TLC detects, taxol/Cephalomannine, three parts of rear impurity merge), (vacuum tightness-0.04Mpa-0.05MPa) concentrates and reclaims acetone-sherwood oil taxol/60 ℃ of vacuum decompressions of Cephalomannine part, get enriched material 289g, content of taxol 23%.
Embodiment 4. crystallization process initial gross separation taxol and Cephalomannines
Content of taxol 23% enriched material 289g adds 50 ℃ of dissolvings of 2000ml acetone fully, and it is muddy to occurring to add sherwood oil under stirring, and room temperature leaves standstill crystallization 24hr.Filter the back and repeat 0 ℃ of vacuum-drying 48hr of white powder crystal 5 of obtaining after the crystallization 2 times, obtain taxol work in-process 83g, content of taxol 76%.
Embodiment 5. taxols separate, crystallization purifying
Content of taxol 76% work in-process 83g goes up high pressure chromatography column (silica gel 10-40u, pressure 16MPa), gradient elution, branch merges (presses the 7-Epitaxol after TCL detects, taxol, three parts of Cephalomannine merge), 60 ℃ of vacuum decompressions of taxol part (vacuum tightness-O.06MPa～-O.08MPa) concentrate and reclaim solvent, the enriched material 63g that obtains adds 660ml analytical pure acetone, 50 ℃ of heating for dissolving are complete, at the uniform velocity whipped state adds 50 ℃ of analytical pure sherwood oil (60 ℃～90 ℃ of sherwood oil boiling ranges down, the about 500ml/min of preceding 95% sherwood oil adding speed, the about 200ml/min of back 4% sherwood oil amount adding speed, drip 1% sherwood oil amount at last) reach 1 ° of muddy state to solution, 50 ℃ were heated 30 seconds, leave standstill filtration in 8 hours, xln washs 2 times with acetone-sherwood oil mixing solutions of 80ml 30%, drain, (vacuum tightness-0.08MPa) drying got paclitaxel prodrugs 60g in 96 hours to 50 ℃ of vacuum, and product detects content of taxol through HPLC and reaches 99.5%, Cephalomannine content 0.15%, 7-Epitaxol content 0.10%.
Claims (9)
1, a kind of method of separating and purifying taxol efficiently, it comprises a, extraction, is the extract that raw material obtains to contain taxol with the Ramulus et folium taxi cuspidatae; B, removal colloid are removed the colloid impurity in the extract; C, separation and purification; It is characterized in that: the taxol production technique is as follows:
Bark of Ramulus et folium taxi cuspidatae is pulverized, 85%～95% alcohol 35-55 ℃ thermal backflow lixiviate three times, 50-70 ℃ of vacuum decompression is concentrated into heat and surveys proportion 1.1～1.2g/ml, chloroform extraction, extraction liquid is condensed into paste, get content of taxol 1% chloroform cream, content of taxol 1% chloroform cream is added the chloroform dissolving fully, add silica gel and stir, airing, sieve, be filled in the chromatography column, the chloroform-methanol gradient elution, TLC detects, segmentation merges concentrated, get content of taxol 5～8% work in-process, it is complete that content of taxol 5～8% work in-process are added acetone solution, adds silica gel and stir, airing, sieve, be filled in the chromatography column, acetone-sherwood oil gradient elution, TLC detects, segmentation merge to concentrate, content of taxol 20～25% work in-process, with acetone-sherwood oil system crystallization 3～4 times, suction filtration, 50 ℃ of vacuum decompression dryings get content of taxol 75～80% work in-process, 16Mpa pressure chromatographic separation, TLC detects, segmentation merges concentrated, target phase enriched material acetone-sherwood oil crystallization, suction filtration, drying gets content of taxol 〉=99.5% finished product;
Removing the gelationus process is: high pressure silica gel column chromatography column chromatography is removed colloid, simultaneously taxane compounds is separated into taxol, Cephalomannine, 7-Epitaxol 3 parts.Content of taxol 〉=99.5%, the Cephalomannine content that uses present method preparation is 0.15%, 7-Epitaxol content is 0.10%.
2, the method for a kind of separating and purifying taxol efficiently according to claim 1, it is characterized in that: the method for removing the colloid impurity in the extract is, extract is that content of taxol is the sample of 5-25%, high pressure silica gel column chromatography column chromatography, with ethyl acetate one hexanaphthene wash-out, target compound taxol section cut concentrate drying, acetone-sherwood oil crystallization 3 times, it is 65% taxol that suction filtration, 50 ℃ of vacuum decompression dryings obtain purity, and the taxol yield reaches 80%.
3, the method for a kind of separating and purifying taxol efficiently according to claim 1 and 2 is characterized in that: described high pressure silica gel column chromatography column chromatography is meant silica gel: the 200-300 order, and material glue is than 1: 6-6: 1, wash-out pressure 10-20Mpa.
4, the method for a kind of separating and purifying taxol efficiently according to claim 1 and 2 is characterized in that: described column chromatography wash-out is a gradient elution, or etc. the degree stepwise elution, ethyl acetate one hexanaphthene is an eluent.
5, the method for a kind of separating and purifying taxol efficiently according to claim 3, it is characterized in that: when described column chromatography wash-out is stepwise elution such as degree such as grade, concentration difference with 10% is a spacer, and every section elution volume is a 2-3 column volume, eluent flow rate be 1-2 column volume/hour.
6, the method of a kind of separating and purifying taxol efficiently according to claim 1, it is characterized in that: separate taxane compounds, press dry weight and calculate adding analytical pure acetone, heating for dissolving is complete, at the uniform velocity whipped state adds the analytical pure sherwood oil down, reach 1 ° of muddy state to solution, 50 ℃ of heating, leave standstill after-filtration, xln washs 2 times at least with acetone-sherwood oil mixing solutions, drains, vacuum, vacuum tightness-0.08Mpa, drying, product detects content of taxol through HPLC and reaches 99.5%, Cephalomannine content is 0.15%, 7-Epitaxol content is 0.10%.
7, the method for a kind of separating and purifying taxol efficiently according to claim 6 is characterized in that: described separation taxane compounds, and press dry weight and calculate adding analytical pure acetone, add-on 8-12 doubly measures (G/V), the heating for dissolving temperature is 40-60 ℃.
8, the method for a kind of separating and purifying taxol efficiently according to claim 6, it is characterized in that: described separation taxane compounds, the temperature that at the uniform velocity adds the analytical pure sherwood oil under the whipped state is 40-60 ℃, the adding mode is the about 400-600ml/min of preceding 95% sherwood oil amount adding speed, the about 100-300ml/min of back 4% sherwood oil amount adding speed, drip 0.5-1.5% sherwood oil amount at last, time of repose is 6-10 hour.
9, the method for a kind of separating and purifying taxol efficiently according to claim 6, it is characterized in that: described separation taxane compounds, the volume ratio 1 of acetone-sherwood oil mixing solutions: 5-5: 10V/V, xln are doubly measured washing with the 1-3 of acetone-sherwood oil mixing solutions, and the vacuum-drying time is 72-108 hour.
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| CN101254217B (en) * | 2008-04-14 | 2010-09-01 | 梅州市中大南药发展有限公司 | Preparation of extract of regeneratabl portion of yew and applications of same for preparing oral anti-cancer medicine |
| CN102250047A (en) * | 2011-08-26 | 2011-11-23 | 贺金凤 | More-stable taxol compound and medicament composition thereof |
| CN102838568A (en) * | 2012-07-26 | 2012-12-26 | 吉林派高生物制药有限公司 | Method for extraction of paclitaxel from taxus chinensis |
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| CN103275039A (en) * | 2013-06-21 | 2013-09-04 | 江苏红豆杉药业有限公司 | Method for separation and purification of taxol from taxol extract |
| CN103819430A (en) * | 2014-02-25 | 2014-05-28 | 河南省科学院化学研究所有限公司 | Paclitaxel purifying method of paclitaxel crude product produced by Chinese yew cell culture |
| CN105315242A (en) * | 2015-11-17 | 2016-02-10 | 重庆臻源红豆杉发展有限公司 | Removal method of colloid and pigment in crude paclitaxel product |
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| CN111393390A (en) * | 2019-01-02 | 2020-07-10 | 贵州罗贝罗生物科技有限公司 | Method for efficiently extracting paclitaxel from taxus chinensis |
| CN113512015A (en) * | 2021-05-26 | 2021-10-19 | 上海卓鼎生物技术有限公司 | Method for industrially purifying cephalomannine |
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| CN102250047A (en) * | 2011-08-26 | 2011-11-23 | 贺金凤 | More-stable taxol compound and medicament composition thereof |
| CN102250047B (en) * | 2011-08-26 | 2013-06-05 | 贺金凤 | Preparation method of taxol compound |
| CN102838568A (en) * | 2012-07-26 | 2012-12-26 | 吉林派高生物制药有限公司 | Method for extraction of paclitaxel from taxus chinensis |
| CN103203122B (en) * | 2012-10-09 | 2015-09-09 | 殷美芳 | By the method for liquid-phase chromatographic column separating-purifying high-purity natural biology from animals and plants |
| CN103203122A (en) * | 2012-10-09 | 2013-07-17 | 殷美芳 | Method for separating and purifying high-purity natural substances from animals and plants by using liquid chromatography column |
| CN102942455A (en) * | 2012-11-26 | 2013-02-27 | 苏州农业职业技术学院 | Method for extracting oxyresveratrol from mulberry branches |
| CN102942455B (en) * | 2012-11-26 | 2014-08-13 | 苏州农业职业技术学院 | Method for extracting oxyresveratrol from mulberry branches |
| CN103232417A (en) * | 2013-05-14 | 2013-08-07 | 江苏斯威森生物医药工程研究中心有限公司 | Method for extracting, separating and purifying paclitaxel |
| CN103275039A (en) * | 2013-06-21 | 2013-09-04 | 江苏红豆杉药业有限公司 | Method for separation and purification of taxol from taxol extract |
| CN103275039B (en) * | 2013-06-21 | 2015-03-25 | 江苏红豆杉药业有限公司 | Method for separation and purification of taxol from taxol extract |
| CN103819430A (en) * | 2014-02-25 | 2014-05-28 | 河南省科学院化学研究所有限公司 | Paclitaxel purifying method of paclitaxel crude product produced by Chinese yew cell culture |
| CN105315242A (en) * | 2015-11-17 | 2016-02-10 | 重庆臻源红豆杉发展有限公司 | Removal method of colloid and pigment in crude paclitaxel product |
| CN105457337A (en) * | 2015-11-17 | 2016-04-06 | 重庆臻源红豆杉发展有限公司 | A silica gel loading and sample loading method of a chromatographic column |
| CN111393390A (en) * | 2019-01-02 | 2020-07-10 | 贵州罗贝罗生物科技有限公司 | Method for efficiently extracting paclitaxel from taxus chinensis |
| CN113512015A (en) * | 2021-05-26 | 2021-10-19 | 上海卓鼎生物技术有限公司 | Method for industrially purifying cephalomannine |
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