CN101613390A - A method for separating and purifying high-purity cordycepin - Google Patents
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- 238000000034 method Methods 0.000 title claims abstract description 38
- KQLDDLUWUFBQHP-UHFFFAOYSA-N Cordycepin Natural products C1=NC=2C(N)=NC=NC=2N1C1OCC(CO)C1O KQLDDLUWUFBQHP-UHFFFAOYSA-N 0.000 title claims abstract description 35
- OFEZSBMBBKLLBJ-BAJZRUMYSA-N cordycepin Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)C[C@H]1O OFEZSBMBBKLLBJ-BAJZRUMYSA-N 0.000 title claims abstract description 35
- OFEZSBMBBKLLBJ-UHFFFAOYSA-N cordycepine Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(CO)CC1O OFEZSBMBBKLLBJ-UHFFFAOYSA-N 0.000 title claims abstract description 35
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 66
- 241001264174 Cordyceps militaris Species 0.000 claims abstract description 19
- 239000007788 liquid Substances 0.000 claims abstract description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000013078 crystal Substances 0.000 claims abstract description 12
- 239000012535 impurity Substances 0.000 claims abstract description 11
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- 238000000855 fermentation Methods 0.000 claims abstract description 10
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- 238000001556 precipitation Methods 0.000 claims abstract description 6
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- 150000004676 glycans Chemical class 0.000 claims description 5
- 229920001282 polysaccharide Polymers 0.000 claims description 5
- 239000005017 polysaccharide Substances 0.000 claims description 5
- 238000010828 elution Methods 0.000 claims description 4
- 238000005057 refrigeration Methods 0.000 claims description 4
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- 238000011068 loading method Methods 0.000 claims description 2
- 239000000463 material Substances 0.000 claims description 2
- 230000007935 neutral effect Effects 0.000 claims description 2
- 102000004169 proteins and genes Human genes 0.000 claims description 2
- 108090000623 proteins and genes Proteins 0.000 claims description 2
- 238000011084 recovery Methods 0.000 claims description 2
- 238000002425 crystallisation Methods 0.000 claims 1
- 230000008025 crystallization Effects 0.000 claims 1
- 238000000926 separation method Methods 0.000 abstract description 9
- 239000012141 concentrate Substances 0.000 abstract description 5
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 241000190633 Cordyceps Species 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- YMTINGFKWWXKFG-UHFFFAOYSA-N fenofibrate Chemical compound C1=CC(OC(C)(C)C(=O)OC(C)C)=CC=C1C(=O)C1=CC=C(Cl)C=C1 YMTINGFKWWXKFG-UHFFFAOYSA-N 0.000 description 2
- 229960002297 fenofibrate Drugs 0.000 description 2
- 239000003456 ion exchange resin Substances 0.000 description 2
- 229920003303 ion-exchange polymer Polymers 0.000 description 2
- NPBDKJFSWDGCHA-CGLBFHKCSA-N (2R,3R,5S)-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolan-3-ol Chemical compound [C@@H]1([C@H](O)C[C@@H](CO)O1)N1C=NC=2C(N)=NC=NC12.[C@@H]1([C@H](O)C[C@@H](CO)O1)N1C=NC=2C(N)=NC=NC12 NPBDKJFSWDGCHA-CGLBFHKCSA-N 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
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- 239000002253 acid Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- RJGDLRCDCYRQOQ-UHFFFAOYSA-N anthrone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3CC2=C1 RJGDLRCDCYRQOQ-UHFFFAOYSA-N 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
一种高纯度虫草菌素分离纯化的方法，涉及从蛹虫草发酵液中分离提纯高纯度虫草菌素的方法。该方法是以蛹虫草发酵液为原料，真空浓缩后，加乙醇至80％～90％进行醇沉，提取蛹虫草发酵液中虫草菌素；之后过滤，滤液真空回收乙醇，再加水稀释后，上大孔树脂柱进行分离；上柱后先用水洗杂质，再用低浓度乙醇洗脱收集洗脱液；将洗脱液浓缩至干，采用乙醇溶解并冷藏结晶，即得虫草菌素粗晶体，采用乙醇多次重结晶，即得高纯度虫草菌素晶体。本发明方法可以从蛹虫草发酵液制备纯度大于98％的高纯度虫草菌素，具有工艺流程简单、产品质量好、以及工业化生产成本低、可直接作为医药工业的原料等优点。A method for separating and purifying high-purity cordycepin relates to a method for separating and purifying high-purity cordycepin from fermentation liquid of Cordyceps militaris. The method uses Cordyceps militaris fermented liquid as raw material, after vacuum concentration, adding ethanol to 80%-90% for alcohol precipitation, extracting cordycepin in the Cordyceps militaris fermented liquid; after that, filtering, ethanol is recovered from the filtrate in vacuum, and diluted with water, Put it on a macroporous resin column for separation; after putting it on the column, wash the impurities with water, and then elute with low-concentration ethanol to collect the eluate; concentrate the eluate to dryness, dissolve it in ethanol and refrigerate to crystallize to obtain coarse crystals of cordycepin , using ethanol for multiple recrystallizations to obtain high-purity cordycepin crystals. The method of the invention can prepare high-purity cordycepin with a purity greater than 98% from the fermentation liquid of Cordyceps militaris, and has the advantages of simple process flow, good product quality, low industrial production cost, and can be directly used as a raw material in the pharmaceutical industry.
Description
技术领域 technical field
本发明属于医药工业领域，具体而言涉及从蛹虫草发酵液中分离提纯高纯度虫草菌素的方法。The invention belongs to the field of pharmaceutical industry, and in particular relates to a method for separating and purifying high-purity cordycepin from fermentation liquid of Cordyceps militaris.
背景技术 Background technique
虫草菌素即3′-脱氧腺苷(3′-Deoxyadenosine)，又称蛹虫草菌素、虫草素，由Cunningham等于1951年从蛹虫草的培养滤液中分离得到。虫草菌素是第一个从真菌中分离出来的核苷类抗菌素。虫草菌素的分子式为C10H13N5O3，分子量251，碱性，针状或片状结晶，熔点230℃～231℃，溶于水、热乙醇和甲醇，不溶于苯、乙醚和氯仿，蒽酮反应阳性，紫外光最大吸收波长为259nm。虫草菌素具有多种生物学活性，比如抑菌作用、抗肿瘤作用、抑制人体免疫缺陷病毒HIVI型病毒的作用、免疫调节作用、减肥、降血糖和降血脂作用。其中，降血脂方面的效果尤为明显，与市售的非诺贝特(法国力博福尼制药公司生产)效果相当或优于非诺贝特；在治疗白血病方面也在美国由FDA批准进入了临床研究(1997年11月美国癌症研究所，2008年7月美国OncoVista公司)。Cordycepin is 3'-deoxyadenosine (3'-Deoxyadenosine), also known as cordycepin and cordycepin, which was isolated from the culture filtrate of Cordyceps militaris by Cunningham et al. in 1951. Cordycepin is the first nucleoside antibiotic isolated from fungi. The molecular formula of cordycepin is C 10 H 13 N 5 O 3 , molecular weight 251, alkaline, needle-like or flaky crystal, melting point 230℃～231℃, soluble in water, hot ethanol and methanol, insoluble in benzene, ether and Chloroform and anthrone react positively, and the maximum absorption wavelength of ultraviolet light is 259nm. Cordycepin has a variety of biological activities, such as antibacterial effect, anti-tumor effect, inhibitory effect of human immunodeficiency virus HIVI virus, immune regulation effect, weight loss, hypoglycemic and hypolipidemic effect. Among them, the effect of reducing blood lipid is particularly obvious, and is equivalent to or better than fenofibrate in effect with commercially available fenofibrate (produced by French Liboforni Pharmaceutical Company); Clinical research (November 1997 American Cancer Institute, July 2008 American OncoVista Corporation).
目前国内外对虫草菌素分离纯化工艺进行了积极的研究，并取得了一定进展。其中大多数都采用离子交换树脂吸附法进行分离纯化，例如中国专利申请件00134688.1号“一种虫草素的提纯方法”、200710122409.0号“从蛹虫草中提取精制虫草素和虫草多糖的方法”、200810069244.X号“北冬虫夏草菌丝体中多种有效成分的综合提取方法”，离子交换树脂吸附法需要用酸碱处理，后处理比较复杂，且分离纯化工艺相对较复杂，成本较高，难以进行大规模工业化生产。分离提取工艺中涉及到大孔吸附树脂的仅有专利申请件200710170485.9号“一种虫草素的分离纯化方法”，该技术仅将大孔吸附树脂(NKA-II型)用于虫草菌素的初步富集(纯度仅达到10％)，然后采用C18柱对其进行进一步纯化，使其纯度达到95.2％；即大孔吸附树脂在工艺过程中只起到除杂和富集的作用，并未起到真正的纯化作用，C18柱的应用增加了工艺流程，使整个分离纯化工艺相对复杂、得率降低、成本较高、纯度不高、难以适应大规模生产。At present, the separation and purification process of cordycepin has been actively studied at home and abroad, and some progress has been made. Most of them are separated and purified by ion exchange resin adsorption method, such as Chinese Patent Application No. 00134688.1 "A Purification Method for Cordycepin", No. 200710122409.0 "Method for Extracting Refined Cordycepin and Cordyceps Polysaccharide from Cordyceps Militaris", No. 200810069244 .X No. "Comprehensive Extraction Method of Various Active Components in Mycelium of Cordyceps militaris", the ion exchange resin adsorption method needs to be treated with acid and alkali, the post-treatment is more complicated, and the separation and purification process is relatively complicated, the cost is high, and it is difficult to carry out large-scale industrial production. The only patent application No. 200710170485.9 "a method for separation and purification of cordycepin" involving macroporous adsorption resin in the separation and extraction process, this technology only uses macroporous adsorption resin (NKA-II type) for the preliminary preparation of cordycepin Enrichment (purity only reaches 10%), and then it is further purified by C18 column to make its purity reach 95.2%; that is, the macroporous adsorption resin only plays the role of impurity removal and enrichment in the process, and does not To achieve the real purification effect, the application of C18 column increases the process flow, which makes the whole separation and purification process relatively complicated, the yield is reduced, the cost is high, the purity is not high, and it is difficult to adapt to large-scale production.
发明内容 Contents of the invention
本发明的目的在于提供一种高纯度虫草菌素分离纯化的简便方法，即适合工业化生产的从蛹虫草发酵液中分离纯化虫草菌素的方法，以解决现有技术中流程复杂、得率低、分离纯化选择性差、以及工业化生产成本高、不适宜直接用于医药原料的缺点。The purpose of the present invention is to provide a simple method for the separation and purification of high-purity cordycepin, that is, a method for separating and purifying cordycepin from the fermentation liquid of Cordyceps militaris that is suitable for industrial production, so as to solve the complex process and low yield in the prior art , poor separation and purification selectivity, and high industrial production costs, not suitable for direct use in pharmaceutical raw materials.
本发明是通过以下方案来实施的：以蛹虫草发酵液为原料，真空浓缩后，加乙醇至80％～90％进行醇沉，提取蛹虫草发酵液中虫草菌素；之后过滤，滤液真空回收乙醇，再加水稀释后，上大孔树脂柱进行分离；上柱后先用水洗杂质，再用低浓度乙醇洗脱收集洗脱液；将洗脱液浓缩至干，采用乙醇溶解并冷藏结晶，即得虫草菌素粗晶体，采用乙醇多次重结晶，即得高纯度虫草菌素晶体。The present invention is implemented through the following scheme: use Cordyceps militaris fermented liquid as raw material, after vacuum concentration, add ethanol to 80%-90% for alcohol precipitation, extract cordycepin in Cordyceps militaris fermented liquid; then filter, and vacuum recover the filtrate After diluting with ethanol and adding water, it is separated on a macroporous resin column; after being loaded on the column, the impurities are washed with water, and then eluted with low-concentration ethanol to collect the eluate; the eluate is concentrated to dryness, dissolved in ethanol and refrigerated to crystallize. The coarse crystals of cordycepin are obtained, and the crystals of high-purity cordycepin are obtained by repeated recrystallization with ethanol.
上述浓缩过程中，所述真空浓缩的真空度为0.08MPa。During the above concentration process, the vacuum degree of the vacuum concentration is 0.08MPa.
上述醇沉过程中，所述用来提取蛹虫草发酵液虫草菌素的乙醇体积分数为70％～90％，用量为物料的1∶10～1∶15，以去除发酵液中蛋白及多糖等水溶性杂质。In the above-mentioned alcohol precipitation process, the volume fraction of ethanol used to extract cordycepin from the Cordyceps militaris fermentation liquid is 70% to 90%, and the dosage is 1:10 to 1:15 of the material, so as to remove proteins and polysaccharides in the fermentation liquid. water soluble impurities.
上述过滤过程中，所述滤液回收的真空度控制在0.08MPa。During the above-mentioned filtration process, the vacuum degree of the filtrate recovery is controlled at 0.08MPa.
上述上柱过程中，所述加水稀释时水的用量为1∶20；所述分离纯化蛹虫草发酵液虫草菌素的大孔树脂型号为AB-8及DM-130。In the above column loading process, the amount of water used for diluting with water is 1:20; the models of the macroporous resins for separating and purifying cordycepin from the fermentation liquid of Cordyceps militaris are AB-8 and DM-130.
上述洗脱过程中，所述用于除杂的蒸馏水为中性，水的用量为2倍柱体积；所述用于洗脱的乙醇浓度为20％～30％，用量为3～4倍柱体积。In the above elution process, the distilled water used for removing impurities is neutral, and the consumption of water is 2 times column volume; the ethanol concentration used for elution is 20% to 30%, and the consumption is 3 to 4 times column volume. volume.
上述冷藏和重结晶过程中，所述冷藏温度为2℃～6℃；所述重结晶的次数为3次。During the above refrigeration and recrystallization process, the refrigeration temperature is 2° C. to 6° C.; the number of recrystallizations is 3 times.
本发明方法可以从蛹虫草发酵液制备纯度大于98％的高纯度虫草菌素，具有工艺流程简单、产品质量好、以及工业化生产成本低、可直接作为医药工业的原料等优点。The method of the invention can prepare high-purity cordycepin with a purity greater than 98% from the fermentation liquid of Cordyceps militaris, and has the advantages of simple process flow, good product quality, low industrial production cost, and can be directly used as a raw material in the pharmaceutical industry.
具体实施方式 Detailed ways
以下实例可以进一步说明本发明：The following examples can further illustrate the present invention:
实施例1Example 1
第一步，取蛹虫草发酵液1L，在真空度0.08MPa下浓缩至150mL；In the first step, take 1L of Cordyceps militaris fermented liquid and concentrate it to 150mL under a vacuum of 0.08MPa;
第二步，加乙醇至溶液中乙醇浓度至80％进行醇沉，过滤以除去多糖及其他杂质，滤液真空回收乙醇，再加水稀释后备用；In the second step, add ethanol until the concentration of ethanol in the solution reaches 80%, carry out alcohol precipitation, filter to remove polysaccharides and other impurities, recover the ethanol from the filtrate in a vacuum, add water to dilute and set aside;
第三步，溶液上大孔树脂柱，用型号为AB-8及DM-130的树脂进行动态吸附分离，先用2倍柱体积水洗杂质，再用25％乙醇洗脱并收集洗脱液。In the third step, the solution is put on a macroporous resin column, and the resins of AB-8 and DM-130 are used for dynamic adsorption separation. The impurities are first washed with 2 times the column volume, then eluted with 25% ethanol and collected.
第四步，将洗脱液浓缩至干，采用料液比1∶20加95％乙醇溶解并冷藏结晶，即得虫草菌素粗晶体，然后3次重结晶，即得高纯度98.5％虫草菌素晶体0.15g。The fourth step is to concentrate the eluent to dryness, dissolve it with 95% ethanol at a solid-to-liquid ratio of 1:20, and refrigerate and crystallize to obtain coarse crystals of cordycepin, and then recrystallize three times to obtain high-purity 98.5% Cordyceps fungus Plain crystal 0.15g.
实施例2Example 2
第一步，取蛹虫草发酵液1L，在真空度0.08MPa下真空浓缩至干；In the first step, take 1L of Cordyceps militaris fermented liquid, and vacuum-concentrate to dryness under a vacuum degree of 0.08MPa;
第二步，用90％乙醇超声溶解，抽滤以除去多糖及其他杂质，滤液真空回收乙醇，再加水溶解后备用。In the second step, 90% ethanol is used for ultrasonic dissolution, and the polysaccharide and other impurities are removed by suction filtration. The filtrate is vacuum-recovered for ethanol, and then dissolved in water for further use.
第三步，溶液上处理好的大孔树脂柱，用型号为AB-8及DM-130的树脂进行动态吸附分离，流速1倍柱体积/h，先用2倍柱体积水洗杂质，再用3倍柱体积30％乙醇洗脱并收集洗脱液。In the third step, the macroporous resin column that has been treated on the solution is dynamically adsorbed and separated with resins of type AB-8 and DM-130, and the flow rate is 1 times the column volume/h. 3 times column volume 30% ethanol was eluted and the eluate was collected.
第四步，将洗脱液浓缩至干，采用95％乙醇溶解并冷藏结晶，即得虫草菌素粗晶体，采用体积分数为95％乙醇3次重结晶，即得高纯度虫草菌素晶体98.2％虫草菌素晶体0.13g。The fourth step is to concentrate the eluent to dryness, dissolve it in 95% ethanol and refrigerate and crystallize it to obtain the crude crystal of cordycepin, and use 95% ethanol to recrystallize it three times to obtain the high-purity cordycepin crystal 98.2 % cordycepin crystal 0.13g.
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Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102432656A (en) * | 2011-12-23 | 2012-05-02 | 辽宁省农业科学院大连生物技术研究所 | A method for extracting and purifying cordycepin from fruiting bodies of Cordyceps militaris |
| CN102936271A (en) * | 2012-11-14 | 2013-02-20 | 石家庄藏诺生物股份有限公司 | Method for extracting cordycepin |
| CN103751225A (en) * | 2014-01-27 | 2014-04-30 | 正源堂（天津）生物科技有限公司 | Method for extracting antitumor active ingredients of cordyceps militaris and application thereof |
| CN103766545A (en) * | 2014-01-02 | 2014-05-07 | 隋新 | Preparation method of cordyceps militaris extractive-rich cordyceps militaris tea |
| CN103784481A (en) * | 2014-01-27 | 2014-05-14 | 正源堂（天津）生物科技有限公司 | Method for extracting anti-tumor active component from Cordyceps militaris and application of active component |
| CN104788521A (en) * | 2015-03-24 | 2015-07-22 | 北京电子科技职业学院 | Method for rapidly separating cordycepin from fermentation broth |
| CN105037469A (en) * | 2015-06-24 | 2015-11-11 | 中山鼎晟生物科技有限公司 | A kind of extraction method of cordycepin in submerged fermentation broth of Cordyceps militaris |
| CN105646627A (en) * | 2015-12-17 | 2016-06-08 | 常熟浸大科技有限公司 | Method for extracting purified cordycepin from cordyceps militaris nutrient solution |
| CN108490864A (en) * | 2018-04-12 | 2018-09-04 | 中国船舶重工集团公司第七0三研究所 | Intelligent production flexibility route control system |
| CN113233970A (en) * | 2021-05-18 | 2021-08-10 | 山东国力生物技术研究院 | Preparation method of high-purity hypocrellin |
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2009
- 2009-07-21 CN CN200910102682A patent/CN101613390A/en active Pending
Cited By (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102432656B (en) * | 2011-12-23 | 2014-07-02 | 辽宁省农业科学院大连生物技术研究所 | A method for extracting and purifying cordycepin from fruiting bodies of Cordyceps militaris |
| CN102432656A (en) * | 2011-12-23 | 2012-05-02 | 辽宁省农业科学院大连生物技术研究所 | A method for extracting and purifying cordycepin from fruiting bodies of Cordyceps militaris |
| CN102936271A (en) * | 2012-11-14 | 2013-02-20 | 石家庄藏诺生物股份有限公司 | Method for extracting cordycepin |
| CN102936271B (en) * | 2012-11-14 | 2015-04-22 | 石家庄藏诺生物股份有限公司 | Method for extracting cordycepin |
| CN103766545A (en) * | 2014-01-02 | 2014-05-07 | 隋新 | Preparation method of cordyceps militaris extractive-rich cordyceps militaris tea |
| CN103784481B (en) * | 2014-01-27 | 2016-06-01 | 正源堂（天津）生物科技有限公司 | A kind of method and application thereof extracting antitumor component from Cordyceps militaris (L.) Link. |
| CN103751225A (en) * | 2014-01-27 | 2014-04-30 | 正源堂（天津）生物科技有限公司 | Method for extracting antitumor active ingredients of cordyceps militaris and application thereof |
| CN103784481A (en) * | 2014-01-27 | 2014-05-14 | 正源堂（天津）生物科技有限公司 | Method for extracting anti-tumor active component from Cordyceps militaris and application of active component |
| CN103751225B (en) * | 2014-01-27 | 2016-01-20 | 图克（天津）医药科技有限公司 | The extracting method of Cordyceps militaris (L.) Link. antitumor component and application thereof |
| CN104788521A (en) * | 2015-03-24 | 2015-07-22 | 北京电子科技职业学院 | Method for rapidly separating cordycepin from fermentation broth |
| CN105037469A (en) * | 2015-06-24 | 2015-11-11 | 中山鼎晟生物科技有限公司 | A kind of extraction method of cordycepin in submerged fermentation broth of Cordyceps militaris |
| CN105646627A (en) * | 2015-12-17 | 2016-06-08 | 常熟浸大科技有限公司 | Method for extracting purified cordycepin from cordyceps militaris nutrient solution |
| CN105646627B (en) * | 2015-12-17 | 2019-05-14 | 常熟浸大科技有限公司 | A method of the extraction purification cordycepin from Cordyceps militaris culture solution |
| CN108490864A (en) * | 2018-04-12 | 2018-09-04 | 中国船舶重工集团公司第七0三研究所 | Intelligent production flexibility route control system |
| CN113233970A (en) * | 2021-05-18 | 2021-08-10 | 山东国力生物技术研究院 | Preparation method of high-purity hypocrellin |
| CN113233970B (en) * | 2021-05-18 | 2022-09-02 | 山东元核生物工程有限公司 | Preparation method of high-purity hypocrellin |
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