CN104887723A - Method for extracting flavonoids from ginkgo biloba leaves with deep eutectic solvent - Google Patents
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- 229930003935 flavonoid Natural products 0.000 title claims abstract description 37
- 235000017173 flavonoids Nutrition 0.000 title claims abstract description 37
- 239000002904 solvent Substances 0.000 title claims abstract description 36
- 235000008100 Ginkgo biloba Nutrition 0.000 title claims abstract description 34
- 150000002215 flavonoids Chemical class 0.000 title claims abstract description 33
- 230000005496 eutectics Effects 0.000 title claims abstract description 29
- 244000194101 Ginkgo biloba Species 0.000 title claims abstract description 25
- 238000000034 method Methods 0.000 title claims abstract description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 17
- 229960001231 choline Drugs 0.000 claims abstract description 15
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 claims abstract description 15
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000007788 liquid Substances 0.000 claims abstract description 12
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims abstract description 9
- -1 ethylene glycol-oxalic acid-choline chloride Chemical compound 0.000 claims abstract description 8
- 150000003839 salts Chemical class 0.000 claims abstract description 8
- 239000001763 2-hydroxyethyl(trimethyl)azanium Substances 0.000 claims abstract description 4
- 235000019743 Choline chloride Nutrition 0.000 claims abstract description 4
- SGMZJAMFUVOLNK-UHFFFAOYSA-M choline chloride Chemical compound [Cl-].C[N+](C)(C)CCO SGMZJAMFUVOLNK-UHFFFAOYSA-M 0.000 claims abstract description 4
- 229960003178 choline chloride Drugs 0.000 claims abstract description 4
- 235000006408 oxalic acid Nutrition 0.000 claims abstract description 4
- 239000003085 diluting agent Substances 0.000 claims abstract description 3
- 239000002994 raw material Substances 0.000 claims abstract description 3
- 239000000284 extract Substances 0.000 claims description 23
- 235000011201 Ginkgo Nutrition 0.000 claims description 9
- 241000218628 Ginkgo Species 0.000 claims description 9
- 238000005119 centrifugation Methods 0.000 claims description 6
- 239000012535 impurity Substances 0.000 claims description 6
- 239000012528 membrane Substances 0.000 claims description 6
- 239000011259 mixed solution Substances 0.000 claims description 5
- 239000000287 crude extract Substances 0.000 claims description 4
- 235000008979 vitamin B4 Nutrition 0.000 claims description 4
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Substances ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 claims description 3
- 238000002604 ultrasonography Methods 0.000 claims description 3
- 238000001914 filtration Methods 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- 239000007787 solid Substances 0.000 claims description 2
- 238000005728 strengthening Methods 0.000 claims description 2
- 238000000605 extraction Methods 0.000 abstract description 14
- 238000005265 energy consumption Methods 0.000 abstract description 2
- 238000011031 large-scale manufacturing process Methods 0.000 abstract description 2
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- 230000003247 decreasing effect Effects 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 238000001514 detection method Methods 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000013076 target substance Substances 0.000 description 4
- 238000002137 ultrasound extraction Methods 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000009429 Ginkgo biloba extract Substances 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229940068052 ginkgo biloba extract Drugs 0.000 description 3
- 235000020686 ginkgo biloba extract Nutrition 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 2
- 239000002360 explosive Substances 0.000 description 2
- 238000000638 solvent extraction Methods 0.000 description 2
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- 238000010364 biochemical engineering Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
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- 230000017531 blood circulation Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
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- 230000007721 medicinal effect Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000003809 water extraction Methods 0.000 description 1
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Abstract
Description
技术领域technical field
本发明涉及生化工程技术，特别是一种利用低共熔溶剂提取银杏叶中黄酮类化合物的方法。The invention relates to biochemical engineering technology, in particular to a method for extracting flavonoids in ginkgo leaves by using a deep eutectic solvent.
技术背景technical background
银杏叶为银杏科植物银杏(Ginkgo biloba L.)的干燥叶，秋季叶尚绿时采收。银杏叶的功能为活血化瘀，通络止痛。现在临床上主要用于心血管疾病。从银杏叶中提取药物成分始于20世纪，德国Schwabe制药公司研发的产品EGB761及其标准的制备方法则进一步推动了对银杏叶的研究进程。目前已从银杏叶中分离得到多种化学成分，而黄酮类化合物是银杏叶中含量较高的成分，目前认为是银杏叶提取物中的有效成分之一。因此提高银杏叶提取物中黄酮类成分是决定银杏叶提取物药用效果的关键。Ginkgo biloba is the dry leaf of Ginkgo biloba L., which is harvested in autumn when the leaves are still green. The function of Ginkgo biloba is to promote blood circulation and remove blood stasis, dredge collaterals and relieve pain. Now it is mainly used clinically for cardiovascular diseases. The extraction of medicinal ingredients from Ginkgo biloba began in the 20th century. The product EGB761 and its standard preparation method developed by Schwabe Pharmaceutical Company in Germany further promoted the research process on Ginkgo biloba. At present, a variety of chemical components have been isolated from Ginkgo biloba, and flavonoids are components with a relatively high content in Ginkgo biloba, and are currently considered to be one of the effective components in Ginkgo biloba extract. Therefore, improving the flavonoids in Ginkgo biloba extract is the key to determine the medicinal effect of Ginkgo biloba extract.
目前从银杏叶中提取黄酮类化合物的方法从提取溶剂上分为挥发性有机溶剂和超亚临界CO2提取；从强化方法上分为超声强化和微波强化。有机溶剂提取法是近年来国内外用于提取银杏叶中黄酮应用最为普遍的方法。一般可用甲醇、乙醇、乙酸乙酯、丙酮或者一些极性较大的混合溶液。如尹丽等人以乙醇浓度为75％的乙醇-水提取溶剂作为银杏叶中黄酮提取的最佳溶剂比例，参见：中国实验方剂学杂志，2013，19(18)：260-262。有机溶剂提取虽然操作简便、易于工业化，但溶剂易燃、易爆、挥发性强，存在安全隐患，同时严重污染环境。超亚临界CO2提取，参见：张玉祥，中国中医药科技，2006,13(4)：255-256。虽然溶剂绿色安全，但是要求设备耐高压，一次性投入高。超声强化，参见：杨荣华，中国医药导报，2010，7(20)：25-27，和微波强化，参见：陈金娥，光谱实验室，2011,28(2)：623-626，提取黄酮，均采用挥发性有机溶剂，虽然提取时间缩短，溶剂消耗减少，收率提高，但仍存在有机试剂提取普遍的安全与污染问题。At present, the methods of extracting flavonoids from Ginkgo biloba are divided into volatile organic solvent and super subcritical CO 2 extraction from the extraction solvent; from the enhancement method, they are divided into ultrasonic enhancement and microwave enhancement. Organic solvent extraction is the most common method used to extract flavonoids from ginkgo leaves at home and abroad in recent years. Generally, methanol, ethanol, ethyl acetate, acetone or some polar mixed solutions can be used. For example, Yin Li et al. used an ethanol-water extraction solvent with an ethanol concentration of 75% as the optimum solvent ratio for flavonoid extraction from Ginkgo biloba leaves. See: Chinese Journal of Experimental Formulas, 2013, 19(18): 260-262. Although organic solvent extraction is easy to operate and easy to industrialize, the solvent is flammable, explosive, and highly volatile, which poses safety hazards and seriously pollutes the environment. Supersubcritical CO 2 extraction, see: Zhang Yuxiang, China Traditional Chinese Medicine Science and Technology, 2006,13(4):255-256. Although the solvent is green and safe, the equipment is required to withstand high pressure and the one-time investment is high. Ultrasound enhancement, see: Yang Ronghua, China Medical Herald, 2010, 7(20): 25-27, and microwave enhancement, see: Chen Jin'e, Spectrum Laboratory, 2011, 28(2): 623-626, flavonoids were extracted, all using Volatile organic solvents, although the extraction time is shortened, the solvent consumption is reduced, and the yield is increased, but there are still common safety and pollution problems in the extraction of organic reagents.
发明内容Contents of the invention
本发明的目的是针对上述存在问题，提供一种利用低共熔溶剂提取银杏叶中黄酮类化合物的方法，采用本发明提取黄酮类化合物可有效解决现有黄酮提取技术使用易燃、易爆有机溶剂存在的问题。The purpose of the present invention is to address the above-mentioned problems and provide a method for extracting flavonoids from ginkgo leaves using a deep eutectic solvent. Using the present invention to extract flavonoids can effectively solve the problem of using flammable and explosive organic compounds in the existing flavonoid extraction technology. Problems with solvents.
本发明的技术方案：Technical scheme of the present invention:
一种利用低共熔溶剂提取银杏叶中黄酮类化合物的方法，以银杏叶为原料，以胆碱类低共熔溶剂为提取剂，以水为降低体系粘度的稀释剂，在超声的强化下提取黄酮类化合物，包括以下步骤：A method for extracting flavonoids in ginkgo leaves using a deep eutectic solvent, using ginkgo leaves as a raw material, using a choline-based deep eutectic solvent as an extractant, and using water as a diluent to reduce the viscosity of the system, under the strengthening of ultrasound Extracting flavonoids, comprising the following steps:
1)将干燥银杏叶粉碎，过10-80目筛，加入胆碱类低共熔溶剂和水的混合液，胆碱类低共熔溶剂和水的混合液中胆碱类低共熔溶剂和水的体积比为1:10，干燥银杏叶与胆碱类低共熔溶剂和水的混合液的用量比为1g:5-50mL，在超声功率为1-100W/cm2、超声频率为20-80kHz、温度为40-60℃条件下，提取20-40分钟，然后采用离心或过滤进行液-固分离，得到黄酮类化合物的粗制提取液；1) Ginkgo biloba is dried, crossed 10-80 mesh sieve, added the mixed solution of choline deep eutectic solvent and water, the choline deep eutectic solvent and water in the mixed solution of choline deep eutectic solvent and water The volume ratio of water is 1:10, the dosage ratio of the mixture of dried ginkgo biloba and choline deep eutectic solvent and water is 1g:5-50mL, when the ultrasonic power is 1-100W/cm 2 and the ultrasonic frequency is 20 Under the conditions of -80kHz and temperature of 40-60°C, extract for 20-40 minutes, and then perform liquid-solid separation by centrifugation or filtration to obtain a crude extract of flavonoids;
2)将上述黄酮类化合物粗制提取液经0.45μm过滤膜过滤，去除杂质，得到黄酮类化合物的精制提取液。2) Filtrating the crude extract of the flavonoids through a 0.45 μm filter membrane to remove impurities to obtain a refined extract of the flavonoids.
所述胆碱类低共熔溶剂为乙二醇-草酸-氯化胆碱的室温熔盐液体，室温熔盐液体中乙二醇、草酸和氯化胆碱的摩尔比1:1:1。The cholines deep eutectic solvent is a room temperature molten salt liquid of ethylene glycol-oxalic acid-choline chloride, and the molar ratio of ethylene glycol, oxalic acid and choline chloride in the room temperature molten salt liquid is 1:1:1.
本发明的优点是：The advantages of the present invention are:
该提取方法具有提取剂不燃爆、不挥发、损耗小、耗能低、无安全隐患、操作简便、易于工业化、效率高等特点，可用于黄酮类化合物高效绿色规模化生产和实现银杏叶资源的综合利用。The extraction method has the characteristics of non-flammable and non-volatile extractant, low loss, low energy consumption, no safety hazard, simple operation, easy industrialization, high efficiency, etc., and can be used for high-efficiency green large-scale production of flavonoids and realization of Ginkgo biloba resource synthesis use.
具体实施方式Detailed ways
以下实施例中，所述胆碱类低共熔溶剂为乙二醇-草酸-氯化胆碱的室温熔盐液体，室温熔盐液体中乙二醇、草酸和氯化胆碱的摩尔比1:1:1。In the following examples, the cholines deep eutectic solvent is the room temperature molten salt liquid of ethylene glycol-oxalic acid-choline chloride, and the mol ratio of ethylene glycol, oxalic acid and choline chloride in the room temperature molten salt liquid is 1 :1:1.
实施例1：Example 1:
一种利用低共熔溶剂提取银杏叶中黄酮类化合物的方法，包括以下步骤：A method utilizing deep eutectic solvent to extract flavonoids in Ginkgo biloba, comprising the following steps:
1)干燥银杏叶粉碎，过10目筛，取10克银杏叶粉末加25毫升胆碱类低共熔溶剂和25毫升水，40℃超声提取20分钟，功率100W/cm2，频率20kHz，提取液4000rpm离心分离5分钟后得到黄酮提取液；1) Dried ginkgo leaves are crushed and passed through a 10-mesh sieve. Take 10 grams of ginkgo leaf powder, add 25 ml of choline-based deep eutectic solvent and 25 ml of water, and perform ultrasonic extraction at 40°C for 20 minutes, with a power of 100W/cm 2 and a frequency of 20kHz. 4000rpm centrifugation for 5 minutes to obtain the flavonoid extract;
2)将步骤1)得到提取液黄酮类化合物提取液经过0.45μm过滤膜过滤，去除杂质，得到过滤后的提取液。2) Filter the flavonoid compound extract obtained in step 1) through a 0.45 μm filter membrane to remove impurities, and obtain the filtered extract.
将得到的提取液用高效液相色谱仪进样10μL检测，经计算得到目标物的提取量为160毫克/10克。10 μL of the obtained extract was injected into a high-performance liquid chromatograph for detection, and the extraction amount of the target substance was calculated to be 160 mg/10 g.
实施例2：Example 2:
一种利用低共熔溶剂提取银杏叶中黄酮类化合物的方法，包括以下步骤：A method utilizing deep eutectic solvent to extract flavonoids in Ginkgo biloba, comprising the following steps:
1)取粉碎并过20目筛的银杏叶粉末10克，加50毫升胆碱类低共熔溶剂和500毫升水，50℃超声提取40分钟，功率10W/cm2，频率20kHz，提取液4000rpm离心分离5分钟后得到黄酮提取液；1) Take 10 grams of ginkgo leaf powder that has been crushed and passed through a 20-mesh sieve, add 50 milliliters of choline-based deep eutectic solvent and 500 milliliters of water, conduct ultrasonic extraction at 50°C for 40 minutes, power 10W/cm 2 , frequency 20kHz, extract 4000rpm After centrifugation for 5 minutes, the flavonoid extract was obtained;
2)将步骤1)得到提取液黄酮类化合物提取液经过0.45μm过滤膜过滤，去除杂质，得到过滤后的提取液。2) Filter the flavonoid compound extract obtained in step 1) through a 0.45 μm filter membrane to remove impurities, and obtain the filtered extract.
将得到的提取液用高效液相色谱仪进样10μL检测，经计算得到目标物的提取量为200毫克/10克。10 μL of the obtained extract was injected into a high-performance liquid chromatograph for detection, and the extraction amount of the target substance was calculated to be 200 mg/10 g.
实施例3：Example 3:
一种利用低共熔溶剂提取银杏叶中黄酮类化合物的方法，包括以下步骤：A method utilizing deep eutectic solvent to extract flavonoids in Ginkgo biloba, comprising the following steps:
1)取粉碎并过80目筛的银杏叶粉末10克，加100毫升胆碱类低共熔溶剂和400毫升水，60℃超声提取40分钟，功率10W/cm2，频率80kHz，提取液4000rpm离心分离5分钟后得到黄酮提取液；1) Take 10 grams of Ginkgo biloba powder that has been crushed and passed through an 80-mesh sieve, add 100 milliliters of choline-based deep eutectic solvent and 400 milliliters of water, conduct ultrasonic extraction at 60°C for 40 minutes, power 10W/cm 2 , frequency 80kHz, extract 4000rpm After centrifugation for 5 minutes, the flavonoid extract was obtained;
2)将步骤1)得到提取液黄酮类化合物提取液经过0.45μm过滤膜过滤，去除杂质，得到过滤后的提取液。2) Filter the flavonoid compound extract obtained in step 1) through a 0.45 μm filter membrane to remove impurities, and obtain the filtered extract.
将得到的提取液用高效液相色谱仪进样10μL检测，经计算得到目标物的提取量为280毫克/10克。10 μL of the obtained extract was injected into a high-performance liquid chromatograph for detection, and the extraction amount of the target substance was calculated to be 280 mg/10 g.
实施例4：Example 4:
一种利用低共熔溶剂提取银杏叶中黄酮类化合物的方法，包括以下步骤：A method utilizing deep eutectic solvent to extract flavonoids in Ginkgo biloba, comprising the following steps:
1)取粉碎并过60目筛的银杏叶粉末10克，加100毫升胆碱类低共熔溶剂和200毫升水，60℃超声提取40分钟，功率50W/cm2，频率20kHz，提取液4000rpm离心分离10分钟后得到黄酮提取液。1) Take 10 grams of Ginkgo biloba powder that has been crushed and passed through a 60-mesh sieve, add 100 milliliters of choline-based deep eutectic solvent and 200 milliliters of water, conduct ultrasonic extraction at 60°C for 40 minutes, power 50W/cm 2 , frequency 20kHz, extract 4000rpm After centrifugation for 10 minutes, the flavonoid extract was obtained.
2)将步骤1)得到提取液黄酮类化合物提取液经过0.45μm过滤膜过滤，去除杂质，得到过滤后的提取液；2) Filter the flavonoid compound extract obtained in step 1) through a 0.45 μm filter membrane to remove impurities and obtain the filtered extract;
将得到的提取液用高效液相色谱仪进样10μL检测，经计算得到目标物的提取量为300毫克/10克。10 μL of the obtained extract was injected into a high-performance liquid chromatograph for detection, and the extraction amount of the target substance was calculated to be 300 mg/10 g.
以上所述，仅为本发明部分具体实施方式，但本发明的保护范围并不局限于此，任何熟悉本技术领域的人员在本发明揭露的技术范围内，可轻易想到的变化或替换，都应涵盖在本发明的保护范围之内。The above are only some specific implementations of the present invention, but the protection scope of the present invention is not limited thereto. Any changes or substitutions that can be easily conceived by anyone familiar with the technical field within the technical scope disclosed in the present invention are all Should be covered within the protection scope of the present invention.
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