CN110028472B - Method for extracting isopentenyl flavonoid compound from liquorice by using ionic liquid - Google Patents
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Abstract
The invention discloses a method for extracting isopentene group flavonoid compounds in liquorice by using ionic liquid, which comprises the steps of mixing liquorice powder with pure ionic liquid, carrying out ultrasonic extraction, centrifuging after extraction is finished, and taking supernatant to obtain the isopentene group flavonoid compounds. Most preferred ionic liquids [ C 8 MIM]BF 4 The optimal extraction conditions are as follows: the solid-to-liquid ratio is 28.31mL/g; the extraction time is 32.77min; the extraction temperature is 92.60 ℃; the soaking time is 9.83h. The content of four compounds isoangustone A, glycycoumarin, glycyrhiza isoflavone and glycyrhidine in the product is 45.6, 346.9, 214.9 and 224.5 mug/g respectively by HPLC analysis. Compared with the traditional extraction method, the ionic liquid has higher specificity for extracting the prenylflavonoid in the liquorice.
Description
Technical Field
The invention belongs to the technical field of plant extraction and separation, and particularly relates to a method for extracting four main isopentenyl flavones (isoangustone A, glycycoumarin, glycyrrhizine and glycyrriine) from liquorice by using ionic liquid.
Background
Licorice is one of the most commonly used Chinese medicines and is also recorded in Japanese pharmacopoeia, european pharmacopoeia and United states pharmacopoeia in addition to Chinese pharmacopoeia. The liquorice is called as 'old age' in ancient medical books, has various efficacies of tonifying spleen and qi, clearing heat and detoxicating, eliminating phlegm and stopping cough, relieving spasm and pain, harmonizing various medicines and the like, and is mainly used for diseases such as weakness of spleen and stomach, lassitude and hypodynamia, palpitation and shortness of breath, cough and excessive phlegm, limb spasm and acute pain and the like.
The licorice has many chemical components, mainly triterpenoid saponins, flavone glycosides and isopentenyl flavonoids. Wherein the isopentenyl flavonoid compound is flavonoid aglycone connected with an isopentenyl side chain, and the compound has more parent nucleus types including flavone, isoflavone, dihydroisoflavone, isoflavane, 3-phenylcoumarin and the like. The prenylflavonoids in Glycyrrhrizae radix mainly comprise isoangustone A, glycycoumarin, dihydroisoflavone, bicifadine, and glabridin, and have antiinflammatory, antioxidant, antitumor, antibacterial, and hepatoprotective effects.
The content of isopentenyl flavonoid compound in Glycyrrhrizae radix is less than 100 μ g/g, which is far lower than the content of triterpene saponin and flavone glycoside. At present, water, ethanol and other traditional solvents are generally adopted for extracting the isopentenyl flavonoid component in the liquorice, and are not selective, and moreover, the content of the isopentenyl flavonoid in an extracting solution is very low, and the component is usually obtained by enrichment through repeated separation and purification of column chromatography, so that the operation is complicated, and time and labor are wasted.
Ionic liquids generally consist of a relatively large volume of organic cations and a relatively small volume of organic or inorganic anions and are liquid at room temperature. As a green solvent for replacing the traditional organic solvent, compared with the traditional solvent, the ionic liquid has the following advantages: no pollution, wide liquid temperature range, low volatilization, incombustibility and high stability. Most importantly, the structure of the ionic liquid has designability, and the properties of polarity, hydrophobicity, solubility and the like of the ionic liquid can be regulated and controlled through the combination of different anions and cations, so that the dissolving and extracting capacity of a target compound is regulated. Due to these special properties of ionic liquids, they have been widely used in recent years for the extraction and extraction of natural products. However, at present, no report about the application of the ionic liquid to extraction and extraction of isopentenyl flavonoid components in liquorice is found.
Disclosure of Invention
The invention aims to provide a method for extracting four main isopentenyl flavonoid compounds (isoangustone A, glycycoumarin, glycyrhiza biflavone and glycyrrizin) from liquorice by utilizing ionic liquid, and the method is green and environment-friendly, has high specificity and extraction efficiency and is simple to operate.
The purpose of the invention is realized by the following technical scheme:
a method for extracting main isopentenyl flavonoid compounds (isoangustone A, glycycoumarin, glycyrhiza isoflavone and glycyrrizine) from liquorice by using ionic liquid comprises the steps of mixing dry liquorice powder and pure ionic liquid according to a solid-to-liquid ratio of 5-40 mL/g, soaking for 0-12 h, carrying out ultrasonic extraction at the temperature of 20-100 ℃, extracting for 5-40 min, centrifuging after extraction is finished, and taking supernatant to obtain the compound.
Preferably, the solid-to-liquid ratio is 20-40 mL/g; the extraction time is 20-40 min; the extraction temperature is 80-100 ℃; the soaking time is 8-12 h.
More preferably, the solid-to-liquid ratio is 28.31mL/g; the extraction time is 32.77min; the extraction temperature is 92.60 ℃; the soaking time is 9.83h.
The ionic liquid is [ C ] 8 MIM]BF 4 ,[C 8 MIM]PF 6 ,[C 8 MIM]SbF 6 ,[C 8 MIM]N(CN) 2 ,[C 8 MIM](CF 3 SO 2 ) 2 N,[C 8 MIM]CF 3 SO 3 ,[C 2 MIM]BF 4 ,[C 4 MIM]BF 4 ,[C 6 MIM]BF 4 ,[C 10 MIM]BF 4 Or [ C 12 MIM]BF 4 。
The most preferred ionic liquid is [ C ] 8 MIM]BF 4 Because the extraction efficiency of the target compound is high.
The compound isoangustone A, glycycoumarin, glycyrrexate and glycyrrexate have the following structural formulas:
has the advantages that: the invention adopts an ionic liquid ultrasonic-assisted extraction-HPLC detection method, designs a Box-Behnken four-factor three-level central combination experiment by applying Design-Expert statistical analysis software, and simultaneously performs content determination on isoangustone A, glycycoumarin, glycyrrexaflavone and glycyrrexadine in an extracting solution (diluted by methanol with the same volume) by using an HPLC method to obtain an optimal extraction process, has high extraction rate, and can extract prenylflavonoid compounds from the glycyrrihiza with high specificity. The adopted ionic liquid can be recycled, is environment-friendly and pollution-free, and is suitable for industrial production.
1. Firstly, the best ionic liquid is determined as an extracting agent, and different anions [ C ] are respectively compared 8 MIM]BF 4 ,[C 8 MIM]PF 6 ,[C 8 MIM]SbF 6 ,[C 8 MIM]N(CN) 2 ,[C 8 MIM](CF 3 SO 2 ) 2 N,[C 8 MIM]CF 3 SO 3 And different cations [ C ] 2 MIM]BF 4 ,[C 4 MIM]BF 4 ,[C 6 MIM]BF 4 ,[C 8 MIM]BF 4 ,[C 10 MIM]BF 4 ,[C 12 MIM]BF 4 The extraction efficiency of the objective Compound was finally determined [ C ] 8 MIM]BF 4 Is the best extractant.
2. By [ C ] 8 MIM]BF 4 On the basis, the four extraction conditions are taken as factors to determine the horizontal range of the four extraction conditions in a response curve surface experiment, and finally the solid-liquid ratio is determined to be 20-40 mL/g; the extraction time is 20-40 min; the extraction temperature is 80-100 ℃; the soaking time is 8-12 h.
3. Adopting Design-Expert software to Design a response surface experiment, determining the maximum extraction rate of isoangustone A, glycycoumarin, glycyrhiza isoflavone and glycyrhidine and the corresponding factor level, and finally determining the solid-to-liquid ratio to be 28.31mL/g; the extraction time is 32.77min; the extraction temperature is 92.60 ℃; the soaking time is 9.83h.
4. And (3) extracting four main isopentenyl flavones in the liquorice by adopting the optimal factor level in the step (3), and comparing the method with the traditional solvent extraction to determine the specificity of the ionic liquid extraction.
Drawings
FIG. 1 shows the extraction efficiency of ionic liquids with different anions on four isopentenyl flavonoids in licorice.
FIG. 2 shows the extraction efficiency of ionic liquids with different cations on four prenyl flavonoids in licorice.
FIG. 3 shows the effect of solid-liquid ratio on the extraction efficiency of four prenyl flavonoids in licorice.
FIG. 4 shows the effect of extraction temperature on the extraction efficiency of four prenyl flavonoids in licorice.
FIG. 5 shows the effect of extraction time on the extraction efficiency of four prenyl flavonoids from licorice.
FIG. 6 shows the effect of soaking time on the extraction efficiency of four prenyl flavonoids from licorice.
FIG. 7 shows the effect of interaction on the total extraction efficiency of four prenyl flavonoids from licorice.
FIG. 8 is a liquid chromatogram of four prenyl flavonoids extracted from radix Glycyrrhizae with ionic liquid and conventional solvents (water and methanol). In the figure, the compounds of flavone glycoside and triterpene saponin are shown in 0-18 min; is isopentene flavonoid compound in 18-36 min.
Detailed Description
The invention will be further described with reference to specific examples, but the scope of protection of the invention is not limited thereto:
materials, reagents, instruments and the like used in the following examples are commercially available unless otherwise specified.
A method for extracting four main isopentene-based flavonoid compounds in liquorice by using ionic liquid specifically comprises the following steps:
precisely weighing 1g of Glycyrrhrizae radix powder, adding 30mL of pure ionic liquid, soaking for 12h, performing ultrasonic extraction at 50 deg.C for 30min, centrifuging, and collecting supernatant.
1. Selection of reaction conditions
And (3) sequentially changing extraction conditions such as ionic liquid type, solid-liquid ratio, extraction temperature, extraction time, soaking time and the like, and investigating the influence of the extraction conditions on the extraction efficiency. Each experiment was done in triplicate.
1. Selection of ionic liquid species
Ionic liquids [ C ] selected from different anions 8 MIM]BF 4 ,[C 8 MIM]PF 6 ,[C 8 MIM]SbF 6 ,[C 8 MIM]N(CN) 2 ,[C 8 MIM](CF 3 SO 2 ) 2 N,[C 8 MIM]CF 3 SO 3 Extracting prenylflavonoids from Glycyrrhrizae radix, diluting the extractive solution with methanol of the same volume, and comparing the extraction efficiencies of four target compounds by HPLC analysis (in each group, the maximum extraction efficiency is defined as 100%, and the relative extraction efficiencies obtained by comparing the values of other groups are the same below), to find out anion BF 4 - The extraction efficiency was highest for the four target compounds, see figure 1.
Fixing the anion as BF 4 - Respectively selecting ionic liquids [ C ] of different cations 2 MIM]BF 4 ,[C 4 MIM]BF 4 ,[C 6 MIM]BF 4 ,[C 8 MIM]BF 4 ,[C 10 MIM]BF 4 ,[C 12 MIM]BF 4 Extracting isopentenyl flavonoid compounds in liquorice according to the conditions, diluting the extracting solution with methanol with the same volume, comparing the extraction efficiency of four target compounds by HPLC analysis, and finding out cation [ C ] 8 MIM] + The extraction efficiency was highest for the four target compounds, see figure 2. Thus, the present invention selects [ C 8 MIM]BF 4 As an extractant.
2. Selection of solid-to-liquid ratio
According to the extraction conditions, the effects of different solid-liquid ratios of 5, 10, 20, 30 and 40mL/g on the extraction efficiency of the target compound are respectively examined in the same other experiments. As shown in fig. 3, when the solid-liquid ratio reached 30mL/g, the extraction efficiency reached the maximum value, and the solid-liquid ratio continued to increase, and the extraction efficiency decreased conversely. This may be due to the ionic liquid itself and the physical properties.
3. Selection of extraction temperature
According to the extraction conditions, the influence of different extraction temperatures of 20 ℃,40 ℃,60 ℃,80 ℃,90 ℃ and 100 ℃ on the extraction efficiency of the target compound is respectively examined in the same other experiments. As shown in fig. 4, when the extraction temperature was increased from 20 ℃ to 80 ℃, the extraction efficiency of the target compound was gradually increased, and when the temperature was further increased, the extraction efficiency of glycyrrhetinic was rather decreased, probably due to the degradation of the compound at high temperature. The extraction efficiency of the other three target compounds did not change significantly upon further increase in temperature.
4. Selection of extraction time
According to the extraction conditions, the influence of different extraction times of 5, 10, 20, 30 and 40min on the extraction efficiency of the target compound is respectively examined in the same experiment. As shown in fig. 5, when the extraction temperature was increased from 5min to 20min, the extraction efficiency of the target compound was gradually increased, and after further extension of the extraction time, the extraction efficiency of glycyrrhiza bifida could be further increased, while the extraction efficiency of the other three target compounds was not significantly changed after further extension of the extraction time, indicating that the extraction process had reached equilibrium.
5. Selection of soaking time
According to the extraction conditions, the influence of different soaking times of 0,2,4,8 and 12h on the extraction efficiency of the target compound is respectively examined in the same other experiments. As shown in fig. 6, when the soaking time was 8h, the extraction efficiency of each of the four target compounds was at the maximum, and continuing to increase the soaking time had no significant effect on the extraction efficiency.
2. Optimization of optimal extraction conditions by response surface experiments
According to the design principle of a center combined experiment of Box-Behnken, the total extraction efficiency of four target compounds in liquorice is taken as a response value (Y), four factors of soaking time (A), extraction time (B), solid-liquid ratio (C) and extraction temperature (D) are selected, and a four-factor three-level response surface analysis method is adopted. The experimental factors and level design are shown in table 1.
TABLE 1 horizontal design table for response surface factor
To investigate each factor and itsThe influence of interaction on extraction efficiency is realized by performing multiple regression fitting on four-factor three levels in table 1 by using Design-Expert software to obtain a calculation equation Y =97.79-1.61A +3.21B-1.02C +5.15D-0.40AB +1.54AC-1.72AD +0.65BC +0.025BD-3.87CD-14.66A of total extraction efficiency 2 -5.65B 2 -5.83C 2 -11.46D 2 . The analysis of variance for fitting the quadratic polynomial model is shown in Table 2, model P<0.0001 (very significant), indicating that the model can be used to make predictions of response values. The model mismatching item is not significant, and the fitting degree of the regression equation in the whole regression space is better.
TABLE 2 significance test of regression equation
Note: * Polar significance (P < 0.001); * Height significance (P < 0.01); * Significant (P < 0.05)
The response surface graph obtained from the regression equation is shown in fig. 7, which shows the relationship between the action and interaction of each factor and the extraction efficiency. The optimal extraction conditions of four main isopentenyl flavonoid compounds in the liquorice are obtained by analysis: the solid-to-liquid ratio is 28.31mL/g; the extraction time is 32.77min; the extraction temperature is 92.60 ℃; the soaking time is 9.83h. The content of isoangustone A, glycycoumarin, glycyrhizid and glycyrhizid in the liquorice measured according to the conditions is respectively 45.6, 346.9, 214.9 and 224.5 mu g/g, which is similar to the calculated value of the model, and the optimal extraction condition obtained by adopting the response surface method is accurate and reliable and has practical application value.
Verification example 1
A method for extracting four main isopentene-based flavonoids from Glycyrrhrizae radix with ionic liquid comprises precisely weighing Glycyrrhrizae radix powder 1g, adding 28.31mL pure ionic liquid [ C ] 8 MIM]BF 4 Soaking for 9.83h, ultrasonic extracting at 92.60 deg.C for 32.77min, centrifuging, and collecting supernatant.
After the supernatant was diluted with an equal volume of methanol, HPLC analysis showed that the extract contained mainly prenyl flavonoids (18-36 min), and the contents of isoangustone A, glycycoumarin, glycyrhizoisoflavone and glycyrrizin were 45.6, 346.9, 214.9 and 224.5. Mu.g/g, respectively. While the content of the flavone glycoside and the triterpenoid saponin compounds is extremely low (0-18 min).
Comparative example 1 (methanol extraction in FIG. 8)
Precisely weighing 1g of Glycyrrhrizae radix powder, adding 30mL of methanol, soaking for 12h, performing ultrasonic extraction at 50 deg.C for 30min, centrifuging, and collecting supernatant.
After the supernatant is diluted by methanol with the same volume, HPLC analysis shows that (figure 8), the extract mainly contains flavone glycoside and triterpenoid saponin compounds (0-18 min), and simultaneously contains a small amount of isopentenyl flavonoid compounds (18-36 min).
Comparative example 2 (Water extraction in FIG. 8)
Precisely weighing 1g of Glycyrrhrizae radix powder, adding 30mL of water, soaking for 12h, performing ultrasonic extraction at 50 deg.C for 30min, centrifuging, and collecting supernatant.
After the supernatant is diluted by methanol with the same volume, HPLC analysis shows that (figure 8), the extract mainly contains flavone glycoside and triterpenoid saponin compounds (0-18 min), and almost no isopentenyl flavonoid compounds (18-36 min).
And (4) conclusion: the invention adopts pure ionic liquid to ultrasonically extract the isopentenyl flavonoid compound in the liquorice for the first time, and compared with the traditional extraction method, the method has higher specificity and extremely low content of other types of components in the extracting solution. Meanwhile, the method is simple to operate, green and environment-friendly, provides a new idea for quickly obtaining the isopentenyl flavonoid compound in the liquorice, and is suitable for industrial expanded production.
Claims (2)
1. The method for extracting the isopentenyl flavonoid compound from the liquorice by using the ionic liquid is characterized in that the isopentenyl flavonoid compound is as follows:
mixing licorice powder and pure ionic liquid, carrying out ultrasonic extraction, centrifuging after extraction is finished, and taking supernatant to obtain the liquorice extract;
wherein the ionic liquid is BF 4 − The cation is [ C ] 8 MIM] + ；
The solid-liquid ratio of the licorice powder to the ionic liquid is 5-40 mL/g, the extraction time is 5-40 min, the extraction temperature is 20-100 ℃, and the soaking time is 0-12 h and is more than 0.
2. The method for extracting isopentenyl flavonoid compounds from licorice by using ionic liquid as claimed in claim 1, wherein the solid-to-liquid ratio of licorice powder to ionic liquid is 28.31mL/g, the extraction time is 32.77min, the extraction temperature is 92.60 ℃, and the soaking time is 9.83h.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN101982466A (en) * | 2010-10-29 | 2011-03-02 | 河南科技大学 | Method for extracting isoflavonoids compound in all-grass of Twining Rhynchosia with ionic liquid |
| CN103923094A (en) * | 2014-04-14 | 2014-07-16 | 石河子大学 | Method for separating active component-glabridin contained in natural product glycyrrhiza glabra |
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| CN101982466A (en) * | 2010-10-29 | 2011-03-02 | 河南科技大学 | Method for extracting isoflavonoids compound in all-grass of Twining Rhynchosia with ionic liquid |
| CN103923094A (en) * | 2014-04-14 | 2014-07-16 | 石河子大学 | Method for separating active component-glabridin contained in natural product glycyrrhiza glabra |
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| Title |
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| 咪唑类离子液体在天然产物黄酮类成分提取中的应用;田刚 等;《中草药》;20190430;第50卷(第7期);全文 * |
| 甘草有效成分的离子液体提取方法和工艺研究;高宇;《中国优秀硕士学位论文全文数据库》;20160415(第4期);全文 * |
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