CN107628959B - Choline eutectic solvent, preparation method and application in extraction of globeflower flavone C-glycoside - Google Patents
Choline eutectic solvent, preparation method and application in extraction of globeflower flavone C-glycoside Download PDFInfo
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- CN107628959B CN107628959B CN201711061313.8A CN201711061313A CN107628959B CN 107628959 B CN107628959 B CN 107628959B CN 201711061313 A CN201711061313 A CN 201711061313A CN 107628959 B CN107628959 B CN 107628959B
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Abstract
The invention discloses a choline eutectic solvent, a preparation method and application in extraction of globeflower flavone C-glycoside. The invention provides a choline eutectic solvent with the expression of [ N (CH)3)3CH2CH2OH]+[X·zY]－From choline bromide or choline chloride and ZnCl2Or SnCl2Or AlCl3Mixing them according to a certain mole ratio, when X is Br, Y is ZnCl2Or SnCl2(ii) a When X is Cl, Y is AlCl3. The choline eutectic solvent provided by the invention can efficiently and selectively extract three important flavone C-glycosides in globeflower: compared with the traditional methanol solvent extraction, the extraction rate of the orientin, the orientin-2 '-O-beta-L-galactoside and the vitexin can be improved, the impurities in the extract are less, and when the orientin, the orientin-2' -O-beta-L-galactoside or the vitexin monomer is prepared by taking the extract as a raw material, silica gel column separation is not required to be repeatedly used, so that the separation and purification steps can be greatly reduced, and the separation and purification cost can be reduced.
Description
Technical Field
The invention belongs to the field of chemical medicine, relates to preparation and application of a deep eutectic solvent, and particularly relates to a choline deep eutectic solvent, a preparation method and application in extraction of trollius chinensis flavone C-glycoside.
Background
In 2003, Abbott et al first discovered a good physicochemical solvent-eutectic solvent (Novel solvent properties of chlorine chloride/urea mixtures, chem. Commun.,2003:70-71) formed from a quaternary ammonium salt and an amide compound. The solvent is non-toxic and biodegradable, and the atom utilization rate in the synthesis process reaches 100%, so that the solvent is a novel green solvent. The eutectic solvent is typically a eutectic mixture of a stoichiometric ratio of a quaternary ammonium salt in combination with a hydrogen bond donor (e.g., an amide, a carboxylic acid, a polyol, etc.).
The flos Trollii is dried flower of Trohlamus chinensis Bge. The trollius chinensis is mainly distributed in northriver, Shanxi, eastern part of inner Mongolia, Liaoning and western part of Jilin, and grows in Shunling forest or mountain grass slope with elevation of 1000-plus 2200 m. Flos Trollii has effects of clearing away heat and toxic materials, and can be used for treating upper respiratory infection, pharyngitis, tonsillitis, etc. Pharmacological research shows that the flavone C-glycosides compounds such as orientin are the main active ingredients.
At present, the extraction of flavone C-glycoside components in the trollius chinensis is mainly dependent on traditional organic solvents, such as methanol, ethanol, ethyl acetate and the like. Not to be neglected, the consumption of large amounts of toxic solvents can cause irreversible damage to the environment. Therefore, the search for alternative green extraction solvents is urgent.
Disclosure of Invention
The invention aims to overcome the defects of the prior art, and provides a choline eutectic solvent, a preparation method and application in extracting globeflower flavone C-glycosides, so as to efficiently and selectively extract three important flavone C-glycosides in globeflower: orientin, orientin-2' -O-beta-L-galactoside and vitexin.
The above object of the present invention is achieved by the following technical solutions:
an expression is [ N (CH)3)3CH2CH2OH]+[X·zY]－The choline eutectic solvent of (1), wherein: x is halogen and Y isA complexing agent, z being the number of complexing agents; when X is Br, Y is ZnCl2Or SnCl2(ii) a When X is Cl, Y is AlCl3。
Preferably, z is 1.
A preparation method of the choline eutectic solvent comprises the following steps: mixing choline bromide or choline chloride with ZnCl2Or SnCl2Or AlCl3Mixing according to the molar ratio of 1: z, heating and stirring until a uniform transparent liquid is formed.
Preferably, the temperature of the heating and stirring is 70 to 90 ℃.
Preferably, the homogeneous transparent liquid is formed and then sealed and stored dry.
The choline eutectic solvent is applied to the selective extraction of the flavonoid carbon glycosides in the trollius chinensis, wherein the flavonoid carbon glycosides are orientin, orientin-2' -O-beta-L-galactoside and vitexin.
Preferably, the extracting step comprises: drying flos Trollii, pulverizing, collecting flos Trollii powder, adding appropriate amount of mixed solution of choline eutectic solvent and water, extracting, centrifuging or filtering, collecting supernatant or filtrate, diluting with organic solvent to precipitate eutectic solvent, centrifuging or filtering to remove, and concentrating supernatant or filtrate to obtain flos Trollii extract rich in orientin, orientin-2 "-O-beta-L-galactoside and vitexin.
Preferably, the volume ratio of the choline eutectic solvent to water is 2-4: 1.
Preferably, the extraction method is ultrasonic extraction.
Preferably, the organic solvent is ethanol.
The invention has the advantages that:
the invention provides a choline eutectic solvent with the expression of [ N (CH)3)3CH2CH2OH]+[X·zY]－From choline bromide or choline chloride and ZnCl2Or SnCl2Or AlCl3Mixing them according to a certain mole ratio, when X is Br, Y is ZnCl2Or SnCl2(ii) a When X is Cl, Y is AlCl3. The choline eutectic solvent provided by the inventionThree important flavone carbon glycosides in the trollius chinensis can be efficiently and selectively extracted: compared with the traditional methanol solvent extraction, the extraction rate of the orientin, the orientin-2 '-O-beta-L-galactoside and the vitexin can be improved, the impurities in the extract are less, and when the orientin, the orientin-2' -O-beta-L-galactoside or the vitexin monomer is prepared by taking the extract as a raw material, silica gel column separation is not required to be repeatedly used, so that the separation and purification steps can be greatly reduced, and the separation and purification cost can be reduced.
Drawings
FIG. 1 is an HPLC detection chromatogram of a control solution (A) and a methanol-extracted test solution (B);
fig. 2 is an HPLC detection chromatogram of the sample solution extracted from the eutectic solvent, wherein: c to H correspond to the number of the 1-6 choline eutectic solvents in sequence.
Detailed Description
The following detailed description of the present invention is provided in connection with the accompanying drawings and examples, but not intended to limit the scope of the invention.
Example 1: preparation of choline eutectic solvent
The different types of choline eutectic solvents and the preparation method are as follows:
example 2: application of choline eutectic solvent in extraction of flavone C-glycosides in globeflower
First, experiment method
1. Extraction of globeflower flavone C-glycoside
Drying flos Trollii, pulverizing, and sieving with 50 mesh sieve. Precisely weighing 2g of trollius chinensis powder, adding 40ml of a serial number 1-6 eutectic solution-water mixed solution (3:1, v/v) prepared in example 1, carrying out ultrasonic treatment (power 250W and frequency 40kHz) for 20min, cooling at room temperature, centrifuging at 13000rpm for 10min, taking supernatant, diluting the supernatant by 10 times with water, placing the diluted supernatant in a sample injection vial to serve as a test solution, and carrying out HPLC detection. Diluting the rest supernatant with 5 times volume of ethanol to precipitate eutectic solvent, filtering with 0.45 μm organic filter membrane, and concentrating the filtrate to obtain flos Trollii extract which can be used as raw material for preparing orientin, orientin-2 "-O-beta-L-galactoside and vitexin monomer.
Meanwhile, a methanol control group is arranged, the extraction solvent is methanol, and the other extraction parameters are the same as above.
2. HPLC detection conditions and parameters
The liquid phase analysis employed an Agilent 1290 liquid phase system, containing an online vacuum degasser, binary pump, autosampler, column oven and DAD detector (Agilent Technologies, Santa Clara, Calif., USA). The chromatographic separation was carried out using a ThermoBDS Hypersil C18 column (250 mm. times.4.6 mm,4.6 μm). Mobile phase: 0.1% aqueous formic acid (A) -acetonitrile (B); gradient elution procedure: 0-4min, 13-15% of B; 4-14min, 15% B; 14-18min, 15-20% of B; 18-22min, 20-35% B; the post column run time was 10min back to the initial gradient; flow rate: 0.8 mL/min; column temperature: 25 ℃; detection wavelength: 340 nm; sample introduction amount: 10 μ L. The concentrations of orientin, orientin-2' -O-beta-L-galactoside and vitexin in each sample solution are calculated by using an external standard method, and the contents of the individual carbon glucosides in one gram of the trollius chinensis medicinal material are converted to serve as the extraction rate of the carbon glucosides.
Second, experimental results
1. Influence of choline eutectic solvent on extraction rate of three flavonoid carbon glycosides in globeflower
The extraction rate of the choline eutectic solvent and the conventional methanol on orientin, orientin-2' -O-beta-L-galactoside and vitexin in the trollius chinensis is shown in the following table:
the results show that compared with the conventional methanol in the prior art, the serial number 1-6 choline eutectic solvent can obviously improve the extraction rate of the three flavone carbon glycosides of orientin, orientin-2' -O-beta-L-galactoside and vitexin in the trollius chinensis.
2. Selectivity of choline eutectic solvent for extracting three flavone carbon glycosides from trollius chinensis bunge
FIG. 1 is an HPLC detection chromatogram of a control solution (A) and a methanol-extracted test solution (B); fig. 2 is an HPLC detection chromatogram of the sample solution extracted from the eutectic solvent, wherein: c to H correspond to the number 1-6 choline eutectic solvents in sequence.
Fig. 1 and 2 show that the choline eutectic solvents with the serial numbers of 1, 2 and 6 have high selectivity on orientin, orientin-2 "-O-beta-L-galactoside and vitexin in trollius chinensis, and the orientin, orientin-2" -O-beta-L-galactoside and vitexin are mainly used in the extracting solution, so that the impurity is less, and the eutectic solvents are obviously superior to methanol and the choline eutectic solvents with the serial numbers of 3, 4 and 5.
In conclusion, the invention provides a choline eutectic solvent with the expression of [ N (CH)3)3CH2CH2OH]+[X·zY]－From choline bromide or choline chloride and ZnCl2Or SnCl2Or AlCl3Mixing them according to a certain mole ratio, when X is Br, Y is ZnCl2Or SnCl2(ii) a When X is Cl, Y is AlCl3. The choline eutectic solvent provided by the invention can efficiently and selectively extract three important flavone C-glycosides in globeflower: compared with the traditional methanol solvent extraction, the extraction rate of the orientin, the orientin-2 '-O-beta-L-galactoside and the vitexin can be improved, the impurities in the extract are less, and when the orientin, the orientin-2' -O-beta-L-galactoside or the vitexin monomer is prepared by taking the extract as a raw material, silica gel column separation is not required to be repeatedly used, so that the separation and purification steps can be greatly reduced, and the separation and purification cost can be reduced.
The above-described embodiments are intended to be illustrative of the nature of the invention, but those skilled in the art will recognize that the scope of the invention is not limited to the specific embodiments.
Claims (5)
1. The expression is [ N (CH)3)3CH2CH2OH]+[X·zY]－The application of choline eutectic solvent in selectively extracting flavone C-glycoside in globeflower, wherein the solvent is a mixture of choline eutectic solvent and flavone C-glycosideThe flavone C-glycoside is orientin, orientin-2' -O-beta-L-galactoside and vitexin;
wherein:
x ═ Br, Y is ZnCl2Or SnCl2；
Or X ═ Cl and Y are AlCl3；
z is the number of complexing agents, and z is 1.
2. The expression of claim 1 is [ N (CH)3)3CH2CH2OH]+[X·zY]－The application of the choline eutectic solvent in selectively extracting the flavone C-glycosides in the globeflower is characterized in that the extraction steps comprise: drying flos Trollii, pulverizing, collecting flos Trollii powder, adding appropriate amount of mixed solution of choline eutectic solvent and water, extracting, centrifuging or filtering, collecting supernatant or filtrate, diluting with organic solvent to precipitate eutectic solvent, centrifuging or filtering to remove, and concentrating supernatant or filtrate to obtain flos Trollii extract rich in orientin, orientin-2 "-O-beta-L-galactoside and vitexin.
3. The expression of claim 2 is [ N (CH)3)3CH2CH2OH]+[X·zY]－The application of the choline eutectic solvent in selectively extracting the flavone C-glycosides in the globeflower is characterized in that: the volume ratio of the choline eutectic solvent to water is 2-4: 1.
4. The expression of claim 2 is [ N (CH)3)3CH2CH2OH]+[X·zY]－The application of the choline eutectic solvent in selectively extracting the flavone C-glycosides in the globeflower is characterized in that: the extraction method is ultrasonic extraction.
5. The expression of claim 2 is [ N (CH)3)3CH2CH2OH]+[X·zY]－Selective extraction of choline eutectic solventThe application of taking flavone C-glycosides from trollius chinensis is characterized in that: the organic solvent is ethanol.
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| CN108467427B (en) * | 2018-03-27 | 2020-03-10 | 南通纺织丝绸产业技术研究院 | Method for preparing keratin by dissolving wool with eutectic solvent |
| CN111019004A (en) * | 2018-10-10 | 2020-04-17 | 天津科技大学 | Method for preparing cellulose nanocrystals by hydrolyzing acidic eutectic solvent under catalysis of metal salt |
| CN113648341B (en) * | 2021-09-18 | 2022-05-10 | 中国热带农业科学院热带作物品种资源研究所 | Method for extracting flavonoid components from beautiful millettia root |
| CN113735919B (en) * | 2021-09-28 | 2023-03-31 | 深圳市真味生物科技有限公司 | Method for preparing naringin dihydrochalcone sweetener by adding hydrogen into pummelo peel extract and prepared naringin dihydrochalcone sweetener |
| CN113817006B (en) * | 2021-09-30 | 2023-08-18 | 华南理工大学 | Method for extracting anoectochilus formosanus glycoside based on deep eutectic solvent |
| CN114053338B (en) * | 2021-10-18 | 2023-01-17 | 内蒙古大学 | Method for optimizing extraction process of flavonoid components of short-petal trollius chinensis bunge |
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| CN104887723A (en) * | 2015-06-18 | 2015-09-09 | 天津理工大学 | Method for extracting flavonoids from ginkgo biloba leaves with deep eutectic solvent |
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