CN113336814B - Method for extracting quercetin from pimpinella brachycarpa and application of quercetin - Google Patents
Method for extracting quercetin from pimpinella brachycarpa and application of quercetin Download PDFInfo
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Abstract
The invention relates to the technical field of extraction of effective components of plants, in particular to a method for extracting quercetin from pimpinella brachycarpa and application thereof, wherein the method comprises the following steps: (1) drying pimpinella brachycarpa, crushing, adding a solvent A for extraction, filtering to obtain filter residues and a filtrate, concentrating and drying the filtrate, and mixing with water to obtain a mixed solution; the solvent A is a mixed solvent of 85-95% ethanol and acetone; (2) adding the mixed solution into a solvent B, a solvent C and a solvent D in sequence for extraction to obtain an extract liquor 1, an extract liquor 2 and an extract liquor 3 respectively; (3) concentrating the extract liquid 3, passing through a silica gel column, adding a solvent E for elution, collecting eluent, and drying to obtain the product. The invention has the advantages of high yield, simple preparation process and good antioxidant effect.
Description
Technical Field
The invention relates to the technical field of extraction of plant effective components, and particularly relates to a method for extracting quercetin from pimpinella brachycarpa and application of the quercetin.
Background
Pimpinella brachycarpa (Kom.) Nakai is a perennial herb of Pimpinella brachycarpa of Umbelliferae, and is grown in under-forest grass clumps. The pimpinella brachycarpa is a vegetable used as both medicine and food, is well received in the international market, has wide distribution, large storage capacity, high nutrition, delicious taste and unique flavor, and is mostly eaten.
The root and fruit of Pimpinella brachycarpa contains isolariciresinol diglucoside, and can be used for dispersing wind heat, lowering blood pressure and eliminating phlegm, and treating common cold, cough, fullness sensation in chest and hypochondrium, and bronchitis. At present, the research on pimpinella brachycarpa is mainly based on a cultivation technology, and nutrient component analysis, volatile component analysis, preservation technology research and crude extract antibacterial pharmacological action research are rare. Although the health care value of pimpinella brachycarpa is generally accepted by people, the research on the active ingredients and the health care effect is few, and particularly the research on the health care effects such as chemical ingredients of the whole herbs and antioxidation is rarely reported.
In recent years, researches show that the chemical components of pimpinella brachycarpa mainly comprise terpenoids, volatile oil, coumarin, saponin, flavone and other compounds. Terpenes and volatile oils include monoterpenes, sesquiterpenes, dimeric sesquiterpenes, triterpenes and their oxygenated derivatives, most of which are present in volatile oils. The flavonoids include luteolin glycoside, robinin glycoside, luteolin, apigenin, etc. Other components including polysaccharides, sterols, fatty acids, proteins, amino acids, vitamins, etc., play a vital role in the regulation of human immunity.
Quercetin (English Quercitririn) is a flavonoid monomer compound widely existing in plants, and has multiple pharmacological actions of resisting oxidation, resisting tumor, reducing blood sugar, reducing blood lipid, etc. Quercetin has certain anti-inflammatory activity, and is mainly expressed in the inhibition of inflammatory factors.
Qianchui, separation and identification of chemical components of pimpinella brachycarpa and research on in vitro antioxidant activity [ D ] Jilin university, 2013. discloses separation and identification of chemical components of pimpinella brachycarpa and research on in vitro antioxidant activity, wherein quercetin is obtained by separation, and the specific separation process is as follows:
(1) drying Pimpinella brachycarpa in shade, and pulverizing into powder (40-60 mesh). Weighing pimpinella brachycarpa powder, adding 90% ethanol solution with the mass: volume of 1:7, carrying out reflux extraction for 3 times and 2 hours each time, filtering, collecting extract, and concentrating under reduced pressure to obtain ethanol extract.
(2) Taking 1.025kg of the ethanol extract, adding distilled water into the ethanol extract according to the mass: volume ratio of 1:1, stirring and suspending, adding petroleum ether for extraction, recovering the extract, extracting for 3 times, recovering the petroleum ether under reduced pressure, and drying to obtain 25g of petroleum ether extract; adding ethyl acetate into the mixture according to the mass ratio of the ethanol extract to the mixture (1: 1) for extraction, recovering the extract, extracting for 3 times, recovering ethyl acetate under reduced pressure, and drying to obtain 125g of ethyl acetate extract; according to the mass (ethanol extract): adding water saturated n-butanol at a volume of 1:1 for extraction, recovering the extract, extracting for 3 times, recovering n-butanol under reduced pressure, and drying to obtain 60g of n-butanol extract; the aqueous solution was recovered under reduced pressure and dried to obtain 760g of an aqueous extract.
(3) Taking the n-butanol extract, mixing the n-butanol extract with 100-200-mesh silica gel according to the mass ratio of 1:1, and putting the mixture into a silica gel column with the mass 10 times that of the extract for separation. Gradient eluting with ethyl acetate and methanol (20:1 → 0:1) as eluent, recovering under reduced pressure 250mL of each eluate, and performing thin layer chromatography to obtain 9 major components, one of which is quercetin.
However, the yield of the quercetin prepared by the method is low, so that the resource waste is caused, the preparation process is complex, thin-layer chromatography analysis is required, and the industrial production is not facilitated.
Therefore, it is necessary to develop a method for extracting quercetin from pimpinella brachycarpa to solve the above-mentioned technical problems.
Disclosure of Invention
The invention aims to overcome the defects of the prior art and provides a method for extracting quercetin from pimpinella brachycarpa and application thereof, wherein the method is high in yield, simple in preparation process and good in antioxidant effect.
The invention is realized by the following technical scheme:
a method for extracting quercetin from Pimpinella brachycarpa comprises the following steps:
(1) drying pimpinella brachycarpa, crushing, adding a solvent A for extraction, filtering to obtain filter residues and a filtrate, concentrating and drying the filtrate, and mixing with water to obtain a mixed solution; the solvent A is a mixed solvent of 85-95% ethanol and acetone;
(2) adding the mixed solution into a solvent B, a solvent C and a solvent D in sequence for extraction to obtain an extract liquor 1, an extract liquor 2 and an extract liquor 3 respectively;
(3) concentrating the extract liquid 3, passing through a silica gel column, adding a solvent E for elution, collecting eluent, and drying to obtain the product.
Preferably, the volume-to-mass ratio of the solvent A to the pimpinella brachycarpa in the step (1) is 3-5 mL/g.
Preferably, the extraction temperature in the step (1) is 40-60 ℃, the extraction times are 1-3 times, and the extraction time is 2-4 h.
Preferably, the mass ratio of ethanol to acetone in the solvent A is 2-5: 1-3.
Preferably, in the step (1), the Pimpinella brachycarpa is dried and crushed, then the solvent A in an amount which is 3-5 times that of the Pimpinella brachycarpa is added to be extracted for 1-3 times at the temperature of 40-60 ℃ and 2-4h each time, filtration is carried out to obtain filter residue and filtrate, and the filtrate is concentrated and dried and then mixed with water in an amount which is 3-5 times that of the filtrate to obtain a mixed solution.
More preferably, step (1) comprises the steps of:
drying and crushing Pimpinella brachycarpa, adding 3-5 times of solvent A (the solvent A is a mixed solvent of 85-95% ethanol and acetone, the mass ratio of the solvent A to the solvent A is 2-5:1-3) to extract at 40-60 ℃ for 1-3 times, each time for 2-4h, filtering to obtain filter residue and filtrate, concentrating and drying the filtrate, and mixing with 3-5 times of water to obtain a mixed solution.
Preferably, the solvent B is petroleum ether.
Preferably, the solvent C is an ethyl acetate-toluene mixed solvent, and the volume ratio of the two is 2-4: 1.
Preferably, the solvent D is water-saturated n-butanol.
More preferably, the step (2) comprises the steps of:
adding 1-3 times of petroleum ether, solvent C (ethyl acetate-toluene mixed solvent with volume ratio of 2-4:1) and water saturated n-butanol into the mixed solution in sequence, and extracting to obtain extract 1, extract 2 and extract 3.
The sequential extraction steps comprise adding petroleum ether for extraction for 1-2h to obtain an extract liquid 1; adding the residual mixed solution after extraction into a solvent C for extraction for 1-2h to obtain an extract liquid 2; and finally, adding water saturated n-butanol into the residual mixed solution after the extraction liquid 2 is removed for extraction for 1-2h to obtain an extraction liquid 3.
Preferably, the extract 3 is concentrated to have a relative density of 1.2-1.3 at 60 ℃ in the step (3), and the extract is passed through a 100-mesh 200-mesh silica gel column, eluted by adding a solvent E, collected and dried to obtain the compound.
Preferably, the solvent E in step (3) is at least one of water, ethanol and ethyl acetate.
More preferably, the step (3) is sequentially eluted by using a mixed solvent of water, 30% ethanol and ethyl acetate-70-95% ethanol.
More preferably, the volume ratio of the ethyl acetate to the 70-95% ethanol in the mixed solvent is 1.2-4.5: 1.
More preferably, collecting the eluent eluted by the mixed solvent of ethyl acetate and 70-95% ethanol.
More preferably, the step (3) includes the steps of:
concentrating the extract 3 to the relative density of 1.2-1.3 at 60 ℃, passing through a 100-mesh silica gel column with 200 meshes, sequentially eluting by using a mixed solvent of water, 30% ethanol and ethyl acetate-70-95% ethanol (the volume ratio is 1.2-4.5:1), collecting the eluent obtained by eluting by using the mixed solvent of ethyl acetate-70-95% ethanol, and drying to obtain the extract.
More preferably, the method for extracting quercetin from pimpinella brachycarpa comprises the following steps:
(1) drying and crushing Pimpinella brachycarpa, adding 3-5 times of solvent A (the solvent A is a mixed solvent of 85-95% ethanol and acetone with the mass ratio of 2-5:1-3) to extract at 40-60 deg.C for 1-3 times (2-4 h each time), filtering to obtain filter residue and filtrate, concentrating and drying the filtrate, and mixing with 3-5 times of water to obtain a mixed solution;
(2) sequentially adding 1-3 times of petroleum ether, solvent C (ethyl acetate-toluene mixed solvent with volume ratio of 2-4:1) and water saturated n-butanol into the mixed solution for extraction to obtain extract 1, extract 2 and extract 3;
(3) concentrating the extract 3 to the relative density of 1.2-1.3 at 60 ℃, passing through a 100-mesh silica gel column with 200 meshes, sequentially eluting by using a mixed solvent of water, 30% ethanol and ethyl acetate-70-95% ethanol (the volume ratio is 1.2-4.5:1), collecting the eluent obtained by eluting by using the mixed solvent of ethyl acetate-70-95% ethanol, and drying to obtain the extract.
The present invention also relates to a composition comprising quercetin.
Preferably, the composition comprises the following components in parts by weight: 3-8 parts of coenzyme Q10, 15-25 parts of L-carnitine, 5-10 parts of quercetin, 4-12 parts of galactomannan and 1-3 parts of lycopene.
The invention also relates to application of the quercetin extracted by the method in preparing an antioxidant medicine.
The invention has the beneficial effects that:
the invention optimizes the extraction process of the quercetin, particularly optimizes the composition of the extraction solvent, the extraction solvent and the elution solvent, so that the prepared quercetin has high yield, avoids the waste of resources and ensures the purity of the quercetin to a certain extent.
The composition provided by the invention has excellent antioxidant effect, and particularly, the quercetin prepared by the invention has the advantage that the antioxidant effect is remarkably improved.
Detailed Description
The invention will be further described with reference to specific embodiments, and the advantages and features of the invention will become apparent as the description proceeds. These examples are illustrative only and do not limit the scope of the present invention in any way. It will be understood by those skilled in the art that various changes in form and details may be made therein without departing from the spirit and scope of the invention, and that such changes and modifications may be made without departing from the spirit and scope of the invention.
Example 1
A method for extracting quercetin from Pimpinella brachycarpa comprises the following steps:
(1) drying and crushing Pimpinella brachycarpa, adding 3 times of solvent A (the solvent A is a mixed solvent of 85% ethanol and acetone, the mass ratio of the solvent A to the acetone is 2:1) and extracting at 40 ℃ for 3 times, 2h each time, filtering, combining to obtain filter residue and filtrate respectively, concentrating and drying the filtrate, and mixing with 3 times of water to obtain a mixed solution;
(2) sequentially adding 1 time of petroleum ether, a solvent C (ethyl acetate-toluene mixed solvent with the volume ratio of 2:1) and water saturated n-butanol into the mixed solution for extraction to respectively obtain an extract 1, an extract 2 and an extract 3;
(3) concentrating the extract 3 to relative density of 1.2 at 60 deg.C, passing through 100 mesh silica gel column, sequentially eluting with water, 30% ethanol and mixed solvent of ethyl acetate-70% ethanol (volume ratio of 2:1), collecting eluate eluted with mixed solvent of ethyl acetate-70% ethanol, and drying.
Example 2
A method for extracting quercetin from Pimpinella brachycarpa comprises the following steps:
(1) drying and crushing Pimpinella brachycarpa, adding 5 times of solvent A (the solvent A is a mixed solvent of 95% ethanol and acetone, the mass ratio of the solvent A to the acetone is 5:3) and extracting at 60 ℃ for 1 time for 4 hours, filtering to obtain filter residue and filtrate, concentrating and drying the filtrate, and mixing with 5 times of water to obtain a mixed solution;
(2) sequentially adding 3 times of petroleum ether, a solvent C (ethyl acetate-toluene mixed solvent with the volume ratio of 4:1) and water saturated n-butanol into the mixed solution for extraction to respectively obtain an extract 1, an extract 2 and an extract 3;
(3) concentrating the extract 3 to relative density of 1.3 at 60 deg.C, passing through 200 mesh silica gel column, sequentially eluting with water, 30% ethanol and ethyl acetate-95% ethanol mixed solvent (volume ratio of 4:1), collecting eluate eluted with ethyl acetate-95% ethanol mixed solvent, and drying to obtain the final product.
Example 3
A method for extracting quercetin from Pimpinella brachycarpa comprises the following steps:
(1) drying and crushing Pimpinella brachycarpa, adding 4 times of solvent A (the solvent A is a mixed solvent of 90% ethanol and acetone, the mass ratio of the solvent A to the acetone is 3:2) and extracting at 50 ℃ for 2 times, each time for 3 hours, filtering, combining to obtain filter residue and filtrate respectively, concentrating and drying the filtrate, and mixing with 4 times of water to obtain a mixed solution;
(2) sequentially adding 2 times of petroleum ether, a solvent C (ethyl acetate-toluene mixed solvent with the volume ratio of 3:1) and water saturated n-butanol into the mixed solution for extraction to respectively obtain an extract 1, an extract 2 and an extract 3;
(3) concentrating the extract 3 to relative density of 1.25 at 60 deg.C, passing through 100 mesh silica gel column, sequentially eluting with water, 30% ethanol and ethyl acetate-85% ethanol mixed solvent (volume ratio of 3:1), collecting eluate eluted with ethyl acetate-85% ethanol mixed solvent, and drying to obtain the final product.
Example 4
The composition comprises the following components in parts by weight: 3 parts of coenzyme Q10, 15 parts of L-carnitine, 5 parts of quercetin (prepared in example 1), 4 parts of galactomannan, and 1 part of lycopene.
Example 5
The composition comprises the following components in parts by weight: 8 parts of coenzyme Q10, 25 parts of L-carnitine, 10 parts of quercetin (prepared in example 2), 12 parts of galactomannan, and 3 parts of lycopene.
Example 6
The composition comprises the following components in parts by weight: 5 parts of coenzyme Q10, 20 parts of L-carnitine, 8 parts of quercetin (prepared in example 3), 8 parts of galactomannan, and 3 parts of lycopene.
Comparative example 1
The difference from example 3 is only that the composition of solvent A is different, only 90% ethanol, the total volume is unchanged, and the rest conditions are the same.
Comparative example 2
The difference from example 3 is only that the composition of solvent C is different, only ethyl acetate, the total volume is not changed, and the other conditions are the same.
Comparative example 3
The difference from example 3 is only that the elution order in step (3) is changed, and the elution is carried out by using a mixed solvent of 30% ethanol, water and ethyl acetate-85% ethanol (volume ratio is 3: 1).
Comparative example 4
The difference from the example 6 is only that 8 parts of quercetin is replaced by 5 parts of coenzyme Q10 and 3 parts of lycopene, and the rest conditions are the same, and the specific conditions are as follows:
the composition comprises the following components in parts by weight: 10 parts of coenzyme Q10, 20 parts of L-carnitine, 8 parts of galactomannan and 6 parts of lycopene.
Comparative example 5
The differences from the example 6 only lie in that 5 parts of coenzyme Q10 and 3 parts of lycopene are replaced by 8 parts of quercetin, and the rest conditions are the same, and the specific conditions are as follows:
the composition comprises the following components in parts by weight: 20 parts of L-carnitine, 16 parts of quercetin (prepared in example 3) and 8 parts of galactomannan.
Comparative example 6
The difference from example 6 is only that quercetin prepared in example 3 was replaced with quercetin prepared in comparative example 1 of equal mass.
Comparative example 7
The difference from example 6 is only that quercetin prepared in example 3 was replaced with equal quality of commercially available quercetin (522-12-3, purity 99%, available from Guanao Biotech Co., Ltd., North lake).
Test example 1
The results of the quercetin yield test performed in examples 1 to 3 and comparative examples 1 to 3 are shown in Table 1.
TABLE 1 Quercetin yield test results
| Sample (I) | Yield% |
| Example 1 | 82.9 |
| Example 2 | 83.4 |
| Example 3 | 83.7 |
| Comparative example 1 | 72.1 |
| Comparative example 2 | 74.6 |
| Comparative example 3 | 77.8 |
Test example 2
The compositions of examples 4 to 6 and comparative examples 4 to 7 were subjected to an antioxidant effect test. The specific test method is as follows:
DPPH free radical scavenging experiment
DPPH is prepared into 200 mu mo1/L stock solution by absolute ethyl alcohol, and the stock solution is refrigerated and stored in dark. The compositions of examples 4-6 and comparative examples 4-7 were formulated in DMSO to give sample solutions at concentrations of 2.5, 5 and 10mg/mL, respectively. Adding 50 μ L of sample solution into 200 μ L of prepared DPPH stock solution, reacting at room temperature for 30min, measuring absorbance at 520nm, and recording as ASample (I). Measuring blank absorbance value A by using DMSO instead of sample solutionAir conditionerEthanol is used to replace DPPH solution, and the background absorbance A is measuredEthanolThree times, DPPH clearance activity SC ═ AAir conditioner-(ASample (I)-AEthanol)]/AAir conditionerX 100%, its antioxidant activity is half inhibition rate EC50And (4) showing.
ABTS+Cleaning experiment
Preparing 14mmol/L ABTS and 4.95mmol/L potassium persulfate solution from phosphoric acid buffer solution, mixing at the same volume to prepare ABTS+The stock solution was left at room temperature for 24h in the dark. The compositions of examples 4-6 and comparative examples 4-7 were formulated in DMSO to give sample solutions at concentrations of 2.5, 5 and 10mg/mL, respectively. 300 μ L of sample solution and 900 μ L of ABTS+Mixing the stock solution at room temperature for 1min, measuring absorbance at 732nm, and recording as ASample (I). Measuring blank absorbance value A by using DMSO instead of sample solutionAir conditionerAnd replacing ABTS solution with ethanol, and measuring the background absorbance AEthanolThree times of determination, the ABTS free radical scavenging activity rate SC ═ AAir conditioner-(ASample (I)-AEthanol)]/AAir conditionerX 100%, its antioxidant activity is half inhibition rate EC50And (4) showing.
The results are shown in Table 2.
TABLE 2
The quercetin products prepared in the embodiments 1-3 of the invention are not subjected to thin-layer chromatography analysis, and the preparation process is simpler. Moreover, through detection, the product extracted by the method contains other effective components besides the effective component of the quercitrin. Example 6 compared with comparative example 7 (quercetin with a purity of 99%), the antioxidant effect is remarkably improved, which is confirmed by that the quercetin product prepared by the invention is a mixed extract containing a plurality of effective components and applied to the preparation of the composition of the invention, and the antioxidant effect is remarkably improved by the synergistic effect of the quercetin product and other components.
The above detailed description is specific to one possible embodiment of the present invention, and the embodiment is not intended to limit the scope of the present invention, and all equivalent implementations or modifications without departing from the scope of the present invention should be included in the technical scope of the present invention.
Claims (3)
1. The composition is characterized by comprising the following components in parts by weight: 3-8 parts of coenzyme Q10, 15-25 parts of L-carnitine, 5-10 parts of quercetin, 4-12 parts of galactomannan and 1-3 parts of lycopene;
the quercetin is extracted from Pimpinella brachycarpa, and the extraction method comprises the following steps:
(1) drying pimpinella brachycarpa, crushing, adding a solvent A for extraction, filtering to obtain filter residues and a filtrate, concentrating and drying the filtrate, and mixing with water to obtain a mixed solution; the solvent A is a mixed solvent of 85-95% of ethanol and acetone, and the mass ratio of the ethanol to the acetone in the solvent A is 2-5: 1-3;
(2) adding the mixed solution into a solvent B, a solvent C and a solvent D in sequence for extraction to obtain an extract liquor 1, an extract liquor 2 and an extract liquor 3 respectively; the solvent B is petroleum ether; the solvent C is an ethyl acetate-toluene mixed solvent, and the volume ratio of the ethyl acetate to the toluene is 2-4: 1; the solvent D is water saturated n-butanol;
(3) concentrating the extract 3 to the relative density of 1.2-1.3 at 60 ℃, passing through a 100-mesh silica gel column with 200 meshes, sequentially adopting a mixed solvent of water, 30% ethanol and ethyl acetate-70-95% ethanol with the volume ratio of 1.2-4.5:1, eluting, collecting the eluent obtained by eluting with the mixed solvent of ethyl acetate-70-95% ethanol, and drying to obtain the extract.
2. The composition as claimed in claim 1, wherein the Pimpinella brachycarpa in step (1) is dried, crushed, added with 3-5 times of solvent A, extracted at 40-60 ℃ for 1-3 times, each time for 2-4h, filtered to obtain filter residue and filtrate, and the filtrate is concentrated, dried, and mixed with 3-5 times of water to obtain the mixture.
3. Use of a composition according to any one of claims 1-2 for the preparation of a medicament for anti-oxidant therapy.
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Address after: 130000 room 1103, Marriott Oriental Plaza, economic development zone, Changchun City, Jilin Province Applicant after: Jilin Haotai Health Industry Development Co.,Ltd. Address before: 130000 room 1103, Marriott Oriental Plaza, economic development zone, Changchun City, Jilin Province Applicant before: JILIN HAOTAI HEALTH INDUSTRY DEVELOPMENT Co.,Ltd. |
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| GR01 | Patent grant | ||
| GR01 | Patent grant |