CN102293811B - Extraction method of total coumarin and application of extracted total coumarin - Google Patents
Extraction method of total coumarin and application of extracted total coumarin Download PDFInfo
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Abstract
The invention, belonging to the technical field of extracting effective components of Chinese medicines, provides a method of extracting total coumarin from seed coats of caper euphorbia seeds, comprising the following steps: crushing the seed coats of caper euphorbia seeds into coarse powder, using petroleum ether to degrease to obtain the residue; carrying out extraction on the residue with ethanol or methanol to obtain the crude product of total coumarin; adding potassium hydroxide, adjusting the pH value to 7-8, filtering, adding hydrochloric acid, adjusting the pH value to 2-3, keeping in cold storage at the temperature of 3-5 DEG C for 12-16 h, carrying out extraction filtration, throwing away the filtrate, and carrying out vacuum drying to obtain the total coumarin. The obtained total coumarin can be used for preparing medicines for curing hyperuricemia. The total coumarin extracted from the seed coats of caper euphorbia seeds, so that the resource can be fully utilized, the utilization rate of caper euphorbia seeds is improved, and the yield is increased. The method has the advantages of simple extraction method, low cost, easy operation, and good repeatability, and the total coumarins has high purity of more than 80 %. The total coumarin has good treatment effect on hyperuricemia, and has high content of the effective components, good drug stability, outstanding effect of lowering uric acid, wide application range, and little side effects.
Description
Technical field
The invention belongs to the extract Technique of Chinese Medicine Efficacious Ingredient field, particularly a kind of extracting method that extracts total coumarins from Semen Euphorbiae kind skin, also relate to the application of the total coumarins of extracting.
Background technology
Coumarin kind compound is the ubiquitous secondary metabolite of occurring in nature, mainly contain the compositions such as aesculetin, aseculin, daphnetin, aseculin can reduce serum uric acid level in the hyperuricemia animal body, the rat arthritis that on Carrageenan, dextran, 5-HT and histamine cause has inhibitory action, can suppress again erythematous response, rat granuloma that Cavia porcellus ultraviolet radiation back causes and must form (cotton pellet method), the capillary permeability that histamine causes increases.Aesculetin can significantly suppress the capillary permeability increase that histamine causes.Daphnetin has anti-inflammatory and analgesic effect.
Semen Euphorbiae is the seed of euphorbia plant Euphorbia lathyris EupHorbia lathyris L., the detumescence of relieving oedema or abdominal distension through diuresis or purgation, the effect of removing blood stasis eliminating stagnation contains the compositions such as fatty oil, Coumarins composition such as aesculetin, aseculin, daphnetin in kernel, but content is lower, 0.04%～0.36%.And kind skin (weight accounts for 60% left and right of the seed) past of Semen Euphorbiae outside pitchy partly removes as impurity always, we find that in research process in kind of skin, total coumarin content is higher, generally 1.7%～3.8%, it is a kind of plant resources of potential extraction Coumarins composition.
Hyperuricemia shows as blood or urine uric acid excessive concentration, and the main cause of its generation has two aspects, on the one hand because the xanthine oxidase Developmental and Metabolic Disorder causes uric acid production too much, on the other hand because kidney disease causes underexcretion.Urate deposition in the joint, soft tissue and kidney place, cause arthritis, lithangiuria and kidney disease, cause gout repeatedly to be shown effect.In addition, the M ﹠ M of the diseases such as hyperuricemia and cardiovascular is also closely related, is a kind of disease that has a strong impact on publilc health.Along with the rapid raising of living standard, the sickness rate of China's hyperuricemia is lasting ascendant trend, and basis and the drug research of hyperuricemia also become one of focus day by day.At present, the treatment of hyperuricemia and gout needs anti-inflammatory agent to alleviate the symptoms such as red, swollen, hot, pain of disease, and selects uricotelic drugs, xanthine oxidase inhibitor to alleviate hyperuricemia on the disease progression different phase, controls PD.At present, clinical medicine commonly used has allopurinol (Sulfonate Demeglumine), benzbromarone (vertical markon is celestial) etc.Allopurinol has certain limitation when prevention and treatment gout, only have uric acid when accumulation when more obvious in circulation allopurinol hinder the effect of uric acid biosynthesis and just can be embodied, and can produce toxic and side effects such as skin allergy, hepatitis, life-threatening allergy syndrome etc.The benzbromarone life-time service has limited its safe handling to a certain extent to the kidney toxic side effect.Therefore, the novel anti-hyperuricemia of searching and gout medicine are still the focuses of study of pharmacy from natural resources.
Summary of the invention
In order to overcome the above problems, the invention provides a kind of extracting method that extracts total coumarins from Semen Euphorbiae kind skin, this extracting method is simple, good reproducibility, extract purity are high.
The present invention also provides the application of the total coumarins of extracting.
The present invention is achieved in the following ways:
A kind of extracting method of total coumarins comprises the following steps:
(1) defat: Semen Euphorbiae kind corium farinosum is broken into coarse powder, uses defat with petroleum ether to get residue;
(2) extract: residue is with ethanol or methanol extraction, and decompression filtrate recycling ethanol or methanol obtain the total coumarins crude product.
(3) purification: add potassium hydroxide in the total coumarins crude extract that obtains, the limit edged stirs, and transferring pH is 7～8, filters, add hydrochloric acid in filtrate, the limit edged stirs, transfer pH be 2～3,3～5 ℃ cold preservation 12-16 hour, sucking filtration, discard filtrate, the yellow solid vacuum drying with obtaining namely gets total coumarins.
In step (1), petroleum ether used is 30～60 ℃ or 60～90 ℃ boiling range specifications, and residue is flung to petroleum ether.
In step (2), the ethanol concentration of volume percent is 70～95%, and every gram coarse powder adds 10mL ethanol or methanol.
Use ethanol or methanol heating and refluxing extraction or supersound extraction 2～3 times, each 1～2 hour.
Use 70% alcohol heating reflux to extract 3 times, each 2h.
In step (3), the concentration of potassium hydroxide or hydrochloric acid is 1-2wt%.
The vacuum drying condition be drying 4 hours under 60～70 ℃, 0.07～0.09MP pressure in step (3).
Use defat with petroleum ether for using petroleum ether to carry out cable-styled defat in step (1).
In step (1), Semen Euphorbiae kind skin uses high speed disintegrator to be ground into 20～40 purpose coarse powder after removing impurity, then uses the cable-styled defat of petroleum ether colourless to petroleum ether extract.
The total coumarins that described extracting method obtains is for the preparation of the medicine for the treatment of hyperuricemia disease.
Beneficial effect of the present invention:
1, extract total coumarins from Semen Euphorbiae kind skin, can take full advantage of resource, improve the utilization rate of Semen Euphorbiae, additional income;
2, extracting method is simple, and cost is low, and is easy to operate, and repeatability is good, and the total coumarins purity that obtains is high, and purity is more than 80%;
3, the total coumarins that obtains has good therapeutic effect to hyperuricemia, active constituent content is high, medicine stability good, the uric acid resisting effect significantly, have wide range of applications, toxic and side effects is little.
Description of drawings
The total coumarins TLC that accompanying drawing 2 extracts from Semen Euphorbiae kind skin for the present invention differentiates the figure that inspects under daylight,
The total coumarins TLC that accompanying drawing 3 extracts from Semen Euphorbiae kind skin for the present invention differentiates the figure that inspects under ultra-violet lamp (365nm),
In figure: 1 is the daphnetin reference substance, and 2 is the aesculetin reference substance, and 3 is the aseculin reference substance, 4～7 total coumarinss for the inventive method extraction.
The specific embodiment
The concentration of alcohol of mentioning in following examples all refers to concentration of volume percent, and other concentration all refers to weight percent concentration.
The present embodiment extraction solvent used is 70% ethanol, adopts hot reflux to extract, and extracts each 2 hours 3 times.
Its preparation method is:
A), Semen Euphorbiae kind skin is removed impurity after, be ground into 20～40 purpose coarse powder.Get the 100g powder, put in cable type extractor according, carry out cable-styled defat 3 hours with the petroleum ether of 30～60 ℃ of boiling range specifications colourless to petroleum ether extract,, discard petroleum ether extract, residue is flung to petroleum ether.
B), residue adds 70% ethanol 1000mL heating and refluxing extraction 3 times, each 2 hours, filter, decompression filtrate recycling ethanol obtains the total coumarins crude product.
C), the total coumarins crude extract that obtains adds 1% potassium hydroxide solution, the stirring of limit edged, accent pH=7, filter, discard insoluble matter, filtrate adds 1% hydrochloric acid again, the limit edged stirs, transfer pH=3,3～5 ℃ of cold preservation 12 hours, sucking filtration, discard filtrate, at 0.09MP, 60 ℃ of vacuum dryings 4 hours namely get total coumarins with the yellow solid that obtains.
The present embodiment extraction solvent used is 80% ethanol, adopts hot reflux to extract, and extracts each 2 hours 2 times.
Its preparation method is:
A), Semen Euphorbiae kind skin is removed impurity after, be ground into 20～40 purpose coarse powder.Get the 100g powder, put in cable type extractor according, carry out cable-styled defat 3 hours with the petroleum ether of 60～90 ℃ of boiling range specifications colourless to petroleum ether extract, discard petroleum ether extract, residue is flung to petroleum ether.
B), residue adds 80% ethanol 1000mL heating and refluxing extraction 2 times, each 2 hours, filter, decompression filtrate recycling ethanol obtains the total coumarins crude product.
C), the crude extract that obtains adds 2% potassium hydroxide, the stirring of limit edged, accent pH=8, filter, discard insoluble matter, filtrate adds 2% hydrochloric acid again, the limit edged stirs, transfer pH=2,3～5 ℃ of cold preservation 16 hours, sucking filtration, discard filtrate, at 0.07MP, 70 ℃ of vacuum dryings 4 hours namely get total coumarins with the yellow solid that obtains.
The present embodiment extraction solvent used is 95% ethanol, adopts hot reflux to extract, and extracts each 2 hours 3 times.
Its preparation method is:
A), Semen Euphorbiae kind skin is removed impurity after, be ground into 20～40 purpose coarse powder.Get the 100g powder, put in cable type extractor according, colourless to petroleum ether extract with the cable-styled defat of the petroleum ether of 30～60 ℃ of boiling range specifications 3 hours, discard petroleum ether extract, residue is flung to petroleum ether.
B), the residue after defat adds 95% ethanol 1000mL heating and refluxing extraction 3 times, each 2 hours, filter, decompression filtrate recycling ethanol obtains the total coumarins crude product.
C), the crude extract that obtains adds 1% potassium hydroxide, the stirring of limit edged, accent pH=7, filter, discard insoluble matter, filtrate adds 1% hydrochloric acid again, the limit edged stirs, transfer pH=3,3～5 ℃ of cold preservation 12 hours, sucking filtration, discard filtrate, at 0.09MP, 60 ℃ of vacuum dryings 4 hours namely get total coumarins with the yellow solid that obtains.
The present embodiment extraction solvent used is 95% ethanol, adopts ultrasonic method to extract, and extracts each 1 hour 3 times.
Its preparation method is:
A), Semen Euphorbiae kind skin is removed impurity after, be ground into 20～40 purpose coarse powder.Get the 100g powder, put in cable type extractor according, colourless to petroleum ether extract with the cable-styled defat of the petroleum ether of 30～60 ℃ of boiling range specifications 3 hours, discard petroleum ether extract, residue is flung to petroleum ether.
B), residue adds 95% ethanol 1000mL supersound extraction 3 times, each 1 hour, filter, decompression filtrate recycling ethanol obtains the total coumarins crude product.
C), the crude extract that obtains adds 1% potassium hydroxide, the stirring of limit edged, accent pH=7, filter, discard insoluble matter, filtrate adds 1% hydrochloric acid again, the limit edged stirs, transfer pH=3,3～5 ℃ of cold preservation 16 hours, sucking filtration, discard filtrate, at 0.07MP, 70 ℃ of vacuum dryings 4 hours namely get total coumarins with the yellow solid that obtains.
One, the selection of extraction process condition
1.1 determine the theoretical foundation of extracting method: according to the chemical property of Semen Euphorbiae related documents and Coumarins composition, determined its extraction process through repetition test.
1.2 the preferred extraction process of orthogonal experiment
Through prerun, it is high that ethanol refluxing process extracts than ultrasonic method the total coumarin content record, still adopt ethanol refluxing process to extract.Select the concentration of alcohol (A) of major effect extraction efficiency, extraction time (B), extraction time (C) be the investigation factor, and total coumarin content is as investigating index, employing L in the extract
9(3
4) orthogonal table tests, the factor level table sees Table 1.
Table 1 factor level table
Operational approach:
Semen Euphorbiae kind corium farinosum is broken into 20～40 purpose coarse powder, and precision takes 4 parts, and every part of 0.1g puts into respectively filtration paper cylinder, adds the petroleum ether of 30～60 ℃ of boiling range specifications in cable type extractor according, and defat 3h discards petroleum ether liquid.Residue is flung to solvent, then according to planning in orthogonal test table, adds the ethanol 10mL of variable concentrations, water-bath reflux, extract, different time and different number of times let cool, and filter, the filtrate evaporate to dryness, shakes up in the 10mL measuring bottle with the dissolve with methanol standardize solution, get 0.5mL in the 10mL measuring bottle, add methanol constant volume, take aesculetin as reference substance, adopt ultraviolet spectrophotometry to measure absorbance in 350nm, total coumarin content in calculation sample the results are shown in Table 2.
Table 2L
9(3
4) orthogonal test planning chart and result
Intuitive analysis shows, each factor extreme difference R
A＞R
C＞R
B, the factor that affects total coumarins extraction ratio in Semen Euphorbiae kind skin is followed successively by concentration of alcohol＞extraction time＞extraction time, and concentration of alcohol is main factor, and extraction time and extraction time are the minor effect factor.Total coumarin content is more high better, for the A factor, and selection level 2, namely concentration of alcohol is 70%.For the B factor, selection level 2 namely extracted 2 hours at every turn.For the C factor, selection level 2 namely extracts 3 times.The optimum extraction process that optimizes is combined as A
2B
2C
2, after namely planting the skin defat, with 70% ethanol extraction 3 times, each 2h.
1.3 demonstration test
Carry out the extraction of 3 batches of Semen Euphorbiae kind skins by the optimised process that optimizes, press ultraviolet spectrophotometry and measure its absorbance in the 350nm place, calculate total coumarin content.Three batch sample total coumarin contents are respectively 3.83%, 3.79% and 3.82% as a result, and relative standard deviation RSD% is 0.75%, illustrate that this extraction process repeatability is good.
1.4 purifying process
The total coumarins crude extract also contains other impurity, utilizes coumarin kind compound to contain the characteristic of phenolic hydroxyl group, adopt with alkali reaction and generate soluble-salt, then the character that is acidified with acid and separates out coumarin can reach the purpose of purification.
Get the ethanol extraction that obtains in 1.2, after decompression recycling ethanol, add 1% potassium hydroxide, the limit edged stirs, and transfers pH=7, filters, discard insoluble matter, filtrate adds 1% hydrochloric acid again, and the limit edged stirs, transfer pH=3,3～5 ℃ cold preservation 12-16 hour, sucking filtration, discard filtrate, at 0.09MP, 60 ℃ of vacuum dryings 4 hours namely get total coumarins with the yellow solid that obtains.
1.5 in three batches of extracts, total coumarin content is measured
The preparation of need testing solution: get respectively the total coumarins 5.5mg of three batches of extractions, 5.3mg, 5.5mg is dissolved in 10ml methanol, gets 0.2ml total coumarins solution and puts in 10ml, is diluted to scale and get final product with methanol respectively.
The preparation of aesculetin reference substance solution: get aesculetin reference substance solution (0.48mg/ml) 200 μ l, put in the 10ml measuring bottle, be diluted to concentration as the reference substance solution of 0.0096mg/ml take methanol.
The investigation of linear relationship: get approximately 12mg of aesculetin reference substance, accurately weighed, put in the 25ml measuring bottle, add the appropriate amount of ethanol slight fever and make dissolving, and be diluted to scale, shake up, concentration is 0.48mg/ml.Precision measures reference substance solution 100 μ l, 150 μ l, 200 μ l, 250 μ l, 300 μ l, be placed in respectively the 10ml measuring bottle, add ethanol dilution to scale, shake up, measure in 350nm, carry out regression Calculation with sample concentration and absorbance, get regression equation A=0.0162C-0.0009, r=0.9998 shows that aesculetin is good in 4.80 μ g/ml-14.4 μ g/ml scope internal linear relations, and measurement result is seen accompanying drawing 1.
Algoscopy: get reference substance solution respectively and need testing solution is appropriate, adopt ultraviolet spectrophotometry, measure absorbance in 350nm, total coumarin content in calculation sample the results are shown in Table 3.
Total coumarin content measurement result in three batches of extracts of table 3
1.6 in total coumarin extract, chemical composition thin layer chromatography (TLC) is differentiated
Contain aesculetin (aesculetin), aseculin (esculiw), bisaesculetin, isodigeranyl aesculetin, daphnetin etc. in bibliographical information Semen Euphorbiae kernel.According to above document, with reference to " Chinese pharmacopoeia lower method of a Semen Euphorbiae of version [discriminating] item in 2010 has been carried out the TLC discriminating to the chemical composition that may contain in Semen Euphorbiae kind skin total coumarin extract.
The preparation of daphnetin reference substance solution: get daphnetin reference substance (be purchased from Nat'l Pharmaceutical ﹠ Biological Products Control Institute, lot number 0900-200001 is for assay) appropriate, add dissolve with methanol, be made into the reference substance solution that concentration is 1mg/mL.Point sample amount 1m L.
The preparation of aesculetin reference substance solution: get aesculetin reference substance (be purchased from Nat'l Pharmaceutical ﹠ Biological Products Control Institute, lot number 110741-200506 is for assay) appropriate, add dissolve with methanol, be made into the reference substance solution that concentration is 1mg/mL.Point sample amount 1mL.
The preparation of aseculin reference substance solution: get aseculin reference substance (be purchased from Nat'l Pharmaceutical ﹠ Biological Products Control Institute, lot number 110740-200104 is for assay) appropriate, add dissolve with methanol, be made into the reference substance solution that concentration is 1mg/mL.Point sample amount 1mL.
The preparation of need testing solution: the total coumarins of getting the present invention's extraction is appropriate, adds dissolve with methanol, is made into the need testing solution that concentration is 1.2mg/mL.The point sample amount is respectively 2,4,8,10mL.
Lamellae: silica gel G-0.5% sodium carboxymethyl cellulose lamellae, thickness 0.4mm, 105 ℃ of activation 0.5h.
Developing solvent: toluene-ethyl acetate-formic acid (5: 4: 1),
Exhibition distance: 10cm,
Inspect: inspect under daylight and under ultra-violet lamp (365nm), the results are shown in accompanying drawing 2 and accompanying drawing 3.
From Fig. 2, Fig. 3 result as seen, inspect under daylight, daphnetin, aesculetin reference substance all show faint yellow speckle under daylight, aseculin reference substance speckle is colourless, has occurred the speckle of the same color corresponding with the aesculetin reference substance in the coumarin extract TLC chromatograph of different point sample amounts.Inspect under ultra-violet lamp (365nm), obvious blue-fluorescence speckle appears in aesculetin and aseculin reference substance, and the aobvious dark yellow speckle of daphnetin reference substance, the speckle that has occurred the same color corresponding with the aesculetin reference substance in the coumarin extract TLC chromatograph of different point sample amounts, equal appearance speckles corresponding with daphnetin and aseculin reference substance not tentatively illustrates to contain hardly aseculin and daphnetin in extract or both content is very low.
2. medicine effect of the present invention is learned result of the test
Inhibitory action to the antihyperuricemic disease mouse model:
60 of mices, female, body weight 20 ± 2g, be divided at random 6 groups: the total coumarins high dose group that in the total coumarins that the total coumarins low dose group that blank group, model control group, positive control allopurinol tablet group, the present invention extract, the present invention extract, dosage group, the present invention extract, 10 every group.By group administration, blank group and model control group gavage normal saline; The total coumarins high dose group gavage that in the total coumarins that the total coumarins low dose group that the present invention extracts, the present invention extract, dosage group, the present invention extract gives total coumarins 300mg/kg, 2100mg/kg and the 3000mg/kg that the present invention extracts, every day 1 time.The 4th day, positive controls gavage allopurinol tablet suspension 520mg/kg, all the other each groups continue administration, after the 5th day administration 1h, except the blank group, all the other are respectively organized Intraperitoneal injection of hypoxanthine 1000mg/kg and cause the hyperuricemia model, after injection 1h, each group is plucked eyeball and is got blood, the centrifugal 10min of 3000r/min gets serum, detects serum uric acid with automatic clinical chemistry analyzer.The results are shown in Table 4.
By table 4 result as seen, compare with the blank group, model control group mice serum uric acid content obviously raises, prompting modeling success.The total coumarins that the present invention extracts is high, middle dosage group and model control group comparison, the mice serum uric acid content obviously reduces (P＜0.001, P＜0.05), show that the total coumarins that the present invention extracts can obviously reduce the serum uric acid level of hyperuricemia mice, the uric acid suppression ratio of middle dosage group has reached 48.21%, and the uric acid suppression ratio of high dose group has reached 60.73%.
The different groups of table 4 on hyperuricemia mice serum uric acid content impact table (n=10, ± s)
Compare * P＜0.05 with the blank group; Compare with model control group
△P＜0.05,
△ △ △P＜0.001.
Publication number is the Chinese invention patent application of CN101181262A, aseculin, aesculetin, fraxin, the application of four kinds of compounds of fraxetin in the preparation medicament for restraining uric acid transportor URAT 1 are disclosed, but what extracting method of the present invention obtained is the mixture of multiple Coumarins composition, verify in above-mentioned experiment and contain aesculetin, also contain some other composition, and have to surpass 15% component and do not belong to total coumarins, these components also may be brought into play certain effect aspect the blood uric acid drug effect reducing.Although name of the present invention is called a kind of extracting method of total coumarins, but the application of component in preparation treatment antihyperuricemic disease drug that main inventive point of the present invention is to use extracting method of the present invention to extract from Semen Euphorbiae kind skin obtain not is just can obviously draw by the content of above-mentioned Patent Application Publication.
Claims (9)
1. the application of total coumarins in the medicine of preparation treatment hyperuricemia disease, described total coumarins is to obtain by following extracting method:
(1) defat: Semen Euphorbiae kind corium farinosum is broken into coarse powder uses defat with petroleum ether to get residue;
(2) extract: residue is with ethanol or methanol extraction, and decompression filtrate recycling ethanol or methanol obtain the total coumarins crude product;
(3) purification: add potassium hydroxide in the total coumarins crude extract that obtains, the limit edged stirs, and transferring pH is 7～8, filters, add hydrochloric acid in filtrate, the limit edged stirs, transfer pH be 2～3,3～5 ℃ cold preservation 12-16 hour, sucking filtration, discard filtrate, the yellow solid vacuum drying with obtaining namely gets total coumarins.
2. application according to claim 1 is characterized in that petroleum ether used in step (1) is 30～60 ℃ or 60～90 ℃ boiling range specifications, and residue is flung to petroleum ether.
3. application according to claim 1 is characterized in that in step (2), the ethanol concentration of volume percent is 70～95%, and every gram coarse powder adds 10mL ethanol or methanol.
4. application according to claim 3 is characterized in that using ethanol or methanol heating and refluxing extraction or supersound extraction 2～3 times, each 1～2 hour.
5. application according to claim 4 is characterized in that using 70% alcohol heating reflux to extract 3 times, each 2h.
6. application according to claim 1 is characterized in that the concentration of the middle potassium hydroxide of step (3) or hydrochloric acid is 1-2wt%.
7. application according to claim 1 is characterized in that in step (3) that the vacuum drying condition is under 60～70 ℃, 0.07～0.09MP pressure dry 4 hours.
8. application according to claim 1 is characterized in that using in step (1) defat with petroleum ether for using petroleum ether to carry out cable-styled defat.
9. application according to claim 1 is characterized in that in step (1), Semen Euphorbiae kind skin uses high speed disintegrator to be ground into 20～40 purpose coarse powder after removing impurity, then uses the cable-styled defat of petroleum ether colourless to petroleum ether extract.
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| ES2879098B2 (en) * | 2020-05-18 | 2022-10-14 | Univ Granada | Ethanolic extract of Euphorbia lathyris seeds, method for obtaining it, pharmaceutical composition containing it and its use as an antitumor agent |
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| 千金子种仁与种皮中总香豆素的含量测定;李英霞等;《陕西中医》;20080505;第29卷(第05期);605-606 * |
| 李英霞等.千金子种仁与种皮中总香豆素的含量测定.《陕西中医》.2008,第29卷(第05期),605-606. |
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