CN115785114A - Method for extracting ellagic acid - Google Patents
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- CN115785114A CN115785114A CN202211534496.1A CN202211534496A CN115785114A CN 115785114 A CN115785114 A CN 115785114A CN 202211534496 A CN202211534496 A CN 202211534496A CN 115785114 A CN115785114 A CN 115785114A
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- ellagic acid
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- AFSDNFLWKVMVRB-UHFFFAOYSA-N Ellagic acid Chemical compound OC1=C(O)C(OC2=O)=C3C4=C2C=C(O)C(O)=C4OC(=O)C3=C1 AFSDNFLWKVMVRB-UHFFFAOYSA-N 0.000 title claims abstract description 72
- ATJXMQHAMYVHRX-CPCISQLKSA-N Ellagic acid Natural products OC1=C(O)[C@H]2OC(=O)c3cc(O)c(O)c4OC(=O)C(=C1)[C@H]2c34 ATJXMQHAMYVHRX-CPCISQLKSA-N 0.000 title claims abstract description 72
- 229920002079 Ellagic acid Polymers 0.000 title claims abstract description 72
- 229960002852 ellagic acid Drugs 0.000 title claims abstract description 72
- 235000004132 ellagic acid Nutrition 0.000 title claims abstract description 72
- FAARLWTXUUQFSN-UHFFFAOYSA-N methylellagic acid Natural products O1C(=O)C2=CC(O)=C(O)C3=C2C2=C1C(OC)=C(O)C=C2C(=O)O3 FAARLWTXUUQFSN-UHFFFAOYSA-N 0.000 title claims abstract description 72
- 238000000034 method Methods 0.000 title claims abstract description 27
- 238000001035 drying Methods 0.000 claims abstract description 39
- 238000000605 extraction Methods 0.000 claims abstract description 22
- 240000007651 Rubus glaucus Species 0.000 claims abstract description 17
- 235000011034 Rubus glaucus Nutrition 0.000 claims abstract description 16
- 235000009122 Rubus idaeus Nutrition 0.000 claims abstract description 16
- 238000009736 wetting Methods 0.000 claims abstract description 11
- 239000002994 raw material Substances 0.000 claims abstract description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- 238000010992 reflux Methods 0.000 claims description 10
- 238000010438 heat treatment Methods 0.000 claims description 6
- 238000009210 therapy by ultrasound Methods 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 abstract description 6
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- 235000004789 Rosa xanthina Nutrition 0.000 abstract description 2
- 241000220222 Rosaceae Species 0.000 abstract description 2
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- 238000004458 analytical method Methods 0.000 description 10
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- 244000235659 Rubus idaeus Species 0.000 description 4
- HHEAADYXPMHMCT-UHFFFAOYSA-N dpph Chemical compound [O-][N+](=O)C1=CC([N+](=O)[O-])=CC([N+]([O-])=O)=C1[N]N(C=1C=CC=CC=1)C1=CC=CC=C1 HHEAADYXPMHMCT-UHFFFAOYSA-N 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000011002 quantification Methods 0.000 description 4
- 235000021013 raspberries Nutrition 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 238000000540 analysis of variance Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 238000001134 F-test Methods 0.000 description 2
- 241000219991 Lythraceae Species 0.000 description 2
- 235000014360 Punica granatum Nutrition 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 238000007599 discharging Methods 0.000 description 2
- 238000000855 fermentation Methods 0.000 description 2
- 230000004151 fermentation Effects 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000004704 ultra performance liquid chromatography Methods 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
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- 102000004190 Enzymes Human genes 0.000 description 1
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- 206010061218 Inflammation Diseases 0.000 description 1
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- 238000002835 absorbance Methods 0.000 description 1
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- 235000013399 edible fruits Nutrition 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000556 factor analysis Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000003306 harvesting Methods 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
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- 230000014759 maintenance of location Effects 0.000 description 1
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- 235000020824 obesity Nutrition 0.000 description 1
- 238000000643 oven drying Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 150000008442 polyphenolic compounds Chemical class 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- XHFLOLLMZOTPSM-UHFFFAOYSA-M sodium;hydrogen carbonate;hydrate Chemical compound [OH-].[Na+].OC(O)=O XHFLOLLMZOTPSM-UHFFFAOYSA-M 0.000 description 1
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The application provides an ellagic acid extraction method, and belongs to the technical field of preparation of medicinal preparations from Rosaceae. The method comprises the steps of taking raspberry as a raw material, fully piling up and wetting, placing the raspberry in an oven to be free of moisture discharge and rewetting, taking out, drying and extracting to obtain the ellagic acid. The extraction method has the advantages of high ellagic acid content, controllable conditions in production and processing, and easy mass operation.
Description
Technical Field
The application relates to an ellagic acid extraction method, and belongs to the technical field of preparation of medicinal preparations from Rosaceae.
Background
Ellagic acid is a natural polyphenol substance, has the effects of resisting oxidation, cancer, HIV, bacteria, inflammation and virus, preventing obesity and diabetes and the like, has wide application prospect, is prepared and purified by taking pomegranate peel, gallnut and the like as raw materials at present, and is mainly obtained by a solid fermentation method, a liquid fermentation method and an enzyme conversion method, but has different advantages and disadvantages of various production processes. Such as: the pomegranate rind is mostly obtained in an alkali-dissolving and acid-precipitating manner, so that not only are regional differences existing, but also the highest content difference can reach about 8%, and the quality loss also exists; the gallnut is used for obtaining the ellagic acid in a leaching way, and has the defect of low efficiency.
In recent years, along with the development of extraction technology, the acquisition of ellagic acid from rosaceous raw materials enters the visual field of researchers, for example, CN 109078063A, and the steps of harvesting, de-enzyming, drying, steam dampening, fermenting, secondary drying and the like are carried out on raspberries, so that the content of ellagic acid in raspberries is increased, and the problem that the content of ellagic acid of raspberries generally does not reach the standard is solved, but the problem that parameters are not matched with actual operation exists. CN114605247A uses raspberry as raw material, uses sodium bicarbonate water solution as extraction reagent, and combines with heating treatment to realize improvement of extraction efficiency and reduction of extraction reagent cost, but is not suitable for raspberry.
Disclosure of Invention
In view of the above, the application provides an ellagic acid extraction method, which takes raspberries as raw materials, realizes the extraction of ellagic acid by means of mechanical treatment, a drying mode and the control of rewetting time, and has the advantages of solving the problem that the content of ellagic acid does not reach the standard, being practical, easy to produce and operate in a large scale, and being simple and easy to implement.
Specifically, the present application is realized by:
an extraction method of ellagic acid comprises treating Rubi fructus as raw material:
(1) Rewetting: fully wetting the raspberry sample, putting the sample in an oven, and rewetting for 30-60h at 40-60 ℃;
(2) And (3) drying: drying the rewetted sample to a moisture level of no more than 12%;
(3) Extraction: and extracting the dried sample.
The scheme realizes the extraction of the ellagic acid by means of rewetting and drying, and the extraction mode has the characteristics of easy mass production and operation and simple and easy implementation; the obtained ellagic acid has high content.
Further, as an advantage:
in the step (1), the full wetting adopts water wetting, and the water adding amount is 20-25% of the mass of the sample. More preferably, after being wetted, the mixture is piled up at room temperature to absorb moisture for 2 to 3 hours and then transferred to an oven for rewetting.
In the step (1), the rewetting temperature is 40 ℃, and the rewetting time is controlled to be 55-60h; or the rewetting temperature is 50 ℃, and the rewetting time is controlled to be 50-55h; or the rewetting temperature is 60 ℃, and the rewetting time is controlled to be 45-50h. More preferably, the rewetting parameter is 60 ℃ for 45h.
In the step (2), the drying mode adopts drying in the shade, sun drying or baking. More preferably, in the drying mode, the temperature is 20-25 ℃, and the time is based on the condition that the medicinal materials are dried until the water content is not more than 12%; drying at 30-35 deg.C for no more than 12% water; in the drying mode, the temperature is 60 ℃, and the time is based on the drying of the medicinal materials until the water content is not more than 12%.
In the step (3), the extraction parameters are preferably set as: adding 70% methanol, heating and refluxing for 1-2h, and performing ultrasonic treatment for 10-20min during refluxing process. More preferably, 70% methanol is added to be heated and refluxed for 1h, and ultrasonic treatment is carried out for 20min during the refluxing process.
According to the scheme, by means of a mode of wetting first and then moistening, the efficient extraction of the ellagic acid in the raspberry is realized, the obtained ellagic acid preparation has a good antioxidant effect, and the ellagic acid preparation is used for the development of daily chemicals and endows the daily chemicals with antioxidant effect.
Detailed Description
Example 1
In this example, the process of ellagic acid extraction was as follows:
(1) Wetting: taking 1000g of raspberry sample, adding into 200ml of purified water (the water amount is 20 percent), fully moistening, and stacking at room temperature for 3h.
(2) Rewetting: and (3) carrying out non-moisture-discharging rewetting (namely, not discharging evaporated moisture) on the sample after moisture absorption in an oven: the temperature is set to 55 ℃, and the rewetting treatment is carried out for 45h.
(3) And (3) drying: the rewetted sample was dried in the shade at room temperature (about 25 ℃ C.).
(4) Extraction: when the water content is detected to be 10%, transferring the sample into a reflux heating device, adding 50ml of 70% methanol to enable the sample to be soaked by the methanol for at least 1cm, heating the sample in a water bath until the sample is in a boiling state, refluxing the sample for 1h, wherein the ultrasonic power is 240w in the refluxing process, and the treatment time is 10min. Extracting repeatedly for 2-3 times, and collecting all condensate.
(4) And (3) detection: the content of the ellagic acid is determined by adopting an ultra-performance liquid chromatography (UPLC) method, and the test conditions are as follows: the column temperature is 35 ℃; the flow rate is 0.4mL/min; the sample injection amount is 5.0 mu L; the detection wavelength is 254nm; the mobile phase was 0.1% A formic acid solution-B acetonitrile solution (0-2min, 94% → 94% A2-3min, 94% → 84% A3-8min, 84% → 80% A8-10min, 80% → 94% A), giving an ellagic acid content of 0.653%.
Example 2
This example is the same as the arrangement of example 1, except that: in the step (3), the raspberry sample is dried at 60 ℃ until the water content is 10%, and the ellagic acid content is 0.433%.
Example 3
This example is the same as the arrangement of example 1, except that: in the step (3), the raspberry sample is dried in the sun (about 30 ℃) until the water content is 10%, and the content of ellagic acid is 0.588%.
Comparative example 1 with examples 2, 3: high content of ellagic acid is more easily obtained by drying in the shade.
Meanwhile, we also carried out the significance and effect quantitative analysis of the drying mode, as shown in tables 1 and 2.
Table 1: significance analysis of drying regimes
As can be seen from table 1: the average value of drying in the shade/sun/oven dry is: 0.501/0.347/0.363; the analysis of variance results, with a P value of 0.000 x ≦ 0.05, are significant, indicating: the different drying modes have obvious difference in the content of the ellagic acid, and the content of the ellagic acid obtained by extraction is enhanced: drying in the shade in a cool and ventilated place > natural drying > oven drying.
Quantitative effect analysis was performed on three groups (24 specimens per group) of dried samples, and the results are shown in table 2.
Table 2: quantitative analysis of the Effect of the Dry mode
As can be seen from table 2: the Eta formula (. Eta.2 value) based on ellagic acid content was 0.328, indicating that the data differed 32.8% from the differences between the different groups; the Cohen's f value was 0.698, indicating that the effect quantification of the data differed to a large degree, which is also evidenced by: the different drying modes have significant difference in ellagic acid content, the drying modes have a large influence on the ellagic acid content, and the experimental results in table 1 above can be combined to determine that: drying in the shade in a cool and ventilated place is more suitable for the drying treatment of the ellagic acid.
Example 4
This example is the same as the arrangement of example 1, except that: before wetting, the pot-covered fruit samples were subjected to mechanical rolling to remove the stalks. The ellagic acid content obtained was 0.407%.
The mechanical treatment comprises the following specific operations: mechanically rolling to remove stalks for a period of time determined by the amount of the medicinal materials.
Meaning of stemming and rolling hair: mechanical rolling is carried out to remove stalks, the time is determined according to the quantity of the medicinal materials, and the retention of the skin and the hair is poor.
Meaning of non-stemmed rolled hair: the mechanical rolling is not carried out to remove the stalks, and the skin and the hair are well kept.
Comparative examples 1 and 4: mechanical rolling for removing stalks can not improve the content of ellagic acid, and theoretical support is provided for the whole raspberry plant to be used as a medicine.
Meanwhile, the significance and effect quantitative analysis of mechanical treatment is also carried out.
Table 3: significance analysis of ellagic acid content by mechanical treatment
As can be seen from table 3: the mean values of the de-stemmed and un-stemmed rolled hairs are: 0.369/0.439; the analysis of variance result P value is 0.013 x ≦ 0.05, the result is significant, and shows that: different mechanical treatments have obvious difference in ellagic acid content, and the ellagic acid extracted by the method is more uniform in quality and more stable in content under the condition of the same sample amount and without the treatment of stemmed and rolled bristles (namely, example 1).
The results of the intra-group analysis were shown in Table 7 for 36 sample sizes.
Table 4: quantitative analysis result of mechanized effect
The results of the quantitative analysis of the effects of table 4 are again corroborated: the Eta square (η 2 value) was 0.084 based on ellagic acid content, indicating that the difference in data was 8.4% from the difference between the different groups; the Cohen's f value is 0.303, which shows that the difference degree of the effect quantification of the data is medium difference, which shows that the difference between the batches of the mechanized treatment is small, the method plays a negative role in improving the ellagic acid content, and the non-mechanized treatment is better.
Example 5
This example is the same as the arrangement of example 1, except that: the rewetting temperatures and rewetting times of 55 ℃ are shown in Table 5, respectively.
Table 5: ellagic acid content comparison table obtained by different rewetting time
Serial number | Rewetting time, h | Ellagic acid content% |
1-1 | 30 | 0.415 |
1-2 | 40 | 0.459 |
1-3 | 50 | 0.633 |
1-4 | 60 | 0.628 |
。
As can be seen by comparing example 1 with table 5: the content of ellagic acid can reach above 0.6% when the rewetting time is controlled at 45-50h at 55 deg.C.
Meanwhile, the applicant also carries out rewetting treatment at 40 ℃ and 50 ℃, and the result shows that: the content of ellagic acid is more than 0.6%, the optimal rewetting time at 40 deg.C is 55-60h, and the optimal rewetting time at 50 deg.C is 50-55h.
Meanwhile, we also performed analysis of significance and effect quantification of rewetting time, and the results are shown in tables 6 and 7.
Table 6: significance analysis of rewetting time on ellagic acid content
As can be seen from table 6: the average rewetting time of 30h/40h/45h/50h was 0.314 x/0.354 x/0.473 x; analysis of variance results P values were 0.000 x ≦ 0.05, with significant results. Description of the drawings: the different rewetting times have obvious difference in the content of ellagic acid, and the content of ellagic acid is 0.4% at 30 h; the ellagic acid content is 0.407% at 40 h; the ellagic acid content is 0.601% at 45 h; the ellagic acid content is 0.434% at 50 h; the best effect is obtained after 45 hours.
Table 7: quantitative analysis result of rewetting time effect
Table 7 shows the results of quantitative analysis of effects: the Eta formula (. Eta.2 value) was 0.345 based on ellagic acid content, indicating that 34.5% of the data difference was derived from the difference between the different groups. The Cohen's f value is 0.726, indicating that the effect quantification of the data differs to a large extent, which also confirms that: the different rewetting times have obvious difference in the content of the ellagic acid, and the rewetting time has great influence on the content of the ellagic acid.
In summary, it can be seen that: the positive effect on ellagic acid content was the rewetting time and drying pattern, on which a two-factor experiment was performed, with the results shown in table 8.
Table 8: two-factor analysis of variance results
The main effect, if significant, can be further analyzed in the post multiple analysis results, as can be seen from table 5:
for the variable intercept, it can be obtained from the analysis of the results of the F-test that the significance P value is 0.000 x, the significance is shown horizontally, there is a significant effect on the ellagic acid content, there is a main effect.
For the variable rewet time, it can be obtained from the analysis of the results of the F-test that the significance P value is 0.000 x, the significance is shown horizontally, there is a significant effect on the ellagic acid content, there is a main effect.
For the variant drying mode, it can be obtained from the analysis of the results of the F test that the significance P value is 0.000 x, the significance is shown horizontally, there is a significant effect on the ellagic acid content, there is a main effect.
Therefore, the method comprises the following steps: by independently adopting the drying and rewetting treatment modes, a certain ellagic acid extraction amount effect can be obtained, but the effective extraction of ellagic acid can be realized only by the scheme of the application with both drying and rewetting.
Example 6
The ellagic acid prepared in example 1 was taken and subjected to an antioxidant test. The procedure and results were as follows:
1. to a 96-well plate, 10. Mu.L of ellagic acid extract was added.
2. A0.2 mmol/L DPPH solution in 100. Mu.L kit (DPPH kit) was added.
3. After mixing, the mixture is reacted for 20min in a dark place at room temperature, and then the absorbance is measured by an enzyme-linked immunosorbent assay at 517nm, and the calculation is carried out according to a standard curve in a DPPH kit.
Antioxidant effect: the DPPH clearance rate is 58.83 percent, which shows that the prepared ellagic acid has good antioxidant effect.
Claims (10)
1. The method for extracting the ellagic acid is characterized in that raspberry is used as a raw material to be treated as follows:
(1) Rewetting: fully wetting the raspberry sample, putting the raspberry sample in an oven, and rewetting for 30-60 hours at 40-60 ℃;
(2) And (3) drying: drying the raspberry sample after the rewetting until the water content is less than or equal to 12%;
(3) Extraction: and extracting the rewetted sample.
2. The method for extracting ellagic acid according to claim 1, wherein: in the step (1), the full wetting adopts water wetting, and the water adding amount is 20-25% of the mass of the sample.
3. The method for extracting ellagic acid according to claim 1, wherein: and piling up the wetted raspberry sample at room temperature, absorbing moisture for 2-3h, and transferring the raspberry sample into an oven.
4. The method for extracting ellagic acid according to claim 1, wherein: in the step (1), the rewetting temperature is 40 ℃, and the rewetting time is controlled to be 55-60h; or the rewetting temperature is 50 ℃, and the rewetting time is controlled to be 50-55h; or the rewetting temperature is 60 ℃, and the rewetting time is controlled to be 45-50h.
5. The method for extracting ellagic acid according to claim 1, wherein: in the step (2), the drying mode adopts drying in the shade, sun drying or baking.
6. The method for extracting ellagic acid according to claim 5, wherein: in the drying mode, the temperature is 55-60 ℃.
7. The method for extracting ellagic acid according to claim 5, wherein: in the drying mode, the temperature is 20-25 ℃.
8. The method for extracting ellagic acid according to claim 5, wherein: in the sun-drying mode, the temperature is 30-35 ℃.
9. The method for extracting ellagic acid according to claim 1, wherein: in the step (3), the extraction parameters are set as: adding 70% methanol, heating and refluxing for 1-2h, and performing ultrasonic treatment for 10-20min during refluxing process.
10. The method for extracting ellagic acid according to claim 1, wherein: fully wetting a raspberry sample, rewetting for 45h at 55 ℃, drying in the shade at 20-25 ℃ until the water content is less than or equal to 12%, finally adding 70% methanol, heating and refluxing for 1h, and performing ultrasonic treatment for 10min in the refluxing process to obtain the finished ellagic acid.
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Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR20170135744A (en) * | 2016-05-31 | 2017-12-08 | (주)에스.앤.디 | Extraction method of Rasberry extract containing ellagic acid and isolation method of ellagic acid |
CN109078063A (en) * | 2018-07-12 | 2018-12-25 | 浙江大成药业有限公司 | A kind of processing method improving ellagic acid content in raspberry |
CN110772550A (en) * | 2019-12-06 | 2020-02-11 | 辽宁中医药大学 | Method for preparing ellagic acid from scalded myrobalan meat and application |
CN113773332A (en) * | 2021-09-23 | 2021-12-10 | 陕西中医药大学 | Method for extracting ellagic acid from blue brave by using ultrasonic-assisted deep eutectic solvent |
CN114605427A (en) * | 2022-03-25 | 2022-06-10 | 大连理工大学盘锦产业技术研究院 | Method for extracting and preparing raspberry ellagic acid |
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- 2022-12-02 CN CN202211534496.1A patent/CN115785114A/en active Pending
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR20170135744A (en) * | 2016-05-31 | 2017-12-08 | (주)에스.앤.디 | Extraction method of Rasberry extract containing ellagic acid and isolation method of ellagic acid |
CN109078063A (en) * | 2018-07-12 | 2018-12-25 | 浙江大成药业有限公司 | A kind of processing method improving ellagic acid content in raspberry |
CN110772550A (en) * | 2019-12-06 | 2020-02-11 | 辽宁中医药大学 | Method for preparing ellagic acid from scalded myrobalan meat and application |
CN113773332A (en) * | 2021-09-23 | 2021-12-10 | 陕西中医药大学 | Method for extracting ellagic acid from blue brave by using ultrasonic-assisted deep eutectic solvent |
CN114605427A (en) * | 2022-03-25 | 2022-06-10 | 大连理工大学盘锦产业技术研究院 | Method for extracting and preparing raspberry ellagic acid |
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