CN114028462A - Method for extracting phenylpropanoid components from Prunus mume flower - Google Patents
Method for extracting phenylpropanoid components from Prunus mume flower Download PDFInfo
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- CN114028462A CN114028462A CN202111422380.4A CN202111422380A CN114028462A CN 114028462 A CN114028462 A CN 114028462A CN 202111422380 A CN202111422380 A CN 202111422380A CN 114028462 A CN114028462 A CN 114028462A
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- prunus mume
- phenylpropanoid
- extraction
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/185—Magnoliopsida (dicotyledons)
- A61K36/73—Rosaceae (Rose family), e.g. strawberry, chokeberry, blackberry, pear or firethorn
- A61K36/736—Prunus, e.g. plum, cherry, peach, apricot or almond
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
- A61K2236/10—Preparation or pretreatment of starting material
- A61K2236/17—Preparation or pretreatment of starting material involving drying, e.g. sun-drying or wilting
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
- A61K2236/10—Preparation or pretreatment of starting material
- A61K2236/19—Preparation or pretreatment of starting material involving fermentation using yeast, bacteria or both; enzymatic treatment
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
- A61K2236/30—Extraction of the material
- A61K2236/33—Extraction of the material involving extraction with hydrophilic solvents, e.g. lower alcohols, esters or ketones
- A61K2236/333—Extraction of the material involving extraction with hydrophilic solvents, e.g. lower alcohols, esters or ketones using mixed solvents, e.g. 70% EtOH
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
- A61K2236/30—Extraction of the material
- A61K2236/39—Complex extraction schemes, e.g. fractionation or repeated extraction steps
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
- A61K2236/50—Methods involving additional extraction steps
- A61K2236/51—Concentration or drying of the extract, e.g. Lyophilisation, freeze-drying or spray-drying
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
- A61K2236/50—Methods involving additional extraction steps
- A61K2236/53—Liquid-solid separation, e.g. centrifugation, sedimentation or crystallization
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61K2236/50—Methods involving additional extraction steps
- A61K2236/55—Liquid-liquid separation; Phase separation
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- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Alternative & Traditional Medicine (AREA)
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- Mycology (AREA)
- Pharmacology & Pharmacy (AREA)
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- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines Containing Plant Substances (AREA)
Abstract
The invention discloses a method for extracting phenylpropanoid components from Prunus mume flower, which comprises the following steps: A. drying and crushing: freeze-drying and crushing the white plum blossom buds to obtain powder; B. extraction: mixing the powder with ethanol to obtain a mixed solution; adding pectinase into the mixed solution, and extracting with ultrasonic wave to obtain extract; centrifuging the extract in a centrifuge to obtain filtrate and residue; recovering ethanol, concentrating under reduced pressure, and freeze drying to obtain flos Pruni mume extract crude product; C. and (3) purification: dissolving and diluting the crude product of the prunus mume extract by adding purified water, dropwise adding hydrochloric acid, adjusting the pH to 3, loading the obtained product onto NKA-9 macroporous resin, sequentially eluting by using 20%, 30%, 40% and 50% ethanol, and performing reduced pressure concentration and freeze drying on the eluate to obtain the refined prunus mume extract. The method has the characteristics of effectively shortening the extraction time, improving the extraction efficiency and improving the extraction rate of effective components.
Description
Technical Field
The invention relates to a method for extracting components in prunus mume, in particular to a method for extracting phenylpropanoid components in prunus mume.
Background
The plum is originally produced in China, and has an application history of 7000-7500 years, an introduction cultivation history of more than 3000 years and a breeding and application history of more than 2000 years. The Prunus mume flower is derived from flower bud of Prunus mume (Sieb.) Sieb. et Zucc. of Rosaceae, and is named as "gang mu Shi" (compendium of compendium), also called "materia medica". In recent years, researchers at home and abroad have made relevant researches on chemical components and pharmacological actions of the plum blossom, and the components mainly comprise chemical components such as flavone, volatile oil, phenylpropanoids and the like, wherein the phenylpropanoids represented by chlorogenic acid and flavonoid components such as isoquercitrin, hyperin and the like have higher content in the plum blossom. The method adds chlorogenic acid as an index component of the plum blossom in the version of 2015 in Chinese pharmacopoeia, and further standardizes a plum blossom quality evaluation system. The medicinal white plum blossom is a dry flower bud, is recorded in compendium of materia Medica, and is mainly produced in Anhui, Zhejiang, Jiangsu and other places, wherein the chlorogenic acid content of the white plum blossom produced in Zhejiang is the highest.
The phenylpropanoids in the prunus mume mainly comprise chlorogenic acid, caffeic acid, caffeoylquinic acid, ferulic acid, feruloylquinic acid and isomers and derivatives thereof, and the like, wherein the chlorogenic acid is a component with higher content, has rich pharmacological activity, such as antibacterial, anti-inflammatory, antioxidant, melanin generation inhibition, ultraviolet resistance, radiation resistance and the like, and is a material basis of the prunus mume pharmacological activity.
However, the existing extraction method for phenylpropanoid components in prunus mume is less researched, and the problems of long extraction time, relatively low extraction efficiency and the like exist by adopting the traditional water extraction method and the traditional alcohol extraction method. In addition, because the phenylpropanoids mainly comprise chlorogenic acid and other substances, the chlorogenic acid is a heat-sensitive substance, and the decomposition of the chlorogenic acid can be caused by the relatively high temperature of the extraction time, so that the extraction rate of the effective ingredients is influenced. Therefore, the prior art has the problems of long extraction time, low extraction efficiency and easy decomposition of effective components.
Disclosure of Invention
The invention aims to provide a method for extracting phenylpropanoid components from prunus mume. The method has the characteristics of effectively shortening the extraction time, improving the extraction efficiency and improving the extraction rate of effective components.
The technical scheme of the invention is as follows: a method for extracting phenylpropanoid components from Prunus mume flower comprises the following steps:
A. drying and crushing: freeze-drying the white plum blossom buds, and crushing the freeze-dried white plum blossom buds by using a crusher to prepare sample powder;
B. extraction: mixing the sample powder with 60% ethanol to obtain a mixed solution; adding pectinase into the mixed solution, and extracting with ultrasonic wave to obtain extract; centrifuging the extract in a centrifuge to obtain filtrate and residue; repeating the steps on the residues to obtain secondary filtrate; mixing the secondary filtrate and the filtrate, recovering ethanol, concentrating under reduced pressure, and freeze drying to obtain flos Pruni mume extract crude product;
C. and (3) purification: dissolving the crude Prunus mume flower extract with purified water to obtain aqueous solution of the extract; dropwise adding hydrochloric acid into the aqueous extract solution to adjust the pH of the aqueous extract solution to 3, then loading the aqueous extract solution onto NKA-9 macroporous resin, sequentially using 20%, 30%, 40% and 50% ethanol as eluent to perform elution operation, combining all the eluents, and performing reduced pressure concentration and freeze drying treatment on the eluent to obtain the refined Prunus mume flower extract.
In the method for extracting phenylpropanoid components from Prunus mume, Prunus mume flower buds are produced in Zhejiang or other places, but have the same chlorogenic acid content.
In the method for extracting phenylpropanoid components from white plum blossom, white plum blossom buds are crushed and screened through a 40-mesh sieve, and then sample powder is obtained.
In the method for extracting phenylpropanoid components from Prunus mume, the feed-liquid ratio of the sample powder to ethanol is 1:14-17g/ml in the extraction process.
In the method for extracting phenylpropanoid components from Prunus mume flower, the addition amount of pectinase is 0.15-0.25% of the mixed solution.
In the method for extracting phenylpropanoid components from Prunus mume, when ultrasonic wave is used for extraction, the ultrasonic power is 55-60W and the ultrasonic frequency is 60 KHz; the extraction temperature is 50 deg.C, and the extraction time is 1 h.
In the method for extracting phenylpropanoid components from Prunus mume flower, the specific process of centrifugal filtration in the centrifuge is that the centrifuge performs centrifugal treatment at 7000r/min for 15 min.
In the method for extracting phenylpropanoid components from Prunus mume, the elution flow rate is 2.0-3.0BV/h and the elution volume is 4-5.5BV during the elution operation.
Compared with the prior art, the method organically combines the biological enzyme method and the ultrasonic extraction method, and the biological enzyme method has relatively good extraction effect, relatively low price and environmental protection; the ultrasonic extraction method has the advantages of short extraction time, relatively high extraction efficiency, difficult damage of extracted substances and the like. The two methods are combined together, so that the extraction time of 1-2h can be effectively shortened, the extraction efficiency of phenylpropanoid components can be improved (the extraction efficiency can be improved by 30-40%), and the extraction rate of chlorogenic acid can be effectively improved (the extraction rate of chlorogenic acid can be improved by 20-50%); macroporous resin is used for purification, the pH value of diluent is strictly controlled, the adsorption rate of the macroporous resin can be improved, ethanol with different concentrations is used as an eluent, chlorogenic acid substances and flavonoid substances in the crude extract of the prunus mume can be effectively separated, and phenylpropanoid substances such as chlorogenic acid and the like are directionally enriched. The invention effectively shortens the extraction time and improves the extraction rate of the phenylpropanoid active ingredients by strictly limiting the specific process parameters in each step and mutually matching each step and the process parameters. In conclusion, the method has the characteristics of effectively shortening the extraction time, improving the extraction efficiency and improving the extraction rate of effective components.
Drawings
FIG. 1 is a graph of B16 cell viability for different concentrations of Prunus mume flower extract.
Detailed Description
The invention is further illustrated by the following figures and examples, which are not to be construed as limiting the invention.
Example 1. A method for extracting phenylpropanoid components from Prunus mume flower comprises the following steps:
A. drying and crushing: freeze-drying the white plum blossom buds, and crushing the freeze-dried white plum blossom buds by using a crusher to prepare sample powder;
B. extraction: mixing the sample powder with 60% ethanol to obtain a mixed solution; adding pectinase into the mixed solution, and extracting with ultrasonic wave to obtain extract; centrifuging the extract in a centrifuge to obtain filtrate and residue; repeating the steps on the residues to obtain secondary filtrate; mixing the secondary filtrate and the filtrate, recovering ethanol, concentrating under reduced pressure, and freeze drying to obtain flos Pruni mume extract crude product;
C. and (3) purification: dissolving the crude Prunus mume flower extract with purified water to obtain aqueous solution of the extract; dropwise adding hydrochloric acid into the aqueous extract solution to adjust the pH of the aqueous extract solution to 3, then loading the aqueous extract solution onto NKA-9 macroporous resin, sequentially using 20%, 30%, 40% and 50% ethanol as eluent to perform elution operation, combining all the eluents, and performing reduced pressure concentration and freeze drying treatment on the eluent to obtain the refined Prunus mume flower extract.
The flos Pruni mume flower bud is produced in Zhejiang.
Crushing the white plum blossom buds, sieving by a 40-mesh sieve, and screening to obtain sample powder.
In the extraction process, the feed-liquid ratio of the sample powder to the ethanol is 1:14-17 g/ml.
The addition amount of pectase is 0.15-0.25% of the mixed solution.
When ultrasonic wave is used for extraction, the ultrasonic power is 55-60W and the ultrasonic frequency is 60 KHz; the extraction temperature is 50 deg.C, and the extraction time is 1 h.
The specific process of centrifugal filtration in the centrifuge is that the centrifuge carries out centrifugal treatment for 15min at the speed of 7000 r/min.
During the elution operation, the elution flow rate is 2.0-3.0BV/h, and the elution volume is 4-5.5 BV.
In the step B, the repeated operation of the residues is as follows: mixing the residue with 60% ethanol to obtain a mixed solution; adding pectinase into the mixed solution, and extracting with ultrasonic wave to obtain extract; and (4) placing the extract in a centrifuge for centrifugal filtration to respectively obtain secondary filtrate.
Example 2. A method for extracting phenylpropanoid components from Prunus mume flower comprises the following steps:
A. drying and crushing: freeze-drying the white plum blossom buds, and crushing the freeze-dried white plum blossom buds by using a crusher to prepare sample powder;
B. extraction: mixing the sample powder with 60% ethanol to obtain a mixed solution; adding pectinase into the mixed solution, and extracting with ultrasonic wave to obtain extract; centrifuging the extract in a centrifuge to obtain filtrate and residue; repeating the above operation for 2 times to obtain secondary filtrate; mixing the secondary filtrate and the filtrate, recovering ethanol, concentrating under reduced pressure, and freeze drying to obtain flos Pruni mume extract crude product;
C. and (3) purification: adding purified water into the crude product of the white plum blossom extract for dissolving and diluting to obtain a diluent; dropwise adding hydrochloric acid into the diluent, adjusting the pH of the diluent to 3, then loading the diluent on a pretreated NKA-9 macroporous resin, sequentially using 20%, 30%, 40% and 50% ethanol as eluent to perform elution operation, combining all the eluents, and performing reduced pressure concentration and freeze drying on the eluents to obtain the refined white plum blossom extract.
Chlorogenic acid is phenolic acid formed by condensation of quinic acid and caffeic acid, and consists of hydroxyl and carboxyl, the NKA-9 macroporous resin has a special spatial structure, is matched with chlorogenic acid substances to be better adsorbed, and has a better enrichment effect on chlorogenic acid.
The pH value plays a crucial role in the adsorption and purification effect of the macroporous resin, because the phenolic hydroxyl group of chlorogenic acid substances in the prunus mume increases the adsorption effect by virtue of van der Waals force under an acidic condition, but then the adsorption rate of the macroporous resin is gradually reduced along with the increase of the pH value, the chlorogenic acid undergoes acetification reaction, the adsorption rate is reduced, and therefore the pH value is selected to be the optimal pH value of the upper column liquid when the pH value is 3.
The desorption rate of the phenylpropanoid substances in the prunus mume increases along with the increase of the concentration of the ethanol eluent, when the concentration of the eluent is 50%, the desorption rate of the chlorogenic acid substances reaches the maximum value, and when the concentration of the eluent is more than 50%, the desorption rate is gradually reduced, because when the concentration of the ethanol is too high, impurities with small residual polarity are easy to elute, and when the concentration of the ethanol is too low, the elution is not thorough, and the cost is increased, therefore, the cost performance is excellent when the concentration of the ethanol eluent is selected to be 50%.
The flos Pruni mume flower bud is produced in Zhejiang. The content of the plum blossom phenylpropanoids produced in Zhejiang is higher than that of the plum blossom produced in other producing areas.
Crushing the white plum blossom buds, sieving by a 40-mesh sieve, and screening to obtain sample powder.
During extraction, the feed-liquid ratio of the sample powder to the ethanol is 1:16 g/ml.
The addition amount of pectinase is 0.20%.
When ultrasonic waves are used for extraction, the ultrasonic power is 57W and the ultrasonic frequency is 60 KHz; the extraction temperature is 50 deg.C, and the extraction time is 1 h.
The specific process of centrifugal filtration in the centrifuge is that the centrifuge carries out centrifugal treatment for 15min at the speed of 7000 r/min.
During the elution operation, the elution flow rate is 2.0-3.0BV/h, and the elution volume is 5.08 BV.
The contents of phenylpropanoid representative components (chlorogenic acid, caffeic acid, monocaffeylquinic acid, isoferulic acid, feruloylquinic acid) in the white plum extract refined by the method of example 2 were measured by HPLC.
The HPLC is Ultimate 300, Seimer Feishell science, using Shimpack VP-ODS column (250 mm. times.4.6 mm, 5 μm); mobile phase 0.1% aqueous formic acid (a) -0.1% acetonitrile formic acid (B), gradient elution: 0-15min, 12% -15% B; 15-20min, 15% -17% B; 20-40min, 17% B; 40-41min, 17% -12% B; 41-45min, 12% B; flow rate 1.0 mL/min-1(ii) a The detection wavelength is 355 nm; the column temperature is 40 ℃; the sample size was 5. mu.L. The results are shown in Table 1.
TABLE 1
| Composition (I) | Content (%) |
| Chlorogenic acid | 18.60-23.00 |
| Caffeic acid | 11.50-16.00 |
| Monocaffeylquinic acid | 13.60-24.40 |
| Isoferulic acid | 1.30-3.54 |
| Feruloylquinic acid | 1.93-2.78 |
Assay of cellular melanoidins
(1) B16 culture of melanoma cells: selecting B16 cells in logarithmic growth phase, digesting with 0.25% trypsin, subculturing with DMEM medium containing 10% fetal calf serum, placing in incubator at 37 deg.C and 5% CO2Culturing is carried out in the environment.
(2) B16 cell viability assay the viability of B16 cells was determined by the CCK-8 method. Cells of log phase B16 were harvested, plated in 96-well plates and cultured overnight. Adding aqueous solution of flos Pruni mume extract with concentration of 10mg/mL, 20mg/mL, 30mg/mL, 40mg/mL, 50mg/mL, and 60mg/mL respectively. The untreated group was used as a control group of cells, each group was provided with 3 multiple wells, and placed in an incubator at 37 ℃ with 5% CO2Culturing for 48 hours in the environment, adding CCK-8 after the culture is finished, continuing to incubate for 1 hour, and measuring the absorbance value of each hole by using an enzyme-labeling instrument at the wavelength of 450 nm.
Cell viability ═ 100% (assay well OD value-blank OD value)/(cell control OD value-blank OD value) × 100%
(3) Determination of melanin content: the cells of log phase B16 were seeded in 24-well plates and cultured for 6 hours. Adding 10mg/mL arbutin and 1mg/mL, 30mg/mL, 50mg/mL aqueous solution of flos Pruni mume extract. The untreated group was used as a cell control group. After 36 hours of incubation, the medium was discarded, washed 1 time with PBS, cells were collected by trypsinization, and washed 1 time with PBS. 1M NaOH (10% DMSO) was added, the mixture was placed in a 80 ℃ water bath for 30 minutes, the supernatant was added to a 96-well plate, and the absorbance value was read at 475nm with a microplate reader.
Melanin content change ═ (assay well OD value-blank OD value)/(cell control OD value-blank OD value)
The concentration of the safety work of the white plum blossom extract is firstly measured by a CCK-8 method. The results are shown in FIG. 1, where the survival rate of B16 cells was close to 100% at a concentration of 50mg/mL or less, the concentration was safe, and no cytotoxicity was observed. Note: p <0.05, p <0.01, p <0.001 in fig. 1.
The effect of each concentration sample on the amount of B16 melanin synthesized is shown in table 2, and prunus mume flower extract was effective in inhibiting melanin production by melanocytes.
TABLE 2 Effect of various concentration samples on the amount of B16 melanin synthesized
Note: variance homogeneity test F1.804, variance, VS blank p <0.05, p <0.01, p < 0.001.
Claims (8)
1. A method for extracting phenylpropanoid components from Prunus mume flower is characterized by comprising the following steps:
A. drying and crushing: freeze-drying the white plum blossom buds, and crushing the freeze-dried white plum blossom buds by using a crusher to prepare sample powder;
B. extraction: mixing the sample powder with 60% ethanol to obtain a mixed solution; adding pectinase into the mixed solution, and extracting with ultrasonic wave to obtain extract; centrifuging the extract in a centrifuge to obtain filtrate and residue; repeating the steps on the residues to obtain secondary filtrate; mixing the secondary filtrate and the filtrate, recovering ethanol, concentrating under reduced pressure, and freeze drying to obtain flos Pruni mume extract crude product;
C. and (3) purification: dissolving the crude Prunus mume flower extract with purified water to obtain aqueous solution of the extract; dropwise adding hydrochloric acid into the aqueous extract solution to adjust the pH of the aqueous extract solution to 3, then loading the aqueous extract solution onto NKA-9 macroporous resin, sequentially using 20%, 30%, 40% and 50% ethanol as eluent to perform elution operation, combining all the eluents, and performing reduced pressure concentration and freeze drying treatment on the eluent to obtain the refined Prunus mume flower extract.
2. The method for extracting phenylpropanoid component from Prunus mume as claimed in claim 1, wherein: the flos Pruni mume flower bud is produced in Zhejiang.
3. The method for extracting phenylpropanoid component from Prunus mume as claimed in claim 1, wherein: crushing the white plum blossom buds, sieving by a 40-mesh sieve, and screening to obtain sample powder.
4. The method for extracting phenylpropanoid component from Prunus mume as claimed in claim 1, wherein: in the extraction process, the feed-liquid ratio of the sample powder to the ethanol is 1:14-17 g/ml.
5. The method for extracting phenylpropanoid component from Prunus mume as claimed in claim 1, wherein: the addition amount of pectase is 0.15-0.25% of the mixed solution.
6. The method for extracting phenylpropanoid component from Prunus mume as claimed in claim 1, wherein: when ultrasonic wave is used for extraction, the ultrasonic power is 55-60W and the ultrasonic frequency is 60 KHz; the extraction temperature is 50 deg.C, and the extraction time is 1 h.
7. The method for extracting phenylpropanoid component from Prunus mume as claimed in claim 1, wherein: the specific process of centrifugal filtration in the centrifuge is that the centrifuge carries out centrifugal treatment for 15min at the speed of 7000 r/min.
8. The method for extracting phenylpropanoid component from Prunus mume as claimed in claim 1, wherein: during the elution operation, the elution flow rate is 2.0-3.0BV/h, and the elution volume is 4-5.5 BV.
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| SEIKOU NAKAMURA等: "Acylated sucroses and acylated quinic acids analogs from the flower buds of Prunus mume and their inhibitory effect on melanogenesis", 《PHYTOCHEMISTRY》 * |
| 严辉等: "梅花化学成分与药理活性研究进展", 《中草药》 * |
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