CN112500442A - Method for extracting raspberry glycoside by using functional polymer resin - Google Patents

Method for extracting raspberry glycoside by using functional polymer resin Download PDF

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Publication number
CN112500442A
CN112500442A CN202011480966.1A CN202011480966A CN112500442A CN 112500442 A CN112500442 A CN 112500442A CN 202011480966 A CN202011480966 A CN 202011480966A CN 112500442 A CN112500442 A CN 112500442A
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raspberry glycoside
functional polymer
raspberry
polymer resin
chromatographic column
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CN202011480966.1A
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仲玉
任连兵
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Nanjing Genshan Biotechnology Co ltd
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Nanjing Genshan Biotechnology Co ltd
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/20Carbocyclic rings
    • C07H15/203Monocyclic carbocyclic rings other than cyclohexane rings; Bicyclic carbocyclic ring systems
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H1/00Processes for the preparation of sugar derivatives
    • C07H1/06Separation; Purification

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Biochemistry (AREA)
  • Biotechnology (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Saccharide Compounds (AREA)

Abstract

The invention discloses a method for extracting raspberry glycoside by using functional polymer resin, which comprises the following steps: loading the chromatographic column, washing, preparing raspberry glycoside solution, loading, balancing, eluting, and concentrating to obtain the desired raspberry glycoside. According to the method, the functional polymer resin is used as a filler, the deionized water is used for sampling, and the pure water is used for eluting, so that the purity of the raspberry glycoside can be effectively improved, the method has the characteristics of high efficiency and low cost, and meanwhile, the extraction method avoids using a large amount of ethanol recrystallization liquid, is green and environment-friendly, and is easy to realize industrialization.

Description

Method for extracting raspberry glycoside by using functional polymer resin
Technical Field
The invention relates to the field of natural chemistry, in particular to a method for extracting raspberry glycoside by using functional polymer resin.
Background
The raspberry is a plant of rubus of Rosaceae, is a deciduous shrub with wide growth, and generally grows in mountain forests, wetlands and bush shrubs. Raspberry contains abundant amino acids, a large amount of superoxide dismutase, enzyme free radical scavenger, vitamin E, ellagic acid and raspberry glycoside. Vitamin E has anti-aging effect, ellagic acid has anticancer effect, and raspberry glycoside can be used as novel whitening conditioner, has effect in effectively inhibiting tyrosinase, and inhibiting melanin formation, and is effective nitrogen monoxide scavenger.
At present, the main method for extracting the raspberry glycosides is to extract the high-purity raspberry glycosides from raspberry crude extracts by a recrystallization method. Chinese patent publication No. CN107417696A provides a method for extracting raspberry glycosides and ellagic acid from fresh raspberry fruits, which comprises subjecting fresh raspberry fruits to water extraction, alcohol extraction, macroporous resin adsorption, fractional elution, and concentration crystallization to obtain pure raspberry glycosides and ellagic acid. Although the method is simple to operate and improves the yield of the raspberry glycoside and the ellagic acid, a large amount of organic solvent ethanol is required to be used in the process, concentration is required before recrystallization, a large amount of organic waste liquid is necessarily generated, the recrystallization process is required to be carried out for multiple times for obtaining the high-purity raspberry glycoside, the process is complicated, the energy consumption is high, and the industrial production is not facilitated.
Disclosure of Invention
Therefore, the technical problem to be solved by the invention is to overcome the defects that a large amount of organic solvent is needed and the process is complicated in the prior art for extracting the raspberry glycoside, so that the method for extracting the raspberry glycoside by using the functional polymer resin is provided, and the extraction efficiency of the raspberry glycoside is improved by a simple and environment-friendly extraction process.
Therefore, the invention provides a method for extracting raspberry glycoside by using functional polymer resin, which comprises the following steps:
(1) column packing and washing of a chromatographic column: dispersing functional polymer resin in water to form slurry, transferring the slurry to a chromatographic column, washing and compacting a chromatographic column bed by deionized water, and soaking until effluent liquid is free from peculiar smell;
(2) preparing a raspberry glycoside solution: taking the crude product of the raspberry glycoside and diluting the crude product with ultrapure water to prepare a raspberry glycoside solution;
(3) loading: continuously flowing the raspberry glycoside solution obtained in the step (2) through a chromatographic column;
(4) balancing: after the sample loading is finished, washing the chromatographic column by using ultrasonic water;
(5) and (3) elution: after the chromatographic column is balanced, taking deionized water as an eluent, separately collecting effluent liquid, and detecting the purity; combining the collected liquid with qualified purity to obtain a collected liquid;
(6) concentration: and concentrating the collected liquid, and drying to obtain the needed raspberry glycoside.
Preferably, the functional polymer resin is polystyrene microsphere resin.
Preferably, the preparation of the polystyrene microsphere resin comprises the following steps:
adding polystyrene particles into a solvent for swelling, heating to 60-80 ℃, adding concentrated sulfuric acid, reacting for 1-20 h, and cleaning to obtain the polystyrene microsphere resin.
Preferably, the deionized water in step (1) washes the chromatographic column at a rate of 1-4 column volumes per hour.
Preferably, the concentration of the raspberry glycoside solution in step (2) is 2% -50%.
Preferably, the speed of the raspberry glycoside solution in the step (3) flowing through the chromatographic column is 1-4 times of column volume per hour, and the volume ratio of the resin to the raspberry glycoside solution in the chromatographic column in the step (3) is 100: 1-4.
Preferably, the velocity of the eluent in the step (5) is 1 to 8 column volumes per hour.
The technical scheme of the invention has the following advantages:
according to the method for extracting raspberry glycoside by using functional polymer resin, provided by the invention, the functional polymer resin is used as a filler, deionized water is used for sampling, and pure water is used for eluting, so that the purity of raspberry glycoside can be effectively improved, and the method has the characteristics of high efficiency and low cost.
Detailed Description
The following examples are provided to further understand the present invention, not to limit the scope of the present invention, but to provide the best mode, not to limit the content and the protection scope of the present invention, and any product similar or similar to the present invention, which is obtained by combining the present invention with other prior art features, falls within the protection scope of the present invention.
The examples do not show the specific experimental steps or conditions, and can be performed according to the conventional experimental steps described in the literature in the field. The reagents or instruments used are not indicated by manufacturers, and are all conventional reagent products which can be obtained commercially.
Example 1
Adding 10g of polystyrene particles into 60mL of dichloroethane, swelling for 0.5h at 60 ℃, heating to 70 ℃, dropwise adding 100mL of concentrated sulfuric acid, heating to 80 ℃, reacting for 3h, cooling to room temperature, performing suction filtration, pouring into a 400mL beaker, cooling by using a cold water bath, adding 50mL of 25% sulfuric acid, dropwise adding 150mL of distilled water under stirring for dilution, wherein the temperature is not more than 35 ℃. And standing for 0.5h, adding water for dilution, filtering, washing twice by using 20mL of acetone to remove dichloroethane, and finally washing by using water until the filtrate is neutral to obtain the polystyrene microsphere resin.
A50X 440mm glass column is adopted, polystyrene microsphere resin is used as a separation medium, the column volume is 863.5mL, deionized water solution with 2 times of column volume is used for washing a chromatographic column, the column is soaked for 1 hour, and then deionized water with the speed of 3 column volumes per hour is used for washing the chromatographic column.
Sample preparation: 80g of crude raspberry glycoside is weighed and diluted with ultrapure water to a concentration of 20%.
Continuously loading samples at a flow rate of 2 times of column volume per hour, wherein the volume ratio of the polystyrene microsphere resin to the raspberry glycoside solution in the chromatographic column is 100: 4. After the sample loading is finished, 1 time of column volume is balanced by deionized water; then, deionized water solution is continuously used as eluent, elution is carried out at the speed of 3 times of column volume per hour, and tube separation and collection are carried out according to the UV detection condition. And combining the collected liquid with qualified purity, concentrating, and drying to obtain 57.6g of raspberry glycoside pure product.
Example 2
The polystyrene microsphere resin was prepared as described above in example 1.
A26X 300mm glass column is adopted, polystyrene microsphere resin is used as a separation medium, the column volume is 159.5mL, deionized water solution with the volume being 1 time of the column volume is used for washing the chromatographic column, the column is soaked for 2 hours, and then the deionized water with the speed being 2 column volumes per hour is used for washing the chromatographic column.
Sample preparation: weighing 12.5g of crude raspberry glycoside, and diluting with ultrapure water to 20% concentration;
continuously loading samples at a flow rate of 2 times of column volume per hour, wherein the volume ratio of the polystyrene microsphere resin to the raspberry glycoside solution in the chromatographic column is 100: 2. After the sample loading is finished, 1 time of column volume is balanced by deionized water; then, deionized water solution is continuously used as eluent, elution is carried out at the speed of 2 times of column volume per hour, and tube collection is carried out according to the UV detection condition. And combining the collected liquid with qualified purity, concentrating, and drying to obtain 8.75g of raspberry glycoside pure product.
Example 3
The polystyrene microsphere resin was prepared as described above in example 1.
A16X 100mm glass column is adopted, polystyrene microsphere resin is used as a separation medium, the column volume is 20.1mL, deionized water solution with 3 times of column volume is used for washing a chromatographic column, the column is soaked for 1 hour, and then deionized water with the speed of 2 column volumes per hour is used for washing the chromatographic column.
Sample preparation: 2.3g of crude raspberry glycoside was weighed and diluted with ultrapure water to a concentration of 20%.
Continuously loading samples at a flow rate of 2 times of column volume per hour, wherein the volume ratio of the polystyrene microsphere resin to the raspberry glycoside solution in the chromatographic column is 100: 1. After the sample loading is finished, 1 time of column volume is balanced by deionized water; then, deionized water solution is continuously used as eluent, elution is carried out at the speed of 2 times of column volume per hour, and tube collection is carried out according to the UV detection condition. And combining the collected liquid with qualified purity, concentrating, and drying to obtain 1.61g of raspberry glycoside pure product.
Example 4
Adding 10g of polystyrene particles into 60mL of dichloroethane, swelling for 0.5h at 60 ℃, dropwise adding 100mL of concentrated sulfuric acid, heating to 80 ℃, reacting for 3h, cooling to room temperature, performing suction filtration, pouring into a 400mL beaker, cooling by using a cold water bath, adding 50mL of sulfuric acid with the concentration of 30%, dropwise adding 150mL of distilled water under stirring for dilution, wherein the temperature is not more than 35 ℃. And standing for 0.5h, adding water for dilution, filtering, washing twice by using 20mL of acetone to remove dichloroethane, and finally washing by using water until the filtrate is neutral to obtain the polystyrene microsphere resin.
A50X 440mm glass column is adopted, polystyrene microsphere resin is used as a separation medium, the column volume is 863.5mL, deionized water solution with 2 times of column volume is used for washing a chromatographic column, the column is soaked for 2 hours, and then deionized water with the speed of 1 column volume per hour is used for washing the chromatographic column.
Sample preparation: 80g of crude raspberry glycoside was weighed and diluted with ultrapure water to a concentration of 2%.
Continuously loading samples at a flow rate of 1 time of column volume per hour, wherein the volume ratio of the polystyrene microsphere resin to the raspberry glycoside solution in the chromatographic column is 100: 1. After the sample loading is finished, 1 time of column volume is balanced by deionized water; then, the deionized water solution is continuously used as eluent, the elution is carried out at the speed of 1 time of column volume per hour, and the elution is collected in different tubes according to the UV detection condition. And combining the collected liquid with qualified purity, concentrating, and drying to obtain 55.6g of raspberry glycoside pure product.
Example 5
Adding 10g of polystyrene particles into 60mL of dichloroethane, swelling for 0.5h at 60 ℃, heating to 70 ℃, dropwise adding 100mL of concentrated sulfuric acid, heating to 80 ℃, reacting for 3h, cooling to room temperature, performing suction filtration, pouring into a 400mL beaker, cooling by using a cold water bath, adding 50mL of 25% sulfuric acid, dropwise adding 150mL of distilled water under stirring for dilution, wherein the temperature is not more than 35 ℃. And standing for 0.5h, adding water for dilution, filtering, washing twice by using 20mL of acetone to remove dichloroethane, and finally washing by using water until the filtrate is neutral to obtain the polystyrene microsphere resin.
A50X 440mm glass column is adopted, polystyrene microsphere resin is used as a separation medium, the column volume is 863.5mL, deionized water solution with 2 times of column volume is used for washing a chromatographic column, the column is soaked for 1 hour, and then deionized water with the speed of 4 column volumes per hour is used for washing the chromatographic column.
Sample preparation: 80g of crude raspberry glycoside is weighed and diluted with ultrapure water to 50% concentration.
Continuously loading samples at a flow rate of 4 times of column volume per hour, wherein the volume ratio of the polystyrene microsphere resin to the raspberry glycoside solution in the chromatographic column is 100: 4. After the sample loading is finished, 1 time of column volume is balanced by deionized water; then, deionized water solution is continuously used as eluent, the elution is carried out at the speed of 8 times of column volume per hour, and the elution is collected in different tubes according to the UV detection condition. And combining the collected liquid with qualified purity, concentrating, and drying to obtain 56.2g of raspberry glycoside pure product.
It should be understood that the above examples are only for clarity of illustration and are not intended to limit the embodiments. Other variations and modifications will be apparent to persons skilled in the art in light of the above description. And are neither required nor exhaustive of all embodiments. And obvious variations or modifications therefrom are within the scope of the invention.

Claims (7)

1. A method for extracting raspberry glycoside by using functional polymer resin is characterized by comprising the following steps:
(1) column packing and washing of a chromatographic column: dispersing functional polymer resin in water to form slurry, transferring the slurry to a chromatographic column, washing and compacting a chromatographic column bed by deionized water, and soaking until effluent liquid is free from peculiar smell;
(2) preparing a raspberry glycoside solution: taking the crude product of the raspberry glycoside and diluting the crude product with ultrapure water to prepare a raspberry glycoside solution;
(3) loading: continuously flowing the raspberry glycoside solution obtained in the step (2) through a chromatographic column;
(4) balancing: after the sample loading is finished, washing the chromatographic column by using ultrasonic water;
(5) and (3) elution: after the chromatographic column is balanced, taking deionized water as an eluent, separately collecting effluent liquid, and detecting the purity; combining the collected liquid with qualified purity to obtain a collected liquid;
(6) concentration: and concentrating the collected liquid, and drying to obtain the needed raspberry glycoside.
2. The method for extracting raspberry glycoside using functional polymer resin as claimed in claim 1, wherein said functional polymer resin is polystyrene microsphere resin.
3. The method for extracting raspberry glycoside using functional polymer resin as claimed in claim 2, wherein said polystyrene microsphere resin is prepared by the following steps:
adding polystyrene particles into a solvent for swelling, heating to 60-80 ℃, adding concentrated sulfuric acid, reacting for 1-20 h, and cleaning to obtain the polystyrene microsphere resin.
4. The method for extracting raspberry glycoside using functional polymer resin as claimed in claim 1, wherein the deionized water washing speed of the chromatographic column in step (1) is 1-4 column volumes per hour.
5. The method for extracting raspberry glycoside using functional polymer resin as claimed in claim 1, wherein the concentration of the raspberry glycoside solution in step (2) is 2% -50%.
6. The method for extracting raspberry glycoside using functional polymer resin as claimed in claim 1, wherein the velocity of the raspberry glycoside solution in step (3) flowing through the chromatographic column is 1-4 times column volume per hour, and the volume ratio of the resin to the raspberry glycoside solution in the chromatographic column in step (3) is 100: 1-4.
7. The method for extracting raspberry glycoside using functional polymer resin as claimed in claim 1, wherein the elution rate in step (5) is 1-8 column volumes per hour.
CN202011480966.1A 2020-12-15 2020-12-15 Method for extracting raspberry glycoside by using functional polymer resin Pending CN112500442A (en)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113092650A (en) * 2021-04-16 2021-07-09 云南中烟工业有限责任公司 Detection method of raspberry glycoside in cigarette paper

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102626661A (en) * 2012-04-11 2012-08-08 中国地质大学(武汉) Strong-acid type polystyrene cation exchange resin as well as preparation method and application thereof
CN107417696A (en) * 2017-07-17 2017-12-01 长沙爱扬医药科技有限公司 A kind of method that raspberry glycosides and ellagic acid are extracted from raspberry
CN107475208A (en) * 2017-07-17 2017-12-15 长沙湘资生物科技有限公司 The preparation method of SOD enzymes and raspberry glycosides is extracted using raspberry
CN107501365A (en) * 2017-07-17 2017-12-22 长沙湘资生物科技有限公司 A kind of method that raspberry glycosides and anthocyanin are extracted from raspberry
CN110452274A (en) * 2019-06-05 2019-11-15 南京亘闪生物科技有限公司 A kind of functional high-polymer resin is to raspberry glycosides extracting method

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102626661A (en) * 2012-04-11 2012-08-08 中国地质大学(武汉) Strong-acid type polystyrene cation exchange resin as well as preparation method and application thereof
CN107417696A (en) * 2017-07-17 2017-12-01 长沙爱扬医药科技有限公司 A kind of method that raspberry glycosides and ellagic acid are extracted from raspberry
CN107475208A (en) * 2017-07-17 2017-12-15 长沙湘资生物科技有限公司 The preparation method of SOD enzymes and raspberry glycosides is extracted using raspberry
CN107501365A (en) * 2017-07-17 2017-12-22 长沙湘资生物科技有限公司 A kind of method that raspberry glycosides and anthocyanin are extracted from raspberry
CN110452274A (en) * 2019-06-05 2019-11-15 南京亘闪生物科技有限公司 A kind of functional high-polymer resin is to raspberry glycosides extracting method

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
SHUFANG WANG等: "Characterization of the chemical constituents in Da-Huang-Gan-Cao-Tang by liquid chromatography coupled with quadrupole time-of-flight tandem mass spectrometry and liquid chromatography coupled with ion trap mass spectrometry", 《J. SEP. SCI.》 *
高重辉等: "《高分子化学》", 31 December 1997 *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113092650A (en) * 2021-04-16 2021-07-09 云南中烟工业有限责任公司 Detection method of raspberry glycoside in cigarette paper
CN113092650B (en) * 2021-04-16 2022-04-19 云南中烟工业有限责任公司 Detection method of raspberry glycoside in cigarette paper

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Application publication date: 20210316