CN113173835B - Method for preparing high-purity bakuchiol by high-speed countercurrent chromatography separation - Google Patents
Method for preparing high-purity bakuchiol by high-speed countercurrent chromatography separation Download PDFInfo
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- CN113173835B CN113173835B CN202110373590.2A CN202110373590A CN113173835B CN 113173835 B CN113173835 B CN 113173835B CN 202110373590 A CN202110373590 A CN 202110373590A CN 113173835 B CN113173835 B CN 113173835B
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- phase
- bakuchiol
- countercurrent chromatography
- fructus psoraleae
- speed countercurrent
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- LFYJSSARVMHQJB-UHFFFAOYSA-N Backuchiol Natural products CC(C)=CCCC(C)(C=C)C=CC1=CC=C(O)C=C1 LFYJSSARVMHQJB-UHFFFAOYSA-N 0.000 title claims abstract description 39
- LFYJSSARVMHQJB-GOSISDBHSA-N bakuchinol Natural products CC(C)=CCC[C@@](C)(C=C)C=CC1=CC=C(O)C=C1 LFYJSSARVMHQJB-GOSISDBHSA-N 0.000 title claims abstract description 39
- LFYJSSARVMHQJB-QIXNEVBVSA-N bakuchiol Chemical compound CC(C)=CCC[C@@](C)(C=C)\C=C\C1=CC=C(O)C=C1 LFYJSSARVMHQJB-QIXNEVBVSA-N 0.000 title claims abstract description 39
- 229940117895 bakuchiol Drugs 0.000 title claims abstract description 39
- KXXXNMZPAJTCQY-UHFFFAOYSA-N bakuchiol Natural products CC(C)CCCC(C)(C=C)C=Cc1ccc(O)cc1 KXXXNMZPAJTCQY-UHFFFAOYSA-N 0.000 title claims abstract description 39
- 238000010262 high-speed countercurrent chromatography Methods 0.000 title claims abstract description 19
- 238000000034 method Methods 0.000 title claims abstract description 14
- 238000000926 separation method Methods 0.000 title claims description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 41
- 239000002904 solvent Substances 0.000 claims abstract description 22
- 239000011259 mixed solution Substances 0.000 claims abstract description 10
- 239000000243 solution Substances 0.000 claims abstract description 9
- 230000005526 G1 to G0 transition Effects 0.000 claims abstract description 6
- 239000009083 Fructus psoraleae extract Substances 0.000 claims abstract description 5
- 239000000287 crude extract Substances 0.000 claims abstract description 5
- 238000002791 soaking Methods 0.000 claims abstract description 5
- 238000005191 phase separation Methods 0.000 claims abstract description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 7
- 238000007872 degassing Methods 0.000 claims description 4
- 238000001514 detection method Methods 0.000 claims description 4
- 238000002390 rotary evaporation Methods 0.000 claims description 4
- 238000001291 vacuum drying Methods 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 3
- 239000003153 chemical reaction reagent Substances 0.000 abstract description 7
- 238000005516 engineering process Methods 0.000 abstract description 6
- 239000000463 material Substances 0.000 abstract description 4
- 230000007613 environmental effect Effects 0.000 abstract 1
- XDROKJSWHURZGO-UHFFFAOYSA-N angelicin Chemical compound C1=C2OC=CC2=C2OC(=O)C=CC2=C1 XDROKJSWHURZGO-UHFFFAOYSA-N 0.000 description 10
- ZCCUUQDIBDJBTK-UHFFFAOYSA-N psoralen Chemical compound C1=C2OC(=O)C=CC2=CC2=C1OC=C2 ZCCUUQDIBDJBTK-UHFFFAOYSA-N 0.000 description 10
- VXGRJERITKFWPL-UHFFFAOYSA-N 4',5'-Dihydropsoralen Natural products C1=C2OC(=O)C=CC2=CC2=C1OCC2 VXGRJERITKFWPL-UHFFFAOYSA-N 0.000 description 5
- MLMVLVJMKDPYBM-UHFFFAOYSA-N pseudoisopsoralene Natural products C1=C2C=COC2=C2OC(=O)C=CC2=C1 MLMVLVJMKDPYBM-UHFFFAOYSA-N 0.000 description 5
- 239000004952 Polyamide Substances 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 229920002647 polyamide Polymers 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- 239000012259 ether extract Substances 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 244000241463 Cullen corylifolium Species 0.000 description 1
- 230000003712 anti-aging effect Effects 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000000622 liquid--liquid extraction Methods 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229930003658 monoterpene Natural products 0.000 description 1
- -1 monoterpene compound Chemical class 0.000 description 1
- 235000002577 monoterpenes Nutrition 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000002087 whitening effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/70—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment
- C07C37/82—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment by solid-liquid treatment; by chemisorption
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Extraction Or Liquid Replacement (AREA)
Abstract
The invention relates to a method for preparing high-purity bakuchiol by high-speed countercurrent chromatography, which comprises the following steps: soaking fructus Psoraleae in ethanol solution, and extracting to obtain crude fructus Psoraleae extract; fully shaking the solvent system, standing for phase separation, and collecting an upper phase and a lower phase separately; dissolving the crude extract of fructus Psoraleae in the upper phase, separating by high-speed countercurrent chromatography, wherein the upper phase is stationary phase, and the lower phase is mobile phase to obtain mixed solution of bakuchiol and lower phase, and removing the lower phase to obtain bakuchiol. The invention firstly utilizes the high-speed countercurrent chromatography technology to separate and purify the high-purity bakuchiol from the bakuchiol medicinal material, and the reagent of the solvent system can be recycled, thus having good environmental protection function.
Description
Technical Field
The invention belongs to the technical field of cosmetic raw material processing, and particularly relates to a method for preparing high-purity bakuchiol by high-speed countercurrent chromatography separation.
Background
Fructus Psoraleae is dried mature fruit of Psoralea corylifolia Psoralea corylifolia L. Bakuchiol is an important monoterpene compound in fructus Psoraleae, and has various pharmacological activities such as whitening, antibacterial, antiinflammatory, antiaging, and antioxidant effects. How to simply and rapidly prepare high-purity bakuchiol in large quantity is a close concern in the industrial production of cosmetic raw materials.
Patent CN108299453a discloses a method for separating psoralen, isopsoralen and bakuchiol from fructus psoraleae, comprising the steps of: a) Pulverizing fructus Psoraleae, extracting with petroleum ether to obtain crude petroleum ether extract of fructus Psoraleae; b) And (3) loading the crude petroleum ether extract of the fructus psoraleae on a polyamide column, carrying out gradient elution by using a mixed solution of ethanol and water, collecting target fractions, and concentrating under reduced pressure to obtain the mixture of the bakuchiol and the psoralen and the isopsoralen. The defects are that: a) The extraction rate of bakuchiol in the fructus psoraleae medicinal material is low; b) The polyamide column is a solid carrier, and the adsorption of the sample can be caused, so that the column efficiency of the polyamide column is continuously reduced and the sample is lost.
The high-speed countercurrent chromatography (HSCCC) technology is a novel separation and purification technology based on the liquid-liquid distribution principle, does not need any solid support or carrier, and has the advantages of liquid stationary phase and mobile phase and no irreversible adsorption. The method has the advantages of simplicity in operation, high efficiency, low cost and the like.
Disclosure of Invention
The invention aims to solve the technical problem of providing a method for preparing high-purity bakuchiol by high-speed countercurrent chromatography, which firstly utilizes the high-speed countercurrent chromatography technology to separate and purify the bakuchiol from the medicinal materials of the bakuchiol to obtain the high-purity bakuchiol, and reagents of a solvent system can be recycled and reused, so that the method has a good environment-friendly function.
The invention provides a method for preparing high-purity bakuchiol by high-speed countercurrent chromatography, which comprises the following steps:
Soaking fructus Psoraleae in ethanol solution, and extracting to obtain crude fructus Psoraleae extract; fully shaking the solvent system, standing for phase separation, and collecting an upper phase and a lower phase separately; dissolving crude extract of fructus Psoraleae in upper phase, separating by high-speed countercurrent chromatography, wherein the upper phase is stationary phase, and the lower phase is mobile phase to obtain mixed solution of bakuchiol and lower phase, and removing the lower phase to obtain bakuchiol; wherein the solvent system is prepared by mixing n-hexane or n-heptane, methanol or ethanol and water according to the volume ratio of 3-6:3-6:0-3.
The mass concentration of the ethanol solution is 95%.
The upper and lower phases collected separately are subjected to ultrasonic degassing treatment in advance.
The conditions of the high-speed countercurrent chromatography are as follows: the rotation speed is 400rpm; the column temperature is 25 ℃; the flow rate of the mobile phase is 200mL/min; the detection wavelength of the detector was 254nm.
The process conditions for removing the lower phase are as follows: rotary evaporation vacuum drying is carried out at 55 deg.c and-0.085 MPa.
The solvent system is determined by the solubility of bakuchiol, psoralen, and isopsoralen in mutually immiscible two-phase solvents.
Advantageous effects
The high-purity bakuchiol is obtained by separating and purifying the bakuchiol from the bakuchiol by a high-speed countercurrent chromatography technology for the first time, and the reagents of a solvent system can be recycled, so that the high-purity bakuchiol has a good environment-friendly function; the high-speed countercurrent chromatography technology has the advantages of no sample loss, no pollution, high efficiency, large preparation amount, recoverable and reusable solvent, and the annual yield of the high-purity bakuchiol can reach ton level.
Detailed Description
The application will be further illustrated with reference to specific examples. It is to be understood that these examples are illustrative of the present application and are not intended to limit the scope of the present application. Furthermore, it should be understood that various changes and modifications can be made by one skilled in the art after reading the teachings of the present application, and such equivalents are intended to fall within the scope of the application as defined in the appended claims.
The reagents and instrumentation used in the examples were as follows:
reagent: n-hexane, n-heptane, methanol and ethanol are all analytically pure reagents produced by national pharmaceutical group chemical reagent company, water is deionized water, and fructus Psoraleae medicinal materials are commercial products;
instrument: the high-speed countercurrent chromatograph is TSS-M10 model high-speed countercurrent chromatograph manufactured by Shanghai Tongtian Biotechnology Co., ltd.
Example 1
Soaking fructus Psoraleae in 95wt% ethanol solution at room temperature, stirring at room temperature, and extracting to remove 95wt% ethanol solution to obtain crude fructus Psoraleae extract. N-hexane, methanol and water are mixed according to the volume ratio of 5:5:1, adding the mixture into a separating funnel, fully shaking, standing and phase-separating to obtain a two-phase mixed solution, separately collecting an upper phase solvent and a lower phase solvent, respectively placing the two phases of solvents into an ultrasonic oscillator for ultrasonic degassing treatment, dissolving the crude extract of the fructus psoraleae in the upper phase solvent, and separating by adopting high-speed countercurrent chromatography: the upper phase is a stationary phase, the lower phase is a mobile phase, and the mixed solution of bakuchiol and the lower phase is obtained in 55-70 min according to the sample feeding time of 0 min; wherein the chromatographic conditions are set as follows: the rotation speed is 400rpm; column temperature 25 ℃; the flow rate of the mobile phase is 200mL/min; the detection wavelength of the detector was 254nm. And then placing the obtained mixed solution of bakuchiol and the lower phase in a rotary evaporator, carrying out rotary evaporation vacuum drying under the conditions of water bath temperature of 55 ℃ and vacuum pressure of-0.085 MPa, and removing the lower phase to obtain a bakuchiol product.
The purity of the bakuchiol product obtained in this example was analyzed by HPLC and the results showed that: the purity of the bakuchiol is 99.36% (without psoralen and isopsoralen).
Example 2
Soaking fructus Psoraleae in 95wt% ethanol solution at room temperature, stirring at room temperature, and extracting to remove 95wt% ethanol solution to obtain crude fructus Psoraleae extract. N-heptane, ethanol and water are mixed according to the volume ratio of 5:5:2, mixing to prepare a solvent system, adding the solvent system into a separating funnel, fully shaking, standing and phase-separating to obtain a two-phase mixed solution, separately collecting an upper phase solvent and a lower phase solvent, respectively placing the upper phase solvent and the lower phase solvent into an ultrasonic oscillator for ultrasonic degassing treatment, dissolving the crude extract of the fructus psoraleae in the upper phase solvent, and separating by adopting high-speed countercurrent chromatography: the upper phase is a stationary phase, the lower phase is a mobile phase, and the mixed solution of bakuchiol and the lower phase is obtained in 40-50 min based on 0min after sample feeding; wherein the chromatographic conditions are set as follows: the rotation speed is 400rpm; column temperature 25 ℃; the flow rate of the mobile phase is 200mL/min; the detection wavelength of the detector was 254nm. And then placing the obtained mixed solution of bakuchiol and the lower phase in a rotary evaporator, carrying out rotary evaporation vacuum drying under the conditions of water bath temperature of 55 ℃ and vacuum pressure of-0.085 MPa, and removing the lower phase to obtain a bakuchiol product.
The purity of the bakuchiol product obtained in this example was analyzed by HPLC and the results showed that: the purity of bakuchiol is 99.21% (without psoralen and isopsoralen).
Claims (3)
1. A method for preparing high-purity bakuchiol by high-speed countercurrent chromatography separation comprises the following steps:
Soaking fructus Psoraleae in ethanol solution, and extracting to obtain crude fructus Psoraleae extract; fully shaking the solvent system, standing for phase separation, and collecting an upper phase and a lower phase separately; dissolving crude extract of fructus Psoraleae in upper phase, separating by high-speed countercurrent chromatography, wherein the upper phase is stationary phase, and the lower phase is mobile phase to obtain mixed solution of bakuchiol and lower phase, and removing the lower phase to obtain bakuchiol; wherein the solvent system is prepared by mixing n-hexane or n-heptane, methanol or ethanol and water according to the volume ratio of 3-6:3-6:0-3;
The mass concentration of the ethanol solution is 95%; the conditions of the high-speed countercurrent chromatography are as follows: the rotation speed is 400rpm; the column temperature is 25 ℃; the flow rate of the mobile phase is 200mL/min; the detection wavelength of the detector was 254nm.
2. The method according to claim 1, characterized in that: the upper and lower phases collected separately are subjected to ultrasonic degassing treatment in advance.
3. The method according to claim 1, characterized in that: the process conditions for removing the lower phase are as follows: rotary evaporation vacuum drying is carried out at 55 deg.c and-0.085 MPa.
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| CN202110373590.2A CN113173835B (en) | 2021-04-07 | 2021-04-07 | Method for preparing high-purity bakuchiol by high-speed countercurrent chromatography separation |
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| CN202110373590.2A CN113173835B (en) | 2021-04-07 | 2021-04-07 | Method for preparing high-purity bakuchiol by high-speed countercurrent chromatography separation |
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Non-Patent Citations (1)
| Title |
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| 补骨脂及伤疖膏的CPC分离及近红外分析;姜博海;《中国优秀硕士学位论文全文数据库 医药卫生科技辑》;20121015;第15-21页 * |
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