CN115417749A - Extraction method of bakuchiol - Google Patents
Extraction method of bakuchiol Download PDFInfo
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- CN115417749A CN115417749A CN202211135325.1A CN202211135325A CN115417749A CN 115417749 A CN115417749 A CN 115417749A CN 202211135325 A CN202211135325 A CN 202211135325A CN 115417749 A CN115417749 A CN 115417749A
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- bakuchiol
- extracting
- fructus psoraleae
- silica gel
- extraction
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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 80
- 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 80
- 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 80
- 229940117895 bakuchiol Drugs 0.000 title claims abstract description 80
- 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 80
- 238000000605 extraction Methods 0.000 title claims abstract description 61
- 238000000034 method Methods 0.000 claims abstract description 54
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims abstract description 45
- 239000000287 crude extract Substances 0.000 claims abstract description 33
- 239000000843 powder Substances 0.000 claims abstract description 32
- 229960000583 acetic acid Drugs 0.000 claims abstract description 22
- 239000012362 glacial acetic acid Substances 0.000 claims abstract description 21
- 238000002137 ultrasound extraction Methods 0.000 claims abstract description 21
- 238000010438 heat treatment Methods 0.000 claims abstract description 20
- 238000002156 mixing Methods 0.000 claims abstract description 12
- 239000002904 solvent Substances 0.000 claims abstract description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 33
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 24
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 22
- 239000000741 silica gel Substances 0.000 claims description 22
- 229910002027 silica gel Inorganic materials 0.000 claims description 22
- 239000003208 petroleum Substances 0.000 claims description 20
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 18
- 239000000284 extract Substances 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 14
- ZCCUUQDIBDJBTK-UHFFFAOYSA-N psoralen Chemical compound C1=C2OC(=O)C=CC2=CC2=C1OC=C2 ZCCUUQDIBDJBTK-UHFFFAOYSA-N 0.000 claims description 10
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 9
- SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 claims description 8
- 235000019441 ethanol Nutrition 0.000 claims description 7
- 238000004440 column chromatography Methods 0.000 claims description 6
- 238000010898 silica gel chromatography Methods 0.000 claims description 6
- VXGRJERITKFWPL-UHFFFAOYSA-N 4',5'-Dihydropsoralen Natural products C1=C2OC(=O)C=CC2=CC2=C1OCC2 VXGRJERITKFWPL-UHFFFAOYSA-N 0.000 claims description 5
- 241001446509 Psoralea Species 0.000 claims description 5
- 238000011068 loading method Methods 0.000 claims description 4
- 238000001035 drying Methods 0.000 claims description 2
- 238000004904 shortening Methods 0.000 abstract description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- 238000001514 detection method Methods 0.000 description 10
- 238000004128 high performance liquid chromatography Methods 0.000 description 10
- 244000241463 Cullen corylifolium Species 0.000 description 8
- 235000013399 edible fruits Nutrition 0.000 description 8
- 239000002253 acid Substances 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 210000004027 cell Anatomy 0.000 description 5
- 238000010828 elution Methods 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000010829 isocratic elution Methods 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 238000007873 sieving Methods 0.000 description 3
- 238000010025 steaming Methods 0.000 description 3
- 102000008186 Collagen Human genes 0.000 description 2
- 108010035532 Collagen Proteins 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 2
- XDROKJSWHURZGO-UHFFFAOYSA-N angelicin Chemical compound C1=C2OC=CC2=C2OC(=O)C=CC2=C1 XDROKJSWHURZGO-UHFFFAOYSA-N 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 210000002421 cell wall Anatomy 0.000 description 2
- 229920001436 collagen Polymers 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 230000000149 penetrating effect Effects 0.000 description 2
- 230000035699 permeability Effects 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 238000010298 pulverizing process Methods 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- FPIPGXGPPPQFEQ-UHFFFAOYSA-N 13-cis retinol Natural products OCC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241000220485 Fabaceae Species 0.000 description 1
- 208000001132 Osteoporosis Diseases 0.000 description 1
- 238000003916 acid precipitation Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 238000004458 analytical method Methods 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
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000003796 beauty Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- HQVFCQRVQFYGRJ-UHFFFAOYSA-N formic acid;hydrate Chemical compound O.OC=O HQVFCQRVQFYGRJ-UHFFFAOYSA-N 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- MLMVLVJMKDPYBM-UHFFFAOYSA-N pseudoisopsoralene Natural products C1=C2C=COC2=C2OC(=O)C=CC2=C1 MLMVLVJMKDPYBM-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000004492 retinoid derivatives Chemical class 0.000 description 1
- 229960003471 retinol Drugs 0.000 description 1
- 235000020944 retinol Nutrition 0.000 description 1
- 239000011607 retinol Substances 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 238000013341 scale-up Methods 0.000 description 1
- 210000001626 skin fibroblast Anatomy 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 210000000952 spleen Anatomy 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
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- 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
- C07C37/004—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by obtaining phenols from plant material or from animal material
-
- 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
- C07C37/685—Processes comprising at least two steps in series
-
- 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
-
- 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)
- Life Sciences & Earth Sciences (AREA)
- Botany (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Extraction Or Liquid Replacement (AREA)
Abstract
The invention discloses a method for extracting bakuchiol, which comprises the following steps: s1, crushing fructus psoraleae to obtain fructus psoraleae powder; s2, mixing the fructus psoraleae powder with glacial acetic acid, and then heating by steam to obtain steamed fructus psoraleae powder; and S3, adding a solvent into the steamed fructus psoraleae powder for ultrasonic extraction to obtain a crude extract of the bakuchiol. The invention has the characteristics of improving the extraction rate, shortening the extraction time and saving the cost.
Description
Technical Field
The invention belongs to the technical field of natural medicine purification, and particularly relates to a method for extracting bakuchiol.
Background
Fructus Psoraleae is dry mature fruit of Psoralea corylifolia of Psoralea of Leguminosae, also called fructus Psoraleae, and has effects of invigorating kidney, tonifying yang, invigorating spleen and invigorating stomach. Bakuchiol is an active ingredient isolated from the fruit of Bakuchio, and has antibacterial, antiinflammatory, antioxidant and osteoporosis resisting effects. In recent years, the research on bakuchiol at home and abroad is gradually increased, the beauty and skin care effects of bakuchiol attract wide attention, and the bakuchiol is a potential cosmetic active ingredient with various efficacies. Because the functions of the bakuchiol and the retinol are similar, the bakuchiol is also called as a functional retinoid component, can enhance the antioxidant activity of human skin fibroblasts, reduce the decomposition of skin collagen, and simultaneously can promote the synthesis of the skin collagen to achieve the anti-aging effect.
At present, the methods for extracting bakuchiol from fructus psoraleae are roughly classified into the following 4 types: 1. liu Erwei, etc. (D101 macroporous adsorption resin method for enriching bakuchiol in fructus psoraleae [ J ]. Tianjin Chinese medicine university report, 2012, 31 (02): 95-97.) directly uses 95% ethanol to reflux and extract fructus psoraleae raw medicinal materials, uses an alkali extraction and acid precipitation method to carry out primary separation, uses a macroporous resin separation method to extract a bakuchiol pure product, and finally achieves the purity of the bakuchiol of 45.6%. However, the extraction and separation process is complicated, the time consumption is long, and the purification efficiency is low. Meanwhile, a large amount of acid-base reagents are used, and the environment is damaged if the method is used for industrial scale-up production. 2. Chinese invention patent CN105237361A discloses bakuchiol extract and its preparation method and application: pulverizing fructus Psoraleae, cold extracting with petroleum ether to obtain crude extract, separating with silica gel column for 2 times, and eluting with petroleum ether-ethyl acetate mixture to obtain pure bakuchiol. Although the purity of the separated bakuchiol reaches 98%, the direct cold-leaching extraction using petroleum ether consumes long time, the overall extraction rate is not high, the highest extraction rate of a crude extract is only 13.96%, and the highest extraction rate of the bakuchiol is only 2.93%. 3. Chinese patent CN108299453A discloses a method for separating psoralen, isopsoralen and bakuchiol from fructus psoraleae, which comprises the following steps: crushing the malaytea scurfpea fruit medicinal material, and performing ultrasonic extraction by using petroleum ether to obtain a malaytea scurfpea fruit phenol crude extract. Then separating by polyamide of 100-200 meshes, and performing gradient elution by using an ethanol-water mixed solution to obtain the bakuchiol with the purity of 99.3%. Although the purity of the separated bakuchiol is high, the cost for industrial large-scale production is high due to the high price of polyamide filler, the extraction rate of the crude extract obtained by the method is only 9.60 percent at most, the extraction rate of the bakuchiol is 2.18 percent at most, and the extraction rate is not high. 4. Chinese patent CN112723997A discloses a green process for extracting high-purity bakuchiol: pulverizing dried fructus Psoraleae, placing into an extraction kettle, extracting with supercritical carbon dioxide to obtain crude extract, and separating with silica gel column. Although the purity of the bakuchiol extracted by the method is more than 98 percent, the supercritical carbon dioxide technology has higher cost, complicated steps and longer extraction time, and the extraction rate of the crude extract obtained by the method is 8.36 percent, the net extraction rate of the bakuchiol is 5.03 percent, and the extraction rate is still not high. Therefore, the existing extraction method of bakuchiol has the problems of low extraction rate, long time consumption and high cost.
Disclosure of Invention
The invention aims to provide a method for extracting bakuchiol. The invention has the characteristics of improving the extraction rate, shortening the extraction time and saving the cost.
The technical scheme of the invention is as follows: a method for extracting bakuchiol comprises the following steps:
s1, crushing fructus psoraleae to obtain fructus psoraleae powder;
s2, mixing the fructus psoraleae powder with glacial acetic acid, and then heating by steam to obtain steamed fructus psoraleae powder;
and S3, adding a solvent into the steamed fructus psoraleae powder for ultrasonic extraction to obtain a crude extract of the bakuchiol.
In the method for extracting bakuchiol, in step S2, the mass-to-volume ratio of the bakuchiol powder to the glacial acetic acid is 1 to 3.
In the foregoing method for extracting bakuchiol, in step S2, the steam heating temperature is 100 to 105 ℃ and the steam heating time is 5 to 30min.
In the foregoing method for extracting bakuchiol, in step S3, the solvent for ultrasonic extraction includes absolute ethanol.
In the above method for extracting bakuchiol, the volume ratio of glacial acetic acid to absolute ethyl alcohol is 1.
In the extraction method of bakuchiol, the ultrasonic extraction power is 70-90 kHz, the temperature is 20-30 ℃, the extraction frequency is 1-4 times, and each time of extraction is 0.5-1.5 h.
In the foregoing method for extracting bakuchiol, the crude extract of bakuchiol is purified by silica gel column chromatography to obtain a pure product of bakuchiol.
In the foregoing extraction method of bakuchiol, the purification method by silica gel column chromatography includes: mixing the crude extract with silica gel, isocratic eluting with petroleum ether-ethyl acetate, and collecting target fraction to obtain pure bakuchiol.
In the extraction method of bakuchiol, the mass ratio of the bakuchiol crude extract to the silica gel is (1-3) to (1-3).
In the method for extracting bakuchiol, the volume ratio of the petroleum ether to the ethyl acetate is (35-45) to 1.
Compared with the prior art, the invention has the beneficial effects that:
the invention firstly utilizes 100 percent of glacial acetic acid to be mixed with the fructus psoraleae powder, the glacial acetic acid goes deep into the cells of the fructus psoraleae, the cell walls of the fructus psoraleae are destroyed as much as possible, and the permeability inside and outside the cells is increased; by means of the penetrating power of steam heating, glacial acetic acid is heated and volatilized, so that substances in the fructus psoraleae cells reach the surface as far as possible, subsequent ultrasonic extraction is facilitated, and the extraction efficiency is improved; finally, ultrasonic extraction is assisted, so that the extraction rate of the crude extract can be increased to the maximum extent.
And the fructus psoraleae is mixed with glacial acetic acid before steam heating, and after steam treatment, the glacial acetic acid is remained in the fructus psoraleae, so that the fructus psoraleae does not need to be added with the glacial acetic acid as an extraction solvent in subsequent ultrasonic extracts, and the cost is reduced.
The invention firstly adopts glacial acetic acid and steam to treat the raw material of the malaytea scurfpea fruit, has simple and efficient extraction method, short time consumption, low cost and high yield, and has obvious promotion effect on the development of the economic value and the medicinal value of the malaytea scurfpea fruit phenol. Experimental results show that by adopting the extraction method, the extraction rate of the crude extract of the bakuchiol can reach 25.3 percent, and the net extraction rate of the pure product of the bakuchiol can reach 5.98 percent.
Therefore, the invention has the characteristics of improving the extraction rate, shortening the extraction time and saving the extraction cost.
Drawings
FIG. 1 is an HPLC detection chromatogram of example 1;
FIG. 2 is an HPLC detection chromatogram of example 5;
FIG. 3 is an HPLC detection chromatogram of example 6;
FIG. 4 is an HPLC detection chromatogram of example 7;
FIG. 5 is an HPLC detection chromatogram of comparative example 1;
FIG. 6 is an HPLC detection chromatogram of comparative example 2;
FIG. 7 is an HPLC detection chromatogram of example 4.
Detailed Description
A method for extracting bakuchiol comprises the following steps:
s1, crushing fructus psoraleae to obtain fructus psoraleae powder; the particle size of the fructus psoraleae powder is 40-100 meshes.
S2, mixing the fructus psoraleae powder with glacial acetic acid according to a mass volume ratio of 1-3 to 1g/mL, and then heating by steam at 100-105 ℃ for 5-30 min to obtain steamed fructus psoraleae powder;
s3, adding a solvent into the steamed fructus psoraleae powder for ultrasonic extraction, wherein the solvent for ultrasonic extraction comprises absolute ethyl alcohol, and the volume ratio of the glacial acetic acid to the absolute ethyl alcohol is 1-8. The power of ultrasonic extraction is 70-90 kHz, the temperature is 20-30 ℃, the extraction frequency is 1-4 times, and each extraction time is 0.5-1.5 h.
After ultrasonic extraction, filtering by adopting qualitative filter paper, and finally combining the extracting solutions each time to obtain the psoralea corylifoliol crude extract.
The invention firstly utilizes acetic acid to destroy cell walls as much as possible and increase permeability inside and outside cells, then utilizes the penetrating power of steam heating to enable substances inside the psoralea corylifolia cells to reach the surface as much as possible, and finally is assisted with ultrasonic extraction, so that the extraction rate of crude extract can be increased to the maximum extent.
And purifying the crude psoralen extract by silica gel column chromatography to obtain a pure psoralen product. The purification method of the silica gel column chromatography comprises the following steps: dissolving the crude psoralea corylifoliol extract by 50-100 mL of absolute ethyl alcohol to obtain a crude ethanol mixture; uniformly mixing the crude extraction ethanol mixture and silica gel according to the mass ratio of (1-3) to (1-3), and drying to obtain a crude extraction silica gel mixture; weighing the crude silica gel mixture and column chromatography silica gel according to the mass ratio of 1 (4-6), and loading the crude silica gel mixture and the column chromatography silica gel by a dry method; petroleum ether-ethyl acetate isocratic elution in the volume ratio of 35-45 to 1, and collecting the target fraction to obtain the pure bakuchiol product.
In the invention, before the purification step, petroleum ether and ethyl acetate are steamed again in advance, so that impurities contained in the solvent are removed as much as possible; before loading, the chromatographic column is eluted by 3 column volumes by using redistilled petroleum ether, and then eluted by 3 column volumes by using petroleum ether-ethyl acetate with the volume ratio of 40.
The reagents involved in the invention are analytically pure.
All reagents of the invention are purchased from Tianjin North-linked chemical reagents, inc.; the silica gel column is column chromatography silica gel (200-300 meshes) from Qingdao ocean chemical Co.
The fructus psoraleae raw material medicine is purchased from Fengyi pharmaceutical industry group Limited company in Anguo city, and is identified by medicinal plant research institute of Chinese medical academy of sciences, so that the source of the medicinal material is reliable.
The present invention is further illustrated by the following examples, which are not to be construed as limiting the invention.
Example 1:
a method for extracting bakuchiol comprises the following steps:
s1, crushing 100g of fructus psoraleae, and sieving with a 60-mesh sieve to obtain fructus psoraleae powder;
s2, mixing the fructus psoraleae powder with 50mL of glacial acetic acid, and heating for 10min by using steam at 100-105 ℃ to obtain steamed fructus psoraleae powder;
s3, cooling the steamed fructus psoraleae powder to room temperature, carrying out ultrasonic extraction in 500mL of absolute ethyl alcohol for 3 times, wherein the ultrasonic extraction time is 1h each time, the extraction temperature is 25 ℃, the extraction power is 85kHz, filtering, combining filtrates, and carrying out reduced pressure concentration to obtain a fructus psoraleae phenol extract crude extract.
Example 2:
a method for extracting bakuchiol comprises the following steps:
s1, crushing 300g of fructus psoraleae, and sieving with a 40-mesh sieve to obtain fructus psoraleae powder;
s2, mixing the fructus psoraleae powder with 50mL of glacial acetic acid, and heating for 5min by using steam at 100-105 ℃ to obtain steamed fructus psoraleae powder;
and S3, cooling the steamed malaytea scurfpea fruit powder to room temperature, carrying out ultrasonic extraction in 400mL of absolute ethyl alcohol for 4 times, wherein the ultrasonic extraction time is 0.5h each time, the extraction temperature is 30 ℃, the extraction power is 70kHz, filtering, combining filtrates, and carrying out reduced pressure concentration to obtain a malaytea scurfpea fruit phenol extract crude extract.
Example 3:
a method for extracting bakuchiol comprises the following steps:
s1, crushing 50g of fructus psoraleae, and sieving with a 100-mesh sieve to obtain fructus psoraleae powder;
s2, mixing the fructus psoraleae powder with 50mL of glacial acetic acid, and heating for 20min by using steam at 100-105 ℃ to obtain steamed fructus psoraleae powder;
and S3, cooling the steamed fructus psoraleae powder to room temperature, carrying out ultrasonic extraction in 600mL of absolute ethyl alcohol for 2 times, wherein the ultrasonic extraction time is 1h each time, the extraction temperature is 20 ℃, the extraction power is 90kHz, filtering, combining filtrates, and carrying out reduced pressure concentration to obtain a crude extract of the bakuchiol extract.
Example 4:
the method for purifying the crude extract of the bakuchiol extract comprises the following steps:
(1) Mixing the crude extract of the psoralea corylifolial extract obtained in the embodiment 1 with 60mL of absolute ethyl alcohol to obtain a crude ethanol mixture;
(2) Uniformly mixing the crude ethanol mixture with silica gel according to a mass ratio of 1;
(3) Weighing the crude silica gel mixture and column chromatography silica gel according to a mass ratio of 1;
(4) And (3) carrying out dry-method sample loading, carrying out isocratic elution by using petroleum ether-ethyl acetate with the volume ratio of 40.
Before sampling, redistilling petroleum ether and ethyl acetate to remove impurities contained in the solvent, eluting by redistilled petroleum ether for 3 column volumes, and eluting by petroleum ether-ethyl acetate with a volume ratio of 40.
Example 5:
a method for extracting bakuchiol comprises the same steps as those in example 1 except that steam heating is carried out for 5min to obtain a crude extract of bakuchiol.
Example 6:
a method for extracting bakuchiol, the specific implementation mode is the same as that of example 1, except that steam heating time is 20min, to obtain a crude extract of bakuchiol extract.
Example 7:
a method for extracting bakuchiol, the specific implementation mode is the same as that of example 1, except that steam heating time is 30min, to obtain a crude extract of bakuchiol extract.
Comparative example 1:
a method for extracting bakuchiol comprises the same steps as those in example 1 except that the crude extract of bakuchiol is obtained without steam heating.
Comparative example 2:
a method for extracting bakuchiol, the specific implementation mode is the same as that in example 1, except that glacial acetic acid is not used for treatment, and a crude extract of bakuchiol extract is obtained.
And (3) detection of extraction rate:
the weights of the crude extract of the embodiment 1, the embodiment 5-7 and the comparative embodiment 1-2 are respectively measured, the extraction rate is calculated, the purity of the crude extract and the purity of the bakuchiol product of the embodiment 4 are detected by HPLC, the net extraction rate is calculated, and the specific calculation results are shown in the table 1 and the figures 1-7.
Wherein, the extraction rate = the weight of the crude extract of the extractum/the mass of the raw medicinal materials of the fructus psoraleae is 100%;
net extraction rate = (pure quality of bakuchiol)/raw material of bakuchiol mass 100%;
the HPLC detection analysis conditions are as follows: high performance liquid chromatography: agilent 1200; and (3) chromatographic column: waters XBridge (4.6 x 250mm,5 μm);
column temperature: 40 ℃;
mobile phase: mobile phase A is acetonitrile, mobile phase B is 0.1% volume fraction formic acid water solution
The gradient elution procedure was: 0-5 min, acetonitrile, 20 percent of acid water and 80 percent of isocratic elution; 5-10min, acetonitrile, 20 percent of acid water, 80-50 percent of acid water and 50 percent of acid water are added for gradient elution; 10-20min, acetonitrile, 50 percent of acid water, 50 percent to 65 percent and 35 percent of gradient elution; 20-30min, acetonitrile, acid water 65%, 35-100%, and 0% gradient elution;
flow rate: 1mL/min;
detection wavelength: 262 And 310nm.
TABLE 1 psoralen extraction, purity and net extraction for each example and comparative example
As can be seen from Table 1, time parameter experiments show that the extraction rate of the crude extract can reach the highest by steaming for 20min, but in consideration of energy and cost saving, the extraction rate can reach more than 25% by steaming for 10min, and the improvement of the extraction rate of the crude extract after steaming for 10min is not obvious, so 10min is selected as the optimal steam heating time. In addition, compared with the method without adding glacial acetic acid or heating by steam, the method disclosed by the embodiment 1 of the invention can obviously improve the purity and the net extraction rate of the bakuchiol.
Claims (10)
1. A method for extracting bakuchiol is characterized in that: the method comprises the following steps:
s1, crushing fructus psoraleae to obtain fructus psoraleae powder;
s2, mixing the fructus psoraleae powder with glacial acetic acid, and then heating by steam to obtain steamed fructus psoraleae powder;
and S3, adding a solvent into the steamed fructus psoraleae powder for ultrasonic extraction to obtain a crude extract of the bakuchiol.
2. The method for extracting bakuchiol according to claim 1, wherein the method comprises the following steps: in the step S2, the mass-volume ratio of the fructus psoraleae powder to the glacial acetic acid is 1-3.
3. The method for extracting bakuchiol according to claim 1, wherein the method comprises the following steps: in the step S2, the steam heating temperature is 100-105 ℃, and the steam heating time is 5-30 min.
4. The method for extracting bakuchiol according to claim 1, wherein the method comprises the following steps: in step S3, the solvent for ultrasonic extraction includes absolute ethanol.
5. The method for extracting bakuchiol according to claim 4, wherein the method comprises the following steps: the volume ratio of the glacial acetic acid to the absolute ethyl alcohol is 1.
6. The method for extracting bakuchiol according to claim 1, wherein the method comprises the following steps: the power of ultrasonic extraction is 70-90 kHz, the temperature is 20-30 ℃, the extraction frequency is 1-4 times, and each extraction time is 0.5-1.5 h.
7. The method for extracting bakuchiol according to claim 1, wherein the method comprises the following steps: and purifying the crude extract of the bakuchiol by silica gel column chromatography to obtain a pure product of the bakuchiol.
8. The method for extracting bakuchiol according to claim 7, wherein the method for purifying by silica gel column chromatography comprises: dissolving the crude psoralea phenol extract with absolute ethyl alcohol to obtain a crude ethanol mixture; mixing the crude ethanol mixture with silica gel to obtain a crude silica gel mixture; and (3) carrying out dry-process sample loading on the crude silica gel mixture and column chromatography silica gel, isocratically eluting through petroleum ether-ethyl acetate, and collecting target fractions to obtain a pure psoralen product.
9. The method for extracting bakuchiol according to claim 8, wherein the mass ratio of the bakuchiol crude extract to the silica gel is (1-3) to (1-3); the mass ratio of the crude silica gel mixture to the column chromatography silica gel is 1 (4-6); the volume ratio of the petroleum ether to the ethyl acetate is (35-45): 1.
10. The method of claim 8, wherein the petroleum ether and ethyl acetate are redistilled petroleum ether and ethyl acetate, and the 3 column volumes are eluted with redistilled petroleum ether and then with petroleum ether-ethyl acetate at a volume ratio of 40.
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| CN103553994A (en) * | 2013-11-08 | 2014-02-05 | 山东百龙创园生物科技有限公司 | Method for preparing astaxanthin missible oil through phaffia rhodozyma thallus |
| CN112939742A (en) * | 2021-04-14 | 2021-06-11 | 龙麻(上海)医药研发有限责任公司 | Method for extracting and purifying cannabinoid |
| CN113577165A (en) * | 2021-07-31 | 2021-11-02 | 海南黎草纪新生物科技有限公司 | Method for extracting polyphenol from camellia japonica |
| CN114478196A (en) * | 2021-01-27 | 2022-05-13 | 江苏巴帝恩生物科技有限公司 | Method for extracting and purifying bakuchiol from radix Ulmi Pumilae and its application in cosmetics |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN103553994A (en) * | 2013-11-08 | 2014-02-05 | 山东百龙创园生物科技有限公司 | Method for preparing astaxanthin missible oil through phaffia rhodozyma thallus |
| CN114478196A (en) * | 2021-01-27 | 2022-05-13 | 江苏巴帝恩生物科技有限公司 | Method for extracting and purifying bakuchiol from radix Ulmi Pumilae and its application in cosmetics |
| CN112939742A (en) * | 2021-04-14 | 2021-06-11 | 龙麻(上海)医药研发有限责任公司 | Method for extracting and purifying cannabinoid |
| CN113577165A (en) * | 2021-07-31 | 2021-11-02 | 海南黎草纪新生物科技有限公司 | Method for extracting polyphenol from camellia japonica |
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