CN111978366A - Method for extracting dioscin from fenugreek - Google Patents
Method for extracting dioscin from fenugreek Download PDFInfo
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- CN111978366A CN111978366A CN202010900562.7A CN202010900562A CN111978366A CN 111978366 A CN111978366 A CN 111978366A CN 202010900562 A CN202010900562 A CN 202010900562A CN 111978366 A CN111978366 A CN 111978366A
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- CN
- China
- Prior art keywords
- fenugreek
- dioscin
- extracting
- ultrasonic
- filtrate
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- Pending
Links
- HDXIQHTUNGFJIC-UHFFFAOYSA-N (25R)-spirost-5-en-3beta-ol 3-O-<O-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-glucopyranoside> Natural products O1C2(OCC(C)CC2)C(C)C(C2(CCC3C4(C)CC5)C)C1CC2C3CC=C4CC5OC1OC(CO)C(O)C(O)C1OC1OC(C)C(O)C(O)C1O HDXIQHTUNGFJIC-UHFFFAOYSA-N 0.000 title claims abstract description 26
- VNONINPVFQTJOC-RXEYMUOJSA-N Collettiside III Natural products O([C@@H]1[C@@H](O)[C@H](O[C@H]2[C@H](O)[C@H](O)[C@@H](O)[C@H](C)O2)[C@H](CO)O[C@@H]1O[C@@H]1CC=2[C@@](C)([C@@H]3[C@H]([C@H]4[C@@](C)([C@H]5[C@H](C)[C@@]6(O[C@H]5C4)OC[C@H](C)CC6)CC3)CC=2)CC1)[C@H]1[C@H](O)[C@H](O)[C@@H](O)[C@H](C)O1 VNONINPVFQTJOC-RXEYMUOJSA-N 0.000 title claims abstract description 26
- VNONINPVFQTJOC-ZGXDEBHDSA-N dioscin Chemical compound O([C@@H]1[C@@H](CO)O[C@H]([C@@H]([C@H]1O)O[C@H]1[C@@H]([C@H](O)[C@@H](O)[C@H](C)O1)O)O[C@@H]1CC2=CC[C@H]3[C@@H]4C[C@H]5[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@@H]([C@]1(OC[C@H](C)CC1)O5)C)[C@@H]1O[C@@H](C)[C@H](O)[C@@H](O)[C@H]1O VNONINPVFQTJOC-ZGXDEBHDSA-N 0.000 title claims abstract description 26
- CJNUQCDDINHHHD-APRUHSSNSA-N dioscin Natural products C[C@@H]1CC[C@@]2(OC1)O[C@H]3C[C@H]4[C@@H]5CC=C6C[C@H](CC[C@@H]6[C@H]5CC[C@]4(C)[C@H]3[C@@H]2C)O[C@@H]7O[C@H](CO)[C@@H](O[C@@H]8O[C@@H](C)[C@H](O)[C@@H](O)[C@H]8O)[C@H](O)[C@H]7O[C@@H]9O[C@@H](C)[C@H](O)[C@@H](O)[C@H]9O CJNUQCDDINHHHD-APRUHSSNSA-N 0.000 title claims abstract description 26
- VNONINPVFQTJOC-UHFFFAOYSA-N polyphyllin III Natural products O1C2(OCC(C)CC2)C(C)C(C2(CCC3C4(C)CC5)C)C1CC2C3CC=C4CC5OC(C(C1O)OC2C(C(O)C(O)C(C)O2)O)OC(CO)C1OC1OC(C)C(O)C(O)C1O VNONINPVFQTJOC-UHFFFAOYSA-N 0.000 title claims abstract description 26
- 235000001484 Trigonella foenum graecum Nutrition 0.000 title claims abstract description 19
- 244000250129 Trigonella foenum graecum Species 0.000 title claims abstract description 19
- 235000001019 trigonella foenum-graecum Nutrition 0.000 title claims abstract description 19
- 238000000034 method Methods 0.000 title claims abstract description 17
- 238000000605 extraction Methods 0.000 claims abstract description 19
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims abstract description 18
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims abstract description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000012535 impurity Substances 0.000 claims abstract description 10
- 239000000706 filtrate Substances 0.000 claims abstract description 8
- 238000001035 drying Methods 0.000 claims abstract description 7
- 239000003208 petroleum Substances 0.000 claims abstract description 6
- 239000011347 resin Substances 0.000 claims abstract description 6
- 229920005989 resin Polymers 0.000 claims abstract description 6
- 239000012982 microporous membrane Substances 0.000 claims abstract description 5
- 238000001914 filtration Methods 0.000 claims abstract description 4
- 238000001179 sorption measurement Methods 0.000 claims abstract description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 11
- 239000007788 liquid Substances 0.000 claims description 5
- 238000002390 rotary evaporation Methods 0.000 claims description 4
- 239000003463 adsorbent Substances 0.000 claims description 3
- 238000004140 cleaning Methods 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- 210000000582 semen Anatomy 0.000 claims description 3
- 238000007873 sieving Methods 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 2
- 239000011148 porous material Substances 0.000 claims description 2
- 238000010992 reflux Methods 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims 1
- 238000009210 therapy by ultrasound Methods 0.000 claims 1
- 239000000047 product Substances 0.000 abstract description 2
- 241000196324 Embryophyta Species 0.000 description 3
- 238000002137 ultrasound extraction Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 235000017008 Dioscorea nipponica Nutrition 0.000 description 2
- 241000908494 Dioscorea nipponica Species 0.000 description 2
- 235000004360 Dioscorea zingiberensis Nutrition 0.000 description 2
- 241001678283 Dioscorea zingiberensis Species 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 230000001603 reducing effect Effects 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- ADHFZEPOBOTKSO-QLTVFDSQSA-N (1R,2S,4R,5'R,6R,7S,8R,9S,12S,13S)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane]-3-ol Chemical class O([C@@H]1[C@@H]([C@]2(CC[C@@H]3[C@@]4(C)CCCCC4CC[C@H]3[C@@H]2C1O)C)[C@@H]1C)[C@]11CC[C@@H](C)CO1 ADHFZEPOBOTKSO-QLTVFDSQSA-N 0.000 description 1
- INLFWQCRAJUDCR-IQVMEADQSA-N (1R,2S,4S,5'S,6R,7S,8R,9S,12S,13S)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane] Chemical compound O([C@@H]1[C@@H]([C@]2(CC[C@@H]3[C@@]4(C)CCCCC4CC[C@H]3[C@@H]2C1)C)[C@@H]1C)[C@]11CC[C@H](C)CO1 INLFWQCRAJUDCR-IQVMEADQSA-N 0.000 description 1
- 241000220485 Fabaceae Species 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 241000220435 Papilionoideae Species 0.000 description 1
- DWCSNWXARWMZTG-UHFFFAOYSA-N Trigonegenin A Natural products CC1C(C2(CCC3C4(C)CCC(O)C=C4CCC3C2C2)C)C2OC11CCC(C)CO1 DWCSNWXARWMZTG-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- WQLVFSAGQJTQCK-VKROHFNGSA-N diosgenin Chemical compound O([C@@H]1[C@@H]([C@]2(CC[C@@H]3[C@@]4(C)CC[C@H](O)CC4=CC[C@H]3[C@@H]2C1)C)[C@@H]1C)[C@]11CC[C@@H](C)CO1 WQLVFSAGQJTQCK-VKROHFNGSA-N 0.000 description 1
- WQLVFSAGQJTQCK-UHFFFAOYSA-N diosgenin Natural products CC1C(C2(CCC3C4(C)CCC(O)CC4=CCC3C2C2)C)C2OC11CCC(C)CO1 WQLVFSAGQJTQCK-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000005325 percolation Methods 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 230000002633 protecting effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229930182490 saponin Natural products 0.000 description 1
- 150000007949 saponins Chemical class 0.000 description 1
- 235000017709 saponins Nutrition 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
- C07J71/0005—Oxygen-containing hetero ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicines Containing Plant Substances (AREA)
- Steroid Compounds (AREA)
Abstract
The invention discloses a method for extracting dioscin from fenugreek.A method for extracting dioscin from fenug; filtering the effluent with microporous membrane, concentrating the filtrate, and drying to constant weight to obtain dioscin. The method is simple to operate, has high extraction rate compared with other extraction methods, and improves the extraction rate and the product purity by removing impurities with macroporous adsorption resin after petroleum ether, chloroform and ethyl acetate are used for removing impurities.
Description
The invention belongs to the field of extraction of medicinal organic matters, and relates to a method for extracting dioscin.
Background
The semen Trigonellae has anticancer, antioxidant, blood glucose reducing, blood lipid reducing, analgesic, antiinflammatory, and liver and kidney protecting effects.
The fenugreek is an annual herbaceous plant of the genus fenugreek of the subfamily Papilionoideae of the family Leguminosae, the plant has a strong aromatic smell, especially in Gansu and other areas, the content of active ingredients is far higher than that in other areas, and the fenugreek is endowed with a special medicinal value. Saponins are a combination of aglycones and polysaccharides, the sapogenins being mainly in the form of spirostanols (such as diosgenin) and furansterols (protodiosgenin). At present, dioscorea zingiberensis and dioscorea nipponica are the most widely used raw materials for producing dioscin, but the dioscorea zingiberensis and the dioscorea nipponica have long growth periods, can be harvested after 4-7 years, and the fenugreek has an extremely thick growth period as an annual herbaceous plant. The existing extraction process for extracting dioscin from the traditional Chinese medicinal material fenugreek has the problems of low product content, low extraction rate and the like. More chemical reagents are used for chemically synthesizing the dioscin, and no mature process capable of being applied industrially exists at present.
Disclosure of Invention
In view of the problems of the existing dioscin extraction method, the invention improves the extraction route, optimizes the reaction conditions and establishes the dioscin extraction method with high extraction rate on the basis of earlier research work.
The specific implementation method comprises the following steps:
(1) cleaning, drying and crushing fenugreek seeds, and sieving the seeds with a 120-mesh sieve for later use;
(2) adding 70% ethanol solution into semen Trigonellae powder as extraction solvent, and ultrasonically extracting dioscin;
(3) extracting a solid-liquid mixture by reflux extraction, and collecting filtrate;
(4) concentrating the filtrate by rotary evaporation, and removing alcohol from the concentrated solution;
(5) removing impurities from the concentrated solution with petroleum ether, chloroform and ethyl acetate respectively, and passing through macroporous adsorbent resin;
(6) filtering the effluent with microporous membrane, concentrating the filtrate, and drying to constant weight.
The invention has the following positive effects:
(1) the invention directly utilizes ultrasonic wave to extract dioscin and determines the optimal factors. Compared with other extraction schemes, the ultrasonic extraction method has the advantages of high ultrasonic extraction rate and simplicity in operation.
(2) The invention utilizes the rotary evaporation to concentrate the extracting solution, and part of impurities in the extracting solution are evaporated, which is beneficial to improving the purity of the dioscin.
(3) The method utilizes petroleum ether, chloroform and ethyl acetate to remove impurities, and then macroporous adsorption resin is used for adsorption and impurity removal to extract impurities in the constant volume liquid, thereby being beneficial to improving the extraction rate and purity of the dioscin.
Detailed Description
The following examples are further detailed descriptions of the present invention.
Cleaning, drying and crushing fenugreek seeds, and sieving the seeds with a 120-mesh sieve for later use; precisely weighing 5g of fenugreek powder in a flask, and adding 50mL of 70% ethanol solution as an extraction solvent; adding water into the extracting solution for dispersion and percolation; performing rotary evaporation and concentration to remove alcohol; removing impurities from the water solution with petroleum ether, chloroform and ethyl acetate respectively; then passing through macroporous adsorbent resin, washing with water to remove effluent, washing with ethanol solution, and collecting effluent; filtering the effluent with microporous membrane with pore diameter of 0.45 μm, concentrating the filtrate, and drying to constant weight to obtain refined dioscin.
The optimum parameters for ultrasonic extraction of dioscin are that the ratio of material to liquid is 1: 10(g/mL), the pH of the extractant is 8, the ultrasonic temperature is 70 ℃, and the ultrasonic time is 60 min. The extraction rate was 0.82%.
Although the present invention has been described herein with reference to the illustrated embodiments thereof, which are intended to be preferred embodiments of the present invention, it is to be understood that the invention is not limited thereto, and that numerous other modifications and embodiments can be devised by those skilled in the art that will fall within the spirit and scope of the principles of this disclosure.
Claims (7)
1. The method for extracting dioscin from fenugreek comprises the following steps:
(1) cleaning, drying and crushing fenugreek seeds, and sieving the seeds with a 120-mesh sieve for later use;
(2) adding 70% ethanol as extraction solvent into semen Trigonellae powder, and ultrasonic extracting dioscin;
(3) extracting a solid-liquid mixture by reflux extraction, and collecting filtrate;
(4) concentrating the filtrate by rotary evaporation, and removing alcohol from the concentrated solution;
(5) removing impurities from the concentrated solution with petroleum ether, chloroform and ethyl acetate respectively, and passing through macroporous adsorbent resin;
(6) filtering the effluent with microporous membrane, concentrating the filtrate, and drying to constant weight.
2. The method for extracting dioscin from fenugreek according to claim 1, wherein the ultrasonic feed-liquid ratio in the step (2) is 1: 10.
3. The method for extracting dioscin from fenugreek according to claim 1, wherein the pH of the extractant in step (2) is 8.
4. The method for extracting dioscin from fenugreek according to claim 1, wherein the ultrasonic temperature in the step (2) is 70 ℃.
5. The method for extracting dioscin from fenugreek according to claim 1, wherein the ultrasonic treatment in step (2) is performed for 60 min.
6. The method for extracting dioscin from fenugreek according to claim 1, wherein petroleum ether, chloroform and ethyl acetate are added in the step (5) to remove impurities, and then macroporous adsorption resin separation is carried out to improve the extraction rate and purity of dioscin.
7. The method for extracting dioscin from fenugreek according to claim 1, wherein the pore size of the microporous membrane in the step (6) is 0.45 μm.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202010900562.7A CN111978366A (en) | 2020-09-01 | 2020-09-01 | Method for extracting dioscin from fenugreek |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202010900562.7A CN111978366A (en) | 2020-09-01 | 2020-09-01 | Method for extracting dioscin from fenugreek |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN111978366A true CN111978366A (en) | 2020-11-24 |
Family
ID=73448315
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202010900562.7A Pending CN111978366A (en) | 2020-09-01 | 2020-09-01 | Method for extracting dioscin from fenugreek |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN111978366A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113387998A (en) * | 2021-07-19 | 2021-09-14 | 青海师范大学 | Preparation method of dioscin in fenugreek |
-
2020
- 2020-09-01 CN CN202010900562.7A patent/CN111978366A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113387998A (en) * | 2021-07-19 | 2021-09-14 | 青海师范大学 | Preparation method of dioscin in fenugreek |
| CN113387998B (en) * | 2021-07-19 | 2022-03-29 | 青海师范大学 | Preparation method of dioscin in fenugreek |
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| Date | Code | Title | Description |
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| PB01 | Publication | ||
| PB01 | Publication | ||
| WD01 | Invention patent application deemed withdrawn after publication | ||
| WD01 | Invention patent application deemed withdrawn after publication |
Application publication date: 20201124 |