CN1071663A - A kind of extracting method of coixenolide - Google Patents
A kind of extracting method of coixenolide Download PDFInfo
- Publication number
- CN1071663A CN1071663A CN 91106269 CN91106269A CN1071663A CN 1071663 A CN1071663 A CN 1071663A CN 91106269 CN91106269 CN 91106269 CN 91106269 A CN91106269 A CN 91106269A CN 1071663 A CN1071663 A CN 1071663A
- Authority
- CN
- China
- Prior art keywords
- coixenolide
- alkali
- alumina
- semen coicis
- acetone
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 238000000034 method Methods 0.000 title claims abstract description 23
- DPQCZNIGGNJGTD-UHFFFAOYSA-N Chloride-(??)-2-Methylpentanoic acid Natural products CCCCCCC=CCCCCCCCCCC(=O)OC(C)C(C)OC(=O)CCCCCCCC=CCCCCCC DPQCZNIGGNJGTD-UHFFFAOYSA-N 0.000 title claims abstract description 19
- DPQCZNIGGNJGTD-MVCBGFDASA-N Coixenolide Chemical compound CCCCCC\C=C\CCCCCCCCCC(=O)O[C@@H](C)[C@@H](C)OC(=O)CCCCCCC\C=C/CCCCCC DPQCZNIGGNJGTD-MVCBGFDASA-N 0.000 title claims abstract description 19
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 38
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims abstract description 24
- 239000003513 alkali Substances 0.000 claims abstract description 19
- 238000004587 chromatography analysis Methods 0.000 claims abstract description 17
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000002994 raw material Substances 0.000 claims abstract description 9
- 239000002594 sorbent Substances 0.000 claims abstract description 7
- 229910021529 ammonia Inorganic materials 0.000 claims abstract description 5
- 238000010992 reflux Methods 0.000 claims abstract description 5
- 210000000582 semen Anatomy 0.000 claims description 19
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 12
- 239000000284 extract Substances 0.000 claims description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 8
- 238000000605 extraction Methods 0.000 claims description 6
- 238000000746 purification Methods 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 4
- 239000000741 silica gel Substances 0.000 claims description 4
- 229910002027 silica gel Inorganic materials 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 238000000926 separation method Methods 0.000 claims description 3
- 238000000638 solvent extraction Methods 0.000 claims description 3
- 238000005516 engineering process Methods 0.000 abstract description 12
- 239000002904 solvent Substances 0.000 abstract description 11
- 238000004519 manufacturing process Methods 0.000 abstract description 7
- ZPLCXHWYPWVJDL-UHFFFAOYSA-N 4-[(4-hydroxyphenyl)methyl]-1,3-oxazolidin-2-one Chemical compound C1=CC(O)=CC=C1CC1NC(=O)OC1 ZPLCXHWYPWVJDL-UHFFFAOYSA-N 0.000 abstract description 4
- 238000004140 cleaning Methods 0.000 abstract description 4
- 230000000694 effects Effects 0.000 abstract description 3
- 238000009776 industrial production Methods 0.000 abstract description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
- 238000004821 distillation Methods 0.000 description 8
- 238000011010 flushing procedure Methods 0.000 description 6
- 239000003480 eluent Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 239000006188 syrup Substances 0.000 description 5
- 235000020357 syrup Nutrition 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- 238000010898 silica gel chromatography Methods 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 238000001179 sorption measurement Methods 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 3
- 238000004945 emulsification Methods 0.000 description 3
- 238000003672 processing method Methods 0.000 description 3
- 239000012670 alkaline solution Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 201000009030 Carcinoma Diseases 0.000 description 1
- 241000209205 Coix Species 0.000 description 1
- 244000077995 Coix lacryma jobi Species 0.000 description 1
- 235000007354 Coix lacryma jobi Nutrition 0.000 description 1
- 206010010904 Convulsion Diseases 0.000 description 1
- 208000004880 Polyuria Diseases 0.000 description 1
- 208000000260 Warts Diseases 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 230000036461 convulsion Effects 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000035619 diuresis Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 201000010153 skin papilloma Diseases 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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- Extraction Or Liquid Replacement (AREA)
- Treatment Of Liquids With Adsorbents In General (AREA)
- Medicines Containing Plant Substances (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
A kind of extracting method of coixenolide is characterized in that it being to adopt apparatus,Soxhlet's, with acetone solvent to the raw material extracting that refluxes.When carrying out the chromatography column separating treatment, adopt the alkali alumina sorbent material chromatography post of alkali or ammonia treatment simultaneously.This technology is compared with the technology of present employing, and it is few to extract the solvent acetone consumption, handles alumina adsorbant without alkali cleaning and with the bromothymol blue indicator.Its technological process is short, and is simple and easy to do, good separating effect, and the yield Gao Keda 0.6% of product, and can reduce by a relatively large margin and manufacture a finished product, therefore be suitable in industrial production, using.
Description
The present invention relates to a kind of preparation method who utilizes abstraction technique from Semen Coicis, to extract coixenolide.
Semen Coicis is a kind of ancient Chinese medicine, diuresis is arranged, be good for the stomach, separate and take out convulsion and remove biological activity such as wart.Find the acetone extract of Semen Coicis at the beginning of 60, can suppress the growth of mouse body ehrlich carcinoma cell, thereby by the coixenolide of wherein isolating anticancer effective component.Because coixenolide has antitumour activity, its extracting method and applied research all there is report, for example Japanese Patent is openly speciallyyed permit clear 58-213719 to provide a kind of is that raw material acetone is the method for solvent extraction coixenolide with the Semen Coicis.The technology that extensively adopts mainly comprises the steps: at present
1, with dry coix seed powder, multiple extraction with acetone under room temperature, extracting solution is through concentrating under reduced pressure, again through sherwood oil purify the reddish-brown syrup; 2, get extract and be dissolved in sherwood oil, use the silica gel adsorption column chromatography; 3, products therefrom obtains being insoluble to the neutrals of alkali with potassium hydroxide aqueous solution flush away acid; 4, at first handle aluminum oxide, make the alumina adsorption post, the more above-mentioned neutral products that is insoluble to alkali that obtains is separated by alumina chromatographic column with the chloroformic solution of 10% bromothymol blue, with chloroform wash all present yellow to alumina column till; 5, again 4 isolating neutralss are carried out leafing by silica gel adsorption column at last and make the finished product coixenolide.Though relatively letter example of above-mentioned present employing technology processing method is row easily, still has some technical problems, makes in industrial application to remain in certain difficulty.This is mainly: 1, use a large amount of acetone solvent (the 2Kg raw material needs 15L acetone), so the solvent treatment difficulty, expanding the scale of production is subjected to certain restriction; 2, utilize the very easily emulsification of alkaline solution washing operation, therefore make to separate to be difficult to carry out; 3, aluminum oxide needs to handle with bromothymol blue, and wants a large amount of chloroforms of loss, increases manufacturing cost.4, product yield is low only be raw material 0.2% on the right side.
The purpose of this invention is to provide the easy preparation coixenolide process for extracting of a kind of technology, to adapt to the suitability for industrialized production needs.
The present invention is on the basis of former Job's tears extractive technique, use quantity of solvent big at it, carry out main drawbacks such as easy emulsification of alkali cleaning and alumina chromatographic column preparation cost height, carried out that bigger technological improvement has proposed a kind of letter and the easy processing method that adopts of the suitable industrialization of row.This process flow diagram as shown in Figure 1.In accompanying drawing 1,1, the acetone extract Semen Coicis; 2, separate, reclaim solvent; 3, sherwood oil separation and purification Semen Coicis oil; 4, separate, reclaim sherwood oil; 5, sherwood oil flushing silica gel column chromatography; 6, separate, reclaim sherwood oil; 7, chloroform flushing alumina chromatographic column; 8, separate, reclaim chloroform; 9, product.Comprise with acetone being solvent extraction Semen Coicis 1 by the coixenolide preparation technology of the present invention shown in the accompanying drawing 1, carry out separation and purification Semen Coicis oil 3 with sherwood oil, Semen Coicis oil is carried out silica gel column chromatography separating treatment 5 and carry out the alumina column chromatography separating treatment with the chloroform flushing obtaining 7 and obtaining the product coixenolide with sherwood oil flushing.This technology is characterised in that the extracting that refluxes of operation 1 acetone extract Semen Coicis in apparatus,Soxhlet's, the usage quantity of solvent acetone can be reduced significantly, is 1/4～1/5 of common extracting process only.Save the trouble of handling a large amount of solvents like this, reduced unsafe factor; Operation 7 used chromatography column sorbent material aluminum oxide give processing with alkali or ammonia soln earlier, make the alkali alumina sorbent material and make chromatography column again, not only aluminum oxide needn't be handled with the bromothymol blue indicator again, reduce complicated treating processes, save a large amount of chloroform solvents and prepare indicator, and can save among the common preparation technology and carry out alkaline cleaning procedure with potassium hydroxide, avoid the easy emulsification of alkaline cleaning procedure effectively and not segregative technical problem, the purification thing can be directly as product behind the alkali alumina adsorpting column chromatography.The products therefrom yield also improves 3～5 times than former technology.Above-mentioned alkaline solution is handled alumina process and can be adopted sodium hydroxide or potassium hydroxide aqueous solution to carry out, and also can replace aluminum oxide to make sorbent material with gac, is directly used in chromatography column and separates.Raw material can directly utilize exsiccant Semen Coicis kind benevolence in this external above-mentioned technology, and will not pulverize by raw material, has both reduced operation and equipment, also reduces the loss of raw material, reduces production costs.Specifically, technological process of the present invention is as follows.
Exsiccant Semen Coicis kind benevolence is directly placed apparatus,Soxhlet's, and with the acetone extracting that refluxes, the extracting time should be no less than 10 hours to guarantee that coixenolide is fully extracted.Extracting solution reclaims acetone through (decompression) distillation can be re-used as the solvent use, and obtains thick Semen Coicis oil; Thick product adds sherwood oil and leaches insolubles, reclaims sherwood oil subsequently and gets Semen Coicis oil; Get extract and be dissolved in sherwood oil, be added to silica gel column chromatography, make eluent flushing silica gel column chromatography with sherwood oil, distillation is reclaimed eluent and is got the yellow oily extract; Utilize alkali or ammonia soln to give to handle aluminum oxide to make the alkali alumina sorbent material and make chromatography column, the yellow oily extract is dissolved in chloroform, be added in alkali alumina or the activated carbon chromatography post, wash chromatography column with chloroform as eluent, distillation recovery eluent obtains light yellow neutral oily matter and is the product coixenolide, and its yield can reach 0.6%.Give further instruction below by example to technology of the present invention.
The extraction 1 of example 1 coixenolide
Exsiccant Semen Coicis kind benevolence is placed apparatus,Soxhlet's for 2 kilograms, add the backflow of acetone 2.5 liters and extract 14 hours, acetone distillation (but underpressure distillation) is reclaimed, and gets reddish-brown syrup about 70 and restrains.Add sherwood oil 450ml in extracting syrup, separate and remove petroleum ether insoluble, distillation is reclaimed sherwood oil and is got reddish-brown syrup 50 grams.The a small amount of petroleum ether dissolution of last 50 gram syrup, adorn 150 in being added to and restrain on the silica gel adsorption columns, with the flushing of 500ml sherwood oil, distillation gets yellow oil 35 grams after reclaiming the eluent sherwood oil.With 0.5N aqueous sodium hydroxide solution impregnated alumina, dipping back is dry do alkali alumina sorbent material and dress up alumina chromatographic column.Above-mentioned 35 gram yellow oily extracts are added adorn in the 500 gram alkali alumina chromatography columns in being added to after the minimum of chloroform dissolving, with chloroform wash present yellow to the alumina column bottom till.Distillation is reclaimed behind the chloroform must the light yellow neutral oily matter of about 12 grams, is the coixenolide product, and product yield can reach 0.6%.
The extraction 2 of example 2 coixenolides
With 10% ammonia treatment aluminum oxide and make the alkali alumina chromatography column.Adopt 600 grams to contain the chromatography column of above-mentioned alkali alumina, handle the 35 gram yellow oil that example 1 described method obtains, can get 11 gram coixenolide products, product yield is 0.55%.
Example 3, the extraction 3 of coixenolide
Make chromatography column with 200 gram gacs.Handle the 35 gram yellow oil that example 1 described method obtains, can get 12 gram coixenolides, product yield is 0.6%.
By above-mentioned example, adopt extraction process of the present invention its method is simple, the consumption of solvent acetone is few in the abstraction process, tool other each step is all realized chromatographyization, good separating effect.In addition, this technology is saved caustic wash process, directly uses alkali alumina (Al
2O
3) chromatography column reaches depickling, the purpose of chromatography has shortened technological process, improves the yield of product.Simultaneously can adopt dry Semen Coicis kind benevolence directly to carry out abstraction reaction, reduce production unit, improve the raw material rate of utilization, and can reduce by a relatively large margin and manufacture a finished product.Therefore processing method of the present invention is suitable for using in industrial production.
Claims (3)
1, a kind of extracting method of coixenolide, comprise with acetone being the solvent extraction Semen Coicis, carry out separation and purification and adopt silica gel and operations such as alumina chromatographic column separates with sherwood oil, it is characterized in that the acetone extract Semen Coicis carries out refluxing extraction in apparatus,Soxhlet's; The sorbent material aluminum oxide that carries out the alumina chromatographic column separating treatment adopts earlier to give handling with alkali or ammonia soln and makes alkali alumina and make chromatography column again; So-called alkaline purification can adopt sodium hydroxide or potassium hydroxide aqueous solution to carry out.
2, according to the described extracting method of claim 1, it is characterized in that chromatography column is handled can to adopt in the activated carbon chromatography post carries out.
3, according to the described extracting method of claim 1, it is characterized in that the acetone extract Semen Coicis should reflux extracting more than 10 hours, gone out by abundant extracting to guarantee the coixenolide in the raw material.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 91106269 CN1031261C (en) | 1991-10-21 | 1991-10-21 | Method for extracting coixenolide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 91106269 CN1031261C (en) | 1991-10-21 | 1991-10-21 | Method for extracting coixenolide |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1071663A true CN1071663A (en) | 1993-05-05 |
| CN1031261C CN1031261C (en) | 1996-03-13 |
Family
ID=4907703
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 91106269 Expired - Fee Related CN1031261C (en) | 1991-10-21 | 1991-10-21 | Method for extracting coixenolide |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN1031261C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004028549A1 (en) * | 2002-09-28 | 2004-04-08 | Dapeng Li | A coixenolide capsules for treating prostate disease |
-
1991
- 1991-10-21 CN CN 91106269 patent/CN1031261C/en not_active Expired - Fee Related
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004028549A1 (en) * | 2002-09-28 | 2004-04-08 | Dapeng Li | A coixenolide capsules for treating prostate disease |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1031261C (en) | 1996-03-13 |
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| C14 | Grant of patent or utility model | ||
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