CN101974009B - Process for separating imperatorin from osthole extract waste liquid - Google Patents
Process for separating imperatorin from osthole extract waste liquid Download PDFInfo
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- CN101974009B CN101974009B CN201010531934XA CN201010531934A CN101974009B CN 101974009 B CN101974009 B CN 101974009B CN 201010531934X A CN201010531934X A CN 201010531934XA CN 201010531934 A CN201010531934 A CN 201010531934A CN 101974009 B CN101974009 B CN 101974009B
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- CN
- China
- Prior art keywords
- osthole
- solvent
- crystallization
- imperatorin
- pentosalen
- Prior art date
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- MBRLOUHOWLUMFF-UHFFFAOYSA-N osthole Chemical compound C1=CC(=O)OC2=C(CC=C(C)C)C(OC)=CC=C21 MBRLOUHOWLUMFF-UHFFFAOYSA-N 0.000 title claims abstract description 23
- HPUXDMUGCAWDFW-UHFFFAOYSA-N Osthole Natural products COc1ccc2CCC(=O)Oc2c1C=CC(=O)C HPUXDMUGCAWDFW-UHFFFAOYSA-N 0.000 title claims abstract description 22
- OLOOJGVNMBJLLR-UHFFFAOYSA-N imperatorin Chemical compound C1=CC(=O)OC2=C1C=C1C=COC1=C2OCC=C(C)C OLOOJGVNMBJLLR-UHFFFAOYSA-N 0.000 title claims abstract description 21
- 239000007788 liquid Substances 0.000 title claims abstract description 17
- 239000000284 extract Substances 0.000 title claims abstract description 12
- 238000000034 method Methods 0.000 title claims abstract description 8
- 239000002699 waste material Substances 0.000 title claims abstract description 7
- XKVWLLRDBHAWBL-UHFFFAOYSA-N imperatorin Natural products CC(=CCOc1c2OCCc2cc3C=CC(=O)Oc13)C XKVWLLRDBHAWBL-UHFFFAOYSA-N 0.000 title abstract 5
- 239000002904 solvent Substances 0.000 claims abstract description 10
- 239000000843 powder Substances 0.000 claims abstract description 6
- 238000001914 filtration Methods 0.000 claims abstract description 5
- 238000010438 heat treatment Methods 0.000 claims abstract description 4
- 239000003513 alkali Substances 0.000 claims abstract description 3
- 238000000638 solvent extraction Methods 0.000 claims abstract description 3
- 238000002425 crystallisation Methods 0.000 claims description 17
- 230000008025 crystallization Effects 0.000 claims description 17
- 239000002994 raw material Substances 0.000 claims description 14
- 238000000605 extraction Methods 0.000 claims description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- 239000006228 supernatant Substances 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- 238000001953 recrystallisation Methods 0.000 claims description 6
- 239000012141 concentrate Substances 0.000 claims description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- 230000008021 deposition Effects 0.000 claims description 4
- 239000011259 mixed solution Substances 0.000 claims description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 230000008719 thickening Effects 0.000 claims description 2
- 235000013399 edible fruits Nutrition 0.000 abstract description 3
- 238000000926 separation method Methods 0.000 abstract description 3
- 239000000706 filtrate Substances 0.000 abstract description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- 239000002244 precipitate Substances 0.000 abstract description 2
- 238000002360 preparation method Methods 0.000 abstract description 2
- 239000000047 product Substances 0.000 abstract description 2
- 238000000746 purification Methods 0.000 abstract description 2
- 239000000463 material Substances 0.000 abstract 4
- 241000212948 Cnidium Species 0.000 abstract 2
- 239000013078 crystal Substances 0.000 abstract 2
- 238000003756 stirring Methods 0.000 abstract 1
- 238000005516 engineering process Methods 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
- 235000019441 ethanol Nutrition 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- YRAQEMCYCSSHJG-NSHDSACASA-N (S)-columbianetin Chemical compound C1=CC(=O)OC2=C1C=CC1=C2C[C@@H](C(C)(O)C)O1 YRAQEMCYCSSHJG-NSHDSACASA-N 0.000 description 2
- RNKZFOIQKCQOAQ-UHFFFAOYSA-N Isopimpinellin Natural products COC1CC(=O)Oc2c(OC)c3occc3cc12 RNKZFOIQKCQOAQ-UHFFFAOYSA-N 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
- 235000019634 flavors Nutrition 0.000 description 2
- DFMAXQKDIGCMTL-UHFFFAOYSA-N isopimpinellin Chemical compound O1C(=O)C=CC2=C1C(OC)=C1OC=CC1=C2OC DFMAXQKDIGCMTL-UHFFFAOYSA-N 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 1
- XYHKNCXZYYTLRG-UHFFFAOYSA-N 1h-imidazole-2-carbaldehyde Chemical compound O=CC1=NC=CN1 XYHKNCXZYYTLRG-UHFFFAOYSA-N 0.000 description 1
- JBQHVGSHZLWWDC-AWEZNQCLSA-N 2-[(8S)-2-oxo-8,9-dihydrofuro[2,3-h]chromen-8-yl]propan-2-yl 2-methylpropanoate Chemical compound CC(C)C(=O)OC(C)(C)[C@@H]1Cc2c(O1)ccc1ccc(=O)oc21 JBQHVGSHZLWWDC-AWEZNQCLSA-N 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-M 3-Methylbutanoic acid Natural products CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 description 1
- JBQHVGSHZLWWDC-UHFFFAOYSA-N Cnidiadin Natural products C1=CC(=O)OC2=C1C=CC1=C2CC(C(C)(C)OC(=O)C(C)C)O1 JBQHVGSHZLWWDC-UHFFFAOYSA-N 0.000 description 1
- 240000009087 Crescentia cujete Species 0.000 description 1
- 235000005983 Crescentia cujete Nutrition 0.000 description 1
- 241000125183 Crithmum maritimum Species 0.000 description 1
- 244000000626 Daucus carota Species 0.000 description 1
- 235000002767 Daucus carota Nutrition 0.000 description 1
- 201000004624 Dermatitis Diseases 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 240000006927 Foeniculum vulgare Species 0.000 description 1
- 235000004204 Foeniculum vulgare Nutrition 0.000 description 1
- 235000009797 Lagenaria vulgaris Nutrition 0.000 description 1
- 235000007413 Nigella arvensis Nutrition 0.000 description 1
- 235000008750 Nigella damascena Nutrition 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 208000008350 Pruritus Vulvae Diseases 0.000 description 1
- 244000296102 Selinum monnieri Species 0.000 description 1
- 241000270295 Serpentes Species 0.000 description 1
- YRAQEMCYCSSHJG-UHFFFAOYSA-N Tetrahydro-oroselol Natural products C1=CC(=O)OC2=C1C=CC1=C2CC(C(C)(O)C)O1 YRAQEMCYCSSHJG-UHFFFAOYSA-N 0.000 description 1
- 206010056530 Vulvovaginal pruritus Diseases 0.000 description 1
- 206010047799 Vulvovaginitis trichomonal Diseases 0.000 description 1
- KGEKLUUHTZCSIP-HOSYDEDBSA-N [(1s,4s,6r)-1,7,7-trimethyl-6-bicyclo[2.2.1]heptanyl] acetate Chemical compound C1C[C@]2(C)[C@H](OC(=O)C)C[C@H]1C2(C)C KGEKLUUHTZCSIP-HOSYDEDBSA-N 0.000 description 1
- 206010003246 arthritis Diseases 0.000 description 1
- -1 bergapton (berapten) Chemical compound 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N beta-methyl-butyric acid Natural products CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
- DQISGWRLCDLKJI-UHFFFAOYSA-N columbianetin Natural products C1=CC(=O)OC2=C(C(C(C(C)(O)C)O3)O)C3=CC=C21 DQISGWRLCDLKJI-UHFFFAOYSA-N 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 230000004345 fruit ripening Effects 0.000 description 1
- 201000001881 impotence Diseases 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Abstract
The invention discloses a method for separating imperatorin from an osthole extract waste liquid, which comprises the following steps: (1) material preparation: crushing cnidium fruit materials into powder of 20 meshes; (2) solvent extraction: adding a solvent in the materials, stirring and extracting while heating, and removing decoction dregs; (3) concentration: concentrating while depressurizing to obtain a mixed liquid of osthole and imperatorin; (4) separation: standing the mixed liquid until the mixed liquid is stratified, removing the supernate for later use, and crystallizing the precipitate with alkali liquids of different concentrations to obtain osthole crystals, merging the filtrate with the obtained supernate, adjusting the pH value to 7-8, extracting with a solvent, concentrating, and standing at low temperature to crystallize out crude imperatorin products; and (5) purification: heating to dissolve the crystals in a small amount of solvent, filtering, recrystallizing at low temperature. The invention thoroughly improves the utility value of the cnidium fruit materials, can simultaneously produce high osthole and high-content imperatorin and has the advantages of simple process, low production cost and high yield.
Description
Technical field
The present invention relates to field of plant extraction, be specifically related to the extracting and purifying method of pentosalen.
Background technology
Fructus Cnidii is snake rice, Daucus carota L., wild fennel again, is the dry mature fruit of samphire cnidium monnieri Cnidiummonnieri (L.) Cuss..This thing is born in the ground of humidities such as field, river bank, roadside, and all there is distribution all parts of the country.Autumn in summer gathers during fruit maturation, dries subsequent use.Nature and flavor: warm in nature, flavor is hot, bitter.Function cures mainly: warming the kidney to invigorate YANG, eliminating dampness is dispeled the wind, desinsection.Be used for that impotence, palace are cold, under the cold-dampness band, the arthritis with fixed pain caused by dampness pain in the back; Control vulval eczema, married woman's pruritus vulvae, trichomonal vaginitis outward.Contain firpene, isovaleric acid borneol acetate (bornyl isovalarate), osthole (osthol), Columbianetin, bergapton (berapten), osthole (cnidiadin), isopimpinellin effective constituents such as (isopimpinellin) in the Fructus Cnidii.
Summary of the invention
The objective of the invention is to provide a kind of and extract the technology of separating pentosalen the waste liquid from osthole.
Technical solution of the present invention, a kind of technology of from osthole extraction waste liquid, separating pentosalen may further comprise the steps successively:
(1) gets the raw materials ready: the Fructus Cnidii raw material powder is broken into 20 purpose powder;
(2) solvent extraction: in raw material, add solvent, heated and stirred is extracted, and removes the dregs of a decoction after accomplishing;
(3) concentrate: concentrating under reduced pressure, the mixed solution of acquisition osthole and pentosalen;
(4) separate: behind the mixed solution standing demix, it is subsequent use to remove supernatant, and deposition obtains the osthole crystallization with the alkali lye crystallization; Filtrating and the supernatant that obtains are before merged; Transfer pH to 7～8, use SX then, concentrated, stand at low temperature crystallization goes out the pentosalen bullion;
(5) purifying:, put the low temperature recrystallization with little solvent heating for dissolving crystallization and filtration.
Wherein, the solvent that adds in the above-mentioned steps (2) is 60%～80% methyl alcohol preferably, and consumption is 6～8 times of raw material preferably, and extraction time is preferably each 1.5h, and extraction time is preferably 3～4 times, extracts temperature and is preferably 60～80 ℃.
In the above-mentioned steps (3) thickening temperature be preferably≤55 ℃.
Extraction preferably uses sherwood oil or normal hexane to be the water layer extraction agent in the above-mentioned steps (4); Long-pending Deng water liquid; Extract 3～4 times, petroleum ether layer or normal hexane layer are condensed into medicinal extract, with 5～10 times of 98% dissolve with ethanol crystallization; The water liquid that gets after the osthole bullion extracts leaves standstill more than the 48h for 4 ℃, goes out the bullion pentosalen.
In the above-mentioned said step (5), recrystallization solvent is preferably 98% ethanol, after 5～10 times of calorimetrics dissolving, contracts to less than 5 times of volumes, and 4 ℃ leave standstill crystallization.
This technology has following advantage:
1, fully improves the utility value of Fructus Cnidii raw material: when producing high osthole,, produce high-load pentosalen through the simple separation step;
2, technological process is simple, and production cost is low: utilize the waste liquid of producing in the osthole process, through regulating easy steps such as PH, SX, isolating to pentosalen, the cost of osthole and pentosalen all reduces greatly;
3, yield is high: this technology is produced 98% pentosalen when producing 98% osthole, and calabash have the effect composition recovery and can reach more than 80% in the Europe before.
Description of drawings
Fig. 1 is a process flow sheet of the present invention.
Embodiment
Below in conjunction with specific embodiment the present invention is described further, but the present invention is not limited to following examples.
Embodiment 1
The preparation process:
1, pulverize: (125kg) is ground into the powder about 20 orders with the Fructus Cnidii raw material, and the too big extraction of raw material is incomplete, and the too little residue of raw material is difficult for filtering to be removed.
2, extract, concentrate: 750L80% methyl alcohol is poured in the extractor; 80 ℃ are stirred extraction 1.5h; Residue is carried 2 times with same amount again, merging filtrate, and 55 ℃ are evaporated to raw material is 1: 1～1: 1.5 (short period of time concentrates as far as possible) with concentrating back solution quality ratio.
3, separation and purification: liquid concentrator is left standstill 1～2h, and it is subsequent use to remove supernatant, will precipitate to regulate NaOH concentration to 0.5%～1%; Low temperature (4 ℃) leaves standstill crystallization and filtration and goes out crystallization (be osthole, aftertreatment such as recrystallization is carried out in crystallization can go out 98% finished product osthole), collects filtrating; Merge with supernatant, regulating that PH is evaporated to raw material and concentrates back solution quality ratio to the neutrality is 1: 1～1: 1.5, is placed to deposition and removes supernatant after fully; Wait the sherwood oil of supernatant volume to extract deposition usefulness, extract 3～4 times, collect the water liquid that has extracted; Low temperature (4 ℃) is placed the above crystallization of 48h after being concentrated into half volume; Filter out after the crystallization with 5～10 times of calorimetric ethyl alcohol recrystallizations, get final product the pentosalen about 1kg, be 98% through detection level.
Claims (1)
1. one kind is extracted the method for separating pentosalen the waste liquid from osthole, it is characterized in that: comprise following step:
(1) gets the raw materials ready: the Fructus Cnidii raw material powder is broken into 20 purpose powder;
(2) solvent extraction: in raw material, add 60%～80% methyl alcohol, heated and stirred is extracted, and accomplishes the back removal dregs of a decoction;
(3) concentrate: concentrating under reduced pressure, the mixed solution of acquisition osthole and pentosalen;
(4) separate: behind the mixed solution standing demix, it is subsequent use to remove supernatant, and deposition obtains the osthole crystallization with the alkali lye crystallization; Filtrating and the supernatant that obtains are before merged; Transfer pH to 7～8, use SX then, concentrated, stand at low temperature crystallization goes out the pentosalen bullion;
(5) purifying:, put the low temperature recrystallization with little solvent heating for dissolving crystallization and filtration;
The middle adding of said step (2) quantity of solvent is 6～8 times of raw materials quality;
It is 60～80 ℃ that said step (2) is extracted temperature;
Said step (2) extraction time is each 1.5h, extracts 3～4 times;
Said step (3) thickening temperature≤55 ℃;
Extraction uses sherwood oil or normal hexane to be the water layer extraction agent in the said step (4), waits water liquid long-pending, extracts 3～4 times;
Said step (4) PetroChina Company Limited.'s ether layer or normal hexane layer are condensed into medicinal extract, with 5～10 times of 98% dissolve with ethanol crystallization, get the osthole bullion;
Water liquid in the said step (4) after the extraction leaves standstill more than the 48h for 4 ℃, goes out the bullion pentosalen;
In the said step (5), recrystallization solvent is 98% ethanol, after 5～10 times of calorimetrics dissolving, contracts to less than 5 times of volumes, and 4 ℃ leave standstill crystallization.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201010531934XA CN101974009B (en) | 2010-11-03 | 2010-11-03 | Process for separating imperatorin from osthole extract waste liquid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201010531934XA CN101974009B (en) | 2010-11-03 | 2010-11-03 | Process for separating imperatorin from osthole extract waste liquid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN101974009A CN101974009A (en) | 2011-02-16 |
| CN101974009B true CN101974009B (en) | 2012-04-11 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201010531934XA Active CN101974009B (en) | 2010-11-03 | 2010-11-03 | Process for separating imperatorin from osthole extract waste liquid |
Country Status (1)
| Country | Link |
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| CN (1) | CN101974009B (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104844550B (en) * | 2015-04-16 | 2017-04-05 | 聊城大学 | A kind of method that osthole and imperatorin are isolated and purified from Fructus Cnidii |
| CN105131007A (en) * | 2015-09-08 | 2015-12-09 | 聊城大学 | Method for extracting, separating and purifying imperatorin and cnidium lactone from fructus cnidii |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1275969C (en) * | 2002-03-14 | 2006-09-20 | 北京同源医药科技有限公司 | Application of active ingredient of coumarin category distilled from dahurian angelica in preparing medicine for curing high blood pressure and its extracting method |
| US20050220913A1 (en) * | 2004-03-31 | 2005-10-06 | Council Of Scientific And Industrial Research | Novel in-expensive and efficient process for isolation of imperatorin, a potent inducible nitric oxide synthase inhibitor and anti-inflammatory drug candidate from Aegle marmelos Correa |
| CN100386327C (en) * | 2006-06-19 | 2008-05-07 | 西安交通大学 | Method for picking-up effective ingredient of Imperatorin of Chinese traditional medicine cnidium fruit, and element of cnidium fruit |
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- 2010-11-03 CN CN201010531934XA patent/CN101974009B/en active Active
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| Publication number | Publication date |
|---|---|
| CN101974009A (en) | 2011-02-16 |
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Address after: 710077 entrepreneurship research and Development Park, No. 69 Kam Yip Road, Shaanxi, Xi'an C601 Patentee after: XI'AN APP-CHEM BIO(TECH) Co.,Ltd. Address before: 710077 entrepreneurship research and Development Park, No. 69 Kam Yip Road, Shaanxi, Xi'an C601 Patentee before: XI AN APP CHEM BIO TECH Co.,Ltd. |
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Denomination of invention: Process for separating imperatorin from osthole extract waste liquid Effective date of registration: 20170401 Granted publication date: 20120411 Pledgee: Industrial Bank Limited by Share Ltd. Xi'an branch Pledgor: XI'AN APP-CHEM BIO(TECH) Co.,Ltd. Registration number: 2017610000020 |
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Date of cancellation: 20180706 Granted publication date: 20120411 Pledgee: Industrial Bank Limited by Share Ltd. Xi'an branch Pledgor: XI'AN APP-CHEM BIO(TECH) Co.,Ltd. Registration number: 2017610000020 |
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Denomination of invention: Process for separating imperatorin from osthole extract waste liquid Effective date of registration: 20180711 Granted publication date: 20120411 Pledgee: Industrial Bank Limited by Share Ltd. Xi'an branch Pledgor: XI'AN APP-CHEM BIO(TECH) Co.,Ltd. Registration number: 2018610000103 |
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Date of cancellation: 20220829 Granted publication date: 20120411 Pledgee: Industrial Bank Limited by Share Ltd. Xi'an branch Pledgor: XI'AN APP-CHEM BIO(TECH) Co.,Ltd. Registration number: 2018610000103 |