CN1769279A - Method for extracting and separating isoflavone from kudzu slag - Google Patents
Method for extracting and separating isoflavone from kudzu slag Download PDFInfo
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- CN1769279A CN1769279A CN 200410067728 CN200410067728A CN1769279A CN 1769279 A CN1769279 A CN 1769279A CN 200410067728 CN200410067728 CN 200410067728 CN 200410067728 A CN200410067728 A CN 200410067728A CN 1769279 A CN1769279 A CN 1769279A
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- extraction
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- pueraria lobota
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- isoflavones
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- CJWQYWQDLBZGPD-UHFFFAOYSA-N isoflavone Natural products C1=C(OC)C(OC)=CC(OC)=C1C1=COC2=C(C=CC(C)(C)O3)C3=C(OC)C=C2C1=O CJWQYWQDLBZGPD-UHFFFAOYSA-N 0.000 title claims abstract description 36
- 235000008696 isoflavones Nutrition 0.000 title claims abstract description 36
- 239000002893 slag Substances 0.000 title claims abstract description 31
- GOMNOOKGLZYEJT-UHFFFAOYSA-N isoflavone Chemical compound C=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC=C1 GOMNOOKGLZYEJT-UHFFFAOYSA-N 0.000 title claims description 21
- 238000000034 method Methods 0.000 title abstract description 11
- 235000010575 Pueraria lobata Nutrition 0.000 title abstract description 10
- 241000219781 Pueraria montana var. lobata Species 0.000 title description 8
- 238000000605 extraction Methods 0.000 claims abstract description 61
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 45
- RXUWDKBZZLIASQ-UHFFFAOYSA-N Puerarin Natural products OCC1OC(Oc2c(O)cc(O)c3C(=O)C(=COc23)c4ccc(O)cc4)C(O)C(O)C1O RXUWDKBZZLIASQ-UHFFFAOYSA-N 0.000 claims abstract description 29
- HKEAFJYKMMKDOR-VPRICQMDSA-N puerarin Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1C1=C(O)C=CC(C2=O)=C1OC=C2C1=CC=C(O)C=C1 HKEAFJYKMMKDOR-VPRICQMDSA-N 0.000 claims abstract description 29
- 239000000284 extract Substances 0.000 claims abstract description 28
- 239000007788 liquid Substances 0.000 claims abstract description 28
- 150000002515 isoflavone derivatives Chemical class 0.000 claims abstract description 15
- 238000001914 filtration Methods 0.000 claims abstract description 5
- 239000000706 filtrate Substances 0.000 claims abstract description 4
- ZQSIJRDFPHDXIC-UHFFFAOYSA-N daidzein Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(O)=CC=C2C1=O ZQSIJRDFPHDXIC-UHFFFAOYSA-N 0.000 claims description 42
- 241000219780 Pueraria Species 0.000 claims description 29
- 235000007240 daidzein Nutrition 0.000 claims description 21
- 238000000926 separation method Methods 0.000 claims description 14
- 238000010828 elution Methods 0.000 claims description 12
- 239000004952 Polyamide Substances 0.000 claims description 10
- 229920002647 polyamide Polymers 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- 239000000843 powder Substances 0.000 claims description 8
- 239000012141 concentrate Substances 0.000 claims description 7
- 238000001953 recrystallisation Methods 0.000 claims description 5
- 238000000227 grinding Methods 0.000 claims description 3
- 230000006837 decompression Effects 0.000 claims 1
- 230000008569 process Effects 0.000 abstract description 3
- 244000046146 Pueraria lobata Species 0.000 abstract 2
- TWCMVXMQHSVIOJ-UHFFFAOYSA-N Aglycone of yadanzioside D Natural products COC(=O)C12OCC34C(CC5C(=CC(O)C(O)C5(C)C3C(O)C1O)C)OC(=O)C(OC(=O)C)C24 TWCMVXMQHSVIOJ-UHFFFAOYSA-N 0.000 abstract 1
- PLMKQQMDOMTZGG-UHFFFAOYSA-N Astrantiagenin E-methylester Natural products CC12CCC(O)C(C)(CO)C1CCC1(C)C2CC=C2C3CC(C)(C)CCC3(C(=O)OC)CCC21C PLMKQQMDOMTZGG-UHFFFAOYSA-N 0.000 abstract 1
- 235000010469 Glycine max Nutrition 0.000 abstract 1
- 244000068988 Glycine max Species 0.000 abstract 1
- PFOARMALXZGCHY-UHFFFAOYSA-N homoegonol Natural products C1=C(OC)C(OC)=CC=C1C1=CC2=CC(CCCO)=CC(OC)=C2O1 PFOARMALXZGCHY-UHFFFAOYSA-N 0.000 abstract 1
- 238000011144 upstream manufacturing Methods 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 239000000470 constituent Substances 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 229920002472 Starch Polymers 0.000 description 3
- 235000019698 starch Nutrition 0.000 description 3
- 239000008107 starch Substances 0.000 description 3
- 230000008901 benefit Effects 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 238000013375 chromatographic separation Methods 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 238000010298 pulverizing process Methods 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- 206010002383 Angina Pectoris Diseases 0.000 description 1
- 208000020446 Cardiac disease Diseases 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- GAMYVSCDDLXAQW-AOIWZFSPSA-N Thermopsosid Natural products O(C)c1c(O)ccc(C=2Oc3c(c(O)cc(O[C@H]4[C@H](O)[C@@H](O)[C@H](O)[C@H](CO)O4)c3)C(=O)C=2)c1 GAMYVSCDDLXAQW-AOIWZFSPSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000003712 anti-aging effect Effects 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 210000001367 artery Anatomy 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 210000001627 cerebral artery Anatomy 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000000916 dilatatory effect Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 229930003944 flavone Natural products 0.000 description 1
- 150000002212 flavone derivatives Chemical class 0.000 description 1
- 235000011949 flavones Nutrition 0.000 description 1
- 229930003935 flavonoid Natural products 0.000 description 1
- -1 flavonoid compound Chemical class 0.000 description 1
- 235000017173 flavonoids Nutrition 0.000 description 1
- 208000019622 heart disease Diseases 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 208000010125 myocardial infarction Diseases 0.000 description 1
- 239000002547 new drug Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- VHBFFQKBGNRLFZ-UHFFFAOYSA-N vitamin p Natural products O1C2=CC=CC=C2C(=O)C=C1C1=CC=CC=C1 VHBFFQKBGNRLFZ-UHFFFAOYSA-N 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
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- Medicines Containing Plant Substances (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention discloses a process for extracting and separating isoflavones from kudzu slag, which comprises the steps of disintegrating kudzu slag to 60-150 meshes, loading into a liquid dynamic continuous flow upstream extraction device for alcohol extraction, combining the extract liquid and filtering, concentrating the filtrate to obtain total isoflavones extract, and separating the total isoflavones extract to obtain puerarin and soybean aglycone.
Description
(1) technical field
The present invention relates to a kind of from the Pueraria lobota slag method of extraction separation isoflavones
(2) background technology
Then do not consider the extraction of flavonoid compound when from the bright root of kudzu vine, extracting starch, residue all abandon need not, and in the root of kudzu vine greatly effective constituent still be retained in the residue.Main effective constituent is puerarin and daidzein.In recent years, the pharmacological action of its effective constituent that a large amount of bibliographical informations arranged both at home and abroad.Puerarin is made medicine as raw material, is used widely clinically, and puerarin is used for the treatment of the disease of stenocardia, hypertension, myocardial infarction, heart disorder, high blood viscosity; Daidzein has dilating effect to official's shape artery and cerebral arteries, to anticancer, anti-ageing important curative effect arranged also.Especially, at present puerarin has become one of choice drug of hospitals at different levels cardiovascular and cerebrovascular medicine for treatment; Radix Puerariae isoflavone is mainly the bulk drug of two, three, four class cardio-cerebrovascular new drugs at home; Picture South East Asia, Japan, area such as North America and country are in great demand to high-load puerarin.
At present, China often rests in the extraction to root of kudzu vine piece root the extraction of Radix Puerariae isoflavone, and the waste residue that kudzuvine root starch manufacturer has then been ignored after kudzuvine root starch extracted extracts, and has caused ecological environment problem.The extraction Radix Puerariae flavone mainly contains water and carries and two kinds of methods of alcohol extracting.The piece root that alcohol extracting method is primarily aimed at the root of kudzu vine extracts, and is divided into methods such as heating and refluxing extraction, cold soaking extraction and diacolation extraction, and the root of kudzu vine total isoflavone that obtains obtains products such as puerarin by chromatographic separation.The problem that these technologies mainly exist is that the operational cycle is long, and extraction efficiency is not high, and the puerarin product content that obtains is generally on the low side, and uses organic solvents such as propyl carbinol, ethyl acetate in the leaching process, causes the difficult solution of dissolvent residual problem.
(3) summary of the invention
To the irrational present situation of the Pueraria lobota utilization of resources, the invention provides the novel method of effective constituent in a kind of high efficiency extraction Pueraria lobota slag at domestic.The technical scheme that the present invention takes for the technical solution problem is:
A kind of from the Pueraria lobota slag method of extraction separation isoflavones, may further comprise the steps: the Pueraria lobota slag is crushed to 60～150 orders, places the dynamic continuous counter-flow extraction equipment alcohol extracting of liquid, united extraction liquid; With extracting liquid filtering, filtrate concentrating obtains the total isoflavone extract; Separate the total isoflavone extract and obtain puerarin and daidzein.
Above-mentioned separation total isoflavone extract preferably carries out as follows: 30～60 purpose polyamide columns on the total isoflavone extract, with the ethanol elution of water and 25～95%, collect the elutriant that contains puerarin and daidzein respectively; Each elutriant that obtains is concentrated the back recrystallization, obtain puerarin and daidzein.
Described from the Pueraria lobota slag method of extraction separation isoflavones, preferably carry out according to the following steps:
(1) the Pueraria lobota slag is carried out superfine grinding, obtain 60～150 purpose powder;
(2) Pueraria lobota slag fine powder is inserted in the dynamic continuous counter-flow extraction equipment of liquid, and the ethanol with 60～95%, extracts 2～4 times under 30～75 ℃ extraction temperature as extracting solvent, and each solid-to-liquid ratio of extracting is 1: 1～3, and total extraction time is 0.5～4 hour;
(3) with extracting liquid filtering, concentrating under reduced pressure obtains total isoflavone;
(4) 30～60 purpose polyamide columns on the total isoflavone with the ethanol elution of water and 25～95%, are collected the elutriant that is rich in puerarin and daidzein;
Each elutriant that (5) will obtain concentrates the back recrystallization, obtains puerarin and daidzein.
In the described step (1), the Pueraria lobota slag can carry out coarse reduction earlier, carries out superfine grinding again.
As a kind of method of the purity that improves Pueraria lobota slag extract of the present invention, the present invention is also preferably with step
(4) elutriant that obtains carries out the secondary chromatography, goes up 60～200 purpose polyamide columns after concentrating as each elutriant that step (4) is obtained again respectively with 25～95% ethanol gradient elution, and the eluting fraction that obtains is used for step (5).
The dynamic continuous counter-flow extraction equipment of described liquid is preferably a plurality of extraction element serial or parallel connections or series-parallel connection is share.Utilize the dynamic Continuous Countercurrent Extraction technology of liquid, Pueraria lobota slag powder is placed in the extraction element, constantly extracts active ingredients is come out, shortened the consumption of extracting cycle and solvent greatly by the round-robin extracting solution.
As to of the present invention preferred, the extracting solution of described step (2) can also repeat to extract to apply mechanically, and as extract new Pueraria lobota slag powder with secondary raffinate, No. three times extracting solution extracts the Pueraria lobota slag that once extracted, and the like.
Excellent the getting by following processing condition of the dynamic Continuous Countercurrent Extraction of described liquid undertaken:
Under 60 ℃ extraction temperature, the ethanol with 95% is as extracting solvent, and each solid-to-liquid ratio of extracting is 1: 3, extracts 3 times, and total extraction time is 4 hours.
Perhaps: under 45 ℃ extraction temperature, the ethanol with 70% is as extracting solvent, and each solid-to-liquid ratio of extracting is 1: 3, extracts 3 times, and total extraction time is 3 hours.
The extraction yield that obtains Radix Puerariae isoflavone by superfine technique and the dynamic Continuous Countercurrent Extraction technology of liquid is 85～95%, the puerarin that chromatographic separation obtains and the content of daidzein reach more than 90%, and the product content that obtains through recrystallization reaches more than 98%.
Of the present invention from the Pueraria lobota slag method of extraction separation isoflavones made full use of Ge Ziyuan, its economic benefit, obvious social benefit, the ecotope effect is huge.This technical process is simple, reasonable design method, and the extraction efficiency height, extracting cycle is short, and total solvent consumption is few, and the product purity height that obtains very is beneficial to suitability for industrialized production.
(4) embodiment
The invention will be further described below in conjunction with specific embodiment, but protection scope of the present invention is not limited to this.
Embodiment 1
Take by weighing dried Pueraria lobota slag 2kg, the Pueraria lobota slag is carried out thick, thin twice pulverizing, obtain 60～100 purpose powder, under 60 ℃ extraction temperature, ethanol with 95% is as extracting solvent, and each solid-to-liquid ratio of extracting is 1: 2, extracts 3 times, extraction time is 3 hours, extracts 3 times, and each extraction time is 1 hour.United extraction liquid filters and concentrating under reduced pressure obtains total isoflavone, and extraction yield is 86%.
30～60 purpose polyamide columns on the total isoflavone are with the ethanol gradient elution of water and 25～95%.At first, with water elution, and TLC follows the tracks of.By the time after having cut just to come out, change ethanol (V/V) eluant solution with 25%.The concentration of elutriant is improved gradually, increase the concentration to 60% of elutriant again up to bringing up to 95% after waiting the puerarin wash-out to finish.Collect the elutriant that is rich in puerarin and daidzein, concentrate eluant respectively; Each elutriant is gone up 100～200 purpose polyamide columns respectively carry out the secondary gradient elution with 25～95% ethanol gradient, the secondary elutriant that obtains concentrates and to obtain content and be: puerarin 90% and daidzein 91% (HPLC mensuration).With 1: 1 acetic acid and recrystallizing methanol puerarin concentrated solution, obtain puerarin 98%, with recrystallizing methanol daidzein concentrated solution, obtain daidzein 98%.
Embodiment 2
Take by weighing dried Pueraria lobota slag 2kg, the Pueraria lobota slag is carried out thick, thin twice pulverizing, obtain 100～150 purpose powder, under 45 ℃ extraction temperature, the ethanol with 70% is as extracting solvent, and each solid-to-liquid ratio of extracting is 1: 3, extract 3 times, extraction time is 4 hours, was respectively 2 hours for the first time, and respectively be 1 hour for the second time, for the third time.United extraction liquid filters and concentrating under reduced pressure obtains total isoflavone, and extraction yield is 89%.
30～60 purpose polyamide columns on the total isoflavone are with the ethanol gradient elution of water and 25～95%.At first, with water elution, TLC follows the tracks of.By the time after having cut just to come out, change ethanol (V/V) eluant solution with 25%.The concentration of elutriant is improved gradually, increase the concentration to 50% of elutriant again up to bringing up to 95% after waiting the basic wash-out of puerarin to finish.Collect the elutriant that is rich in puerarin and daidzein, concentrate eluant respectively; Each elutriant is gone up 60～100 purpose polyamide columns respectively carry out the secondary gradient elution with 25～95% ethanol gradient, the elutriant that obtains concentrates and to obtain content and be: puerarin 91% and daidzein 93% (HPLC mensuration).With 1: 1 acetic acid and recrystallizing methanol puerarin concentrated solution, obtain puerarin 99%, with recrystallizing methanol daidzein concentrated solution, obtain daidzein 98%.
Claims (7)
1, a kind of from the Pueraria lobota slag method of extraction separation isoflavones, it is characterized in that may further comprise the steps: the Pueraria lobota slag is crushed to 60～150 orders, places the dynamic continuous counter-flow extraction equipment alcohol extracting of liquid, united extraction liquid; With extracting liquid filtering, filtrate concentrating obtains the total isoflavone extract; Separate the total isoflavone extract and obtain puerarin and daidzein.
2, according to claim 1 from the Pueraria lobota slag method of extraction separation isoflavones, it is characterized in that described separation total isoflavone extract carries out as follows: 30～60 purpose polyamide columns on the total isoflavone extract, with the ethanol elution of water and 25～95%, collect the elutriant that contains puerarin and daidzein respectively; Each elutriant that obtains is concentrated the back recrystallization, obtain puerarin and daidzein.
3, according to claim 2 from the Pueraria lobota slag method of extraction separation isoflavones, it is characterized in that may further comprise the steps:
(1) the Pueraria lobota slag is carried out superfine grinding, obtain 60～150 purpose powder;
(2) Pueraria lobota slag fine powder is inserted in the dynamic continuous counter-flow extraction equipment of liquid, and the ethanol with 60～95% is as extracting solvent, under 30～75 ℃ extraction temperature, extract 2～4 times, each solid-to-liquid ratio of extracting is 1: 1～3, and total extraction time is 0.5～4 hour, united extraction liquid;
(3) with extracting liquid filtering, filtrate decompression reclaims and obtains the total isoflavone extract;
(4) 30～60 purpose polyamide columns on the total isoflavone extract with the ethanol gradient elution of water and 25～95%, are collected the elutriant that contains puerarin and daidzein respectively;
Each elutriant that (5) will obtain concentrates the back recrystallization, obtains puerarin and daidzein.
4, according to claim 3 from the Pueraria lobota slag method of extraction separation isoflavones, it is characterized in that: go up 80～150 purpose polyamide columns after each elutriant that described step (4) obtains concentrates respectively with 25～95% ethanol gradient elution, the elutriant that obtains is used for step (5).
5, according to claim 3 from the Pueraria lobota slag method of extraction separation isoflavones, it is characterized in that the dynamic continuous counter-flow extraction equipment of described liquid is that a plurality of extraction element serial or parallel connections or series-parallel connection are share.
6, according to claim 3 from the Pueraria lobota slag method of extraction separation isoflavones, it is characterized in that in the described step (2): under 60 ℃ extraction temperature, the ethanol with 95% is as extracting solvent, and each solid-to-liquid ratio of extracting is 1: 3, extract 3 times, total extraction time is 4 hours.
7, according to claim 3 from the Pueraria lobota slag method of extraction separation isoflavones, it is characterized in that in the described step (2): under 45 ℃ extraction temperature, the ethanol with 70% is as extracting solvent, and each solid-to-liquid ratio of extracting is 1: 3, extract 3 times, total extraction time is 3 hours.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2004100677282A CN1321993C (en) | 2004-10-28 | 2004-10-28 | Method for extracting and separating isoflavone from kudzu slag |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2004100677282A CN1321993C (en) | 2004-10-28 | 2004-10-28 | Method for extracting and separating isoflavone from kudzu slag |
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| Publication Number | Publication Date |
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| CN1769279A true CN1769279A (en) | 2006-05-10 |
| CN1321993C CN1321993C (en) | 2007-06-20 |
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| CNB2004100677282A Expired - Fee Related CN1321993C (en) | 2004-10-28 | 2004-10-28 | Method for extracting and separating isoflavone from kudzu slag |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101138389B (en) * | 2006-09-08 | 2010-11-10 | 安康市志朗生物资源应用研究所 | Method of comprehensive utilization of waste liquor produced in the refining process of puerarin |
| CN102389091A (en) * | 2011-11-10 | 2012-03-28 | 淮阴师范学院 | Processing method of instant kudzuvine root starch |
| CN105477029A (en) * | 2015-12-17 | 2016-04-13 | 江南大学 | Preparation method of evening primrose seed flavone |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1493695A (en) * | 2003-08-22 | 2004-05-05 | 李全宏 | Prcess of extracting kudzu vine root starch, kudiu vine root polysaccharide and kudzu vine root isoflavone from kudzu vine root synchronously |
-
2004
- 2004-10-28 CN CNB2004100677282A patent/CN1321993C/en not_active Expired - Fee Related
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101138389B (en) * | 2006-09-08 | 2010-11-10 | 安康市志朗生物资源应用研究所 | Method of comprehensive utilization of waste liquor produced in the refining process of puerarin |
| CN102389091A (en) * | 2011-11-10 | 2012-03-28 | 淮阴师范学院 | Processing method of instant kudzuvine root starch |
| CN105477029A (en) * | 2015-12-17 | 2016-04-13 | 江南大学 | Preparation method of evening primrose seed flavone |
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| Publication number | Publication date |
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| CN1321993C (en) | 2007-06-20 |
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