CN1321992C - Method for extracting and separating isoflavone from kudzu - Google Patents
Method for extracting and separating isoflavone from kudzu Download PDFInfo
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- CN1321992C CN1321992C CNB2004100677263A CN200410067726A CN1321992C CN 1321992 C CN1321992 C CN 1321992C CN B2004100677263 A CNB2004100677263 A CN B2004100677263A CN 200410067726 A CN200410067726 A CN 200410067726A CN 1321992 C CN1321992 C CN 1321992C
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- 235000010575 Pueraria lobata Nutrition 0.000 title claims abstract description 39
- 241000219781 Pueraria montana var. lobata Species 0.000 title claims abstract description 38
- 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 38
- 235000008696 isoflavones Nutrition 0.000 title claims abstract description 38
- GOMNOOKGLZYEJT-UHFFFAOYSA-N isoflavone Chemical compound C=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC=C1 GOMNOOKGLZYEJT-UHFFFAOYSA-N 0.000 title claims abstract description 25
- 238000000034 method Methods 0.000 title abstract description 18
- 238000000605 extraction Methods 0.000 claims abstract description 60
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 45
- 239000007788 liquid Substances 0.000 claims abstract description 28
- 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 27
- 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 27
- 239000000284 extract Substances 0.000 claims abstract description 24
- 239000002904 solvent Substances 0.000 claims abstract description 13
- 239000000843 powder Substances 0.000 claims abstract description 10
- ZQSIJRDFPHDXIC-UHFFFAOYSA-N daidzein Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(O)=CC=C2C1=O ZQSIJRDFPHDXIC-UHFFFAOYSA-N 0.000 claims description 40
- 235000007240 daidzein Nutrition 0.000 claims description 19
- 238000000926 separation method Methods 0.000 claims description 14
- 150000002515 isoflavone derivatives Chemical class 0.000 claims description 13
- 238000010828 elution Methods 0.000 claims description 12
- 239000004952 Polyamide Substances 0.000 claims description 10
- 229920002647 polyamide Polymers 0.000 claims description 10
- 238000001953 recrystallisation Methods 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- 239000012141 concentrate Substances 0.000 claims description 8
- 238000001914 filtration Methods 0.000 claims description 4
- 239000000706 filtrate Substances 0.000 claims description 3
- 238000000227 grinding Methods 0.000 claims description 3
- 230000006837 decompression Effects 0.000 claims 1
- 230000008901 benefit Effects 0.000 abstract description 5
- 230000000694 effects Effects 0.000 abstract description 3
- 230000008569 process Effects 0.000 abstract description 3
- 230000002349 favourable effect Effects 0.000 abstract 2
- 244000046146 Pueraria lobata Species 0.000 abstract 1
- 229930182470 glycoside Natural products 0.000 abstract 1
- 150000002338 glycosides Chemical class 0.000 abstract 1
- 238000009776 industrial production Methods 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 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
- 239000000470 constituent Substances 0.000 description 3
- GMTUGPYJRUMVTC-UHFFFAOYSA-N Daidzin Natural products OC(COc1ccc2C(=O)C(=COc2c1)c3ccc(O)cc3)C(O)C(O)C(O)C=O GMTUGPYJRUMVTC-UHFFFAOYSA-N 0.000 description 2
- KYQZWONCHDNPDP-UHFFFAOYSA-N Daidzoside Natural products OC1C(O)C(O)C(CO)OC1OC1=CC=C2C(=O)C(C=3C=CC(O)=CC=3)=COC2=C1 KYQZWONCHDNPDP-UHFFFAOYSA-N 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 238000013375 chromatographic separation Methods 0.000 description 2
- KYQZWONCHDNPDP-QNDFHXLGSA-N daidzein 7-O-beta-D-glucoside Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=CC=C2C(=O)C(C=3C=CC(O)=CC=3)=COC2=C1 KYQZWONCHDNPDP-QNDFHXLGSA-N 0.000 description 2
- 229940079593 drug Drugs 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
- 241000219780 Pueraria Species 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
- 208000019622 heart disease Diseases 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930013032 isoflavonoid Natural products 0.000 description 1
- 150000003817 isoflavonoid derivatives Chemical class 0.000 description 1
- 235000012891 isoflavonoids Nutrition 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
- 238000002791 soaking Methods 0.000 description 1
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- Medicines Containing Plant Substances (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The present invention discloses a method for extracting and separating isoflavone from kudzu, which comprises the following steps: kudzu vine is crushed into powder with 60 to 150 meshes; the powder is placed in a liquid dynamic device for continuous counterflow extraction to be extracted by alcohol, and extracting solutions are combined; the extracting liquids are filtrated, filtered solutions are concentrated, and total isoflavone extracts are obtained; the total isoflavone extracts are separated, and puerarin and soy glycoside are obtained. The method for extracting and separating isoflavone from kudzu of the present invention fully utilizes kudzu resources, so the economic benefits and social benefits are obvious, and the effects on ecological environment are favorable. The method of the present invention has the advantages of simple technical process, reasonable design method, high extraction efficiency, short period of extracting, little consumption of total solvent, and high purity of products obtained by the method; the method is favorable for industrial production.
Description
(1) technical field
The present invention relates to a kind of from kudzu the method for extraction separation isoflavones.
(2) background technology
The kudzu and the root of kudzu vine contain abundant isoflavonoid equally, and main effective constituent is puerarin, daidzin 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 and daidzin are made medicine as raw material, are 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, has ignored in the extraction that contains the kudzu of enriching isoflavones.Mainly carry and two kinds of methods of alcohol extracting and separate kudzu vine root by water.Alcohol extracting method 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 the puerarin product 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 object of the invention is to provide the method for effective constituent in a kind of high efficiency extraction kudzu at domestic.The technical solution adopted in the present invention is:
A kind of from kudzu the method for extraction separation isoflavones, may further comprise the steps: kudzu 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.
The method of above-mentioned separation total isoflavone extract is preferably carried 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.
Further, described from kudzu the method for extraction separation isoflavones, preferably carry out according to the following steps:
(1) kudzu is carried out superfine grinding, obtain 60～150 purpose powder;
(2) the kudzu 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 30～750 ℃ 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 respectively;
Each elutriant that (5) will obtain concentrates the back recrystallization, obtains puerarin and daidzein.
In the described step (1), kudzu can carry out coarse reduction earlier, carries out superfine grinding again.
As a kind of method of the purity that improves kudzu extract of the present invention, the present invention also recommends 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, the kudzu 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 kudzu powder with secondary raffinate, No. three times extracting solution extracts the kudzu of once extracting, 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 kudzu the method for 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 kudzu 2kg, kudzu is carried out thick, thin twice pulverizing, obtain 60～100 purpose powder, under 60 ℃ extraction temperature, the ethanol with 95% is as extracting solvent, and each solid-to-liquid ratio of extracting is 1: 2.5, extract 3 times, total 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 90%.
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 45% 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 respectively, concentrate each elutriant; 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 91% and daidzein 92% (HPLC mensuration).Methyl alcohol=1: 1) and daidzein 99% (methyl alcohol) be respectively puerarin 98% (recrystallization solvent, acetic acid: behind the recrystallization.
Embodiment 2
Take by weighing dried kudzu 2kg, kudzu 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, total extraction time is 3 hours, 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, 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%.Concentration with elutriant improves gradually successively, increases the concentration to 55% 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 35～95% ethanol gradient, the elutriant that obtains secondary concentrates and to obtain content and be: puerarin 92% and daidzein 93% (HPLC mensuration).Methyl alcohol=1: 1) and daidzein 99% be respectively puerarin 99% (recrystallization solvent, acetic acid: behind the recrystallization.
Claims (7)
1, a kind of from kudzu the method for extraction separation isoflavones, it is characterized in that may further comprise the steps: kudzu 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 kudzu the method for 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 kudzu the method for extraction separation isoflavones, it is characterized in that may further comprise the steps:
(1) kudzu is carried out superfine grinding, obtain 60～150 purpose powder;
(2) the kudzu 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 concentrates 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 kudzu the method for extraction separation isoflavones, it is characterized in that: go up 60～200 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 kudzu the method for 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 kudzu the method for 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 kudzu the method for 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.
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| Application Number | Priority Date | Filing Date | Title |
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| CNB2004100677263A CN1321992C (en) | 2004-10-28 | 2004-10-28 | Method for extracting and separating isoflavone from kudzu |
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| CNB2004100677263A CN1321992C (en) | 2004-10-28 | 2004-10-28 | Method for extracting and separating isoflavone from kudzu |
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| CN1769278A CN1769278A (en) | 2006-05-10 |
| CN1321992C true CN1321992C (en) | 2007-06-20 |
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| CN100387590C (en) * | 2006-08-23 | 2008-05-14 | 浙江大学 | Method of extracting, separating soybean aglucone from kudzu |
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| CN103637602A (en) * | 2013-11-21 | 2014-03-19 | 山东中大药业有限公司 | Health-care medical pillow for middle-aged people with cervical spondylosis |
| CN103637603A (en) * | 2013-11-21 | 2014-03-19 | 山东中大药业有限公司 | Cervical spondylosis health care medicine pillow |
| CN103637605A (en) * | 2013-11-22 | 2014-03-19 | 山东中大药业有限公司 | Hypertensive healthcare drug pillow |
| CN103637606A (en) * | 2013-11-22 | 2014-03-19 | 山东中大药业有限公司 | Hypertensive healthcare drug pillow |
| CN103637608B (en) * | 2013-11-22 | 2015-08-26 | 榆林市第一医院 | A kind of hypertensive healthcare drug pillow |
| CN103637607A (en) * | 2013-11-22 | 2014-03-19 | 山东中大药业有限公司 | Hypertensive healthcare drug pillow |
| CN103829682B (en) * | 2013-12-03 | 2016-04-20 | 枣庄汇康医疗用品有限公司 | A kind of senile chronic bronchitis medicine-filled pillow |
| CN108640957B (en) * | 2018-06-28 | 2021-07-06 | 湖南华诚生物资源股份有限公司 | Method for simultaneously extracting various pueraria isoflavone glycosides from pueraria crude extract |
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| CN1365976A (en) * | 2001-01-15 | 2002-08-28 | 张家界科新有限责任公司 | Process for extracting medicinal component from pueraria root |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1365976A (en) * | 2001-01-15 | 2002-08-28 | 张家界科新有限责任公司 | Process for extracting medicinal component from pueraria root |
Non-Patent Citations (3)
| Title |
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| 一种简便方法从野葛根中提取纯化葛根异黄酮 贺云 张尊听 杨红兵，天然产物研究与开发，第1期 2002 * |
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Assignee: Zhejiang Jolly Pharmaceutical Co., Ltd. Assignor: Zhejiang University of Technology Contract fulfillment period: 2007.12.10 to 2013.12.10 contract change Contract record no.: 2008330001118 Denomination of invention: Method for extracting and separating isoflavone from kudzu Granted publication date: 20070620 License type: Exclusive license Record date: 20081016 |
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Free format text: EXCLUSIVE LICENSE; TIME LIMIT OF IMPLEMENTING CONTACT: 2007.12.10 TO 2013.12.10; CHANGE OF CONTRACT Name of requester: ZHEJIANG PROVINCE ZUOLI PHARMACEUTICAL CO., LTD. Effective date: 20081016 |
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Granted publication date: 20070620 Termination date: 20151028 |
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