CN1594344A - Process for separating high pure neohesperidin from fruit of citron or trifoliate orange - Google Patents
Process for separating high pure neohesperidin from fruit of citron or trifoliate orange Download PDFInfo
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- CN1594344A CN1594344A CN 200410025729 CN200410025729A CN1594344A CN 1594344 A CN1594344 A CN 1594344A CN 200410025729 CN200410025729 CN 200410025729 CN 200410025729 A CN200410025729 A CN 200410025729A CN 1594344 A CN1594344 A CN 1594344A
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- fructus aurantii
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Abstract
The invention provides a process for separating high pure neohesperidin from fruit of citron or trifoliate orange, which mainly comprises, extracting trifoliate orange extractive from trifoliate orange by means of water and ethanol, obtaining the crude extract of trifoliate orange flavones through macroporous absorption resin chromatography, and purifying through n-butyl alcohol extraction and solvent recrystallization method.
Description
Technical field
The invention belongs to the Chinese medicine extraction process of effective component, relate generally to from Chinese medicine extract, the method for separating monomer compound, particularly relate to a kind of from the Fructus Aurantii flavone gruff bring up substance method of separating high-purity neohesperidin.
Background technology
Neohesperidin belongs to the flavanone in the flavonoid compound, and more content is arranged in bitter orange, the dried immature fruit of citron orange, Fructus Aurantii, dried orange peel usually.Pharmacological research shows: the flavonoid in the dried immature fruit of citron orange, the Fructus Aurantii shrinks the non-physiologic of rat unstriated muscle and is restraining effect, and can resist the spastic contraction that bariumchloride, vagusstoff cause, also has anti-inflammatory action in addition.Clinical gasteremphraxis pain, the gastric and duodenal ulcer of being used for the treatment of.Neohesperidin forms neohesperidin dihydrochalcone after hydrogen treatment, be a kind of special sweeting agent, and its sugariness is 1000 times of sucrose.Neohesperidin has better heat-resisting, acid resistance, can be used as the additive of beverage, food.At present, begun to use in more American-European countries, but because production cost is higher, usage quantity is restricted.
Neohesperidin is many to be extracted from citrus, but in the citrus except neohesperidin, contain the very approaching flavonoid glycosides of physico-chemical property such as naringin, Hesperidin toward contact, this makes and separate very difficulty of neohesperidin from the citrus extract.J.A.Del Rio etc. has studied neohesperidin, naringin and the Determination of Hesperidin Content in the different varieties Various Seasonal oranges and tangerines in period that Spain produces, selected a neohesperidin content very high, and naringin and content of hesperidin oranges and tangerines kind is seldom extracted neohesperidin, does not then still have relevant research at home.
Summary of the invention
The purpose of this invention is to provide a kind of from Fructus Aurantii the method for separating high-purity neohesperidin, method of the present invention is achieved through the following technical solutions:
1. extract Fructus Aurantii crude flavonoid powder extract: get the Fructus Aurantii pharmaceutical decocting piece, extract with solvent refluxing, concentrating under reduced pressure removes and desolvates, and obtains Fructus Aurantii crude flavonoid powder extract, wherein (1) is with 60% alcohol reflux, the extracting solution concentrating under reduced pressure removes and desolvates, and crosses the D101 macroporous resin column, respectively water and 30% ethanol elution, discard elutriant, collect 60% ethanol eluate, concentrating under reduced pressure removes and desolvates, and gets the crude flavonoid powder extract; (2) use 95% alcohol reflux again after the water refluxing extraction, with the aqueous extract concentrating under reduced pressure, concentrated solution is crossed the D101 macroporous resin, use 30% ethanol elution, discard elutriant, the ethanol extract of collecting 60% ethanol eluate and 95% merges, concentrating under reduced pressure removes and desolvates, and gets the crude flavonoid powder extract; (3) with 95% alcohol reflux, concentrating under reduced pressure removes and desolvates, the crude flavonoid powder extract.
2. obtain high purity novel aurantiamarin: with n-butanol extraction for several times with Fructus Aurantii crude flavonoid powder solution of extract, to the butanol extraction liquid concentrating under reduced pressure, concentrated solution is left standstill a few hours make and separate out precipitation, the collecting precipitation thing, throw out obtains high purity novel aurantiamarin with methyl alcohol or ethyl alcohol recrystallization several.
The present invention utilizes the difference of other flavonoid compound solubleness in propyl carbinol such as neohesperidin and naringin to carry out separation and purification, enlarged the raw material scope of selecting material that extracts neohesperidin greatly, made all higher flavone gruff bring up substance (as Fructus Aurantii) of some naringins and neohesperidin content also can be used for preparing the neohesperidin monomer.Outstanding progress of the present invention and unusual effect are that Fructus Aurantii is a kind of dry immature fruit of the common bitter orange that is easy to get, and draw materials conveniently, and purifying process of the present invention is simple, with low cost, are suitable for producing in enormous quantities.
Embodiment
The present invention is described further in conjunction with specific embodiments.
Embodiment 1:
Get the Fructus Aurantii pharmaceutical decocting piece, add 8 times of water gaging refluxing extraction 2 hours; Use 8 times 95% alcohol reflux 2 times again, each 2 hours, the water extract is evaporated to concentrated solution: medicinal material is 2: 1, filters, filtrate is splined in the D101 type macroporous resin column, with 3.2 times of amount 30% ethanol elutions, discard elutriant, again with 4 times of amount 60% ethanol elutions, the ethanol extract of collecting elutriant and 95% merges, concentrating under reduced pressure removes and desolvates, and adds an amount of water, and make concentrated solution: medicinal material is 1: 1.
Get concentrated solution and divide 4 extractions with 6 times of amount propyl carbinols, merge butanol extraction liquid, be evaporated to the propyl carbinol concentrated solution: medicinal material is 1: 1, cooling, placement is spent the night and is made precipitation, and precipitation is with 50% recrystallizing methanol 3 times, must white needle-like crystals, this crystallization is a neohesperidin by analysis, and purity is 97.7%.
Embodiment 2:
Get the Fructus Aurantii pharmaceutical decocting piece, with 8 times of amount alcohol reflux of 60% 3 times, each 1.5 hours.The extracting solution concentrating under reduced pressure is become medicinal extract, and thin up becomes every ml to contain the concentration of 1g medicinal material.Filter, filtrate is splined in the D101 type macroporous resin column, and water, 30% ethanol elution discard elutriant respectively, use 60% ethanol elution again, collects 8 times of amount elutriants, and concentrating under reduced pressure removes and desolvates, and adds an amount of water, and make medicinal material: concentrated solution is 1: 1.2.
Get concentrated solution and divide 5 extractions with 7 times of amount propyl carbinols, merge butanol extraction liquid, be evaporated to medicinal material: the propyl carbinol concentrated solution is 1: 1.6, cooling, placing spends the night makes precipitation, and throw out is with 50% recrystallizing methanol 3 times, get white needle-like crystals, purity is 98.3%.
Embodiment 3:
Obtain Fructus Aurantii crude flavonoid powder concentrated solution by embodiment 2, divide 5 extractions, merge butanol extraction liquid with 7 times of amount propyl carbinols, be evaporated to medicinal material: the propyl carbinol concentrated solution is 1: 3, cooling, and placing spends the night makes precipitation, throw out is with 50% recrystallizing methanol 3 times, white needle-like crystals.Purity is 98.7%.
Embodiment 4:
Get the Fructus Aurantii medicinal material, with 8 times of amount alcohol reflux of 95% 4 times, each 1.5 hours, the extract concentrating under reduced pressure is become medicinal extract, thin up is to extracting solution: medicinal material is 1: 1 a concentration.
Get concentrated solution and divide 5 extractions with 6 times of amount propyl carbinols, merge butanol extraction liquid, be evaporated to the propyl carbinol concentrated solution: medicinal material is 1: 1, and cooling is placed and made precipitation in 4 hours, precipitates with 50% recrystallizing methanol 3 times, gets white needle-like crystals, and purity is 98.1%.
Need not further to elaborate, believe and adopt the disclosed content in front, those skilled in the art can use the present invention to greatest extent.Therefore, the specific embodiment of front is interpreted as only illustrating, but not limits the scope of the invention by any way.
Claims (4)
1. the method for a separating high-purity neohesperidin from Fructus Aurantii is a raw material with the Fructus Aurantii pharmaceutical decocting piece, extracts with solvent refluxing, and concentrating under reduced pressure removes and desolvates, and obtains the Fructus Aurantii crude extract, it is characterized in that:
(a) Fructus Aurantii crude flavonoid powder extract is extracted with propyl carbinol;
(b) butanol extraction liquid is carried out concentrating under reduced pressure, concentrated solution is placed to make and is separated out precipitation, the collecting precipitation thing;
(c) throw out obtains high purity novel aurantiamarin with methyl alcohol or ethyl alcohol recrystallization.
2. according to claim 1 a kind of from Fructus Aurantii the method for separating high-purity neohesperidin, it is characterized in that: butanol extraction liquid is evaporated to the propyl carbinol concentrated solution: medicinal material is 1～3: 1.
According to claim 1 and 2 described a kind of from Fructus Aurantii the method for separating high-purity neohesperidin, it is characterized in that: with water, 5～95% ethanol is that the Fructus Aurantii pharmaceutical decocting piece extracts solvent, refluxing extraction.
According to claim 1～3 described a kind of from Fructus Aurantii the method for separating high-purity neohesperidin, it is characterized in that: available macroporous resin enrichment mode is obtained Fructus Aurantii crude flavonoid powder extract in the Fructus Aurantii pharmaceutical decocting piece.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 200410025729 CN1272339C (en) | 2004-06-28 | 2004-06-28 | Process for separating high pure neohesperidin from fruit of citron or trifoliate orange |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 200410025729 CN1272339C (en) | 2004-06-28 | 2004-06-28 | Process for separating high pure neohesperidin from fruit of citron or trifoliate orange |
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| CN1594344A true CN1594344A (en) | 2005-03-16 |
| CN1272339C CN1272339C (en) | 2006-08-30 |
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| CN 200410025729 Expired - Fee Related CN1272339C (en) | 2004-06-28 | 2004-06-28 | Process for separating high pure neohesperidin from fruit of citron or trifoliate orange |
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Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1836665B (en) * | 2005-03-21 | 2010-12-08 | 江西天科医药开发有限公司 | Pharmaceutical uses of hesperidin or its composition |
| CN102068535A (en) * | 2010-12-28 | 2011-05-25 | 江西青峰药业有限公司 | Immature bitter orange or bitter orange total flavonoids extract prepared by ethanol reflux and extraction and application thereof |
| CN101704867B (en) * | 2009-11-03 | 2012-02-01 | 国家海洋局第三海洋研究所 | Method for preparing naringin or hesperidin |
| CN1903279B (en) * | 2005-07-29 | 2012-02-22 | 天津天士力制药股份有限公司 | Method for extraction and separation of Immature Bitter orange |
| CN102464686A (en) * | 2010-11-19 | 2012-05-23 | 苏州宝泽堂医药科技有限公司 | Preparation method of avicularin |
| CN102617673A (en) * | 2012-02-25 | 2012-08-01 | 浙江大学 | Method for separating and purifying naringin and neohesperidin from white skin layer of citrus grandis |
| CN103191239A (en) * | 2010-12-28 | 2013-07-10 | 江西青峰药业有限公司 | Fructus aurantii immaturus or fructus aurantii total-flavonoid extract obtained through ethanol reflux extraction and application thereof |
| CN103191238A (en) * | 2010-12-28 | 2013-07-10 | 江西青峰药业有限公司 | Fructus aurantii immaturus or fructus aurantii total-flavonoid extract obtained through ethanol reflux extraction and application thereof |
| CN103191236A (en) * | 2010-12-28 | 2013-07-10 | 江西青峰药业有限公司 | Fructus aurantii immaturus or fructus aurantii total-flavonoid extract obtained through ethanol reflux extraction and application thereof |
| CN103191237A (en) * | 2010-12-28 | 2013-07-10 | 江西青峰药业有限公司 | Fructus aurantii immaturus or fructus aurantii total-flavonoid extract obtained through ethanol reflux extraction and application thereof |
| CN109912666A (en) * | 2019-03-14 | 2019-06-21 | 重庆市铜梁区子奇药材有限公司 | A method of extracting high-purity aurantiin and neohesperidin simultaneously from Fructus Aurantii |
| CN113121623A (en) * | 2019-12-31 | 2021-07-16 | 江西青峰药业有限公司 | Method for simultaneously preparing two flavanone glycoside monomeric compounds by utilizing industrial chromatographic technology |
-
2004
- 2004-06-28 CN CN 200410025729 patent/CN1272339C/en not_active Expired - Fee Related
Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1836665B (en) * | 2005-03-21 | 2010-12-08 | 江西天科医药开发有限公司 | Pharmaceutical uses of hesperidin or its composition |
| CN1903279B (en) * | 2005-07-29 | 2012-02-22 | 天津天士力制药股份有限公司 | Method for extraction and separation of Immature Bitter orange |
| CN101704867B (en) * | 2009-11-03 | 2012-02-01 | 国家海洋局第三海洋研究所 | Method for preparing naringin or hesperidin |
| CN102464686A (en) * | 2010-11-19 | 2012-05-23 | 苏州宝泽堂医药科技有限公司 | Preparation method of avicularin |
| CN102068535B (en) * | 2010-12-28 | 2013-05-08 | 江西青峰药业有限公司 | Immature bitter orange or bitter orange total flavonoids extract prepared by ethanol reflux and extraction and application thereof |
| CN102068535A (en) * | 2010-12-28 | 2011-05-25 | 江西青峰药业有限公司 | Immature bitter orange or bitter orange total flavonoids extract prepared by ethanol reflux and extraction and application thereof |
| CN103191239A (en) * | 2010-12-28 | 2013-07-10 | 江西青峰药业有限公司 | Fructus aurantii immaturus or fructus aurantii total-flavonoid extract obtained through ethanol reflux extraction and application thereof |
| CN103191238A (en) * | 2010-12-28 | 2013-07-10 | 江西青峰药业有限公司 | Fructus aurantii immaturus or fructus aurantii total-flavonoid extract obtained through ethanol reflux extraction and application thereof |
| CN103191236A (en) * | 2010-12-28 | 2013-07-10 | 江西青峰药业有限公司 | Fructus aurantii immaturus or fructus aurantii total-flavonoid extract obtained through ethanol reflux extraction and application thereof |
| CN103191237A (en) * | 2010-12-28 | 2013-07-10 | 江西青峰药业有限公司 | Fructus aurantii immaturus or fructus aurantii total-flavonoid extract obtained through ethanol reflux extraction and application thereof |
| CN102617673A (en) * | 2012-02-25 | 2012-08-01 | 浙江大学 | Method for separating and purifying naringin and neohesperidin from white skin layer of citrus grandis |
| CN109912666A (en) * | 2019-03-14 | 2019-06-21 | 重庆市铜梁区子奇药材有限公司 | A method of extracting high-purity aurantiin and neohesperidin simultaneously from Fructus Aurantii |
| CN109912666B (en) * | 2019-03-14 | 2023-04-11 | 重庆市铜梁区子奇药材有限公司 | Method for simultaneously extracting high-purity naringin and neohesperidin from fructus aurantii |
| CN113121623A (en) * | 2019-12-31 | 2021-07-16 | 江西青峰药业有限公司 | Method for simultaneously preparing two flavanone glycoside monomeric compounds by utilizing industrial chromatographic technology |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1272339C (en) | 2006-08-30 |
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| C06 | Publication | ||
| PB01 | Publication | ||
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| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| EE01 | Entry into force of recordation of patent licensing contract |
Assignee: Changshu Leiyunshang Pharmaceutical Co., Ltd. Assignor: Zhejiang University Contract fulfillment period: 2007.11.15 to 2013.11.15 contract change Contract record no.: 2008320000008 Denomination of invention: Process for separating high pure neohesperidin from fruit of citron or trifoliate orange Granted publication date: 20060830 License type: Exclusive license Record date: 2008.4.8 |
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| LIC | Patent licence contract for exploitation submitted for record |
Free format text: EXCLUSIVE LICENCE; TIME LIMIT OF IMPLEMENTING CONTACT: 2007.11.15 TO 2013.11.15 Name of requester: CHANGSHU LEIYUNSHANG PHARMACEUTICAL CO., LTD. Effective date: 20080408 |
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| C17 | Cessation of patent right | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20060830 Termination date: 20100628 |