CN102234299A - Separation method of hyperin - Google Patents
Separation method of hyperin Download PDFInfo
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- CN102234299A CN102234299A CN2010101580449A CN201010158044A CN102234299A CN 102234299 A CN102234299 A CN 102234299A CN 2010101580449 A CN2010101580449 A CN 2010101580449A CN 201010158044 A CN201010158044 A CN 201010158044A CN 102234299 A CN102234299 A CN 102234299A
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- galactoside
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- quercetin
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Abstract
The invention relates to a separation method of hyperin. The separation method is characterized by crushing Crataegus pinnatifida or hawthorn leaf herbs into coarse powder, carrying out reflux extraction with a water-containing alcohol, filtering the extract liquid, mixing filtrates, concentrating while depressurizing until no alcohol odor exists, removing impurities by AB-8 or D101 macroporous adsorption resin, eluting with 30-80% ethanol, concentrating while depressurizing until no alcohol odor exists, drying, separating the dried material by polyamide column chromatography, carrying out gradient elution with water-containing ethanol, concentrating the eluate while depressurizing, carrying out silica gel column chromatography, and then eluting with ethyl acetate-butanone-formic acid-water or ethyl acetate-acetone-formic acid-water to directly obtain hyperin. The hyperin separated by using the separation method has high yield and high purity; and the separation method is simple and practical, low in toxicity, environmentally friendly and suitable for industrial production.
Description
Technical field
The present invention relates to method by common polymeric amide and silica gel column chromatography separation Quercetin 3-galactoside, what The present invention be more particularly directed to is to adopt silica gel column chromatography, with ethyl acetate-butanone (or acetone)-formic acid-water is eluent, from Fruit of Pashi Pear leaf or Folium Crataegi extract, directly separate the method for Quercetin 3-galactoside.
Background technology
Howthorn Leaf is the dry leave of rosaceous plant Fruit of Pashi Pear (Crataegus pinnatifida Bge.var major N.E.Br.), hawthorn (C.pinnatifida Bge.), records in the Pharmacopoeia of the People's Republic of China 2010 editions, 30 pages.Have promoting blood circulation and removing blood stasisly, regulate the flow of vital energy and promote blood circulation, be used for qi depression to blood stasis, chest distress, palpitaition is seen and is forgotten, dizzy tinnitus.Result of study shows that Quercetin 3-galactoside is to be proved the treatment cardiovascular disorder, and spasmolysis and analgesia is arranged, protection gastric mucosa, hepatic tissue and regulating blood fat, and strengthening immunity, antidepressant reaches the provide protection to cardiac-cerebral ischemia.Silica gel chromatography is fit to the separating flavone constituents, so the present invention successfully is used to separate Quercetin 3-galactoside with polyamides silica gel column chromatography technology, can be used as the raw material of treatment relative disease medicine.
The preparation method of Quercetin 3-galactoside mainly adopts alcohol extracting, the solvent extraction method of binding silica gel column chromatography simultaneously at present.The bibliographical information characteristics are cost height, and the cycle is long, yield low (Fruit of Pashi Pear phyllody composition Study Chinese medicinal materials such as Liu Ronghua, 2006,29 (11); Howthorn Leaf The Chemical Constituents CHINA JOURNAL OF CHINESE MATERIA MEDICAs such as fourth apricot bud, 1990; 15 (5); The content of Quercetin 3-galactoside China medicine company in the high effective liquid chromatography for measuring Howthorn Leaf such as Li Biao, 2003,12 (12)).
Summary of the invention
Purpose of the present invention has provided easy, environmental protection, quick, purity height, a kind of method of separating Quercetin 3-galactoside that productive rate is high.
The object of the present invention is achieved like this:
A kind of method of separating Quercetin 3-galactoside, be to get Howthorn Leaf or Fruit of Pashi Pear leaf, doubly measure with 16-24, concentration is aqueous ethanol refluxing extraction 2-3 time of 30-80% with the mass percent, each 1-3 hour, extracting liquid filtering, merging filtrate, being evaporated to does not have the alcohol flavor, again through AB-8 or the removal of impurities of D101 macroporous adsorbent resin, with concentration is that the 30-80% ethanol elution extremely no longer detects till the flavones, and this elutriant concentrating under reduced pressure reclaims ethanol and do not distinguish the flavor of drying to there being alcohol, the dry thing of gained separates through polyamide column chromatography, use the 30-80% ethanol gradient elution, consumption is 3-4 a times of column volume, elutriant is evaporated to dried, the dry thing of gained separates through 200-300 order silica gel column chromatography, with ethyl acetate-butanone (or acetone)-formic acid-water elution, directly obtain the Quercetin 3-galactoside powder at last, purity is 90-99%.
Alcohol extract filters, and being evaporated to does not have the alcohol flavor, and through AB-8 (D101) macroporous adsorbent resin water flushing removal of impurities, with the 30-80% ethanol elution, decompression recycling ethanol extract obtainedly separates through polyamide column chromatography.
Polyamide column is used the aqueous ethanol gradient elution respectively, and 70% all flow points of ethanol position (1-2 column volume) eluate concentrating under reduced pressure, dry thing with ethyl acetate-butanone (or acetone)-formic acid-water elution, get Quercetin 3-galactoside again through silica gel column chromatography.Ketone can be selected butanone or acetone for use, and the ratio that adopts ethyl acetate-butanone (or acetone)-formic acid-water is by (6: 2: 1: 0.2) regulation was adjusted.
The extract yield of the prepared Quercetin 3-galactoside of present method is 0.01-0.05%, and its content is 90-99% (adopt high performance liquid chromatography, normalization method is measured).This extract can separately or be united as bulk drug and is applied in the healing potion of various relative diseases.
What the present invention was different with existing document is: employing polymeric amide and silica gel column chromatography separation are the Quercetin 3-galactoside in separable Fruit of Pashi Pear leaf or the Howthorn Leaf, avoided operational difficulty, have adopted chloroform and the high shortcoming of methanol-eluted fractions cost.Use the isolating Quercetin 3-galactoside yield height of this law, purity height, little, the environmental protection of toxicity.Present method is easy, quick, practical, is fit to suitability for industrialized production.
Embodiment
Embodiment one
The Fruit of Pashi Pear leaf is ground into meal, and with 70% alcohol reflux of 24 times of amounts 3 times, each extraction time was respectively 2 hours, 1 hour, filter, and merging filtrate, being evaporated to does not have the alcohol flavor.Gained medicinal extract is through the AB-8 macroporous adsorbent resin, no longer detect with 50 times of column volume water elutions removal of impurities to sugar, end to no longer detecting flavones with 70% ethanol elution again, alcohol eluen is evaporated to does not have the alcohol flavor, dry, the dry thing of gained is through polyamide column chromatography aqueous ethanol gradient elution, 70% all flow points of ethanol position (1-2 column volume) eluate concentrating under reduced pressure, the dry thing of gained separates through silica gel column chromatography (wherein silica gel is with the 200-300 order), 0.2) with ethyl acetate-butanone (or acetone)-formic acid-water (6: 2: 1: wash-out such as, get the Quercetin 3-galactoside powder, purity is all greater than 90% (through high performance liquid chromatography, normalization method is measured).
Embodiment two
Howthorn Leaf is ground into meal, with 24 times of amount 50% alcohol reflux 2 times, and one time 3 hours, one time 2 hours, filter, merging filtrate, being evaporated to does not have the alcohol flavor.Gained medicinal extract no longer detects through D101 macroporous adsorbent resin removal of impurities to sugar, use 60% ethanol elution again, the alcohol eluen concentrating under reduced pressure, through polyamide column chromatography aqueous ethanol gradient elution, 70% all flow points of ethanol position (1-2 column volume) eluate concentrating under reduced pressure, the dry thing of gained separates through silica gel column chromatography (wherein silica gel is with the 200-300 order), 0.2) with ethyl acetate-butanone (or acetone)-formic acid-water (6: 2: 1: wash-out such as, get the Quercetin 3-galactoside powder, purity is 99% (through high performance liquid chromatography, normalization method is measured).
Embodiment three
The Fruit of Pashi Pear leaf is ground into meal, with 20 times of amount 60% alcohol reflux 2 times, and one time 3 hours, once hour, filter, merging filtrate, being evaporated to does not have the alcohol flavor.Gained medicinal extract no longer detects through AB-8 macroporous adsorbent resin removal of impurities to sugar, use 70% ethanol elution again, the alcohol eluen concentrating under reduced pressure, through polyamide column chromatography aqueous ethanol gradient elution, 70% all flow points of ethanol position (1-2 column volume) eluate concentrating under reduced pressure, the dry thing of gained separates through silica gel column chromatography (wherein silica gel is with the 200-300 order), 0.2) with ethyl acetate-butanone (or acetone)-formic acid-water (6: 2: 1: wash-out such as, get the Quercetin 3-galactoside powder, purity is all greater than 95% (through high performance liquid chromatography, normalization method is measured).
Claims (3)
1. method of separating Quercetin 3-galactoside, it is characterized in that getting Howthorn Leaf or Fruit of Pashi Pear leaf, doubly measure with 16-24, concentration is aqueous ethanol refluxing extraction 2-3 time of 30-80% with the mass percent, the each extraction 1-3 hour, extracting liquid filtering, merging filtrate, concentrating under reduced pressure reclaim ethanol to there not being the alcohol flavor, again through AB-8 or the removal of impurities of D101 macroporous adsorbent resin, with concentration is that the 30-80% ethanol elution is to no longer detecting till the flavones, this elutriant concentrating under reduced pressure reclaims ethanol and does not distinguish the flavor of to there being alcohol, drying, and the dry thing of gained separates through polyamide column chromatography, use the 30-80% ethanol gradient elution, consumption be column volume 3-4 doubly, elutriant is evaporated to dried, the dry thing of gained separates through 200-300 order silica gel column chromatography, with ethyl acetate-butanone or acetone-formic acid-water elution, directly obtain the Quercetin 3-galactoside powder at last.
2. a kind of method of separating Quercetin 3-galactoside according to claim 1, the proportioning that it is characterized in that ethyl acetate-butanone or acetone-formic acid-water is 6: 2: 1: 0.2.
3. a kind of method of separating Quercetin 3-galactoside according to claim 1 is characterized in that gained Quercetin 3-galactoside purity is 90-99%.
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| CN201010158044.9A CN102234299B (en) | 2010-04-28 | 2010-04-28 | Separation method of hyperin |
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| CN201010158044.9A CN102234299B (en) | 2010-04-28 | 2010-04-28 | Separation method of hyperin |
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| CN102234299A true CN102234299A (en) | 2011-11-09 |
| CN102234299B CN102234299B (en) | 2014-10-08 |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104311615A (en) * | 2014-09-30 | 2015-01-28 | 西北师范大学 | Method for extracting and separating hyperoside and gossypetin-3-O-beta-D-galactoside from rhododendron przewalskii maxim. leaves |
| CN106866760A (en) * | 2017-04-11 | 2017-06-20 | 广西壮族自治区梧州食品药品检验所 | A kind of method that ASE methods extract Hyperoside in hawthorn |
| CN112675228A (en) * | 2021-01-18 | 2021-04-20 | 南京邮电大学 | Ointment for promoting wound healing and preparation method thereof |
Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2627721A1 (en) * | 1975-06-21 | 1976-12-30 | Dso Pharmachim | PROCESS FOR PRODUCING A TOTAL FLAVONOID MIXTURE FROM VEGETABLE MATERIAL |
| CN1062294A (en) * | 1991-12-11 | 1992-07-01 | 陕西省西安植物园 | Extract the method for Fructus Crataegi total flavones by Folium Crataegi |
| JPH05268920A (en) * | 1992-02-13 | 1993-10-19 | Toyo Riken Kk | Health food and health drink |
| CN1785285A (en) * | 2004-12-10 | 2006-06-14 | 天津天士力现代中药资源有限公司 | Extraction method of hawthorn lenf |
| CN101161269A (en) * | 2006-10-12 | 2008-04-16 | 黄振华 | Pharmaceutical composition of cattail pollen or its extract and hawkthorn leaf or its extract |
| CN101260133A (en) * | 2008-04-17 | 2008-09-10 | 中国科学院新疆理化技术研究所 | Method for preparing hyperoside and isoquercetin from cotton petal |
| CN100484948C (en) * | 2007-05-10 | 2009-05-06 | 辽宁中医药大学 | Method for separating derivative of vitexin |
| CN101463025A (en) * | 2007-12-20 | 2009-06-24 | 神威药业有限公司 | Extracting preparation of hawthorn leaves flavonoids |
-
2010
- 2010-04-28 CN CN201010158044.9A patent/CN102234299B/en not_active Expired - Fee Related
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2627721A1 (en) * | 1975-06-21 | 1976-12-30 | Dso Pharmachim | PROCESS FOR PRODUCING A TOTAL FLAVONOID MIXTURE FROM VEGETABLE MATERIAL |
| CN1062294A (en) * | 1991-12-11 | 1992-07-01 | 陕西省西安植物园 | Extract the method for Fructus Crataegi total flavones by Folium Crataegi |
| JPH05268920A (en) * | 1992-02-13 | 1993-10-19 | Toyo Riken Kk | Health food and health drink |
| CN1785285A (en) * | 2004-12-10 | 2006-06-14 | 天津天士力现代中药资源有限公司 | Extraction method of hawthorn lenf |
| CN101161269A (en) * | 2006-10-12 | 2008-04-16 | 黄振华 | Pharmaceutical composition of cattail pollen or its extract and hawkthorn leaf or its extract |
| CN100484948C (en) * | 2007-05-10 | 2009-05-06 | 辽宁中医药大学 | Method for separating derivative of vitexin |
| CN101463025A (en) * | 2007-12-20 | 2009-06-24 | 神威药业有限公司 | Extracting preparation of hawthorn leaves flavonoids |
| CN101260133A (en) * | 2008-04-17 | 2008-09-10 | 中国科学院新疆理化技术研究所 | Method for preparing hyperoside and isoquercetin from cotton petal |
Non-Patent Citations (6)
| Title |
|---|
| 《天津中医药》 20090831 郝彧 等 "大孔树脂纯化山楂叶提取物的工艺考察" 第335-337页 1-3 第26卷, 第4期 * |
| 《植物学报》 19810930 谢玉如 等 "山里红的成分分析及国产山楂属植物果实的比较" 第383-388页 1-3 第23卷, 第5期 * |
| 《药学学报》 20011231 张培成 等 "山楂叶化学成分研究" 754-757 1-3 第36卷, 第10期 * |
| 张培成 等: ""山楂叶化学成分研究"", 《药学学报》 * |
| 谢玉如 等: ""山里红的成分分析及国产山楂属植物果实的比较"", 《植物学报》 * |
| 郝彧 等: ""大孔树脂纯化山楂叶提取物的工艺考察"", 《天津中医药》 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104311615A (en) * | 2014-09-30 | 2015-01-28 | 西北师范大学 | Method for extracting and separating hyperoside and gossypetin-3-O-beta-D-galactoside from rhododendron przewalskii maxim. leaves |
| CN106866760A (en) * | 2017-04-11 | 2017-06-20 | 广西壮族自治区梧州食品药品检验所 | A kind of method that ASE methods extract Hyperoside in hawthorn |
| CN112675228A (en) * | 2021-01-18 | 2021-04-20 | 南京邮电大学 | Ointment for promoting wound healing and preparation method thereof |
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| CN102234299B (en) | 2014-10-08 |
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Granted publication date: 20141008 Termination date: 20170428 |