CN100387588C - Method for distilling myricetin from plant - Google Patents
Method for distilling myricetin from plant Download PDFInfo
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- CN100387588C CN100387588C CNB2005100348241A CN200510034824A CN100387588C CN 100387588 C CN100387588 C CN 100387588C CN B2005100348241 A CNB2005100348241 A CN B2005100348241A CN 200510034824 A CN200510034824 A CN 200510034824A CN 100387588 C CN100387588 C CN 100387588C
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Abstract
The present invention relates to a method for extracting myricetin from vegetable materials, more specifically a method for extracting and separating myricetin from Chinese waxmyrtle bark and yao nationality vine tea plants. The present invention belongs to a technique for preparing flavonoid myricetin from natural plant. The method comprises the steps: after ethanol solution is used for extraction, medium polar organic solvents are used for extraction; the obtained myricetin crude product is absorbed by polyamide or polar macroporous resin for elution and separation. The yield of the method is high, and the separation procedure is simple, and the product purity is high, the myricetin content is more than or equal to 80%, and the myricetin is suitable for large-scale batch production.
Description
Affiliated technical field
The present invention relates to extract from plant material the method for myricetin, belong to the technology of preparation flavonoid compound myricetin from natural phant, specifically is the method for extraction separation myricetin from Cortex Myricae Rubrae and Yao nationality vine tea plant.
Background technology
Myricetin (Myricetin) is a contained myricetin constituents in the bark of Myruca ceas red bayberry spp.ing plant red bayberry (Myrica rubra (Lour.) Sieb.et Zucc.) or Vitaceae ampelopsis Ampelopsis grossedentata (the Ampelossis cantoniensis planch.Var.grossedetala Hand-Mazz) cauline leaf (having another name called Yao nationality's vine tea), has significant physiologically actives such as protecting liver, lowering enzymes, removing jaundice, raising immunologic function, hypoglycemic, anti-PAF.At basic unit's Chinese medicine magazine, 1999,13 (46): the structure that discloses myricetin in 6 documents is as follows:
Myricetin is 3,5,7,3 ', 4 ', and 5 '-quercetagetin has the phenolic acid structure, is soluble in methyl alcohol, ethanol, acetone, can be dissolved in vinyl acetic monomer, is insoluble in water.
Except that myricetin, also contain dihydromyricetin, Hairy Waxmyrtle glucoside, cannabin, tannin etc. in the Cortex Myricae Rubrae; Except that myricetin, also contain compositions such as a large amount of dihydromyricetins and chlorophyll in Yao nationality's vine tea.Because the content of myricetin in Cortex Myricae Rubrae and Yao nationality's vine tea is lower, be subject to the interference of the interference, particularly dihydromyricetin of other composition, this has just brought certain difficulty for the purification myricetin.At present, the method that bibliographical information extracts myricetin has: at basic unit's Chinese medicine magazine, 1999,13 (46): disclose from the Yao nationality's vine tea method of extracting, separating myricetin in 6, it is with using extraction using alcohol behind the petroleum ether degreasing, and recycle silicon glue chromatography column separates, and this method cost is high, only be applicable to laboratory study, be not suitable for the batch process of mass-producing; Use pharmaceutical journal at contemporary Chinese; 2000; 17 (3): the disclosed method of from Yao nationality's vine tea, extracting, separating myricetin in 196; it is with behind the water extraction; method with solvent repeated multiple times recrystallization; the yield of this method is lower, and only 0.51% (by crude drug weight) does not therefore also have at present the report that a kind of comparison is effective, be applicable to the Technology of mass-producing batch process extraction myricetin.
Summary of the invention
The purpose of this invention is to provide a kind of is the method that raw material extracts myricetin from plant Cortex Myricae Rubrae and Vitaceae ampelopsis Ampelopsis grossedentata cauline leaf, produces myricetin in batches to be applicable to mass-producing.
The present invention is according to the myricetin characteristics of molecular structure, have characteristics in its molecule than the phenolic hydroxyl group of high polarity, utilize these polar groups, adopt organic solvent extraction, method with polymeric amide or polar macroporous resin absorption, pure dissolubility myricetin is carried out fractionation by adsorption effectively, the purpose of remove impurity to reach, separating the purification myricetin.Elutriant reclaim under reduced pressure alcoholic solution can be separated out the higher myricetin of purity.
The method of extracting myricetin from plant material Cortex Myricae Rubrae and Vitaceae ampelopsis Ampelopsis grossedentata cauline leaf provided by the present invention, adopt following steps:
One, extract: extract (1): with Cortex Myricae Rubrae or Ampelopsis grossedentata cauline leaf is raw material, adopts 70～95% conventional ethanolic solns to extract, and obtains extracting solution; Extracting solution decompression and solvent recovery after drying, and pulverizing is dried cream powder;
(2) extract: dried cream powder is added the organic solvent of the middle polarity of 4～12 times of amounts, and heating and refluxing extraction 1～3 time is filtered, and merging filtrate when filtrate decompression is recycled to 0.4～1.2 times that is equivalent to raw material weight, leaves standstill more than 8 hours again.Here the organic solvent of said middle polarity can be acetone, vinyl acetic monomer, ethanol, methyl alcohol or the mixed solvent more than 2 kinds, is good to adopt acetone, vinyl acetic monomer.
(3) filtering and concentrating: the solution after will leaving standstill filters, and filtrate decompression reclaims after drying, must contain the crude product of myricetin;
Two, separate: (1) upper prop: the myricetin crude product is added 60～95% dissolve with ethanol solution, add water again and adjust alcohol concn to 30～35%, filter, filtrate is made the adsorption column of sorbent material and is adsorbed with having filled polymeric amide or polar macroporous resin, is good to adopt the polymeric amide sorbent material preferably;
(2) wash-out: after waiting to adsorb, carry out wash-out with 20～40% ethanol liquid, discard elutriant, continuous ethanolic soln with 50～80% carries out wash-out, collects elutriant;
(3) behind the elutriant decompression recycling ethanol, separate out highly purified myricetin, filter, collecting precipitation, dry under 50 ℃, promptly get myricetin, the content of its myricetin 〉=80%.
The myricetin product that is obtained, after the repurity, measure and contrast with the myricetin reference substance through infrared spectra (IR), UV spectrum (UV), nuclear magnetic resonance spectrum (HNMR), mass spectrum (MS) etc., the product that proves gained is a myricetin, adopt the method for high performance liquid chromatography, reference drug is analyzed magazine, 2002,22 (1): 31 testing method, the result shows, the Cortex Myricae Rubrae cellulose content can reach more than 80%, and average yield is about 1.2%, even can reach 1.9%.
The superiority of method provided by the present invention is: preparation technology is simple, and raw material is easy to get, and separation and purification of products is convenient, and the product purity of gained is higher, and production cost is low, and the yield height is suitable for suitability for industrialized production.
Further narrate technical scheme of the present invention below in conjunction with specific embodiment.
Embodiment:
Embodiment 1, get the 1.5kg Cortex Myricae Rubrae and be ground into meal, add 95% ethanol 1500ml reflux, each 2 hours, extract altogether 3 times, merging filtrate, filtrate is concentrated to dried, extract refluxes 2 times with vinyl acetic monomer 1500ml, each 1 hour, filters, merging filtrate, reclaim solvent to about 750ml, left standstill 8 hours, filter, filtrate decompression is recycled to dried, gets the myricetin crude product.The myricetin crude product added 70% dissolve with ethanol, add water again and adjust alcohol concn to 35%, filter, filtrate is adsorbed with the adsorption column of having filled 30～60 order polymeric amide, after waiting to adsorb, carry out wash-out, discard elutriant with 35% ethanolic soln, continuous ethanolic soln with 65% carries out wash-out, collects elutriant.Behind the elutriant decompression recycling ethanol, separate out highly purified myricetin, filter, collecting precipitation is also dry under 50 ℃, promptly gets myricetin product 17.5g, yield 1.17%.Product is measured through the HPLC method, and the content that records myricetin is 85.7%, and HPLC method measuring method is by pharmaceutical analysis magazine, 2002,22 (1): 31 test determines.
Embodiment 2, get 2kg Yao nationality vine tea cauline leaf and be ground into meal, add 85% ethanol 2000ml reflux, each 2 hours, extract altogether 3 times, merging filtrate, filtrate is concentrated into dried, extract refluxes 2 times with vinyl acetic monomer 2000ml, each 1 hour, filters, merging filtrate, reclaim solvent to about 1000ml, standing over night is filtered, filtrate decompression is recycled to dried, gets the myricetin crude product.The myricetin crude product is added 80% dissolve with ethanol, add water again and adjust alcohol concn to 30%, filter, filtrate is adsorbed with the adsorption column of having filled polymeric amide, after waiting to adsorb, carries out wash-out with 30% ethanol liquid, discard elutriant, continuous ethanolic soln with 70% carries out wash-out, collects elutriant.Behind the elutriant decompression recycling ethanol, separate out highly purified myricetin, filter, collecting precipitation is also dry under 50 ℃, promptly gets the myricetin product 25.1g of higher degree, and yield is 1.26%.Product is measured through the HPLC method, and the content that records myricetin is 80.4%.
Embodiment 3, get the 1.5kg Cortex Myricae Rubrae and be ground into meal, add 70% ethanol 1500ml reflux, each 2 hours, extract altogether 3 times, merging filtrate, filtrate is concentrated into dried, extract refluxes 2 times with vinyl acetic monomer 1500ml, each 1 hour, filters, merging filtrate, reclaim solvent to about 750ml, left standstill 10 hours, filter, filtrate decompression is recycled to dried, gets the myricetin crude product.The myricetin crude product added 80% dissolve with ethanol, add water again and adjust alcohol concn to 35%, filter, filtrate is adsorbed with the adsorption column of having filled the D101 macroporous adsorbent resin, after waiting to adsorb, carry out wash-out, discard elutriant with 38% ethanol liquid, continuous ethanolic soln with 75% carries out wash-out, collects elutriant.Behind the elutriant reclaim under reduced pressure alcoholic solution, separate out highly purified myricetin, filter, collecting precipitation is also dry under 50 ℃, promptly gets the myricetin product 17.8g of higher degree, and yield is 1.9%.Product is measured through the HPLC method, and the content that records myricetin is 80.1%.
Embodiment 4:
Get the 1.5kg Cortex Myricae Rubrae and be ground into meal, add 75% ethanol 1500ml reflux, each 2 hours, extract altogether 3 times, merging filtrate, filtrate is concentrated into dried, extract refluxes 2 times with acetone 1500ml, each 1 hour, filters, merging filtrate, reclaim solvent to about 750ml, left standstill 12 hours, filter, filtrate decompression is recycled to dried, gets the myricetin crude product.The myricetin crude product added 80% dissolve with ethanol, add water again and adjust alcohol concn to 35%, filter, filtrate is adsorbed with having filled D101 macroporous resin absorption post, after waiting to adsorb, carry out wash-out, discard elutriant with 38% ethanol liquid, continuous ethanolic soln with 75% carries out wash-out, collects elutriant.Behind the elutriant reclaim under reduced pressure alcoholic solution, separate out highly purified myricetin, filter, collecting precipitation is also dry under 50 ℃, promptly gets the myricetin product 12.3g of higher degree, yield 0.82%.Product is measured through the HPLC method, and the content that records myricetin is 79.7%.
Claims (3)
1. a method of extracting myricetin from plant Myruca ceas myrica Cortex Myricae Rubrae or Vitaceae Ampelopsis Ampelopsis grossedentata cauline leaf is characterized in that this method comprises the steps:
One, extract: extract (1): with Cortex Myricae Rubrae or Ampelopsis grossedentata cauline leaf is raw material, adopts 70～95% conventional ethanolic solns to extract, and obtains extracting solution; Extracting solution decompression and solvent recovery after drying, and pulverizing is dried cream powder;
(2) extract: dried cream powder is added the organic solvent of the middle polarity of 4～12 times of amounts, and heating and refluxing extraction 1～3 time is filtered, and merging filtrate when filtrate decompression is recycled to 0.4～1.2 times that is equivalent to raw material weight, leaves standstill more than 8 hours again;
(3) filtering and concentrating: the solution after will leaving standstill filters, and filtrate decompression reclaims the solvent after drying, must contain the crude product of myricetin;
Two, separate: (1) upper prop: the myricetin crude product is added 60～95% dissolve with ethanol solution, add water again and adjust alcohol concn to 30～35%, filter, filtrate is made the adsorption column of sorbent material and is adsorbed with having filled polymeric amide or polar macroporous resin;
(2) wash-out: after waiting to adsorb, carry out wash-out with 20～40% ethanol liquid, discard elutriant, continuous ethanolic soln with 50～80% carries out wash-out, collects elutriant;
(3) behind the elutriant decompression recycling ethanol, separate out highly purified myricetin, filter, collecting precipitation, 50 ℃ are dry down, promptly get myricetin.
2. extraction myricetin method as claimed in claim 1 is characterized in that, one, (2) in extracting extract again: described medium polar solvent is acetone or vinyl acetic monomer.
3. extraction myricetin method as claimed in claim 1 is characterized in that, two, said sorbent material is a polymeric amide during (1) upper prop in separating.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| NL2029678A (en) * | 2021-11-08 | 2022-01-19 | Univ Zhejiang | Method for purifying myricetin from myrica rubra leaf |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101185664B (en) * | 2007-11-30 | 2011-09-07 | 南京大学 | Waxberry fruit extract, its preparation method and its application of protecting liver |
| CN101838255B (en) * | 2010-05-07 | 2013-06-26 | 湖州四丰生物科技有限公司 | Myricetin extraction process |
| CN101973976B (en) * | 2010-09-16 | 2012-01-18 | 湖北民族学院 | Method for extracting dihydromyricetin, ampelopsis grossedentata amylase and ampelopsis grossedentata polyphenol from ampelopsis grossedentata |
| CN102106931B (en) * | 2010-12-30 | 2013-03-20 | 张家界茅岩莓有限公司 | Method for producing diverse extracts of berry tea |
| CN103242697A (en) * | 2013-05-24 | 2013-08-14 | 天津天康源生物技术有限公司 | Edible printing ink and preparation method thereof |
| CN104016955B (en) * | 2014-05-23 | 2016-04-06 | 陕西师范大学 | A kind of method being extracted ampelopsin by trifoliate orange seed |
| CN104530749A (en) * | 2014-12-04 | 2015-04-22 | 常州大学 | Method for extracting natural pigment from bark |
| CN107721963A (en) * | 2017-10-19 | 2018-02-23 | 宁波金昉生物科技有限公司 | The method of extraction separation myricetin from Chinese waxmyrtle bark |
| CN110628840B (en) * | 2019-09-05 | 2021-07-30 | 宁波德康生物制品有限公司 | Method for extracting myricetin by microbial fermentation |
| CN110526891A (en) * | 2019-09-17 | 2019-12-03 | 湖北省农业科学院中药材研究所 | A method of texifolin is isolated and purified and identified from vine tea tissue |
| CN110526889A (en) * | 2019-09-17 | 2019-12-03 | 湖北省农业科学院中药材研究所 | A method of myricetin is isolated and purified and identified from vine tea tissue |
| CN110526890A (en) * | 2019-09-17 | 2019-12-03 | 湖北省农业科学院中药材研究所 | A method of dihydromyricetin is isolated and purified and identified from vine tea tissue |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1393443A (en) * | 2001-06-29 | 2003-01-29 | 张友胜 | Process for preparing dihydromyricetin from porcelain ampelopsis |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN1393443A (en) * | 2001-06-29 | 2003-01-29 | 张友胜 | Process for preparing dihydromyricetin from porcelain ampelopsis |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL2029678A (en) * | 2021-11-08 | 2022-01-19 | Univ Zhejiang | Method for purifying myricetin from myrica rubra leaf |
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