CN103012072A - Technology for preparing high-purity honokiol and magnolol - Google Patents
Technology for preparing high-purity honokiol and magnolol Download PDFInfo
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- CN103012072A CN103012072A CN2013100001743A CN201310000174A CN103012072A CN 103012072 A CN103012072 A CN 103012072A CN 2013100001743 A CN2013100001743 A CN 2013100001743A CN 201310000174 A CN201310000174 A CN 201310000174A CN 103012072 A CN103012072 A CN 103012072A
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Abstract
The invention discloses a technology for preparing high-purity honokiol and magnolol, which comprises the following steps: 1) under certain conditions, sufficiently dissolving Magnolia officinalis total phenol in an organic acid or strongly alkaline solution, and enabling magnolol in the total phenol to be subjected to esterification reaction or acid-base reaction; 2) under certain conditions, standing the solution until crystals are sufficiently precipitated, performing centrifugal separation to obtain high-purity honokiol, and simultaneously collecting the centrifugate; 3) adding an acidic solution into the centrifugate until the pH value indicates acidity and settlings are sufficiently precipitated; and 4) dissolving the settlings in organic solvent while heating, and then cooling to recrystallize, thus obtaining crystals which are high-purity magnolol. The method disclosed by the invention has the advantages of environment friendliness, high safety, high product purity, high yield, simple process and the like, and is suitable for popularization.
Description
Technical field
The present invention relates to medicinal plant single active ingredient technology of preparing, particularly a kind of high purity Honokiol and magnolol technology of from magnolia bark total-phenol, preparing.
Background technology
Magnolol (Magnolol) is the main chemical compositions of Cortex Magnoliae Officinalis with Honokiol (Honokiol).The bark of official magnolia is the dry bark of the Magnoliacea plant bark of official magnolia, is one of important traditional Chinese medicine of China, has following drug effect: (1) relieving distension by promoting circulation of QI: be used for abdominal distension or pain and distention of the abdomen, the distending pain tenderness; (2) eliminating dampness in the temperature: the wrist distention and fullness in the abdomen, the vomiting that are used for turbid damp obstructing in middle-JIAO are had loose bowels; (3) lowering the adverse QI to relieve asthma: be used for coughing of abnormal rising of lung-QI and breathe heavily.A large amount of effective constituents that studies show that the bark of official magnolia are magnolol and Honokiol.Modern pharmacological research shows that magnolol has significant anti-microbial activity to gram-positive bacteria, acid resistance bacterium, filamentous fungus, and streptococcus mutans is had more significant anti-microbial effect, and is the strongest to staphylococcic restraining effect; Honokiol exists huge potentiality aspect antineoplaston simultaneously, from present research situation, the antitumor action of Honokiol has many target spots, too many levels, the characteristics of manifold effect, and toxic side effect is low, the good news is that more it not only has obvious cytotoxicity to common tumour cell, have the tumour cell (such as multiple myeloma cells) of drug resistance also to show certain result for the treatment of for some.
The separating and purifying technology of at present research of Magnolol and Honokiol being reported mainly is to use the organic solvent recrystallization method, and macroreticular resin absorbing method, TLC prepare partition method, high-speed counter-current extraction process, silica gel column chromatography, HPLC preparation etc.The organic solvent recrystallization method is used comparatively extensive, but because organic solvent toxicity is large, and product contains dissolvent residual, consumes simultaneously volumetric quantity repeatedly transfers large and a large amount of solvents and have very large potential safety hazard; High-speed counter-current extraction process equipment is comparatively expensive, and early investment is larger, and cost is too high, and operation sequence is comparatively complicated, and large-scale industrial production is difficult for realizing; Silica gel column chromatography has good separating effect to effective constituent, the characteristics that the product yield is high, but large-scale industrial production is difficult to realize; Though Amberlyst process can be realized suitability for industrialized production, the cycle is longer, and cost is higher.TLC and HPLC method are only suitable in a small amount of preparation in laboratory and detect, and can not be used for the production application of heavy industrialization.
Summary of the invention
The object of the invention is to for the deficiencies in the prior art, utilize Magnolol and Honokiol hydroxyl substituent position different, variant this characteristic of dissociation degree that causes both provides the technology of preparing of high-purity magnolia bark phenol and the Honokiol extract of a kind of high yield, low cost, the simple easy handling of operation.
Technical scheme of the present invention is as follows:
A kind of high-purity Honokiol and magnolol technology of preparing may further comprise the steps:
1) with magnolia bark total-phenol certain amount of organic acid solution or basic solution, pH 5～13, and 40 ℃～55 ℃ of temperature are heated to fully dissolving;
2) under 5 ℃～10 ℃ temperature, placed 4～6 hours, treat that the pH value is pH 7～11 o'clock, after crystal was fully separated out, centrifuging namely got the high purity Honokiol, collected simultaneously centrifugate;
3) certain density hydrochloric acid or citric acid solution are added in the centrifugate, will transfer to about 4～6 from the pH value, after precipitation is separated out fully, centrifuging, centrifugate discards;
4) fully dissolve precipitate with the organic solvent heating, recrystallization makes high-purity magnolia bark phenol.
Principle of the present invention is:
Main component is Magnolol and Honokiol in the magnolia bark total-phenol, and both chemical property are close, mix easily during crystallization.Because both hydroxyl substituent positions are different, cause both hydroxyl dissociation degree difference.Under certain condition, the magnolol hydroxyl is easy to dissociate, by esterification or acid-base neutralisation reaction, become ester or salify so that its solvability changes, soluble in water, and the Honokiol hydroxyl ability of dissociating is substantially weaker than magnolol, utilizes both dissociation degree difference, can separation and purification obtain the high purity Honokiol.Simultaneously because, esterification and acid-base reaction are reversible, by adding acidic solution, after the pH value transferred to acidity, become the magnolol of ester or salify can go to dissociate, again form hydroxyl, its physico-chemical property is recovered, and behind the organic solvent recrystallization, can make high-purity magnolia bark phenol.
The invention has the advantages that:
1, can prepare highly purified Magnolol and Honokiol, improve bark of official magnolia value-added content of product;
2, need not to use that toxicity is large, the organic solvent of high volatility, product no solvent residue, separation and purification process green safety;
3, the separation purifying technique step is simple, and the product yield is high, and production cost is low.
Embodiment
Embodiment 1:
Add certain density gluconic acid solution, magnolia bark total-phenol is fully dissolved, the pH value is 6.5, and Heating temperature is 60 ℃, makes the magnolol esterification complete.Under 5 ℃～10 ℃ low temperature, placed this solution 4-5 hour, the pH value is 7, after crystal was separated out fully, centrifuging namely got the high purity Honokiol, collects simultaneously centrifugate.Add certain density hydrochloric acid soln, centrifugate pH value transferred to about 4, precipitation is separated out fully after, add certain density ethanolic soln, under 55 ℃, fully dissolve this precipitate after, temperature is transferred to 0 ℃～-5 ℃, recrystallization, centrifuging namely gets high-purity magnolia bark phenol.
Embodiment 2:
Add certain density acetic acid solution, magnolia bark total-phenol is fully dissolved, the pH value is 5, and Heating temperature is 50 ℃, makes the magnolol esterification complete.Under 5 ℃～10 ℃ low temperature, placed this solution 4～5 hours, the pH value is 7, after crystal was separated out fully, centrifuging namely got the high purity Honokiol, collects simultaneously centrifugate.Add certain density hydrochloric acid soln, centrifugate pH value transferred to about 4, precipitation is separated out fully after, add certain density ethanolic soln, under 55 ℃, fully dissolve this precipitate after, temperature is transferred to 0 ℃～-5 ℃, recrystallization, centrifuging namely gets high-purity magnolia bark phenol.
Embodiment 3:
Add certain density citric acid solution, magnolia bark total-phenol is fully dissolved, the pH value is 6.5, and Heating temperature is 55 ℃, makes the magnolol esterification complete.Under 5 ℃～10 ℃ low temperature, placed this solution 4～5 hours, the pH value is 7, after crystal was separated out fully, centrifuging namely got the high purity Honokiol, collects simultaneously centrifugate.Add certain density hydrochloric acid soln, centrifugate pH value transferred to about 4, precipitation is separated out fully after, add certain density ethanolic soln, under 55 ℃, fully dissolve this precipitate after, temperature is transferred to 0 ℃～-5 ℃, recrystallization, centrifuging namely gets high-purity magnolia bark phenol.
Embodiment 4:
Add certain density sodium hydroxide solution, magnolia bark total-phenol is fully dissolved, the pH value is 13, and Heating temperature is 40 ℃, makes the magnolol acid-base reaction complete.Under 5 ℃ of low temperature, placed this solution 4～5 hours, the pH value is 10～11, after crystal was separated out fully, centrifuging namely got high-purity magnolia bark phenol, collects simultaneously centrifugate.Add certain density citric acid solution, centrifugate pH value transferred to about 5, precipitation is separated out fully after, add certain density ethanolic soln, under 55 ℃, fully dissolve this precipitate after, temperature is transferred to 0 ℃～-5 ℃, recrystallization, centrifuging namely gets high-purity magnolia bark phenol.
Embodiment 5:
Add certain density potassium hydroxide solution, magnolia bark total-phenol is fully dissolved, the pH value is 13, and Heating temperature is 40 ℃, makes the magnolol acid-base reaction complete.Under 5 ℃ of low temperature, placed this solution 4～5 hours, the pH value is 10～11, after crystal was separated out fully, centrifuging namely got high-purity magnolia bark phenol, collects simultaneously centrifugate.Add certain density citric acid solution, centrifugate pH value transferred to about 5, precipitation is separated out fully after, add certain density ethanolic soln, under 55 ℃, fully dissolve this precipitate after, temperature is transferred to 0 ℃～-5 ℃, recrystallization, centrifuging namely gets high-purity magnolia bark phenol.
Embodiment 6:
Add certain density ammonia soln, magnolia bark total-phenol is fully dissolved, the pH value is 12, and Heating temperature is 45 ℃, makes the magnolol acid-base reaction complete.Under 5 ℃ of low temperature, placed this solution 4～5 hours, the pH value is 10～11, after crystal was separated out fully, centrifuging namely got high-purity magnolia bark phenol, collects simultaneously centrifugate.Add certain density citric acid solution, centrifugate pH value transferred to about 5, precipitation is separated out fully after, add certain density ethanolic soln, under 55 ℃, fully dissolve this precipitate after, temperature is transferred to 0 ℃～-5 ℃, recrystallization, centrifuging namely gets high-purity magnolia bark phenol.
Claims (7)
1. a high-purity Honokiol and magnolol technology of preparing is characterized in that, may further comprise the steps:
1) magnolia bark total-phenol is dissolved in organic acid or the alkaline solution, and, carries out esterification or acid-base reaction under certain condition, make the magnolol in total phenol become the ester salify;
2), place this solution under certain condition, treat that crystal fully separates out;
3) centrifugal, crystal is the high purity Honokiol, collects simultaneously centrifugate;
4) add acidic solution in centrifugate, adjust pH fully separates out precipitation, centrifugal collection precipitate to acid;
5) add organic solvent to precipitate, heating is fully dissolved it, the rear recrystallization of concentrated, cooling, and crystal namely gets high-purity magnolia bark phenol.
2. a kind of high-purity Honokiol according to claim 1 and magnolol technology of preparing is characterized in that described 1) organic acid is gluconic acid, acetic acid, citric acid in the step, alkali is sodium hydroxide, potassium hydroxide, ammoniacal liquor.
3. a kind of high-purity Honokiol according to claim 1 and magnolol technology of preparing is characterized in that described 1) certain condition is pH 5～13 in the step, 40 ℃～55 ℃ of temperature, magnolia bark total-phenol content is more than 80%.
4. a kind of high-purity Honokiol according to claim 1 and magnolol technology of preparing is characterized in that described 2) certain condition is pH 7～11 in the step, 5 ℃～10 ℃ of temperature.
5. a kind of high-purity Honokiol according to claim 1 and magnolol technology of preparing is characterized in that described 3) in the step Honokiol purity greater than 90%.
6. a kind of high-purity Honokiol according to claim 1 and magnolol technology of preparing is characterized in that described 4) pH transfers to 4～6 in the step.
7. a kind of high-purity Honokiol according to claim 1 and magnolol technology of preparing is characterized in that described 5) recrystallization makes magnolol purity greater than 90% in the step.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106588580A (en) * | 2016-11-23 | 2017-04-26 | 成都金瑞基业生物科技有限公司 | Method for preparing high-purity magnolol from Mangnolia officinalis |
| CN108456132A (en) * | 2018-06-07 | 2018-08-28 | 南宁辰康生物科技有限公司 | A kind of method of Magnolol and Honokiol extraction and separation |
| CN112778098A (en) * | 2020-12-31 | 2021-05-11 | 成都金瑞基业生物科技有限公司 | Honokiol crystal form, amorphous form and preparation method thereof |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20080016269A (en) * | 2006-08-18 | 2008-02-21 | 주식회사 유니젠 | Manufacturing process of high purity honokiol, magnolol and extract |
| CN101759532A (en) * | 2009-12-31 | 2010-06-30 | 浙江工业大学 | Method for extracting magnolol and honokiol from magnolia officinalis |
| CN102531850A (en) * | 2010-12-09 | 2012-07-04 | 长沙蕴茵生物科技有限公司 | High-purity magnolol and preparation technology thereof |
-
2013
- 2013-01-04 CN CN2013100001743A patent/CN103012072A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20080016269A (en) * | 2006-08-18 | 2008-02-21 | 주식회사 유니젠 | Manufacturing process of high purity honokiol, magnolol and extract |
| CN101759532A (en) * | 2009-12-31 | 2010-06-30 | 浙江工业大学 | Method for extracting magnolol and honokiol from magnolia officinalis |
| CN102531850A (en) * | 2010-12-09 | 2012-07-04 | 长沙蕴茵生物科技有限公司 | High-purity magnolol and preparation technology thereof |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106588580A (en) * | 2016-11-23 | 2017-04-26 | 成都金瑞基业生物科技有限公司 | Method for preparing high-purity magnolol from Mangnolia officinalis |
| CN108456132A (en) * | 2018-06-07 | 2018-08-28 | 南宁辰康生物科技有限公司 | A kind of method of Magnolol and Honokiol extraction and separation |
| CN112778098A (en) * | 2020-12-31 | 2021-05-11 | 成都金瑞基业生物科技有限公司 | Honokiol crystal form, amorphous form and preparation method thereof |
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Application publication date: 20130403 |