CN102267877A - Method for extracting and separating magnolol and honokiol from leaf of magnolia officinalis - Google Patents
Method for extracting and separating magnolol and honokiol from leaf of magnolia officinalis Download PDFInfo
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- CN102267877A CN102267877A CN2011102588616A CN201110258861A CN102267877A CN 102267877 A CN102267877 A CN 102267877A CN 2011102588616 A CN2011102588616 A CN 2011102588616A CN 201110258861 A CN201110258861 A CN 201110258861A CN 102267877 A CN102267877 A CN 102267877A
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Abstract
The invention mainly relates to a method for extracting and separating magnolol and honokiol from the leaf of magnolia officinalis. The method comprises the following steps of: grinding fresh leaf of magnolia officinalis being produced in western Hunan and serving as a raw material, extracting, concentrating, leaching, concentrating and crystallizing to obtain total phenolic; changing recrystallizing condition; and performing filtration and vacuum drying to obtain magnolol and magnolol crystals. In the entire separation process, the requirements on environment condition and equipment are not high, the separation yields of magnolol and honokiol are high, the separation time is shortest, the operation method is simple, the purity is highest, and the comprehensive utilization ratio of the raw material is highest; moreover, a separating material is readily available and cheap, and the separation operation process is simple and is easy to control; and crystallization and recrystallization are adopted, so that the purifying efficiency is high, and the cost is low.
Description
Affiliated technical field:
The invention belongs to the natural product chemistry field, be specifically related to a kind of from the bark of official magnolia leaf method of its main active ingredient magnolol of extraction separation and Honokiol.
Background technology
The bark of official magnolia is a conventional Chinese medicine, derives from dry hide, root skin, the branch skin of the Magnoliacea plant bark of official magnolia, the dissolving phlegm of tool eliminating dampness, and the therapeutic method to keep the adverse qi flowing downward is removed full effect, is used for humidity hysteresis and hinders, and take off ruffian and vomit and diarrhoea, stagnation of QI due to dyspepsia, abdominal distention constipation, phlegm and retained fluid is breathed with cough.Modern pharmacological research shows that the bark of official magnolia has antiviral, and is antitumor, antibiotic, antiulcer agent, spasmolytic, analgesia. anti-inflammatory action, anticaries action, grade of flaccid muscles effect.Contain compositions such as magnolol, Honokiol, tetrahydromagnolol, iso-agnolol in the bark of official magnolia skin, be main active ingredient (structural formula is as follows) wherein with magnolol and Honokiol, they have important use at aspects such as medicines and health protection, daily-use chemical industry, functional food, therefore its consumption is increasing, at present number of research projects has been done in the extraction and the separation and purification of magnolol and Honokiol, mainly contained alkali and carry that acid is heavy, alkali is carried, supercritical CO
2Extraction process, column chromatography method.Adopt alkaline extraction, filtration and subsequent disposal be trouble.Supercritical CO wherein
2The extraction process apparatus expensive, investment is big, and treatment capacity is little, and the disposable content that extracts is not high, and still the same needs carry out subsequent disposal.
Magnolol structural formula Honokiol structural formula
Publication number is that the Chinese patent of CN101857531A has been introduced a kind of method of extracting magnolol and Honokiol from the bark of official magnolia, is that bark of official magnolia skin is pulverized, and uses extraction using alcohol; Cross macroporous resin column, concentrating under reduced pressure, extractive crystallization get the magnolol elaboration.Though extraction can obtain high-load magnolol and Honokiol from the bark of official magnolia (skin), but the bark of official magnolia (skin) itself is a kind of Chinese medicinal materials of widespread use, the bark of official magnolia (skin) growth year is long more, medicinal valency is planted high more, be used to extract the bark of official magnolia (skin) resource-constrained of magnolol and Honokiol, cause magnolol and Honokiol cost very high.In addition, utilize high-load magnolol of bark of official magnolia skin extraction separation and Honokiol all to adopt the post separation method at present, sepn process is comparatively complicated, is unfavorable for suitability for industrialized production.
Magnolol and Honokiol content in bark of official magnolia bark is the highest, but magnolol and Honokiol also have certain content in bark of official magnolia leaf, and winter leaf-fall, draw materials conveniently, resource distribution is extensive, low price.Publication number is that the Chinese patent of CN101947255A has been introduced a kind of bark of official magnolia leaf extract and extracting method thereof, is with bark of official magnolia leaf drying and crushing, uses the ethanol high temperature extraction, concentrates, and crystallization is filtered, and obtains the mixed crystallization thing of magnolol and Honokiol.This method adopts high temperature extraction to cause the aldehydes matter oxidation easily, do not adopt before the crystallization to filter and remove insolubles, work causes great difficulty to later separation, in addition, mainly be the monomer that needs magnolol and Honokiol in the market, not high to the demand of mixture.
Thereby it is significant that bark of official magnolia leaf is carried out comprehensive deep processing, explores and extract magnolol and Honokiol simultaneously from bark of official magnolia leaf, and it is of far-reaching significance.
Summary of the invention
The object of the present invention is to provide a kind of from the bark of official magnolia leaf separation and purification high-content magnolol monomer, Honokiol monomer methods, this method is not high and to have proposed a kind of be that raw material and technology are simple with the leaf in order to overcome the existing raw material difficulty of utilizing bark of official magnolia skin separating and purifying magnolol and Honokiol and technical sophistication and efficient, easy to operate, cost is low, the yield height, resource recovery and be suitable for the production method of large-scale industrialization separation and purification high-content magnolol and Honokiol from bark of official magnolia leaf.
It is simple that the present invention will disclose a kind of technology, easy to operate, cost is low, yield is high and be suitable for the production method of large-scale industrialization extraction separation magnolol and Honokiol from bark of official magnolia leaf, it is a raw material with bark of official magnolia leaf, through rub to extract, concentrate, extraction, condensing crystal get magnolia bark total-phenol, changes the recrystallization condition, after filtration, obtain Honokiol, magnolol crystallisate respectively after the vacuum-drying.
Of the present invention be a kind of from the bark of official magnolia leaf method of extraction separation magnolol and Honokiol, its operation steps is as follows:
(1) with after the rubbing of bark of official magnolia leaf, place high concentration ethanol, 50 ℃ are extracted 3 times, and extraction time is 2h/ time, filters united extraction liquid;
(2) extracting solution reclaims solvent at 50 ℃ of concentrating under reduced pressure, is concentrated into medicinal extract, and medicinal extract extracts 3 times at 50 ℃ with the extraction solvent of 2 times of volumes, and the extraction time is 2h/ time, combining extraction liquid;
(3) the extraction liquid vacuum decompression is concentrated into certain volume, places 24h, and the mixed crystallization thing A (being magnolia bark total-phenol) that obtains faint yellow magnolol and Honokiol is filtered in crystallization;
(4) mixed crystallization thing A dissolves with hexanaphthene, and its solvent temperature is that 50 ℃, dissolution time are 1h.Behind the crystallizing at room temperature 24h, filter, vacuum-drying gets crystallisate B (being white Honokiol);
(5) after the filtrate vacuum decompression is concentrated into certain volume, after room temperature is placed 24h, filter, get filter residue.After dissolving this filter residue with methylene dichloride, crystallizing at room temperature 24h filters, and vacuum-drying gets crystallisate C (being white magnolol).
In one embodiment, raw material described in the step 1 is fresh bark of official magnolia leaf, used extraction solution is the aqueous ethanolic solution of 70-85%, adding the volume of ethanolic soln and the weight ratio (V/kg) of bark of official magnolia leaf is 8-14: 1, and what filtration procedure adopted is three layers of filtered through gauze 2 times, ceramic membrane filter 1 time.
In one embodiment, the extraction solvent described in the step 2 is a hexanaphthene.
In another embodiment, be concentrated into the 1/4-1/10 volume in the step 3 after, crystallisation process is at room temperature to carry out, filtration procedure is to adopt ceramic membrane filter 1 time.
In another embodiment, the volume of adding hexanaphthene and the weight ratio (V/kg) of crystallisate are 15-25 in the step 4: 1, and filtration procedure is to adopt ceramic membrane filter 1 time.
In another embodiment, be concentrated into original volume 1/8-1/12 in the step 5 after, the volume that adds methylene dichloride is 5-12 with the weight ratio (V/kg) of crystallisate: 1, filtration procedure is employing ceramic membrane filter 1 time.
Technique effect:
1, the present invention compares with existing method, and raw materials used is fresh bark of official magnolia leaf, makes full use of the water in the leaf, reaches the purpose of water saving, does not need in addition raw material is carried out drying, plays energy-conservation effect, again breviaty production process.
2, this method has been avoided the complicated column chromatography technology of adopting process, and countercurrent chromatography adopts crystallization and recrystallization technology, makes simple to operately, greatly reduces the production cost of magnolol and Honokiol, the yield height, and output is big, has also simplified production process.
3, the used raw material of the present invention is a bark of official magnolia leaf, and it is low to measure big cost, has protected the medicine resource of the Chinese bark of official magnolia (skin), has improved its economic benefit.
Description of drawings
Fig. 1, samples contg are 98.8% magnolia bark total-phenol HPLC collection of illustrative plates, and wherein ordinate zou is represented peak area, and X-coordinate is represented disengaging time, and appearance time is a Honokiol about 7.62min, and appearance time is a magnolol about 10.89min.
Fig. 2, samples contg are 98.92% Honokiol HPLC collection of illustrative plates, and wherein ordinate zou is represented peak area, and X-coordinate is represented disengaging time.
Fig. 3, samples contg are 99.13% magnolol HPLC collection of illustrative plates, and wherein ordinate zou is represented peak area, and X-coordinate is represented disengaging time.
Embodiment
Below in conjunction with accompanying drawing, further specify essentiality content of the present invention with embodiment of the present invention, but do not limit the present invention with this.
Embodiment 1
Take by weighing the fresh bark of official magnolia leaf (it is 2.2% that the HPLC method is measured Honokiol content, and magnolol content is 1.4%) of 100Kg, rub, place 1000L (V/V) in 80% ethanol, 50 ℃ are extracted 3 times, and extraction time is 2h/ time, filters united extraction liquid; Extracting solution concentrates under-the 0.09MPa 50 ℃ and vacuum tightness, reclaims solvent, is concentrated into medicinal extract 30kg, and 50 ℃ of extractions 3 times, the extraction time is 2h/ time to medicinal extract, combining extraction liquid with the 60L hexanaphthene; The extraction liquid vacuum decompression is concentrated into 15L, and crystallizing at room temperature 24h filters mixed crystallization thing A (the being magnolia bark total-phenol) 3.5kg that obtains faint yellow magnolol and Honokiol.Mixed crystallization thing A is with the dissolving of 70L hexanaphthene, and solvent temperature is that 50 ℃, time are 1h, and room temperature is placed crystallization 24h, filters, and vacuum-drying gets crystallisate B (being white Honokiol) 1.9kg; The filtrate vacuum decompression is concentrated into 7.5L, and room temperature is placed 24h, filters, and gets filter residue 1.38kg; Dissolve this filter residue with the 7L methylene dichloride, crystallizing at room temperature 24h filters, and vacuum-drying gets crystallisate C (being white magnolol) 1.24g.Test set is the Agilent1100 high performance liquid chromatograph, chromatographic column is Hypersil ODS (150mm * 4.6mm, 5 μ), testing conditions: moving phase is that 80% methanol in water, detection wavelength are that 292nm, flow velocity are that 0.8ml/min, column temperature are that 30 ℃, sample size are 20 μ L, the content that detects each crystallisate is respectively 98.82% magnolia bark total-phenol, 98.72% Honokiol, 98.93% magnolol.Experimental result sees Table 1, Fig. 1, Fig. 2, Fig. 3.
Embodiment 2
Take by weighing the fresh bark of official magnolia leaf (it is 2.2% that the HPLC method is measured Honokiol content, and magnolol content is 1.4%) of 200Kg, rub, place 2000L (V/V) in 85% ethanol, 50 ℃ are extracted 3 times, and extraction time is 2h/ time, filters united extraction liquid; Extracting solution concentrates under-the 0.09MPa 50 ℃ and vacuum tightness, reclaims solvent, is concentrated into medicinal extract 62kg, and 50 ℃ of extractions 3 times, the extraction time is 2h/ time to medicinal extract, combining extraction liquid with the 130L hexanaphthene; The extraction liquid vacuum decompression is concentrated into 30L, and crystallizing at room temperature 24h filters mixed crystallization thing A (the being magnolia bark total-phenol) 7.8kg that obtains faint yellow magnolol and Honokiol; Mixed crystallization thing A is with the dissolving of 150L hexanaphthene, and solvent temperature is that 50 ℃, time are 1h, and room temperature is placed crystallization 24h, filters, and vacuum-drying gets crystallisate B (being white Honokiol) 4.12kg; The filtrate vacuum decompression is concentrated into 15L, and room temperature is placed 24h, filters, and gets filter residue 2.86kg; Dissolve this filter residue with the 14L methylene dichloride, crystallizing at room temperature 24h filters, and vacuum-drying gets crystallisate C (being white magnolol) 2.52kg.The content that detects each crystallisate by the detection method of embodiment 1 is respectively 98.87% magnolia bark total-phenol, 98.68% Honokiol, 99.13% magnolol.
Embodiment 3
Take by weighing the fresh bark of official magnolia leaf (it is 2.2% that the HPLC method is measured Honokiol content, and magnolol content is 1.4%) of 400Kg, rub, place 4500L (V/V) in 75% ethanol, 50 ℃ are extracted 3 times, and extraction time is 2h/ time, filters united extraction liquid; Extracting solution concentrates under-the 0.09MPa 50 ℃ and vacuum tightness, reclaims solvent, is concentrated into medicinal extract 135kg, and 50 ℃ of extractions 3 times, the extraction time is 2h/ time to medicinal extract, combining extraction liquid with the 300L hexanaphthene; The extraction liquid vacuum decompression is concentrated into 60L, and crystallizing at room temperature 24h filters mixed crystallization thing A (the being magnolia bark total-phenol) 17.6kg that obtains faint yellow magnolol and Honokiol; Mixed crystallization thing A is with the dissolving of 360L hexanaphthene, and solvent temperature is that 50 ℃, time are 1h, and room temperature is placed crystallization 24h, filters, and vacuum-drying gets crystallisate B (being white Honokiol) 8.38kg; The filtrate vacuum decompression is concentrated into 32L, and room temperature is placed 24h, filters, and gets filter residue 6.26kg; Dissolve this filter residue with the 14L methylene dichloride, crystallizing at room temperature 24h filters, and vacuum-drying gets crystallisate C (being white magnolol) 5.25kg.The content that detects each crystallisate by the detection method of embodiment 1 is respectively 98.78% magnolia bark total-phenol, 98.91% Honokiol, 98.84% magnolol.
Embodiment 4
Take by weighing the fresh bark of official magnolia leaf (it is 2.2% that the HPLC method is measured Honokiol content, and magnolol content is 1.4%) of 800Kg, rub, place 9000L (V/V) in 85% ethanol, 50 ℃ are extracted 3 times, and extraction time is 2h/ time, filters united extraction liquid; Extracting solution concentrates under-the 0.09MPa 50 ℃ and vacuum tightness, reclaims solvent, is concentrated into medicinal extract 276kg, and 50 ℃ of extractions 3 times, the extraction time is 2h/ time to medicinal extract, combining extraction liquid with the 550L hexanaphthene; The extraction liquid vacuum decompression is concentrated into 125L, and crystallizing at room temperature 24h filters mixed crystallization thing A (the being magnolia bark total-phenol) 34.5kg that obtains faint yellow magnolol and Honokiol; Mixed crystallization thing A is with the dissolving of 700L hexanaphthene, and solvent temperature is that 50 ℃, time are 1h, and room temperature is placed crystallization 24h, filters, and vacuum-drying gets crystallisate B (being white Honokiol) 17.12kg; The filtrate vacuum decompression is concentrated into 32L, and room temperature is placed 24h, filters, and gets filter residue 12.89kg; Dissolve this filter residue with the 14L methylene dichloride, crystallizing at room temperature 24h filters, and vacuum-drying gets crystallisate C (being white magnolol) 10.95kg.The content that detects each crystallisate by the detection method of embodiment 1 is respectively 98.86% magnolia bark total-phenol, 98.82% Honokiol, 98.78% magnolol.
Claims (6)
1. the invention provides the method for separation and purification Honokiol, magnolol in a kind of bark of official magnolia leaf, step comprises:
(1) with after the rubbing of bark of official magnolia leaf, place high concentration ethanol, 50 ℃ are extracted 3 times, and extraction time is 2h/ time, filters united extraction liquid;
(2) extracting solution reclaims solvent at 50 ℃ of concentrating under reduced pressure, is concentrated into medicinal extract, and medicinal extract extracts 3 times at 50 ℃ with the extraction solvent of 2 times of volumes, and the extraction time is 2h/ time, combining extraction liquid;
(3) the extraction liquid vacuum decompression is concentrated into certain volume, places 24h, and the mixed crystallization thing A (being magnolia bark total-phenol) that obtains faint yellow magnolol and Honokiol is filtered in crystallization;
(4) mixed crystallization thing A dissolves with hexanaphthene, and its solvent temperature is that 50 ℃, dissolution time are 1h.Behind the crystallizing at room temperature 24h, filter, vacuum-drying gets crystallisate B (being white Honokiol);
(5) after the filtrate vacuum decompression is concentrated into certain volume, after room temperature is placed 24h, filter, get filter residue.After dissolving this filter residue with methylene dichloride, crystallizing at room temperature 24h filters, and vacuum-drying gets crystallisate C (being white magnolol).
2. according to the method for claim 1, wherein the described raw material of step 1 is that bark of official magnolia leaf is produced in the fresh western Hunan, Hunan, used extraction solution is the aqueous ethanolic solution of 70-85%, adding the volume of ethanolic soln and the weight ratio (V/kg) of bark of official magnolia leaf is 8-14: 1, and what filtration procedure adopted is three layers of filtered through gauze 2 times, ceramic membrane filter 1 time.
3. according to the method for claim 1 or 2, wherein the extraction solvent described in the step 2 is a hexanaphthene.
4. according to the method for claim 3, wherein be concentrated into the 1/4-1/10 volume in the step 3 after, crystallisation process is at room temperature to carry out, filtration procedure is to adopt ceramic membrane filter 1 time.
5. according to the method for claim 4, wherein adding the volume of hexanaphthene and the weight ratio of crystallisate in the step 4 is 15-25: 1, and filtration procedure is to adopt ceramic membrane filter 1 time.
6. according to the method for claim 5, wherein be concentrated into the 1/8-1/12 volume in the step 5 after, the volume that adds methylene dichloride is 5-12 with the weight ratio of crystallisate: 1, filtration procedure is employing ceramic membrane filter 1 time.
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Cited By (4)
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| CN102408314A (en) * | 2011-12-09 | 2012-04-11 | 广西大学 | Method for preparing high-purity magnolol and magnolol |
| CN102924240A (en) * | 2012-11-20 | 2013-02-13 | 雅安太时生物科技有限公司 | Method for extracting total magnolol according to alcoholic-alkaline method |
| CN108164399A (en) * | 2018-01-31 | 2018-06-15 | 湖南佳沐生物科技有限公司 | A kind of green separation technique that magnolol and honokiol monomer are prepared from magnolia bark raw material |
| CN109627147A (en) * | 2018-11-27 | 2019-04-16 | 中南民族大学 | A kind of honokiol crystal and preparation method thereof |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN102408314A (en) * | 2011-12-09 | 2012-04-11 | 广西大学 | Method for preparing high-purity magnolol and magnolol |
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| CN102924240A (en) * | 2012-11-20 | 2013-02-13 | 雅安太时生物科技有限公司 | Method for extracting total magnolol according to alcoholic-alkaline method |
| CN108164399A (en) * | 2018-01-31 | 2018-06-15 | 湖南佳沐生物科技有限公司 | A kind of green separation technique that magnolol and honokiol monomer are prepared from magnolia bark raw material |
| CN109627147A (en) * | 2018-11-27 | 2019-04-16 | 中南民族大学 | A kind of honokiol crystal and preparation method thereof |
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Application publication date: 20111207 |