CN104163755B - A kind of method preparing magnolol and Honokiol from Leaf of Magnolia officinalis - Google Patents
A kind of method preparing magnolol and Honokiol from Leaf of Magnolia officinalis Download PDFInfo
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Abstract
The present invention relates to a kind of method preparing magnolol and Honokiol from Leaf of Magnolia officinalis, belong to modern Chinese traditional medicine field.A kind of method preparing magnolol and Honokiol from Leaf of Magnolia officinalis, the methods such as application organic solvent extraction, the preparation of small-bore resin isolation, organic solvent crystallization prepare high-purity magnolia bark phenol and Honokiol monomer component from Leaf of Magnolia officinalis, have compared with processing method with existing, simply, slightly extraction solvent cost is low, old of column chromatography is low, filler separation accuracy height can be recycled to have technique, solvent system cost is low, environmental pollution is relatively light, magnolol and Honokiol purity advantages of higher, is applicable to industrial preparation.
Description
Technical field
The present invention relates to a kind of method preparing magnolol (Magnolol) and Honokiol (Honokiol) from Leaf of Magnolia officinalis, belong to modern Chinese traditional medicine field.
Background technology
Magnolol and Honokiol are isomers, and the two is the Antibacterial Constituents of the conventional Chinese medicine bark of official magnolia, are also the leading indicator compositions of magnolia medicament quality control simultaneously.Both bibliographical informations, except anti-microbial effect, also have anti-inflammatory, anxiety, antidepressant, antitumor, anti-ageing and myocardium protecting action; In addition, the of flaccid muscles and Central nervous depressant of obvious, lasting in addition central; Have pharmacodynamic study to confirm in the recent period, magnolol and Honokiol also demonstrate hypoglycemic activity.
The bark of official magnolia is conventional Chinese medicine, derive from the dry dry hide of Magnoliaceae magnolia bark of official magnolia Magnolia officinalis Rehd et Wils. and Magnolia bilola Magnolia officinalis Rehd.et Wils.var.biloba Rehd.et Wils., branch skin and Gen Pi, main product in Sichuan, Hubei, Zhejiang, the ground such as Fujian and Anhui, have remove dampness by means of aromatics, promoting the circulation of qi disappears long-pending, eliminating dampness except effect that is full, lowering the adverse QI to relieve asthma, the illness such as cure mainly stagnation of QI due to dyspepsia, abdominal distention constipation, retention of dampness in middle-JIAO, gastral cavity ruffian is vomited and diarrhoea, phlegm stops up the circulation of vital energy in the wrong direction, fullness sensation in chest is breathed with cough.The bark of official magnolia is had to be used as medicine in many conventional prescriptions and Chinese patent medicine preparation.
Along with the expansion of magnolia medicament range of application, its demand, in continuous increase, is meet the demand constantly increased it, at present in Sichuan, Hubei, Zhejiang, the main producing region such as Fujian set up magnolia medicament production base, greatly develops bark of official magnolia plantation.According to the preliminary statistics, the whole nation plantation bark of official magnolia and Magnolia bilola area are no less than 700,000 mu, and cultivation bark of official magnolia woods mostly is bark of official magnolia pure forest, the strain of every mu of cultivation bark of official magnolia about 200 ~ 300, set every annual with every strain and produce bark of official magnolia cured leaf 1.5 ~ 2.5kg calculating, the standing stock of national Leaf of Magnolia officinalis can reach more than 300,000 tons every year.The bark of official magnolia is deciduous tree, its leaf long 25 ~ 50cm, wide 15 ~ 25cm, and November withers and falls naturally, and spring in the coming year sends out young leaves again, and therefore, Leaf of Magnolia officinalis obtain manner is easy, aboundresources and can regenerating every year.At present, domestic a large amount of Leaf of Magnolia officinalis does not add utilization, lets alone to wither and fall rotten, if develop as new medicinal material, not only be conducive to the comprehensive utilization of bark of official magnolia resource, and larger economic benefit and social benefit can be produced, conceding the land to forestry and medicinal herb grower are increased income and also plays certain supporting function.
Modern Analytical Chemistry research finds, also containing the lignan component that magnolia obovata is identical in Leaf of Magnolia officinalis, can be used as the material plant position of magnolol and Honokiol.In existing patent report Leaf of Magnolia officinalis, magnolol and Honokiol extracting method have organic solvent extraction, adopt temperature control curve to control heat-up rate and constant temperature extraction etc.These extracting method extraction target compound impurity too much, magnolol and Honokiol purity lower, be not suitable for industrialization scale operation.
Chinese patent application CN 102304027 A discloses a kind of method extracting magnolol from bark of official magnolia leaf, and the steps include: that 1. Leaf of Magnolia officinalis powder methyl alcohol soak 24h, suction filtration, repeat leaching three times, filtrate is concentrated into medicinal extract; 2. add saturated clarification limewater in medicinal extract, stir 1h, centrifugal, in triplicate; 3. supernatant liquor is acidified to pH=2-3, stirs 30min, centrifugal, solid substance silica gel mix, then is heated to micro-boiling with sherwood oil, insulation 10min, heat filter, solution anhydrous Na
2sO
4dry; 4. dry petroleum ether solution is concentrated, crystallisation by cooling, obtain magnolol product.Need in the method to use concentrated acid that supernatant liquor pH value is adjusted to 2-3, and be heated to micro-boiling with sherwood oil.Sherwood oil is inflammable and explosive, and its steam and air can form explosive mixture, and chance naked light, high heat energy cause combustion explosion.These factors add the risk of operation, have both been unfavorable for protecting laborer, are also unfavorable for industrialized implementation.Sherwood oil cost is higher.
Summary of the invention
The object of the invention is the deficiency for existing industrialization separating magnolol and Honokiol technology, provide that a kind of processing unit is simple, with short production cycle, scale of investment is little, the preparation method of operational safety, environmental pollution are relatively light, preparation cost is low, yield is higher high-purity magnolia bark phenol and Honokiol.
The present invention realizes the object of the invention by the following method:
From Leaf of Magnolia officinalis, prepare a method for magnolol and Honokiol, step is as follows:
(1) get dry Leaf of Magnolia officinalis to pulverize;
(2) Leaf of Magnolia officinalis powder is 60-95% alkaline methanol or ethanolic soln refluxing extraction 2-3 time with the concentration of volume percent that the pH value of 4 ~ 6 times amount is 9-10, Extracting temperature is 60 ~ 70 DEG C, each refluxing extraction 0.5-3h, united extraction liquid, being adjusted to pH value with acid is 6-7, and recycling design obtains medicinal extract;
(3) medicinal extract is with after 9 ~ 10 times amount water dissolution, with dichloromethane extraction 2-3 time of 1 ~ 2 times amount, or uses alumina adsorption enrichment, collects effluent liquid, evaporate to dryness, for subsequent use;
(4) get small-bore separation resin to add and press-fit post, be the methyl alcohol of 35-50% or ethanol or aqueous acetone solution balance pillar with concentration of volume percent, then sample solution is slowly dripped loading, after the complete standing 1-1.5h of loading successively with the concentration of volume percent of 1 ~ 2 times amount be 50%, 55%, 60%, 65%, 70% methyl alcohol, ethanol or aqueous acetone solution pressurization wash-out, collect magnolol and Honokiol section elutriant, concentration and recovery solvent, obtains magnolol and Honokiol blending ingredients;
(5) magnolol and Honokiol blending ingredients is got, with anhydrous methanol or ethanol or acetone solution, with the silica gel mixed sample of 4 ~ 6 times amount, be filler with silica gel, sherwood oil-the acetone being 6:1-8:1 with the volume ratio of 18 ~ 20 times amount is for eluent, and chromatography, detects, with the acetone methyl alcohol mixed liquor crystallization 2 times of 2 ~ 4 times amount, obtain magnolol and Honokiol monomer.
Alkaline methanol described in step (2) or ethanolic soln adopt sodium bicarbonate, sodium hydroxide or ammoniacal liquor to regulate its pH value; Being adjusted to neutral acid with acid is hydrochloric acid.
Step (4) small aperture separation resin is Chroma-R204.The fine that the present invention adopts is separated small-bore polymeric adsorbent, and low price, even aperture distribution, separation accuracy is higher, and can not make the dead absorption of paired samples, and can reuse, eluting solvent cost is low, applied sample amount is large.
Acetone methanol mixed solution described in step (5) is that acetone and methyl alcohol 15:1 mixing are by volume obtained.
A kind of Leaf of Magnolia officinalis extract, adopts following methods to prepare:
(1) get dry Leaf of Magnolia officinalis to pulverize;
(2) Leaf of Magnolia officinalis powder is 60-95% alkaline methanol or ethanolic soln refluxing extraction 2-3 time with the concentration of volume percent that the pH value of 4 ~ 6 times amount is 9-10, Extracting temperature is 60 ~ 70 DEG C, each refluxing extraction 0.5-3h, united extraction liquid, being adjusted to pH value with acid is 6-7, and recycling design obtains medicinal extract;
(3) medicinal extract is with after 9 ~ 10 times amount water dissolution, with dichloromethane extraction 2-3 time of 1 ~ 2 times amount, or uses alumina adsorption enrichment, collects effluent liquid, evaporate to dryness, for subsequent use;
(4) get small-bore separation resin to add and press-fit post, be the methyl alcohol of 35-50% or ethanol or aqueous acetone solution balance pillar with concentration of volume percent, then sample solution is slowly dripped loading, after the complete standing 1-1.5h of loading successively with the concentration of volume percent of 1 ~ 2 times amount be 50%, 55%, 60%, 65%, 70% methyl alcohol, ethanol or aqueous acetone solution pressurization wash-out, collect magnolol and Honokiol section elutriant, concentration and recovery solvent, obtains magnolol and Honokiol blending ingredients;
(5) magnolol and Honokiol blending ingredients is got, with anhydrous methanol or ethanol or acetone solution, with the silica gel mixed sample of 4 ~ 6 times amount, be filler with silica gel, sherwood oil-the acetone being 6:1-8:1 with the volume ratio of 18 ~ 20 times amount is for eluent, and chromatography, detects, with the acetone methyl alcohol mixed liquor crystallization 2 times of 2 ~ 4 times amount, obtain magnolol and Honokiol monomer.
Alkaline methanol described in step (2) or ethanolic soln adopt sodium bicarbonate, sodium hydroxide or ammoniacal liquor to regulate its pH value; Being adjusted to neutral acid with acid is hydrochloric acid.
Step (4) small aperture separation resin is Chroma-R204.
Acetone methanol mixed solution described in step (5) is that acetone and methyl alcohol 15:1 mixing are by volume obtained.
The content >98% of magnolol and Honokiol in described extract.
Described Leaf of Magnolia officinalis extract is for the preparation of the purposes of antimicrobial drug, antiphlogiston, anxiolytic, thymoleptic, antitumour drug, Kangshuaining mixture medicine, myocardial preservation medicine or hypoglycemic agents.
The advantage of the inventive method is as follows: the invention provides with bark of official magnolia dis-medicinal part for raw material, the method for suitability for industrialized production living features composition magnolol and Honokiol.Magnolol and Honokiol polarity less, and in slightly acidic, therefore with the alkaline alcohol liquid of high density extract can make both solubility rate higher.Small-bore separation resin, employing different concns acetone, ethanol or methyl alcohol etc. on extract are obtained magnolol and the single spot of Honokiol on TLC for eluent all can better be separated.Can effectively separate the impurity such as chlorophyll and longer chain fatty acid.Fine is separated the dead absorption that small-bore polymeric adsorbent can not make paired samples, and it can reuse, and has the advantages such as eluting solvent cost is low, applied sample amount is large.The small-bore semi-gelled type polymeric adsorbent even aperture distribution of more domestic producer exploitation at present, 40-100um price is lower, per kilogram about 300 yuan, separation accuracy is higher, and the separation and Extraction of some plants has the MCI GEL resin series separation function of expensive foreign.
The inventive method processing unit is simple, with short production cycle, scale of investment is little, environmental pollution is relatively light, preparation cost is low, magnolol and Honokiol purity high, easy to operate and safe, be suitable for suitability for industrialized production.
Below in conjunction with the drawings and specific embodiments, the present invention will be further described, not limitation of the present invention, and all equivalent replacements in this area done according to the disclosure of invention, all belong to protection scope of the present invention.
Accompanying drawing explanation
Fig. 1 is the Honokiol HPLC collection of illustrative plates of embodiment 1
Fig. 2 is the Honokiol HPLC collection of illustrative plates of embodiment 2
Fig. 3 is the magnolol HPLC collection of illustrative plates of embodiment 1
Fig. 4 is the magnolol HPLC collection of illustrative plates of embodiment 2
Embodiment
Be described in further detail the inventive method below by embodiment, but protection scope of the present invention is not limited to described content, in embodiment if no special instructions, use reagent is conventional commercial reagent, or reagent obtained according to a conventional method.
Embodiment 1:
1. getting Leaf of Magnolia officinalis 96g, to be crushed to granularity be 40 orders;
2. the Leaf of Magnolia officinalis powder 95% ethanolic soln refluxing extraction three times of ammoniacal liquor adjust ph 10, Extracting temperature 60 DEG C, wherein 500ml solution return extracts filtration after 2 hours for the first time, filter residue 500ml solution second time refluxing extraction was filtered after 1 hour, filter residue 500ml solution third time refluxing extraction is filtered for 0.5 hour, merges No. three extracting solutions; With salt acid for adjusting pH value 6, recycling design, obtain crude extract (28.8g);
3. with 300ml water dissolution crude extract, with dichloromethane extraction 3 times, each 300ml, combined dichloromethane liquid, evaporate to dryness, obtains medicinal extract (14.2g);
4. get 500g small-bore separation resin Chroma-R204 to add and press-fit post, with the aqueous acetone solution balance pillar that concentration of volume percent is 50%, then sample solution is slowly dripped loading, after the complete standing 1h of loading successively with 500ml concentration of volume percent be 50%, 55%, 60%, 65%, 70% aqueous acetone solution pressurization wash-out (7bar), TLC differentiates to collect magnolol and Honokiol section elutriant, reclaim acetone water, obtain component A (8.3g);
5. get component A, use 100ml acetone solution, with 50g silica gel mixed sample, be filler with silica gel, with 800ml sherwood oil---acetone (8:1) wash-out, concentrated, obtain B component (2.2g) and component C (1.8g), distinguish crystallization 2 times with 7ml acetone methyl alcohol mixed liquor (the 15:1 mixing by volume of acetone and methyl alcohol) and 6ml acetone methyl alcohol mixed liquor (the 15:1 mixing by volume of acetone and methyl alcohol), separable purifying obtains compound 1 (0.24g) and compound 2 (0.13g).HPLC detection level >98% (see Fig. 1 and Fig. 3)
Above gained compound monomer 1 and compound 2, measure through mass spectrum, proton nmr spectra, carbon spectrum, be accredited as successively respectively: magnolol (Magnolol), Honokiol (Honokiol).
Embodiment 2:
1. getting Leaf of Magnolia officinalis 95g, to be crushed to granularity be 40 orders;
2. the Leaf of Magnolia officinalis powder 95% ethanolic soln refluxing extraction three times of ammoniacal liquor adjust ph 9, Extracting temperature 60 DEG C, wherein 500ml solution return extracts filtration after 2 hours for the first time, filter residue 500ml solution second time refluxing extraction was filtered after 1 hour, filter residue 500ml solution third time refluxing extraction is filtered for 0.5 hour, merges No. three extracting solutions; With salt acid for adjusting pH value 6, recycling design, obtain crude extract (28.2g);
3. with 300ml water dissolution crude extract, filter, residue 100ml acetone solution, adds 400ml water and becomes suspension, and with the enrichment of 100g alumina adsorption, collect effluent liquid, evaporate to dryness, obtains medicinal extract (13.3g);
4. get 500g small-bore separation resin Chroma-R204 to add and press-fit post, with the aqueous acetone solution balance pillar that concentration of volume percent is 50%, then sample solution is slowly dripped loading, after the complete standing 1h of loading successively with 500ml concentration of volume percent be 50%, 55%, 60%, 65%, 70% aqueous acetone solution pressurization wash-out (7bar), TLC differentiates to collect magnolol and Honokiol section elutriant, reclaim acetone water, obtain component A (9.2g);
5. get component A, use 100ml acetone solution, with 50g silica gel mixed sample, be filler with silica gel, with 900ml sherwood oil---acetone (8:1) wash-out, concentrated, obtain B component (2.4g) and component C (1.6g), distinguish crystallization 2 times with 7.5ml acetone methyl alcohol mixed liquor (the 15:1 mixing by volume of acetone and methyl alcohol) and 5ml acetone methyl alcohol mixed liquor (the 15:1 mixing by volume of acetone and methyl alcohol), separable purifying obtains compound 1 (0.73g) and compound 2 (0.49g).HPLC detection level >98% (see Fig. 2 and Fig. 4).
Above gained compound monomer 1 and compound 2, measure through mass spectrum, proton nmr spectra, carbon spectrum, be accredited as successively respectively: magnolol (Magnolol), Honokiol (Honokiol).
Embodiment 3:
1. getting Leaf of Magnolia officinalis 98g, to be crushed to granularity be 40 orders;
2. the Leaf of Magnolia officinalis powder 60% methanol solution refluxing extraction 2 times of ammoniacal liquor adjust ph 9, Extracting temperature 70 DEG C, wherein 500ml solution return extracts filtration after 3 hours for the first time, and filter residue 500ml solution second time refluxing extraction was filtered after 2 hours, merged extracted twice liquid; With salt acid for adjusting pH value 7, recycling design, obtain crude extract (29.4g);
3. with 300ml water dissolution crude extract, with dichloromethane extraction 2 times, each 300ml, combined dichloromethane liquid, evaporate to dryness, obtains medicinal extract (15.2g);
4. get 500g small-bore separation resin Chroma-R204 to add and press-fit post, with the methanol aqueous solution balance pillar that concentration of volume percent is 35%, then sample solution is slowly dripped loading, after the complete standing 1.5h of loading successively with 500ml concentration of volume percent be 50%, 55%, 60%, 65%, 70% methanol aqueous solution pressurization wash-out (7bar), TLC differentiates to collect magnolol and Honokiol section elutriant, reclaim methanol-water, obtain component A (7.8g);
5. get component A, use 100ml dissolve with methanol, with 50g silica gel mixed sample, be filler with silica gel, with 800ml sherwood oil---acetone (6:1) wash-out, concentrated, obtain B component (3.3g) and component C (1.9g), distinguish crystallization 2 times with 10ml acetone methyl alcohol mixed liquor (the 15:1 mixing by volume of acetone and methyl alcohol) and 6ml acetone methyl alcohol mixed liquor (the 15:1 mixing by volume of acetone and methyl alcohol), separable purifying obtains compound 1 (0.22g) and compound 2 (0.12g).HPLC detection level >98%.
Above gained compound monomer 1 and compound 2, measure through mass spectrum, proton nmr spectra, carbon spectrum, be accredited as successively respectively: magnolol (Magnolol), Honokiol (Honokiol).
Embodiment 4:
1. getting Leaf of Magnolia officinalis 97g, to be crushed to granularity be 40 orders;
2. the Leaf of Magnolia officinalis powder 70% ethanolic soln refluxing extraction three times of ammoniacal liquor adjust ph 9, Extracting temperature 65 DEG C, wherein 500ml solution return extracts filtration after 3 hours for the first time, filter residue 500ml solution second time refluxing extraction was filtered after 2 hours, filter residue 500ml solution third time refluxing extraction is filtered for 0.5 hour, merges No. three extracting solutions; With salt acid for adjusting pH value 7, recycling design, obtain crude extract (28.7g);
3. with 300ml water dissolution crude extract, filter, residue 100ml acetone solution, adds 400ml water and becomes suspension, and with the enrichment of 100g alumina adsorption, collect effluent liquid, evaporate to dryness, obtains medicinal extract (13.2g);
4. get 500g small-bore separation resin Chroma-R204 to add and press-fit post, with the aqueous ethanolic solution balance pillar that concentration of volume percent is 40%, then sample solution is slowly dripped loading, after the complete standing 1.5h of loading successively with 500ml concentration of volume percent be 50%, 55%, 60%, 65%, 70% aqueous acetone solution pressurization wash-out (7bar), TLC differentiates to collect magnolol and Honokiol section elutriant, reclaim ethanol water, obtain component A (6.6g);
5. get component A, use 100ml dissolve with ethanol, with 50g silica gel mixed sample, be filler with silica gel, with 1000ml sherwood oil---acetone (7:1) wash-out, concentrated, obtain B component (2.8g) and component C (1.4g), distinguish crystallization 2 times with 9ml acetone methyl alcohol mixed liquor (the 15:1 mixing by volume of acetone and methyl alcohol) and 4.5ml acetone methyl alcohol mixed liquor (the 15:1 mixing by volume of acetone and methyl alcohol), separable purifying obtains compound 1 (0.63g) and compound 2 (0.21g).HPLC detection level >98%.
Above gained compound monomer 1 and compound 2, measure through mass spectrum, proton nmr spectra, carbon spectrum, be accredited as successively respectively: magnolol (Magnolol), Honokiol (Honokiol).
Claims (3)
1. from Leaf of Magnolia officinalis, prepare a method for magnolol and Honokiol, it is characterized in that step is as follows:
(1) get dry Leaf of Magnolia officinalis to pulverize;
(2) Leaf of Magnolia officinalis powder is 60-95% alkaline methanol or ethanolic soln refluxing extraction 2-3 time with the concentration of volume percent that the pH value of 4 ~ 6 times amount is 9-10, Extracting temperature is 60 ~ 70 DEG C, each refluxing extraction 0.5-3h, united extraction liquid, being adjusted to pH value with acid is 6-7, and recycling design obtains medicinal extract;
(3) medicinal extract is with after 9 ~ 10 times amount water dissolution, with dichloromethane extraction 2-3 time of 1 ~ 2 times amount, or uses alumina adsorption enrichment, collects effluent liquid, evaporate to dryness, for subsequent use;
(4) get small-bore separation resin Chroma-R204 to add and press-fit post, be the methyl alcohol of 35-50% or ethanol or aqueous acetone solution balance pillar with concentration of volume percent, then sample solution is slowly dripped loading, after the complete standing 1-1.5h of loading successively with the concentration of volume percent of 1 ~ 2 times amount be 50%, 55%, 60%, 65%, 70% methyl alcohol, ethanol or aqueous acetone solution pressurization wash-out, collect magnolol and Honokiol section elutriant, concentration and recovery solvent, obtains magnolol and Honokiol blending ingredients;
(5) magnolol and Honokiol blending ingredients is got, with anhydrous methanol or ethanol or acetone solution, with the silica gel mixed sample of 4 ~ 6 times amount, be filler with silica gel, sherwood oil-the acetone being 6:1-8:1 with the volume ratio of 18 ~ 20 times amount is for eluent, and chromatography, detects, with the acetone methyl alcohol mixed liquor crystallization 2 times of 2 ~ 4 times amount, obtain magnolol and Honokiol monomer.
2. from Leaf of Magnolia officinalis, extract the method for magnolol and Honokiol according to claim 1, it is characterized in that: the alkaline methanol described in step (2) or ethanolic soln adopt sodium bicarbonate, sodium hydroxide or ammoniacal liquor to regulate its pH value; With acid, to be adjusted to pH value be the acid of 6-7 is hydrochloric acid.
3. from Leaf of Magnolia officinalis, extract the method for magnolol and Honokiol according to claim 1, it is characterized in that: the acetone methanol mixed solution described in step (5) is that acetone and methyl alcohol 15:1 mixing are by volume obtained.
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| CN108143741B (en) * | 2018-01-04 | 2020-09-18 | 中国科学院昆明植物研究所 | Application of magnolol glucoside in preparation of medicine for treating central nervous system diseases |
| CN109627147A (en) * | 2018-11-27 | 2019-04-16 | 中南民族大学 | A kind of honokiol crystal and preparation method thereof |
| CN111773367A (en) * | 2020-08-12 | 2020-10-16 | 安徽氧趣生物科技有限公司 | Compound preparation for treating animal skin diseases and preparation method thereof |
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| CN101735021B (en) * | 2008-11-26 | 2013-03-06 | 湖南农业大学 | Method for separating and purifying magnolol and honokiol by HP-20 macroporous resin |
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