CN103922899B - A kind of method extracting Honokiol and magnolol in bark of official magnolia crude extract - Google Patents
A kind of method extracting Honokiol and magnolol in bark of official magnolia crude extract Download PDFInfo
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- CN103922899B CN103922899B CN201410161323.9A CN201410161323A CN103922899B CN 103922899 B CN103922899 B CN 103922899B CN 201410161323 A CN201410161323 A CN 201410161323A CN 103922899 B CN103922899 B CN 103922899B
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/70—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment
- C07C37/72—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment by liquid-liquid treatment
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/685—Processes comprising at least two steps in series
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/70—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment
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Abstract
The invention discloses a kind of method extracting Honokiol and magnolol in bark of official magnolia crude extract.Carry out being separated in the method for Honokiol and magnolol to bark of official magnolia crude extract at present, some costs are too high, and turnout is little, and scale operation not easily realizes.The present invention utilizes the Magnolol and Honokiol contained in bark of official magnolia crude extract can reach with under certain density alkaline condition the feature be separated completely in low-pole solution, first weakly alkaline solvent is used to extract magnolol from mixing solutions, Honokiol retains in the solution, Honokiol is extracted again with strong base solution, some oil impurities are retained in organic solvent layer, then respectively acid adjustment, separates out precipitation, and in the coarse-grain of at this moment gained, Magnolol and Honokiol content is improved largely.Separation of the present invention, purifying process are simple, are applicable to industrialized production, and obtained magnolol, Honokiol can be used for exploitation single component new drug.
Description
Technical field
The present invention relates to the method preparing natural chemicals in plant extract medicinal extract, specifically a kind of method extracting single component Honokiol and magnolol from bark of official magnolia crude extract.
Background technology
Magnolol (Magnolol) and Honokiol (Honokiol) are the main chemical compositions of Cortex Magnoliae Officinalis.Pharmacological testing shows, magnolol has special, lasting myorelaxant effects and stronger anti-microbial effect, can anticoagulant, is mainly clinically used as antibacterial, antifungal drug.In anti-microbial effect, magnolol has significant anti-microbial activity to gram-positive bacteria, acid resistance bacterium, filamentous fungus, has more significant anti-microbial effect to streptococcus mutans, the strongest to staphylococcic restraining effect.Mainly clinically be used as to eliminate the medicines such as full vexed, the calm nervus centralis of chest abdomen, sportsmen are of flaccid muscles, antimycotic, antiulcer agent.Honokiol also exists huge potentiality in antineoplaston, there is bibliographical information, the antitumor action of Honokiol has the feature of Mutiple Targets, too many levels, manifold effect, and toxic side effect is low, not only there is obvious cytotoxicity to common tumour cell, have the tumour cell of drug resistance (as multiple myeloma cells) also to have certain result for the treatment of for some.
Chinese Patent Application No. 201310217604.7 discloses the purposes of magnolol as CYP2E1 enzyme inhibitors; result of study shows that the liver CYP2E1 enzymic activity of magnolol to the type-II diabetes rat that high-sugar-fat-diet nursing-low dosage STZ induces has significant restraining effect; to the rat liver oxidativestress damage that CYP2E1 enzyme high expression level causes, there is obvious provide protection, obviously can reduce blood sugar and the blood lipid level of diabetes rat.These experimental basis and theoretical basis, all point out magnolol as the single component existing very strong science of exploitation and novelty, have again very high development and application values.
At present technique mainly macroreticular resin absorbing method, TLC preparative separation method, high-speed counter-current extraction process, silica gel column chromatography, the high performance liquid chromatography preparation method etc. being separated Honokiol and magnolol are carried out to bark of official magnolia crude extract, high-speed counter-current extraction process, high performance liquid chromatography preparation method apparatus expensive, early investment is very large, cost is too high, and complicated operation, turnout is little, and scale operation not easily realizes; Although silica gel column chromatography, macroreticular resin absorbing method can scale production but the single component content obtained is not high, and workload is large, the cycle is long, and production cost is too high, and product does not have the market competitiveness at all; TLC preparative separation method can only be used for a small amount of preparation in laboratory, can not be used for large-scale commercial production.
Chinese Patent Application No. 201110328031.6 discloses a kind of method preparing high-purity magnolia bark phenol and Honokiol from the bark of official magnolia, be characterized in first extracting magnolia bark total-phenol with ethanolic soln, again magnolia bark total-phenol is carried out silica gel wet method dress column chromatography for separation, carry out wash-out with petroleum ether-ethyl acetate-methyl alcohol, the Determination of Magnolol obtained only has about 90%, and mother liquor needs silica column purification again, cycle is long, efficiency is low, and cost is high, is not suitable for industrialized production.
Summary of the invention
Technical problem to be solved by this invention is the defect overcoming the existence of above-mentioned prior art, provides a kind of method extracting high-purity magnolia bark phenol and Honokiol from bark of official magnolia crude extract, for developing new bark of official magnolia monomer formulation, improves added value.
For this reason, the present invention adopts following technical scheme: a kind of method extracting Honokiol and magnolol in bark of official magnolia crude extract, and its step is as follows:
1) heating for dissolving: bark of official magnolia crude extract dry powder is weighed, add the organic solvent low polarity alkane of 10-20 times amount or low polar ether by weight, reflux dissolves 2-4 hour, the buffered soln of the pH10-11 of 4-6 times of solvent volume is added in the solution obtained, keep solution temperature 60 ~ 80 DEG C, stir, leave standstill after 0.5 ~ 1h, layering;
2) extracting: by step 1) the lower floor buffered soln of gained collects, and takes advantage of the organic solvent on the clean upper strata of thermal separation; By upper organic layer again with the extraction of the buffered soln of the pH10-11 of 4-6 times of solvent volume, totally five times, collect lower floor's buffered soln; The 0.5-1.5% sodium hydroxide solution of upper organic layer with 4-6 times of its volume is extracted 1 ~ 3 time, and takes advantage of thermal separation, collect lower floor's sodium hydroxide solution;
3) acidifying, precipitation: by step 2) the lower floor buffered soln of gained merges, and add hydrochloric acid after cooling, adjust pH is 2.5-3.5, leaves standstill and separates out precipitation, be magnolol coarse-grain; By step 2) the lower floor sodium hydroxide solution of gained merges, and add hydrochloric acid after cooling, adjust pH is 2.5-3.5, leaves standstill and separates out precipitation, be Honokiol coarse-grain;
4) recrystallization, purifying: described recrystallization is after step 3) gained magnolol coarse-grain 10 ~ 20 times of sherwood oils are refluxed dissolving in 60 ~ 80 DEG C, separate out oil reservoir and the dirt of lower floor, take advantage of thermal separation to go out the sherwood oil on upper strata, cold postpone crystallization, is the magnolol of more than 98%; Namely same method, will obtain the Honokiol of more than 98% after the process of step 3) gained Honokiol coarse-grain.
The present invention utilizes the Magnolol and Honokiol contained in bark of official magnolia crude extract can reach with (i.e. weakly alkaline solution) under certain density alkaline condition the feature be separated completely in weak polar solvent (i.e. low polar solvent), first weakly alkaline solution (pH10-11 buffered soln) is used to extract magnolol from mixing solutions, Honokiol retains in the solution, Honokiol is extracted again with strong base solution (0.5-1.5% sodium hydroxide), some oil impurities are retained in organic solvent layer, then acid adjustment respectively, separate out precipitation, in the coarse-grain of at this moment gained, Magnolol and Honokiol content is improved largely (bringing up to more than 90 percent from 30 percent), and control to put in place (pH10-11 due to pH value, special pH10.5), Magnolol and Honokiol is separated very thorough, impurities is some volatile oil mainly, only need a step sherwood oil process can reach more than 98% content, more easily carry out large production operation.
Further, described low polarity alkane is normal hexane or hexanaphthene.
Further, described low polar ether is sherwood oil.
Further, step 2) in, extracting pH value of buffer solution used is 10.5, can ensure the maximum separation of Magnolol and Honokiol.
Further, the compound method of pH10.5 buffered soln is: sodium bicarbonate 2.1g and sodium hydroxide 0.712g, adds water to 1000ml, and sodium bicarbonate, sodium hydroxide are analytical pure, and water is purified water; The compound method of pH10.5 buffered soln also can be: sodium bicarbonate 2.1g and sodium hydroxide 0.9g, and sodium bicarbonate, sodium hydroxide are technical grade, and water is tap water.
Further, the mass percentage concentration extracting sodium hydroxide solution used is 1.0%.
Further, in described bark of official magnolia crude extract dry powder, the content of magnolol is at 35-42%, and in the rear gained coarse-grain of extraction, the content of magnolol is about 95%; The content of Honokiol is at 38-45%, and in the rear gained coarse-grain of extraction, the content of Honokiol is about 93%.
The present invention takes full advantage of Magnolol and Honokiol can reach the feature be separated completely between pH10 ~ 11, first accurate formulation buffered soln makes pH be stabilized in 10.5, reach optimum separating point, ensure that the selectivity of extraction is good, treatment capacity large, make extraction completely, thoroughly; Separation of the present invention, purifying process are simple, are applicable to industrialized production, and obtained magnolol, Honokiol can be used for exploitation single component new drug.
Embodiment
Below in conjunction with embodiment, the present invention is described further, but be not limited to the scope of the present embodiment.
embodiment 1
Get bark of official magnolia crude extract 100g, add hexanaphthene 1000ml, put in 10000ml round-bottomed flask, in water-bath, 85 DEG C of reflux thermosols, react 2 hours in time starting to reflux.Get purified water and be heated to about about 80 DEG C, analytical pure sodium bicarbonate 2.1g and analytical pure sodium hydroxide 0.712g, adds purified water to 1000ml, is mixed with pH10.5 damping fluid.The 5000ml damping fluid be made into by preceding method adds in 10000ml round-bottomed flask, opening stirring makes mixing abundant in 30 minutes, leave standstill 10 minutes rearmounted separating funnel higher slices, divide and take off a layer buffer layer, operate five times with method, get debris and detect without adding 1% sodium hydroxide solution extraction Honokiol after magnolol spot; Lower floor's buffer layer is added the every 1000ml damping fluid of 4MHCL(and adds 10ml4M hydrochloric acid), make pH about 3, leave standstill crystallization after fully stirring, obtain magnolol coarse-grain 41.2g; Lower floor's sodium hydroxide solution is added the every 1000ml sodium hydroxide solution of 4MHCL(and adds 70ml4M hydrochloric acid), make pH about 2 ~ 3, leave standstill crystallization after fully stirring, obtain Honokiol coarse-grain 43.1g; Magnolol coarse-grain 41.2g adds 410ml sherwood oil (60 ~ 90 DEG C) and dissolves in 80 DEG C of water-bath backflows, can see that there are part oil reservoir and dirt in lower floor, take advantage of heat by clean for upper strata sherwood oil impouring crystallizing dish, coldly put crystallization, crystal, with 80 DEG C of dryings, obtains magnolol 38.8g, content 99.03%; Honokiol coarse-grain 43.1g adds 430ml sherwood oil (60 ~ 90 DEG C) and dissolves in 80 DEG C of water-baths backflow, separates out lower floor's oil reservoir, takes advantage of heat by clean for upper strata sherwood oil impouring crystallizing dish, coldly puts crystallization, and crystal, with 65 DEG C of dryings, obtains Honokiol 40.11g, content 99.2%.
embodiment 2
Get bark of official magnolia crude extract 1000g, add hexanaphthene 10000ml, 80 DEG C of reflux 3 hours in 100L reactor; Separately get tap water 100Kg to put in caldron and be heated to about 80 DEG C, by sodium hydroxide 0.9g, sodium bicarbonate 2.1g, adds sodium bicarbonate and sodium hydroxide with tap water to the ratio of 1000ml, stirs and make the damping fluid being fully dissolved into pH10.5.Open reactor stirrer, add 50Kg damping fluid while stirring, then after stirring 15 minutes, leave standstill, layering; With method operation, coextraction five times, gets debris point sample and detects without magnolol spot, get tap water and prepare 1% sodium hydroxide solution, extraction secondary.Lower floor's buffer layer is added the every 1000ml damping fluid of 4MHCL(and adds 10ml4M hydrochloric acid), make pH about 3, leave standstill crystallization after fully stirring, obtain magnolol coarse-grain 408g; Lower floor's sodium hydroxide solution is added the every 1000ml sodium hydroxide solution of 4MHCL(and adds 70ml4M hydrochloric acid), make pH about 2 ~ 3, leave standstill crystallization after fully stirring, obtain Honokiol coarse-grain 425g; Magnolol coarse-grain 408g adds 4000ml sherwood oil (60 ~ 90 DEG C) and dissolves in 80 DEG C of water-bath backflows, can see that there are part oil reservoir and dirt in lower floor, take advantage of heat by clean for upper strata sherwood oil impouring crystallizing dish, coldly put crystallization, crystal, with 80 DEG C of dryings, obtains magnolol 381g, content 99.11%; Honokiol coarse-grain 425g adds 4200ml sherwood oil (60 ~ 90 DEG C) and dissolves in 80 DEG C of water-baths backflow, separates out lower floor's oil reservoir, takes advantage of heat by clean for upper strata sherwood oil impouring crystallizing dish, coldly puts crystallization, and crystal, with 65 DEG C of dryings, obtains Honokiol 417.5g, content 98.6%.
embodiment 3
Get bark of official magnolia crude extract 10Kg, add hexanaphthene 80Kg, in multi-function extractor, reflux 4 hours, makes abundant thermosol; Separately getting 500Kg tap water puts in caldron, is steam heated to about 80 DEG C, and by sodium hydroxide 0.9g, sodium bicarbonate 2.1g, adds sodium bicarbonate and sodium hydroxide with tap water to the ratio of 1000ml, stirs and makes the damping fluid being fully dissolved into pH10.5.Open multi-function extractor stirrer, add 500Kg damping fluid while stirring, then after stirring 15 minutes, leave standstill, layering; With method operation, coextraction five times, gets debris point sample and detects without magnolol spot, get tap water and prepare 1% sodium hydroxide solution, extraction secondary.Lower floor's buffer layer is added the every 1000ml damping fluid of 4MHCL(and adds 10ml4M hydrochloric acid), make pH about 3, leave standstill crystallization after fully stirring, obtain magnolol coarse-grain 4.14Kg; Lower floor's sodium hydroxide solution is added the every 1000ml sodium hydroxide solution of 4MHCL(and adds 70ml4M hydrochloric acid), make pH about 2 ~ 3, leave standstill crystallization after fully stirring, obtain Honokiol coarse-grain 4.53Kg; Magnolol coarse-grain 4.14Kg adds 41000ml sherwood oil (60 ~ 90 DEG C) and dissolves in 80 DEG C of water-bath backflows, can see that there are part oil reservoir and dirt in lower floor, take advantage of heat by clean for upper strata sherwood oil impouring crystallizing dish, coldly put crystallization, crystal, with 80 DEG C of dryings, obtains magnolol 3.98Kg, content 99.05%; Honokiol coarse-grain 4.53Kg adds 45000ml sherwood oil (60 ~ 90 DEG C) and dissolves in 80 DEG C of water-bath backflows, separates out lower floor's oil reservoir, takes advantage of heat by clean for upper strata sherwood oil impouring crystallizing dish, coldly put crystallization, crystal, with 65 DEG C of dryings, obtains Honokiol 4.32Kg, content 99.02%.
In above-described embodiment, the high performance liquid phase detection method of Magnolol and Honokiol is: high performance liquid chromatograph Agilent 1260; Moving phase: Methanol-water (78:22); Chromatographic column: C
18post (4.6 × 250mm); Determined wavelength selects 294nm; Flow velocity is: 1.0ml/min, ambient operation.
TLC method in process control: silica gel g thin-layer plate 10 × 20cm; Developping agent: benzene-methyl alcohol (27:1); Developer is: 1% vanillin-sulfuric acid solution, is heated to spot development clear after spray at 100 DEG C.
Claims (3)
1. in bark of official magnolia crude extract, extract a method for Honokiol and magnolol, its step is as follows:
1) heating for dissolving: bark of official magnolia crude extract dry powder is weighed, add the organic solvent low polarity alkane of 10-20 times amount or low polar ether by weight, reflux dissolves 2-4 hour, the weakly alkaline solution of the pH10.5 of 4-6 times of solvent volume is added in the solution obtained, keep solution temperature 60 ~ 80 DEG C, stir, leave standstill after 0.5 ~ 1h, layering;
2) extracting: by step 1) the lower floor weakly alkaline solution of gained collects, and is separated the organic solvent on clean upper strata while hot; By upper organic layer again with the extraction of the weakly alkaline solution of the pH10.5 of 4-6 times of solvent volume, totally five times, collect lower floor's weakly alkaline solution; The 0.5-1.5% sodium hydroxide solution of upper organic layer with 4-6 times of its volume is extracted 1 ~ 3 time, and is separated while hot, collect lower floor's sodium hydroxide solution;
3) acidifying, precipitation: by step 2) the lower floor weakly alkaline solution of gained merges, and add hydrochloric acid after cooling, adjust pH is 2.5-3.5, leaves standstill and separates out precipitation, be magnolol coarse-grain; By step 2) the lower floor sodium hydroxide solution of gained merges, and add hydrochloric acid after cooling, adjust pH is 2.5-3.5, leaves standstill and separates out precipitation, be Honokiol coarse-grain;
4) recrystallization, purifying: described recrystallization is after step 3) gained magnolol coarse-grain 10 ~ 20 times of sherwood oils are refluxed dissolving in 60 ~ 80 DEG C, separate out oil reservoir and the dirt of lower floor, isolate the sherwood oil on upper strata while hot, cold postpone crystallization, is the magnolol of more than 98%; Namely same method, will obtain the Honokiol of more than 98% after the process of step 3) gained Honokiol coarse-grain;
Described low polarity alkane is hexanaphthene or normal hexane, and described low polar ether is sherwood oil;
The compound method of pH10.5 weakly alkaline solution is: sodium bicarbonate 2.1g and sodium hydroxide 0.712g, adds water to 1000ml, and sodium bicarbonate, sodium hydroxide are analytical pure, and water is purified water; Or sodium bicarbonate 2.1g and sodium hydroxide 0.9g, sodium bicarbonate, sodium hydroxide are technical grade, and water is tap water.
2. the method extracting Honokiol and magnolol in bark of official magnolia crude extract according to claim 1, is characterized in that, step 2) in extraction sodium hydroxide solution used mass percentage concentration be 1.0%.
3. the method extracting Honokiol and magnolol in bark of official magnolia crude extract according to claim 1, is characterized in that, in described bark of official magnolia crude extract dry powder, the content of magnolol is at 35-42%, and the content of Honokiol is at 38-45%.
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Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN104230673A (en) * | 2014-09-30 | 2014-12-24 | 桂林三宝药业有限公司 | Method for extracting magnolol from officinal magnolia barks |
| CN104341272A (en) * | 2014-09-30 | 2015-02-11 | 桂林三宝药业有限公司 | Method for preparing honokiol from Mangnolia officinalis |
| 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 | Magnolol and method for extracting and separating honokiol |
| CN109485551B (en) * | 2018-11-27 | 2021-07-30 | 中南民族大学 | Method for separating and preparing honokiol from magnolia officinalis |
| CN109336742B (en) * | 2018-11-27 | 2021-07-30 | 中南民族大学 | Method for separating and purifying magnolol from magnolia officinalis |
| CN109627147A (en) * | 2018-11-27 | 2019-04-16 | 中南民族大学 | A kind of honokiol crystal and preparation method thereof |
| CN110403984A (en) * | 2019-08-26 | 2019-11-05 | 王鹏 | A kind of acne-removing composition and preparation method thereof |
| CN112106786B (en) * | 2020-09-27 | 2022-05-17 | 山东大学 | Method for extracting pesticide components from biomass raw material based on pasteurization |
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| CN101857531A (en) * | 2010-06-14 | 2010-10-13 | 江西海富生物工程有限公司 | Method for extracting magnolol and honokiol from magnolia bark |
| CN101857530A (en) * | 2010-05-26 | 2010-10-13 | 广州和博生物科技有限公司 | Separation method for magnolol and honokiol |
| CN102408314A (en) * | 2011-12-09 | 2012-04-11 | 广西大学 | Method for preparing high-purity magnolol and magnolol |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN101857530A (en) * | 2010-05-26 | 2010-10-13 | 广州和博生物科技有限公司 | Separation method for magnolol and honokiol |
| CN101857531A (en) * | 2010-06-14 | 2010-10-13 | 江西海富生物工程有限公司 | Method for extracting magnolol and honokiol from magnolia bark |
| CN102408314A (en) * | 2011-12-09 | 2012-04-11 | 广西大学 | Method for preparing high-purity magnolol and magnolol |
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