CN109485551B - Method for separating and preparing honokiol from magnolia officinalis - Google Patents
Method for separating and preparing honokiol from magnolia officinalis Download PDFInfo
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- CN109485551B CN109485551B CN201811432276.1A CN201811432276A CN109485551B CN 109485551 B CN109485551 B CN 109485551B CN 201811432276 A CN201811432276 A CN 201811432276A CN 109485551 B CN109485551 B CN 109485551B
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- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
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- 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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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- 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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- C07—ORGANIC CHEMISTRY
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- 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
- C07C37/82—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment by solid-liquid treatment; by chemisorption
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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
- C07C37/84—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment by crystallisation
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Abstract
The invention provides a method for separating and preparing honokiol from mangnolia officinalis, and relates to the technical field of preparation of the honokiol. The method comprises extracting cortex Magnolia officinalis powder with petroleum ether under reflux, extracting with alkali-soluble petroleum ether or ethyl acetate, decolorizing, removing impurities, adjusting pH of decolorized aqueous solution with petroleum ether, and dissolving extracted honokiol with cyclohexane and crystallizing at low temperature. The preparation method does not use toxic chemical reagents, has good environmental compatibility, easy recovery of solvents, cyclic utilization, less energy consumption, low production cost and simple process flow, and is suitable for the requirement of continuous large-scale production. The prepared honokiol has high purity and high yield.
Description
Technical Field
The invention relates to the technical field of honokiol preparation, and particularly relates to a method for separating and preparing honokiol from magnolia officinalis.
Background
The magnolia officinalis is a traditional and commonly used traditional Chinese medicine in China, and magnolol and honokiol are two main effective components in the traditional Chinese medicine magnolia officinalis, and have wide pharmacological effects of resisting bacteria, inflammation, tumors, muscle relaxation, reducing cholesterol, resisting aging and the like.
The magnolia officinalis contains a large amount of impurities such as fat-soluble pigment, the magnolol and the honokiol are isomers, the physical and chemical properties are very similar, the technology of directly separating and purifying the high-purity honokiol from the extracting solution containing a large amount of impurities has certain difficulty, particularly, the process for preparing high-purity honokiol in large quantities in production needs to be further researched and developed, and the prior literature reports that the chromatographic methods for separating and purifying honokiol from magnolia bark, such as silica gel column chromatography, polyamide column chromatography, high-speed counter-current chromatography and the like, the limitations of these methods are that the single sample treatment capacity is small, the organic solvent is difficult to recycle, the process operation is not suitable for the continuous large-scale requirement of production, how to rapidly and efficiently prepare high-purity honokiol from mangnolia officinalis in a large scale is a problem to be solved for the deep research and medicine development of honokiol at present.
Disclosure of Invention
The invention aims to provide a novel method for preparing a large amount of honokiol from magnolia officinalis, and the method has simple process flow and is suitable for continuous large-scale production; and the energy consumption is low, the solvent can be recycled, the production cost is low, and the prepared honokiol has high purity and yield.
The technical problem to be solved by the invention is realized by adopting the following technical scheme.
The invention provides a method for separating and preparing honokiol from magnolia officinalis, which comprises the steps of carrying out hot reflux extraction on magnolia officinalis powder by adopting petroleum ether, extracting, decoloring, removing impurities and crystallizing at low temperature by using petroleum ether or ethyl acetate.
The beneficial effects of the invention include:
1. compared with the traditional ethanol, ethyl acetate and cyclohexane extraction methods, the method for extracting the magnolia total phenol by the petroleum ether through the hot reflux has the advantages that the impurity content of the extract obtained by the alkali extraction and acid precipitation method is greatly reduced, the subsequent purification operation can be simplified, and the preparation of the high-purity honokiol is facilitated. The single efficiency of extracting honokiol by petroleum ether hot reflux is slightly low, can be solved by increasing the proportion of an extraction solvent or the extraction times, and is easy to filter. The petroleum ether is a low-boiling point solvent, is easy to decompress, concentrate and recover, can be recycled, can reduce the production cost and reduce the environmental pollution.
2. The petroleum ether hot reflux extraction extract is dissolved by alkali liquor, most fat-soluble colored impurity components can be removed by using petroleum ether or ethyl acetate for extraction, good conditions are created for subsequent crystallization and purification of the honokiol, and the process steps for separating and purifying the honokiol can be greatly simplified.
3. The process does not use toxic chemical reagents, has good environmental compatibility, is easy to recover petroleum ether and cyclohexane solvents, has low energy consumption, low production cost and simple process flow, and is suitable for the requirement of continuous large-scale production.
4. The process can prepare honokiol crystal with purity of over 98% by one-time crystallization, the appearance is colorless transparent flaky crystal, and the yield of honokiol in magnolia officinalis is over 60%.
Drawings
In order to more clearly illustrate the technical solutions of the embodiments of the present invention, the drawings obtained in the embodiments will be briefly described below, it should be understood that the following drawings only illustrate some embodiments of the present invention and therefore should not be considered as limiting the scope, and for those skilled in the art, other related drawings can be obtained according to the drawings without inventive efforts.
FIG. 1 is an appearance diagram of an alkali-soluble petroleum ether extract of a petroleum ether extract according to an embodiment of the present invention;
FIG. 2 is an appearance diagram of the pH-adjusted petroleum ether extraction of the first extract extraction water phase according to the embodiment of the present invention;
FIG. 3 is an HPLC chromatogram of honokiol and magnolol standard substance in an embodiment of the present invention;
fig. 4 is an HPLC profile of honokiol prepared in the examples of the present invention.
Detailed Description
In order to make the objects, technical solutions and advantages of the embodiments of the present invention clearer, the technical solutions in the embodiments of the present invention will be clearly and completely described below. The examples, in which specific conditions are not specified, were conducted under conventional conditions or conditions recommended by the manufacturer. The reagents or instruments used are not indicated by the manufacturer, and are all conventional products available commercially.
The method for separating and preparing honokiol from magnolia bark in the embodiment of the invention is specifically described below.
The embodiment of the invention provides a method for separating and preparing honokiol from magnolia officinalis, which comprises the following steps: performing hot reflux extraction on the magnolia officinalis medicinal powder by using petroleum ether, dissolving and filtering a petroleum ether extracting solution reduced-pressure concentrated extract by using alkali liquor, extracting, decoloring and purifying a filtrate by using petroleum ether or ethyl acetate, adjusting the pH value of an extracted water phase to be alkalescent, extracting the water phase by using the petroleum ether, heating, dissolving and filtering an extracting solution reduced-pressure concentrated extract by using cyclohexane, crystallizing and separating the filtrate at low temperature, and washing and drying to obtain a finished product of honokiol.
In the embodiment of the invention, the magnolia officinalis powder is extracted by petroleum ether under the condition of 60-80 ℃ for 2-3 times by hot reflux, and each extraction is carried out for 0.5-1.5 h. Wherein the granularity of the officinal magnolia powder is 40-60 meshes, and the mass volume ratio of the officinal magnolia powder to the petroleum ether is 1: 15-20 (W/V).
Filtering the extracting solution, concentrating the filtrate at 50-60 ℃ under reduced pressure to obtain a first extract, and dissolving and filtering the extract by using alkali liquor. Wherein the alkali is one or more of sodium hydroxide, potassium hydroxide and sodium carbonate. The dosage ratio of the first extract to the alkali liquor is 1: 10-20 (W/V), and the concentration of the alkali liquor is 0.5-2M.
And extracting the alkali-soluble filtrate for 1-2 times by using petroleum ether or ethyl acetate, and then extracting the residual water phase. Wherein the volume ratio of the aqueous phase extracted each time to the petroleum ether or the ethyl acetate is 1: 1-2. Petroleum ether or ethyl acetate is used for extraction, so that most fat-soluble colored impurity components can be removed, good conditions can be created for subsequent purification and crystallization of honokiol, and the process steps for separating and purifying honokiol can be greatly simplified.
And (3) adjusting the pH value of the rest water phase to 8-10 by using 1-4M hydrochloric acid, and extracting the water phase for 2-3 times by using petroleum ether. Wherein the volume ratio of the aqueous phase extracted each time to the petroleum ether is 1: 1-2. According to the embodiment of the invention, the pH value of the extracted water phase is adjusted to 8-10 by utilizing the difference of acidity of honokiol and magnolol and the difference of solubility of honokiol and magnolol in a weak alkaline solution, and the operation of extracting with petroleum ether can realize the full separation of honokiol and magnolol.
Decompressing and concentrating the petroleum ether extract at 50-60 ℃ to obtain a second extract, and dissolving the second extract by using cyclohexane at 55-60 ℃, wherein the mass percentage concentration of the neutralized magnolol in the cyclohexane is controlled to be 2.5-4.5%. Filtering while the solution is hot, standing the filtrate at 5-15 ℃ for 10-16 hours to separate out honokiol crystals, and filtering to obtain the honokiol crystals.
And washing the crystal with petroleum ether for 2-3 times, and then drying under reduced pressure and vacuum at the temperature of 60-80 ℃ to obtain a finished product of honokiol.
The preparation method adopts petroleum ether to extract honokiol, so as to reduce the dissolution of impurities. Meanwhile, the petroleum ether is a low-boiling point solvent, is easy to decompress, concentrate, recycle and reuse, and can reduce the production cost and environmental pollution. Toxic chemical reagents are not used in the preparation process, the petroleum ether and cyclohexane solvents are easy to recover, and the environmental compatibility is good; only one-time crystallization is needed, the crystallization operation is simple, the yield is high, the energy consumption is low, the production cost is low, and the process flow is suitable for the requirement of continuous large-scale production.
The method provided by the invention can prepare honokiol with purity of more than 98%, the product purity meets the requirement of pharmaceutical grade, the method can be applied to the field of medicine preparation, and the yield of honokiol in medicinal materials is more than 60%.
The features and properties of the present invention are described in further detail below with reference to examples.
Example 1
Extracting the cortex Magnolia officinalis powder with petroleum ether under reflux at 60 deg.C for 3 times, the first time for 1.5 hr, the second time for 1 hr, and the second time for 0.5 hr, and mixing filtrates. Wherein the granularity of the magnolia officinalis powder is 40 meshes, and the mass volume ratio of the magnolia officinalis powder extracted for three times to the petroleum ether is 1:10, 1:5 and 1:5(W/V) respectively.
Concentrating the extract filtrate under reduced pressure at 50 deg.C to obtain first extract, dissolving the first extract with 0.5M sodium hydroxide solution, filtering, extracting the filtrate with petroleum ether for 2 times, and separating to obtain the residual water phase. Wherein the volume ratio of the petroleum ether to the filtrate in each extraction is 1: 1.
Adjusting pH of the extracted water phase to 8.0 with 2M hydrochloric acid, extracting with petroleum ether for 2 times, and separating to obtain petroleum ether phase. Wherein the volume ratio of the water phase extracted each time to the petroleum ether is 1: 1.
Concentrating the petroleum ether extract phase at 50 deg.C under reduced pressure to obtain second extract, dissolving with cyclohexane at 55 deg.C, and filtering while hot. Wherein, the mass percentage concentration of the extract in the cyclohexane is 3.0%. Cooling the filtrate to room temperature, standing at 5 deg.C for 16 hr to crystallize and separate out honokiol, and filtering to obtain crystal.
Washing the crystal with appropriate amount of petroleum ether for 2 times, and vacuum drying in a vacuum drying oven at 65 deg.C under reduced pressure to obtain pure product of honokiol.
Example 2
Extracting the cortex Magnolia officinalis powder with petroleum ether under reflux at 70 deg.C for 2 times, the first time for 1 hr, the second time for 0.5 hr, and mixing filtrates. Wherein the granularity of the officinal magnolia powder is 50 meshes, and the mass volume ratio of the officinal magnolia powder extracted twice to the petroleum ether is 1:12 and 1:6(W/V) respectively.
Concentrating the extract filtrate under reduced pressure at 55 deg.C to obtain first extract, dissolving the first extract with 1M potassium hydroxide solution, filtering, extracting the filtrate with ethyl acetate for 2 times, and separating to obtain the residual water phase. Wherein the volume ratio of the ethyl acetate to the filtrate in each extraction is 1: 1.
Adjusting pH of the extracted water phase to 9.0 with 2M hydrochloric acid, extracting with petroleum ether for 2 times, and separating to obtain petroleum ether phase. Wherein the volume ratio of the water phase extracted each time to the petroleum ether is 1: 1.
Vacuum concentrating petroleum ether extract phase at 55 deg.C to obtain second extract, dissolving with cyclohexane at 60 deg.C, and filtering while hot. Wherein, the mass percentage concentration of the extract in the cyclohexane is 3.5%. Standing the filtrate at 10 deg.C for 12 hr to crystallize and separate out honokiol, and filtering to obtain crystal.
Washing the crystal with petroleum ether for 3 times, and vacuum drying in vacuum drying oven at 80 deg.C under reduced pressure to obtain pure product of honokiol.
Example 3
Extracting the cortex Magnolia officinalis powder with petroleum ether under reflux at 80 deg.C for 2 times, each time for 1 hr. Wherein the granularity of the officinal magnolia powder is 60 meshes, and the mass volume ratio of the officinal magnolia powder extracted twice to the petroleum ether is 1:10 and 1:5(W/V) respectively.
Concentrating the extract filtrate under reduced pressure at 60 deg.C to obtain first extract, dissolving the first extract with 2M potassium hydroxide solution, filtering, extracting the filtrate with petroleum ether for 2 times, and separating to obtain the residual water phase. Wherein the volume ratio of the petroleum ether to the filtrate in each extraction is 1: 2.
Adjusting pH of the extracted water phase to 10.0 with 4M hydrochloric acid, extracting with petroleum ether for 3 times, and separating to obtain petroleum ether phase. Wherein the volume ratio of the water phase extracted each time to the petroleum ether is 1: 1.
Vacuum concentrating petroleum ether extract phase at 60 deg.C to obtain second extract, dissolving with cyclohexane at 60 deg.C, and filtering while hot. Wherein the mass percentage concentration of the extract in the cyclohexane is 4.0%. Standing the filtrate at 15 deg.C for 10 hr to crystallize and separate out honokiol, and filtering to obtain crystal.
Washing the crystal with petroleum ether for 3 times, and vacuum drying in vacuum drying oven at 70 deg.C under reduced pressure to obtain pure product of honokiol.
Test example 1
The purity and yield of honokiol prepared in examples 1-3 are shown in the following table:
TABLE 1 purity and yield results for honokiol
| Purity (%) | Yield (%) | |
| Example 1 | 99.5 | 70 |
| Example 2 | 99.1 | 68 |
| Example 3 | 98.7 | 65 |
As can be seen from Table 1, the honokiol prepared in the embodiments 1-3 of the invention has high purity, which is greater than 98%, and has high yield. The preparation methods provided in examples 1 to 3 are scientific and reasonable.
As can be seen from fig. 1 and 2, in the preparation process, the color of the extract solution continuously becomes lighter, and the finally prepared honokiol is colorless transparent flaky crystals.
HPLC detection of purity of honokiol prepared in Experimental example 2
1. Preparation of sample solution
Preparing a standard solution: accurately weighing magnolol and honokiol reference substance about 20mg, dissolving with methanol to desired volume to obtain 1:1 mixed solution of about 100ug/mL, and filtering with 0.45um filter membrane to obtain reference substance solution to be measured.
Preparing a sample solution: precisely weighing about 20mg of the honokiol sample provided by the embodiment 1-3, fully dissolving the honokiol sample with methanol to a constant volume to prepare a solution of about 100ug/mL, and filtering the solution with a 0.45um filter membrane to obtain a sample solution to be detected.
Detection was performed by HPLC.
2. Chromatographic conditions for HPLC determination:
LC-300 high performance liquid chromatograph (Wuhansai Selfv technologies, Inc.); a chromatographic column: thermo C18(4.6X 250mm, 5 μm); column temperature: 30 ℃; mobile phase: 0-5min, methanol-water (80:20), 5-10min, methanol-water (80:20 → 95:5), 10-15min methanol-water (95: 5); flow rate: 1 mL/min; detection wavelength: 294 nm; sample introduction amount: 20 μ L.
3. Measurement results
The results (as shown in fig. 3 and fig. 4) show that the purity of honokiol prepared in examples 1-3 is over 98% relative to the standard (HPLC purity is greater than or equal to 98%), and the purity is slightly higher than the standard.
The embodiments described above are some, but not all embodiments of the invention. The detailed description of the embodiments of the present invention is not intended to limit the scope of the invention as claimed, but is merely representative of selected embodiments of the invention. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Claims (4)
1. A method for separating and preparing honokiol from magnolia officinalis is characterized by comprising the following steps: carrying out hot reflux extraction on the magnolia officinalis medicinal powder by adopting petroleum ether, and concentrating the hot reflux liquid under reduced pressure to obtain a first extract; the dosage ratio of the magnolia officinalis powder to the petroleum ether is 1: 15-20 (W/V);
dissolving and filtering the first extract by using an alkali solution, extracting the filtrate by using petroleum ether or ethyl acetate, and taking an extracted water phase; the dosage ratio of the first extract to the alkali liquor is 1: 10-20 (W/V), the concentration of the alkali liquor is 0.5-2M, and the first extract and the alkali liquor are fully stirred, dissolved and filtered; extracting the alkali-soluble filtrate of the first extract for 2-3 times by using petroleum ether or ethyl acetate with a volume ratio of 1: 1-2 (V/V), and taking an extracted water phase;
adjusting the pH value of the water phase to 8-10, and extracting the water phase for 2-3 times by using petroleum ether with a volume ratio of 1: 1-2 (V/V);
concentrating the petroleum ether extract at 50-60 ℃ under reduced pressure to obtain a second extract;
and dissolving and filtering the second extract by using a cyclohexane solution at the temperature of 55-60 ℃, standing overnight at the temperature of 5-15 ℃ for crystallization, filtering crystals, washing for 2-3 times by using petroleum ether, and drying in vacuum at the temperature of 60-80 ℃ to obtain the honokiol.
2. The method for separating and preparing honokiol from magnolia officinalis as claimed in claim 1, wherein the magnolia officinalis powder has a particle size of 40-60 meshes.
3. The method for separating and preparing honokiol from magnolia officinalis as claimed in claim 1, wherein the magnolia officinalis powder is extracted by hot reflux with the petroleum ether for 2-3 times at 60-80 ℃, each time for 0.5-1.5 h.
4. The method for separating and preparing honokiol from magnolia officinalis as claimed in claim 1, wherein the concentration of honokiol in the cyclohexane solution is 2.5-4.0% by weight.
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