CN108191933B - Method for preparing new astilbin by taking rhizoma smilacis glabrae as raw material - Google Patents
Method for preparing new astilbin by taking rhizoma smilacis glabrae as raw material Download PDFInfo
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/06—Benzopyran radicals
- C07H17/065—Benzo[b]pyrans
- C07H17/07—Benzo[b]pyran-4-ones
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
- C07H1/06—Separation; Purification
- C07H1/08—Separation; Purification from natural products
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Abstract
The invention provides a method for preparing new astilbin by taking glabrous greenbrier rhizome as a raw material. According to the technical scheme, the mutual conversion relation among four isomers of astilbin in glabrous greenbrier rhizome is investigated firstly, the isomerization reaction of the astilbin to new astilbin can be started under specific pH and temperature conditions in the presence of ascorbic acid, and based on the beneficial discovery, the invention takes the isomerization direction, the conversion degree, the product decomposition degree and the like as the guide and gropes the optimal reaction condition; under this condition, astilbin is mainly isomerized into new astilbin, and the decomposition speed is slow. Based on the method, the invention further designs the front-end leaching condition and the subsequent purification method. By applying the method, the astilbin in the glabrous greenbrier rhizome can be mostly converted into the new astilbin, so that the content of the new astilbin in the glabrous greenbrier rhizome extract is improved by nearly 9 times, and the efficiency of separating and purifying the new astilbin from the glabrous greenbrier rhizome is greatly improved.
Description
Technical Field
The invention relates to the technical field of extraction of plant active ingredients, and in particular relates to a method for preparing new astilbin by taking rhizoma smilacis glabrae as a raw material.
Background
Astilbin, namely 2(R) 3(R) -3 ', 4', 5,7-4 hydroxysultone-3-alpha-L-rhamnopyranose, is the main functional component of the traditional Chinese medicine rhizoma smilacis glabrae. Astilbin has various biological activities, such as selective immunosuppression, fat metabolism regulation, antioxidation, liver protection, etc.
According to the molecular structure of astilbin, the astilbin has stereoisomerism at C2 and C3, and has four isomers of 2(R):3(R) (astilbin), 2(S):3(S) (neoastilbin), 2(S):3(R) (neoisoastilbin) and 2(R):3(S) (isoastilbin). The isomerization of a compound may affect its biological activity, and some drugs have completely different pharmacological effects on both enantiomers. It is therefore necessary to conduct research on the biological activity of its isomers.
The glabrous greenbrier rhizome contains four isomers of astilbin at the same time, but the astilbin content is the highest, and the other three isomers are very low, so that only an extract with the astilbin occupying the most important components can be obtained by adopting a conventional leaching method, separation between the isomers cannot be realized, and the proportion of the new astilbin cannot be improved. Therefore, the method for directly separating astilbin from glabrous greenbrier rhizome is mature at present, and the method for obtaining new astilbin from the glabrous greenbrier rhizome is only reported, and even if researchers achieve certain success, the yield is in a lower level. This greatly hinders the study of the properties and the deep application of new astilbin.
Disclosure of Invention
The invention aims to provide a method for preparing new astilbin by taking rhizoma smilacis glabrae as a raw material aiming at the technical defects of the prior art, so as to solve the technical problem that the prior art is lack of the method.
The invention also aims to solve the technical problem of improving the yield in the method for preparing the new astilbin by taking the glabrous greenbrier rhizome as the raw material.
The invention also aims to solve the technical problem that the smilax glabra extract obtained by the conventional extraction method contains astilbin as a main component, and the ratio of the new astilbin is very low.
In order to achieve the technical purpose, the invention adopts the following technical scheme:
a method for preparing new astilbin by taking rhizoma smilacis glabrae as a raw material comprises the following steps:
1) taking the poria cocos, crushing, sieving with a 20-40-mesh sieve, taking an ethanol water solution with the concentration of 10-90% (v/v) as an extracting agent, mixing the sieved substance and the extracting agent according to the ratio of the mass of the sieved substance to the volume of the extracting agent of 1:20(kg: L), stirring for 60min at room temperature, and filtering to obtain a filtrate;
2) vacuum concentrating the filtrate obtained in the step 1) at 60 ℃, and recovering ethanol to obtain a concentrated solution;
3) adjusting the pH value of the concentrated solution obtained in the step 2) to 5-9, adding ascorbic acid to the concentrated solution until the final concentration is 0.1-10 mM, and standing and reacting for 6-16 h in an environment at 50-90 ℃.
Preferably, the method further comprises the following step 4): taking the product obtained in the step 3), and extracting a pure new astilbin product from the product by utilizing resin adsorption, recrystallization, silica gel column chromatography, semi-preparative chromatography or high-speed counter-current chromatography.
Preferably, step 4) specifically comprises the following operations: taking the product obtained in the step 3), flowing through an H103 macroporous resin bed for adsorption, then eluting with an ethanol solution with the volume 4 times that of the column bed, and collecting the eluent; collecting new astilbin component in the eluate by semi-preparative chromatography, and freeze drying.
Preferably, the volume of the macroporous resin bed in the step 4) is 160ml, and the height of the bed is 60 cm; the concentration of the ethanol solution is 50% (v/v).
Preferably, the concentration of the ethanol aqueous solution in the step 1) is 50% (v/v).
Preferably, the pH of the concentrate in step 3) is adjusted to 8.0.
Preferably, the final concentration of ascorbic acid in step 3) is 1 mM.
Preferably, the standing in step 3) is performed under water bath conditions.
Preferably, the temperature of the standing in the step 3) is 80 ℃.
Preferably, the standing time in the step 3) is 10 h.
In the technical scheme, the smilax glabra is a traditional Chinese medicinal material named smilax glabra, and the nature of the smilax glabra is dried rhizome of smilax glabra in liliaceae. The screened material refers to a part which has a smaller particle size and thus passes through a screen after being screened by the screen.
The invention provides a method for preparing new astilbin by taking glabrous greenbrier rhizome as a raw material, and the technical scheme firstly discovers that because four isomers in the glabrous greenbrier rhizome material have natural content levels and chemical properties are very close to each other through experimental means, one isomer is difficult to directionally extract by only improving a solvent extraction process. Under the condition, the invention considers the mutual conversion relation of four isomers, and unexpectedly discovers that the isomerization reaction of astilbin to new astilbin can be started under the specific conditions of pH and temperature in the presence of ascorbic acid; under this condition, astilbin is mainly isomerized into new astilbin, and the decomposition speed is slow. Based on the method, the invention further designs the front-end leaching condition and the subsequent purification method. By applying the method, the astilbin in the glabrous greenbrier rhizome can be mostly converted into the new astilbin, so that the content of the new astilbin in the glabrous greenbrier rhizome extract is improved by nearly 9 times, and the efficiency of separating and purifying the new astilbin from the glabrous greenbrier rhizome is greatly improved.
Drawings
FIG. 1 is a high performance liquid chromatogram of an extract of Smilax glabra Linne before isomerization according to an embodiment of the present invention; in the figure: peak 1 is new astilbin; the peak 2 is astilbin.
FIG. 2 is a high performance liquid chromatogram of an isomerized rhizoma Smilacis Glabrae extract according to an embodiment of the present invention; in the figure: peak 1 is new astilbin; the peak 2 is astilbin.
Detailed Description
Hereinafter, specific embodiments of the present invention will be described in detail. Well-known structures or functions may not be described in detail in the following embodiments in order to avoid unnecessarily obscuring the details.
Approximating language, as used herein in the following examples, may be applied to identify quantitative representations that could permissibly vary in number without resulting in a change in the basic function. Accordingly, a numerical value modified by a language such as "about", "left or right" is not limited to the precise numerical value itself. In some embodiments, "about" indicates that the value allowed for correction varies within plus or minus ten percent (10%), for example, "about 100" indicates that any value between 90 and 110 is possible. Further, in the expression "about a first value to a second value", both the first and second values are corrected at about the same time. In some cases, the approximating language may be related to the precision of a measuring instrument.
Unless defined otherwise, technical and scientific terms used in the following examples have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs.
The test reagent consumables used in the following examples are all conventional biochemical reagents unless otherwise specified; the experimental methods are conventional methods unless otherwise specified; in the quantitative tests in the following examples, three repeated experiments are set, and the results are averaged; in the following examples,% is by mass unless otherwise specified.
Example 1
Pulverizing 1kg rhizoma Smilacis Glabrae, sieving with 40 mesh sieve, adding 20L ethanol water solution with concentration of 50%, stirring and extracting at room temperature for 60min, and filtering to obtain extractive solution. FIG. 1 shows HPLC of an extract of Smilax glabra. In the figure, peak 1 is new astilbin, and peak 2 is astilbin. The content of astilbin in the glabrous greenbrier rhizome is 2.2 percent and the content of new astilbin is 0.17 percent through the high performance liquid chromatography determination, namely, 1kg of the glabrous greenbrier rhizome contains 22g of the astilbin and 1.7g of the new astilbin; it can be seen that the content of astilbin in smilax glabra is the highest, while the content of new astilbin is very low.
Concentrating rhizoma Smilacis Glabrae extractive solution, removing ethanol, adjusting pH to 8, adding ascorbic acid with final concentration of 1mM, and standing in 80 deg.C water bath for 10 hr for isomerization reaction. FIG. 2 shows HPLC of the Smilax glabra L.extract after isomerization. In the figure, peak 1 is new astilbin, and peak 2 is astilbin. The astilbin content is obviously reduced after isomerization reaction; the new astilbin content is obviously increased and becomes the main flavone component. The total amount of astilbin in 1kg of rhizoma Smilacis Glabrae after isomerization is reduced to 3.9g, and the total amount of astilbin is increased to 16.7g by high performance liquid chromatography. The content of the new astilbin in the glabrous greenbrier rhizome is improved by 8.8 times, and the new astilbin is replaced to become the most main flavone component in the extracting solution, so that convenience is brought to the subsequent separation and purification of the new astilbin from the glabrous greenbrier rhizome, and the yield of the new astilbin can be greatly improved.
TABLE 1 comparison of astilbin and neoastilbin content in 1kg of Smilax glabra before and after isomerization reaction
Experiments show that the isomerization speed is reduced due to the reduction of the pH value, and the isomerization reaction hardly occurs under the condition of the pH value of 3-4; while too high pH (>9) can lead to instability of the flavone and rapid decomposition of astilbin and isomers thereof. The increased temperature increases the rate of isomerization of astilbin, but also increases its rate of decomposition. The ascorbic acid is added, so that the conversion rate of the new astilbin can be effectively improved, the stability of the flavone is improved, and the decomposition rate of the flavone is reduced.
Example 2
(1) Pulverizing 1kg rhizoma Smilacis Glabrae, sieving with 40 mesh sieve, adding 20L 60% ethanol solution, stirring at room temperature for 60min, and filtering with 200 mesh filter cloth to obtain extractive solution.
(2) Vacuum concentrating the extracting solution obtained in the step (1) at the temperature of 60 ℃, and recovering ethanol to obtain 4L of concentrated solution; the concentrated solution contains total astilbin 22g and new astilbin 1.7g, determined by high performance liquid chromatography.
(3) Adjusting the pH of the concentrated solution obtained in the step (2) to 7 by using 1mol/L NaOH solution, adding 0.704g of ascorbic acid, wherein the final concentration of the ascorbic acid is 1mM, and placing the mixture in a water bath at 80 ℃ for 10 hours to perform isomerization reaction. The concentrated solution contains total astilbin 3.9g and new astilbin 16.7g, determined by high performance liquid chromatography. The concentration of new astilbin is improved by 8.8 times, and the new astilbin is replaced by the astilbin to become the most main flavone component in the extracting solution, thereby bringing convenience for subsequent separation and purification of the new astilbin.
(4) Enabling the solution obtained in the step (3) to flow through an H103 macroporous resin bed for adsorption operation; the bed volume was 160ml and the bed height was 60 cm. Then, the elution was carried out with 50% ethanol in a volume of 4 times the bed volume, and the eluate was collected.
(5) And (4) collecting new astilbin components in the eluent in the step (4) by using semi-preparative chromatography, concentrating, and freeze-drying to obtain 16g of new astilbin with the purity of more than 98%.
Example 3
A method for preparing new astilbin by taking rhizoma smilacis glabrae as a raw material comprises the following steps:
1) pulverizing Poria, sieving with 20 mesh sieve, taking 10% (v/v) ethanol water solution as extractant, mixing the sieved material with the extractant at a ratio of the mass of the sieved material to the volume of the extractant of 1:20(kg: L), stirring at room temperature for 60min, and filtering to obtain filtrate;
2) vacuum concentrating the filtrate obtained in the step 1) at 60 ℃, and recovering ethanol to obtain a concentrated solution;
3) adjusting the pH of the concentrated solution obtained in the step 2) to 5, adding ascorbic acid to the solution to a final concentration of 0.1mM, and standing the solution for reaction for 16h at 50 ℃.
Example 4
A method for preparing new astilbin by taking rhizoma smilacis glabrae as a raw material comprises the following steps:
1) pulverizing Poria, sieving with 40 mesh sieve, taking 90% (v/v) ethanol water solution as extractant, mixing the sieved material and the extractant at a ratio of the mass of the sieved material to the volume of the extractant of 1:20(kg: L), stirring at room temperature for 60min, and filtering to obtain filtrate;
2) vacuum concentrating the filtrate obtained in the step 1) at 60 ℃, and recovering ethanol to obtain a concentrated solution;
3) adjusting the pH of the concentrated solution obtained in the step 2) to 9, adding ascorbic acid to the solution to a final concentration of 10mM, and standing the solution for reaction for 6 hours at 90 ℃.
The embodiments of the present invention have been described in detail, but the description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention. Any modification, equivalent replacement, and improvement made within the scope of the application of the present invention should be included in the protection scope of the present invention.
Claims (10)
1. A method for preparing new astilbin by taking rhizoma smilacis glabrae as a raw material is characterized by comprising the following steps:
1) taking poria cocos, crushing, sieving with a 20-40-mesh sieve, taking an ethanol water solution with the volume concentration of 10-90% as an extracting agent, mixing the sieved substance and the extracting agent according to the ratio of the mass of the sieved substance to the volume of the extracting agent of 1:20, wherein the mass unit is kg and the volume unit is L, stirring for 60min at room temperature, and filtering to obtain a filtrate;
2) vacuum concentrating the filtrate obtained in the step 1) at 60 ℃, and recovering ethanol to obtain a concentrated solution;
3) adjusting the pH value of the concentrated solution obtained in the step 2) to 5-9, adding ascorbic acid to the concentrated solution until the final concentration is 0.1-10 mM, and standing and reacting for 6-16 h in an environment at 50-90 ℃.
2. The method for preparing astilbin from smilax glabra as a raw material according to claim 1, which is characterized by further comprising the following step 4): taking the product obtained in the step 3), and extracting a pure new astilbin product from the product by utilizing resin adsorption, recrystallization, silica gel column chromatography, semi-preparative chromatography or high-speed counter-current chromatography.
3. The method for preparing astilbin from smilax glabra as a raw material according to claim 2, wherein the step 4) comprises the following steps: taking the product obtained in the step 3), flowing through an H103 macroporous resin bed for adsorption, then eluting with an ethanol solution with the volume 4 times that of the column bed, and collecting the eluent; collecting new astilbin component in the eluate by semi-preparative chromatography, and freeze drying.
4. The method for preparing astilbin from rhizoma Smilacis Glabrae as raw material according to claim 3, wherein the macroporous resin bed in step 4) has a bed volume of 160ml and a bed height of 60 cm; the volume concentration of the ethanol solution is 50%.
5. The method for preparing astilbin from smilax glabra as claimed in claim 1, wherein the ethanol aqueous solution of step 1) has a volume concentration of 50%.
6. The method for preparing astilbin from smilax glabra as claimed in claim 1, wherein the pH of the concentrated solution in the step 3) is adjusted to 8.0.
7. The method for preparing neoastilbin from smilax glabra as claimed in claim 1, wherein the final concentration of ascorbic acid in step 3) is 1 mM.
8. The method for preparing astilbin from smilax glabra as claimed in claim 1, wherein the standing in step 3) is performed in water bath.
9. The method for preparing astilbin from glabrous greenbrier rhizome as a raw material according to claim 1, wherein the temperature of the standing in the step 3) is 80 ℃.
10. The method for preparing astilbin from smilax glabra as a raw material according to claim 1, wherein the standing time in the step 3) is 10 hours.
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| Isomerization of astilbin. I;Tominaga, Toshio;《Yakugaku Zasshi》;19601231;第80卷(第9期);1202-1206 * |
| Qing-Feng Zhang，等.Aqueous Stability of Astilbin: Effects of pH, Temperature, and Solvent.《J. Agric. Food Chem.》.2013,第61卷12085-12091. * |
| Stereospecific high-performance liquid chromatography of taxifolin, applications in pharmacokinetics, and determination in tu fu ling (Rhizoma smilacis glabrae) and apple (Malus × domestica);Karina R. Vega-Villa，等;《Biomed. Chromatogr.》;20090305;第23卷;638-646 * |
| Structural Relationships and Interconversions of Isomeric Astilbins;William Gaffield，等;《J. Org. Chem.》;19751231;第40卷(第8期);1057-1061 * |
| 常见食品组分及金属离子对落新妇苷稳定性的影响;张丽，等;《食品与发酵工业》;20171225;第43卷(第12期);66-70 * |
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