CN107619422B - Method for preparing high-purity gossypetin-8-O-glucuronide - Google Patents

Method for preparing high-purity gossypetin-8-O-glucuronide Download PDF

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CN107619422B
CN107619422B CN201711024508.5A CN201711024508A CN107619422B CN 107619422 B CN107619422 B CN 107619422B CN 201711024508 A CN201711024508 A CN 201711024508A CN 107619422 B CN107619422 B CN 107619422B
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孙立权
张晓娇
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Beijing Institute of Technology BIT
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Abstract

The invention relates to a method for obtaining high-purity gossypetin-8-O-glucuronide by using a principle of complexation of metal zinc ions and flavonoids from an extract of Abelmoschus manihot. Belongs to the field of metal complex preparation, natural compound extraction and separation. The method comprises the following steps: extracting Abelmoschus manihot with alcohol water under the assistance of microwave; under the alkaline condition, the gossypetin-8-O-glucuronide in the Abelmoschus manihot and zinc salt form a stable complex; adding Ethylene Diamine Tetraacetic Acid (EDTA) which is more strongly complexed with zinc salt to decomplex the zinc salt-gossypetin-8-O-glucuronide complex, converting the zinc salt-gossypetin-8-O-glucuronide complex into free-form gossypetin-8-O-glucuronide with high purity, and greatly improving the concentration of the gossypetin-8-O-glucuronide in the solution. The method can quickly, safely and effectively separate and purify the gossypetin-8-O-glucuronide from the Abelmoschus manihot, and is favorable for realizing the industrial production of the gossypetin-8-O-glucuronide.

Description

Method for preparing high-purity gossypetin-8-O-glucuronide
Technical Field
The invention relates to a method for obtaining high-purity gossypetin-8-O-glucuronide by using a principle of complexation of metal zinc ions and flavonoids from an extract of Abelmoschus manihot. Belongs to the field of metal complex preparation, natural compound extraction and separation.
Background
Abelmoschus Manihot (Hibiscus Manihot L.) of Abelmoschus Manihot, sticky or slippery elm bark, which is an annual herbaceous Malvaceae (Malvaceae) Abelmoschus, is a wild endangered rare flower growing in the gap between cliffs, Abelmoschus Manihot is originally filed in Shundfu Zhi of Ming dynasty formation, but modern literature and data in China are not searched until being discovered again in the Chachentai region in 2003, and has the most health-care functions of eating, medicine, nutrition, beauty and slimming among more than 200 Abelmoschus Manihot plants (Chinese medicine evaluation, 2015, 32, 90-92).
Abelmoschus manihot has the reputation of a plant panda, contains various plant bioactive substances, and mainly comprises flavonoid compounds, vitamin E, unsaturated fatty acid, dietary fibers, trace elements and the like. These nutrients are necessary for human body but cannot be synthesized by itself, and need to be taken by diet, and in recent years, golden flower sunflower is concerned by all people as an important source for extracting flavonoids. Research shows that gossypetin-8-O-glucuronide is a flavonoid compound with the highest content in the flower of golden flower, is one of the main active ingredients of the flower of golden flower (Journal of chromatographic scientific, 2009, 47, 206-. The compound can be clinically used as a potential medicament for resisting diseases such as senile dementia, tumor diseases, cardiovascular diseases and the like (Neuroscience letters 2009, 461, 172-176). The structural formula of the gossypetin-8-O-glucuronide is shown as the following formula I:
Figure GDA0002468910420000011
at present, methods for separating and purifying flavones mainly comprise methods such as a solvent extraction method, a membrane separation method, a macroporous resin method, a column chromatography method and the like (Chinese test technology, 2007, 33, 22-25), but the methods have the problems of complicated purification method, overhigh cost, long production period, difficulty in industrial production and the like, and limit the application of the abelmoschus manihot flavones. By utilizing the characteristic that a flavonoid compound and a metal salt can form a stable complex, a method for quickly, safely, feasibly and effectively separating and purifying the gossypetin-8-O-glucuronide is developed. The complex is beneficial to the in-vivo transportation and absorption of corresponding metal salts by a human body, can help intake of flavonoid compounds, is a medicament with great development potential, and is worthy of further careful research, development and utilization. Therefore, the Abelmoschus manihot is used as an extraction raw material of the gossypetin-8-O-glucuronide, so that the comprehensive utilization value and the economic benefit of the Abelmoschus manihot are directly improved, and the Abelmoschus manihot has a good application prospect in the industries of medicines, foods or health care products and the like. At present, the preparation of high-purity gossypetin-8-O-glucuronide from Abelmoschus manihot is not reported.
The invention separates the gossypetin-8-O-glucuronide from the Abelmoschus manihot extract by using the characteristic that a flavonoid compound in the Abelmoschus manihot and a zinc salt form a stable complex. After the complex is precipitated and separated, complexing agent EDTA with a complexing effect stronger than that of the flavonoid compound is added to convert the complex-state flavone into free-state flavone with high purity, so that the high-purity gossypetin-8-O-glucuronide is obtained.
Disclosure of Invention
The invention aims to develop a method for effectively separating and purifying the gossypetin-8-O-glucuronide from the Abelmoschus manihot quickly, safely and feasible by utilizing the characteristic that a flavonoid compound and a metal zinc salt can form a stable complex.
The purpose of the invention is realized by the following technical scheme:
a method for obtaining high-purity gossypetin-8-O-glucuronide by using the complexing principle of zinc salt and flavonoids from an abelmoschus manihot extracting solution comprises the following steps:
A. precisely weighing 5.0g of dry crude powder of Abelmoschus manihot, performing microwave extraction for 15min under the conditions of 400W of power and 80 ℃, cooling to room temperature, performing suction filtration to obtain Abelmoschus manihot residues and supernatant, collecting the supernatant, and performing constant volume to a 250m L volumetric flask by using 70% ethanol solution to obtain a sample solution;
B. weighing Abelmoschus manihot sample solution, adjusting pH to 8.5-11.5 with alkaline solution, wherein the alkaline solution can be selected from sodium hydroxide solution, potassium hydroxide solution, sodium carbonate solution, ammonia water, etc. with certain concentration. Adding zinc salt with a certain mass concentration, wherein the zinc salt can be selected from zinc sulfate, zinc acetate, zinc chloride and the like, and the addition amount ensures that the mass ratio of the abelmoschus manihot sample to the zinc salt is 1/0.5-1/5. After the addition, the complex reaction time is 1-12 h. The temperature of the complex reaction is 10-70 ℃, and the precipitate generated by the complex reaction is centrifugally separated;
C. adding a certain mass of dissociating agent Ethylene Diamine Tetraacetic Acid (EDTA) and 10% -70% ethanol solution into the precipitate for decomplexation reaction, preferably 50% ethanol solution, wherein the addition amount ensures that the mass ratio of the zinc salt to the EDTA is 1/1-1/5, preferably 1/1. After the addition, the ultrasound is carried out for 0.5 to 4 hours, preferably for 0.5 hour. And (3) centrifugally separating precipitates generated after the decomplexation reaction, collecting supernate, and concentrating to obtain the high-purity gossypetin-8-O-glucuronide.
The extracting solution of the Abelmoschus manihot and the prepared high-purity gossypetin-8-O-glucuronide are analyzed by high performance liquid chromatography to obtain an analysis result, and a chromatogram is shown in a figure, wherein the adopted chromatographic conditions comprise a Waters HP L C high performance liquid chromatograph, a chromatographic column COSMOSI L C18(4.6mm × 200mm, 5 mu m), a mobile phase acetonitrile-0.1% formic acid solution gradient elution (0min, 15:85 v/v; 18min, 16:84 v/v; 26min, 20:80 v/v; 35min, 40:60 v/v; 40min, 40:60v/v), a flow rate of 1.0m L/min, a detection wavelength of 360nm, a sample introduction amount of 10 mu L and a column temperature of room temperature.
The invention achieves the following beneficial results:
1. the Abelmoschus manihot extract is not required to be further processed, the zinc salt solution is directly added, and the pH is adjusted to complex the zinc salt with the gossypetin-8-O-glucuronide in the extract, so that the processing steps are simplified, the operation time is saved, the consumption of manpower and energy is reduced, and the like, and the preparation efficiency and the economic benefit are improved;
2. the zinc salt such as zinc sulfate is adopted, so that the cost is low, the zinc sulfate is non-toxic and harmless, the danger degree is reduced, and the recovery of an extraction solvent is facilitated;
3. by adding complexing agent EDTA which has stronger complexing effect than flavonoid compounds, the complexing-state flavone is converted into free-state flavone with high purity, and the concentration of the gossypetin-8-O-glucuronide in the organic solution is greatly improved. The large-scale industrial production of purified gossypetin-8-O-glucuronide is facilitated through the combined operation.
Drawings
FIG. 1 is a HP L C spectrum of gossypetin-8-O-glucuronide in an unpurified Abelmoschus manihot extract.
FIG. 2 is a graph of HP L C of gossypetin-8-O-glucuronide in a sample purified by complex treatment.
The specific implementation mode is as follows:
the method for extracting flavonoids from Abelmoschus manihot and preparing high-purity gossypetin-8-O-glucuronide according to the present invention will be further described with reference to the accompanying drawings and specific examples, so as to enable those skilled in the art to understand the present invention more
The invention is not limited thereto.
Example 1:
A. precisely weighing 5.0g of dry crude powder of Abelmoschus manihot, performing microwave extraction for 15min under the conditions of 400W of power and 80 ℃, cooling to room temperature, performing suction filtration to obtain Abelmoschus manihot residues and supernatant, collecting the supernatant, and performing constant volume to a 250m L volumetric flask by using 70% ethanol solution to obtain a sample solution;
B. measuring L Abelmoschus manihot sample solution with the volume of 10m, adjusting the pH value to 9.5 by using sodium hydroxide solution, adding zinc sulfate with certain mass concentration, wherein the addition amount ensures that the mass ratio of the Abelmoschus manihot sample to the zinc sulfate is 1/0.5, performing complexation reaction for 3 hours at the temperature of 30 ℃ after addition, and performing centrifugal separation complexation reaction to generate precipitate;
C. adding a certain mass of dissociation agent Ethylene Diamine Tetraacetic Acid (EDTA) and 50% ethanol solution into the precipitate for decomplexation reaction, wherein the addition amount ensures that the mass ratio of zinc sulfate to EDTA is 1/1. After adding, carrying out ultrasonic treatment for 0.5h, centrifugally separating precipitate generated after decomplexation reaction, collecting supernatant, and concentrating to obtain high-purity gossypetin-8-O-glucuronide with the purity of 82.16%.
Example 2:
A. precisely weighing 5.0g of dry crude powder of Abelmoschus manihot, performing microwave extraction for 15min under the conditions of 400W of power and 80 ℃, cooling to room temperature, performing suction filtration to obtain Abelmoschus manihot residues and supernatant, collecting the supernatant, and performing constant volume to a 250m L volumetric flask by using 70% ethanol solution to obtain a sample solution;
B. measuring L Hibiscus manihot sample solution with the volume of 10m, adjusting the pH value to 11.5 by using sodium carbonate solution, adding zinc chloride with certain mass concentration, wherein the addition amount ensures that the mass ratio of Hibiscus manihot sample to zinc chloride is 1/0.5, after the addition, the complexation reaction time is 12h, the complexation reaction temperature is 70 ℃, and precipitates are generated after centrifugal separation complexation reaction;
C. adding a certain mass of dissociating agent Ethylene Diamine Tetraacetic Acid (EDTA) and 30% ethanol solution into the precipitate for decomplexation reaction, wherein the addition amount ensures that the mass ratio of the zinc chloride to the EDTA is 1/5. After adding, carrying out ultrasonic treatment for 4h, centrifugally separating precipitate generated after decomplexation reaction, collecting supernatant, and concentrating to obtain high-purity gossypetin-8-O-glucuronide with the purity of 73.79%.
Example 3:
A. precisely weighing 5.0g of dry crude powder of Abelmoschus manihot, performing microwave extraction for 15min under the conditions of 400W of power and 80 ℃, cooling to room temperature, performing suction filtration to obtain Abelmoschus manihot residues and supernatant, collecting the supernatant, and performing constant volume to a 250m L volumetric flask by using 70% ethanol solution to obtain a sample solution;
B. measuring 10m L Abelmoschus manihot sample solution, adjusting pH value to 11.5 with potassium hydroxide solution, adding zinc acetate with certain mass concentration, wherein the addition amount ensures that the mass ratio of Abelmoschus manihot sample and zinc acetate is 1/5, after the addition, the complexation reaction time is 1h, the complexation reaction temperature is 10 ℃, and precipitates are generated after centrifugal separation complexation reaction;
C. adding a certain mass of dissociating agent Ethylene Diamine Tetraacetic Acid (EDTA) and 10% ethanol solution into the precipitate for decomplexation reaction, wherein the addition amount ensures that the mass ratio of the zinc acetate to the EDTA is 1/5. After adding, carrying out ultrasonic treatment for 1h, centrifugally separating precipitate generated after decomplexation reaction, collecting supernatant, and concentrating to obtain high-purity gossypetin-8-O-glucuronide with the purity of 71.43%.
Example 4:
A. precisely weighing 5.0g of dry crude powder of Abelmoschus manihot, performing microwave extraction for 15min under the conditions of 400W of power and 80 ℃, cooling to room temperature, performing suction filtration to obtain Abelmoschus manihot residues and supernatant, collecting the supernatant, and performing constant volume to a 250m L volumetric flask by using 70% ethanol solution to obtain a sample solution;
B. measuring L Abelmoschus manihot sample solution with a volume of 10m, adjusting the pH value to 9.5 by ammonia water, adding zinc sulfate with a certain mass concentration, wherein the addition amount ensures that the mass ratio of the Abelmoschus manihot sample to the zinc sulfate is 1/0.5, after the addition, the complexation reaction time is 5h, the complexation reaction temperature is 50 ℃, and precipitates are generated after centrifugal separation complexation reaction;
C. and adding a certain mass of dissociation agent Ethylene Diamine Tetraacetic Acid (EDTA) and 70% ethanol solution into the precipitate for decomplexation reaction, wherein the addition amount ensures that the mass ratio of zinc sulfate to EDTA is 1/1. After adding, carrying out ultrasonic treatment for 4h, centrifugally separating precipitate generated after decomplexation reaction, collecting supernatant, and concentrating to obtain high-purity gossypetin-8-O-glucuronide with the purity of 75.72%.
Example 5:
A. precisely weighing 5.0g of dry crude powder of Abelmoschus manihot, performing microwave extraction for 15min under the conditions of 400W of power and 80 ℃, cooling to room temperature, performing suction filtration to obtain Abelmoschus manihot residues and supernatant, collecting the supernatant, and performing constant volume to a 250m L volumetric flask by using 70% ethanol solution to obtain a sample solution;
B. measuring L Abelmoschus manihot sample solution with the volume of 10m, adjusting the pH value to 10.5 by using sodium hydroxide, adding zinc sulfate with a certain mass concentration, wherein the addition amount ensures that the mass ratio of the Abelmoschus manihot sample to the zinc sulfate is 1/1, after the addition, the complexation reaction time is 5h, the complexation reaction temperature is 50 ℃, and precipitates are generated after centrifugal separation complexation reaction;
C. adding a certain mass of dissociation agent Ethylene Diamine Tetraacetic Acid (EDTA) and 50% ethanol solution into the precipitate for decomplexation reaction, wherein the addition amount ensures that the mass ratio of zinc sulfate to EDTA is 1/1. After adding, carrying out ultrasonic treatment for 1h, centrifugally separating precipitate generated after decomplexation reaction, collecting supernatant, and concentrating to obtain high-purity gossypetin-8-O-glucuronide with the purity of 77.54%.
Example 6:
A. precisely weighing 5.0g of dry crude powder of Abelmoschus manihot, performing microwave extraction for 15min under the conditions of 400W of power and 80 ℃, cooling to room temperature, performing suction filtration to obtain Abelmoschus manihot residues and supernatant, collecting the supernatant, and performing constant volume to a 250m L volumetric flask by using 70% ethanol solution to obtain a sample solution;
B. measuring L Abelmoschus manihot sample solution with the volume of 10m, adjusting the pH value to 8.5 by using sodium hydroxide, adding zinc sulfate with a certain mass concentration, wherein the addition amount ensures that the mass ratio of the Abelmoschus manihot sample to the zinc sulfate is 1/2, after the addition, the complexation reaction time is 7h, the complexation reaction temperature is 50 ℃, and precipitates are generated after centrifugal separation complexation reaction;
C. adding a certain mass of dissociation agent Ethylene Diamine Tetraacetic Acid (EDTA) and 50% ethanol solution into the precipitate for decomplexation reaction, wherein the addition amount ensures that the mass ratio of zinc sulfate to EDTA is 1/2. After adding, carrying out ultrasonic treatment for 1h, centrifugally separating precipitate generated after decomplexation reaction, collecting supernatant, and concentrating to obtain high-purity gossypetin-8-O-glucuronide with the purity of 65.49%.
The above 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, and any modifications, equivalents, improvements and the like that fall within the spirit and principle of the present invention are intended to be included therein.

Claims (9)

1. A method for preparing high-purity gossypetin-8-O-glucuronide is characterized by comprising the following steps:
A. precisely weighing 5.0g of dry crude powder of Abelmoschus manihot, performing microwave extraction for 15min under the conditions of 400W of power and 80 ℃, cooling to room temperature, performing suction filtration to obtain Abelmoschus manihot residues and supernatant, collecting the supernatant, and performing constant volume to a 250m L volumetric flask by using 70% ethanol solution to obtain a sample solution;
B. weighing a Abelmoschus manihot sample solution, and adjusting the pH value to 8.5-11.5 by using an alkaline solution, wherein the alkaline solution is a sodium hydroxide solution, a potassium hydroxide solution, a sodium carbonate solution and ammonia water with certain concentrations; adding a zinc salt solution with a certain concentration, wherein the zinc salt is zinc sulfate, zinc acetate and zinc chloride, and the addition amount ensures that the mass ratio of the abelmoschus manihot sample to the zinc salt is 1/0.5-1/5; after the addition, the complex reaction time is 1-12 h; the temperature of the complex reaction is 10-70 ℃, and the precipitate generated by the complex reaction is centrifugally separated;
C. adding a certain mass of dissociating agent EDTA and 10% -70% ethanol solution into the precipitate to perform decomplexation reaction, wherein the addition amount ensures that the mass ratio of zinc salt to EDTA is 1/1-1/5; after adding, carrying out ultrasonic treatment for 0.5-4 h; and (3) centrifugally separating precipitates generated after the decomplexation reaction, collecting supernate, and concentrating to obtain the high-purity gossypetin-8-O-glucuronide.
2. The method for preparing high-purity gossypetin-8-O-glucuronide according to claim 1, characterized in that: the alkaline solution is sodium hydroxide solution; the pH was adjusted to 9.5.
3. The method for preparing high-purity gossypetin-8-O-glucuronide according to claim 1, characterized in that: the zinc salt used in the complexing reaction is zinc sulfate.
4. The method for preparing high-purity gossypetin-8-O-glucuronide according to claim 1, characterized in that: the mass ratio of the mallow sample to the zinc salt in the complexation reaction is 1/1.
5. The method for preparing high-purity gossypetin-8-O-glucuronide according to claim 1, characterized in that: the complexing reaction time is 3 h.
6. The method for preparing high-purity gossypetin-8-O-glucuronide according to claim 1, characterized in that: the temperature of the complexation reaction was 30 ℃.
7. The method for preparing high-purity gossypetin-8-O-glucuronide according to claim 1, characterized in that: the solvent used for the decomplexation reaction is 50% ethanol solution.
8. The method for preparing high-purity gossypetin-8-O-glucuronide according to claim 1, characterized in that: the mass ratio of the zinc salt to the EDTA in the decomplexation reaction was 1/1.
9. The method for preparing high-purity gossypetin-8-O-glucuronide according to claim 1, characterized in that: the ultrasound in the decomplexation reaction is 0.5 h.
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