CN107759648B - Method for separating and purifying hyperoside and isoquercitrin from abelmoschus manihot - Google Patents
Method for separating and purifying hyperoside and isoquercitrin from abelmoschus manihot Download PDFInfo
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Abstract
The invention relates to a method for separating and purifying hyperin and isoquercitrin from abelmoschus manihot, belonging to the field of extraction and separation of natural compounds. The method comprises the following steps: heating and refluxing to extract flavone from Abelmoschus manihot; under alkaline conditions, the zinc salt and flavonoid substances except hyperin and isoquercitrin in the abelmoschus manihot form stable complex precipitates; centrifuging to remove complex precipitate; concentrating the supernatant to obtain high purity hyperoside and isoquercitrin. The method can quickly, efficiently and safely separate and purify hyperoside and isoquercitrin from Abelmoschus manihot, and is beneficial to realizing industrial production of hyperoside and isoquercitrin.
Description
Technical Field
The invention relates to a method for separating and purifying hyperin and isoquercitrin from abelmoschus manihot. Specifically, starting from the Abelmoschus manihot extract, the method is developed for quickly, efficiently and safely separating and purifying the hyperin and isoquercitrin from the Abelmoschus manihot by removing other flavonoid compounds in the Abelmoschus manihot extract by utilizing the characteristics that the complexation capacity of the hyperin and isoquercitrin with zinc salt is weak and the complexation capacity of other flavonoid compounds with zinc salt is strong. Belongs to the field of natural compound extraction and separation.
Background
Hyperin is also known as quercetin-3-O-beta-D-galactopyranoside, isoquercitrin is also known as quercetin-3-O-beta-D-glucopyranoside, both are glycosides of quercetin, have the same aglycone and similar polarity, have a different configuration of a hydroxyl group only in the glycosyl part, the former is galactoside, the latter is glucoside, and the rest parts are completely the same and belong to flavonol glycoside compounds. (the Redandan institute, 2007, 46, 417-. Many pharmacological studies show that hyperoside has the effects of improving cardiovascular function, protecting cerebral ischemia/reperfusion injury, resisting oxidation and reduction, resisting inflammation, relieving pain and cough, reducing blood pressure and the like (Chinese pharmacy 2016, 27, 1415 and 1417), and isoquercitrin has the pharmacological activities of reducing blood pressure, resisting inflammation, resisting depression and the like (J. pharmaceutical practice 2011, 29, 272 and 274). The structural formula of hyperoside is shown as formula I below, and the structural formula of isoquercitrin is shown as formula II below.
Abelmoschus manihot (Hibiscus manihot L.) is Abelmoschus manihot, glutinous dry or Ulmus davidii bark, is a plant of Abelmoschus of the family annual herbaceous Malvaceae (Malvaceae), and Abelmoschus manihot has the reputation of the plant panda, contains various plant bioactive substances, and mainly contains flavonoid compounds, vitamin E, unsaturated fatty acids, dietary fibers, trace elements and the like (Chinese medicine evaluation, 2015, 32, 90-92). In recent years, golden flower sunflower has attracted attention as an important source for extracting flavonoids. Studies have shown that hyperin and isoquercitrin are the main active ingredients in the sunflower of golden flower, and the highest contents are 1.59% and 1.31%, respectively (2016, 39, 308 and 315, reported by Beijing university of traditional Chinese medicine).
There are many reports on the separation and purification of hyperoside and isoquercitrin. For example, Xiayanhai et al (Chinese patent application No. 201210424557.9) utilize three-stage series macroporous resin adsorption elution to simultaneously prepare hyperoside and isoquercitrin from folium Apocyni Veneti, with purity of 90% -98%. Pawangjie et al (Chinese patent application No. 201110091575.1) use macroporous resin adsorption and silica gel column chromatography to purify and separate hyperin from wintergreen, and the purity can reach 95%. The methods have the problems of complicated purification method, high cost, long production period, difficulty in industrial production and the like, and limit the application of the hyperin and isoquercitrin.
Based on the extractive solution of the abelmoschus manihot, the method removes other flavonoid compounds in the extractive solution of the abelmoschus manihot by utilizing the characteristics that the complexation capacity of the hyperin and isoquercitrin with zinc salt is weaker and the complexation capacity of other flavonoid compounds with zinc salt is stronger, and develops a method for quickly, efficiently and safely separating and purifying the hyperin and isoquercitrin from the abelmoschus manihot.
Disclosure of Invention
The invention aims to remove other flavonoid compounds in the abelmoschus manihot extract by utilizing the characteristics that the complexation capacity of hyperin and isoquercitrin with zinc salt is weak and the complexation capacity of other flavonoid compounds with zinc salt is strong, and develop a method for quickly, efficiently and safely separating and purifying the hyperin-isoquercitrin composition in the abelmoschus manihot.
The purpose of the invention is realized by the following technical scheme:
a method for quickly, efficiently and safely separating and purifying hyperin and isoquercitrin in Abelmoschus manihot is developed from Abelmoschus manihot extract by utilizing the difference of complexation capacity of flavonoids and zinc salt in Abelmoschus manihot. The method comprises the following steps:
A. precisely weighing 5.0g of dry crude powder of Abelmoschus manihot, heating and refluxing for extraction for 3h by using 70% ethanol solution at the temperature of 80 ℃, cooling to room temperature, carrying out suction filtration to obtain Abelmoschus manihot residues and supernatant, collecting the supernatant, and fixing the volume of the supernatant to a volumetric flask of 250mL by using 70% ethanol solution to obtain a sample solution;
B. weighing Abelmoschus manihot sample solution, adjusting pH to 8.5-12.5, preferably 10.5 with alkaline solution, wherein the alkaline solution can be selected from potassium hydroxide solution, sodium carbonate solution, ammonia water, etc., preferably potassium hydroxide solution. 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, preferably zinc sulfate, and the addition amount ensures that the mass ratio of the abelmoschus manihot sample to the zinc salt is 1/0.5-1/5, preferably 1/1. After the addition, the complexation reaction time is 1-12h, preferably 3-5 h. The temperature of the complexation reaction is 10-70 ℃, preferably 30-40 ℃, the zinc salt-flavone complex precipitate is removed by centrifugal separation, and the supernatant is collected;
C. heating and concentrating the supernatant to obtain high-purity hyperoside and isoquercitrin.
Analyzing the extractive solution of Abelmoschus manihot and separated and purified hyperoside and isoquercitrin by high performance liquid chromatography to obtain analysis result, and the chromatogram is shown in figure. The chromatographic conditions employed were: waters HPLC high performance liquid chromatograph, the chromatographic column is COSMOSIL C18(4.6mm multiplied by 200mm, 5 mu m), the mobile phase is 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), the flow rate is 1.0m L/min, the detection wavelength is 360nm, the sample introduction amount is 10 mu L, and the column temperature is room temperature.
The invention achieves the following beneficial results:
1. the golden flower sunflower extract is not required to be further processed, the zinc salt is directly added, the pH is adjusted to complex the zinc salt with other flavonoid substances except the hyperoside and the isoquercitrin in the extract, the hyperoside and the isoquercitrin in the golden flower sunflower can be simultaneously separated and purified, 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. the large-scale industrial production of separating and purifying the hyperoside and the isoquercitrin in the abelmoschus manihot is facilitated through the combined operation.
Drawings
FIG. 1 is an HPLC chromatogram of hyperin and isoquercitrin in an unpurified Abelmoschus manihot extract.
FIG. 2 is the HPLC chromatogram of hyperin and isoquercitrin in the purified Abelmoschus manihot extract.
The specific implementation mode is as follows:
the following further description of the method for separating and purifying hyperoside and isoquercitrin from Hibiscus manihot Linn according to the present invention is provided in conjunction with the accompanying drawings and specific examples to facilitate the understanding of the present invention by those skilled in the art, but the present invention is not limited thereto.
Example 1:
A. precisely weighing 5.0g of dry crude powder of Abelmoschus manihot, heating and refluxing for extraction for 3h by using 70% ethanol solution at the temperature of 80 ℃, cooling to room temperature, carrying out suction filtration to obtain Abelmoschus manihot residues and supernatant, collecting the supernatant, and fixing the volume of the supernatant to a volumetric flask of 250mL by using 70% ethanol solution to obtain a sample solution;
B. measuring 10mL of an Abelmoschus manihot sample solution, adjusting the pH value to 10.5 by using a potassium hydroxide solution, and 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 was 3 h. Carrying out centrifugal separation at the temperature of 30 ℃ to obtain supernatant and a zinc salt-flavone complex, and collecting the supernatant;
C. heating and concentrating the supernatant to obtain high-purity hyperoside and isoquercitrin, wherein the purities of hyperoside and isoquercitrin are 46.59% and 33.55%, respectively.
Example 2:
A. precisely weighing 5.0g of dry crude powder of Abelmoschus manihot, heating and refluxing for extraction for 3h by using 70% ethanol solution at the temperature of 80 ℃, cooling to room temperature, carrying out suction filtration to obtain Abelmoschus manihot residues and supernatant, collecting the supernatant, and fixing the volume of the supernatant to a volumetric flask of 250mL by using 70% ethanol solution to obtain a sample solution;
B. measuring 10mL of a Abelmoschus manihot sample solution, adjusting the pH value to 12.5 by using a sodium carbonate solution, and adding zinc chloride with a certain mass concentration, wherein the addition amount ensures that the mass ratio of the Abelmoschus manihot sample to the zinc chloride is 1/0.5. After the addition, the complexation reaction time was 12 h. The temperature of the complexation reaction is 40 ℃, centrifugal separation is carried out to obtain supernatant and zinc salt-flavone complex, and the supernatant is collected;
C. heating and concentrating the supernatant to obtain high-purity hyperoside and isoquercitrin, wherein the purities of hyperoside and isoquercitrin are 43.14% and 28.44%, respectively.
Example 3:
A. precisely weighing 5.0g of dry crude powder of Abelmoschus manihot, heating and refluxing for extraction for 3h by using 70% ethanol solution at the temperature of 80 ℃, cooling to room temperature, carrying out suction filtration to obtain Abelmoschus manihot residues and supernatant, collecting the supernatant, and fixing the volume of the supernatant to a volumetric flask of 250mL by using 70% ethanol solution to obtain a sample solution;
B. measuring 10mL of a Abelmoschus manihot sample solution, adjusting the pH value to 11.5 by using a sodium hydroxide solution, and adding zinc acetate with a certain mass concentration, wherein the addition amount ensures that the mass ratio of the Abelmoschus manihot sample to the zinc acetate is 1/5. After the addition, the complexation reaction time was 1 h. Carrying out centrifugal separation at the complexation temperature of 10 ℃ to obtain supernatant and a zinc salt-flavone complex, and collecting the supernatant;
C. heating and concentrating the supernatant to obtain high-purity hyperoside and isoquercitrin, wherein the purities of hyperoside and isoquercitrin are 42.97% and 28.24%, respectively.
Example 4:
A. precisely weighing 5.0g of dry crude powder of Abelmoschus manihot, heating and refluxing for extraction for 3h by using 70% ethanol solution at the temperature of 80 ℃, cooling to room temperature, carrying out suction filtration to obtain Abelmoschus manihot residues and supernatant, collecting the supernatant, and fixing the volume of the supernatant to a volumetric flask of 250mL by using 70% ethanol solution to obtain a sample solution;
B. measuring 10mL of an Abelmoschus manihot sample solution, adjusting the pH value to 10.5 by using ammonia water, adding zinc sulfate with a certain mass concentration, and ensuring that the mass ratio of the Abelmoschus manihot sample to the zinc sulfate is 1/0.5. After the addition, the complexation reaction time was 5 h. The temperature of the complex reaction is 70 ℃, and the time of the complex reaction is 1h after the complex reaction is added. Carrying out centrifugal separation at the complexation temperature of 10 ℃ to obtain supernatant and a zinc salt-flavone complex, and collecting the supernatant;
C. heating and concentrating the supernatant to obtain high-purity hyperoside and isoquercitrin, wherein the purities of hyperoside and isoquercitrin are 44.43% and 30.74%, respectively.
Example 5:
A. precisely weighing 5.0g of dry crude powder of Abelmoschus manihot, heating and refluxing for extraction for 3h by using 70% ethanol solution at the temperature of 80 ℃, cooling to room temperature, carrying out suction filtration to obtain Abelmoschus manihot residues and supernatant, collecting the supernatant, and fixing the volume of the supernatant to a volumetric flask of 250mL by using 70% ethanol solution to obtain a sample solution;
B. measuring 10mL of Abelmoschus manihot sample solution, adjusting the pH value to 10.5 by using potassium hydroxide, and 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 was 5 h. The temperature of the complexation reaction is 40 ℃, centrifugal separation is carried out to obtain supernatant and zinc salt-flavone complex, and the supernatant is collected;
C. heating and concentrating the supernatant to obtain high-purity hyperoside and isoquercitrin, wherein the purities of hyperoside and isoquercitrin are 44.07% and 28.39%, respectively.
Example 6:
A. precisely weighing 5.0g of dry crude powder of Abelmoschus manihot, heating and refluxing for extraction for 3h by using 70% ethanol solution at the temperature of 80 ℃, cooling to room temperature, carrying out suction filtration to obtain Abelmoschus manihot residues and supernatant, collecting the supernatant, and fixing the volume of the supernatant to a volumetric flask of 250mL by using 70% ethanol solution to obtain a sample solution;
B. measuring 10mL of an Abelmoschus manihot sample solution, adjusting the pH value to 8.5 by potassium hydroxide, and 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 was 7 h. The temperature of the complexation reaction is 50 ℃, centrifugal separation is carried out to obtain supernatant and zinc salt-flavone complex, and the supernatant is collected;
C. heating and concentrating the supernatant to obtain high-purity hyperoside and isoquercitrin, wherein the purities of hyperoside and isoquercitrin are 39.10% and 21.70%, respectively.
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 (7)
1. A method for separating and purifying hyperin and isoquercitrin from Abelmoschus manihot is characterized by comprising the following steps:
A. precisely weighing 5.0g of dry crude powder of Abelmoschus manihot, heating and refluxing for extraction for 3h by using 70% ethanol solution at the temperature of 80 ℃, cooling to room temperature, carrying out suction filtration to obtain Abelmoschus manihot residues and supernatant, collecting the supernatant, and fixing the volume of the supernatant to a volumetric flask of 250mL by using 70% ethanol solution to obtain a sample solution;
B. weighing an abelmoschus manihot sample solution, adjusting the pH value to 10.5-12.5 by using an alkaline solution, adding zinc salts into the alkaline solution, namely a potassium hydroxide solution, a sodium carbonate solution and ammonia water, wherein the zinc salts are zinc sulfate, zinc acetate and zinc chloride, the addition amount ensures that the mass ratio of the abelmoschus manihot sample to the zinc salts is 1/0.5-1/5, after the addition, the complexing reaction time is 1-12h, the complexing reaction temperature is 10-70 ℃, performing centrifugal separation to remove zinc salt-flavone complex precipitate, and collecting supernatant;
C. heating and concentrating the supernatant to obtain high-purity hyperoside and isoquercitrin.
2. The method of claim 1, wherein the method comprises the steps of: the alkaline solution is potassium hydroxide solution.
3. The method of claim 1, wherein the method comprises the steps of: the pH was adjusted to 10.5.
4. The method of claim 1, wherein the method comprises the steps of: the zinc salt used in the complexing reaction is zinc sulfate.
5. The method of claim 1, wherein the method comprises the steps of: the mass ratio of the mallow sample to the zinc salt in the complexation reaction is 1/1.
6. The method of claim 1, wherein the method comprises the steps of: the complex reaction time is 3-5 h.
7. The method of claim 1, wherein the method comprises the steps of: the temperature of the complexation reaction is 30-40 ℃.
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| CN108864226B (en) * | 2018-08-09 | 2021-05-07 | 湖南农业大学 | Method for extracting ardisiacrispin and quercitrin from Japanese ardisia |
| CN109810116B (en) * | 2019-02-26 | 2021-06-04 | 北京理工大学 | Method for purifying ellagic acid in chestnut shell extracting solution |
| CN110590882B (en) * | 2019-09-16 | 2020-11-03 | 北京理工大学 | Method for simultaneously separating and purifying 6 flavone compounds from sunflower seeds |
| CN115669470A (en) * | 2020-12-11 | 2023-02-03 | 北京林业大学 | Application of AemYB30 and/or AeUF3GaT1 in improving seting rate of Abelmoschus manihot |
| CN117442534B (en) * | 2023-12-14 | 2024-05-28 | 广州嘉瑜生物科技有限公司 | Abelmoschus manihot extract, preparation method thereof and application thereof in preparing skin care product |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103018371A (en) * | 2012-12-24 | 2013-04-03 | 江苏苏中药业集团股份有限公司 | Quality control method of sunset abelmoschus root medicinal material as well as extract and preparation of sunset abelmoschus root |
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103018371A (en) * | 2012-12-24 | 2013-04-03 | 江苏苏中药业集团股份有限公司 | Quality control method of sunset abelmoschus root medicinal material as well as extract and preparation of sunset abelmoschus root |
Non-Patent Citations (6)
| Title |
|---|
| Purification of flavonoid fromGingko bilobaextract by zinc complexation method and its effect on antioxidant activity;Jing Zhang，等;《Separation and Purification Technology》;20101231;第71卷;第273–278页 * |
| Zn–polyphenol chelation: complexes with quercetin,(+)-catechin, and derivatives: I optical and NMR studies;G. Le Nest，等;《Inorganica Chimica Acta》;20041231;第357卷;第775-784页 * |
| 中药黄蜀葵花化学成分的分离与鉴定(Ⅱ);李春梅，等;《沈阳药科大学学报》;20101031;第27卷(第10期);第803-807页 * |
| 基于药物体系的金花葵特征图谱质量表征关联分析研究;冯朵，等;《北京中医药大学学报》;20160430;第39卷(第4期);第308-315页 * |
| 金属络合法纯化鼠曲草类黄酮工艺;林华婷，等;《中国食品学报》;20170430;第17卷(第4期);第116-122页 * |
| 黄蜀葵化学成分与药理活性研究进展;温锐，等;《中国野生植物资源》;20150430;第34卷(第2期);第37-44页 * |
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