CN107626220B - Method for promoting dissolution of flavone or glycoside compounds and application thereof - Google Patents

Method for promoting dissolution of flavone or glycoside compounds and application thereof Download PDF

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CN107626220B
CN107626220B CN201610567701.2A CN201610567701A CN107626220B CN 107626220 B CN107626220 B CN 107626220B CN 201610567701 A CN201610567701 A CN 201610567701A CN 107626220 B CN107626220 B CN 107626220B
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baicalin
sodium phytate
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phytate
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丁观军
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Abstract

The invention discloses and discloses the property that phytic acid can promote the dissolution aid of baicalin of glycoside compounds in an aqueous solvent or an aqueous mixed solution. By utilizing the property of helping dissolution, the extraction rate of the baicalin in the traditional method, the detection safety and the antibacterial effect in the aspects of daily chemicals and medicines can be effectively improved.

Description

Method for promoting dissolution of flavone or glycoside compounds and application thereof
Technical Field
The invention belongs to the technical field of medicines and daily chemicals, and particularly relates to a method for promoting flavone or glycoside compounds to be dissolved in an aqueous solvent or an aqueous mixed solution and application thereof.
Background
Some traditional Chinese medicine flavone or glycoside compounds have at least two benzene rings and one carboxyl group, are insoluble in formic acid, acetic acid and acetone, are hardly soluble in solvents such as water, ether, benzene, chloroform and the like, and are soluble in alkaline aqueous solution. The physicochemical properties of the traditional Chinese medicine lead the extraction and the application of the traditional Chinese medicine to be limited.
Baicalin (Baicalin) is taken as an example. Baicalin is a flavonoid compound extracted and separated from radix Scutellariae, has remarkable bioactivity, has antibacterial, diuretic, antiinflammatory, antiallergic and spasmolytic effects, and has strong physiological effects such as anticancer effect. Has already occupied an important position in clinical medicine. Baicalin can absorb ultraviolet rays, remove oxygen free radicals and inhibit the generation of melanin, so that the baicalin can be used for medicines and cosmetics and is a good raw material for functional cosmetic. The functional indications are as follows: purging excessive fire, removing damp-heat, stopping bleeding, preventing abortion. It is used to treat high fever, polydipsia, cough due to lung heat, dysentery due to damp-heat, jaundice, stranguria due to heat, emesis, epistaxis, metrorrhagia, metrostaxis, conjunctival congestion, swelling and pain, threatened abortion, carbuncle, swelling, and furuncle. The pharmacological action is as follows: 1. anti-inflammatory and anti-allergic reactions: the product has effect in relieving allergic contraction of guinea pig in vitro trachea and allergic asthma of whole animal, and has synergistic effect with ephedrine; 2. And (3) antibiosis: is one of the antibacterial components of the scutellaria; 3. and (3) diuresis: has diuretic effect on rabbit; 4. cholagogic: 5. Clearing heat; 6. reducing the pressure; 7. sedation; 8. other agents which reduce the levels of total cholesterol, free cholesterol and triglycerides in the liver of experimental rats; 9. clinically: the Chinese medicament is mainly used for treating hepatitis in China, and has obvious curative effects on acute icteric hepatitis, acute anicteric hepatitis and chronic hepatitis.
In physical and chemical properties, baicalin is a light yellow needle-shaped crystal, has a melting point of 223-. The baicalin can be extracted by decocting in water, warm soaking in alkali, extracting with alcohol, and microwave/ultrasonic extracting. The traditional water decoction method has long time and low efficiency; baicalin is easily damaged in the alkaline environment of the alkali warm leaching method; the alcohol extraction method adopts an organic solvent; the microwave/ultrasonic extraction method requires a precise instrument, and the space in which the method can be actually processed is also limited. The research in the literature finds that: the extraction rate of the baicalin is about 1-10% of that of the radix scutellariae. The physicochemical properties of baicalin limit its practical application and in the process of extracting baicalin from radix Scutellariae.
Disclosure of Invention
In order to solve the problems in the prior art, a method for promoting the dissolution of flavone or glycoside compounds in an aqueous solvent or an aqueous mixed solution is found. The flavone or glycoside compound has at least two benzene rings and one carboxyl group, is insoluble in formic acid, acetic acid and acetone, is hardly soluble in water, ether, benzene, chloroform and other solvents, and is soluble in alkaline aqueous solution. The method is characterized in that the cosolvent used is phytic acid or a phytate metal salt, the mass ratio of the phytate metal salt to the flavone or glycoside compound is in the range of 1/5 to 10/1, and the pH of the solution is in the range of 3.0 to 7.0. Phytic acid is otherwise known as phytic acid.
The method is characterized in that the metal phytate is sodium phytate, and the flavone or glycoside compound is baicalin.
The method is characterized in that the mass ratio of the sodium phytate to the baicalin is 1/2.
The process for extracting baicalin is obtained by utilizing the characteristic that phytic acid or sodium phytate can promote the dissolution of baicalin in an aqueous solution or an aqueous mixed solution with the pH value of 3.0 to 7.0 and the precipitation of baicalin in an acidic solution with the pH value of 1.0 to 2.0: processing radix Scutellariae into coarse powder or granule, adding 0.5-10 times of water or ethanol water solution, and heating to 10 deg.C or at room temperatureoC to 100oAnd C, adding sodium phytate with the mass equal to 1-10% of that of the radix scutellariae, keeping the pH value of the aqueous solution between 3.0 and 7.0, and extracting for 1-24 hours. Can be extracted for one time or multiple times. Mixing the single or multiple filtrates, and adjusting pH to 1-2 by adding acid to 10oC~90oAnd C, preserving heat, standing for 3-24 hours, and filtering, washing, drying and the like to obtain baicalin coarse powder.
The process for extracting baicalin is characterized in that the mass of the added sodium phytate is half of the mass of the obtained baicalin.
Before detecting and analyzing the content of the baicalin in the food beverage, the toothpaste or the cosmetics by using an ultraviolet visible light absorption photometer or a high performance liquid chromatography, the method is adopted to help extract the baicalin extracting solution in the product.
The oral care product prepared by the method of using the phytic acid or the sodium phytate to assist in dissolving the baicalin is characterized in that the mass ratio of the baicalin to the sodium phytate is 2: 1.
The oral care product can inhibit acid production of lactobacillus bulgaricus, lactobacillus thermophilus and lactobacillus acidophilus in oral cavity, and is characterized in that the concentration of baicalin is 10.0mg/45mL, the concentration of sodium phytate is 5.0mg/45mL, and the pH value of the product is between 4.0 and 7.0.
The application of the method of assisting in dissolving baicalin by phytic acid or sodium phytate in the field of preparing nutritional health products, cosmetics or medical products.
Compared with the prior art, the technical scheme of the invention has the following advantages
1. The invention discloses a technical scheme for assisting in dissolving flavone or glycoside compounds, in particular baicalin, by adopting sodium phytate or phytic acid in an acidic water environment.
2 in extracting baicalin from the root of scutellaria baicalensis, the baicalin can be extracted quickly or under low temperature environment by utilizing the solubilizing characteristics of sodium phytate or phytic acid.
3 in the process of detecting the baicalin by adopting an ultraviolet visible light method or high performance liquid chromatography, organic solvent is avoided, and sodium phytate or phytic acid aqueous solution can be directly used for extracting the baicalin.
4, the sodium phytate and the baicalin can act synergistically in the aspect of bacteriostasis and acid production.
5 the baicalin can be directly changed into a molecular state by utilizing the solubilizing characteristic of sodium phytate or phytic acid, and is applied to the food or medicine field.
Drawings
FIG. 1a photograph: NaH2PO4*2H2O (0.64 wt%) water solution, wherein the concentration of baicalin and sodium phytate in the solution is 0.00040g/10 mL;
FIG. 1b photograph: NaH2PO4*2H2O (0.64 wt%) water solution, wherein the concentration of baicalin and sodium phytate in the water solution is 0.0010 g/10 mL;
FIG. 1c photograph: NaH2PO4*2H2O (0.64 wt%) water solution, wherein the concentration of baicalin and sodium phytate in the water solution is 0.0040g/10 mL;
FIG. 1d photograph: NaH2PO4*2H2O (0.64 wt%)The concentration of the baicalin and the sodium phytate in the aqueous solution is 0.0100 g/10 mL;
FIG. 1e photograph: NaH2PO4*2H2O (0.64 wt%) water solution, wherein the concentration of baicalin and sodium phytate in the water solution is 0.0200g/10 mL;
FIG. 1f photograph: NaH2PO4*2H2O (0.64 wt%) water solution, wherein the concentration of baicalin and sodium phytate in the water solution is 0.0500 g/10 mL;
FIG. 1g photograph: NaH2PO4*2H2O (0.64 wt%) water solution, wherein the concentration of baicalin and sodium phytate in the water solution is 0.010 g/10 mL;
FIG. 1h photograph: NaH2PO4*2H2O (0.64 wt%) water solution, wherein the concentration of baicalin and sodium phytate in the water solution is 0.020g/10 mL;
FIG. 1i photograph: NaH2PO4*2H2O (0.64 wt%) aqueous suspension, baicalin concentration in the suspension was 0.100g/10 mL.
FIG. 2a photograph: NaH2PO4*2H2O (0.64 wt%) water solution, wherein the concentration of baicalin in the solution is 0.020g/10mL, and the concentration of sodium phytate is 0.0020 g/10 mL;
FIG. 2b photograph: NaH2PO4*2H2O (0.64 wt%) water solution, wherein the concentration of baicalin in the solution is 0.020g/10mL, and the concentration of sodium phytate is 0.0040g/10 mL;
FIG. 2c photograph: NaH2PO4*2H2O (0.64 wt%) water solution, wherein the concentration of baicalin in the solution is 0.020g/10mL, and the concentration of sodium phytate is 0.010 g/10 mL;
FIG. 2d photograph: NaH2PO4*2H2O (0.64 wt%) water solution, wherein the concentration of baicalin in the solution is 0.020g/10mL, and the concentration of sodium phytate is 0.020g/10 mL;
FIG. 2e photograph: NaH2PO4*2H2O (0.40 wt%) water solution, wherein the concentration of baicalin in the solution is 0.020g/10mL, and the concentration of sodium phytate is 0.020g/10 mL.
Detailed Description
The present invention will be described in further detail with reference to specific examples, and specific embodiments will be given below.
The characteristics of sodium phytate helping to dissolve baicalin in water were studied. Dissolution, in a broad sense, is a process in which more than two substances are mixed to form a homogeneous phase in a molecular state. And dissolution in the narrow sense refers to a process in which a liquid chemically reacts with a solid/liquid/or gas to make it into a homogeneous phase in a molecular state. In FIGS. 1a-h, NaH containing different baicalins and sodium phytate2PO4*2H2The pH of the O (0.64 wt%) aqueous solution is in the range of 4.0 +/-0.5; in the experiment, it is found that when the mass ratio of the sodium phytate to the baicalin is 1:1 and the mass of the baicalin is from 0.00040g/10 mL to 0.200g/10mL, an aqueous baicalin solution (shown in figures 1a, b, c, d, e, f, g and h) is obtained, the aqueous baicalin solution is not a baicalin suspension, and the yellow color is thicker along with the concentration. When only baicalin (0.100 g/10 mL) was in the solution system, a baicalin suspension was obtained (FIG. 1 i). FIG. 2(a-d) shows NaH containing 0.0200g/10mL baicalin and varying amounts of sodium phytate2PO4*2H2O (0.64 wt%) suspension or aqueous solution (pH range 4.0. + -. 0.5). It was found in the experiment that when the mass ratio of sodium phytate to baicalin was 1/10, a baicalin suspension appeared (fig. 2 a); when the mass ratio is changed from 1/5 to 1/2 or 1/1, the baicalin suspension (fig. 2 b) slowly becomes an aqueous baicalin solution (fig. 2c, fig. 2 d). When 0.40 wt% phosphoric acid solvent was used in place of 0.64 wt% NaH2PO4*2H2O aqueous solution, the pH became about 1.5, and a suspension of 0.020g/10mL baicalin and 0.020g/10mL sodium phytate in phosphoric acid (0.40 wt%) was obtained (FIG. 2 e). Therefore, when the concentration of baicalin is 0.0200g/10mL and the pH is about 4, the concentration of sodium phytate required for completely dissolving baicalin is more than 0.0040g/10 mL. Under the same conditions, when the pH value becomes about 1.5, the baicalin solution becomes a suspension, and after standing for 8 hours, the baicalin particles can be separated by sedimentation, as shown in figure 2 e.
Extraction of baicalin from Chinese medicine
The characteristics that the phytic acid or the sodium phytate promotes the dissolution of the baicalin in the aqueous solution with the pH value of 3.0-7.0 and the precipitation of the baicalin in the acidic solution (with the pH value of 1.0-2.0) are utilized. Extraction processComprises the following steps: processing radix Scutellariae into coarse powder or granule, adding 0.5-10 times of water or ethanol water solution, and heating to 10 deg.C or at room temperatureoC to 100oAnd C, adding sodium phytate with the mass equal to 1-10% of that of the radix scutellariae, keeping the pH value of the aqueous solution between 3.0 and 7.0, and extracting for 1-24 hours. Can be extracted for one time or multiple times. Mixing the single or multiple filtrates, and adjusting pH to 1-2 by adding acid to 10oC~90oAnd C, preserving heat, standing for 3-24 hours, and filtering, washing, drying and the like to obtain baicalin coarse powder. The process for extracting baicalin is characterized in that the mass of the added sodium phytate is half of the mass of the obtained baicalin.
Analyzing and detecting baicalin product
In the analysis and detection of the baicalin content in food, beverage, toothpaste and cosmetics, the traditional method adopts an alcohol-water solution and ultrasonic treatment or heating treatment to extract the baicalin component in the food, beverage, toothpaste and cosmetics, and the subsequent steps adopt an ultraviolet visible light absorption photometer or high performance liquid chromatography for characterization and analysis of the baicalin concentration. There are some disadvantages here: in the using process of the alcohol solvent, the volatilization of the alcohol brings negative effects to the environment and experimenters, and meanwhile, the use of the alcohol may also need an additional waste treatment process; prolonged (30 min) sonication or heat treatment may destroy baicalin; the traditional method has certain difficulty in extracting a sample with high concentration of baicalin (> 2%), and cannot extract the baicalin at high efficiency at one time. In the invention, for a sample containing baicalin, the quality of the baicalin is estimated, 1.000g of the sample is taken, a sodium phytate aqueous solution is added, and the pH value of the solution is adjusted to be within the range of 4-6. Wherein the mass of sodium phytate is at least 20%, preferably 50% or 100% of the mass of baicalin. In phytic acid or sodium phytate aqueous solution, the concentration of baicalin is within the range of 2 mu g/mL-30 mu g/mL, and the absorbance of ultraviolet visible light can form a linear relation. Embodiment 1: for low concentration baicalin (< 1%) samples, sample 1.000g into a 50mL graduated centrifuge tube, add 10mL of 0.5% sodium phytate aqueous solution (the pH of the sodium phytate aqueous solution is adjusted to 5.0 with 1M NaH2PO4 x 2H2O or HCl aqueous solution), vortex and shake for 1min, then ultrasonic treatment for 1min, stand for 5min, high speed centrifugation for 10 min, take the supernatant and filter with a filter membrane, and measure under the conditions of ultraviolet visible light photometer or high performance liquid chromatograph. Embodiment 2: for a medium concentration baicalin (1% < mass ratio < 10%) sample, 1.000g of the sample is put into a 50mL graduated centrifuge tube, 10mL of 5% sodium phytate aqueous solution is added (the pH value of the sodium phytate aqueous solution is adjusted to 5.0 by 1M NaH2PO4 x 2H2O or HCl aqueous solution), vortex and oscillation is carried out for 1min, then ultrasonic treatment is carried out for 1min, standing is carried out for 5min, high-speed centrifugation is carried out for 10 min, and supernatant is filtered by a filter membrane and is measured under the conditions of an ultraviolet visible light photometer or a high performance liquid chromatograph.
Eye drop
Baicalin eye drops with different concentrations: eye drop containing 1% baicalin and 0.5% phytic acid or sodium phytate; eye drop containing 3% baicalin and 1.5% phytic acid or sodium phytate; eye drop containing 5% baicalin and 1.5% phytic acid or sodium phytate; eye drop containing 5% baicalin and 2.5% phytic acid or sodium phytate; an eye drop contains baicalin 5% and phytic acid or sodium phytate 5%.
Intravenous injection
Baicalin injection with different concentrations: an injection containing 0.1% baicalin and 0.05% phytic acid or sodium phytate; an injection containing 0.3% of baicalin and 0.15% of phytic acid or sodium phytate; an injection containing 1% baicalin and 0.5% phytic acid or sodium phytate; an injection containing 3% of baicalin and 2% of phytic acid or sodium phytate; an injection containing 5% baicalin and 3% phytic acid or sodium phytate.
Cosmetic preparation:
cosmetics such as emulsion, cream, spray liquid and the like containing 0.01-5% of baicalin and 0.05-5% of phytic acid or sodium phytate; the baicalin is changed into a solution state, namely a molecular state or a molecular cluster state, so that the baicalin can penetrate into the epidermis and the dermis of the skin more, the ultraviolet rays can be absorbed better, the free radicals can be eliminated, the generation of melanin can be inhibited, and the repairing function can be helped.
Washing product
Perfumed soap, bath foam, shampoo and other products containing 0.01-5% of baicalin and 0.05-5% of phytic acid or sodium phytate. The baicalin is converted into solution state, i.e. molecular state or molecular cluster state, and is helpful for the baicalin to penetrate into epidermis and dermis of skin more, so as to absorb ultraviolet rays, remove free radicals, inhibit melanin generation and achieve antibacterial effect
Oral care products
The inhibitory effect of the sodium phytate and baicalin complex on acid production of oral bacteria is studied. Experimental materials: yogurt powder (containing Lactobacillus bulgaricus, Streptococcus thermophilus and Lactobacillus acidophilus) is commercially available. The simulated oral saliva laboratory preparation comprises the following specific components: 137.35 mM NaCl, 4.17 mM NaHCO3、3.01 mM KCl、7.17 mM K2HPO43H2O、1.53 mM MgCl26H2O、20.00 mM HCl、0.90 mM CaCl2、0.51 mM Na2SO4And Tris adjusted to pH 7.0. Before the experiment, the used experimental ware and the simulated oral saliva are sterilized for 2 hours under an ultraviolet lamp. The experimental treatment is carried out on a 100-stage purification workbench, and specifically comprises the following steps: sodium phytate and baicalin shown in Table 1 were put into a plastic bottle having a capacity of 48mL, then 1.0 g of yogurt powder and 45mL of simulated oral saliva were both put into the bottle, mixed uniformly with a glass rod, the pH value was measured (6.8. + -. 0.3), and finally stored in a sealed state until 37 g was obtainedoAnd C, placing in an incubator for 24 h. At the end of the experiment, the pH of all samples was measured with a pH meter.
In table 1, it can be found that the simulated oral saliva pH becomes 3.70 when used without bacteriostatic agents; the baicalin, the sodium phytate, the baicalin and the sodium phytate can effectively inhibit the acid production of lactobacillus including lactobacillus acidophilus by the matching of the baicalin, the sodium phytate and the baicalin in with the mass ratio of 2: 1; with the increase of the concentration of the bacteriostatic agent, the bacteriostatic acid-producing effect is gradually enhanced, and the mutual matching of baicalin and sodium phytate in a mass ratio of 2:1 is found to show a stronger inhibitory effect. Especially, the blending effect of 10.0mg of baicalin and 5.0mg of sodium phytate is better than that of the single use of 50.0 mg of baicalin or 25.0 mg of sodium phytate. This also shows that the bacteriostatic acid-producing effect of baicalin in the solution state is better than that of baicalin in the granule state. An oral care product capable of inhibiting acid production in oral cavity by lactobacillus bulgaricus, lactobacillus thermophilus and lactobacillus acidophilus is characterized in that the concentration of baicalin is 10.0mg/45mL, the concentration of sodium phytate is 5.0mg/45mL, and the pH value of the product is between 4.0 and 7.0.
TABLE 1.45 pH of simulated oral saliva containing different antibacterial ingredients and 1.00g of yogurt powder after 24 hours treatment
Figure 553472DEST_PATH_IMAGE001
It should be understood that the above examples are only for clarity of illustration and are not intended to limit the embodiments. Other variations and modifications will be apparent to persons skilled in the art in light of the above description. And are neither required nor exhaustive of all embodiments. And obvious variations or modifications of the invention may be made without departing from the scope of the invention.

Claims (6)

1. A method for promoting the dissolution of flavone or glycoside compounds in an aqueous solvent or aqueous mixed solution, characterized in that the cosolvent used is a phytate metal salt, and the mass ratio of the phytate metal salt to the flavone or glycoside compounds is in the range of 1/5 to 10/1, and the pH of the solution is in the range of 3.0 to 7.0; the flavone or glycoside compound is baicalin; the concentration of baicalin is greater than or equal to 10.0mg/45 mL.
2. A process according to claim 1, wherein the metal salt of phytate is sodium phytate and the flavone or glycoside compound is baicalin.
3. A process according to claim 2, wherein the mass ratio of sodium phytate to baicalin is in the range of 1/5 to 1/1, and the concentration of baicalin is 10.0mg/45mL to 0.200g/10 mL.
4. A process according to claim 3, wherein the mass ratio of sodium phytate to baicalin is 1/2, and the concentration of baicalin is 0.020g/10mL to 0.100g/10 mL.
5. An oral care product made by the process of claim 1, characterized in that the mass ratio of baicalin to sodium phytate is 2: 1; a pH in the range of 3.0 to 7.0; the concentration of baicalin is greater than or equal to 10.0mg/45 mL.
6. The oral care product of claim 5, which inhibits acid production in the oral cavity by Lactobacillus bulgaricus, Lactobacillus thermophilus and Lactobacillus acidophilus, wherein the baicalin concentration is 10.0mg/45mL, the sodium phytate concentration is 5.0mg/45mL, and the pH of the product is between 4.0 and 7.0.
CN201610567701.2A 2016-07-19 2016-07-19 Method for promoting dissolution of flavone or glycoside compounds and application thereof Expired - Fee Related CN107626220B (en)

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CN102764304A (en) * 2012-08-15 2012-11-07 泸州品创科技有限公司 Method for improving non-oxidation rate of flavonoids in lotus leaves
CN102885863A (en) * 2012-11-01 2013-01-23 上海中医药大学 Flavone hippophae composition and application of composition
CN103145782A (en) * 2013-01-14 2013-06-12 李玉山 Novel extracting process of high-purity baicalin
CN103648471A (en) * 2011-07-12 2014-03-19 宝洁公司 Oral care compositions comprising phytic acid
CN104513285A (en) * 2013-10-08 2015-04-15 杜淑卿 Baicalin extracting technology process
CN105669801A (en) * 2016-03-04 2016-06-15 霍应怀 Extraction technology for baicalin crude product

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6020471A (en) * 1996-09-13 2000-02-01 Abbott Laboratories Process for isolating phytoestrogens from plant protein
CN103648471A (en) * 2011-07-12 2014-03-19 宝洁公司 Oral care compositions comprising phytic acid
CN102764304A (en) * 2012-08-15 2012-11-07 泸州品创科技有限公司 Method for improving non-oxidation rate of flavonoids in lotus leaves
CN102885863A (en) * 2012-11-01 2013-01-23 上海中医药大学 Flavone hippophae composition and application of composition
CN103145782A (en) * 2013-01-14 2013-06-12 李玉山 Novel extracting process of high-purity baicalin
CN104513285A (en) * 2013-10-08 2015-04-15 杜淑卿 Baicalin extracting technology process
CN105669801A (en) * 2016-03-04 2016-06-15 霍应怀 Extraction technology for baicalin crude product

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