CN114317630A - Preparation method of diosmetin - Google Patents

Preparation method of diosmetin Download PDF

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CN114317630A
CN114317630A CN202111255615.5A CN202111255615A CN114317630A CN 114317630 A CN114317630 A CN 114317630A CN 202111255615 A CN202111255615 A CN 202111255615A CN 114317630 A CN114317630 A CN 114317630A
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diosmin
enzymolysis
enzyme
mixing
filtering
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赵卓君
杨帆
张远林
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Chengdu Okay Pharmaceutical Co ltd
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Abstract

The invention discloses a preparation method of diosmetin, which comprises the following steps: diosmin is subjected to enzymolysis by using enzyme; the weight ratio of the diosmin to the enzyme is 100 (0.60-23.81); the preparation method does not produce a large amount of waste water, does not pollute the environment, is easy to control reaction conditions, simple to operate, convenient to treat and high in yield, and the prepared diosmetin has high HPLC content, high purity and good product quality.

Description

Preparation method of diosmetin
Technical Field
The invention relates to the technical field of synthesis, and particularly relates to a preparation method of diosmetin.
Background
Diosmetin is one of natural flavonoids, and has a chemical name of 3 ', 5, 7-trihydroxy-4' -methoxyflavone. The diosmetin is yellow powder, has a melting point of 256-258 ℃, a CAS number of 520-34-3, a molecular formula of C16H12O6, a molecular weight of 300.26, and can be dissolved in organic solvents such as methanol, ethanol and the like. The hydroxyl groups at three positions of 3', 5 and 7 and the C2 ═ C3 double bond in the structural formula determine the unique chemical properties and biological activities of diosmetin, wherein the phenolic hydroxyl group at the position 7 can be combined with different glycosyl groups to generate glycosylation reaction to show different biological activities. Diosmetin is widely distributed in nature, mainly exists in a free type or a glucoside type, and is mainly found in natural medicines such as chrysanthemum, spearmint, valeriana jatamansi jones and fruits such as lemon, peanut and the like at present. The flavonoids are important components of daily diet of people, the chemoprevention effect of the flavonoids in diet on cancer is a hot point of study of researchers in recent years, and diosmetin has the effects of oxidation resistance, infection resistance, shock resistance and the like, can be widely applied to functional foods, cosmetics and medicines, and therefore has received wide attention.
The content of diosmetin in natural plants is low, so that a synthesis method is mostly adopted to prepare diosmetin to meet market demands, and the existing diosmetin synthesis process adopts organic solvents and inorganic acids as hydrolysis media, so that a large amount of acidic wastewater is generated, and environmental pollution is easily caused.
Disclosure of Invention
In view of the above, the application provides a method for preparing diosmin, which prepares diosmin by enzymolysis, and does not generate a large amount of wastewater in the production process, and does not cause environmental pollution, the reaction conditions are easy to control, the operation is simple, the treatment is convenient, the yield is high, the prepared diosmin has high HPLC content, the HPLC content reaches more than 98%, the purity is high, and the product quality reaches 99%.
In order to solve the technical problems, the technical scheme provided by the application is a preparation method of diosmetin, which comprises the following steps: diosmin is subjected to enzymolysis by using enzyme; the weight ratio of diosmin to enzyme is 100 (0.60-23.81).
Preferably, the preparation method specifically comprises: mixing diosmin, enzyme and water for enzymolysis; the weight ratio of the diosmin to the enzyme is 100 (0.60-23.81); the ratio of diosmin to water was 105 kg: 1m3
Preferably, the enzyme is selected from one or more of hesperidinase, rhamnosidase, naringinase, glucosidase and pectinase.
Preferably, the ratio of diosmin to enzyme by weight is 100: 2.38.
Preferably, the enzyme is hesperidinase.
Preferably, the enzymolysis temperature is 35-70 ℃, and the enzymolysis time is 12-72 h.
Preferably, the enzymolysis temperature is 40-50 ℃.
Preferably, the enzymatic hydrolysis temperature is 50 ℃.
Preferably, the enzymolysis time is 24 h.
Preferably, the preparation method further comprises: mixing the reaction solvent, hesperidin, alkaline reagent and iodine, and heating for reaction to obtain diosmin.
Preferably, the preparation method further comprises:
(A1) mixing iodine and a reaction solvent to obtain a raw material solution I;
(A2) mixing hesperidin with a reaction solvent to obtain a raw material solution II;
(A3) mixing the raw material solution I and the raw material solution II, heating for reaction, recovering a reaction solvent, adding water, uniformly mixing, filtering, washing with water, and collecting a filter cake;
(A4) mixing and dissolving the filter cake and an alkaline solution, and filtering by using a fine filter to obtain a fine-filtered filtrate;
(A5) and mixing the fine filtered filtrate with hydrochloric acid, crystallizing, filtering, and collecting a filter cake to obtain diosmin.
Preferably, the weight ratio of the hesperidin to the enzyme is 100 (0.5-20).
Preferably, the hesperidin to enzyme weight ratio is 100:2.
Preferably, the weight ratio of iodine to hesperidin is 1: 5 to 15.
Preferably, the weight ratio of iodine to hesperidin is 3: 10.
preferably, the ratio of the reaction solvent to the iodine used in the step (A1) is 1m3:75kg
Preferably, the ratio of the reaction solvent to the hesperidin used in the step (A2) is 1m3:200~300kg。
Preferably, the ratio of the reaction solvent to the hesperidin used in the step (A2) is 1m3:250kg。
Preferably, the step (a3) specifically includes: adding the raw material solution I into the raw material solution II at the flow rate of 400ml/min, heating for reaction, recovering a reaction solvent, adding water, uniformly mixing, filtering, washing with water, and collecting a filter cake.
Preferably, the step (a3) specifically includes: heating the raw material solution II to 70 ℃, adding the raw material solution I into the raw material solution II at the flow rate of 400ml/min, heating to 85 ℃, stirring, reacting for 18h, recovering a reaction solvent, adding water at the temperature of 40-50 ℃, stirring, filtering, washing with water until the pH value of an effluent liquid is 6-7, and collecting a filter cake.
Preferably, hydrochloric acid is added into the filtrate subjected to the fine filtration in the step (A5) to adjust the pH value to 5-6.
Preferably, the reaction solvent is a pyridine or amide solvent.
Preferably, the amide solvent is selected from any one of methylacetamide, ethylacetamide, dimethyloxamide, dimethylacetamide, or dimethylformamide.
Preferably, the amide solvent is N, N dimethylformamide.
Preferably, the reaction solvent is an amide solvent.
Preferably, the alkaline agent is an inorganic alkaline agent.
Preferably, the alkaline agent is selected from one or more of sodium hydroxide, potassium hydroxide, sodium carbonate, sodium bicarbonate and potassium carbonate solution.
Preferably, the alkaline agent is sodium hydroxide.
Preferably, the preparation method further comprises: extracting with ethanol after enzymolysis.
Preferably, the ethanol is 95% ethanol.
Preferably, the preparation method further comprises: filtering after enzymolysis treatment (I), refluxing and extracting by ethanol, filtering (II), collecting filtrate, crystallizing, standing, filtering (III), washing, collecting filter cake, drying and crushing.
Preferably, the filtration (I) is plate and frame filtration.
Preferably, the ethanol extraction process is ethanol reflux extraction.
Preferably, the ethanol extraction process is reflux extraction with 95% ethanol.
Preferably, the reflux extraction process has a reflux extraction time of 2 h.
Preferably, the crystallization process is specifically: adding cooling water, standing and crystallizing.
Preferably, the washing process is specifically: washing with water until no alcohol smell.
Preferably, the preparation method specifically comprises: filtering with plate-frame filter after enzymolysis, reflux extracting with ethanol, filtering (II), collecting filtrate, adding cooling water, standing for crystallization, filtering (III), washing with water until no alcohol smell exists, collecting filter cake, oven drying, and pulverizing.
The detailed description of the present application compared to the prior art is as follows
The application provides a method for preparing diosmin, which is used for preparing diosmin by enzymolysis, wherein the principle of diosmin enzymolysis is that rhamnose and glucose of diosmin are removed under the action of hesperidinase.
Figure RE-GDA0003519645420000041
The preparation method of diosmetin does not generate a large amount of waste water and does not cause pollution to the environment.
The preparation method of diosmetin has the advantages of short time, simple post-treatment, low production cost and high yield, and the prepared diosmetin has high HPLC content, high purity and good product quality and is suitable for industrial production.
The invention screens the proper dosage of the hesperidinase, the optimal dosage is that the hesperidinase with 2 percent of the weight of the hesperidin (2.38 percent of the weight of the diosmin) is used for enzymolysis, the lower limit is 0.5 percent of the weight of the hesperidin (0.60 percent of the weight of the diosmin), and the upper limit is 20 percent of the weight of the hesperidin (23.81 percent of the weight of the diosmin). More than 20% by weight of hesperidin (23.81% by weight of diosmin) causes enzyme waste and increases production cost. When the amount of hesperidinase is small, the diosmin does not react completely.
The optimal enzymolysis temperature is 50 ℃, and the optimal enzymolysis time is 24 hours. The method has the advantages of easily controlled reaction conditions, simple operation and convenient treatment.
Detailed Description
In order to make those skilled in the art better understand the technical solution of the present invention, the following detailed description of the present invention is provided with reference to specific embodiments.
A method for preparing diosmetin comprises the following steps: diosmin is subjected to enzymolysis by using enzyme; the weight ratio of diosmin to enzyme is 100 (0.60-23.81).
Preferably, the preparation method specifically comprises: mixing diosmin, enzyme and water for enzymolysis; the weight ratio of the diosmin to the enzyme is 100 (0.60-23.81); the ratio of diosmin to water was 105 kg: 1m3
Preferably, the enzyme is selected from one or more of hesperidinase, rhamnosidase, naringinase, glucosidase and pectinase. Preferably, the ratio of diosmin to enzyme by weight is 100: 2.38.
Preferably, the enzyme is hesperidinase.
Preferably, the enzymolysis temperature is 35-70 ℃, and the enzymolysis time is 12-72 h.
Preferably, the enzymolysis temperature is 40-50 ℃.
Preferably, the enzymatic hydrolysis temperature is 50 ℃.
Preferably, the enzymolysis time is 24 h.
Preferably, the preparation method further comprises: mixing the reaction solvent, hesperidin, alkaline reagent and iodine, and heating for reaction to obtain diosmin.
Preferably, the preparation method further comprises:
(A1) mixing iodine and a reaction solvent to obtain a raw material solution I;
(A2) mixing hesperidin with a reaction solvent to obtain a raw material solution II;
(A3) mixing the raw material solution I and the raw material solution II, heating for reaction, recovering a reaction solvent, adding water, uniformly mixing, filtering, washing with water, and collecting a filter cake;
(A4) mixing and dissolving the filter cake and an alkaline solution, and filtering by using a fine filter to obtain a fine-filtered filtrate;
(A5) and mixing the fine filtered filtrate with hydrochloric acid, crystallizing, filtering, and collecting a filter cake to obtain diosmin.
Preferably, the weight ratio of the hesperidin to the enzyme is 100 (0.5-20).
Preferably, the hesperidin to enzyme weight ratio is 100:2.
Preferably, the weight ratio of iodine to hesperidin is 1: 5 to 15.
Preferably, the weight ratio of iodine to hesperidin is 3: 10.
preferably, the ratio of the reaction solvent to the iodine used in the step (A1) is 1m3:75kg
Preferably, the ratio of the reaction solvent to the hesperidin used in the step (A2) is 1m3:200~300kg。
Preferably, the ratio of the reaction solvent to the hesperidin used in the step (A2) is 1m3:250kg。
Preferably, the step (a3) specifically includes: adding the raw material solution I into the raw material solution II at the flow rate of 400ml/min, heating for reaction, recovering a reaction solvent, adding water, uniformly mixing, filtering, washing with water, and collecting a filter cake.
Preferably, the step (a3) specifically includes: heating the raw material solution II to 70 ℃, adding the raw material solution I into the raw material solution II at the flow rate of 400ml/min, heating to 85 ℃, stirring, reacting for 18h, recovering a reaction solvent, adding water at the temperature of 40-50 ℃, stirring, filtering, washing with water until the pH value of an effluent liquid is 6-7, and collecting a filter cake.
Preferably, hydrochloric acid is added into the filtrate subjected to the fine filtration in the step (A5) to adjust the pH value to 5-6.
Preferably, the reaction solvent is a pyridine or amide solvent.
Preferably, the amide solvent is selected from any one of methylacetamide, ethylacetamide, dimethyloxamide, dimethylacetamide, or dimethylformamide.
Preferably, the amide solvent is N, N dimethylformamide.
Preferably, the reaction solvent is an amide solvent.
Preferably, the alkaline agent is an inorganic alkaline agent.
Preferably, the alkaline agent is selected from one or more of sodium hydroxide, potassium hydroxide, sodium carbonate, sodium bicarbonate and potassium carbonate solution.
Preferably, the alkaline agent is sodium hydroxide.
Preferably, the preparation method further comprises: extracting with ethanol after enzymolysis.
Preferably, the ethanol is 95% ethanol.
Preferably, the preparation method further comprises: filtering after enzymolysis treatment (I), refluxing and extracting by ethanol, filtering (II), collecting filtrate, crystallizing, standing, filtering (III), washing, collecting filter cake, drying and crushing.
Preferably, the filtration (I) is plate and frame filtration.
Preferably, the ethanol extraction process is ethanol reflux extraction.
Preferably, the ethanol extraction process is reflux extraction with 95% ethanol.
Preferably, the reflux extraction process has a reflux extraction time of 2 h.
Preferably, the crystallization process is specifically: adding cooling water, standing and crystallizing.
Preferably, the washing process is specifically: washing with water until no alcohol smell.
Preferably, the preparation method specifically comprises: filtering with plate-frame filter after enzymolysis, reflux extracting with ethanol, filtering (II), collecting filtrate, adding cooling water, standing for crystallization, filtering (III), washing with water until no alcohol smell exists, collecting filter cake, oven drying, and pulverizing.
The reagents used in the examples are commercially available reagents, 95% ethanol is 95% ethanol by volume.
Example 1
A method for preparing diosmetin comprises the following steps:
(A) preparation of diosmetin:
(A1)75kg iodine 1m3Dissolving a reaction solvent (N, N Dimethylformamide (DMF)) to obtain a raw material solution I for later use;
(A2) adding 250kg hesperidin into the mixture for 1m3A reaction solvent (N, N Dimethylformamide (DMF)) to obtain a raw material solution II;
(A3) heating the raw material solution II to 70 ℃, adding the raw material solution I into the raw material solution II at the flow rate of 400ml/min, heating to 85 ℃, stirring, reacting for 18 hours, recovering a reaction solvent, adding water at 40 ℃, stirring uniformly, filtering, washing with water until the pH value of an effluent liquid is 7, and collecting a filter cake;
(A4) and adding hydrochloric acid into the filtrate to adjust the pH value to 5, standing for crystallization, filtering, and collecting a filter cake to obtain 210kg of diosmin.
(B) Enzymolysis: adding 210kg of diosmin into the mixture for 2m3Stirring and mixing uniformly in water, adding hesperidin in an amount of 2% of the weight of hesperidin (2.38% of the weight of diosmin) for enzymolysis, and performing enzymolysis at 50 ℃ for 24 hours to obtain an enzymolysis product;
(C) refining: filtering zymolyte, collecting solid filter cake, and collecting solid with a volume of 2m3Dissolving with 95% ethanol, reflux extracting for 2h, filtering, collecting filtrate, recovering ethanol to obtain filtrate 200L, adding cooling water, crystallizing, standing for 8h, filtering, washing with water until no alcohol smell is produced, collecting filter cake, oven drying, and pulverizing to obtain refined diosmetin 95 kg.
The yield of diosmetin is 45 percent
HPLC external standard method for detecting diosmetin content
Chromatographic conditions are as follows: specification and model of the chromatographic column: c18: column temperature 40 ℃ C. 100X 4.6mm X3 um
Flow rate 1.5 ml/min; mobile phase: acetonitrile-glacial acetic acid-methanol-water; detection wavelength: 275nm
Diosmetin test samples: the refined diosmetin prepared in example 1.
Preparation of a test solution: weighing 25mg of diosmetin sample, adding dimethyl sulfoxide into a 25ml volumetric flask, carrying out ultrasonic treatment for about 5min to completely dissolve the sample, cooling to room temperature (15-35 ℃) and then metering to 25ml with dimethyl sulfoxide to obtain the diosmetin.
Diosmetin control: diosmetin work reference.
Preparation of a reference solution: weighing 25mg of diosmetin working reference substance, adding dimethyl sulfoxide into a 25ml volumetric flask, performing ultrasonic treatment for about 5min to completely dissolve a test sample, cooling to room temperature, and metering to 25ml with dimethyl sulfoxide to obtain the diosmetin.
The detection method comprises the following steps: and (3) balancing the chromatographic system for 30-60min under the chromatographic conditions, automatically sampling the solutions in sequence after the baseline is stable, and automatically integrating by an instrument and keeping the chromatogram.
And (3) calculating the content:
Figure RE-GDA0003519645420000081
the content calculation formula is as follows:
Figure RE-GDA0003519645420000082
Atest articleIs the peak area of the test sample;
Areference substancePeak area for control;
Mtest articleThe concentration is the concentration of the test solution, mg/ml;
Mreference substanceThe concentration of the reference solution is mg/ml;
Creference substance-is the nominal content of the control substance%
LOD is the loss on drying,%, of the test sample;
the refined diosmetin prepared in example 1 has an external standard HPLC content of 98% and a purity of 99%.
Example 2
This example differs from example 1 only in that: in this example, the reaction solvent was pyridine. (alternative is the reaction solvent example 1 (N, N Dimethylformamide (DMF))
Example 3
This example differs from example 1 only in that: the enzymolysis temperature is 55 ℃.
Example 4
This example differs from example 1 only in (B) enzymatic hydrolysis: adding 210kg of diosmin into the mixture for 2m3Stirring and mixing uniformly in water, adding hesperidin 0.3% (0.36% of diosmin) for enzymolysis, and performing enzymolysis at 50 deg.C for 24 hr to obtain zymolyte;
example 5
This example differs from example 1 only in (B) enzymatic hydrolysis: adding 210kg of diosmin into the mixture for 2m3Stirring in water, adding hesperidin 0.5 wt% (0.60 wt% of diosmin) of hesperidin, and performing enzyme treatmentHydrolyzing, and performing enzymolysis at 50 deg.C for 24 hr to obtain zymolyte.
Example 6
This example differs from example 1 only in (B) enzymatic hydrolysis: enzymolysis with rhamnosidase.
Example 7
This example differs from example 1 only in (B) enzymatic hydrolysis: enzymolysis with naringinase.
Example 8
This example differs from example 1 only in (B) enzymatic hydrolysis: enzymolysis with glucosidase.
Example 9
This example differs from example 1 only in (B) enzymatic hydrolysis: enzymolysis with pectinase.
Effect example 1
Diosmetin was prepared according to the preparation method of example 1, the yield of the reaction carried out under different dosages of hesperidinase, the content and purity detected by HPLC external standard method were measured, and the results are shown in Table 1
TABLE 1
Figure RE-GDA0003519645420000101
The best usage amount of hesperidin is 2% (2.38% by weight of diosmin) for enzymolysis, the lower limit is 0.5% (0.60% by weight of diosmin) by weight of hesperidin, and the upper limit is 20% (23.81% by weight of diosmin) by weight of hesperidin. More than 20% by weight of hesperidin (23.81% by weight of diosmin) causes enzyme waste and increases production cost. When the amount of the diosmin is small, the reaction of the diosmin is incomplete, and the purity of the obtained product is low.
Effect example 2
Diosmetin was prepared according to the preparation method of example 1, the yield of the reaction carried out under different enzymolysis temperature and enzymolysis time conditions, the content and purity detected by HPLC external standard method were measured, and the results are shown in Table 2 (the amount of hesperidin used is 2% of the weight of hesperidin)
TABLE 2
Figure RE-GDA0003519645420000102
Figure RE-GDA0003519645420000111
The enzymolysis temperature and the enzymolysis time have obvious quality influence on the yield of the product and the content and the purity detected by an HPLC external standard method. The enzymolysis temperature is 35-70 ℃, and the enzymolysis time is 12-72 h. Preferably, the enzymolysis temperature is 40-50 ℃. The enzymolysis temperature is 50 ℃, the enzymolysis time exceeds 24 hours, and the content and purity detected by an HPLC external standard method are not obviously changed, so the preparation efficiency and the cost are considered, and the enzymolysis temperature is most preferably 50 ℃, and the enzymolysis time is 24 hours.
The above is only a preferred embodiment of the present invention, and it should be noted that the above preferred embodiment should not be considered as limiting the present invention, and the protection scope of the present invention should be subject to the scope defined by the claims. It will be apparent to those skilled in the art that various modifications and adaptations can be made without departing from the spirit and scope of the invention, and these modifications and adaptations should be considered within the scope of the invention.

Claims (10)

1. A method for preparing diosmetin is characterized by comprising the following steps: diosmin is subjected to enzymolysis by using enzyme; the weight ratio of diosmin to enzyme is 100 (0.60-23.81).
2. The preparation method according to claim 1, wherein the preparation method specifically comprises: mixing diosmin, enzyme and water for enzymolysis; the weight ratio of the diosmin to the enzyme is 100 (0.6-23.81); the ratio of diosmin to water was 105 kg: 1m3
3. The method according to claim 1, wherein the enzyme is one or more selected from the group consisting of hesperidinase, rhamnosidase, naringinase, glucosidase and pectinase.
4. The method of claim 1, wherein the ratio of diosmin to enzyme by weight is 100: 2.38.
5. The preparation method according to claim 1, wherein the enzymolysis temperature is 35-70 ℃ and the enzymolysis time is 12-72 h.
6. The preparation method according to claim 5, wherein the enzymolysis temperature is 50 ℃ and the enzymolysis time is 24 h.
7. The method of manufacturing according to claim 1, further comprising: mixing the reaction solvent, hesperidin, alkaline reagent and iodine, and heating for reaction to obtain diosmin.
8. The method of manufacturing according to claim 7, further comprising:
(A1) mixing iodine and a reaction solvent to obtain a raw material solution I;
(A2) mixing hesperidin with a reaction solvent to obtain a raw material solution II;
(A3) mixing the raw material solution I and the raw material solution II, heating for reaction, recovering a reaction solvent, adding water, uniformly mixing, filtering, washing with water, and collecting a filter cake;
(A4) mixing and dissolving the filter cake and an alkaline solution, and filtering by using a fine filter to obtain a fine-filtered filtrate;
(A5) and mixing the fine filtered filtrate with hydrochloric acid, crystallizing, filtering, and collecting a filter cake to obtain diosmin.
9. The method of manufacturing according to claim 1, further comprising: extracting with ethanol after enzymolysis.
10. The method of manufacturing according to claim 9, further comprising: filtering after enzymolysis treatment (I), extracting with ethanol, filtering (II), collecting filtrate, crystallizing, standing, filtering (III), washing, collecting filter cake, drying, and pulverizing.
CN202111255615.5A 2021-10-27 2021-10-27 Preparation method of diosmetin Pending CN114317630A (en)

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CN102070689A (en) * 2011-01-25 2011-05-25 湖南圆通药业有限公司 Method for producing diosmin
CN103819520A (en) * 2014-02-14 2014-05-28 闻永举 Method for preparing mono-glucoside through selective hydrolysis of flavone rutinoside or neohesperidoside
WO2014131995A1 (en) * 2013-02-28 2014-09-04 Les Laboratoires Servier Method for the enzymatic synthesis of diosmetin derivatives
CN105732744A (en) * 2016-04-29 2016-07-06 南京正大天晴制药有限公司 Method for preparing green and economic diosmin
CN109180627A (en) * 2018-09-06 2019-01-11 陕西嘉禾生物科技股份有限公司 A kind of semisynthesis of diosmetin
CN111100104A (en) * 2019-12-26 2020-05-05 陕西嘉禾药业有限公司 Preparation method of diosmetin

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20080049174A (en) * 2006-11-30 2008-06-04 (주)아모레퍼시픽 Preparing method of diosmetin from lemon peel and the cosmetic composition containing thereof as active ingredient
CN102070689A (en) * 2011-01-25 2011-05-25 湖南圆通药业有限公司 Method for producing diosmin
WO2014131995A1 (en) * 2013-02-28 2014-09-04 Les Laboratoires Servier Method for the enzymatic synthesis of diosmetin derivatives
CN103819520A (en) * 2014-02-14 2014-05-28 闻永举 Method for preparing mono-glucoside through selective hydrolysis of flavone rutinoside or neohesperidoside
CN105732744A (en) * 2016-04-29 2016-07-06 南京正大天晴制药有限公司 Method for preparing green and economic diosmin
CN109180627A (en) * 2018-09-06 2019-01-11 陕西嘉禾生物科技股份有限公司 A kind of semisynthesis of diosmetin
CN111100104A (en) * 2019-12-26 2020-05-05 陕西嘉禾药业有限公司 Preparation method of diosmetin

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