Method for preparing baicalin-7-glucoside

Abstract

The invention belongs to the technical field of medicines, and discloses a simple and convenient method for preparing baicalin-7-glucoside. According to the method, baicalin is taken as a starting material, and the method comprises the following step: synthesising baicalin-7-glucoside by a one-pot two-step method, wherein the reagent used in the method is a laboratory common reagent, and moreover, the reduction reaction of a key step in the reaction can be carried out in a room-temperature condition; therefore, the method disclosed by the invention is easily available in needed materials, low in cost, simple in reaction operation, easy to treat, and capable of obtaining lots of baicalin-7-glucoside for the use of medical research and development.

Description

technical field

[0001] The invention belongs to the technical field of medicine, and in particular relates to a method for preparing oreoside A. Background technique

[0002] Flavonoids are widely distributed in vegetables, fruits and herbal medicines, and have extremely high medicinal value, such as anti-oxidation, anti-inflammation, anti-tumor, immune regulation, etc., and their development is of great significance. In addition to some common flavonol glycosides, such as quercetin glycosides and kaempferol glycosides, which have been proven to have good biological activities, flavonoid glycosides have also been extensively studied in recent years. For example, some flavonoid glycosides have good anti-tumor, anti-inflammatory, anti-plasmodium or anti-trypanosome effects.

[0003] Extracting flavonoid glycosides from natural plants is its main source, but it also makes its production cost relatively high, which has become a major obstacle restricting its further application...

Examples

Embodiment 1

[0022] A method for preparing oreoside A, comprising the following steps:

[0023] 1) Add 0.9g baicalin and 50mL ethanol to a 100mL flask, add a catalytic amount of concentrated sulfuric acid dropwise at 0°C, place the reaction bottle in an oil bath, heat and reflux for 2 hours; the color of the solution starts to turn yellow, and then spot the TLC plate Determine the degree of reaction, and cool the obtained yellow liquid to room temperature after the end of the reaction;

[0024] 2) At 0°C, add 380 mg of reducing agent sodium borohydride in batches to the yellow liquid in step 1), and react at room temperature for 1 hour;

[0025] 3) Step 2) After the reaction, add 5 mL of ethyl acetate, continue the reaction at room temperature for 20 minutes, spin the reaction solution to dryness, then add 5 mL of ethyl acetate and 5 mL of acetic acid aqueous solution with a volume fraction of 10%, and obtain a large amount of yellow solid after stirring. Suction filtration obtains the cr...

Embodiment 2

[0028] A method for preparing oreoside A, comprising the following steps:

[0029] 1) Add 0.9g baicalin and 50mL methanol into a 100mL flask, add a catalytic amount of concentrated sulfuric acid dropwise at 0°C, place the reaction bottle in an oil bath, heat and reflux for 3 hours; the color of the solution starts to turn yellow, and then spot the TLC plate Determine the degree of reaction, and cool the obtained yellow liquid to room temperature after the end of the reaction;

[0030] 2) At 0°C, add 380 mg of reducing agent sodium borohydride in batches to the yellow liquid in step 1), and react at room temperature for 2 hours;

[0031] 3) Step 2) After the reaction, add 5 mL of ethyl acetate, continue the reaction at room temperature for 10 minutes, spin the reaction solution to dryness, then add 5 mL of ethyl acetate and 5 mL of acetic acid aqueous solution with a volume fraction of 10%, and obtain a large amount of yellow solid after stirring. Suction filtration obtains th...

Embodiment 3

[0034] A method for preparing oreoside A, comprising the following steps:

[0035] 1) Add 0.9g baicalin and 50mL methanol into a 100mL flask, add a catalytic amount of concentrated sulfuric acid dropwise at 0°C, place the reaction bottle in an oil bath, heat and reflux for 2 hours; the color of the solution starts to turn yellow, and then spot the TLC plate Determine the degree of reaction, and cool the obtained yellow liquid to room temperature after the end of the reaction;

[0036] 2) At 0°C, add 540 mg of reducing reagent potassium borohydride in batches to the yellow liquid in step 1), and react at room temperature for 3 hours;

[0037] 3) Step 2) After the reaction, add 5 mL of ethyl acetate, continue the reaction at room temperature for 30 minutes, spin the reaction solution to dryness, then add 5 mL of ethyl acetate and 5 mL of acetic acid aqueous solution with a volume fraction of 10%, and obtain a large amount of yellow solid after stirring. Suction filtration obtai...

technical field

[0001] The invention belongs to the technical field of medicine, and in particular relates to a method for preparing oreoside A. Background technique

[0002] Flavonoids are widely distributed in vegetables, fruits and herbal medicines, and have extremely high medicinal value, such as anti-oxidation, anti-inflammation, anti-tumor, immune regulation, etc., and their development is of great significance. In addition to some common flavonol glycosides, such as quercetin glycosides and kaempferol glycosides, which have been proven to have good biological activities, flavonoid glycosides have also been extensively studied in recent years. For example, some flavonoid glycosides have good anti-tumor, anti-inflammatory, anti-plasmodium or anti-trypanosome effects.

[0003] Extracting flavonoid glycosides from natural plants is its main source, but it also makes its production cost relatively high, which has become a major obstacle restricting its further application...

Examples

Embodiment 1

[0022] A method for preparing oreoside A, comprising the following steps:

[0023] 1) Add 0.9g baicalin and 50mL ethanol to a 100mL flask, add a catalytic amount of concentrated sulfuric acid dropwise at 0°C, place the reaction bottle in an oil bath, heat and reflux for 2 hours; the color of the solution starts to turn yellow, and then spot the TLC plate Determine the degree of reaction, and cool the obtained yellow liquid to room temperature after the end of the reaction;

[0024] 2) At 0°C, add 380 mg of reducing agent sodium borohydride in batches to the yellow liquid in step 1), and react at room temperature for 1 hour;

[0025] 3) Step 2) After the reaction, add 5 mL of ethyl acetate, continue the reaction at room temperature for 20 minutes, spin the reaction solution to dryness, then add 5 mL of ethyl acetate and 5 mL of acetic acid aqueous solution with a volume fraction of 10%, and obtain a large amount of yellow solid after stirring. Suction filtration obtains the cr...

Embodiment 2

[0028] A method for preparing oreoside A, comprising the following steps:

[0029] 1) Add 0.9g baicalin and 50mL methanol into a 100mL flask, add a catalytic amount of concentrated sulfuric acid dropwise at 0°C, place the reaction bottle in an oil bath, heat and reflux for 3 hours; the color of the solution starts to turn yellow, and then spot the TLC plate Determine the degree of reaction, and cool the obtained yellow liquid to room temperature after the end of the reaction;

[0030] 2) At 0°C, add 380 mg of reducing agent sodium borohydride in batches to the yellow liquid in step 1), and react at room temperature for 2 hours;

[0031] 3) Step 2) After the reaction, add 5 mL of ethyl acetate, continue the reaction at room temperature for 10 minutes, spin the reaction solution to dryness, then add 5 mL of ethyl acetate and 5 mL of acetic acid aqueous solution with a volume fraction of 10%, and obtain a large amount of yellow solid after stirring. Suction filtration obtains th...

Embodiment 3

[0034] A method for preparing oreoside A, comprising the following steps:

[0035] 1) Add 0.9g baicalin and 50mL methanol into a 100mL flask, add a catalytic amount of concentrated sulfuric acid dropwise at 0°C, place the reaction bottle in an oil bath, heat and reflux for 2 hours; the color of the solution starts to turn yellow, and then spot the TLC plate Determine the degree of reaction, and cool the obtained yellow liquid to room temperature after the end of the reaction;

[0036] 2) At 0°C, add 540 mg of reducing reagent potassium borohydride in batches to the yellow liquid in step 1), and react at room temperature for 3 hours;

[0037] 3) Step 2) After the reaction, add 5 mL of ethyl acetate, continue the reaction at room temperature for 30 minutes, spin the reaction solution to dryness, then add 5 mL of ethyl acetate and 5 mL of acetic acid aqueous solution with a volume fraction of 10%, and obtain a large amount of yellow solid after stirring. Suction filtration obtai...

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