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Preparation method of flavone aglycone or monoglycoside from aluminum-salt-flavonoid-glycoside complex through hydrolysis

A technology of flavone monoglycoside and flavone aglycone, which is applied in the fields of chemistry and medicine, can solve the problems of long hydrolysis time, poor selectivity, cumbersome operation, etc., and achieves simple and easy method, high yield and yield, and short hydrolysis time Effect

Inactive Publication Date: 2016-04-13
闻永举
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to the poor selectivity, the yield of flavone monoglycosides is low and does not have practical value
The macroporous adsorption resin is hydrolyzed with the adsorbable flavonoid glycosides, but it needs to be pre-adsorbed, the acid concentration is high, and the hydrolysis time is long, and it needs to be eluted after hydrolysis, etc. The operation is slightly cumbersome

Method used

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  • Preparation method of flavone aglycone or monoglycoside from aluminum-salt-flavonoid-glycoside complex through hydrolysis
  • Preparation method of flavone aglycone or monoglycoside from aluminum-salt-flavonoid-glycoside complex through hydrolysis
  • Preparation method of flavone aglycone or monoglycoside from aluminum-salt-flavonoid-glycoside complex through hydrolysis

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0018] Take 3.0g of anhydrous aluminum chloride, quickly add 60ml of glycerin, 10ml of ethanol, stir evenly, 20g of 92% hesperidin, stir evenly, hydrolyze under reflux at 85°C, follow-up inspection by HPLC / TLC until there is no hesperidin and Hesperetin-7-O-glucoside (about 15h, add 5ml of phosphoric acid, mix well, slowly pour the above hydrolyzate into 500ml of 1% phosphoric acid aqueous solution, statically precipitate light yellow precipitate, filter, wash, and put the filter cake in In 70% ethanol solution, heat to dissolve, add 0.1% phosphoric acid, let cool, filter with suction, wash with water, and dry at 60°C to obtain 9.1g of hesperetin, which is 93.6% determined by HPLC, melting point and UV spectrum peak shape , HPLC were consistent with the hesperetin reference substance.

[0019]

[0020]

example 2

[0022] Take 6H 2 O-aluminum trichloride 6.0g, add glycerol-ethanol (40:10) mixed solvent 50ml, 85% baicalin 10g, anhydrous calcium chloride 4.0g, heat to dissolve, add sulfuric acid 2ml, stir evenly, put Hydrolyze at 90°C under airtight reflux, follow up and check by HPLC / TLC until there is no baicalin (about 16 hours, the solution is first turbid, then clear, and then precipitate), slowly add 4ml of phosphoric acid, stir, and slowly pour the above hydrolyzate into 500ml0.5% In phosphoric acid water, precipitate precipitates, filter, wash with water, drain the filter cake, place in 50ml of 0.1% phosphoric acid methanol solution, ultrasonicate for 20min, let cool, filter, wash with cold water, and dry at 60°C to obtain baicalein 5.6 g, the content determined by HPLC is 90.4%, and the melting point, UV spectrum peak shape, and retention time of HPLC are all consistent with the baicalein reference substance.

[0023]

[0024]

example 3

[0026] Take 6H 2 Add 6.0g of O-aluminum trichloride, add 100ml of methanol solvent, take 10g of 98% rhubaricin, heat and dissolve in a closed manner at 80°C, add 6ml of hydrochloric acid, and follow up with HPLC / TLC for hydrolysis at 80°C until all rhoantisides produce apigenin (About 16 hours, the clear solution will precipitate out) Add 5ml of phosphoric acid, sonicate for 30min, filter, combine the filter cake, place in 0.2% phosphoric acid solution, sonicate for 20min, filter, wash with water, and dry at 60°C to get apigenin 4.1 g, the retention time of melting point, UV spectrum peak shape, and HPLC are all consistent with the apigenin reference substance.

[0027]

[0028]

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Abstract

Disclosed is a preparation method of flavone aglycone or monoglycoside from aluminum-salt-flavonoid-glycoside complex through hydrolysis. The problems that flavonoid glycosides neither dissolve in water nor are hard to dissolve in a common organic alcohol solution, and flavone aglycone prepared from hydrolysis has slow hydrolysis speed, needs a large amount of an organic solvent, and cannot be totally hydrolyzed are solved. A complex product from complexation of aluminum salt and flavonoid glycosides is easy to dissolve in alcohol, hydrogen chloride generated by the complex product is utilized with addition of hydrochloric acid or sulfuric acid, and hydrolysis is carried out at a certain temperature to prepare aglycone or a mixture of aglycone and monoglycoside. After the reaction is over, phosphoric acid or phosphate is added to break complexation of aluminum ions and flavone to obtain flavone aglycone, or the mixture of flavone aglycone and flavone monoglycoside, or a mixture of flavone aglycone, flavone monoglycoside, and flavonoid glycoside. The method is simple and easy to operate, relatively high in yield and purity, and extremely low in cost, and is suitable for massive industrial production of flavone aglycone or the mixture of flavone aglycone and flavone monoglycoside.

Description

technical field [0001] The invention relates to a method for preparing flavone aglycones or monoglycosides thereof by hydrolyzing aluminum salt complexed flavone glycosides, and the field of the invention is chemistry and medicine. Background technique [0002] Flavonoids refer to compounds made of two benzene rings connected by three carbons, which are widely found in nature. Flavonoids are usually combined with sugars in plants to form glycosides, and a small part exists in the form of free states (glycones) . Because the flavonoid glycoside molecule contains two benzene rings, it has good planarity, and it is easy to crystallize between molecules, which leads to its low solubility in water and organic solvents, and it is difficult to hydrolyze. For example, the solubility of hesperidin in water is 50L / g, slightly soluble in methanol, insoluble in ethanol, acetone and other organic solvents; diosmin is insoluble in water and common organic solvents, and baicalin is insolu...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H15/203C07H17/07C07H1/00C07D311/32C07D311/30
Inventor 闻永举申秀丽梁爱军
Owner 闻永举
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