Method for preparing mono-glucoside through selective hydrolysis of flavone rutinoside or neohesperidoside

A new technology of hesperidoside and rutinoside, which is applied in the fields of chemistry and medicine, and can solve problems such as inability to disperse and difficulty in dissolving

Inactive Publication Date: 2014-05-28
闻永举
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Solve the problem that it is difficult to dissolve and cannot be dispersed in ketone solvents such as acetone;

Method used

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  • Method for preparing mono-glucoside through selective hydrolysis of flavone rutinoside or neohesperidoside

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preparation example Construction

[0051] The invention discloses flavone rutinoside compounds or flavone neohesperidoside compounds, which are adsorbed, dispersed and solidified by a macroporous adsorption resin, and rhamnose and ketones in the molecule are condensed to form flavone rutinoside ketal compounds or flavones Neohesperidoside ketal compounds, a general preparation method for preparing flavonoid glucoside compounds by hydrolyzing rhamnose. Those skilled in the art can refer to the content of this article to appropriately improve the process parameters of different flavonoid rutinosides or neohesperidoside compounds, such as adjusting the type and amount of resin; the type and amount of ketone; the type and amount of acid; temperature, etc. To realize the hydrolysis of different flavone rutinosides or neohesperidose compounds to prepare flavone monoglucoside. In particular, it should be pointed out that in the process of hydrolyzing various flavone rutinosides or neohesperidosides to prepare flavone ...

Embodiment 1

[0054] Example 1: Preparation of diomin-7-O-glucoside by diomin

[0055] Weigh 10g of 90% diomin, add 3.0g of KOH, add 150ml of water, shake well until the hesperidin dissolves (red-brown solution), add 140g (246ml) of macroporous adsorption resin, shake well, and slowly Slowly add acetic acid dropwise until acidic (red-brown color gradually fades), then add 2ml of acetic acid, shake well, add 10g of macroporous adsorption resin, shake well, let stand for 30min, filter, wash with 300ml of water several times until filtered, pump To dry, wrap the macroporous adsorption resin with paper and dry at 60°C. Put the macroporous adsorption resin in a 500ml flask, add 150ml of acetone (AR), soak for 1 hour, shake until no bubbles emerge from the resin, quickly add 3.g of anhydrous calcium chloride, add 1ml of concentrated sulfuric acid, shake well, ℃ air bath, airtight hydrolysis, TLC tracking (every 4h) inspection, until there is no obvious spot on TLC of diomin and its ketal compoun...

Embodiment 2

[0057] Example 2: Preparation of apigenin-7-O-glucoside from Rhododendron

[0058] Weigh 10g of 98% Rhodoglucoside, add 3.0g of KOH, add 140ml of water, shake well until the Rhodoglucoside is dissolved (brownish yellow solution), add 140g (245ml) of macroporous adsorption resin, shake well, shake while slowly Slowly add acetic acid dropwise to acidity (the color of rhotropin fades gradually), then add 2ml of acetic acid, shake well, add 10g of macroporous adsorption resin, shake well, let stand for 30min, filter, wash with 300ml of water several times, filter, pump To dry, wrap the macroporous adsorption resin with paper and dry at 60°C. Put the macroporous adsorption resin in a 500ml flask, add 150ml of acetone (AR), infiltrate for 1 hour, shake until no bubbles emerge from the resin, quickly add 3.g of anhydrous calcium chloride, add 1ml of methanesulfonic acid, shake well, and In an air bath at 50°C, airtight hydrolysis, TLC tracking (every 4h) inspection, until there are ...

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Abstract

The invention relates to a method for preparing mono-glucoside through selective hydrolysis of flavone rutinoside or neohesperidoside, and belongs to the fields of chemistry and medicine. The method comprises the following steps: mixing flavone rutinoside or neohesperidoside with macroporous absorption resin in water or alkaline water solution, heating or adding acid; wherein in this process the diglucoside is dispersed, absorbed, and cured by the macroporous absorption resin; after drying, in the catalysis of acid or a dewatering agent, rhamnose in the molecule carries out condensation reactions with a ketone agent, and the rhamnose in the molecule is removed in the action of acid; eluting with an organic solvent or an alkaline water solution; and recycling the solvent or acidifying so as to obtain the flavone mono-glucoside. The method solves the problems that flavone diglucoside is hard to disperse in a ketone reagent and the selectivity of rhamnose hydrolysis is low. The method has the advantages of simple operation, easy recycling of organic solvent, low cost, high yield, and easiness in industrial production. Compounds such as hesperetin mono-glucoside, diosmetin mono-glucoside, hesperetin dihydrochlcone mono-glucoside, and the like, can be industrially produced from flavones such as flavone neohesperidoside through the method.

Description

technical field [0001] The invention relates to a general method for highly selective removal of rhamnose in molecules through adsorption, dispersion and solidification of various flavonoid rutinosides or neohesperidosides by macroporous adsorption resin through ketalization with ketones, and its field belongs to chemistry and medicine. Background technique [0002] Flavonoid rutinoside or neohesperidoside: Flavonoid rutinoside or neohesperidoside widely exists in nature, and has biological activities such as anti-inflammatory, anti-oxidation, antibacterial, anti-tumor, and cardiovascular and cerebrovascular protection. Flavone rutinoside refers to α-L-rhamnosyl (1→6)-β-D-glucosyl-flavone aglycon; flavone neohesperidoside refers to α-L-rhamnosyl (1→2 )-β-D-glucosyl-flavonoid aglycone. Representative compounds of flavonoid rutinoside: rutin (CAS: 153-18-4 ), hesperidin (CAS: 520-26-3 ) and its derivatives diomin (CAS: 520-27-4 ), methyl Hesperidin (CAS: 11013-97-1), hesper...

Claims

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Application Information

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