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Flavanone glycoside and its preparation and use

A flavanone and glycoside technology, which is applied in the directions of sugar derivatives, medical preparations containing active ingredients, organic active ingredients, etc., can solve the problems of difficult processing, many reaction steps, and long reaction time.

Inactive Publication Date: 2005-03-16
NANJING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] There are certain limitations in the above three methods. Method one is difficult to deal with after the reaction due to the high concentration of silver salt in the system; the reaction time of method two is long; the reaction steps of method three are many

Method used

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  • Flavanone glycoside and its preparation and use
  • Flavanone glycoside and its preparation and use
  • Flavanone glycoside and its preparation and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Embodiment 1, the preparation of 6-L-rhamnopyranosyl flavanone (IV)

[0027]

[0028] 1. Preparation of 6-(2,3,4-triacetyl-L-rhamnopyranosyl)flavanone (III):

[0029] 6-Hydroxyflavanone (I) (0.484g, 2.017mmol) and 2,3,4-triacetyl-1-oxo-L-rhamnopyranosyltrichloroethylimine (II) (0.884g , 2.035mmol) were mixed, and after vacuum drying for 2h, 54ml of anhydrous CH was added to the mixture 2 Cl 2 , the system was cooled to -42°C in a liquid nitrogen-ethanol bath, N 2 Under protection, 46 μl of trimethylsilyl trifluoromethanesulfonate was added dropwise, and after the addition was completed, the reaction system gradually returned to room temperature, and the total reaction time was about 3 hours. 3: 2) After monitoring the reaction, triethylamine was added to the system to terminate the reaction, and the solvent was removed by a rotary evaporator to obtain a brownish-yellow viscous liquid, which was separated and purified by column chromatography (eluent: petroleum eth...

Embodiment 2

[0048] Example 2, Preparation of 6-D-glucopyranosylflavanone (VII)

[0049]

[0050] 1. Preparation of 6-(2,3,4,6-tetraacetyl-D-glucopyranosyl)flavanone (VI):

[0051] 6-Hydroxyflavanone (I) (0.507g, 2.113mmol) and 2,3,4,6-tetraacetyl-1-oxo-D-glucopyranosyl trichloroethylimine (V) (1.040 g, 2.111mmol) were mixed, and after vacuum drying for 2h, 70ml of anhydrous CH was added to the mixture 2 Cl 2 , the system was cooled to -78°C in a liquid nitrogen-ethanol bath, N 2 Under protection, 45 μl of trimethylsilyl trifluoromethanesulfonate was added dropwise. After the addition was complete, the reaction system returned to room temperature gradually. 3: 2) After monitoring the reaction, triethylamine was added to the system to terminate the reaction, and the solvent was removed by a rotary evaporator to obtain a brownish-yellow viscous liquid, which was separated and purified by column chromatography (the eluent was petroleum ether: ethyl acetate =3:1) to obtain 0.610 g of li...

Embodiment 3

[0070] Example 3, Preparation of 3-L-rhamnopyranosylflavanone (XII)

[0071]

[0072] The preparation of 1.3-hydroxyl-4-flavanone dimethyl acetal (IX):

[0073] Flavanone (VIII) (4.48g, 0.02mol) was mixed with 100ml of absolute anhydrous methanol, cooled to 0°C, and a mixed solution of potassium hydroxide (3.36g, 0.06mol) and 50ml of methanol was added dropwise, the solution was brownish yellow, Add in batches (4 to 5 parts) iodobenzene diacetate (C 6 h 5 IO(Ac) 2 , 7.0 g, 0.02 mol), for about 5 minutes, the mixture was stirred at 0° C. for 1 hour, then the ice bath was removed, and stirred overnight at room temperature. After methanol was removed by rotary evaporation, 100ml of water and potassium carbonate were added to the system for neutralization, and extracted 5 times with ether, about 40ml each time. The organic phases were combined and dried over anhydrous magnesium sulfate. After removing the desiccant by filtration, the solution was concentrated to give a colo...

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PUM

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Abstract

The invention provides a flavanones group glycoside compounds having the structural formula disclosed in the specification, the compound has both appreciable inhibitory action to mixed lymphocyte reaction, apoptosis inducement activity to splenocyte activated by 2,4,6-trinitrochlorobenzene and sheep red blood cells, and evident inhibitory action for the splenocyte NO secretion by PC1-CS model mouse. The invention also discloses the process of preparation.

Description

technical field [0001] The present invention relates to flavanone glycosides. Background technique [0002] Flavonoid glycosides are a class of natural organic compounds that widely exist in nature. They have a series of important physiological activities. sex inhibitors. 3,7,3',4'-tetrahydroxy-3-L-rhamnopyranosylflavanone (Astilbin) and its analogs 5,7,3',5'-tetrahydroxy-3-L- 3-Glycosylflavanone glycosides such as rhamnopyranosylflavanone (Smitilibin) show selective immunosuppressive effects on the overall disease model or cell model, and do not have the common toxic side effects of existing drugs. [0003] [0004] However, since there are few effective methods for the synthesis of flavonoid glycosides, most flavonoid glycosides mainly rely on natural extraction. So far, the synthetic methods of the reported flavonoid glycosides have the following three kinds: [0005] Method 1: Horhammer and Wagner (1968) reported for the first time that 7,4'-dibenzyloxyquercetin a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/7048A61P37/02C07H17/07
Inventor 郭子建杨晓亮徐强孙洋张子超
Owner NANJING UNIV
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