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Salidroside analogues as well as preparation method and application thereof

A technology of salidroside and analogs, which is applied in the preparation of sugar derivatives, chemical instruments and methods, sugar derivatives, etc., can solve the problems of poor regeneration ability, complex extraction process, reduction of wild resource reserves, etc., and achieve cost reduction. , the effect of shortening the reaction route

Inactive Publication Date: 2011-11-16
NANTONG UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Rhodiola rosea is the most important plant for extracting salidroside, but because it grows in the plateau alpine zone with fragile ecology, its regeneration ability is poor, and its natural regeneration is slow (generally it takes 7-8 years to adopt), and the production needs The consumption of medicinal material resources is quite large, and the reserves of wild resources are decreasing day by day. With the intensification of exploitation, resource depletion will inevitably occur.
The extraction of natural salidroside not only requires a complex extraction process, but the general extraction rate can only reach 0.4-0.8% of the dry weight of the plant

Method used

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  • Salidroside analogues as well as preparation method and application thereof
  • Salidroside analogues as well as preparation method and application thereof
  • Salidroside analogues as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Example 1: Preparation of 1-(4-hydroxy)phenethyl-β-D-glucopyranoside (salidroside, Compound No. 1).

[0044] In a 50ml round bottom flask, add 15ml (2:1) of a mixed solvent of anhydrous dichloromethane and ether, 0.55g (4.0mmol) of tyrosol, 1.2g (4.5mmol) of silver carbonate, and a small amount of iodine (0.1-0.5ml) , 2g of powdered molecular sieves, stirred in the dark for 30min under the protection of nitrogen, added 1.95g (5mmol) of 2,3,4,6-tetra-O-acetyl-α-D-bromoglucopyranose, and reacted at room temperature for 10h. Filter, evaporate the solvent under reduced pressure to obtain a viscous colorless syrup, add 15ml of methanol solution dissolved in potassium carbonate, react at room temperature for 6h, filter, neutralize the acidic resin, separate by column chromatography, methanol:dichloromethane=1: 5. Obtained 0.98g of white solid compound 1, mp159-160°C, yield 81.6%.

Embodiment 2

[0045] Example 2: Preparation of 1-(4-chloro)benzyl-β-D-galactopyranoside (compound 10).

[0046] In a 50ml round-bottomed flask, add 15ml (2:1) of a mixed solvent of anhydrous dichloromethane and ether, 0.57g (4mmol) of 4-chlorobenzyl alcohol, 1.2g (4.5mmol) of silver carbonate, and a small amount of iodine (0.1-0.5 ml), powdered molecular sieve 2g, under the protection of nitrogen, stir in the dark for 30min, add 1.95g (5mmol) of 2,3,4,6-tetra-O-acetyl-α-D-bromoglucopyranose, and react at room temperature for 10h . Filter, evaporate the solvent under reduced pressure to obtain a viscous colorless syrup, add 15ml of methanol solution dissolved in potassium carbonate, react at room temperature for 6h, filter, neutralize the acidic resin, separate by column chromatography, methanol:dichloromethane=1: 6. Obtained 0.95 g of light yellow solid of compound 10, mp 138-140°C, yield 78.1%.

Embodiment 3

[0047] Example 3: Preparation of 1-(3,5-dimethoxy)benzyl-β-D-glucopyranoside (Compound 19).

[0048] In a 50ml round bottom flask, add 15ml (2:1) of a mixed solvent of anhydrous dichloromethane and ether, 0.67g (4mmol) of 3,5-dimethoxybenzyl alcohol, 1.2g (4.5mmol) of silver carbonate, iodine A small amount (0.1~0.5ml), 2g of powdered molecular sieve, stirred for 30min in the dark under the protection of nitrogen, added 1.95g (5mmol ), react at room temperature for 10h. Filter, evaporate the solvent under reduced pressure to obtain a viscous colorless syrup, add 15ml of methanol solution dissolved in potassium carbonate, react at room temperature for 6h, filter, neutralize the acidic resin, separate by column chromatography, methanol:dichloromethane=1: 4. Obtained 1.08 g of white solid compound 19, 146-148 °C, yield 81.8%.

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Abstract

The invention discloses salidroside analogues as well as a preparation method and application thereof. The preparation method comprises the steps such as preparing an intermediate, namely acetyl glucoside, preparing the salidroside analogues and other steps. The obtained products can be used for low-sugar low-serum damage protection of PC12 cells, and the treatment of central nervous and peripheral nervous injury and wasting diseases. In the preparation method, when an aromatic ring contains a hydroxyl group, an acetyl group is used for protecting the hydroxyl group, so that the acetyl group is conveniently removed at the same time of the removal of the acetyl group on a sugar ring, thus avoiding the use of allyl and benzyl protection, shortening the reaction process and lowering the cost; the used solvent is a low-residue aprotic mixed solvent of dichloromethane and diethyl ether, and the glucoside is formed after reacting is performed at room temperature for 10 hours, thus avoiding the use of other more toxic solvents; by using a common inorganic reagent, namely potassium carbonate, the acetyl group is removed, and during column chromatography, dichloromethane is used for substituting for chloroform, thus contributing to the health of operators; and trace iodine is used as a catalyst, anhydrous calcium sulfate is used as a dewatering agent and a powdery 4-angstrom molecular sieve is added.

Description

technical field [0001] The invention relates to a salidroside analogue, a preparation method and application thereof. Background technique [0002] Salidroside (salidroside) is the main active ingredient of Rhodiola (Crassulaceae) in the family Rosaceae (Crassulaceae). obtained in isolation. Salidroside, the English name is Salidroside, and the system name is 2-(4-hydroxyphenethyl)-β-D-glucoside (2-(4-hydroxy)phenethyl-β-D-glucoside). Salidroside can regulate the nervous system, eliminate depression, improve work efficiency, resist hypoxia, resist radiation and eliminate fatigue, and can prevent altitude sickness and improve sleep. As a traditional Chinese medicine with the function of "adaptogen", Rhodiola has been used by many people who are active in special environments, such as divers, astronauts, pilots and mountaineers, to enhance the body's ability to resist harsh environments. [0003] Rhodiola rosea is the most important plant for extracting salidroside, but bec...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H15/18C07H1/00A61K31/7028A61P35/00A61P31/18A61P37/02A61P25/00A61P3/00
Inventor 杨宇民顾晓松丁斐刘梅郭益冰刘炎
Owner NANTONG UNIVERSITY
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