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Method for preparing activity constituent rosavin in rhodiola rosea

An active ingredient, rose red technology, applied in the field of synthesis of active ingredients of Rhodiola rosea, can solve the problems of unsuitable mass production, high cost, and no reports on the chemical synthesis of rosavin.

Inactive Publication Date: 2009-06-17
上海药谷药业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The rosavin products currently on the market are all natural plant extracts, most of which are mixtures, and it is difficult to obtain rosavin with high purity. There is no report on the chemical synthesis of rosavin yet.
It has been reported in the literature that rosavin can be obtained from plant cell culture, but the cost is high and it is not suitable for mass production

Method used

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  • Method for preparing activity constituent rosavin in rhodiola rosea
  • Method for preparing activity constituent rosavin in rhodiola rosea
  • Method for preparing activity constituent rosavin in rhodiola rosea

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Example 1 Synthesis of 6-O-triphenylmethyl-glucose (A1)

[0024]

[0025] (R is Tr R1 is H)

[0026] Dissolve D-glucose (180.16g, 1.0mol) in pyridine (1800ml), add TrCl (362g, 1.3mol) and DMAP (1.833g, 0.015mol), stir overnight at 80°C, TLC (ethyl acetate: methanol = 8: 1) The detection reaction is complete, and it is directly used for the next reaction.

Embodiment 2

[0027] Example 2 Synthesis of 1,2,3,4-tetra-O-benzoyl-6-O-triphenylmethyl-D-glucopyranose (A2)

[0028] Add benzoyl chloride (521ml) dropwise to the solution of compound A1 in an ice-water bath, stir overnight at room temperature, TLC (petroleum ether: ethyl acetate = 4:1) detects that the reaction is complete, add methanol (140.86ml) dropwise to quench the reaction, and use Ethyl acetate (4000ml) was diluted, followed by 3% HCl solution (1500ml*4), saturated NaHCO 3 The solution (1500ml*1) and saturated brine (1500ml*2) were washed, dried over anhydrous sodium sulfate, filtered, and concentrated to obtain about 900g of a brown syrupy product. .

Embodiment 3

[0029] Example 3 Synthesis of 1,2,3,4-tetra-O-benzoyl-D-glucopyranose (A3)

[0030] Dissolve A2 (900g) in dichloromethane (2000ml), add methanol (1000ml), add p-toluenesulfonic acid to adjust the pH of the reaction solution to 2, stir at room temperature overnight, and detect by TLC (petroleum ether: ethyl acetate = 4:1) After the reaction was complete, triethylamine was added to adjust the pH of the reaction solution to 7, concentrated, and column chromatography (eluent: petroleum ether: ethyl acetate = 4:1) gave 381.8 g of a light yellow solid, HPLC: 87.73%.

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Abstract

The invention relates to a synthesis method for Beta-(E)-cinnamic alcohol group-O-[6'-O- Alpha-L-arabopyranose group]-D-glucose pyranoside (Rosavin). The method comprises: carrying out the glycoside reaction on Cinnamic alcohol and 2,3,4-tri-O-benzoyl-[6-O-(2',3',4'-tri-O-acetyl)-L-furan arabopyranose group ]-D-furan glucose trichloroacetimidate, and then removing a protective group, so as to obtain the Beta-(E)-cinnamic alcohol group-O-[6'-O- Alpha-L-arabopyranose group]-D-glucose pyranoside. The method has easily obtained raw materials, moderate reaction conditions and high product purity. The method is not reported in a document. Therefore, the synthesis method is a novel method for artificially synthesizing Rosavin.

Description

technical field [0001] The invention relates to a method for synthesizing the active ingredient of Rhodiola rosea, specifically β-(E)-cinnamyl-O-[6'-O-α-L-arabinopyranosyl]-D- The synthetic method of glucopyranoside (Rosavin). [0002] Its structure is as follows [0003] Background technique [0004] Rhodiola rosea (Rhodiola rosea L.), also known as "Rhodiola rosea", belongs to the genus Rhodiola (Crassulaceae) of Crassulaceae, a perennial herb or subshrub. About 70cm high, the flowers are yellow in color, and its roots and rhizomes are used medicinally. It mainly grows in arid sandy land and high-altitude mountains at an altitude of about 1000-5000 meters in Europe and Asia. It is named after its newly cut rhizomes that emit a rose-like aroma. Rhodiola rosea is famous for its effects of eliminating fatigue, anti-hypoxia, anti-depression, anti-microwave radiation and delaying aging. It is a traditional herbal medicine known as "Plateau Ginseng". Pharmacological exper...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H15/18
CPCY02P20/55
Inventor 惠永正杨志奇王爱玲
Owner 上海药谷药业有限公司
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